[go: up one dir, main page]

WO2013039184A1 - Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant - Google Patents

Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2013039184A1
WO2013039184A1 PCT/JP2012/073548 JP2012073548W WO2013039184A1 WO 2013039184 A1 WO2013039184 A1 WO 2013039184A1 JP 2012073548 W JP2012073548 W JP 2012073548W WO 2013039184 A1 WO2013039184 A1 WO 2013039184A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
substituted
unsubstituted
ring
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/073548
Other languages
English (en)
Japanese (ja)
Inventor
由美子 水木
裕勝 伊藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Publication of WO2013039184A1 publication Critical patent/WO2013039184A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present invention relates to an aromatic amine derivative and an organic electroluminescence device using the same.
  • organic electroluminescence elements using organic substances are expected to be used as solid-state, inexpensive, large-area full-color display elements, and many developments have been made. ing.
  • an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer.
  • an electric field is applied between both electrodes of the organic EL element, electrons are injected from the cathode side and holes are injected from the anode side.
  • the injected electrons and holes recombine with the light emitting layer, excitons are formed, and energy is released as light when the excited state returns to the ground state.
  • the organic EL element emits light based on such a principle.
  • Patent Document 1 discloses a light-emitting material having dibenzofuran, and although blue light emission with a short wavelength is obtained, the light emission efficiency is low and further improvement is required. It was.
  • Patent Documents 4 and 5 disclose diaminopyrene derivatives.
  • Patent Document 2 discloses a combination of an anthracene host and an arylamine.
  • Patent Documents 3 to 5 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant. Further, Patent Documents 6 to 8 disclose anthracene host materials.
  • Patent Document 9 discloses that an aromatic amine derivative having an arylene group at the center and having a dibenzofuran ring bonded to a nitrogen atom is used as a hole transport material.
  • Patent Document 10 discloses a dibenzofuran ring, a dibenzofuran ring, and a dibenzofuran ring. Although it is disclosed that an aromatic amine derivative in which a thiophene ring, a benzofuran ring, a benzothiophene ring or the like is bonded to a nitrogen atom via an arylene group is used as a hole transport material, there is no example of using it as a light emitting material.
  • Patent Documents 11 to 13 disclose aromatic amine derivatives in which amino groups are bonded to the 1-position and 6-position of pyrene.
  • aromatic amine derivatives described in Patent Document 11 and Patent Document 12 a dibenzofuran ring or a dibenzothiophene ring is bonded to the nitrogen atom of the amino group.
  • These aromatic amine derivatives are used as blue light emitting materials, but further improvement in color purity and luminous efficiency is required for practical use.
  • An object of the present invention is to provide an organic EL element capable of obtaining blue light emission and a useful aromatic amine derivative that can be used for an organic thin film layer of the organic EL element.
  • the following aromatic amine derivative and organic EL device are provided.
  • R 1 to R 10 are each independently Hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms,
  • L 1 , L 2 and L 3 are each independently Single bond, It is a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 1 is a monovalent substituent having the following general formula (3) as a partial structure.
  • X represents an oxygen atom or a sulfur atom.
  • a and B represent a 6-membered ring. The 6-membered ring represented by A and B. In addition, another ring may be condensed.
  • Ar 2 is A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent substituent having the general formula (3) as a partial structure.
  • X represents an oxygen atom or a sulfur atom.
  • R 11 to R 18 are each independently Hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkoxy group
  • X 2 represents an oxygen atom or a sulfur atom.
  • X 3 is an oxygen atom, a sulfur atom, NR 31 or CR 32 R 33 .
  • R 21 to R 30 are each independently a hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubsti
  • R 21 to R 30 when Ar 1 is any monovalent residue from the general formula (5) to the general formula (10), among R 21 to R 30 , One is a single bond that binds to L 1 , and when Ar 2 is any monovalent residue from General Formula (5) to General Formula (10), R 21 One of up to R 30 is a single bond bonded to L 2 .
  • R 31 , R 32 and R 33 are each independently A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 27 and R 28 , R 28 and R 29 are used. And a combination of at least one of R 29 and R 30 may form a saturated or unsaturated ring. However, in General Formula (7) and General Formula (8), R 25 and R 26 do not form a ring. )
  • R 1 in the general formula (1) is represented by the general formula (2).
  • R 2 in the general formula (1) is represented by the general formula (2).
  • a characteristic aromatic amine derivative is represented by the general formula (2).
  • R 4 in the general formula (1) is represented by the general formula (2).
  • a characteristic aromatic amine derivative is represented by the general formula (2).
