KR20240122087A - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light-emitting device comprising: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; a first organic layer provided between the anode and the light-emitting layer and including a compound of the chemical formula 1; and a second organic layer provided between the anode and the light-emitting layer and including a compound of the chemical formula 2.

Description

ORGANIC LIGHT EMITTING DEVICE

This specification relates to an organic light-emitting device.

In general, the organic luminescence phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices utilizing the organic luminescence phenomenon usually have a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continued need for the development of new materials for organic light-emitting devices such as the above.

International Patent Application Publication No. 2003-012890

The present specification provides an organic light-emitting device.

The present invention provides an organic light-emitting device comprising: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; a first organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 1; and a second organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 2.

[Chemical Formula 1]

[Chemical formula 2]

In the above chemical formulas 1 and 2,

Ar1 to Ar4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring formed by condensation of these groups,

R4 to R9 are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group,

R1 is a substituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in which an aromatic ring and an aliphatic ring are condensed,

R2 and R3 are the same or different, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

L1 to L5 are the same or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

a and c to f are integers from 0 to 4, respectively,

b is an integer from 0 to 2,

When a to f are 2 or more, R4 to R9 are each the same or different;

p and t are integers from 0 to 2, respectively.

An organic light-emitting device according to one embodiment of the present specification can exhibit low driving voltage and have improved efficiency and lifespan by appropriately controlling the HOMO and LUMO energies of a compound to control the barrier between organic layers.

FIG. 1 illustrates an organic light-emitting device according to one embodiment of the present specification.
FIG. 2 illustrates an organic light-emitting device according to one embodiment of the present specification.

Below, the present specification is described in more detail.

The present invention provides an organic light-emitting device comprising: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; a first organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 1; and a second organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 2.

The compound of the present invention can control the energy barrier with the organic layer by controlling the HOMO and LUMO energy levels of the compound by binding a substituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroaryl group to R1 of chemical formula 1.

Examples of substituents in this specification are described below, but are not limited thereto.

The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e. a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, or substituted with a substituent in which two or more substituents among the above-mentioned substituents are linked, or has no substituents. For example, "a substituent linked with two or more substituents" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, etc.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specific examples include a methyl group; an ethyl group; a propyl group; an n-propyl group; an isopropyl group; a butyl group; an n-butyl group; an isobutyl group; a tert-butyl group; a sec-butyl group; a 1-methylbutyl group; a 1-ethylbutyl group; a pentyl group; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; a hexyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methyl-2-pentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a heptyl group; an n-heptyl group; a 1-methylhexyl group; Examples thereof include, but are not limited to, a cyclopentylmethyl group; a cyclohexylmethyl group; an octyl group; an n-octyl group; a tert-octyl group; a 1-methylheptyl group; a 2-ethylhexyl group; a 2-propylpentyl group; an n-nonyl group; a 2,2-dimethylheptyl group; a 1-ethylpropyl group; a 1,1-dimethylpropyl group; an isohexyl group; a 2-methylpentyl group; a 4-methylhexyl group; a 5-methylhexyl group, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and more preferably one having 3 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group; a cyclobutyl group; a cyclopentyl group; a 3-methylcyclopentyl group; a 2,3-dimethylcyclopentyl group; a cyclohexyl group; a 3-methylcyclohexyl group; a 4-methylcyclohexyl group; a 2,3-dimethylcyclohexyl group; a 3,4,5-trimethylcyclohexyl group; a 4-tert-butylcyclohexyl group; a cycloheptyl group; and a cyclooctyl group.

In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is more preferably 1 to 10 carbon atoms. Specifically, the alkoxy group may be, but is not limited to, a methoxy group; an ethoxy group; an n-propoxy group; an isopropoxy group; an i-propyloxy group; an n-butoxy group; an isobutoxy group; a tert-butoxy group; a sec-butoxy group; an n-pentyloxy group; a neopentyloxy group; an isopentyloxy group; an n-hexyloxy group; a 3,3-dimethylbutyloxy group; a 2-ethylbutyloxy group; an n-octyloxy group; an n-nonyloxy group; an n-decyloxy group; a benzyloxy group; a p-methylbenzyloxy group.

In the present specification, the amine group may be selected from the group consisting of -NH ₂ ; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; an N-phenylnaphthylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; Examples thereof include, but are not limited to, N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group.

