KR20250043325A - Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices - Google Patents

Abstract

To provide a compound which further improves the performance of an organic EL device, a material for an organic electroluminescence device, an organic electroluminescence device with further improved device performance, and an electronic device including such an organic electroluminescence device, the present invention comprises: a compound represented by the following formula (1A) or formula (1B) (wherein each symbol is as defined in the specification), a material for an organic electroluminescence device including the compound, an organic electroluminescence device including the compound, and an electronic device including such an organic electroluminescence device.

Description

Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices

The present invention relates to a compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device including the organic electroluminescent device.

In general, an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region, and the injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates the recombination of electrons and holes is important for obtaining a high-performance organic EL device.

Patent documents 1 to 3 disclose compounds used as materials for organic electroluminescence devices.

U.S. Patent No. 7598667 Specification Specification of Chinese Patent Application Publication No. 114133333 Specification of United States Patent Application Publication No. 2022/0059771

Although many compounds for organic EL devices have been reported, compounds that further improve the performance of organic EL devices are still in demand.

The present invention has been made to solve the above problems, and has as its object the provision of a compound that further improves the performance of an organic EL device, a material for an organic electroluminescence device, an organic EL device with further improved device performance, and an electronic device including such an organic EL device.

The present inventors have conducted extensive studies on the performance of organic EL devices including novel compounds and have found that organic EL devices including compounds represented by the following formula (1A) or formula (1B) have improved performance.

In one embodiment, the present invention provides a compound represented by the following formula (1A) or formula (1B).

[Chemical Formula 1]

[Chemical formula 2]

[In Equation (1A),

N ^* is the central nitrogen atom.

One selected from Z ¹ and Z ² is a single bond binding to *a.

The above-mentioned Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

Z ¹ and Z ² , R ^13A , and R ^14A , which are not single bonds, do not combine with each other to form a ring.

A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.

A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.

R ^1A and R ^2A are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

R ^1A and R ^2A may be combined with each other to form a ring or may not form a ring.

Y ¹ and Y ² are hydrogen atoms.

L ¹ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

n1 is either 0 or 1.

When n1 is 0, one selected from Z ¹ and Z ² is bonded to the central nitrogen atom N ^* .

X ¹ is an oxygen atom, a sulfur atom, or =CR ^A R ^B.

One selected from R ^A , R ^B , and R ²¹ to R ²⁸ is a single bond binding to *b1, or one selected from R ^A and R ^B is a divalent group binding to *b1.

R ^A and R ^B , which are not single bonds and are not divalent groups bonded to *b1, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R ^A and R ^B , which are not single bonds and are not divalent groups bonded to *b1, may or may not bond to each other to form a ring.

R ²¹ to R ²⁸ , which are not groups bonded to the above *b1, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

When one selected from R ²¹ to ^{R 24} is a group bonded to *b1, R ²¹ to R ²⁴ that are not groups bonded to b1 do not bond to each other to form a ring, and further, R ²⁵ to R ²⁸ may or may not bond to each other to form a ring.

When one selected from R ²⁵ to ^{R 28} is a group bonded to *b1, R ²⁵ to R ²⁸ that are not groups bonded to b1 do not bond to each other to form a ring, and further, R ²¹ to R ²⁴ may or may not bond to each other to form a ring.

L ² is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

n2 is 0 or 1.

When n2 is 0, one selected from R ²¹ to R ²⁸ bonds to the central nitrogen atom N ^* .

Ar ¹ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

m is 0, 1, 2, 3, or 4. However, when Ar ¹ is a hydrogen atom, m is 0.

When m is 1 to 4, 1 to 4 selected from R ³¹ to R ³⁴ are single bonds bonding to *c. When m is 2 to 4, plural Ar ² may be the same or different.

The above R ³¹ to R ³⁴ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

A pair of adjacent groups among Ar ¹ , which is not a hydrogen atom, and R ³⁴ ∼ ^{R 24} , which is not a hydrogen atom, may or may not form a ring by combining with each other.

In equation (1B),

N ^* is the central nitrogen atom.

One selected from R ¹¹ to R ¹⁴ is a single bond bonding to *a.

The above single bonds, R ¹¹ to R ¹⁴ , R ¹⁵ to R ¹⁸ , and R ⁷ to R ¹⁰ , are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.

R ¹¹ to R ¹⁴ , which are not single bonds, do not combine with each other to form a ring.

A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.

A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.

R ^1B , R ^2B , R ^5B , and R ^6B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

R ^1B and R ^2B may be combined with each other to form a ring or may not form a ring.

R ^5B and R ^6B may be combined with each other to form a ring or may not form a ring.

L ³ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

n3 is 0 or 1.

When n3 is 0, Ar ³ binds to the central nitrogen atom N ^* .

Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2).

[Chemical Formula 3]

In equation (2-1),

** indicates the binding position to L ³ .

X ³ is an oxygen atom or a sulfur atom.

One selected from R ⁴¹ to R ⁴⁴ is a single bond bonding to *d.

The above R ⁴¹ to R ⁴⁴ and R ⁴⁵ to R ⁴⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

Among the above-mentioned single bonds, a pair of adjacent groups among R ⁴¹ to ^{R 44} and a pair of adjacent groups among R ⁴⁵ to R ⁴⁸ may or may not be bonded to each other to form a ring.

In equation (2-2),

** indicates the binding position to L ³ .

R ⁴¹ to R ⁴⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

Among R ⁴¹ to R ⁴⁸ , a pair of adjacent groups may combine with each other to form a ring or may not form a ring.

L ⁴ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

n4 is either 0 or 1.

When n4 is 0, Ar ⁴ binds to the central nitrogen atom N ^* .

Ar ⁴ is a group represented by the following formula (3-1) or a group represented by the following formula (3-2).

[Chemical Formula 4]

In equation (3-1),

*** indicates the binding position to L ⁴ .

X ² is an oxygen atom, a sulfur atom, or =CR ^C R ^D.

One selected from R ^21B ∼ R ^24B , R ^C , and R ^D is a single bond binding to *b2, or one selected from R ^C and R ^D is a divalent group binding to *b2.

The above-mentioned R ^21B ∼R ^24B , R ^25B ∼R ^28B , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

When one selected from R ^21B to ^{R 24B} is a single bond bonding to *b2, R ^21B to R ^24B that are not single bonds do not combine with each other to form a ring, and further, R ^25B to R ^28B may or may not combine with each other to form a ring.

When one selected from R ^25B to R ^28B is a single bond bonding to *b2, R ^25B to R ^28B that are not single bonds do not combine with each other to form a ring, and further, R ^21B to R ^24B may or may not combine with each other to form a ring.

The above-mentioned R ^C and R ^D , which are not single bonds and are not divalent groups bonded to the above-mentioned *b2, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, and they may or may not form a ring when bonded to each other. However, when one selected from R ^C and R ^D is an aryl group, the two do not bond to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R ^C and R ^D are bonded.

If X ² is an oxygen atom or a sulfur atom, n4 is 1.

In equation (3-2),

*** indicates the binding position to L ⁴ .

R ^21B ∼R ^28B are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.

A pair of adjacent groups among R ^21B ∼ ^{R 24B} and a pair of adjacent groups among R ^25B ∼ R ^28B may or may not form a ring by combining with each other.

In equation (1-B), L ¹ and n1 have the same meanings as defined in equation (1A).]

In another aspect, the present invention provides a material for an organic electroluminescence device comprising a compound represented by the above formula (1A) or formula (1B).

In another aspect, the present invention provides an organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes a compound represented by the formula (1A) or (1B).

In another aspect, the present invention provides an electronic device including the organic electroluminescent device.

An organic EL device comprising a compound represented by the above formula (1A) or formula (1B) exhibits improved device performance.

FIG. 1 is a schematic diagram showing an example of the layer configuration of an organic EL device according to one embodiment of the present invention.
FIG. 2 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one aspect of the present invention.
FIG. 3 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one embodiment of the present invention.

[definition]

In this specification, the term hydrogen atom includes isotopes having different numbers of neutrons, i.e., protium, deuterium, and tritium.

In this specification, in a chemical structural formula, a hydrogen atom, i.e., a light hydrogen atom, a deuterium atom, or a tritium atom, is assumed to be bonded to a bondable position where a symbol such as “R” or “D” representing a deuterium atom is not specified.

In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbon-carbon ring compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. In addition, for example, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25.

In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

In this specification, the number of ring-forming atoms refers to the number of atoms forming the ring itself of a compound (e.g., a monocyclic compound, a condensed ring, and a ring set) in which atoms are bonded in a ring (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not form a ring (e.g., a hydrogen atom terminating a bond of atoms forming a ring) or atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below shall be the same unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms forming a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. In addition, for example, the hydrogen atom bonded to the carbon atom of the quinazoline ring or the atom forming the substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which the hydrogen atom or the substituent is bonded is 10.

In this specification, in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms", "carbon atoms XX to YY" indicates the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is larger than "XX", "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.

In this specification, in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms", "atom number XX to YY" indicates the number of atoms in the case where the ZZ group is unsubstituted, and does not include the number of atoms of the substituent in the case where it is substituted. Here, "YY" is larger than "XX", "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.

In this specification, an unsubstituted ZZ group indicates a case where a “substituted or unsubstituted ZZ group” is an “unsubstituted ZZ group,” and a substituted ZZ group indicates a case where a “substituted or unsubstituted ZZ group” is a “substituted ZZ group.”

In the present specification, in the case of “substituted or unsubstituted ZZ group,” “unsubstituted” means that the hydrogen atom in the ZZ group is not substituted with a substituent. The hydrogen atom in the “unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.

In addition, in the present specification, in the case of "a substituted or unsubstituted ZZ group", "substitution" means that one or more hydrogen atoms in the ZZ group are substituted with a substituent. In the case of "a BB group substituted with an AA group", "substitution" similarly means that one or more hydrogen atoms in the BB group are substituted with an AA group.

"Substituents described in this specification"

Hereinafter, the substituents described in this specification are described. Unless otherwise stated, each substituent described in this specification is defined as follows.

The number of ring carbon atoms of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

The number of ring atoms of the “unsubstituted heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.

The carbon number of the “unsubstituted alkyl group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

The carbon number of the “unsubstituted alkenyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in this specification.

The carbon number of the “unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in this specification.

The number of ring carbon atoms in the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in this specification.

The number of ring carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

The number of ring atoms of the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.

The carbon number of the “unsubstituted alkylene group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

· "Substituted or unsubstituted aryl group"

Specific examples (specific examples G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific examples G1A) and substituted aryl groups (specific examples G1B). (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when simply referred to as "aryl group", it includes both an "unsubstituted aryl group" and a "substituted aryl group".

A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. As the "substituted aryl group", for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A are replaced with a substituent, and examples of substituted aryl groups of the following specific example group G1B are exemplified. In addition, the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed herein are merely examples, and the "substituted aryl group" described herein also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent.

· Unsubstituted aryl group (specific example group G1A):

Phenyl group,

p-biphenyl group,

m-biphenyl group,

o-biphenyl group,

p-terphenyl-4-yl group,

p-terphenyl-3-yl group,

p-terphenyl-2-yl group,

m-terphenyl-4-yl group,

m-terphenyl-3-yl group,

m-terphenyl-2-yl group,

m-terphenyl-3'-yl group,

o-terphenyl-4-yl group,

o-terphenyl-3-yl,

o-terphenyl-2-yl group,

1-naphthyl group,

2-naphthyl group,

Antril group,

Benzanthryl group,

Phenanthryl group,

Benzophenanthryl group,

Penalen Diary,

Florence Diary,

Chrysen's Diary,

Benzochreisen Diary,

Triphenylene group,

Benzotriphenylene group,

Tetracen Diary,

Pentacen Diary,

Fluorene diary,

9,9'-spirobifluorene diary,

Benzofluorene diary,

Dibenzofluorene diary,

Fluoranthenium diary,

Benzofluoranthene diary,

Perylene diary, and

A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[Chemical Formula 5]

[Chemical formula 6]

· Substituted aryl group (specific example group G1B):

o-tolyl group,

m-tolyl group,

p-tolyl group,

Para-xylyl group,

meta-xylyl group,

Ortho-xylyl group,

para-isopropylphenyl group,

meta-isopropylphenyl group,

Ortho-isopropylphenyl group,

para-t-butylphenyl group,

meta-t-butylphenyl group,

ortho-t-butylphenyl group,

3,4,5-trimethylphenyl group,

9,9-Dimethylfluorenyl group,

9,9-Diphenylfluorenyl group

9,9-bis(4-methylphenyl)fluorenyl group,

9,9-bis(4-isopropylphenyl)fluorenyl group,

9,9-bis(4-t-butylphenyl)fluorenyl group,

cyanophenyl group,

Triphenylsilylphenyl group,

Trimethylsilylphenyl group,

Phenylnaphthyl group,

naphthylphenyl group, and

A group in which at least one hydrogen atom of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) is substituted with a substituent.

· “Substituted or unsubstituted heterocyclic group”

The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom in a ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a condensed ring group.

The “heterocyclic group” described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

Specific examples (specific examples G2) of the “substituted or unsubstituted heterocyclic group” described in this specification include the following unsubstituted heterocyclic groups (specific examples G2A), and substituted heterocyclic groups (specific examples G2B). (Here, the unsubstituted heterocyclic group refers to the case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group,” and the substituted heterocyclic group refers to the case where the “substituted or unsubstituted heterocyclic group” is a “substituted heterocyclic group.”) In this specification, when simply referred to as a “heterocyclic group,” it includes both an “unsubstituted heterocyclic group” and a “substituted heterocyclic group.”

A "substituted heterocyclic group" means a group in which at least one hydrogen atom of an "unsubstituted heterocyclic group" is replaced with a substituent. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B, etc. In addition, the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed herein are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent.

Specific example group G2A includes, for example, an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by any of the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

Specific example group G2B includes, for example, a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which at least one hydrogen atom of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4).

· Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

pyrrolyl group,

imidazolyl group,

Pyrazolyl group,

Triazolyl group,

Tetrazolyl group,

Oxazolyl group,

Isoxazolyl group,

Oxadiazolyl group,

Cyazolyl group,

isothiazolyl group,

Cyadiazolyl group,

Pyridyl group,

The diary of a piri-da-jin,

Pyrimidine diary,

The Pirazin Diary,

Triazine Diary,

Indolyl,

Isoindoleyl,

Indolizine Diary,

Quinolizine diary,

Quinolyl group,

Isoquinolyl group,

Playing with new things,

Phthalazine diary,

Quinazolinic acid,

Quinoxaline Diary,

Benzimidazolyl group,

Indazolyl group,

Phenanthroline diary,

Phenanthridine diary,

Acridine Diary,

Phenazine Diary,

Carbazolyl group,

Benzocarbazolyl group,

Morpholino period,

Penok photo diary,

Phenothiazine Diary,

Azacabazolyl group, and

Diazacabazolyl group.

· Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

Furyl group,

Oxazolyl group,

Isoxazolyl group,

Oxadiazolyl group,

The Diary of Zanten,

Benzofuran diary,

Isobenzofuran diary,

Dibenzofuran diary,

Naphthobenzofuran diary,

Benzoxazolyl group,

Benzisoxazolyl group,

Penok photo diary,

Morpholino period,

Dynaptofuran diary,

Azadibenzofuran diary,

Diazadibenzofuran diary,

Azanaphthobenzofuran diary, and

Diazanaphthobenzofuran diary.

· Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

Cyenne Diary,

Cyazolyl group,

isothiazolyl group,

Cyadiazolyl group,

Benzothiophene diary (benzothiene diary),

Isobenzothiophene diary (isobenzothiazine diary),

Dibenzothiophene diary (dibenzothiazide diary),

Naphthobenzothiophene diary (naphthobenzothiazine diary),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazine Diary,

Dynaptothiophene diary (Dynaptothiene diary),

Azadibenzothiophene diary (azadibenzothiazide diary),

Diazadibenzothiophene dihydroxide (diazadibenzothiophene dihydroxide),

Azanaphthobenzothiophene dihydrochloride (azanaphthobenzothiophene dihydrochloride), and

Diazanaphthobenzothiophene dihydrate (diazanaphthobenzothiaenyl dihydrate).

· A monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[Chemical formula 7]

[Chemical formula 8]

In the above general formulas (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH _2. However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.