  • An organic compound layer is provided between the cathode and the anode,
  • the organic compound layer is an organic electroluminescence device including the aromatic amine derivative according to any one of [1] to [6].
  • the organic compound layer includes a plurality of organic thin film layers including a light emitting layer, At least one layer among the plurality of organic thin film layers includes the aromatic amine derivative according to any one of [1] to [6].
  • An organic electroluminescence element In the organic electroluminescence device according to [7], the organic compound layer includes a plurality of organic thin film layers including a light emitting layer, At least one layer among the plurality of organic thin film layers includes the aromatic amine derivative according to any one of [1] to [6].
  • At least one of the plurality of organic thin film layers is composed of the aromatic amine derivative according to any one of [1] to [6], and an anthracene derivative represented by the following general formula (20):
  • An organic electroluminescence device comprising:
  • Ar 11 and Ar 12 are each independently A substituted or unsubstituted monocyclic group having 5 to 30 ring atoms; A substituted or unsubstituted condensed ring group having 10 to 30 ring atoms or a combination of the monocyclic group and the condensed ring group.
  • R 101 to R 108 are each independently Hydrogen atom, A halogen atom, A cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, A group composed of a combination of the monocyclic group and the condensed ring group, 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, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted aryloxy having 6 to 30 ring carbon atoms, or a substituted or unsubstituted silyl group.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms.
  • One of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring atom having 10 to 30 atoms.
  • Ar 12 in the general formula (20) is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, and a dibenzofuranyl group, and Ar 11 is an unsubstituted phenyl group, the monocyclic group, or the condensed ring group.
  • Ar 12 in the general formula (20) is a substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, and Ar 11 is an unsubstituted phenyl group. .
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted phenyl group.
  • Ar 11 in the general formula (20) is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent. Electroluminescence element.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • an organic EL device capable of emitting blue light can be provided.
  • aromatic amine derivatives The aromatic amine derivative of the present invention is represented by the general formula (1). Next, R 1 to R 10 in the general formula (1) will be described.
  • Examples of the aryl group having 6 to 30 ring carbon atoms in the general formula (1) include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, Benzanthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, pyrenyl group, 1-chrysenyl group, 2-chrysenyl group, 3-chrysenyl group, 4- Chrysenyl group, 5-chrenyl group, 6-chrenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group Group, 4-fluorenyl group, 9-fluoren
  • the aryl group in the general formula (1) preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12 carbon atoms.
  • a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable.
  • the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the general formula (1) is present at the 9-position carbon atom. It is preferably substituted.
  • heterocyclic group having 5 to 30 ring atoms in the general formula (1) examples include pyrrolyl group, pyrazinyl group, pyridyl group, pyrimidinyl group, triazinyl group, pyridazinyl group, indolyl group, isoindolyl group, imidazolyl group, Pyrazolyl group, triazolyl group, benzoimidazolyl group, indazolyl group, imidazopyridinyl group, benzotriazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothiophenyl group, dibenzo Thiophenyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl
  • the number of ring-forming atoms of the heterocyclic group in the general formula (1) is preferably 5-20, and more preferably 5-14.
  • the heterocyclic groups 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, a 4-dibenzothiophenyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, and a 9-carbazolyl group are preferable.
  • the substituted or unsubstituted aryl having 6 to 30 ring carbon atoms in the general formula (1) is attached to the 9th-position nitrogen atom.
  • the group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
  • the alkyl group having 1 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic.
  • Examples of the linear or branched alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n- Hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n- Hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpenty
  • cyclic alkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and 2- And norbornyl group.
  • the linear or branched alkyl group in the general formula (1) preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • the cycloalkyl group preferably has 3 to 10 ring carbon atoms, and more preferably 5 to 8 carbon atoms.
  • a cyclopentyl group and a cyclohexyl group are preferable.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.
  • the alkenyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic, such as vinyl, propenyl, butenyl, oleyl, eicosapentaenyl, docosahexa Examples include enyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2-propenyl and the like.
  • a vinyl group is preferable.
  • the alkynyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like. Of the alkynyl groups described above, an ethynyl group is preferred.
  • Examples of the alkylsilyl group having 3 to 30 carbon atoms in the general formula (1) include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group, Triethylsilyl, tri-n-butylsilyl, tri-n-octylsilyl, triisobutylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-propylsilyl, dimethyl-n-butylsilyl, dimethyl -T-butylsilyl group, diethylisopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triisopropylsilyl group and the like.
  • the three alkyl groups may be the same or different from each other.
  • Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the general formula (1) include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
  • Examples of the dialkylarylsilyl group include a dialkylarylsilyl group having two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. .