In the present specification, a silyl group can be represented by a chemical formula of -SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and can each independently be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group; a triethylsilyl group; a t-butyldimethylsilyl group; a vinyldimethylsilyl group; a propyldimethylsilyl group; a triphenylsilyl group; a diphenylsilyl group; and a phenylsilyl group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and more preferably has 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the carbon number is not particularly limited, but preferably has 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group; a biphenyl group; a terphenyl group, and the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, but preferably has 10 to 30 carbon atoms, and more specifically, it is preferably 10 to 20 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group; anthracenyl group; phenanthryl group; triphenyl group; pyrenyl group; phenalenyl group; perylenyl group; chrysenyl group; It can be a fluorenyl group, but is not limited thereto.

As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the above-mentioned aryl groups.

In the present specification, a heteroaryl group includes at least one non-carbon atom, i.e., a heteroatom, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; a furanyl group; a pyrrole group; an imidazolyl group; a thiazolyl group; a thiazolyl group; an oxazolyl group; an oxadiazolyl group; a pyridyl group; a bipyridyl group; a pyrimidyl group; a triazinyl group; a triazolyl group; an acridyl group; a pyridazinyl group; a pyrazinyl group; a quinolinyl group; a quinazolinyl group; a quinoxalinyl group; a phthalazinyl group; a pyrido pyrimidyl group; Examples thereof include, but are not limited to, a pyrido pyrazinyl group; a pyrazino pyrazinyl group; an isoquinolinyl group; an indolyl group; a carbazolyl group; a benzoxazolyl group; a benzimidazolyl group; a benzothiazolyl group; a benzocarbazolyl group; a benzothiophene group; a dibenzothiophene group; a benzofuranyl group; a phenanthroline group; an isoxazolyl group; a thiadiazolyl group; a phenothiazinyl group, and a dibenzofuranyl group.

In the present specification, a heterocyclic group is one that includes at least one atom other than carbon, i.e., a heteroatom, and specifically, the heteroatom includes at least one atom selected from the group consisting of O, N, Se, and S, and includes an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group can be represented by a heteroaryl group. An aliphatic heterocyclic group refers to a case where a heteroatom is included in an aliphatic hydrocarbon ring such as tetrahydrofuran or pyrrolidine, or a ring in which an aromatic and aliphatic ring are condensed, such as isoindoline, and a heteroatom is included. The heteroaryl group is also included in the scope of the heterocycle. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group can be monocyclic or polycyclic.

In this specification, a ring refers to an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocycle.

In this specification, a hydrocarbon ring is a general term for a ring composed of carbon and hydrogen. Types of hydrocarbon rings include, but are not limited to, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a hydrocarbon ring in which an aliphatic and an aromatic are condensed with each other.

In this specification, the aromatic hydrocarbon ring has the same definition as the aryl group, except that it is not monovalent.

In the present specification, the aliphatic hydrocarbon ring includes a hydrocarbon ring having a single bond, a hydrocarbon ring including multiple bonds, or a ring in which rings including single bonds and multiple bonds are condensed. Therefore, among the aliphatic hydrocarbon rings, a ring formed by a single bond includes the cycloalkyl group. A hydrocarbon ring such as cyclohexene that includes a single bond and a double bond but is not an aromatic ring also belongs to the aliphatic hydrocarbon ring.

In the present specification, a heterocycle includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups, except that it is not monovalent.

In this specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

In this specification, the aliphatic hydrocarbon ring group is defined as the aliphatic hydrocarbon ring group, except that it is monovalent.

In this specification, the description of the aryl group described above may be applied, except that the arylene group is divalent.

In this specification, the chemical formula 1 is represented as chemical formula 1-1.

[Chemical Formula 1-1]

In the above chemical formula 1-1, the definitions of R1 to R3, L1 to L3, Ar1, Ar2, and p to r are as defined in chemical formula 1.

In this specification, the chemical formula 1 is represented by the following chemical formula 1-2.

[Chemical Formula 1-2]

In the above chemical formula 1-2, the definitions of R2, R3, L1 to L3, Ar1, Ar2, and p to r are as defined in chemical formula 1,

R11 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group,

r11 is an integer from 1 to 5, and when r11 is 2 or greater, R11 are equal to or different from each other.

In one embodiment of the present specification, R1 is a substituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R1 is a substituted aryl group having 6 to 30 carbon atoms; an amine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, R1 is an aryl group having 6 to 30 carbon atoms substituted with an alkyl group having 1 to 10 carbon atoms; an amine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, R1 is an aryl group having 6 to 20 carbon atoms substituted with an alkyl group having 1 to 5 carbon atoms; an amine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, R1 is an aryl group having 6 to 15 carbon atoms substituted with an alkyl group having 1 to 5 carbon atoms; an amine group substituted or unsubstituted with an aryl group having 6 to 15 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms.