In the general formulae (TEMP-16) to (TEMP-33), when at least one of X _A and Y _A is NH or CH ₂ , the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH ₂ .

· Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

(9-phenyl)carbazolyl group,

(9-biphenylyl)carbazolyl group,

(9-phenyl)phenylcarbazolyl group,

(9-naphthyl)carbazolyl group,

Diphenylcarbazol-9-yl group,

Phenylcarbazol-9-yl group,

Methylbenzimidazolyl group,

Ethylbenzimidazolyl group,

Phenyltriazine dihydrate,

Biphenylyltriazine diary,

Diphenyltriazine group,

Phenylquinazolinyl group, and

Biphenylylquinazolinyl group.

· Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

Phenyldibenzofuran dibasic group,

Methyldibenzofuranyl group,

t-butyldibenzofuran diaryl, and

A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

· Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

Phenyldibenzothiophene diary,

Methyldibenzothiophene diary,

t-butyldibenzothiophene diary, and

A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

· A group in which at least one hydrogen atom of a monovalent heterocyclic group derived from a ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4):

The above “one or more hydrogen atoms of a monovalent heterocyclic group” means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of X _A and Y _A is NH, and a hydrogen atom of a methylene group when one of X _A and Y _A is _CH2 .

· “Substituted or unsubstituted alkyl group”

Specific examples (specific examples G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl groups (specific examples G3A) and substituted alkyl groups (specific examples G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", both an "unsubstituted alkyl group" and a "substituted alkyl group" are included.

A "substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced with a substituent, and examples of a substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Meanwhile, the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed herein are only examples, and the "substituted alkyl group" described in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.

· Unsubstituted alkyl group (specific example group G3A):

Methyl group,

Ethyl group,

n-profiler,

Isopropyl group,

n-butyl group,

Isobutyl group,

s-butyl group, and

t-butyl group.

· Substituted alkyl group (specific example group G3B):

Heptafluoropropyl group (including isomers),

pentafluoroethyl group,

2,2,2-trifluoroethyl group, and

Trifluoromethyl group.

· "Substituted or unsubstituted alkenyl group"

Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (specific examples G4) include the following unsubstituted alkenyl groups (specific examples G4A), and substituted alkenyl groups (specific examples G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group".

A "substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have a substituent, and examples of substituted alkenyl groups (specific example group G4B). In addition, the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed herein are merely examples, and the "substituted alkenyl group" described herein also includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced with substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of specific example group G4B are further replaced with substituents.

· Unsubstituted alkenyl group (specific example group G4A):

Vinyl machine,

Announcement,

1-Viewten Diary,

2-Viewten Diary, and

3-View diary.

· Substituted alkenyl group (specific example group G4B):

1,3-Butanediene diary,

1-Methyl vinyl group,

1-Methylallyl group,

1,1-Dimethylallyl group,

2-Methylallyl group, and

1,2-Dimethylallyl group.

· "Substituted or unsubstituted alkyne group"

Specific examples of the “substituted or unsubstituted alkynyl group” described in this specification (specific examples G5) include the following unsubstituted alkynyl groups (specific examples G5A). (Here, the unsubstituted alkynyl group refers to the case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group.”) Hereinafter, when simply referred to as “alkynyl group”, both an “unsubstituted alkynyl group” and a “substituted alkynyl group” are included.

A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with a substituent.

· Unsubstituted alkyne group (specific example group G5A):

Etin Diary

· “Substituted or unsubstituted cycloalkyl group”

Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (specific examples G6) include the following unsubstituted cycloalkyl groups (specific examples G6A), and substituted cycloalkyl groups (specific examples G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referred to as a "cycloalkyl group", it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group".

A "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). In addition, the examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed herein are merely examples, and the "substituted cycloalkyl group" described in this specification also includes groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B are replaced with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced with a substituent.

· Unsubstituted cycloalkyl group (specific example G6A):

Cyclopropyl,

Cyclobutyl group,

Cyclopentyl group,

Cyclohexyl group,

1-Adamantyl group,

2-Adamantyl group,

1-Norbornyl group, and

2-Nobornyl group.

· Substituted cycloalkyl group (specific example G6B):

4-Methylcyclohexyl group.

· A group represented by "-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )"

Specific examples (specific example group G7) of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in this specification include:

-Si(G1)(G1)(G1),

-Si(G1)(G2)(G2),

-Si(G1)(G1)(G2),

-Si(G2)(G2)(G2),

-Si(G3)(G3)(G3), and

-Si(G6)(G6)(G6)

can be heard. Here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

- In Si(G1)(G1)(G1), plural G1s are identical or different.

- In Si(G1)(G2)(G2), multiple G2s are identical or different.

- In Si(G1)(G1)(G2), multiple G1s are identical or different.

- In Si(G2)(G2)(G2), multiple G2s are identical or different.

- In Si(G3)(G3)(G3), plural G3s are identical or different.

- In Si(G6)(G6)(G6), plural G6s are the same or different.

· Flags indicated by "-O-(R ₉₀₄ )"

Specific examples (specific example group G8) of the group represented by -O-(R ₉₀₄ ) described in this specification include:

-O(G1),

-O(G2),

-O(G3), and

-O(G6)

can be heard.

Here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

· Flags indicated by "-S-(R ₉₀₅ )"

Specific examples (specific group G9) of the group represented by -S-(R ₉₀₅ ) described in this specification include:

-S(G1),

-S(G2),

-S(G3), and

-S(G6)

can be heard.

Here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

· 「-N(R ₉₀₆ )(R ₉₀₇ )」

Specific examples (specific example group G10) of the group represented by -N(R ₉₀₆ )(R ₉₀₇ ) described in this specification include:

-N(G1)(G1),

-N(G2)(G2),

-N(G1)(G2),

-N(G3)(G3), and

-N(G6)(G6)

can be heard. Here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

- In N(G1)(G1), plural G1s are identical or different.

- In N(G2)(G2), plural G2s are identical or different.

- In N(G3)(G3), plural G3s are identical or different.

- In N(G6)(G6), plural G6s are identical or different from each other.

· "Halogen atom"

Specific examples of the “halogen atom” described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

· “Substituted or unsubstituted fluoroalkyl group”

The "substituted or unsubstituted fluoroalkyl group" described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. Meanwhile, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are substituted with a fluorine atom.

· “Substituted or unsubstituted haloalkyl group”

The "substituted or unsubstituted haloalkyl group" described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. Meanwhile, the "substituted haloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted haloalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with a halogen atom. A haloalkyl group is sometimes called a halogenated alkyl group.

· “Substituted or unsubstituted alkoxy group”

A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

· “Substituted or unsubstituted alkylthio group”

A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

· "Substituted or unsubstituted aryloxy group"

A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), wherein G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

· "Substituted or unsubstituted aryl thio group"

A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), wherein G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

· “Substituted or unsubstituted trialkylsilyl group”

A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

· “Substituted or unsubstituted aralkyl group”

A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which a hydrogen atom of the "alkyl group" is substituted with an "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification.

Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

The substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, Examples of the compounds include a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

In this specification, unless otherwise specified in this specification, a carbazolyl group is specifically any of the following groups.

[Chemical formula 9]

In this specification, unless otherwise specified in this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[Chemical Formula 10]

In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding position.

In this specification, unless otherwise specified in this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[Chemical Formula 11]

In the above general formulas (TEMP-34) to (TEMP-41), * indicates a bonding position.

The substituted or unsubstituted alkyl groups described in this specification are preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group, unless otherwise specified in this specification.

· "Substituted or unsubstituted arylene group"

The "substituted or unsubstituted arylene group" described herein, unless otherwise specified, is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

· “Substituted or unsubstituted divalent heterocyclic group”

The “substituted or unsubstituted divalent heterocyclic group” described herein, unless otherwise stated, is a divalent group derived from the “substituted or unsubstituted heterocyclic group” by removing one hydrogen atom on the heterocycle. Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include divalent groups derived from the “substituted or unsubstituted heterocyclic group” described in specific example group G2 by removing one hydrogen atom on the heterocycle.

· “Substituted or unsubstituted alkylene group”

The "substituted or unsubstituted alkylene group" described herein, unless otherwise specified, is a divalent group derived from the "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

The substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[Chemical Formula 12]

[Chemical Formula 13]

In the above general formulas (TEMP-42) to (TEMP-52), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-42) to (TEMP-52), * indicates a bonding position.

[Chemical Formula 14]

In the above general formulas (TEMP-53) to (TEMP-62), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

Formulas Q ₉ and Q ₁₀ may be combined with each other via a single bond to form a ring.

In the above general formulas (TEMP-53) to (TEMP-62), * indicates a bonding position.

[Chemical Formula 15]

In the above general formulas (TEMP-63) to (TEMP-68), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-63) to (TEMP-68), * indicates a bonding position.

The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group of the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

In the above general formulas (TEMP-69) to (TEMP-82), Q ₁ to Q ₉ are each independently a hydrogen atom or a substituent.

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

In the above general formulas (TEMP-83) to (TEMP-102), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

The above is a description of the “substituents described in this specification.”

· "When combined to form a ring"

In the present specification, when it is said that “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or are not combined with each other”, it means that “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring,” “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring,” and “one or more groups of two or more adjacent groups are not combined with each other.”

In the present specification, the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "cases of combining to form a ring") are described below. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring is described as an example.

[Chemical Formula 23]

For example, in the case where "one or more sets of two or more adjacent sets are combined with each other to form a ring" among R ₉₂₁ to R ₉₃₀ , the sets of two adjacent sets that form one set are: the sets of R ₉₂₁ and R ₉₂₂ , the sets of R ₉₂₂ and R ₉₂₃ , the sets of R ₉₂₃ and R ₉₂₄ , the sets of R ₉₂₄ and R ₉₃₀ , the sets of R ₉₃₀ and R ₉₂₅ , the sets of R ₉₂₅ and R ₉₂₆ , the sets of R ₉₂₆ and R ₉₂₇ , the sets of R ₉₂₇ and R ₉₂₈ , the sets of R ₉₂₈ and R ₉₂₉ , and the sets of R ₉₂₉ and R ₉₂₁ .

The above "1 group or more" means that two or more groups composed of two or more adjacent groups can form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ combine with each other to form ring Q _A , and at the same time R ₉₂₅ and R ₉₂₆ combine with each other to form ring Q _B , the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[Chemical Formula 24]

The case where "a group composed of two or more adjacent groups" forms a ring includes not only the case where a group composed of "two" adjacent groups combine as in the above-mentioned example, but also the case where a group composed of "three or more" adjacent groups combine. For example, it means the case where R ₉₂₁ and R ₉₂₂ combine with each other to form ring Q _A , furthermore R ₉₂₂ and R ₉₂₃ combine with each other to form ring Q _C , and a group composed of three adjacent groups (R ₉₂₁ , R ₉₂₂ and R ₉₂₃ ) combine with each other to form a ring and condense on an anthracene parent skeleton, and in this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q _A and ring Q _C share R ₉₂₂ .

[Chemical Formula 25]

The formed "monocyclic ring" or "fused ring" may be a saturated ring or an unsaturated ring as the structure of the formed ring alone. Even in the case where "a group of two adjacent rings" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), the formed ring Q _A and the ring Q _B are each a "monocyclic ring" or a "fused ring". In addition, in the general formula (TEMP-105), the formed ring Q _A and the ring Q _C are a "fused ring". The ring Q _A and the ring Q _C of the general formula (TEMP-105) become a fused ring by the condensation of the ring Q _A and the ring Q _C. If ring Q _A of the above general formula (TEMP-104) is a benzene ring, ring Q _A is a monocyclic ring. If ring Q _A of the above general formula (TEMP-104) is a naphthalene ring, ring Q _A is a condensed ring.

“Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle. “Saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocycle.

As a specific example of an aromatic hydrocarbon ring, a structure in which the group mentioned as a specific example in the specific example group G1 is terminated by a hydrogen atom can be mentioned.

As a specific example of an aromatic heterocycle, a structure in which an aromatic heterocycle group is terminated by a hydrogen atom as a specific example in the specific example group G2 can be mentioned.

As a specific example of an aliphatic hydrocarbon ring, a structure in which the group mentioned as a specific example in the specific example group G6 is terminated by a hydrogen atom can be mentioned.

"Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary elements. For example, the ring Q _A formed by R ₉₂₁ and R ₉₂₂ bonding to each other in the general formula (TEMP-104) above means a ring formed by the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and one or more arbitrary elements. As a specific example, in the case where ring Q _A is formed by R ₉₂₁ and R ₉₂₂ , when a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, "any element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in the present specification. In any element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated by a hydrogen atom or the like, and may be substituted by an "arbitrary substituent" described later. When including any element other than a carbon element, the ring formed is a heterocycle.

Unless otherwise specified in this specification, the “one or more arbitrary elements” constituting the monocyclic ring or condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.

Unless otherwise specified in this specification, among “single ring” and “condensed ring”, “single ring” is preferred.

Unless otherwise specified in this specification, among “saturated ring” and “unsaturated ring”, “unsaturated ring” is preferred.

Unless otherwise specified in this specification, “monocyclic” is preferably a benzene ring.

Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

In the case where “one or more groups consisting of two or more adjacent groups” are “combined with each other to form a substituted or unsubstituted monocyclic ring” or “combined with each other to form a substituted or unsubstituted condensed ring,” unless otherwise specified in the present specification, preferably, one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

In the case where the above "single ring" or "fused ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. Specific examples of the substituent in the case where the above "single ring" or "fused ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification."

In the case where the above "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. In the case where the above "monocyclic ring" or "condensed ring" has a substituent, a specific example of the substituent is the substituent described in the above-mentioned "substituent described in the present specification" section.

The above is an explanation of the case where "at least one group consisting of two or more adjacent groups combines with each other to form a substituted or unsubstituted monocyclic ring" and the case where "at least one group consisting of two or more adjacent groups combines with each other to form a substituted or unsubstituted condensed ring" ("when combined to form a ring").

· Substituents in cases where it is said to be “substituted or unsubstituted”

In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optionally substituted" in the present specification) is, for example,

Unsubstituted alkyl group having 1 to 50 carbon atoms,

Unsubstituted alkenyl group having 2 to 50 carbon atoms,

Unsubstituted alkyne group having 2 to 50 carbon atoms,

An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atom, cyano group, nitro group,

An unsubstituted aryl group having 6 to 50 ring carbon atoms, and

Heterocyclic group having 5 to 50 unsubstituted ring atoms

A group selected from the group consisting of,

Here, R ₉₀₁ to R ₉₀₇ are, independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a heterocyclic group having 5 to 50 substituted or unsubstituted ring atoms.

When two or more R _901s exist, two or more R _901s are identical to each other or different,

When two or more R _902s exist, two or more R _902s are identical to each other or different,

When two or more R _903s exist, two or more R _903s are identical to each other or different,

When two or more R _904s exist, two or more R _904s are identical or different from each other,

When two or more R _905s exist, two or more R _905s are identical to each other or different,

When two or more R _906s exist, two or more R _906s are identical or different from each other,

When two or more R _907s exist, two or more R _907s are identical or different from each other.

In one embodiment, the substituent in the case of "substituted or unsubstituted" is

Alkyl group having 1 to 50 carbon atoms,

An aryl group having 6 to 50 ring carbon atoms, and

Heterocyclic ring with 5 to 50 ring atoms

A group selected from the group consisting of .

In one embodiment, the substituent in the case of "substituted or unsubstituted" is

Alkyl group having 1 to 18 carbon atoms,

An aryl group having 6 to 18 ring carbon atoms, and

Heterocyclic ring with 5 to 18 ring atoms

A group selected from the group consisting of .

Specific examples of each of the above arbitrary substituents are specific examples of the substituents described in the above-mentioned “Substituents described in the present specification.”

Unless otherwise specified in the present specification, adjacent arbitrary substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring.

Unless otherwise specified in this specification, any substituent may additionally have a substituent. The substituent additionally possessed by the optional substituent is the same as the optional substituent described above.

In this specification, the numerical range indicated using “AA∼BB” means a range that includes the numerical value AA described before “AA∼BB” as the lower limit and the numerical value BB described after “AA∼BB” as the upper limit.