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • the two alkyl groups may be the same or different.
  • alkyldiarylsilyl group examples include an alkyldiarylsilyl group having one alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. .
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • the two aryl groups may be the same or different.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the three aryl groups may be the same or different from each other.
  • the alkoxy group having 1 to 30 carbon atoms in the general formula (1) is represented by —OY 1 .
  • Y 1 include the alkyl group having 1 to 30 carbon atoms.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more halogen groups.
  • the aralkyl group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —Y 2 —Z 1 .
  • Y 2 include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • this Z 1 include the examples of the aryl group having 6 to 30 ring carbon atoms.
  • the aralkyl group has an aralkyl group having 7 to 30 carbon atoms (the aryl moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 20 carbon atoms). More preferably, it is 1 to 10, and more preferably 1 to 6).
  • Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m
  • the aryloxy group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —OZ 2 .
  • Z 2 include the aryl group having 6 to 30 ring carbon atoms, or a monocyclic group and a condensed ring group described later.
  • Examples of the aryloxy group include a phenoxy group.
  • halogen atom in the general formula (1) examples include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • examples of the substituent include an aryl group, a heterocyclic group, an alkyl group (a linear or branched alkyl group, a cycloalkyl group, a halogenated alkyl group) as described above,
  • alkenyl groups, alkynyl groups, alkylsilyl groups, arylsilyl groups, alkoxy groups, halogenated alkoxy groups, aralkyl groups, aryloxy groups, halogen atoms, cyano groups, hydroxyl groups, nitro groups, carboxy groups, and the like can be given.
  • an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and further, specific examples that are preferable in the description of each substituent Preferred substituents are preferred.
  • “Unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is substituted. In the compound described below or a partial structure thereof, when it is referred to as “substituted or unsubstituted”, the substituent is the same as described above.
  • any one of R 1 to R 10 is represented by the general formula (2).
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted divalent residue of an aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted This is a divalent residue of an unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • the divalent residue of the aryl group having 6 to 30 ring carbon atoms is a divalent group derived from the aryl group having 6 to 30 ring carbon atoms in R 1 to R 10 in the general formula (1).
  • the divalent residue of the heterocyclic group having 5 to 30 ring atoms is a divalent derivative derived from the heterocyclic group having 5 to 30 ring atoms in R 1 to R 10 of the general formula (1).
  • the group of is mentioned.
  • Ar 1 is a monovalent substituent having the general formula (3) as a partial structure.
  • X is an oxygen atom or a sulfur atom.
  • a and B represent a 6-membered ring. Another ring may be further condensed to the 6-membered ring represented by A and B.
  • Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or the general formula ( It is a monovalent substituent having 3) as a partial structure.
  • the aryl group and heterocyclic group of Ar 2 are the same as those described in R 1 to R 10 in the general formula (1).
  • the monovalent substituent having the general formula (3) as a partial structure is preferably a monovalent residue of the general formula (4).
  • X is an oxygen atom or a sulfur atom.
  • R 11 to R 18 are the same as those described for R 1 to R 10 in the general formula (1).
  • Ar 1 is a monovalent residue of the general formula (4)
  • one of R 11 to R 18 is bonded to L 1 .
  • Ar 2 is a monovalent residue of the general formula (4), one of R 11 to R 18 is a single bond that binds to L 2 . is there.
  • the structure of the general formula (4) is, for example, as shown in the following general formula (4A) to general formula (4D).
  • the general formula (4A) indicates that the portion of R 11 in the general formula (4) is a single bond, and does not indicate that it is a methyl group. This also applies to the other general formulas (4B) to (4D).
  • general formula (4A) when R 11 is a single bond and general formula (4C) when R 13 is a single bond are preferable.
  • R 11 and R 12, R 12 and R 13, R 13 and R 14, R 15 and R 16, R 16 and R 17 and R 17 and R 18, at least one One or a combination may form a saturated or unsaturated ring.
  • Examples of the case where such a ring may be formed in the general formula (4) include the following general formulas (4E), (4F), and (4G).
  • R 11 to R 20 are each independently the same as those described for R 1 to R 10 in the general formula (1). .
  • the monovalent substituent having the general formula (3) as a partial structure is any of the monovalent residues from the general formula (5) to the general formula (10). It is preferable that In the general formula (5) to general formula (10), X 2 is an oxygen atom or a sulfur atom. In the general formula (5) to general formula (10), X 3 is an oxygen atom, a sulfur atom, NR 31 or CR 32 R 33 .
  • NR 31 is a combination of R 31 and a nitrogen atom (N).
