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WO2018164265A1 - Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Download PDF

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WO2018164265A1
WO2018164265A1 PCT/JP2018/009247 JP2018009247W WO2018164265A1 WO 2018164265 A1 WO2018164265 A1 WO 2018164265A1 JP 2018009247 W JP2018009247 W JP 2018009247W WO 2018164265 A1 WO2018164265 A1 WO 2018164265A1
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匡 羽毛田
裕勝 伊藤
裕 工藤
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence element containing the compound, an organic electroluminescence element using the compound, and an electronic device including the organic electroluminescence element.
  • an organic electroluminescence element (organic EL element) is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode.
  • organic EL element When a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state, which is excited. Light is emitted when the state returns to the ground state. Therefore, the development of a compound that efficiently transports electrons or holes to the light emitting region and facilitates recombination of electrons and holes is important in obtaining a high-efficiency organic EL device.
  • Patent Document 1 discloses an amine compound in which a spirobifluorene structure is bonded to a central nitrogen atom directly or via an aromatic ring. Patent Document 1 describes that this compound is suitable as a hole transport material in a hole transport layer or an exciton blocking layer or as a matrix material in a light emitting layer.
  • Patent Document 2 discloses an amine compound in which a 9,9-disubstituted fluorene structure such as a 9,9-diphenylfluorene structure or a 9,9-dimethylfluorene structure is bonded to a central nitrogen atom directly or via an aromatic ring. ing. Patent Document 2 describes that this compound is suitable as a hole transport material and / or a hole injection material in a hole transport layer or an exciton blocking layer, or as a matrix material in a light emitting layer.
  • the present invention has been made to solve the above-described problems, and an object of the present invention is to provide an organic EL element exhibiting excellent luminous efficiency and a novel compound that realizes such an organic EL element.
  • the present inventors realize an organic EL device in which a compound represented by the following formula (1) having a spiroanthracenefluorene skeleton exhibits excellent luminous efficiency. I found.
  • the present invention provides a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)).
  • compound (1) a compound represented by formula (1)
  • R 1 to R 8 and R 11 to R 18 are each independently a hydrogen atom or a substituent
  • two adjacent groups selected from R 1 to R 4 two adjacent groups selected from R 5 to R 8
  • Two adjacent groups selected from R 11 to R 14 and two adjacent groups selected from R 15 to R 18 may be bonded to each other to form a ring structure.
  • one selected from R 1 to R 8 and R 11 to R 18 represents a single bond bonded to *, or the ring-forming atom of the ring structure is bonded to *.
  • R 21 and R 22 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 ring. It is a heteroaryl group having 5 to 30 atoms.
  • L 1 , L 2 , and L 3 are each independently a single bond, 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. It is.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms, or substituted or unsubstituted.
  • the substituent represented by R 1 to R 8 and R 11 to R 18 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted Unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted ring carbon number 6 A mono-, di- or tri-substituted sily
  • the present invention provides a material for an organic electroluminescence device comprising the compound (1).
  • the present invention is an organic electroluminescent device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a light-emitting layer,
  • an organic electroluminescence device in which at least one layer contains a compound (1).
  • the present invention provides an electronic device comprising the organic electroluminescence element.
  • Compound (1) realizes an organic EL device with further improved luminous efficiency.
  • carbon number XX to YY of “substituted or unsubstituted ZZ group having XX to YY” represents the carbon number of unsubstituted ZZ group and does not include the carbon number of the substituent.
  • atom number XX to YY of “substituted or unsubstituted ZZ group having XX to YY” represents the number of atoms of the unsubstituted ZZ group and does not include the number of atoms of the substituent.
  • the “unsubstituted ZZ group” of the “substituted or unsubstituted ZZ group” means that the hydrogen atom of the ZZ group is not substituted with a substituent.
  • hydroxogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • the “ring-forming carbon number” refers to a carbon that forms the ring itself of a compound in which atoms are bonded cyclically, for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound. Represents the number of atoms. When the ring has a substituent, the carbon atom contained in the substituent is not included in the ring-forming carbon atom. The same applies to the “ring carbon number” described below unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • the carbon atom of the alkyl substituent is not included in the ring-forming carbon atom.
  • the carbon atom of the fluorene substituent is not included in the ring-forming carbon atom.
  • the “number of ring-forming atoms” refers to an atom that forms the ring itself of a compound in which atoms are bonded in a ring, for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound. Represents the number of An atom that does not form a ring, for example, a hydrogen atom bonded to an atom forming a ring and an atom included in a substituent bonded to an atom forming a ring are not included in the ring forming atom. The same applies to the “number of ring-forming atoms” described below unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • Hydrogen atoms and substituent atoms bonded to ring-forming carbon atoms of the pyridine ring or quinazoline ring are not included in the ring-forming atoms.