Hereinafter, the compound of the present invention is described.

A compound according to one aspect of the present invention is represented by the following formula (1A) or formula (1B).

However, in the following, the compound of the present invention represented by each formula included in formula (1A) and formula (1A) described below may be simply referred to as "compound (1A)", "inventive compound (1A)" or "first invention compound". In addition, the compound of the present invention represented by each formula included in formula (1B) and formula (1B) described below may be simply referred to as "compound (1B)", "inventive compound (1B)" or "second invention compound". In addition, the first and second invention compounds may be collectively referred to simply as "inventive compounds".

[Chemical Formula 26]

[Chemical formula 27]

Hereinafter, symbols in each formula included in formula (1A) and formula (1A) described below, and symbols in each formula included in formula (1B) and formula (1B) described below will be described. Note that the same symbols have the same meanings. In addition, in this specification, as shown below, in formula (1A), there are cases where the partial structure bonded to *a is referred to as “partial structure A.” In addition, in formula (1B), there are cases where the partial structure bonded to *a is referred to as “partial structure B.”

[Chemical formula 28]

<Compound (1A)>

In formula (1A), N ^* is a central nitrogen atom.

In formula (1A), one selected from Z ¹ and Z ² is a single bond bonding to *a, and preferably, Z ² is a single bond bonding to *a.

In other words, partial structure A in the above formula (1A) is represented by the following formula (1x-1) or (1x-2), and is preferably represented by the following formula (1x-2). When partial structure A is represented by the following formula (1x-2), compound (1A) is represented by the formula (1A-1) described below.

[Chemical Formula 29]

In formulas (1x-1) to (1x-2), *x represents a bonding position to *a. Details of Z ¹ and Z ² and other symbols are as explained below.

The above-mentioned Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ which are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group (aromatic heterocyclic group) having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ that are not single bonds may be hydrogen atoms.

Z ¹ and Z ² , R ^13A , and R ^14A , which are not single bonds, do not combine with each other to form a ring.

A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.

A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.

The unsubstituted alkyl group of the above substituted or unsubstituted alkyl group having 1 to 6 carbon atoms is, for example,

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group;

More preferably, it is a methyl group, an ethyl group, an isopropyl group or a t-butyl group;

Particularly preferred is a methyl group.

The unsubstituted aryl group of the above substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms is, for example,

A phenyl group, a biphenyl group, or a naphthyl group;

Preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

Particularly preferred is a phenyl group.

The above substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms is, for example,

Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, a benzisothiazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group (including a 9-carbazolyl group, or a 1-, 2-, 3- or 4-carbazolyl group; the same applies hereinafter);

Preferably, it is a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group,

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In formula (1A), R ^1A and R ^2A are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

R ^1A and R ^2A may be hydrogen atoms.

R ^1A and R ^2A may be combined with each other to form a ring or may not form a ring.

The unsubstituted alkyl group of the above substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, is, for example,

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group;

More preferably, it is a methyl group, an ethyl group, an isopropyl group or a t-butyl group;

Particularly preferred is a methyl group.

The unsubstituted aryl group of the above substituted or unsubstituted ring-forming carbon number 6 to 30, preferably 6 to 18, more preferably 6 to 12, is, for example,

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;

Preferably, it is a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

Particularly preferred is a phenyl group.

The heteroaryl group having 5 to 30, preferably 5 to 20, more preferably 5 to 13 ring atoms, substituted or unsubstituted, is, for example,

Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group, phenanthrolineyl group, phenazineyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, the same applies hereinafter), isobenzothiphenyl group (isobenzothienyl group, the same applies hereinafter), naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group (including a 9-carbazolyl group, or a 1-, 2-, 3- or 4-carbazolyl group. The same applies hereinafter.);

Preferably, it is a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group,

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In formula (1A), Y ¹ and Y ² are hydrogen atoms.

In formula (1A), L ¹ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and more preferably a substituted or unsubstituted phenylene group.

The above phenylene group is an o-phenylene group, an m-phenylene group, or a p-phenylene group, and a p-phenylene group is preferred.

The above biphenylene group is a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, a 3,2'-biphenylene group, a 3,3'-biphenylene group, or a 2,2'-biphenylene group, preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, or a 3,3'-biphenylene group, and more preferably a 4,4'-biphenylene group.

The above naphthylene group is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, or a 1,8-naphthylene group.

The substituent of L ¹ , which is an arylene group, is selected from an unsubstituted alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring-forming carbon atoms, and the substituents do not bond with each other and do not form a ring.

Details of the unsubstituted alkyl group having 1 to 6 carbon atoms as the substituent, and details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms as the substituent, are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In equation (1A), n1 is 0 or 1.

When n1 is 0, one selected from Z ¹ and Z ² is bonded to the central nitrogen atom N ^* .

In formula (1A), X ¹ is an oxygen atom, a sulfur atom, or =CR ^A R ^B , preferably an oxygen atom, or =CR ^A R ^B , more preferably an oxygen atom.

One selected from R ^A , R ^B , and R ²¹ to R ²⁸ is a single bond binding to *b1, or one selected from R ^A and R ^B is a divalent group binding to *b1, preferably, one selected from R ²² , R ²⁴ , R ²⁵ , R ²⁷ , R ^C , and R ^D is a single bond binding to *b1, or one selected from R ^A and R ^B is a divalent group binding to *b1.

When X ¹ = CR ^A R ^B , compound (1A) is represented by the following formula (1A-2).

The above-mentioned single bonds and the divalent groups bonded to the above-mentioned *b1, R ^A and R ^B , are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

The above single bond is not present, and R ^A and R ^B , which are not divalent groups bonded to the above *b1, may be hydrogen atoms.

Details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R ^A and R ^B are as described for R ^1A and R ^2A in formula (1A).

The divalent group bonding to the above *b1 represented by R ^A and R ^B is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.

As the alkylene group, arylene group, and heteroarylene group represented by R ^A and R ^B , divalent residues of each group described for the alkyl group, aryl group, and heteroaryl group represented by R ^A and R ^B can be exemplified, and the same applies to preferred ones.

R ^A and R ^B , which are not the above single bonds and are not divalent groups bonded to the above *b1, may or may not form a ring by bonding to each other.

The ring formed by R ^A and R ^B , which are not the single bond and are not the divalent group bonded to the above *b1, is a substituted or unsubstituted spiro ring. The spiro ring is a hydrocarbon ring or a heterocycle, and is selected from a monocyclic ring, a condensed ring, a bridged bicyclo ring, and a bridged tricyclo ring. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited thereto. * Indicates a bonding position of the fluorene skeleton to the benzene ring.

[Chemical formula 30]

In one embodiment, the partial structure bonded to L ² of compound (1A) is represented by one of the following formulas (1-a1) to (1-a5).

[Chemical Formula 31]

[Chemical formula 32]

In formulas (1-a1) to (1-a5), ** indicates the bonding position to L ² .

R ²¹ ∼R ²⁸ , and *b1 are as defined in the above formula (1A).

In formulas (1-a1) to (1-a5), R ^A1 to ^{R A3} , R ^A4 to R ^A8 , R ^B1 to R ^B3 , and R ^B4 to R ^B8 are hydrogen atoms.

The above R ²¹ to R ²⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ²¹ to R ²⁸ , which are not single bonds, may be hydrogen atoms.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ²¹ to R ²⁸ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formula (1A), when one selected from R ²¹ to ^{R 24} is a single bond bonding to *b1, R ²¹ to R ²⁴ that are not single bonds do not bond to each other to form a ring, and further, R ²⁵ to R ²⁸ may or may not bond to each other to form a ring.

When one selected from R ²⁵ to ^{R 28} is a single bond bonding to *b1, R ²⁵ to R ²⁸ that are not single bonds do not combine with each other to form a ring, and further, R ²¹ to R ²⁴ may or may not combine with each other to form a ring.

In formula (1A), L ² is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

Details of the substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms represented by L ² are as described for L ¹ in formula (1A).

In equation (1A), when L ¹ and L ² exist, they may be the same or different. Only one of L ¹ and L ² may exist (i.e., one of m or n may be 0 and the other may be 1), and both of L ¹ and L ² do not need to exist (i.e., m and n may be 0).

Preferably, the combination of “-(L ¹ ) _n1 -” and “-(L ² ) _n2 -” in the compound (1A) is represented by one of the combinations [k1] to [k4] shown below.

· [k1]: single bond/single bond

· [k2]: single bond/phenylene

· [k3]: Phenylene/single bond

· [k4]: Phenylene/Phenylene

In equation (1A), n2 is 0 or 1.

When n2 is 0, one selected from R ²¹ to R ²⁸ bonds to the central nitrogen atom N ^* .

In one sun, n1 and n2 are both 0, in another sun, n1 and n2 are both 1, in yet another sun, n1 is 0 and n2 is 1, and in yet another sun, n1 is 1 and n2 is 0.

In formula (1A), Ar ¹ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 ring carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and is more preferably a hydrogen atom.

Details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by Ar ¹ are as described for R ^1A and R ^2A in formula (1A).

In formula (1A), Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and more preferably a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

Details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹ are as described for R ^1A and R ^2A in formula (1A).

In formula (1A), m is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, preferably 0, 1, or 2, and more preferably 0 or 1. However, when Ar ¹ is a hydrogen atom, m is 0.

When m is 1 to 4, 1 to 4 selected from R ³¹ to R ³⁴ are single bonds bonding to *c. When m is 2 to 4, plural Ar ² may be the same or different.

In formula (1A), R ³¹ to R ³⁴ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ³¹ to R ³⁴ , which are not single bonds, may be hydrogen atoms.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ³¹ to R ³⁴ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formula (1A), Ar ¹ which is not a hydrogen atom and a pair of adjacent groups among R ³⁴ to R ²⁴ which are not hydrogen atoms may be combined with each other to form a ring or may not form a ring.

<Compound (1B)>

In formula (1B), N ^* is the central nitrogen atom.

In formula (1B), one selected from R ¹¹ to R ¹⁴ is a single bond bonding to *a, preferably one selected from R ¹² to R ¹⁴ is a single bond bonding to *a, more preferably, R ¹² or R ¹⁴ is a single bond bonding to *a, and even more preferably, R ¹² is a single bond bonding to *a.

In other words, the partial structure B in the above formula (1B) is represented by any one of the following formulas (1y-1) to (1y-4), preferably by any one of the following formulas (1y-2) to (1y-4), more preferably by the following formula (1y-2) or formula (1y-4), and even more preferably by the following formula (1y-2).

[Chemical formula 33]

In formulas (1y-1) to (1y-4), *y represents a bonding position to *a. Details of R ¹¹ to R ¹⁴ and other symbols are as explained below.

The above single bonds, R ¹¹ to R ¹⁴ , R ¹⁵ to R ¹⁸ , and R ⁷ to R ¹⁰ , are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ¹¹ to R ¹⁴ , R ¹⁵ to R ¹⁸ , and R ⁷ to R ¹⁰ , which are not single bonds, may be hydrogen atoms.

R ¹¹ to R ¹⁴ , which are not single bonds, do not combine with each other to form a ring.

A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.

A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms and the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹¹ to R ¹⁴ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formula (1B), R ^1B , R ^2B , R ^5B , and R ^6B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ^1B , R ^2B , R ^5B , and R ^6B may be hydrogen atoms.

R ^1B and R ^2B may be combined with each other to form a ring or may not form a ring.

R ^5B and R ^6B may be combined with each other to form a ring or may not form a ring.

Details ^of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by ^{R 1B} , R ^2B , R 5B , and R 6B are as described for R ^1A and R ^2A in formula (1A).

In formula (1B), L ³ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

Details of the above substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms are as described for L ¹ in formula (1A).

In equation (1B), n3 is 0 or 1.

When n3 is 0, Ar ³ binds to the central nitrogen atom N ^* .

In formula (1B), Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group represented by formula (2-1) below, or a group represented by formula (2-2) below, and is preferably an aryl group having 6 to 18 ring carbon atoms, a group represented by formula (2-1) below, or a group represented by formula (2-2) below, and is more preferably an aryl group having 6 to 12 ring carbon atoms.

[Chemical Formula 34]

In equation (2-1), ** indicates the binding position to L ³ .

In formula (2-1), X ³ is an oxygen atom or a sulfur atom, and is preferably an oxygen atom.

In formula (2-1), one selected from R ⁴¹ to R ⁴⁴ is a single bond bonding to *d, preferably one selected from R ⁴¹ , R ⁴² , and R ⁴⁴ is a single bond bonding to *d, more preferably R ⁴¹ or R ⁴⁴ is a single bond bonding to *d, and even more preferably, R ⁴⁴ is a single bond bonding to *d.

The above-mentioned R ⁴¹ to R ⁴⁴ , R ⁴⁵ to R ⁴⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ⁴¹ to R ⁴⁴ and R ⁴⁵ to R ⁴⁸ , which are not single bonds, may be hydrogen atoms.

Among the above-mentioned single bonds, a pair of adjacent groups among R ⁴¹ to ^{R 44} and a pair of adjacent groups among R ⁴⁵ to R ⁴⁸ may or may not be bonded to each other to form a ring.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ⁴¹ to R ⁴⁸ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In equation (2-2), ** indicates the binding position to L ³ .

In formula (2-2), R ⁴¹ to R ⁴⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ⁴¹ to ^{R 48} may be hydrogen atoms.

Among R ⁴¹ to R ⁴⁸ , a pair of adjacent groups may combine with each other to form a ring or may not form a ring.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ⁴¹ to R ⁴⁸ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

When Ar ³ is represented by the above formula (2-2), it is preferable that n3 is 1.

In formula (1B), L ⁴ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

Details of the substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms represented by L ⁴ are as described for L ¹ in formula (1A).

In equation (1B), n4 is 0 or 1.

When n4 is 0, Ar ⁴ binds to the central nitrogen atom N ^* .

In one sun, n1, n3, and n4 are all 0, in another sun, n1, n3, and n4 are all 1, in another sun, n1 and n3 are 0, and n4 is 1, in another sun, n1 and n4 are 0, n3 is 1, in another sun, n3 and n4 are 0, n1 is 1, in another sun, n1 is 0, n3 and n4 are 1, in another sun, n3 is 0, n1 and n4 are 1, and in another sun, n4 is 0, n1 and n3 are 1.

In formula (1B), Ar ⁴ is a group represented by formula (3-1) below, or a group represented by formula (3-2) below.

[Chemical Formula 35]

In equation (3-1), *** indicates the binding position to L ⁴ .

In formula (3-1), X ² is an oxygen atom, a sulfur atom, or =CR ^C R ^D , preferably an oxygen atom, or =CR ^C R ^D , more preferably an oxygen atom.

In formula (3-1), one selected from R ^21B ∼ R ^24B , R ^C , and R ^D is a single bond bonding to *b2, or one selected from R ^C and R ^D is a divalent group bonding to *b2.

When X ² is an oxygen atom or a sulfur atom, one selected from R ^21B to R ^28B is a single bond bonding to *b2, preferably one selected from R ^21B , R ^22B , R ^24B , R ^25B , R ^27B , and R ^28B is a single bond bonding to *b2, more preferably one selected from R ^21B , R ^24B , R ^25B , and R ^27B is a single bond bonding to *b2, and even more preferably R ^24B or R ^25B is a single bond bonding to *b2.

When X ² is =CR ^C R ^D , preferably, one selected from R ^21B ∼R ^23B , R ^26B ∼R ^28B , R ^C , and R ^D is a single bond binding to *b2, or one selected from R ^C and R ^D is a divalent group binding to *b2, more preferably, one selected from R ^23B , R ^26B , R ^C , or R ^D is a single bond binding to *b2, or one selected from R ^C and R ^D is a divalent group binding to *b2.

The above-mentioned R ^21B ∼R ^24B , R ^25B ∼R ^28B , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ^21B ∼ R ^24B and R ^25B ∼ R ^28B , which are not single bonds, may be hydrogen atoms.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ^21B ∼R ^28B are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ ∼R ¹⁸ , R ⁷ ∼R ¹⁰ in formula (1A).

In formula (3-1), when one selected from R ^21B to R ^24B is a single bond bonding to *b2, R ^21B to R ^24B that are not single bonds do not combine with each other to form a ring, and further, R ^25B to R ^28B may or may not combine with each other to form a ring.