  • CR 32 R 33 is obtained by bonding R 32 and R 33 to a carbon atom (C).
  • R 21 to R 30 are independently the same as those described in R 1 to R 10 in the general formula (1).
  • Ar 1 is any monovalent residue from the general formula (5) to the general formula (10)
  • R 21 to R 30 One is a single bond that binds to L 1
  • Ar 2 is any monovalent residue from General Formula (5) to General Formula (10)
  • R 21 One of up to R 30 is a single bond bonded to L 1 .
  • the structure from the general formula (5) to the general formula (10) is, for example, from the following general formula (5A) to the general formula (5J).
  • R 31 , R 32 and R 33 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted.
  • the aryl group, heterocyclic group and alkyl group of R 31 , R 32 and R 33 are the same as those described in R 1 to R 10 in the general formula (1).
  • R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 27 and R 28 , R 28 and R 29 are used. And a combination of at least one of R 29 and R 30 may form a saturated or unsaturated ring. However, in the general formula (7) and the general formula (8), R 25 and R 26 do not form a ring.
  • aromatic amine derivative of the present invention include the following compounds. However, the present invention is not limited to aromatic amine derivatives having these structures.
  • R 1 in the general formula (1) is preferably represented by the general formula (2).
  • the aromatic amine derivative has the following general formula (1A) It becomes a structure represented by.
  • aromatic amine derivative of the present invention include those in which R 2 to R 10 , L 1 to L 3 , and Ar 1 to Ar 2 in the general formula (1A) are as shown in Tables 1 to 36 An aromatic amine derivative is mentioned.
  • “ ⁇ ” in L 1 to L 3 represents a single bond.
  • a chemical formula (CH 3 , Ph, CN, benzene ring, etc.) is described at the end of the line extending from the ring structure toward the outside. Those not present represent a single bond and do not represent a methyl group.
  • Ar 1 represents a single bond at the 4-position of the dibenzofuran ring, that is, a 4-dibenzofuranyl group.
  • Ar 2 represents a phenyl group.
  • R 2 in the general formula (1) is preferably represented by the general formula (2).
  • the aromatic amine derivative has the following general formula ( 1B).
  • aromatic amine derivative of the present invention examples include R 1, R 3 to R 10 , L 1 to L 3 , and Ar 1 to Ar 2 in the general formula (1B) as shown in Tables 37 to 70 below.
  • Aromatic amine derivatives where indicated.
  • “ ⁇ ” in L 1 to L 3 represents a single bond.
  • the chemical formulas (CH 3 , Ph, CN, benzene ring, etc.) are described at the ends of the lines extending from the ring structure toward the outside. Those not present represent a single bond and do not represent a methyl group.
  • Ar 1 represents a single bond at the 4-position of the dibenzofuran ring, that is, a 4-dibenzofuranyl group.
  • Ar 2 represents a phenyl group.
  • R 4 in the general formula (1) is preferably represented by the general formula (2).
  • the aromatic amine derivative has the following general formula ( 1C).
  • aromatic amine derivative of the present invention examples include R 1 to R 3, R 5 to R 10 , L 1 to L 3 , and Ar 1 to Ar 2 in the general formula (1C).
  • An aromatic amine derivative in the case of 104 is mentioned.
  • “ ⁇ ” in L 1 to L 3 represents a single bond.
  • L 1 to L 3 and Ar 1 to Ar 2 in the table a chemical formula (CH 3 , Ph, CN, benzene ring, etc.) is described at the end of the line extending from the ring structure toward the outside. Those not present represent a single bond and do not represent a methyl group.
  • Ar 1 represents a single bond at the 4-position of the dibenzofuran ring, that is, a 4-dibenzofuranyl group.
  • Ar 2 represents a phenyl group.
  • the aromatic amine derivative of the present invention can be used as a material for an organic EL device.
  • the material for an organic EL device may contain the aromatic amine derivative of the present invention alone or may contain other compounds.
  • the material for organic EL elements containing the aromatic amine derivative of the present invention can be used as a dopant material, for example.
  • a material for an organic EL device including an anthracene derivative represented by the general formula (20) can be given.
  • the organic EL element material which contains the pyrene derivative represented by following General formula (30) with the aromatic amine derivative of this invention instead of this anthracene derivative is mentioned.
  • the organic EL element material containing the aromatic amine derivative of this invention, the anthracene derivative represented by the said General formula (20), and the pyrene derivative represented by the following general formula (30) is mentioned.
  • the organic EL device of the present invention includes an organic compound layer between a cathode and an anode.