  • the atom of the fluorene substituent is not included in the ring-forming atom.
  • the compound (compound (1)) according to one embodiment of the present invention is represented by the formula (1).
  • one selected from R 1 to R 8 and R 11 to R 18 represents a single bond bonded to *. Further, two adjacent members selected from R 1 to R 4, two adjacent members selected from R 5 to R 8, two adjacent members selected from R 11 to R 14 , and R 15 to R 18 are selected. Two adjacent groups may be bonded to each other to form a ring structure, and a ring-forming atom of the ring structure may be bonded to *.
  • the compound (1) includes a compound represented by any one of the formulas (2) to (13).
  • R 1 to R 5 , R 8 and R 11 to R 18 represents a single bond bonded to *, or the ring-forming atom of ring structure A is bonded to *.
  • R 1 to R 4 , R 7 , R 8 , and R 11 to R 18 represents a single bond bonded to *, or the ring-forming atom of ring structure B is bonded to * To do.
  • R 1 , R 4 , R 5 , R 8 , and R 11 to R 18 represents a single bond bonded to *, or the ring-forming atom of the ring structure A or C is * To join.
  • R 1 to R 8 , R 11 to R 15 and R 18 represents a single bond bonded to *, or a ring-forming atom of ring structure D is bonded to *.
  • R 1 to R 8 and R 11 to R 18 which do not represent a single bond bonded to * and do not form the ring structure are each independently a hydrogen atom or a substituent.
  • the substituent is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; a substituted or unsubstituted carbon group having 3 to 30 ring carbon atoms, preferably 3 to 10 carbon atoms; More preferably 3 to 8, more preferably 5 or 6 cycloalkyl group; substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; Substituted heteroaryl group having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms; substituted or unsubstituted 7 to 36, preferably 7 to 26, more preferably 7 to 20 carbon atoms A substituted or unsubstitute
  • the alkyl group is, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (including isomer group), hexyl group (including isomer group), heptyl group (including isomer group), octyl group (including isomer group), nonyl group (isomer) Group), decyl group (including isomer group), undecyl group (including isomer group), or dodecyl group (including isomer group); methyl group, ethyl group, n-propyl group, isopropyl Group, n-butyl group, isobutyl group, s-butyl group, t-butyl group and pentyl group (
  • the cycloalkyl group is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, A cyclohexyl group is preferred.
  • the aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, a biphenylenyl group, a fluorenyl group, or an s-indacenyl group.
  • the substituted aryl group for example, a 9,9-dimethylfluorenyl group, a 9,9-diphenylflu
  • the heteroaryl group contains 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms.
  • the ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom and an oxygen atom.
  • the free valence of the heteroaryl group may be present on the ring-forming carbon atom or, if structurally possible, on the ring-forming nitrogen atom.
  • the heteroaryl group is, for example, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, Pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzoimidazolyl group, indazolyl group, phenanthrolinyl group Phenanthridinyl group, acri
  • substituted heteroaryl group examples include 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, and diphenylcarbazol-9-yl.
  • Group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group (phenyldibenzothienyl group) are preferred.
  • the aryl moiety of the aralkyl group is selected from the above aryl groups having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms.
  • the alkyl moiety corresponds to a group selected from the above substituted or unsubstituted alkyl groups having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms.
  • aralkyl group a benzyl group, a phenethyl group, and a phenylpropyl group are preferable, and a benzyl group is more preferable.
  • the alkyl portion of the alkoxy group is the above substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms. Selected from.
  • the alkoxy group a t-butoxy group, a propoxy group, an ethoxy group, and a methoxy group are preferable, an ethoxy group and a methoxy group are more preferable, and a methoxy group is further preferable.
  • the aryl moiety of the aryloxy group has the above substituted or unsubstituted ring carbon number of 6 to 30, preferably 6 to 25, more preferably. Selected from 6-18 aryl groups.
  • a terphenyloxy group, a biphenyloxy group, and a phenoxy group are preferable, a biphenyloxy group and a phenoxy group are more preferable, and a phenoxy group is more preferable.
  • the mono-, di- or tri-substituted silyl group has a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18, more preferably 1 to 8 carbon atoms, and the above substituted or unsubstituted group.
  • aryl groups having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms.
  • Tri-substituted silyl groups are preferred, for example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, And tolylylsilyl group.
  • the haloalkyl group is at least one, preferably 1 to 1, of the above alkyl groups having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms.
  • the group obtained by substituting seven hydrogen atoms or all the hydrogen atoms with halogen atoms is mentioned.
  • the halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom.