When one selected from R ^25B to R ^28B is a single bond bonding to *b2, R ^25B to R ^28B that are not single bonds do not combine with each other to form a ring, and further, R ^21B to R ^24B may or may not combine with each other to form a ring.

In formula (3-1), R ^C and R ^D , which are not the single bond and are not the divalent group bonded to *b2, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and preferably, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

The above single bond is not present, and R ^C and R ^D which are not divalent groups bonding to the above *b2 may be hydrogen atoms.

R ^C and R ^D , which are not the above single bonds and are not divalent groups bonded to the above *b2, may or may not form a ring by bonding to each other.

Details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R ^C and R ^D are as described for R ^1A and R ^2A in formula (1A).

However, when one selected from R ^C and R ^D is an aryl group, the two do not combine to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R ^C and R ^D are combined. In other words, R ^C and R ^D do not combine with each other to form a structure represented by the following formula. In the formula below, *w represents a bonding position to L4. In addition, in the formula below, R is omitted for simplicity.

[Chemical formula 36]

In formula (3-1), when X ² is an oxygen atom or a sulfur atom, n4 is 1.

In equation (3-2), *** indicates the binding position to L ⁴ .

In formula (3-2), R ^21B to R ^28B are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ^21B ∼ ^{R 28B} may be hydrogen atoms.

A pair of adjacent groups among R ^21B ∼ ^{R 24B} and a pair of adjacent groups among R ^25B ∼ R ^28B may or may not form a ring by combining with each other.

Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R ²¹ to R ²⁸ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formula (3-2), *N ^* , L ¹ , n1, R ⁷ to R ¹⁰ , and R ¹⁵ to R ¹⁸ have the same meanings as defined in formula (1A).

When Ar ⁴ is represented by the above formula (3-2), it is preferable that n4 is 1.

In equation (1B), when L ¹ , L ² , and L ³ exist, the three may be the same or different, and two of the three may be the same and the other one may be different.

In equation (1B), only two of L ¹ , L ² , and L ³ may exist (i.e., two of n1, n3, and n4 may be 1 and the other may be 0), and in this case, the existing quanta may be the same or different from each other.

In equation (1B), only one of L ¹ , L ² , and L ³ may exist (i.e., two of n1, n3, and n4 may be 0 and the other may be 1), and all of L ¹ to L ³ may not exist (i.e., n1, n3, and n4 may be 0).

Preferably, the combination of “-(L ¹ ) _n1 -”, “-(L ³ ) _n3 -” and “-(L ⁴ ) _n4 -” in the compound (1A) is represented by one of the combinations [k11] to [k18] shown below.

· [k11]: single bond/single bond/single bond

· [k12]: single bond/single bond/phenylene

· [k13]: single bond/phenylene/single bond

· [k14]: Phenylene/single bond/single bond

· [k15]: single bond/phenylene/phenylene

· [k16]: Phenylene/single bond/phenylene

· [k17]: Phenylene/Phenylene/Single bond

· [k18]: Phenylene/Phenylene/Phenylene

In a suitable embodiment, the compound (1A) is represented by the following formula (1A-1).

[Chemical formula 37]

In formula (1A-1), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ to R ¹⁰ , Z ¹ , R ^13A , R ^14A , R ¹⁵ to R ¹⁸ , R ²¹ to R ²⁸ , X ¹ , R ³¹ to R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *b1, *c, m, n1 , and n2 are as defined in the above formula (1A).

In one embodiment, the compound (1A) is represented by the following formula (1A-2).

[Chemical formula 38]

In formula (1A-2), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ ∼R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ ∼R ¹⁸ , R ²¹ ∼R ²⁸ , R ^A , R ^B , R ³¹ ∼R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1 , and n2 are as defined in the above formula (1A).

In one embodiment, in formula (1A-2), one of R ²¹ , R ²² , R ²⁴ , R ²⁵ , R ²⁷ , and R ²⁸ is a single bond bonding to *b1, in another embodiment, one of R ²¹ , R ²⁴ , R ²⁵ , and R ²⁸ is a single bond bonding to *b1, and in still another embodiment, R ²⁴ or R ²⁸ is a single bond bonding to *b1.

In one embodiment, compound (1A) is represented by the above formula (1A), formula (1A-1), or formula (1A-2), and when n1 is 1, L ¹ is a phenylene group, and when n2 is 1, L ² is a phenylene group.

In one embodiment, the compound (1A) is represented by any one of the following formulae (1A-3) to (1A-5).

[Chemical Formula 39]

[Chemical formula 40]

[Chemical Formula 41]

In formulas (1A-3) and (1A-5), R ⁵¹ to R ⁵⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms. However, one selected from R ⁵¹ to R ⁵⁵ is a single bond bonding to *d. All of R ⁵¹ to R ⁵⁵ that are not single bonds bonding to *d may be hydrogen atoms.

Among the above-mentioned single bonds, adjacent groups R ⁵¹ to R ⁵⁵ do not bond with each other and do not form a ring.

In formulas (1A-4) and (1A-5), R ⁶¹ to R ⁶⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms. However, one selected from R ⁶¹ to R ⁶⁵ is a single bond bonding to *e. All of R ⁶¹ to R ⁶⁵ that are not single bonds bonding to *e may be hydrogen atoms.

Among the above-mentioned single bonds, adjacent groups R ⁶¹ to R ⁶⁵ do not bond with each other and do not form a ring.

The unsubstituted alkyl group having 1 to 6 carbon atoms, and the unsubstituted aryl group having 6 to 12 ring carbon atoms, represented by R ⁵¹ to ^{R 55} and R ⁶¹ to R ⁶⁵ , are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formulas (1A-3) to (1A-5), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ to R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ to R ¹⁸ , R ²¹ to R ²⁸ , X ¹ , R ³¹ to R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1 , and n2 are as defined in the above formula (1A).

In one embodiment, the compound (1A) is represented by any one of the following formulae (1A-6) to (1A-8).

[Chemical formula 42]

[Chemical Formula 43]

[Chemical Formula 44]

In formulas (1A-6) to (1A-8), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ to R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ to R ¹⁸ , R ²¹ to R ²⁸ , X ¹ , R ³¹ to R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1, and n2 are as defined in the above formula (1A).

In one embodiment, the compound (1A) is represented by any one of the formulas (1A) and (1A-1) to (1A-8),

· Ar ¹ is a hydrogen atom, and m is 0, or

· Ar ¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 0, or

· Ar ¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 1.

In one embodiment, the compound (1A) is represented by any one of the formulas (1A) and (1A-1) to (1A-8), and Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

In one embodiment, the compound (1B) is represented by the following formula (1B-1).

[Chemical Formula 45]

In formula (1B-1), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ ∼R ¹⁰ , R ¹¹ , R ¹³ ∼R ¹⁸ , N ^* , Ar ³ , Ar ⁴ , L ¹ , L ³ , L ⁴ , n1 , n3 , and n4 are as defined in the formula (1B).

In one embodiment, the compound (1B) is represented by the following formula (1B-2).

[Chemical Formula 46]

In formula (1B-2), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ ∼R ¹⁰ , R ¹¹ ∼R ¹⁸ , R ^21B ∼R ^28B , R ^C , R ^D , N ^* , Ar ³ , L ¹ , L ³ , L ⁴ , *a, *b2, n1, n3, and n4 are as defined in the above formula (1B).

In the sun, in formula (1B-2), Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In one embodiment, a compound represented by any one of the above formulas (1B), (1B-1), and (1B-2), wherein when n1 is 1, L ¹ is a phenylene group, when n3 is 1, L ³ is a phenylene group, and when n4 is 1, L ⁴ is a phenylene group.

In one embodiment, the compound (1B) is represented by any one of the following formulae (1B-3) to (1B-9).

[Chemical formula 47]

[Chemical formula 48]

[Chemical Formula 49]

[Chemical formula 50]

[Chemical Formula 51]

[Chemical formula 52]

[Chemical formula 53]

In formulas (1B-3), (1B-6), (1B-7), and (1B-9), R ⁵¹ to R ⁵⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms. However, one selected from R ⁵¹ to R ⁵⁵ is a single bond bonding to *d. All of R ⁵¹ to R ⁵⁵ that are not single bonds bonding to *d may be hydrogen atoms.

Among the above-mentioned single bonds, adjacent groups R ⁵¹ to R ⁵⁵ do not bond with each other and do not form a ring.

In formulas (1B-4), (1B-6), (1B-8), and (1B-9), R ⁷¹ to R ⁷⁵ each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms. However, one selected from R ⁷¹ to R ⁷⁵ is a single bond bonding to *f. All of R ⁷¹ to R ⁷⁵ that are not single bonds bonding to *f may be hydrogen atoms.

Among the above-mentioned single bonds, adjacent groups R ⁷¹ to R ⁷⁵ do not bond with each other and do not form a ring.

In formulas (1B-5), and formulas (1B-7) to (1B-9), R ⁸¹ to R ⁸⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms. However, one selected from R ⁸¹ to R ⁸⁵ is a single bond bonding to *g. All of R ⁸¹ to R ⁸⁵ that are not single bonds bonding to *g may be hydrogen atoms.

Among the above-mentioned single bonds, adjacent groups R ⁸¹ to R ⁸⁵ do not bond with each other and do not form a ring.

The unsubstituted alkyl group having 1 to 6 carbon atoms and the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ⁵¹ to R ⁵⁵ , R ⁷¹ to R ⁷⁵ , and R ⁸¹ to R ⁸⁵ are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

In formulas (1B-3) to (1B-9), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ to R ¹⁰ , R ¹¹ to R ¹⁸ , N ^* , Ar ³ , Ar ⁴ , L ¹ , L ³ , L ⁴ , *a, n1, n3, and n4 are as defined in the above formula (1B).

In one embodiment, the compound (1B) is represented by any one of the formulas (1B), (1B-1), and (1B-3) to (1B-9),

Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

Ar ⁴ is a group represented by the above formula (3-1), and further, X ² is an oxygen atom or a sulfur atom, or a group represented by the above formula (3-2).

In one embodiment, the compound (1B) is represented by the formula (1B),

Ar ³ is a group represented by the above formula (2-1) or formula (2-2),

Ar ⁴ is a group represented by the above formula (3-1), and further, X ² is an oxygen atom or a sulfur atom, or a group represented by the above formula (3-2).

In one embodiment, the compound (1B) is represented by any one of the formulas (1B) and (1B-1) to (1B-9), and Ar ³ is represented by any one of the formulas (2A) to (2F) below.

[Chemical formula 54]

In formula (2A), *21 is the binding position to L ³ .

In formula (2A), one selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23.

The above-mentioned R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms.

All of R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹⁰¹ to R ¹⁰⁵ that are not the above single bonds do not bond to each other and do not form a ring.

Two adjacent groups selected from R ¹⁰⁶ to R ¹¹⁰ that are not the above single bonds do not bond to each other and do not form a ring.

In formula (2A), R ¹¹¹ to R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ¹¹¹ to ^{R 115} may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and details of the above substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹¹¹ to R ¹¹⁵ do not bind to each other and do not form a ring.

In equation (2A), m11 is 0, 1, or 2, and n11 is 0 or 1. The case where m11 is 2 and n11 is 0 is excluded.

When m11=0, n11=0, *23 represents *21.

When m11=0, n11=1, *22 represents *21.

When m11=1, n11=0, *23 represents *22.

When Ar ³ is represented by formula (2A), it is preferable that n3 is 0.

In addition, when Ar ³ is represented by formula (2A) and m11 is 0 and n11 is 1, it is preferable that R ¹⁰⁶ to R ¹¹⁰ are a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

Furthermore, when Ar ³ is represented by formula (2A), m11 is 1 and n11 is 0, it is preferable that R ¹⁰¹ to R ¹⁰⁵ , which is not a single bond bonding to *22, is a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

The group represented by formula (2A) is preferably represented by the following formula. In the formula below, R is omitted for simplicity.

[Chemical formula 55]

[Chemical formula 56]

In formula (2B), *24 is the binding position to L ³ .

In formula (2B), one selected from R ¹²¹ to R ¹²⁸ is a single bond bonding to *25.

The above R ¹²¹ to R ¹²⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms.

All of R ¹¹¹ to ^{R 115} may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹²¹ to R ¹²⁸ that are not the above single bonds do not bond to each other and do not form a ring.

[Chemical formula 57]

In formula (2C), *26 is the binding position to L ³ .

In formula (2C), one selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonding to *27.

The above R ¹³¹ to R ¹⁴⁰ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms.

All of R ¹³¹ to R ¹⁴⁰ , which are not single bonds, may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds do not form a ring without being bonded to each other.

[Chemical formula 58]

In formula (2D), *28 is the binding position to L ³ .

In equation (2D), n12 is 0 or 1.

When n12 is 0, one selected from R ¹⁴¹ - R ¹⁴⁸ , R ^E , and R ^F is a single bond binding to *29, or one selected from R ^E and R ^F is a divalent group binding to *29.

When n12 is 1, one of R ¹⁴¹ and R ¹⁴² , R ¹⁴² and R ¹⁴³ , or R ¹⁴³ and R ¹⁴⁴ is a single bond bonding to *h, the other is a single bond bonding to *i, and one selected from R ¹⁴¹ to R ¹⁴⁴ , R ¹⁴⁵ to R ¹⁴⁸ , R ²⁰⁰ to R ²⁰³ , R ^E , and R ^F is a single bond bonding to *29, or one selected from R ^E and R ^F is a divalent group bonding to *29.

In formula (2D), R ¹⁴¹ to R ¹⁴⁸ , which are not single bonds, and R ²⁰⁰ to R ²⁰³ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring carbon atoms, and preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

All of R ¹⁴¹ to ^{R 148} , which are not single bonds, and all of R ²⁰⁰ to R ²⁰³ , which are not single bonds, may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and details of the above substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹⁴¹ to ^{R 148} that are not the above single bonds and R ²⁰⁰ to R ²⁰³ that are not the above single bonds do not bond to each other and do not form a ring.

In the formula (2D), R ^E and R ^F which are not the single bond and are not the divalent group bonded to *29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and preferably, each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and more preferably, a hydrogen atom.

The above single bond is not present, and R ^E and R ^F , which are not divalent groups bonded to the above *29, may be hydrogen atoms.

Details of the above substituted or unsubstituted alkyl group having 1 to 30 carbon atoms are as described for R ^1A and R ^2A in formula (1A).

Details of the above substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and details of the above substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

R ^E and R ^F , which are not the above single bonds and are not divalent groups bonded to *29, may or may not form a ring by bonding to each other.

However, when one selected from R ^E and R ^F is an aryl group, the two do not combine to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R ^E and R ^F are combined. In other words, R ^E and R ^F do not combine with each other to form a structure represented by the following formula. In the formula below, *w2 represents a bonding position to L3. In addition, in the formula below, R is omitted for simplicity.

[Chemical formula 59]

[Chemical formula 60]

In formula (2E), *30 is the binding position to L ³ .

In formula (2E), one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *31, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *32.

The above R ¹⁵¹ to R ¹⁵⁵ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, and are preferably hydrogen atoms.

All of R ¹⁵¹ to R ¹⁵⁵ , which are not single bonds, may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Two adjacent groups selected from R ¹⁵¹ to R ¹⁵⁵ that are not single bonds do not form a ring without being bonded to each other.

In formula (2E), R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, and are preferably hydrogen atoms.

All of R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

At least two adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ that are not hydrogen atoms may be combined with each other to form one or more unsubstituted benzene rings, or may not be combined with each other to form a ring.

At least two adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus do not form a ring.

Formula (2E) includes a group represented by formulas (2E-1) to (2E-5) below, and formula (2E-1), (2E-2), or (2E-5) is preferable.

[Chemical formula 61]

[Chemical formula 62]

In formula (2F), *32 is the binding position to L ³ .

In formula (2F), one selected from R ¹⁸¹ to R ¹⁹² is a single bond bonding to *33.

The above R ¹⁸¹ to R ¹⁹² , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, and are preferably hydrogen atoms.

All of R ¹⁸¹ to R ¹⁹² , which are not single bonds, may be hydrogen atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R ^1A and R ^2A in formula (1A), except that the number of carbon atoms is 1 to 10.

Details of the above substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as described for Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ in formula (1A).