  • the aromatic amine derivative of the present invention is contained in this organic compound layer.
  • an organic compound layer is formed using the material for organic EL elements containing the aromatic amine derivative of this invention.
  • the organic compound layer has at least one organic thin film layer composed of an organic compound. At least one of the organic thin film layers contains the aromatic amine derivative of the present invention alone or as a component of a mixture.
  • the organic thin film layer may contain the inorganic compound. At least one of the organic thin film layers is a light emitting layer.
  • the organic compound layer may be composed of, for example, a single light emitting layer, such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, an electron barrier layer, etc. You may have the layer employ
  • the aromatic amine derivative of the present invention is contained alone or as a component of the mixture in at least one of the layers.
  • the light emitting layer contains the aromatic amine derivative of the present invention.
  • the light emitting layer can be composed of only an aromatic amine derivative, or can be composed of an aromatic amine derivative as a host material or a dopant material.
  • the configuration (d) is preferably used, but is not limited thereto.
  • the “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • the “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “an electron injection layer and an electron transport layer”. "At least one of them”.
  • the positive hole injection layer is provided in the anode side.
  • the electron injection layer is provided in the cathode side.
  • the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers.
  • the layer that injects holes from the electrode is a hole injection layer
  • the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
  • a layer that injects electrons from an electrode is referred to as an electron injection layer
  • a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
  • the organic EL element can prevent the brightness
  • a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination.
  • light emission luminance and light emission efficiency may be improved.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
  • the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic compound layer 10 disposed between the anode 3 and the cathode 4.
  • the organic compound layer 10 includes a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and an electron injection layer 9 in order from the anode 3 side.
  • the light emitting layer of the organic EL element has a function of providing a field for recombination of electrons and holes and connecting this to light emission.
  • the aromatic amine derivative of the present invention is contained in at least one layer of the organic thin film layer, and is further represented by the anthracene derivative represented by the general formula (20) and the following general formula (30). It is preferable that at least one of pyrene derivatives is contained.
  • the light emitting layer preferably contains the aromatic amine derivative of the present invention as a dopant material and the anthracene derivative represented by the formula (20) as a host material.
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms or a condensed or unsubstituted ring atom having 10 to 30 ring atoms. It is a group composed of a ring group or a combination of the monocyclic group and the condensed ring group.
  • the monocyclic group is a group composed of only a ring structure having no condensed structure.
  • the number of ring-forming atoms of the monocyclic group is 5 to 30, preferably 5 to 20.
  • the monocyclic group include aromatic groups such as phenyl group, biphenyl group, terphenyl group, and quarterphenyl group, and heterocyclic groups such as pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group, and thienyl group. Is mentioned. Among these, a phenyl group, a biphenyl group, and a terphenyl group are preferable.
  • the condensed ring group is a group in which two or more ring structures are condensed.
  • the number of ring-forming atoms of the fused ring group is from 10 to 30, preferably from 8 to 20.
  • Examples of the condensed ring group include naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzochrysenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorene group.
  • Nyl group benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group and other condensed aromatic ring groups, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, Examples thereof include condensed heterocyclic groups such as a dibenzothiophenyl group, a carbazolyl group, a quinolyl group, and a phenanthrolinyl group.
  • naphthyl group phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzoanthryl group, dibenzothiophenyl group, dibenzofuranyl group, and carbazolyl group are preferable.
  • a group composed of a combination of the monocyclic group and the condensed ring group for example, a phenyl group, a naphthyl group, and a phenyl group are combined in order from the anthracene ring side. And the like (see the following compound EM50 etc.).
  • alkyl group, silyl group, alkoxy group, aryloxy group, aralkyl group, and halogen atom from R 101 to R 108 in the general formula (20) are from R 1 to R 10 in the general formula (1).
  • cycloalkyl group is the same as described above. Further, the case of “substituted or unsubstituted” in these substituents is the same as described above.
  • the preferable specific example in General formula (20) is given below.
  • Ar 11 and Ar 12 in the general formula (20) and preferable substituents of “substituted or unsubstituted” from R 101 to R 108 are monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups. , An alkoxy group, a cyano group, and a halogen atom (particularly fluorine). Particularly preferred are a monocyclic group and a condensed ring group, and preferred specific substituents are the same as those in the general formula (20) and the general formula (1).
  • the anthracene derivative represented by the general formula (20) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected according to the configuration of the organic EL element to be applied and the required characteristics. .
  • Anthracene derivatives (A) In the anthracene derivative (A), Ar 11 and Ar 12 in the general formula (20) are substituted or unsubstituted condensed ring groups having 10 to 30 ring atoms.