  • the haloalkyl group is preferably a fluoroalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, including a heptafluoropropyl group (including an isomer group), a pentafluoroethyl group, 2,2, A 2-trifluoroethyl group and a trifluoromethyl group are more preferable, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group are more preferable, and a trifluoromethyl group is particularly preferable.
  • the haloalkyl portion of the haloalkoxy group is selected from the above haloalkyl groups having 1 to 30, preferably 1 to 18, and more preferably 1 to 8 carbon atoms.
  • the haloalkoxy group is preferably a fluoroalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, including a heptafluoropropoxy group (including isomer groups), a pentafluoroethoxy group, and 2,2.
  • 1,2-trifluoroethoxy group and trifluoromethoxy group are more preferable, pentafluoroethoxy group, 2,2,2-trifluoroethoxy group and trifluoromethoxy group are more preferable, and trifluoromethoxy group is particularly preferable.
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and a fluorine atom is preferred.
  • R 1 to R 7 and R 11 to R 18 which do not represent the single bond bonded to * and do not form the ring structure are preferably a hydrogen atom, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, respectively.
  • R 1 to R 7 and R 11 to R 18 that do not represent a single bond bonded to * and do not form the ring structure may be all hydrogen atoms.
  • one selected from R 1 to R 7 and R 11 to R 18 may be a single bond bonded to *, and all the remaining may be hydrogen atoms.
  • Two adjacent members selected from R 1 to R 4 , preferably R 2 and R 3 or R 3 and R 4 ; two adjacent members selected from R 5 to R 8 , preferably R 5 and R 6 or R 6 And R 7 ; two adjacent members selected from R 11 to R 14 , preferably two adjacent members selected from R 12 and R 13 ; and R 15 to R 18 , preferably R 16 and R 17 are bonded to each other.
  • R 1 to R 4 preferably R 2 and R 3 or R 3 and R 4
  • two adjacent members selected from R 5 to R 8 preferably R 5 and R 6 or R 6 And R 7
  • two adjacent members selected from R 11 to R 14 preferably two adjacent members selected from R 12 and R 13
  • R 15 to R 18 preferably R 16 and R 17 are bonded to each other.
  • all of the two adjacent groups may not form a ring structure.
  • Examples of the ring structure include substituted or unsubstituted aromatic hydrocarbon rings having 6 to 18 ring carbon atoms, substituted or unsubstituted aliphatic hydrocarbon rings having 5 to 18 ring carbon atoms, substituted or unsubstituted rings. And an aromatic heterocyclic ring having 5 to 18 ring atoms and a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms.
  • the ring structure may be a condensed ring.
  • aromatic hydrocarbon ring having 6 to 18 ring carbon atoms examples include an aromatic hydrocarbon selected from benzene, biphenylene, naphthalene, anthracene, benzoanthracene, phenanthrene, benzophenanthrene, phenalene, pyrene, chrysene, and triphenylene.
  • aromatic hydrocarbon selected from benzene, biphenylene, naphthalene, anthracene, benzoanthracene, phenanthrene, benzophenanthrene, phenalene, pyrene, chrysene, and triphenylene.
  • a ring is mentioned.
  • Examples of the aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms include a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, and the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms.
  • An aliphatic hydrocarbon ring obtained by partial hydrogenation can be mentioned.
  • aromatic heterocyclic ring having 5 to 18 ring atoms examples include pyrrole, furan, thiophene, pyridine, imidazole, pyrazole, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, benzimidazole, indazole, dibenzofuran,
  • An aromatic heterocyclic ring selected from naphthobenzofuran, dibenzothiophene, naphthobenzothiophene, carbazole, and benzocarbazole is exemplified.
  • Examples of the aliphatic heterocyclic ring having 5 to 18 ring atoms include an aliphatic heterocyclic ring obtained by partially hydrogenating the aromatic heterocyclic ring having 5 to 18 ring atoms.
  • the ring structure is preferably a benzene ring.
  • one selected from R 1 to R 8 and R 11 to R 18 is preferably a single bond bonded to *, and is selected from R 2 to R 7 , R 12 , and R 17. More preferably, one is a single bond bonded to *, more preferably one selected from R 2 to R 7 is a single bond bonded to *, R 2 , R 4 , R 5 , and R 7 It is particularly preferred that one selected from is a single bond bonded to *.
  • the ring and the ring-forming atom of the aliphatic heterocyclic ring having 5 to 18 ring-forming atoms may be bonded to *.
  • R 21 and R 22 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, a substituted or unsubstituted carbon atom number 6
  • R 21 and R 22 are preferably not bonded to each other and therefore do not form a ring structure.
  • R 21 and R 22 Details of the respective substituents represented by R 21 and R 22 are the corresponding substitutions described above with respect to R 1 to R 7 and R 11 to R 18 which do not represent a single bond bonded to * and do not form the ring structure. Each group is the same.