Two adjacent groups selected from R ¹⁸¹ to R ¹⁹² that are not the above single bonds do not bond to each other and do not form a ring.

In one embodiment, the inventive compound is represented by any one of the formulas (1A), (1A-1), and (1A-3) to (1A-5), and X ¹ is an oxygen atom.

In one embodiment, the inventive compound is represented by any one of the formulas (1B), (1B-1), and (1B-3) to (1B-9), and X ² is an oxygen atom.

In one embodiment, the inventive compound is represented by any one of the formulas (1B), (1B-1), and (1B-3) to (1B-9), and X ³ is an oxygen atom.

In one embodiment, R ^1A , R ^2A , R ⁷ ∼ R ¹⁰ , R ^13A , R ^14A , R ¹⁵ ∼ R ¹⁸ , Z ¹ and Z ² which are not the single bonds, R ³¹ ∼ R ³⁴ which are not the single bonds, Ar ¹ , R ²¹ ∼ R ²⁸ which are not the single bonds, R ^A and R ^B which are not the divalent group bonding to *b1, R ^1B , R ^2B , R ^5B , R ^6B which are not the single bonds, R ¹¹ ∼ R ¹⁴ which are not the single bonds, R ⁴¹ ∼ R ⁴⁴ , R ⁴⁵ ∼ R ⁴⁸ which are not the single bonds, R ^21B ∼ R ^28B which are not the single bonds, R ^C and R which are not the divalent group bonding to *b2 ^D , R ¹⁰¹ to R ¹⁰⁵ which are not the single bond, R ¹⁰⁶ to R ¹¹⁰ , R ¹¹¹ to R ¹¹⁵ which are not the single bond, R ¹²¹ to R ¹²⁸ which are not the single bond, R ¹³¹ to R ¹⁴⁰ which are not the single bond, R ¹⁴¹ to R ¹⁴⁸ which are not the single bond, R ²⁰⁰ to R ²⁰³ which are not the single bond, R ¹⁵¹ to R ¹⁵⁵ , R ¹⁶¹ to R ¹⁶⁵ , R ¹⁷¹ to R ¹⁷⁵ which are not the single bond, and R ¹⁸¹ to R ¹⁹² which are not the single bond are all hydrogen atoms.

In one embodiment, the compound represented by formula (1A) or formula (1B) contains at least one deuterium atom.

The deuterium atoms included in compound (1A) and compound (1B) will be described in detail later.

In one embodiment of compound (1A) and compound (1B), at least one of the following (1) to (9) is a deuterium atom.

(1) R ^1A , R ^2A , Y ¹ , Y ² , R ^{7∼R 10} , ^Z 1, Z ² , R ^13A , R ^14A , R ^{15∼R 18} , R ^{21∼R 28} , R ^{31∼R 34} , R ^A , R ^B , Ar ¹ , R ^{51∼R 55} , R ^{61∼R 65} , R ^1B , R ^2B , R ^5B , R ^6B , R ^{11∼R 14} , R ^{41∼R 48} , R ^{21B∼R 28B} , R ^C , R ^D , R ^{71∼R 75} , R ^{81∼R 85} , R ¹⁰¹ ∼R ¹⁰⁵ , R Hydrogen atoms represented ^{by 106} ∼R ¹¹⁰ , R ¹¹¹ ∼R ¹¹⁵ , R ¹²¹ ∼R ¹²⁸ , R ¹³¹ ∼R ¹⁴⁰ , R ¹⁴¹ ∼R ¹⁴⁸ , R ²⁰⁰ ∼R ²⁰³ , R ^E , R ^F , R ¹⁵¹ ∼R ¹⁵⁵ , R ¹⁶¹ ∼R ¹⁶⁵ , R ¹⁷¹ ∼R ¹⁷⁵ , and R ¹⁸¹ ∼R ¹⁹² ;

(2) R ^1A , R ^2A , R ^{7∼R 10} , Z ¹ , Z 2, R ^13A , R ^14A , R ^{15∼R 18} , R ^{21∼R 28} , R ^{31∼R 34} , R ^A , R ^B , ^{R 51∼R 55 , R 61∼R 65} , R ^1B , R ^2B , R ^5B , R ^6B , R ^{11∼R 14} , R ^{41∼R 48} , R ^{21B∼R 28B} , R ^C , R ^D , R ^{71∼R 75} , R ^{81∼R 85} , R ^{101∼R 105} , R ^{106∼R 110} ,R A hydrogen atom directly connected ^{to an alkyl group represented by R 111 ∼R 115 , R 121 ∼R 128 , R 131 ∼R 140 , R 141} ∼R ¹⁴⁸ , R ²⁰⁰ ∼R ²⁰³ , R ^E , R ^F , R ¹⁵¹ ∼R ¹⁵⁵ , R ¹⁶¹ ∼R 165 , R 171 ∼R ¹⁷⁵ , and R ¹⁸¹ ∼R ¹⁹² ;

(3) R ^1A , R ^2A , R ⁷ ∼R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ⁷ ∼R ¹⁰ , R ¹⁵ ∼R ¹⁸ , R ²¹ ∼R ²⁸ , R ³¹ ∼R ³⁴ , Ar ¹ , Ar ² , R ^A , R ^B , R ^{51∼R 55} , R ^{61∼R 65} , R ^1B , R ^2B , R ^5B , R ^6B , R ^{11∼R 14} , R ^{41∼R 48} , R ^{21B∼R 28B} , R ^C , R ^D , R ^{71∼R 75} , R ^{81∼R 85} , R ¹⁰¹ ~R A hydrogen atom ^{directly attached to the aryl group represented by R 105 , R 106 ∼R 110 , R 111 ∼R 115 , R 121 ∼R 128 ,} R ¹³¹ ∼R ¹⁴⁰ , R ¹⁴¹ ∼R ¹⁴⁸ , R 200 ∼R 203 , R ^E , R ^F , R ¹⁵¹ ∼R ¹⁵⁵ , and R ¹⁸¹ ∼R ¹⁹² ;

(4) ^a hydrogen atom directly connected to a heteroaryl group represented by R ^1A , R ^2A , R ⁷ ∼ R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ ∼ R ¹⁸ , R ²¹ ∼ R 28 , R ³¹ ∼ ^{R 34} , Ar ¹ , R ^A , R ^B , R ^1B , R ^2B , R ^{5B , R 6B , R 41 ∼ R 48 , R 21B ∼ R 28B ,} R ^C , R ^D , R ¹¹¹ ∼ R 115 , R ¹⁴¹ ∼ R ¹⁴⁸ , R 200 ∼ R ²⁰³ , R ^E , and R ^F ;

(5) R ^1A , R ^2A , R ^{7∼R 10} , Z ¹ , Z 2, R ^13A , R ^14A , R ^{15∼R 18} , R ^{21∼R 28} , R ^{31∼R 34} , R ^A , R ^B , R ^1B , R ^2B , R ^{5B ,} R ^6B , R ¹¹ to R ¹⁴ , R ⁴¹ to ^{R 48} , R ^21B to R ^28B , R ^C , R ^D , R ¹¹¹ to R ¹¹⁵ , R ¹²¹ to R ¹²⁸ , R ¹³¹ to R ¹⁴⁰ , R ¹⁴¹ to R ¹⁴⁸ , R ²⁰⁰ to R ²⁰³ , R ^E , R ^F , and A hydrogen atom directly connected to a substituent of the alkyl group represented by R ¹⁸¹ - R ¹⁹² ;

(6) R ^1A , R ^2A , R ^{7∼R 10} , Z ¹ , Z ² , R ^{13A, R 14A ,} R ^{15∼R 18} , R ^{21∼R 28} , R ^{31∼R 34} , Ar ¹ , Ar ² , R ^A , R ^B , R ^1B , R ^2B , R ^5B , R ^6B , R ^{11∼R 14} , R ^{41∼R 48} , R ^{21B∼R 28B} , R ^C , R ^D , R ^{111∼R 115} , R ^{121∼R 128} , R ^{131∼R 140} , R ^{141∼R 148} , R ²⁰⁰ ~R ²⁰³ , R ^E , R ^F , and a hydrogen atom directly connected to a substituent of the aryl group represented by R ¹⁸¹ to R ¹⁹² ;

(7) ^{A hydrogen atom directly connected to a substituent of a heteroaryl group represented by R 1A , R 2A , R 7 ∼ R 10 , Z 1 , Z 2 , R 13A , R 14A , R 15 ∼ R 18 , R 21} ∼ R ²⁸ , R ³¹ ∼ R 34 , Ar ¹ , R ^A , R ^B , ^{R 1B , R 2B , R 5B , R 6B ,} R ⁴¹ ∼ R ⁴⁸ , R ^21B ∼ R ^28B , R ^C , R ^D , R ¹¹¹ ∼ R ¹¹⁵ , R ¹⁴¹ ∼ R 148 , R 200 ∼ R ²⁰³ , R ^E , and R ^F ;

(8) a hydrogen atom directly connected to an arylene group represented by L ¹ to L ⁴ ; and

(9) A hydrogen atom directly connected to a substituent of an arylene group represented by L ¹ to ^{L 4} .

As described above, the “hydrogen atom” used in this specification includes a light hydrogen atom, a deuterium atom, and a tritium atom. The first or second invention compound may contain a naturally occurring deuterium atom.

In addition, deuterium atoms may be intentionally introduced into the first or second invention compound by using a deuterated compound in part or in whole of the raw material compound.

The deuteration rate of the first or second invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain ratio of naturally occurring hydrogen isotopes may be included. Therefore, the aspect of the deuteration rate of the invention compound shown below includes a ratio that takes into account a trace amount of naturally occurring isotopes, relative to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula.

The deuteration rate of the first or second invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more.

The first or second inventive compound may be a deuterium compound in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the inventive compound is 100%).

The first or second invention compound may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, still more preferably 50% or more, and further less than 100%.

In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the first or second invention compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, and further preferably 100% or less.

The details of the substituent (any substituent) in the case of “substituted or unsubstituted” included in the definition of each formula above are as described in “Substituent in the case of “substituted or unsubstituted””.

The first or second invention compound can be easily manufactured by a person skilled in the art by referring to the synthetic examples described below and known synthetic methods.

Specific examples of the first or second invention compounds are shown below, but are not limited to the following exemplary compounds.

In the following specific examples, D represents a deuterium atom.

[Chemical formula 63]

[Chemical formula 64]

[Chemical formula 65]

[Chemical formula 66]

[Chemical formula 67]

[Chemical formula 68]

[Chemical formula 69]

[Chemical formula 70]

[Chemical formula 71]

[Chemical formula 72]

[Chemical formula 73]

[Chemical formula 74]

[Chemical formula 75]

[Chemical formula 76]

[Chemical formula 77]

[Chemical formula 78]

[Chemical formula 79]

[Chemical formula 80]

[Chemical formula 81]

[Chemical formula 82]

[Chemical formula 83]

[Chemical formula 84]

[Chemical formula 85]

[Chemical formula 86]

[Chemical formula 87]

[Chemical formula 88]

[Chemical formula 89]

[Chemical formula 90]

[Chemical formula 91]

[Chemical formula 92]

[Chemical formula 93]

[Chemical formula 94]

[Chemical formula 95]

[Chemical formula 96]

[Chemical formula 97]

[Chemical formula 98]

[Chemical formula 99]

[Chemical Formula 100]

[Chemical Formula 101]

[Chemical Formula 102]

[Chemical Formula 103]

[Chemical Formula 104]

[Chemical Formula 105]

[Chemical formula 106]

[Chemical Formula 107]

[Chemical Formula 108]

[Chemical Formula 109]

[Chemical formula 110]

[Chemical formula 111]

[Chemical formula 112]

[Chemical formula 113]

[Chemical Formula 114]

[Chemical Formula 115]

[Chemical formula 116]

[Chemical formula 117]

[Chemical formula 118]

[Chemical Formula 119]

[Chemical formula 120]

[Chemical Formula 121]

[Chemical formula 122]

[Chemical formula 123]

[Chemical formula 124]

[Chemical Formula 125]

[Chemical formula 126]

[Chemical formula 127]

[Chemical formula 128]

[Chemical Formula 129]

[Chemical formula 130]

[Chemical Formula 131]

[Chemical formula 132]

Materials for organic EL devices

An organic EL device material according to one embodiment of the present invention contains a first or second invention compound. The content of the first or second invention compound in the organic EL device material is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), still more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%). An organic EL device material according to one embodiment of the present invention is useful for the production of an organic EL device.

In one aspect of the present invention, it is preferable that the first or second invention compound is a hole transport layer material.

In one aspect of the present invention, it is preferable that the material for an organic EL device further comprises a hydrogen conformer of the first or second invention compound. The hydrogen conformer is a compound in which all hydrogen atoms in the first or second invention compound are hydrogen atoms.

The mixing molar ratio of the first or second invention compound and the hydrophobic body of the first or second invention compound (invention compound:hydrophobic body) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, still more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

A material for an organic electroluminescent device according to one aspect of the present invention is a hole transport layer material.

The content of the inventive compound in the material for an organic electroluminescence device is preferably 1 mass% or more (including 100%), more preferably 10 mass% or more (including 100%), further preferably 50 mass% or more (including 100%), still more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%).

Organic EL devices

An organic EL device according to one aspect of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the invention compound.

Examples of organic layers including the inventive compound include, but are not limited to, a hole transport band (a hole injection layer, a hole transport layer, an electron blocking layer, an exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a space layer, an electron transport band (an electron injection layer, an electron transport layer, a hole blocking layer, etc.) provided between the cathode and the light-emitting layer, and the like. The inventive compound is preferably used as a material for a hole transport band or a light-emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for a hole transport band, more preferably as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably as a material for a hole injection layer or a hole transport layer.

The organic EL device, which is one embodiment of the present invention, may be a single-color light-emitting device of a fluorescent or phosphorescent type, a white light-emitting device of a fluorescent/phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units. Among these, the device is preferably a fluorescent light-emitting type. Here, the "light-emitting unit" means the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and that emits light by the recombination of injected holes and electrons.

For example, as a representative device configuration of a simple organic EL device, the following device configuration can be mentioned.

(1) Anode/Light-emitting unit/Cathode

In addition, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent light-emitting layers or fluorescent light-emitting layers, and in that case, a space layer may be provided between each light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer configuration of a simple type light-emitting unit is shown below. The layers in parentheses are arbitrary.

(a) (hole injection layer/)hole transport layer/fluorescent emitting layer/electron transport layer(/electron injection layer)

(b) (hole injection layer/) hole transport layer/first fluorescent emitting layer/second fluorescent emitting layer/electron transport layer (/electron injection layer)

(c) (hole injection layer/) hole transport layer/phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)

(d) (hole injection layer/) hole transport layer/first phosphorescent emitting layer/second phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)

(e) (hole injection layer/) hole transport layer/phosphorescent emitting layer/space layer/first fluorescent emitting layer/second fluorescent emitting layer/electron transport layer (/electron injection layer)

(f) (hole injection layer/)hole transport layer/electron blocking layer/fluorescent emitting layer/electron transport layer(/electron injection layer)

(g) (hole injection layer/) hole transport layer/exciton blocking layer/fluorescent emitting layer/electron transport layer(/electron injection layer)

(h) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent emitting layer/electron transport layer (/electron injection layer)

(i) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)

(j) (hole injection layer/)hole transport layer/fluorescent emitting layer/hole blocking layer/electron transport layer (/electron injection layer)

(k) (hole injection layer/)hole transport layer/fluorescent emitting layer/exciton blocking layer/electron transport layer(/electron injection layer)

Each of the above phosphorescent or fluorescent emitting layers can exhibit different emission colors. Specifically, in the above emitting unit (d), a layer configuration such as (hole injection layer/) hole transport layer/first phosphorescent emitting layer (red emission)/second phosphorescent emitting layer (green emission)/space layer/fluorescent emitting layer (blue emission)/electron transport layer can be exemplified.

Meanwhile, an electron blocking layer may be provided appropriately between each light-emitting layer and the hole transport layer or space layer. In addition, a hole blocking layer may be provided appropriately between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes are confined within the light-emitting layer, the probability of charge recombination in the light-emitting layer is increased, and the luminescence efficiency can be improved.

As representative device configurations of tandem-type organic EL devices, the following device configurations can be mentioned.