In one embodiment of the present specification, R1 is a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms; a biphenyl group substituted with an alkyl group having 1 to 5 carbon atoms; a naphthyl group substituted with an alkyl group having 1 to 5 carbon atoms; a terphenyl group substituted with an alkyl group having 1 to 5 carbon atoms; a phenyl group having 6 to 20 carbon atoms; a fluorene group unsubstituted or substituted with an alkyl group having 1 to 5 carbon atoms; a dibenzofuran group; a tetrahydronaphthalene group unsubstituted or substituted with an alkyl group having 1 to 5 carbon atoms; or an amine group substituted with an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 is a phenyl group substituted with a methyl group or a terbutyl group; a tetrahydronaphthalene group substituted with a methyl group or a terbutyl group; a fluorene group substituted with a methyl group; an amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; or a dibenzofuran group.

In one embodiment of the present specification, R1 is a phenyl group substituted with a methyl group or a terbutyl group; a tetrahydronaphthalene group substituted with a methyl group; a fluorene group substituted with a methyl group; an amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; or a dibenzofuran group.

In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R11 is a methyl group or a terbutyl group.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 7 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents an alkyl group having 1 to 7 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently is an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 15 carbon atoms.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently a methyl group, an ethyl group, an isopropyl group, a terbutyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, or a triphenylene group.

In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represents a methyl group or a phenyl group.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 15 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or a phenylene group.

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present specification, L3 is a direct bond.

In one embodiment of the present specification, L1 is a phenylene group.

In one embodiment of the present specification, L2 is a phenylene group.

In one embodiment of the present specification, L3 is a phenylene group.

In one embodiment of the present specification, L1 to L3 are direct bonds.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring formed by condensation of these.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms formed by condensation of these groups.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted hydrocarbon ring in which a cycloalkyl group having 3 to 20 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted hydrocarbon ring group in which a cycloalkyl group having 3 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed; or a heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted hydrocarbon ring group in which a cycloalkyl group having 3 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed; or a heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group unsubstituted or substituted with a terbutyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a fluorene group substituted with a methyl group or a phenyl group; a biphenyl group unsubstituted or substituted with a terbutyl group; a terphenyl group; a dibenzofuran group; or a dibenzothiophene group.

In this specification, the chemical formula 2 is represented by the following chemical formula 2-1.

[Chemical Formula 2-1]

In the above chemical formula 2-1, R8, R9, L4, L5, Ar3, Ar4, e, f, s and t are as defined in the above chemical formula 2.

In one embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

In one embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represent hydrogen, deuterium, a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present specification, R8 and R9 are hydrogen.

In one embodiment of the present specification, R8 and R9 are a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present specification, R8 is hydrogen, and R9 is a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present specification, R9 is hydrogen, and R8 is a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present specification, R8 is hydrogen and R9 is a phenyl group.

In one embodiment of the present specification, R9 is hydrogen and R8 is a phenyl group.

In one embodiment of the present specification, R6 and R7 are hydrogen.

In one embodiment of the present specification, L4 and L5 are the same as or different from each other, and each independently represent a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

In one embodiment of the present specification, L4 and L5 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent naphthalene group.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring formed by condensation of these.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms formed by condensation of these groups.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted hydrocarbon ring in which a cycloalkyl group having 3 to 20 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represent an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted hydrocarbon ring group in which a cycloalkyl group having 3 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed; or a heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represent an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted hydrocarbon ring group in which a cycloalkyl group having 3 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms are condensed; or a heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a phenyl group unsubstituted or substituted with a terbutyl group; a tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a fluorene group substituted with a methyl group or a phenyl group; a biphenyl group unsubstituted or substituted with a terbutyl group; a terphenyl group; a dibenzofuran group; or a dibenzothiophene group.

According to one embodiment of the present specification, the compound of chemical formula 1 is any one of the following compounds.

The above Dn-Dm means that the number of deuterium atoms substituted in the compound in parentheses is n to m.

According to one embodiment of the present specification, the compound of chemical formula 2 is any one of the following compounds.

The above Dn-Dm means that the number of deuterium atoms substituted in the compound in parentheses is n to m.

The substituents of the compounds of the above chemical formulas 1 and 2 can be combined by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art.

In addition, by introducing various substituents into the core structure having the structure as described above, it is possible to synthesize a compound having the unique characteristics of the introduced substituent. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material satisfying the conditions required for each organic layer.

The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

The organic layer of the organic light-emitting device of the present invention may be formed of a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

In the organic light-emitting device of the present invention, the organic layer may include at least one layer among an electron transport layer, an electron injection layer, and a layer that simultaneously injects electrons and transports electrons, and at least one layer among the layers may include a compound represented by the chemical formula 1 or 2.