  • R 21 and R 22 are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a methyl group, an ethyl group, n -Propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, phenyl group, biphenylyl group, or naphthyl group, more preferably a methyl group or a phenyl group.
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted group.
  • Substituted heteroarylene groups having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms.
  • the arylene group includes, for example, a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, an anthrylene group, a benzoanthrylene group, Phenanthrylene group, benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, triphenylenylene group, fluoranthenylene group, or fluorenylene group; preferably phenylene A group, a biphenylylene group, a terphenylylene group, a naphthylene group, a phenanthrylene group, or a fluorenylene group; more preferably a group selected from the following formula: More
  • the heteroarylene group has 1 to 5, preferably 1 to 3, more preferably 1 to 2 rings.
  • the ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom, and an oxygen atom.
  • the free valence may be present on the ring-forming carbon atom or on the nitrogen atom where structurally possible.
  • heteroarylene group examples include pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isodol Indole, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran, isobenzofuran, dibenzofuran, naphthobenzofuran , Benzothiophene, dibenzothiophene, nap
  • L 1 and L 2 are each preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
  • L 1 and L 2 are preferably a single bond.
  • one of L 1 and L 2 is a single bond, and the other is a substituted or unsubstituted ring.
  • An arylene group having 6 to 30 carbon atoms is preferable, and in another embodiment of the present invention, L 1 and L 2 are each preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. .
  • the arylene group includes, for example, a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, an anthrylene group, a benzoanthrylene group, a phenanthrylene group, Benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, triphenylenylene group, fluoranthenylene group, fluorenylene group, or 9,9'-spirobiflur
  • An oleylene group preferably a phenylene group, a biphenylylene group, a terphenylylene group, or a naphthylene group; more preferably a group selected from the following formulae; More preferably, it
  • the heteroarylene group has 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms.
  • the ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom, and an oxygen atom.
  • the free valence may be present on the ring-forming carbon atom or on the nitrogen atom where structurally possible.
  • heteroarylene group examples include pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isodol Indole, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran, isobenzofuran, dibenzofuran, naphthobenzofuran , Benzothiophene, dibenzothiophene, nap
  • L 3 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. In one embodiment of the present invention, L 3 is preferably a single bond. In another embodiment of the present invention, L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, preferably a phenylene group. Preferably there is.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18; substituted or unsubstituted ring atoms having 5 to An oxygen-containing heteroaryl group of 30, preferably 5 to 24, more preferably 5 to 13; or a sulfur containing 5-30, preferably 5-24, more preferably 5-13, substituted or unsubstituted ring-forming atoms A heteroaryl group;
  • Ar 1 and Ar 2 are preferably each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In another embodiment of the present invention, Ar 1 and Ar 2 are preferably each independently a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms. In still another embodiment of the present invention, Ar 1 and Ar 2 are preferably each independently a substituted or unsubstituted sulfur-containing heteroaryl group having 5 to 30 ring atoms.
  • one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the other is a substituted or unsubstituted ring atom having 5 to 30 ring atoms. It is preferably an oxygen-containing heteroaryl group.
  • one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the other is a substituted or unsubstituted ring atom having 5 to 30 ring atoms. It is preferably a sulfur-containing heteroaryl group.
  • one of Ar 1 and Ar 2 is a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring atom having 5 rings. It is preferably a ⁇ 30 sulfur-containing heteroaryl group.
  • the aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, a biphenylenyl group, a fluorenyl group.
  • -Yl group p-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-phenanthryl group, 9-phenanthryl group, 2-triphenylenyl group, fluoren-2-yl group, or fluorene-4 -An yl group.
  • the substituted aryl group is preferably a 9,9′-spirobifluoren-2-yl group, a 9,9′-spirobifluoren-4-yl group, a 9,9-diphenylfluoren-2-yl group, -Diphenylfluoren-4-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-4-yl group, 10,10-dimethyl (anthracene-9,9'-fluorene) -2 It is a '-yl group or a 10,10-dimethyl (anthracene-9,9'-fluorene) -4'-yl group.
  • the oxygen-containing heteroaryl group is, for example, a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group.
  • Benzofuranyl group isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, or phenoxazinyl group; preferably furyl group, benzofuranyl group, dibenzofuran More preferably a dibenzofuranyl group or a naphthobenzofuranyl group; still more preferably a dibenzofuranyl group; particularly preferably a 1-dibenzofuranyl group, 2- Dibenzofuranyl group or 4-dibenzofuranyl group That.