(2) Anode/First light emitting unit/Intermediate layer/Second light emitting unit/Cathode

Here, the first light emitting unit and the second light emitting unit can be independently selected from the light emitting units described above, for example.

The above intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generating layer, an electron extracting layer, a connection layer, or an intermediate insulating layer, and can utilize a known material composition that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device according to one embodiment of the present invention. The organic EL device (1) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (10) arranged between the anode (3) and the cathode (4). The light-emitting unit (10) has a light-emitting layer (5). A hole transport band (6) (a hole injection layer, a hole transport layer, etc.) is arranged between the light-emitting layer (5) and the anode (3), and an electron transport band (7) (an electron injection layer, an electron transport layer, etc.) is arranged between the light-emitting layer (5) and the cathode (4). In addition, an electron blocking layer (not shown) may be provided on the anode (3) side of the light-emitting layer (5), and a hole blocking layer (not shown) may be provided on the cathode (4) side of the light-emitting layer (5). Thereby, electrons and holes can be confined in the light-emitting layer (5), and the generation efficiency of excitons in the light-emitting layer (5) can be further increased.

FIG. 2 is a schematic diagram showing another configuration of an organic EL element according to one embodiment of the present invention. The organic EL element (11) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (20) disposed between the anode (3) and the cathode (4). The light-emitting unit (20) has a light-emitting layer (5). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), and a second hole transport layer (6c). In addition, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

FIG. 3 is a schematic diagram showing another configuration of an organic EL device according to one embodiment of the present invention. The organic EL device (12) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (30) disposed between the anode (3) and the cathode (4). The light-emitting unit (30) has a light-emitting layer (5). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), a second hole transport layer (6c), and a third hole transport layer (6d). In addition, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

In FIGS. 1 to 3, the light-emitting layer (5) includes at least one light-emitting layer. The light-emitting layer (5) may be a single layer or may include multiple layers (for example, multiple light-emitting layers, multiple light-emitting layers and a space layer).

Meanwhile, in the present invention, a host combined with a fluorescent dopant material (fluorescent emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called a phosphorescent host. A fluorescent host and a phosphorescent host are not distinguished only by their molecular structures. That is, a phosphorescent host means a material that forms a phosphorescent emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent emitting layer. The same applies to a fluorescent host.

Substrate

The substrate is used as a support for the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate may be used. As the flexible substrate, for example, a plastic substrate made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be mentioned. In addition, an inorganic deposition film can also be used.

anode

For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, examples thereof include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride), etc.

These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 to 10 wt% of zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide relative to indium oxide. In addition, it can be produced by vacuum deposition, coating, inkjet, spin coating, etc.

Positive transport band

As described above, the organic layer may include a hole transport zone between the anode and the light-emitting layer. The hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport zone includes the invention compound. It is preferable that at least one of these layers constituting the hole transport layer includes the invention compound, and it is more preferable that the hole transport layer includes the invention compound.

Since the hole injection layer formed in contact with the anode is formed using a material that is easy to inject holes regardless of the work function of the anode, materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or 2 of the periodic table of elements) can be used.

It is also possible to use elements belonging to Group 1 or 2 of the Periodic Table of Elements, which are materials with a small work function, namely, alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. Meanwhile, when forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum deposition method or a sputtering method can be used. In addition, when using silver paste or the like, a coating method or an inkjet method can be used.

Hole injection layer

The hole injection layer is a layer containing a material with high hole injection properties (hole injection material) and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

As hole-injecting materials other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, and the like can be used.

Low molecular weight organic compounds, 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), Aromatic amine compounds such as 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can also be used as hole injection layer materials.

Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples thereof include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). In addition, polymer compounds to which acids have been added, such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.

Furthermore, it is also desirable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[Chemical formula 133]

(In the above formula, R ²²¹ to ^{R 226} each independently represent a cyano group, -CONH ₂ , a carboxyl group, or -COOR ²²⁷ (R ²²⁷ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, two adjacent groups selected from R ²²¹ and R ²²² , R ²²³ and R ²²⁴ , and R ²²⁵ and R ²²⁶ may be bonded to each other to form a group represented by -CO-O-CO-.)

Examples of R ²²⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

hole transport layer

The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport band may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. In addition, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. That is, the third hole transport layer may be arranged between the second hole transport layer and the light-emitting layer.

In one embodiment of the present invention, it is preferable that the hole transport layer of the single-layer structure is adjacent to the light-emitting layer, and furthermore, it is preferable that the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, etc. described later, may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

In one embodiment of the organic electroluminescence device according to the present invention, at least one of the first hole transport layer and the second hole transport layer contains the invention compound. Specifically, in the hole transport layer having the two-layer structure, the invention compound may be included in one of the first hole transport layer and the second hole transport layer, or may be included in both of them. Furthermore, in another embodiment, at least one of the first to third hole transport layers contains the invention compound. Specifically, in the hole transport layer having the three-layer structure, the invention compound may be included in only one of the first to third hole transport layers, in only two of them, or in all of them.

In one embodiment of the present invention, it is preferable that the invention compound is included in the second hole transport layer, and specifically, it is preferable that the invention compound is included only in the second hole transport layer, or that the invention compound is included in both the first hole transport layer and the second hole transport layer.

In one embodiment of the present invention, the inventive compound included in one or both of the first hole transport layer and the second hole transport layer, or the inventive compound included in at least one or a plurality of the first to third hole transport layers, is preferably a hydrogenosphere from the viewpoint of manufacturing cost.

The above-mentioned hydrogen-containing compound is an inventive compound in which all hydrogen atoms in the inventive compound are hydrogen atoms.

Accordingly, the present invention includes an organic EL device including an inventive compound in which one or both of the first hole transport layer and the second hole transport layer, or at least one or a plurality of the first to third hole transport layers are substantially composed only of a hydrogenophoric substance. The “inventive compound substantially composed only of a hydrogenophoric substance” means that the content ratio of the hydrogenophoric substance with respect to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%).

As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

As aromatic amine compounds, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and An example is 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The compound has a hole mobility of 10 ^-6 cm ² /Vs or more.

Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).

Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

However, compounds other than those mentioned above may be used if they have a higher hole transport property than electron transport property.

In one embodiment of the organic EL device according to the present invention, the first hole transport layer includes a compound represented by the following formula (21) or formula (22).

[Chemical formula 134]

[Among the above equations (21) and (22),

L ^A1 , L ^B1 , L ^C1 , L ^A2 , L ^B2 , L ^C2 and L ^D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

k is 1, 2, 3 or 4,

When k is 1, L ^E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

When k is 2, 3 or 4, plural L ^E2 are equal to or different from each other,

When k is 2, 3 or 4, plural L ^E2 may be combined with each other to form a substituted or unsubstituted monocyclic ring, or may be combined with each other to form a substituted or unsubstituted condensed ring, or may not be combined with each other,

L ^E2 , which does not form the above-mentioned monocyclic ring and also does not form the above-mentioned condensed ring, is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R' ₉₀₁ )(R' ₉₀₂ )(R' ₉₀₃ ),

R' ₉₀₁ , R' ₉₀₂ and R' ₉₀₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

In case there are multiple R' _901s , the multiple R' _901s are identical to each other or different,

When there are multiple R' _902s , the multiple R' _902s are identical or different from each other,

When there are multiple R' _903s , the multiple R' _903s are the same or different from each other.

R ₉₀₁ ~ R ₉₀₇ are each independently a hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In case of multiple R _901s , the multiple R _901s are identical or different from each other,

In case of multiple R _902s , the multiple R _902s are identical or different from each other,

In case of multiple R _903s , the multiple R _903s are identical or different from each other,

In case of multiple R _904s , the multiple R _904s are identical or different from each other,

In case of multiple R _905s , the multiple R _905s are identical or different from each other,

In case of multiple R ₉₀₆ , the multiple R ₉₀₆ are identical or different from each other,

In case there are plural R _907s , the plural R _907s are identical or different.]

Meanwhile, the first hole transport layer may contain one type of compound represented by formula (21) and formula (22), or may contain multiple types of compounds represented by formula (21) and formula (22).

In formulas (21) and (22), A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² are preferably, each independently, selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

In addition, more preferably, in formula (21), at least one of A ¹ , B ¹ , and C ¹ , and in formula (22), at least one of A ² , B ² , C ² , and D ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

The fluorenyl group that A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² can have a substituent at position 9, and may be, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at position 9 may form a ring, and for example, the substituents at position 9 may form a fluorene skeleton or a xanthene skeleton.

L ^A1 , L ^B1 , L ^C1 , L ^A2 , L ^B2 , L ^C2 and L ^D2 are preferably, each independently, a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

Specific examples of compounds represented by formulas (21) and (22) include, for example, the following compounds.

[Chemical Formula 135]

Dopant material of the light-emitting layer

The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, a fluorescent light-emitting material or a phosphorescent light-emitting material can be used as the dopant material. A fluorescent light-emitting material is a compound that emits light from a singlet excited state, and a phosphorescent light-emitting material is a compound that emits light from a triplet excited state.

In one embodiment of the organic EL device according to the present invention, the light-emitting layer is a single layer.

In addition, in another embodiment of the organic EL device according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

As blue fluorescent emitting materials that can be used in the emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

As a green fluorescent emitting material that can be used in the emitting layer, an aromatic amine derivative, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2 PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), Examples include N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

As a red-based fluorescent emitting material that can be used in the emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.

In one aspect of the present invention, it is preferable that the light-emitting layer contains a fluorescent light-emitting material (fluorescent dopant material).

As blue phosphorescent luminescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'-bis-trifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), etc.

As a green phosphorescent emitting material that can be used in the emitting layer, iridium complexes, etc. are used. Examples thereof include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

As red-based phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, examples thereof include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

In addition, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be utilized as phosphorescent emitting materials because the emission is from the rare earth metal ion (electron transition between different multiplicities).

Host material of the luminescent layer

The light-emitting layer may be configured by dispersing the above-described dopant material in another material (host material). It is preferable to use a material that has a lower lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

As a host material, for example,

(1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

(2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

(3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,

(4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: BCP);

9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthrile (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), Condensed aromatic compounds such as 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene; and

N,N-Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (Abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (Abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (Abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (Abbreviation: 2PCAPA), Aromatic amine compounds such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. Multiple types of host materials may be used.

In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[Chemical formula 136]

[Chemical formula 137]

[Chemical formula 138]

In one embodiment of the organic EL device according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one component constituting the first light-emitting layer is different from a component constituting the second light-emitting layer. For example, an embodiment may be exemplified in which a dopant material included in the first light-emitting layer is different from a dopant material included in the second light-emitting layer, or an embodiment may be exemplified in which a host material included in the first light-emitting layer is different from a host material included in the second light-emitting layer.

In the organic EL device according to the present embodiment, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less.

The method for measuring the main peak wavelength of a compound is as follows. A 5 μmol/L toluene solution of the compound to be measured is prepared, placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of the sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. In addition, the emission spectrum measuring device is not limited to the device used herein.

In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is referred to as the main peak wavelength. Meanwhile, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

The luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less may be the dopant material or the host material.

When the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound exhibiting fluorescence emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds exhibiting fluorescence emission having a main peak wavelength of 500 nm or less.

In addition, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer may include a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, and both light-emitting layers may include light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less. Furthermore, when the first light-emitting layer includes a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the first light-emitting layer may be a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, and both materials may be light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less. In addition, when the second light-emitting layer includes a light-emitting compound that exhibits fluorescence emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the second light-emitting layer may be a light-emitting compound that exhibits fluorescence emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescence emission having a main peak wavelength of 500 nm or less.

electron transport layer

The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer.

The electron transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and further, the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole-blocking layer or the like described below may be interposed between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

In the electron transport layer, for example,

(1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

(2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

(3) Polymer compounds can be used.

Examples of the metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: _BeBq2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

As heteroaromatic compounds, for example, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), An example is 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

As polymer compounds, examples thereof include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

The above material is a material having an electron mobility of 10 ^-6 cm ² /Vs or more. Meanwhile, a material other than the above may be used in the electron transport layer as long as the material has a higher electron transport property than a hole transport property.

Electron injection layer

The electron injection layer is a layer containing a material having high electron injection properties. The electron injection layer can be used with an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr), a rare earth metal such as europium (Eu), or ytterbium (Yb), or a compound containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, a plurality of these compounds can be mixed and used.

In addition, a material having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used in the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material having excellent transport properties for the received electrons, and specifically, for example, a material constituting the electron transport layer described above (such as a metal complex or a heteroaromatic compound) can be used. The electron donor may be a material that exhibits electron donating properties to the organic compound. Specifically, an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, an alkali metal oxide or an alkaline earth metal oxide is preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

cathode

For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, that is, alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), or strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), or ytterbium (Yb), and alloys containing these.

Meanwhile, when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum deposition method or a sputtering method can be used. In addition, when using silver paste, etc., a coating method or an inkjet method can be used.

Meanwhile, by providing an electron injection layer, a cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, etc.

Insulating layer

Since organic EL elements apply an electric field to an ultra-thin film, pixel defects due to leakage or short-circuiting are likely to occur. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes.

Examples of materials used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. Meanwhile, mixtures or laminates thereof may also be used.

space layer

The above space layer is a layer provided between the fluorescent emitting layer and the phosphorescent emitting layer, for example, when laminating a fluorescent emitting layer and a phosphorescent emitting layer, for the purpose of preventing excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer or adjusting the carrier balance. In addition, the space layer may also be provided between a plurality of phosphorescent emitting layers.

Since the space layer is provided between the light-emitting layers, it is preferable that it be a material having both electron transport properties and hole transport properties. In addition, in order to prevent the diffusion of triplet energy within the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy is 2.6 eV or higher. As the material used for the space layer, the same as that used for the hole transport layer described above can be mentioned.

low floor

A blocking layer such as an electron-blocking layer, a hole-blocking layer, or an exciton-blocking layer may be provided adjacent to the light-emitting layer. The electron-blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole-transporting layer, and the hole-blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron-transporting layer. The exciton-blocking layer has the function of confining excitons within the light-emitting layer by preventing excitons generated in the light-emitting layer from diffusing to surrounding layers.

Each layer of the above organic EL device can be formed by a conventionally known deposition method, coating method, etc. For example, it can be formed by a known method such as a vacuum deposition method, molecular beam deposition (MBE) method, or a coating method such as a dipping method, spin coating method, casting method, bar coating method, or roll coating method using a solution of a compound forming the layer.

The film thickness of each layer is not particularly limited, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the film thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, it is usually 5 nm to 10 μm, and 10 nm to 0.2 μm is more preferable.

In one embodiment of the organic EL device of the present invention, the total thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less.

In addition, in one embodiment of the organic EL device of the present invention, the thickness of the second hole transport layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably, it is 35 nm or more, and further preferably, it is 100 nm or less.

In addition, in one embodiment of the organic EL device of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably, it is 30 nm or more, and further preferably, it is 100 nm or less.

In addition, in one embodiment of the organic EL device of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship of 0.3<D2/D1<4.0. Preferably, they satisfy the relationship of 0.5<D2/D1<3.5, and more preferably, they satisfy the relationship of 0.75<D2/D1<3.0.

As an embodiment of the organic EL device of the present invention, for example,

An organic EL device having a hole transport layer having the above two-layer configuration,

· A first embodiment, wherein the second hole transport layer comprises the compound of the present invention and the first hole transport layer does not comprise the compound of the present invention;

· A second embodiment, wherein both the first hole transport layer and the second hole transport layer comprise the compound of the present invention;

· A third embodiment, wherein the first hole transport layer comprises the compound of the present invention and the second hole transport layer does not comprise the compound of the present invention;

An organic EL device having a hole transport layer having the three-layer configuration,

· A fourth embodiment, wherein the first hole transport layer comprises the compound of the present invention, and the second and third hole transport layers do not comprise the compound of the present invention;

· A fifth embodiment, wherein the second hole transport layer comprises the compound of the present invention, and the first and third hole transport layers do not comprise the compound of the present invention;

· A sixth embodiment, wherein the third hole transport layer comprises the compound of the present invention, and the first and second hole transport layers do not comprise the compound of the present invention;

· A seventh embodiment, wherein the first and second hole transport layers comprise the compound of the present invention, and the third hole transport layer does not comprise the compound of the present invention;

· An eighth embodiment, wherein the first and third hole transport layers comprise the compound of the present invention, and the second hole transport layer does not comprise the compound of the present invention;

· A ninth embodiment, wherein the second and third hole transport layers comprise the compound of the present invention, and the first hole transport layer does not comprise the compound of the present invention;

· A tenth embodiment, wherein all of the first to third hole transport layers comprise the compound of the present invention; etc.