  • the anthracene derivative (A) is divided into a case where Ar 11 and Ar 12 are the same substituted or unsubstituted condensed ring group and a case where Ar 11 and Ar 12 are different substituted or unsubstituted condensed ring groups. be able to.
  • Ar 11 and Ar 12 are different, the case where the substitution positions are different is also included.
  • an anthracene derivative in which Ar 11 and Ar 12 in the general formula (20) are different substituted or unsubstituted condensed ring groups is particularly preferable.
  • preferred specific examples of the condensed ring group in Ar 11 and Ar 12 in the general formula (20) are as described above. Of these, a naphthyl group, a phenanthryl group, a benzoanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group are preferable.
  • Anthracene derivatives (B)
  • one of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted group.
  • Ar 12 is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group, and Ar 11 is unsubstituted.
  • anthracene derivative (B) includes a case where Ar 12 is a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms and Ar 11 is an unsubstituted phenyl group.
  • the condensed ring group is particularly preferably a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a benzoanthryl group.
  • Anthracene derivatives (C) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.
  • a preferred form of the anthracene derivative (C) includes a case where Ar 11 and Ar 12 are each independently a substituted or unsubstituted phenyl group.
  • Ar 11 is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • Ar 11 and Ar 12 are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • the monocyclic group as a substituent is more preferably a phenyl group or a biphenyl group
  • the condensed ring group as a substituent is a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a benzoan group.
  • a tolyl group is more preferred.
  • anthracene derivative represented by the general formula (20) include the following. However, the present invention is not limited to the anthracene derivatives having these structures.
  • R 101 and R 105 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted group.
  • a condensed ring group having 10 to 30 ring atoms a group composed of a combination of a monocyclic group and a condensed ring group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon
  • Ar 51 and Ar 54 each independently represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. It is a fused ring divalent residue of ⁇ 30.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 51 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 52 and Ar 55 each independently represent a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 is a single bond, a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a condensed having 10 to 30 substituted or unsubstituted ring atoms. It is a ring divalent residue.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 is a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a condensed condensed or unsubstituted ring atom having 10 to 30 ring atoms. It is a ring divalent residue.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • the present invention is not limited to the anthracene derivatives having these structures.
  • the line extending from the 9th position of the fluorene ring represents a methyl group, that is, the fluorene ring is 9 , 9-dimethylfluorene ring.
  • a line extending in a cross shape outward from the ring structure is a tertiary butyl group. Represents.
  • a line extending from the silicon atom (Si) represents a methyl group, that is, the substituent having the silicon atom represents a trimethylsilyl group.
  • At least one of the organic thin film layers comprises an aromatic amine derivative represented by the general formula (1) and a pyrene derivative represented by the following general formula (30).
  • the form to contain is mentioned.
  • the light emitting layer preferably contains an aromatic amine derivative as a dopant material and a pyrene derivative as a host material.
  • Ar 111 and Ar 222 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • L 1 and L 2 each independently represent a substituted or unsubstituted divalent aryl group or heterocyclic group having 6 to 30 ring carbon atoms.
  • m is an integer of 0 to 1
  • n is an integer of 1 to 4
  • s is an integer of 0 to 1
  • t is an integer of 0 to 3.
  • L 1 or Ar 111 is bonded to any one of 1 to 5 positions of pyrene
  • L 2 or Ar 222 is bonded to any of 6 to 10 positions of pyrene.
  • Ar 111 and Ar 222 in the general formula (30) and “substituent or unsubstituted” in the substituents of L 1 and L 2 are the same as described above.
  • L 1 and L 2 in the general formula (30) are preferably A substituted or unsubstituted phenylene group, Substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted naphthylene group, It is selected from a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, and a divalent aryl group composed of a combination of these groups.
  • M in the general formula (30) is preferably an integer of 0 to 1.
  • n is preferably an integer of 1 to 2.
  • s is preferably an integer of 0 to 1.
  • T in the general formula (30) is preferably an integer of 0 to 2.
  • the aryl groups of Ar 111 and Ar 222 in the general formula (30) are the same as those described for R 1 to R 10 in the general formula (1). Preferred is a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, and more preferred is a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms.
  • aryl group examples include a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a biphenyl group, an anthryl group, and a pyrenyl group.
  • the aromatic amine derivative of the present invention in addition to the light emitting layer, a hole injection layer, a hole transport layer, It can also be used for an electron injection layer and an electron transport layer.