In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1 or 2.

In the organic light-emitting device of the present invention, the organic layer may include at least one layer selected from a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers may include a compound represented by the chemical formula 1 or 2.

In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1 or 2.

In one embodiment of the present specification, the second organic layer is located between the first organic layer and the light-emitting layer.

In one embodiment of the present specification, the first organic layer and the second organic layer are in contact with each other.

In one embodiment of the present specification, an additional layer is laminated between the first organic layer and the second organic layer.

In one embodiment of the present specification, the first organic layer is a first hole transport layer, and the second organic layer is a second hole transport layer.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode

The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

FIG. 1 illustrates the structure of an organic light-emitting device in which an anode (2), a first hole transport layer (3), a second hole transport layer (4), a light-emitting layer (5), and a second electrode (6) are sequentially laminated on a substrate (1).

FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a first hole transport layer (6), a second hole transport layer (7), an emission layer (8), a hole suppression layer (9), an electron injection and transport layer (10), and a second electrode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 may be included in the first hole transport layer (5) or the second hole transport layer (6).

Preferably, the compound of the chemical formula 1 is included in the first hole transport layer, and the compound of the chemical formula 2 is included in the second hole transport layer.

When the compound of the above chemical formula 1 is used in the first hole transport layer closer to the anode, and the compound of the above chemical formula 2 is used in the second hole transport layer closer to the light-emitting layer, the hole transport characteristics of the device can be effectively controlled by controlling the energy barrier from the anode to the light-emitting layer.

For example, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, an emission layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and then depositing a material that can be used as a cathode thereon. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

Additionally, the organic layer can be manufactured in a smaller number of layers by using various polymer materials and solvent processes other than deposition methods, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is preferably used so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

The above cathode is an electrode that injects electrons, and it is preferable that the cathode material be a material having a low work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF/Al or LiO ₂ /Al.

The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers of polyaniline and polythiophene-based compounds. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the above hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and when it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[chemical formula HI-1]

In the above chemical formula HI-1,

At least one of X'1 to X'6 is N, and the rest are CH,

R309 to R314 are the same or different, and are each independently hydrogen; deuterium; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, X'1 to X'6 are N.

According to one embodiment of the present specification, R309 to R314 are nitrile groups.

According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

The above-mentioned hole transport layer can play a role in facilitating the transport of holes. As a hole transport material, a material that can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer is suitable, and a material with high mobility for holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the aforementioned spiro compound or a material known in the art.

The above-described light-emitting layer can emit red, green or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-described light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer respectively and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

The host material of the light-emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound includes, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1.

[Chemical formula H-1]

In the above chemical formula H-1,

L20 and L21 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

Ar20 and Ar21 are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

r201 is an integer from 1 to 8, and when r201 is 2 or more, two or more R201 are the same as or different from each other.

In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group.

According to one embodiment of the present specification, R201 is hydrogen.

According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

When the emitting layer emits red light, the emitting dopant may include, but is not limited to, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum). When the emitting layer emits green light, the emitting dopant may include, but is not limited to, a phosphorescent material such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymers, or PPV polymers can be used as the emitting dopant, but is not limited thereto.

According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[Chemical Formula D-1]

In the above chemical formula D-1,

T1 to T6 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

t5 and t6 are integers from 1 to 4, respectively.

If the above t5 is 2 or more, the above 2 or more T5 are equal to or different from each other,

When the above t6 is 2 or more, the two or more T6 are equal to or different from each other.

According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a nitrile group, or a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a linear or branched heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently a phenyl group; or a dibenzofuran group.

According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

A hole-suppressing layer may be provided between the electron transport layer and the light-emitting layer, and a material known in the art may be used.

The above hole suppression layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

According to one embodiment of the present specification, the hole suppression layer includes, but is not limited to, a compound of the following chemical formula ET-1.

[Chemical formula HB-1]

In the above chemical formula HB-1,

At least one of Z11 to Z13 is N, and the others are CH,

L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar601 to Ar603 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

l601 is an integer from 1 to 5, and when l601 is 2 or more, 2 or more L601 are equal to or different from each other.

According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, the L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

According to one embodiment of the present specification, Ar603 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar603 is a phenyl group, a naphthyl group, or a triphenylene group.

According to one embodiment of the present specification, Ar603 is a triphenylene group.

According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can well inject electrons from the cathode and transfer them to the light-emitting layer and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer can be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage of being able to prevent the electron transport characteristics from being deteriorated, and when it is 50 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of electrons due to the thickness of the electron transport layer being too thick.