Electronic devices

The above organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices for lighting and vehicle lighting.

Example

Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited thereto.

Compound used in the manufacture of organic EL device of the example

[Chemical Formula 139]

Comparative compound used in the manufacture of organic EL device of comparative example

[Chemical formula 140]

Other compounds used in the manufacture of organic EL devices of examples and comparative examples

[Chemical Formula 141]

[Chemical formula 142]

[Chemical formula 143]

Fabrication of organic EL devices

Example 1-1

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate above, after cleaning, was mounted on a substrate holder of a vacuum deposition device, and compound HI-1 was deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, thereby forming a hole injection layer with a film thickness of 5 nm.

Next, compound 1 was deposited as compound HT-1 on the hole injection layer to form a first hole transport layer with a film thickness of 75 nm.

Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 15 nm.

Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 98:2.

Next, compound ET-1 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 15 nm.

Next, compound ET-2 and Li were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. The mass ratio of compound ET-2 and Li (ET-2:Li) was 96:4.

Next, metal Al was deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm.

The layer configuration of the organic EL device of Example 1-1 obtained in this manner is shown below.

ITO(130)/HI-1(5)/HT-1(75)/HT-2(15)/BH-1:BD-1=98:2(20)/ET-1(15)/ET-2:Li=96:4(15)/Al(80)

Meanwhile, in the above layer configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Comparative examples 1-1∼1-3

An organic EL device was manufactured in the same manner as in Example 1, except that the second hole transport layer material was changed from Compound 1 to Comparative Compounds 1, 2, and 3, respectively.

Evaluation of organic EL devices

For the organic EL devices manufactured in Example 1-1 and Comparative Examples 1-1 to 1-3, a voltage was applied to the organic EL devices so that the current density became 10 mA/cm ² , and the external quantum efficiency (EQE) was evaluated. The voltage value at that time was measured and used as the driving voltage.

The results are shown in Table 1.

As is clear from the results in Table 1, it can be seen that the compound satisfying the provisions of the present invention (compound 1 of Example 1-1) exhibits significantly improved driving voltage and EQE values compared to the monoamines that do not satisfy the provisions of the present invention (comparative compounds 1, 2, and 3 of Comparative Examples 1-1 to 1-3).

Example 2-1

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate above, after cleaning, was mounted on a substrate holder of a vacuum deposition device, and compound HI-1 was deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, thereby forming a hole injection layer with a film thickness of 5 nm.

Next, compound HT-3 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 37.5 nm.

Next, compound 1 was deposited as compound HT-1 on the first hole transport layer to form a second hole transport layer with a film thickness of 37.5 nm.

Next, compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 15 nm.

Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 98:2.

Next, compound ET-1 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 15 nm.

Next, compound ET-2 and Li were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. The mass ratio of compound ET-2 and Li (ET-2:Li) was 96:4.

Next, metal Al was deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm.

The layer configuration of the organic EL device of Example 2-1 obtained in this manner is shown below.

ITO(130)/HI-1(5)/HT-3(37.5)/HT-1(37.5)/HT-2(15)/BH-1:BD-1=98:2(20)/ET-1(15)/ET-2:Li=96:4(15)/Al(80)

Meanwhile, in the above layer configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Example 2-2

An organic EL device was manufactured in the same manner as in Example 2-1, except that the second hole transport layer material was changed from compound 1 to compound 2.

Comparative examples 2-1, 2-2

An organic EL device was manufactured in the same manner as in Example 2-1, except that the second hole transport layer material was changed from Compound 1 to Comparative Compounds 1 and 3.

Evaluation of organic EL devices

For the organic EL devices manufactured in Examples 2-1, 2-2, Comparative Example 2-1, and Comparative Example 2-2, a voltage was applied to the organic EL devices so that the current density became 10 mA/cm ² , and the external quantum efficiency (EQE) was evaluated. The voltage value at that time was measured and used as the driving voltage.

The results are shown in Table 2.

As is clear from the results in Table 2, it can be seen that the compounds satisfying the provisions of the present invention (compounds 1 and 2 of Examples 2-1 and 2-2) exhibit significantly improved driving voltage and EQE values compared to the monoamines that do not satisfy the provisions of the present invention (compare compounds 1 and 3 of Comparative Examples 2-1 and 2-2).

Example 3-1

A glass substrate (manufactured by Geomatech Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate above, after cleaning, was mounted on a substrate holder of a vacuum deposition device, and compounds HT-4 and HI-2 were co-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, thereby forming a hole injection layer having a film thickness of 10 nm. The mass ratio of compounds HT-4 and HI-2 (HT-4:HI-2) was 95:5.

Next, compound HT-4 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 30 nm.

Next, compound 1 was deposited as a second hole transport material HT-1 on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

Next, compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 15 nm.

Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 98:2.

Next, compound ET-1 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 10 nm.

Next, compound ET-2 and Li were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET-2 and Li (ET-2:Li) was 96:4.

Next, metal Al was deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm.

The layer configuration of the organic EL device of Example 2-1 obtained in this manner is shown below.

ITO(130)/HI-4:HI-2=95:5(10)/HT-4(30)/HT-1(40)/HT-2(15)/BH-1:BD-1=98:2(20)/ET-1(10)/ET-2:Li=96:4(20)/Al(80)

Meanwhile, in the above layer configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Examples 3-2 to 3-6

An organic EL device was manufactured in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from Compound 1 to Compounds 4 to 8, respectively.

Example 3-7

An organic EL device was manufactured in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from compound 1 to compound 3.

Comparative examples 3-1, 3-2

An organic EL device was manufactured in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from Compound 1 to Comparative Compounds 1 and 3, respectively.

Evaluation of organic EL devices

For the organic EL devices manufactured in Examples 3-1 to 3-7, Comparative Example 3-1, and Comparative Example 3-2, a voltage was applied to the organic EL devices so that the current density became 10 mA/cm ² , and the external quantum efficiency (EQE) was evaluated. The voltage value at that time was measured and used as the driving voltage.

The results are shown in Table 3.

As is clear from the results in Table 3, it can be seen that the compounds satisfying the provisions of the present invention (compounds 1, 4 to 8, and compound 3 of Examples 3-1 to 3-7) exhibit significantly improved driving voltage and EQE values compared to the monoamines that do not satisfy the provisions of the present invention (compounds 1 and 3 of Comparative Examples 3-1 and 3-2).

Example 4-1

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate above, after cleaning, with the transparent electrode attached, was mounted on a substrate holder of a vacuum deposition device, and first, a transparent electrode was covered on the side on which the transparent electrode was formed, and compound 1 as a hole transport material HT-1 and compound HI-2 were co-deposited to form a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1 and compound HI-2 (HT-1:HI-2) was 97:3.

Next, compound 1 was deposited as the first hole transport material HT-1 on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

Next, compound HT-5 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 99:1.

Next, compound ET-5 was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

Next, on the first electron transport layer, compound ET-6 and Liq were co-deposited to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-6 and Liq (ET-6:Liq) was 50:50.

Next, metal Yb was deposited on this second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

Next, metal Al was deposited on the electron injection layer to form a metal cathode with a film thickness of 50 nm.

The layer configuration of the organic EL device of Example 2-1 obtained in this manner is shown below.

ITO(130)/HT-1:HI-2=97:3(10)/HT-1(80)/HT-5(5)/BH-2:BD-2=99:1(20)/ET-5(5)/ET-6:Liq=50:50(25)/Yb(1)/Al(50)

Meanwhile, in the above layer configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Examples 4-2, 4-3

An organic EL device was manufactured in the same manner as in Example 4-1, except that the hole transport material and the first hole transport material used in the hole injection layer were changed from compound 1 to compound 4 (Example 4-2) and from compound 1 to compound 6 (Example 4-3).

Comparative examples 4-1, 4-2

An organic EL device was manufactured in the same manner as in Example 4-1, except that the hole transport material and the first hole transport material used in the hole injection layer were changed from Compound 1 to Comparative Compound 3 (Comparative Example 4-1) and from Compound 1 to Comparative Compound 4 (Comparative Example 4-2).

Evaluation of organic EL devices

For the organic EL devices manufactured in Examples 4-1 to 4-3, Comparative Example 4-1, and Comparative Example 4-2, a voltage was applied to the organic EL devices so that the current density became 10 mA/cm ² , and the external quantum efficiency (EQE) was evaluated. The voltage value at that time was measured and used as the driving voltage.

The results are shown in Table 4.

As is clear from the results in Table 4, it can be seen that the compounds satisfying the provisions of the present invention (compounds 1, 4, and 6 of Examples 4-1 to 4-3) exhibit significantly improved driving voltage and EQE values compared to the monoamines that do not satisfy the provisions of the present invention (compare compounds 3 and 4 of Comparative Examples 4-1 and 4-2).

Compound synthesized in the synthetic example

[Chemical formula 144]

<Synthesis of compounds>

Intermediate Synthesis Example 1: Synthesis of Intermediate A

[Chemical formula 145]

Under an argon atmosphere, a THF solution (1.0 M) of 2-bromo-4'-chloro-1,1'-biphenyl (4.81 g, 18 mmol) was slowly added dropwise to a reactor containing magnesium (0.656 g, 27.0 mmol), and stirring was performed at room temperature. After the entire addition, stirring was performed under reflux for 1 hour, and an organic magnesium reactant was prepared.

In another reactor, 1-indanone (1.98 g, 15 mmol) and THF (13 mL) were added under an argon atmosphere, and the previously prepared organomagnesium reactant was added dropwise. Then, the mixture was stirred for 5 hours under reflux. The reaction solution was cooled to room temperature, and a saturated ammonium chloride aqueous solution and ethyl acetate were added and stirred. After removing the aqueous layer using a separatory funnel, the obtained solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain an orange oil. The obtained oil was dissolved in xylene (75 mL), p-toluenesulfonic acid monohydrate (8.56 g, 45 mmol) was added, the temperature was raised to 140°C, and stirring was performed for 5 hours. After cooling, water was added, the aqueous layer was removed, and the obtained solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain intermediate A as a colorless solid (1.82 g). The yield in the second process was 40%.

Intermediate Synthesis Example 2: Synthesis of Intermediate B

[Chemical formula 146]

Intermediate B was obtained by performing the same operation as Intermediate Synthesis Example 1, except that 3,3-dimethyl-1-indanone was used instead of 1-indenone used in Intermediate Synthesis Example 1. The yield in the second step was 41%.

Synthesis Example 1: Synthesis of Compound 1

[Chemical formula 147]

A mixture of intermediate A (1.82 g, 6.01 mmol), 2-(2-biphenylyl)amino-9,9-dimethylfluorene (2.173 g, 6.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.11 g, 0.120 mmol), tri-t-butylphosphonium tetrafluoroborate (0.140 g, 0.481 mmol), sodium-t-butoxide (0.809 g, 8.41 mmol), and xylene (40 mL) was stirred at 120°C for 5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.98 g of a white solid. The yield was 79%.

The obtained compound was found to be compound 1 as a result of mass spectrum analysis, and m/e=627 for a molecular weight of 627.29.

Synthesis Example 2: Synthesis of Compound 2

[Chemical formula 148]

Compound 2 was obtained by performing the same operation as in Synthesis Example 1, except that 2-bromo-1',3'-dihydrospiro[fluorene-9,2'-indene], synthesized by the same method as described in International Publication No. 2004/110968, was used instead of intermediate A used in Synthesis Example 1 above.

The obtained product was, as a result of mass spectrum analysis, compound 2, and m/e=627 for a molecular weight of 627.29.

Synthesis Example 3: Synthesis of Compound 3

[Chemical Formula 149]

Compound 3 was obtained by performing the same operation as in Synthesis Example 1, except that intermediate B was used instead of intermediate A used in Synthesis Example 1.

The obtained compound was, as a result of mass spectrum analysis, compound 3, and m/e=655 for a molecular weight of 655.32.

Intermediate Synthesis Example 3: Synthesis of Intermediate C

[Chemical formula 150]

Compound C was obtained by performing the same operation as in Intermediate Synthesis Example 1, except that 6-(tert-butyl)-2,3-dihydro-1H-indene-1-one was used instead of 1-indanone used in Intermediate Synthesis Example 1. The yield was 39%.

Synthesis Example 4: Synthesis of Compound 4

[Chemical Formula 151]

Compound 4 was obtained by performing the same operation as in Synthesis Example 1, except that N-([1,1':4',1"-terphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1.

The obtained compound was compound 4 as a result of mass spectrum analysis, and m/e=704 for molecular weight 703.93.

Synthesis Example 5: Synthesis of Compound 5

[Chemical formula 152]

Compound 5 was obtained by performing the same operation as in Synthesis Example 1, except that intermediate C was used instead of intermediate A used in Synthesis Example 1.

The obtained compound was compound 5 as a result of mass spectrum analysis, and m/e=684 for molecular weight 683.94.

Synthesis Example 6: Synthesis of Compound 6

[Chemical Formula 153]

Compound 6 was obtained by performing the same operation as in Synthesis Example 1, except that N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1.

The obtained compound was compound 6 as a result of mass spectrum analysis, and m/e=752 for molecular weight 751.97.

Synthesis Example 7: Synthesis of Compound 7

[Chemical Formula 154]

Compound 7 was obtained by performing the same operation as in Synthesis Example 1, except that N-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1.

The obtained compound was found to be compound 7 as a result of mass spectrum analysis, and m/e=718 for a molecular weight of 717.91.

Synthesis Example 8: Synthesis of Compound 8

[Chemical Formula 155]

Compound 8 was obtained by performing the same operation as in Synthesis Example 1, except that N-([1,1':2',1"-terphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1.

The obtained compound was found to be 8 as a result of mass spectrum analysis, and m/e=704 for a molecular weight of 703.93.

1, 11, 12 Organic EL devices
2 substrates
3 anode
4 cathode
5 luminous layer
6 Hole transport band (hole transport layer)
6a hole injection layer
6b 1st hole transport layer
6c 2nd hole transport layer
6d 3rd hole transport layer
7 Electron transport band (electron transport layer)
7a 1st electron transport layer
7b Second electron transport layer
10, 20, 30 luminous units

Claims (33)

A compound represented by the following formula (1A) or (1B).