  • Examples of materials other than the general formula (20) and the general formula (30) that can be used in the light emitting layer together with the aromatic amine derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, Condensed polycyclic aromatic compounds such as decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, triarylamine derivatives, styryl Amine derivatives, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives,
  • the organic thin film layer contains the aromatic amine derivative of the present invention as a dopant material
  • the content of the aromatic amine derivative is preferably 0.1% by mass or more and 20% by mass or less, and preferably 1% by mass or more and 10% by mass. The following is more preferable.
  • the organic EL element of the present invention is produced on a light-transmitting substrate.
  • the translucent substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm or more and 700 nm or less of 50% or more.
  • the substrate preferably further has mechanical and thermal strength.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • a polymer film can also be used as the substrate.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
  • the anode is produced by forming a thin film of these conductive materials by a method such as vapor deposition or sputtering.
  • the light transmittance in the visible region of the anode be greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the conductive material used for the cathode of the organic EL device of the present invention those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum , Lithium fluoride and the like and alloys thereof are used, but not limited thereto.
  • alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto.
  • the ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
  • the aspect which takes out light emission from a cathode side is also employable.
  • the light transmittance in the visible region of the cathode be greater than 10%.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / ⁇ or less.
  • the layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 50 nm to 200 nm.
  • the anode and the cathode may be formed with a layer structure of two or more layers if necessary.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set so that predetermined translucency is ensured by a method such as vapor deposition or sputtering using the conductive material.
  • a hole injection material a compound having the ability to transport holes, the hole injection effect from the anode, the hole injection effect excellent for the light emitting layer or the light emitting material, and the thin film forming ability Is preferred.
  • a more effective hole injection material is a phthalocyanine derivative.
  • phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.
  • carriers can be sensitized by adding an electron acceptor such as a TCNQ derivative to the hole injection material.
  • a preferred hole transport material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative.
  • the aromatic tertiary amine derivative include N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra Biphenyl-1,1′-biphenyl-4,4′-diamine or the like, or an oligomer or polymer having an aromatic tertiary amine skeleton is not limited thereto.
  • the following electron injection materials are used for the electron injection / transport layer.
  • the electron injecting material a compound having an ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable.
  • more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.
  • the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis. (10-Hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, and the like are exemplified, but not limited thereto.
  • nitrogen-containing heterocyclic derivative for example, oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine and the like are preferable, and among them, benzimidazole derivative, phenanthroline derivative, imidazopyridine Derivatives are preferred.
  • a preferred form of the organic EL device of the present invention includes a form in which at least one of an electron donating dopant and an organometallic complex is further contained in these electron injection materials. More preferably, in order to facilitate reception of electrons from the cathode, at least one of an electron donating dopant and an organometallic complex is doped in the vicinity of the interface between the organic thin film layer and the cathode. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • K, Rb, and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
  • the electron donating dopant and the organometallic complex may be used singly or in combination of two or more.
  • Each layer of the organic EL device of the present invention can be formed by any of dry deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet. can do.
  • the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
  • an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like
  • any solvent may be used.
  • an organic EL material-containing solution containing the aromatic amine derivative of the present invention and a solvent can be used as a material for an organic EL element.
  • an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
  • the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or an instrument, a lighting device, a display board, a marker lamp, and the like.
  • the compound of this invention can be used not only in an organic EL element but in fields, such as an electrophotographic photoreceptor, a photoelectric conversion element, a solar cell, an image sensor.
  • a light emitting material in addition to at least one selected from the aromatic amine derivatives represented by the general formula (1), a light emitting material, a doping material, a hole injection material, At least one of the hole transport material and the electron injection material may be contained in the same layer.
  • a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. It is also possible to do.
  • the configuration of the organic EL element is not limited to the configuration example of the organic EL element 1 shown in FIG.
  • an electron barrier layer may be provided on the anode side of the light emitting layer
  • a hole barrier layer may be provided on the cathode side of the light emitting layer.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is preferable that at least one light emitting layer contains the aromatic amine derivative of the present invention.
  • the other light emitting layer may be a fluorescent light emitting layer that includes a fluorescent light emitting material and emits fluorescence, or may be a phosphorescent light emitting layer that includes a phosphorescent light emitting material and emits phosphorescence.
  • these light emitting layers may be provided adjacent to each other, or may be laminated via other layers (for example, charge generation layers). .
  • amine compound 1 (3.1 g (12 mmol)), 1-bromopyrene (2.8 g (10 mmol)), sodium tert-butoxide (1 g), tris (dibenzylideneacetone) dipalladium (0) [Pd 2 (dba) 3 ] (550 mg), tri-tert-butylphosphine (115 mg), and dehydrated toluene (90 mL) were added and reacted at 85 ° C. for 7 hours. After the reaction, the reaction solution was filtered, and the resulting crude product was purified by silica gel chromatography (developing solvent: toluene).