  • the sulfur-containing heteroaryl group includes, for example, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothio group A phenyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, or a phenothiazinyl group; preferably a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group More preferably a dibenzothiophenyl group or a naphthobenzothiophenyl group; still more preferably a dibenzothiophenyl group
  • L 1 and L 2 are each selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group, and a naphthylene group
  • Ar 1 and Ar 2 are each a phenyl group, a biphenylyl group, a naphthyl group, Fluorenyl group, phenanthryl group, triphenylenyl group, 9,9'-spirobifluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dimethylfluorenyl group, and 10,10-dimethyl (anthracene- It is preferably selected from 9,9′-fluorenyl) yl groups.
  • —L 1 —Ar 1 and —L 2 —Ar 2 are each independently selected from the following groups.
  • an arbitrary substituent referred to as “substituted or unsubstituted” is a substituted or unsubstituted alkyl having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms.
  • the production method of compound (1) is not particularly limited, and those skilled in the art can easily produce the compound (1) by the method described in the following examples or by a method obtained by modifying the method with reference to a known synthesis method. Can do.
  • the organic EL element material of the present invention contains compound (1).
  • the content of the compound (1) in the organic EL device material of the present invention is not particularly limited, and may be, for example, 1% by mass or more (including 100%), and 10% by mass or more (including 100%). It is preferably 50% by mass or more (including 100%), more preferably 80% by mass or more (including 100%), and 90% by mass or more (including 100%). It is particularly preferred that The material for an organic EL device of the present invention is useful for producing an organic EL device.
  • An organic EL element has an organic layer between a cathode and an anode.
  • the organic layer includes a light emitting layer, and at least one of the organic layers includes the compound (1).
  • a hole transport zone (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer. Examples include, but are not limited to, a light emitting layer, a space layer, and an electron transport zone (an electron transport layer, an electron injection layer, a hole blocking layer, etc.) provided between the cathode and the light emitting layer.
  • the compound (1) is used as a material of a hole transport zone or a light emitting layer of a fluorescent or phosphorescent EL device, preferably a material of a hole transport zone, more preferably a material of a hole transport layer.
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used, and a fluorescent light emitting element is preferable.
  • the “light emitting unit” refers to a minimum unit that includes an organic layer, at least one of which is a light emitting layer, and emits light by recombination of injected holes and electrons.
  • typical element configurations of simple organic EL elements include the following element configurations.
  • Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, excitons generated in the phosphorescent light emitting layer diffuse into the fluorescent light emitting layer. A space layer for preventing this may be provided between the light emitting layers.
  • a typical layer structure of the simple light emitting unit is shown below. The layers in parentheses are optional.
  • A (hole injection layer /) hole transport layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
  • B (hole injection layer /) hole transport layer / phosphorescent layer (/ electron transport layer / electron injection layer)
  • C (hole injection layer /) hole transport layer / first fluorescent light emitting layer / second fluorescent light emitting layer (/ electron transport layer / electron injection layer)
  • D (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer / electron injection layer)
  • E (hole injection layer /) hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer / electron injection layer)
  • F (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
  • G (hole injection layer /) hole injection
  • the plurality of phosphorescent light emitting layers, and the phosphorescent light emitting layer and the fluorescent light emitting layer may be light emitting layers having different colors.
  • the light emitting unit (f) includes a hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / electron transporting layer. There may be.
  • An electron blocking layer may be provided between each light emitting layer and the hole transport layer or space layer.
  • a hole blocking layer may be provided between each light emitting layer and the electron transport layer.
  • the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
  • the first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units.
  • the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit. It is a layer to supply and can be formed with a well-known material.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit (organic layer) 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 10 has at least one light emitting layer 5.
  • An anode side organic layer 6 (hole injection layer, hole transport layer, etc.) between the light emitting layer 5 and the anode 3, and a cathode side organic layer 7 (electron injection layer, electron transport) between the light emitting layer 5 and the cathode 4. Layer, etc.) may be formed.
  • an electron blocking layer (not shown) may be provided on the light emitting layer 5 on the anode 3 side, and a hole blocking layer (not shown) may be provided on the light emitting layer 5 on the cathode 4 side.
  • a host combined with a fluorescent dopant is called a fluorescent host
  • a host combined with a phosphorescent dopant is called a phosphorescent host
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material for forming a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the substrate is used as a support for the light emitting element.
  • the material of the substrate for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • the flexible substrate include a plastic substrate made of polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, and an inorganic vapor deposition film.
  • Anode A metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (for example, 4.0 eV or more) is preferably used for the anode formed on the substrate.
  • a high work function for example, 4.0 eV or more
  • examples thereof include indium tin oxide (ITO); indium oxide-tin oxide containing silicon or silicon oxide; indium oxide-zinc oxide; indium oxide containing tungsten oxide and zinc oxide; graphene and the like .