The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an excellent electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or the light-emitting material, preventing movement of excitons generated in the light-emitting layer to the hole injection layer, and excellent thin film forming ability is preferable. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

The above electron injection and transport layer facilitates electron injection and transport, and materials known in the art can be used.

According to one embodiment of the present specification, the electron injection and transport layer may include a metal complex and an organic compound together, and when included together, include them in a mass ratio of 1:10 to 10:1.

According to one embodiment of the present disclosure, the electron injection and transport layer includes, but is not limited to, a compound of the following chemical formula ET-1.

[chemical formula ET-1]

In the above chemical formula ET-1,

At least one of Z11 to Z13 is N, and the others are CH,

L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar601 to Ar603 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

l601 is an integer from 1 to 5, and when l601 is 2 or more, 2 or more L601 are equal to or different from each other.

According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, the L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

According to one embodiment of the present specification, the Ar603 is a heteroaryl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar603 is a heteroaryl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, Ar603 is a triazine group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

As the above metal complex compounds, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that two or more organic layers are formed using the above-described compound.

The method for producing the compounds of the above chemical formulas 1 and 2 and the production of organic light-emitting devices using them are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

In the following reaction formula, the type and number of substituents can be selected appropriately by those skilled in the art from known starting materials to synthesize various types of intermediates. The reaction type and reaction conditions known in the art can be used.

By appropriately combining the manufacturing formulas and the intermediates described in the examples of this specification based on common technical knowledge, all of the compounds of chemical formulas 1 and 2 described in this specification can be manufactured.

<Chemical Formula 1 Synthesis Example>

Synthesis Example A-1. Synthesis of Compound A-1

To a solution of N -([1,1'-biphenyl]-4-yl)-3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 33.07 mmol), bromobenzene (5.30 g, 33.73 mmol), and sodium tert-butoxide (4.45 g, 46.30 mmol) was added toluene (150 ml), and the mixture was stirred and heated for 10 minutes. To the mixture was added bis(tri-tert-butylphosphine)palladium (0.08 g, 0.17 mmol) dissolved in toluene (10 ml), and the mixture was stirred and heated for 1 hour. After completion of the reaction and filtration, the layer was separated into toluene and water. After removal of the solvent, the compound A-1 (18.0 g, 79.94% yield) was obtained by recrystallization from ethyl acetate. (MS[M+H]+ = 681)

Synthesis Example A-2. Synthesis of Compound A-2

Compound A-2 (20.0 g, 79.89% yield) was obtained in the same manner as in Synthetic Example A -1 using N -([1,1'-biphenyl]-4-yl)-3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 33.07 mmol) and 4-bromo-1,1'-biphenyl (7.86 g, 33.73 mmol). (MS[M+H]+ = 757)

Synthesis Example A-3. Synthesis of Compound A-3

Compound A-3 (19.0 g, 78.60% yield) was obtained using the same method as in Synthetic Example A -1 using N -([1,1'-biphenyl]-4-yl)-3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 33.07 mmol) and 1-bromonaphthalene (6.98 g, 33.73 mmol). (MS[M+H]+ = 731)

Synthesis Example A-4. Synthesis of Compound A-4

Compound A-4 (20.0 g, 78.44% yield) was obtained using N -([1,1'-biphenyl]-4-yl)-3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 33.07 mmol) and 4-bromodibenzo[ b , d ]furan (8.33 g, 33.73 mmol) in the same manner as in Synthetic Example A-1. (MS[M+H]+ = 771)

Synthesis Example A-5. Synthesis of Compound A-5

To a solution of 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 44.19 mmol), 1-bromo-4-( tert -butyl)benzene (19.31 g, 90.59 mmol) and sodium tert-butoxide (11.89 g, 123.37 mmol) was added toluene (150 ml), and the mixture was stirred and heated for 10 minutes. To the mixture was added bis(tri-tert-butylphosphine)palladium (0.23 g, 0.44 mmol) dissolved in toluene (10 ml), and the mixture was stirred and heated for 1 hour. After completion of the reaction and filtration, the layers were separated into toluene and water. After removal of the solvent, the compound A-5 (25.0 g, 78.90% yield) was obtained by recrystallization from ethyl acetate. (MS[M+H]+ = 717)

Synthesis Example A-6. Synthesis of Compound A-6

Compound A-6 (29.0 g, 79.53% yield) was obtained using the same method as in Synthetic Example A-5 using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 44.19 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (26.61 g, 90.59 mmol). (MS[M+H]+ = 825)