[In Equation (1A),
N ^* is the central nitrogen atom.
One selected from Z ¹ and Z ² is a single bond binding to *a.
The above-mentioned Z ¹ and Z ² , R ^13A , R ^14A , and R ¹⁵ to R ¹⁸ , R ⁷ to R ¹⁰ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
Z ¹ and Z ² , R ^13A , and R ^14A , which are not single bonds, do not combine with each other to form a ring.
A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.
A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.
R ^1A and R ^2A are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
R ^1A and R ^2A may be combined with each other to form a ring or may not form a ring.
Y ¹ and Y ² are hydrogen atoms.
L ¹ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
n1 is either 0 or 1.
When n1 is 0, one selected from Z ¹ and Z ² is bonded to the central nitrogen atom N ^* .
X ¹ is an oxygen atom, a sulfur atom, or =CR ^A R ^B.
One selected from R ^A , R ^B , and R ²¹ to R ²⁸ is a single bond binding to *b1, or one selected from R ^A and R ^B is a divalent group binding to *b1.
R ^A and R ^B , which are not single bonds and are not divalent groups bonded to *b1, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R ^A and R ^B , which are not single bonds and are not divalent groups bonded to *b1, may or may not bond to each other to form a ring.
The above R ²¹ to R ²⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
When one selected from R ²¹ to ^{R 24} is a single bond bonding to *b1, R ²¹ to R ²⁴ that are not single bonds do not combine with each other to form a ring, and further, R ²⁵ to R ²⁸ may or may not combine with each other to form a ring.
When one selected from R ²⁵ to ^{R 28} is a single bond bonding to *b1, R ²⁵ to R ²⁸ that are not single bonds do not combine with each other to form a ring, and further, R ²¹ to R ²⁴ may or may not combine with each other to form a ring.
L ² is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
n2 is 0 or 1.
When n2 is 0, one selected from R ²¹ to R ²⁸ bonds to the central nitrogen atom N ^* .
Ar ¹ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
m is 0, 1, 2, 3, or 4. However, when Ar ¹ is a hydrogen atom, m is 0.
When m is 1 to 4, 1 to 4 selected from R ³¹ to R ³⁴ are single bonds bonding to *c. When m is 2 to 4, plural Ar ² may be the same or different.
The above R ³¹ to R ³⁴ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
A pair of adjacent groups among Ar ¹ , which is not a hydrogen atom, and R ³⁴ to R ²⁴ , which are not hydrogen atoms, may or may not form a ring by combining with each other.
In equation (1B),
One selected from R ¹¹ to R ¹⁴ is a single bond bonding to *a.
The above single bonds, R ¹¹ to R ¹⁴ , R ¹⁵ to R ¹⁸ , and R ⁷ to R ¹⁰ , are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
R ¹¹ to R ¹⁴ , which are not single bonds, do not combine with each other to form a ring.
A pair of adjacent groups among R ⁷ to R ¹⁰ may combine with each other to form a ring or may not form a ring.
A pair of adjacent groups among R ¹⁵ to ^{R 18} may combine with each other to form a ring or may not form a ring.
R ^1B , R ^2B , R ^5B , and R ^6B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
R ^1B and R ^2B may be combined with each other to form a ring or may not form a ring.
R ^5B and R ^6B may or may not combine with each other to form a ring.
L ³ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
n3 is 0 or 1.
When n3 is 0, Ar ³ binds to the central nitrogen atom N ^* .
Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2).

(In equation (2-1),
** indicates the binding position to L ³ .
X ³ is an oxygen atom or a sulfur atom.
One selected from R ⁴¹ to R ⁴⁴ is a single bond bonding to *d.
The above R ⁴¹ to R ⁴⁴ and R ⁴⁵ to R ⁴⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
Among the above-mentioned single bonds, a pair of adjacent groups among R ⁴¹ to ^{R 44} and a pair of adjacent groups among R ⁴⁵ to R ⁴⁸ may or may not be bonded to each other to form a ring.
In equation (2-2),
** indicates the binding position to L ³ .
R ⁴¹ to R ⁴⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
A pair of adjacent groups among R ⁴¹ to ^{R 48} may or may not form a ring by combining with each other.)
L ⁴ is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
n4 is either 0 or 1.
When n4 is 0, Ar ⁴ binds to the central nitrogen atom N ^* .
Ar ⁴ is a group represented by the following formula (3-1) or a group represented by the following formula (3-2).

(In equation (3-1),
*** indicates the binding position to L ⁴ .
X ² is an oxygen atom, a sulfur atom, or =CR ^C R ^D.
One selected from R ^21B ∼R ^24B , R ^C , and R ^D is a single bond binding to *b2, or one selected from R ^C and R ^D is a divalent group binding to *b2.
The above-mentioned R ^21B ∼R ^24B , R ^25B ∼R ^28B , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
When one selected from R ^21B to ^{R 24B} is a single bond bonding to *b2, R ^21B to R ^24B that are not single bonds do not combine with each other to form a ring, and further, R ^25B to R ^28B may or may not combine with each other to form a ring.
When one selected from R ^25B to R ^28B is a single bond bonding to *b2, R ^25B to R ^28B that are not single bonds do not combine with each other to form a ring, and further, R ^21B to R ^24B may or may not combine with each other to form a ring.
The above-mentioned R ^C and R ^D , which are not single bonds and are not divalent groups bonded to the above-mentioned *b2, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, and they may or may not form a ring when bonded to each other. However, when one selected from R ^C and R ^D is an aryl group, the two do not bond to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R ^C and R ^D are bonded.
If X ² is an oxygen atom or a sulfur atom, n4 is 1.
In equation (3-2),
*** indicates the binding position to L ⁴ .
R ^21B ∼R ^28B are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
A pair of adjacent groups among R ^21B ∼ ^{R 24B} and a pair of adjacent groups among R ^25B ∼ R ^28B may or may not form a ring by combining with each other.)
In Equation (1-B), N ^* , L ¹ , and n1 have the same meanings as defined in Equation (1A).] In the first paragraph,
A compound represented by the following formula (1A-1).

[In formula (1A-1), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ ∼R ¹⁰ , Z ¹ , R ^13A , R ^14A , R ¹⁵ ∼R ¹⁸ , R ²¹ ∼R ²⁸ , X ¹ , R ³¹ ∼R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *b1, *c, m, n1, and n2 are as defined in the above formula (1A).] In the first paragraph,
A compound represented by the following formula (1A-2).

[In formula (1A-2), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ ∼R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ ∼R ¹⁸ , R ²¹ ∼R ²⁸ , R ^A , R ^B , R ³¹ ∼R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1, and n2 are as defined in the formula (1A) above.] In the third paragraph,
A compound wherein one of R ²¹ , R ²² , R ²⁴ , R ²⁵ , R ²⁷ , and R ²⁸ is a single bond bonding to *b1. In any one of claims 1 to 4,
A compound represented by the above formula (1A), formula (1A-1), or formula (1A-2), wherein when n1 is 1, L ¹ is a phenylene group, and when n2 is 1, L ² is a phenylene group. In the first paragraph,
A compound represented by any of the following formulas (1A-3) to (1A-5).



[In formula (1A-3) and formula (1A-5), R ⁵¹ to R ⁵⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. However, one selected from R ⁵¹ to R ⁵⁵ is a single bond bonding to *d. Adjacent groups of R ⁵¹ to R ⁵⁵ that are not single bonds do not bond to each other and do not form a ring.
In formulas (1A-4) and (1A-5), R ⁶¹ to R ⁶⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R ⁶¹ to R ⁶⁵ is a single bond bonding to *e. Adjacent groups of R ⁶¹ to R ⁶⁵ that are not single bonds do not bond to each other and do not form a ring.
In formulas (1A-3) to (1A-5), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ to R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ to R ¹⁸ , R ²¹ to R ²⁸ , X ¹ , R ³¹ to R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1 , and n2 are as defined in the above formula (1A).] In the first paragraph,
A compound represented by any of the following formulas (1A-6) to (1A-8).



[In formulas (1A-6) to (1A-8), R ^1A , R ^2A , Y ¹ , Y ² , R ⁷ to R ¹⁰ , Z ¹ , Z ² , R ^13A , R ^14A , R ¹⁵ to R ¹⁸ , R ²¹ to R ²⁸ , X ¹ , R ³¹ to R ³⁴ , N ^* , Ar ¹ , Ar ² , L ¹ , L ² , *a, *b1, *c, m, n1 , and n2 are as defined in the above formula (1A).] In any one of claims 1 to 7,
It is expressed by any of the above formula (1A), and formulas (1A-1) to (1A-8),
· Ar ¹ is a hydrogen atom, and m is 0, or
· Ar ¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 0, or
· A compound in which Ar ¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 1. In any one of claims 1 to 8,
A compound represented by any of the above formulas (1A) and (1A-1) to (1A-8), wherein Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. In the first paragraph,
A compound represented by the following formula (1B-1).

[In formula (1B-1), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ ∼R ¹⁰ , R ¹¹ , R ¹³ ∼R ¹⁸ , N ^* , Ar ³ , Ar ⁴ , L ¹ , L ³ , L ⁴ , n1 , n3 , and n4 are as defined in the formula (1B) above.] In the first paragraph,
A compound represented by the following formula (1B-2).

[In formula (1B-2), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ ∼R ¹⁰ , R ¹¹ ∼R ¹⁸ , R ^21B ∼R ^28B , R ^C , R ^D , N ^* , Ar ³ , L ¹ , L ³ , L ⁴ , *a, *b2, n1, n3, and n4 are as defined in the above formula (1B).] In Article 11,
Ar ³ is a compound which is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In any one of paragraph 1 and paragraphs 10 to 12,
A compound represented by any one of the above formulas (1B), (1B-1), and (1B-2), wherein when n1 is 1, L ¹ is a phenylene group, when n3 is 1, L ³ is a phenylene group, and when n4 is 1, L ⁴ is a phenylene group. In the first paragraph,
A compound represented by any of the following formulas (1B-3) to (1B-9).







[In formula (1B-3), formula (1B-6), formula (1B-7), and formula (1B-9), R ⁵¹ to R ⁵⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R ⁵¹ to R ⁵⁵ is a single bond bonding to *d.
Among the above-mentioned single bonds, adjacent groups R ⁵¹ to R ⁵⁵ do not bond with each other and do not form a ring.
In formulas (1B-4), (1B-6), (1B-8), and (1B-9), R ⁷¹ to R ⁷⁵ each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R ⁷¹ to R ⁷⁵ is a single bond bonding to *f.
Among the above-mentioned single bonds, adjacent groups R ⁷¹ to R ⁷⁵ do not bond with each other and do not form a ring.
In formulas (1B-5) and (1B-7) to (1B-9), R ⁸¹ to R ⁸⁵ each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. However, one selected from R ⁸¹ to R ⁸⁵ is a single bond bonding to *g.
Among the above-mentioned single bonds, adjacent groups R ⁸¹ to R ⁸⁵ do not bond with each other and do not form a ring.
In formulas (1B-3) to (1B-9), R ^1B , R ^2B , R ^5B , R ^6B , R ⁷ to R ¹⁰ , R ¹¹ to R ¹⁸ , N ^* , Ar ³ , Ar ⁴ , L ¹ , L ³ , L ⁴ , *a, n1, n3, and n4 are as defined in the above formula (1B).] In any one of paragraphs 1, 10, and 14,
It is expressed by any of the above formulas (1B), (1B-1), and (1B-3) to (1B-9),
Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A compound in which Ar ⁴ is a group represented by the above formula (3-1), and further X ² is an oxygen atom or a sulfur atom, or a group represented by the above formula (3-2). In any one of paragraphs 1, 10, and 14,
It is expressed by the above formula (1B),
Ar ³ is a group represented by the above formula (2-1) or formula (2-2),
A compound in which Ar ⁴ is a group represented by the above formula (3-1), and further X ² is an oxygen atom or a sulfur atom, or a group represented by the above formula (3-2). In any one of paragraph 1 and paragraphs 10 to 15,
A compound represented by any one of the above formulas (1B) and formulas (1B-1) to (1B-9), and Ar ³ is represented by any one of the following formulas (2A) to (2F).

(In equation (2A),
· *21 is the binding position to L ³ .
· One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23.
· R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
· Two adjacent groups selected from R ¹⁰¹ to R ¹⁰⁵ that are not the above single bonds do not bond to each other and do not form a ring.
· Two adjacent groups selected from R ¹⁰⁶ to R ¹¹⁰ that are not the above single bonds do not bond to each other and do not form a ring.
· R ¹¹¹ to R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
· Two adjacent groups selected from R ¹¹¹ to R ¹¹⁵ do not bind to each other and do not form a ring.
· m11 is 0, 1, or 2, and n11 is 0 or 1. Except when m11 is 2 and n11 is 0.
· When m11=0, n11=0, *23 represents *21.
· When m11=0, n11=1, *22 represents *21.
· When m11=1, n11=0, *23 represents *22.)

(In equation (2B),
· *24 is the binding position to L ³ .
· One selected from R ¹²¹ to R ¹²⁸ is a single bond binding to *25.
· R ¹²¹ to R ¹²⁸ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
· Two adjacent groups selected from R ¹²¹ to R ¹²⁸ that are not the above single bonds do not bond to each other and do not form a ring.)

(In equation (2C),
· *26 is the binding position to L ³ .
· One selected from R ¹³¹ to R ¹⁴⁰ is a single bond binding to *27.
· R ¹³¹ to R ¹⁴⁰ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
· Two adjacent groups selected from R ¹³¹ to R ¹⁴⁰ that are not the above single bonds do not bond to each other and do not form a ring.)

(In equation (2D),
· *28 is the binding position to L ³ .
· n12 is 0 or 1.
· When n12 is 0, one selected from R ¹⁴¹ - R ¹⁴⁸ , R ^E , and R ^F is a single bond binding to *29, or one selected from R ^E and R ^F is a divalent group binding to *29.
· When n12 is 1, one of R ¹⁴¹ and R ¹⁴² , R ¹⁴² and R ¹⁴³ , or R ¹⁴³ and R ¹⁴⁴ is a single bond bonding to *h, the other is a single bond bonding to *i, and one selected from R ¹⁴¹ to R ¹⁴⁴ , R ¹⁴⁵ to R ¹⁴⁸ , R ²⁰⁰ to R ²⁰³ , R ^E , and R ^F which is not a single bond bonding to *h and *i, is a single bond bonding to *29, or one selected from R ^E and R ^F is a divalent group bonding to *29.
· R ¹⁴¹ to R ¹⁴⁸ , which are not single bonds, and R ²⁰⁰ to R ²⁰³ , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
· Two adjacent groups selected from R ¹⁴¹ to ^{R 148} that are not the single bond and R ²⁰⁰ to R ²⁰³ that are not the single bond do not bond to each other and do not form a ring.
· R ^E and R ^F , which are not the single bond and are not the divalent group bonded to the above *29, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, and may or may not form a ring by bonding to each other. However, when one selected from R ^E and R ^F is an aryl group, the two do not bond to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R ^E and R ^F are bonded.)

(In equation (2E),
· *30 is the binding position to L ³ .
· One selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *31, and another selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *32.
· R ¹⁵¹ to R ¹⁵⁵ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.
· Two adjacent groups selected from R ¹⁵¹ to R ¹⁵⁵ that are not the above single bonds do not bond to each other and do not form a ring.
· R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to ^{R 175} are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
· At least two adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ that are not hydrogen atoms may be combined with each other to form one or more unsubstituted benzene rings, or may not be combined with each other to form a ring.
· At least two adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ that are not hydrogen atoms may be combined with each other to form one or more unsubstituted benzene rings, or may not be combined with each other and thus may not form a ring.)

(In equation (2F),
· *32 is the binding position to L ³ .
· One selected from R ¹⁸¹ to R ¹⁹² is a single bond binding to *33.
· R ¹⁸¹ to R ¹⁹² , which are not single bonds, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
· Two adjacent groups selected from R ¹⁸¹ to R ¹⁹² that are not the above single bonds do not bond to each other and do not form a ring.) In any one of paragraphs 1, 2, 6, and 7,
A compound in which ^X1 is an oxygen atom. In any one of paragraphs 1, 10, and 14 to 16,
A compound in which ^X2 is an oxygen atom. In any one of paragraphs 1, 10, 14, and 16,
A compound in which ^X3 is an oxygen atom. In any one of claims 1 to 20,
A compound represented by the above formula (1A) or formula (1B) containing at least one deuterium atom. In the first paragraph,
A compound comprising any one of the compounds 1 to 8 below.
A material for an organic electroluminescence device, comprising a compound according to any one of claims 1 to 22. In Article 29,
A material for an organic electroluminescence device, wherein the compound described in any one of claims 1 to 22 is a hole transport layer material. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer is composed of a single or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprises a compound according to any one of claims 1 to 22. In Article 25,
An organic electroluminescent device, wherein the organic layer comprises a hole transport band between the anode and the light-emitting layer, and the hole transport band comprises a compound according to any one of claims 1 to 22. In paragraph 26,
The above hole transport band includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side,
An organic electroluminescence device, wherein at least one of the first hole transport layer and the second hole transport layer comprises a compound according to any one of claims 1 to 22. In Article 27,
An organic electroluminescent device, wherein the second hole transport layer comprises a compound according to any one of claims 1 to 22. In clause 27 or 28,
An organic electroluminescence device, wherein the light-emitting layer and the second hole transport layer are in direct contact. In any one of paragraphs 27 to 29,
An organic electroluminescence device, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less. In any one of paragraphs 25 to 30,
An organic electroluminescent device, wherein the light-emitting layer comprises a layer containing a light-emitting compound that exhibits fluorescence emission having a main peak wavelength of 500 nm or less. In any one of paragraphs 25 to 31,
An organic electroluminescent device, wherein the above-mentioned light-emitting layer is a single layer. An electronic device comprising an organic electroluminescent device according to any one of claims 25 to 32.