  • ITO indium tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide containing tungsten oxide and zinc oxide
  • graphene and the like graphene and the like
  • gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, nitrides of the metal (for example, titanium nitride), and the like can be
  • anode materials are usually formed by sputtering.
  • indium oxide-zinc oxide is formed by sputtering a target in which 1 to 10 wt% of zinc oxide is added to indium oxide.
  • Indium oxide containing tungsten oxide and zinc oxide is formed by sputtering a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide.
  • the anode may be formed by other methods such as a vacuum deposition method, a coating method, an ink jet method, a spin coating method, and the like.
  • the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. Therefore, as the anode material, a general material such as a metal, an alloy, an electrically conductive compound, a mixture thereof, and an element belonging to Group 1 or Group 2 of the periodic table can be used. Materials having a low work function, for example, alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium and strontium, alloys containing these metals (for example, MgAg and AlLi), rare earth metals such as europium and ytterbium, An alloy containing a rare earth metal can also be used as the anode material.
  • alkali metals such as lithium and cesium
  • alkaline earth metals such as magnesium, calcium and strontium
  • alloys containing these metals for example, MgAg and AlLi
  • rare earth metals such as europium and ytterbium
  • an anode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these metals
  • a vacuum evaporation method or a sputtering method can be used.
  • coating method, the inkjet method, etc. can be used.
  • Hole injection layer is a layer containing a material having a high hole injection property (hole injection material).
  • Hole injection materials include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide Products, manganese oxides, and the like can be used.
  • Low molecular organic compounds such as 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
  • Polymer compounds such as 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), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Poly-TPD) or the like can also be used as the hole injection layer material.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino) phenyl] phenyl-N′-phenylamino ⁇
  • a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
  • HAT hexaazatriphenylene
  • R 21 to R 26 may be the same as or different from each other, and each independently represents a cyano group, —CONH 2 , a carboxyl group, or —COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or Represents a cycloalkyl group having a number of 3 to 20. However, R 21 and R 22 , R 23 and R 24 , or R 25 and R 26 are bonded to each other and represented by —CO—O—CO—.
  • R 27 examples 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.
  • a compound represented by the following formula (2-1) or (2-2) is also preferable as the hole injection layer material.
  • Ar 21 represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted ring forming atom number of 5 to 30 atoms.
  • the aromatic hydrocarbon ring is preferably a benzene ring.
  • the aromatic heterocyclic ring is preferably a ring having 6 ring atoms, for example, a pyridine ring, a pyrazine ring, and a pyridazine ring.
  • X 23 to X 28 are each independently C (R) or a nitrogen atom.
  • R is independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, 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, substituted Or a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted An alkoxy group having an alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having an aryl group having 6 to 30 ring carbon atoms
  • a 21 to a 23 are ring structures represented by the following formula (2b).
  • X 20 in the formula (2b) is represented by any of the following formulas (2b-1) to (2b-12). (In the formulas (2b-1) to (2b-12), R 20 has the same meaning as R.)
  • R 23 to R 28 are each independently synonymous with R.
  • the hole transport layer is a layer containing a material having a high hole transport property (hole transport material).
  • the compound (1) of the present invention is preferably used for the hole transport layer alone or in combination with the following compounds.
  • the hole transporting material other than the compound (1) for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used.
  • aromatic amine compound examples include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and 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-N
  • carbazole derivative examples include 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9 And -phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA).
  • CBP 4,4′-di (9-carbazolyl) biphenyl
  • CzPA 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene
  • PCzPA 9 And -phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole
  • anthracene derivative examples include 2-t-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth) and the like can be given.
  • t-BuDNA 2-t-butyl-9,10-di (2-naphthyl) anthracene
  • DNA 9,10-di (2-naphthyl) anthracene
  • DPAnth 9,10-diphenylanthracene
  • Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used for the hole transport layer.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • a compound other than the above may be used as the hole transporting layer material.
  • the hole transport layer may be a single layer or a laminate composed of two or more layers.
  • the hole transport layer may be a layer including a first hole transport layer (anode side) and a second hole transport layer (cathode side).
  • the compound (1) may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both, provided that the first hole transport layer includes The compound (1) contained is different from the compound (1) contained in the second hole transport layer.
  • Each layer of the two or more hole transport layers may contain a hole transport material other than the above-described compound (1).
  • the compound (1) is preferably contained in only one of the first hole transport layer and the second hole transport layer, and in another embodiment, the compound (1) is contained in the first positive transport layer. It is preferable that it is contained only in the hole transport layer. In still another embodiment, it is preferable that the compound (1) is contained only in the second hole transport layer. In still another embodiment, the compound (1) is contained in the first hole transport layer. It is preferable to be included in both the first hole transport layer and the second hole transport layer.