Synthesis Example A-7. Synthesis of Compound A-7

Compound A-7 (22.5 g, 77.13% yield) was obtained using the same method as in Synthetic Example A-5 using 3-(4-(diphenylamino)phenyl)-9,9-diphenyl-9 H -fluoren-2-amine (20.0 g, 34.68 mmol) and 1-bromo-4-( tert -butyl)benzene (15.15 g, 71.09 mmol). (MS[M+H]+ = 841)

Synthesis Example A-8. Synthesis of Compound A-8

Using 3-(4-(diphenylamino)phenyl)-9,9-diphenyl-9 H -fluoren-2-amine (20.0 g, 34.68 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (19.00 g, 71.09 mmol), compound A-8 (25.5 g, 77.45% yield) was obtained in the same manner as in Synthetic Example A-5. (MS[M+H]+ = 949)

Synthesis Example A-9. Synthesis of Compound A-9

Compound A-9 (28.5 g, 78.69% yield) was obtained using the same method as in Synthetic Example A-5 using 3-(dibenzo[ b , d ]furan-4-yl)-9,9-dimethyl- 9H -fluoren-2-amine (20.0 g, 53.27 mmol) and 4-bromo-1,1'-biphenyl (25.45 g, 109.20 mmol). (MS[M+H]+ = 680)

Synthesis Example A-10. Synthesis of Compound A-10

Using 3-(4-( tert -butyl)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 58.57 mmol) and 4-bromo-1,1'-biphenyl (27.99 g, 120.06 mmol), compound A-10 (29.5 g, 77.98% yield) was obtained in the same manner as in Synthetic Example A-5. (MS[M+H]+ = 646)

Synthesis Example A-11. Synthesis of Compound A-11

Using 3-(4-( tert -butyl)phenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 58.57 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (32.08 g, 120.06 mmol), compound A-11 (33.0 g, 78.90% yield) was obtained in the same manner as in Synthetic Example A-5. (MS[M+H]+ = 714)

Synthesis Example A-12. Synthesis of Compound A-12

Using 3-(3,5-di- tert -butylphenyl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 50.30 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (27.55 g, 103.12 mmol), compound A-12 (30.5 g, 78.73% yield) was obtained in the same manner as in Synthetic Example A-5. (MS[M+H]+ = 770)

Synthesis Example A-13. Synthesis of Compound A-13

Compound A-13 (28.0 g, 79.12% yield) was obtained using the same method as in Synthetic Example A-5 using 9,9-dimethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9 H -fluoren-2-amine (20.0 g, 50.56 mmol) and 4-bromo-1,1'-biphenyl (24.16 g, 103.64 mmol). (MS[M+H]+ = 700)

Synthesis Example A-14. Synthesis of Compound A-14

Compound A-2 (20.0 g, 26.42 mmol) obtained in the above Synthetic Example A-2 was added to benzene-d6 (200 ml) and completely dissolved, then trifluoromethanesulfonic acid (1.2 ml, 13.21 mmol) was added and stirred for 25 minutes. After completion of the reaction, dichloromethane was added, the layers were separated, and the organic layer was obtained. It was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain the compound 14 (16.0 g, 76.93%). (MS[M+H]+ = 787)

Synthesis Example A-15. Synthesis of Compound A-15

Compound A-15 (16.0 g, 77.22% yield) was obtained using the compound A-7 (20.0 g, 23.78 mmol) obtained in the above Synthesis Example A-7 in the same manner as in the above Synthesis Example A-14. (MS[M+H]+ = 871)

Synthesis Example B-1. Synthesis of Compound B-1

To a mixture of 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol), N -([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine (22.92 g, 57.65 mmol) and sodium tert-butoxide (7.60 g, 79.13 mmol) was added toluene (150 ml), and the mixture was stirred and heated for 10 minutes. To the mixture was added bis(tri-tert-butylphosphine)palladium (0.15 g, 0.28 mmol) dissolved in toluene (10 ml), and the mixture was stirred and heated for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, the compound B-1 (32.0 g, 79.19% yield) was obtained by recrystallization from ethyl acetate. (MS[M+H]+ = 715)

Synthesis Example B-2. Synthesis of Compound B-2

Compound B-2 (34.0 g, 78.64% yield) was obtained in the same manner as in Synthetic Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and N -([1,1'-biphenyl]-4-yl)-4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-amine (25.80 g, 57.65 mmol). (MS[M+H]+ = 765)

Synthesis Example B-3. Synthesis of Compound B-3

Compound B-3 (34.0 g, 78.64% yield) was obtained in the same manner as in Synthetic Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and N -(3-(naphthalen-1-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine (25.80 g, 57.65 mmol). (MS[M+H]+ = 765)