  • the light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials such as a fluorescent light-emitting material and a phosphorescent material can be used as the dopant material.
  • the fluorescent light-emitting material is a compound that emits light from a singlet excited state
  • the phosphorescent material is a compound that emits light from a triplet excited state.
  • pyrene derivatives As a blue fluorescent material, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives and the like can be used.
  • 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
  • An aromatic amine derivative or the like can be used as a green fluorescent material.
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials.
  • N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used as the blue phosphorescent material.
  • An iridium complex or the like is used as a green phosphorescent material.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used.
  • iridium complex bis [2- (2′-benzo [4,5- ⁇ ] 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)), (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdp
  • 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)
  • tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Rare earth metal complexes such as TTA) 3 (Phen))
  • TTA acac 3
  • Eu rare earth metal complexes such as TTA 3 (Phen)
  • the dopant material described above may be dispersed in another material (host material). It is preferable to use a material having a lowest lowest orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.
  • LUMO level lowest lowest orbital level
  • HOMO level lower highest occupied orbital level
  • host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives, (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives are used.
  • metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives
  • condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives
  • Aromatic amine compounds such as triary
  • metal complex examples include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq3), bis (10-hydroxybenzo).
  • the heterocyclic compound include 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
  • condensed aromatic compound examples include 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 ( Abbreviations: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9′-bianthryl (abbreviation: BANT), 9,9 ′-(stilbene- 3,3′-diyl) diphenanthrene (abbreviation: DPNS), 9,9 ′-(stilbene-4,4
  • aromatic amine compound examples include 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), 4,4′-bis [N-
  • the electron transport layer is a layer containing a material having a high electron transport property (electron transport material).
  • a material having a high electron transport property for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, (2) aromatic heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, (3) A polymer compound can be used.
  • Examples of the metal complex include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato ) Beryllium (abbreviation: BeBq 2 ), 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).
  • Alq tris (8-quinolinolato) aluminum
  • Almq3 tris (4-methyl-8-quinolinolato) aluminum
  • heteroaromatic compound for example, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(Pt-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), bathocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzo
  • polymer compound for example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9, 9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
  • the above material is a compound having an electron mobility of 10 ⁇ 6 cm 2 / Vs or higher. Note that materials other than those described above may be used for the electron-transport layer as long as the material has a higher electron-transport property than the hole-transport property. Further, the electron transport layer is not limited to a single layer, and may be a stack of two or more layers each including the above material.
  • the electron injection layer is a layer containing a material having a high electron injection property (electron injection material).
  • a material having a high electron injection property electron injection material
  • an alkali metal such as lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, or lithium oxide, an alkaline earth metal, or a compound thereof can be used.
  • an electron transporting compound containing an alkali metal, an alkaline earth metal, or a compound thereof, for example, an Alq containing magnesium may be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material containing an organic compound and an electron donor (donor) may be used for the electron injection layer. Since the organic compound receives electrons from the electron donor, such a composite material is excellent in electron injecting property and electron transporting property.
  • the organic compound is preferably a compound that is excellent in transporting received electrons.
  • the above-described electron transport layer materials metal complexes, aromatic heterocyclic compounds, and the like
  • the electron donor may be any compound that can donate electrons to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • the cathode is preferably formed of a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (for example, 3.8 eV or less).
  • cathode materials include alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium, and strontium, alloys containing these metals (for example, MgAg, AlLi), europium (Eu), and ytterbium.
  • alkali metals such as lithium and cesium
  • alkaline earth metals such as magnesium, calcium, and strontium
  • alloys containing these metals for example, MgAg, AlLi
  • Eu europium
  • ytterbium examples thereof include rare earth metals such as (Yb) and alloys containing rare earth metals.
  • a vacuum evaporation method or a sputtering method can be used.
  • coating method, the inkjet method, etc. can be used.
  • a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. Can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • Insulating layer Since an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit. In order to prevent this, a thin film insulating layer may be inserted between the pair of electrodes.
  • the material used for 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, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture of these materials may be used, or a laminate of a plurality of layers containing these materials may be used.
  • the space layer is, for example, in the case of laminating a fluorescent light emitting layer and a phosphorescent light emitting layer, for the purpose of adjusting the carrier balance so as not to diffuse excitons generated in the phosphorescent light emitting layer into the fluorescent light emitting layer.
  • This is a layer provided between the fluorescent light emitting layer and the phosphorescent light emitting layer.
  • the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, the space layer is preferably formed of a material having both electron transport properties and hole transport properties. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
  • a blocking layer such as an electron blocking layer, a hole blocking layer, or a triplet blocking layer may be provided in a portion 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 transport layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer.