Synthesis Example B-4. Synthesis of Compound B-4

Compound B-4 (33.0 g, 79.01% yield) was obtained using the same method as in Synthesis Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and N -(3-(phenanthren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)

Synthesis Example B-5. Synthesis of Compound B-5

Compound B-5 (33.0 g, 79.01% yield) was obtained using the same method as in Synthesis Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and bis(4-(naphthalen-1-yl)phenyl)amine (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)

Synthesis Example B-6. Synthesis of Compound B-6

Compound B-6 (33.5 g, 80.21% yield) was obtained using the same method as in Synthetic Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and 3-(naphthalen-1-yl)- N -(4-(naphthalen-1-yl)phenyl)aniline (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)

Synthesis Example B-7. Synthesis of Compound B-7

Compound B-7 (32.5 g, 77.82% yield) was obtained using the same method as in Synthetic Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and 4-(naphthalen-1-yl)- N -(4-(naphthalen-2-yl)phenyl)aniline (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)

Synthesis Example B-8. Synthesis of Compound B-8

Compound B-8 (32.0 g, 77.67% yield) was obtained using the same method as in Synthesis Example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and N -([1,1':4',1''-terphenyl]-4-yl)dibenzo[ b , d ]-furan-4-amine (23.72 g, 57.65 mmol). (MS[M+H]+ = 729)

Synthesis Example B-9. Synthesis of Compound B-9

Compound B-9 (28.0 g, 78.68% yield) was obtained using the same method as in Synthesis Example B-1 using 9-(4'-chloro-[1,1':3',1''-terphenyl]-2-yl)-9 H -carbazole (20.0 g, 46.52 mmol) and N -(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol). (MS[M+H]+ = 765)

Synthesis Example B-10. Synthesis of Compound B-10

Compound B -10 (28.5 g, 80.09% yield) was obtained using the same method as in Synthesis Example B-1, using 9-(4'-chloro-[1,1':2',1''-terphenyl]-2-yl)-9 H -carbazole (20.0 g, 46.52 mmol) and N -(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol). (MS[M+H]+ = 765)

Synthesis Example B-11. Synthesis of Compound B-11

Compound B-11 (16.5 g, 79.25% yield) was obtained using the compound B-4 (20.0 g, 27.07 mmol) obtained in the above Synthesis Example B-4 in the same manner as in the above Synthesis Example A-14. (MS[M+H]+ = 769)

Synthesis Example B-12. Synthesis of Compound B-12

Compound B-12 (16.5 g, 79.25% yield) was obtained using the compound B-6 (20.0 g, 27.07 mmol) obtained in the above Synthesis Example B-6 in the same manner as in the above Synthesis Example A-14. (MS[M+H]+ = 769)

<Experimental examples and comparative experimental examples>

Experimental Example 1

A glass substrate coated with a 1,400Å thick ITO (Indium Tin Oxide) thin film was placed in distilled water containing a detergent and cleaned using ultrasonic waves. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, the substrate was transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum deposition device.

On the ITO transparent electrode thus prepared, a compound represented by the chemical formula HAT below was thermally vacuum deposited to a thickness of 100Å to form a hole injection layer. Thereon, compound A-1 prepared in Synthesis Example A-1 was vacuum deposited to a thickness of 1150Å as a first hole transport layer, and then compound B-1 prepared in Synthesis Example B-1 was thermally vacuum deposited to a thickness of 50Å as a second hole transport layer. Subsequently, a compound represented by the chemical formula BH below and a compound represented by the chemical formula BD below were vacuum deposited at a weight ratio of 50:1 to a thickness of 200Å as an emitting layer. Subsequently, a compound represented by the chemical formula HB below was vacuum deposited to a thickness of 50Å as a hole blocking layer. Subsequently, a compound represented by the chemical formula ET below and a compound represented by the chemical formula Liq below were thermally vacuum deposited at a weight ratio of 1:1 to a thickness of 310Å as a layer performing both electron transport and electron injection. An organic light-emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron transport and electron injection layers to form a cathode.

Experimental examples 2 to 103 and comparative examples 1 to 58

Except that the compound described in Table 1 was used instead of Compound A-1 in the first hole transport layer and the compound described in Table 1 was used instead of Compound B-1 in the second hole transport layer, organic light-emitting devices of Experimental Examples 2 to 103 and Comparative Examples 1 to 58 were manufactured in the same manner as Experimental Example 1. When a current of 10 mA/cm ² was applied to the organic light-emitting devices manufactured in the Experimental Examples and Comparative Examples, the voltage, efficiency, color coordinates, and lifespan were measured and the results are shown in Table 1 below. Meanwhile, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

Comparative Examples 1 to 4 include only one of a layer including a compound of Chemical Formula 1 and a layer including a compound of Chemical Formula 2.