  • the triplet blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into an adjacent layer and confining the excitons in the light emitting layer.
  • Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like.
  • it can be formed by a known deposition method such as a vacuum deposition method or a molecular beam deposition method (MBE method), or a known coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method. it can.
  • the film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates, so 5 nm to 10 ⁇ m is preferable. It is more preferably 0.2 ⁇ m.
  • the organic EL element can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, and a personal computer, and electronic equipment such as a light emitting device for lighting and a vehicle lamp.
  • display devices such as an organic EL panel module
  • display devices such as a television, a mobile phone, and a personal computer
  • electronic equipment such as a light emitting device for lighting and a vehicle lamp.
  • intermediate a2 (1-bromo-2- (2-phenylpropan-2-yl) benzene) Under an argon atmosphere, intermediate a1 (660 g) was dissolved in benzene (2.5 L), and hydrochloric acid gas was bubbled for 4 hours. Thereafter, Ar gas was bubbled for 1 hour and cooled to 0 ° C. Subsequently, aluminum chloride (81.8 g) was added to the reaction vessel, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 16 hours. Water was added to the resulting mixture and extracted with toluene. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then concentrated under reduced pressure to obtain intermediate a2 (749 g, yield 55%).
  • Synthesis Example 9 Synthesis of Compound 9
  • Compound 9 was synthesized in the same manner using Intermediate 9 instead of Intermediate 1.
  • m / e 841 with respect to the molecular weight 841 of Compound 9.
  • Example 1 Manufacture of organic EL element A glass substrate with 25 mm ⁇ 75 mm ⁇ 1.1 mm ITO transparent electrode (anode) (manufactured by Geomatic) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. It was. The film thickness of ITO was 130 nm.
  • the glass substrate with a transparent electrode after washing was mounted on a substrate holder of a vacuum deposition apparatus. First, compound HA was vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, thereby forming a 5 nm-thick hole injection layer.
  • Compound 1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm.
  • a compound HT2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
  • a compound BH (host material) and a compound BD (dopant material) were formed on the second hole transport layer by co-evaporation to form a light emitting layer having a thickness of 25 nm.
  • the mass ratio of Compound BH to Compound BD contained in the light emitting layer was 96: 4.
  • the compound ET1 was deposited to form a first electron transport layer having a thickness of 10 nm, and then the compound ET2 was deposited to form a second electron transport layer having a thickness of 15 nm.
  • LiF was deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metal Al was vapor-deposited on this electron injection layer to form a metal cathode having a thickness of 80 nm, and an organic EL device was produced.
  • Examples 2 to 3 and Comparative Examples 1 to 3 An organic EL device was produced in the same manner as in Example 1 except that Compound 7, Compound 15, and Comparative Compounds 1 to 3 were used instead of Compound 1, and the external quantum efficiency of the organic EL device was measured. The results are shown in Table 1.
  • Compound 1 is a compound obtained by replacing the 9,9-diphenylfluorene skeleton and 9,9′-spirobifluorene skeleton of Comparative Compounds 1 and 2 (Comparative Examples 1 and 2) with a spiroanthracene fluorene skeleton.
  • Compound 7 is a compound obtained by replacing the 9,9-diphenylfluorene skeleton of Comparative Compound 3 (Comparative Example 3) with a spiroanthracene fluorene skeleton.
  • the 9,9-diphenylfluorene skeleton and 9,9′-spirobifluorene of the comparative compound provides an organic EL device in which the light emission efficiency (external quantum efficiency) is further improved as compared with an organic EL device containing a comparative compound.
  • the effect of improving the luminous efficiency of the compound of the present invention is considered to be due to the fact that the hole mobility is higher than that of the comparative compound.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

La présente invention concerne un composé représenté par la formule (1) qui fournit un élément électroluminescent organique présentant une efficacité lumineuse exceptionnelle. (Dans la formule (1), R1-R8, R11-R18, R21, R22, L1, L2, L3, Ar1 et Ar2 sont tels que définis dans la description).
PCT/JP2018/009247 2017-03-10 2018-03-09 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2018164265A1 (fr)

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KR20200040653A (ko) * 2018-10-10 2020-04-20 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20200100241A (ko) * 2019-02-15 2020-08-26 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
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WO2021103058A1 (fr) * 2019-11-25 2021-06-03 武汉华星光电半导体显示技术有限公司 Matériau de transport de trous, son procédé de préparation et dispositif électroluminescent
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US12338234B2 (en) 2018-11-30 2025-06-24 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
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CN109970575A (zh) * 2019-04-22 2019-07-05 吉林奥来德光电材料股份有限公司 有机电致发光化合物及其制法和应用
US12048242B2 (en) 2019-05-31 2024-07-23 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
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