It can be confirmed that Examples 1 to 103, in which the compound of Chemical Formula 1 is used in the first hole transport layer closer to the anode, and the compound of Chemical Formula 2 is used in the second hole transport layer closer to the light-emitting layer, have the effects of lower voltage, higher efficiency, and longer life than Comparative Examples 1 to 4.

Comparative Examples 5 to 28, unlike the compound of Chemical Formula 2 of the present invention, do not form an ortho bond between the nitrogen of carbazole and the amine group, or the linker is bonded to the benzene ring of carbazole.

In the case of Examples 1 to 103, where the linker between the nitrogen and the amine group of the carbazole forms an ortho bond as in the chemical formula 2 above, it can be confirmed that the effects of low voltage, high efficiency, and long life are achieved compared to Comparative Examples 5 to 28.

Comparative Examples 29 to 58 used compounds in which R1 was hydrogen or an unsubstituted aryl group, unlike the compound of chemical formula 1 of the present invention.

It can be confirmed that Examples 1 to 103 using a compound in which R1 of the above chemical formula 1 is an aryl group substituted with an alkyl group or an amine group, a condensed hydrocarbon ring group substituted with an alkyl group, or a heteroaryl group have the effects of low voltage, high efficiency, and long life compared to Comparative Examples 29 to 58.

As shown in Table 1 above, it was confirmed that the organic light-emitting device in which the compound represented by the chemical formula 1 of the present invention was used as the first hole transport layer and the compound represented by the chemical formula 2 was used as the second hole transport layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

1: Substrate
2: Bipolar
3: Organic layer
4: Negative
5: Hole injection layer
6: First hole transport layer
7: Second hole transport layer
8: Emitting layer
9: Hole suppression layer
10: Electron injection and transport layer

Claims (11)

anode;
cathode;
A light-emitting layer provided between the anode and the cathode;
A first organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 1; and
An organic light-emitting device comprising a second organic layer provided between the anode and the light-emitting layer and including a compound of the following chemical formula 2:
[Chemical Formula 1]

[Chemical formula 2]

In the above chemical formulas 1 and 2,
Ar1 to Ar4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted ring formed by condensation of these groups,
R4 to R9 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group,
R1 is a substituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in which an aromatic ring and an aliphatic ring are condensed,
R2 and R3 are the same or different, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
L1 to L5 are the same or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,
a and c to f are integers from 0 to 4, respectively,
b is an integer from 0 to 2,
When a to f are 2 or more, R4 to R9 are each the same or different;
p and t are integers from 0 to 2, respectively. In claim 1, the chemical formula 1 is an organic light-emitting device represented by the following chemical formula 1-1:
[Chemical Formula 1-1]

In the above chemical formula 1-1, the definitions of R1 to R3, L1 to L3, Ar1, Ar2, and p to r are as defined in chemical formula 1. In claim 1, the chemical formula 1 is an organic light-emitting device represented by the following chemical formula 1-2:
[Chemical Formula 1-2]

In the above chemical formula 1-2, the definitions of R2, R3, L1 to L3, Ar1, Ar2, and p to r are as defined in chemical formula 1,
R11 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted heteroaryl group,
r11 is an integer from 1 to 5, and when r11 is 2 or greater, R11 are equal to or different from each other. In claim 1, the chemical formula 2 is an organic light-emitting device represented by the following chemical formula 2-1:
[Chemical Formula 2-1]

In the above chemical formula 2-1, R8, R9, L4, L5, Ar3, Ar4, e, f, s and t are as defined in the above chemical formula 2. An organic light-emitting device according to claim 1, wherein R8 and R9 are the same as or different from each other, and each independently represents a phenyl group, a naphthyl group, or a biphenyl group. In claim 1, an organic light-emitting device wherein the chemical formula 1 is any one of the following compounds:














The above Dn-Dm means that the number of deuterium atoms substituted in the compound in parentheses is n to m. In claim 1,
The compound represented by the above chemical formula 2 is an organic light-emitting device represented by any one of the following structures:






















The above Dn-Dm means that the number of deuterium atoms substituted in the compound in parentheses is n to m. An organic light-emitting device according to claim 1, wherein the second organic layer is in contact with the light-emitting layer. An organic light-emitting device according to claim 1, wherein the first organic layer and the second organic layer are in contact with each other. An organic light-emitting device according to claim 1, wherein an additional layer is laminated between the first organic layer and the second organic layer. An organic light-emitting device according to claim 1, wherein the first organic layer is a first hole transport layer, and the second organic layer is a second hole transport layer.