  • Synthesis examples 2 to 13 (synthesis of compounds 2 to 13) Synthesis Examples 2 to 13 were performed in the same manner as Synthesis Example 1 except that the amine compound 1 in Synthesis Example 1 was changed to the following amine compounds 2 to 13. As a result, the following compounds 2 to 13 were obtained.
  • Table 105 shows the correspondence between each synthesis example, the amine compound used, and the obtained aromatic amine derivative.
  • Synthesis Example 14 (Synthesis of Compound 14) Synthesis Example 14 was carried out in the same manner as Synthesis Example 1 except that 1-bromopyrene in Synthesis Example 1 was changed to 2-bromopyrene. As a result, the following compound 14 was obtained.
  • Synthesis examples 15-19 Synthesis Examples 15 to 19 were carried out in the same manner as Synthesis Example 14 except that the amine compound 1 of Synthesis Example 14 was changed to the amine compound 3, amine compound 4, amine compound 6, amine compound 9, and amine compound 12. As a result, the following compounds 15 to 19 were obtained.
  • Table 106 shows the correspondence between each synthesis example, the amine compound used, and the obtained aromatic amine derivative.
  • Synthesis Example 20 (Synthesis of Compound 20) Synthesis Example 20 was performed in the same manner as Synthesis Example 1, except that 1-bromopyrene in Synthesis Example 1 was changed to 4-bromopyrene. As a result, the following compound 20 was obtained.
  • Synthesis examples 21-25 Synthesis Examples 21 to 25 were carried out in the same manner as Synthesis Example 20 except that the amine compound 1 of Synthesis Example 20 was changed to amine compound 3, amine compound 4, amine compound 6, amine compound 9, and amine compound 12. As a result, the following compounds 21 to 25 were obtained.
  • Table 106 shows the correspondence between each synthesis example, the amine compound used, and the obtained aromatic amine derivative.
  • Example 1 A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm. This transparent electrode serves as an anode. Subsequently, the glass substrate was cleaned by irradiating with ultraviolet rays and ozone, and then placed in a vacuum deposition apparatus. First, N ′, N ′′ -bis [4- (diphenylamino) phenyl] -N ′, N ′′ -diphenylbiphenyl-4,4′-diamine having a thickness of 60 nm is formed on the transparent electrode of the glass substrate. To form a hole injection layer.
  • N, N, N ′, N′-tetrakis (4-biphenyl) -4,4′-benzidine was deposited on the hole injection layer to a thickness of 20 nm to form a hole transport layer.
  • the anthracene derivative EM2 as a host material and the compound 1 as a dopant material were co-evaporated on the hole transport layer at a mass ratio of 40: 2, thereby forming a light-emitting layer having a thickness of 40 nm.
  • tris (8-hydroxyquinolinato) aluminum was evaporated to a thickness of 20 nm on this light emitting layer to form an electron injection layer.
  • Example 1 lithium fluoride was vapor-deposited on the electron injection layer to a thickness of 1 nm.
  • aluminum was deposited on the lithium fluoride film to a thickness of 150 nm.
  • the aluminum film and lithium fluoride film serve as a cathode.
  • the organic EL element of Example 1 was produced.
  • the organic EL element of Example 1 was driven at a current density of 10 mA / cm 2 , blue light emission was observed.
  • Compound 1 was confirmed to be useful as an organic EL device material.
  • Examples 2 to 25 The organic EL devices of Examples 2 to 25 were prepared in the same manner as in Example 1 except that Compound 1 as the dopant material of the organic EL device of Example 1 was changed from Compound 2 to Compound 25, respectively.
  • Example 26 The organic EL device of Example 26 was produced in the same manner as in Example 1 except that the anthracene derivative EM2 serving as the host material of Example 1 was changed to the anthracene derivative EM367.
  • Examples 27 to 50 The organic EL devices of Examples 27 to 50 were fabricated in the same manner as in Example 26 except that Compound 1 as the dopant material of Example 26 was changed from Compound 2 to Compound 25, respectively.
  • the organic EL elements of Examples 2 to 50 were driven at a current density of 10 mA / cm 2 in the same manner as the organic EL element of Example 1. As a result, blue light emission was observed in any of the organic EL elements of Examples 2 to 50. Thus, it was confirmed that the compounds 1 to 25 are useful as organic electroluminescence device materials.
  • Example 51 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum deposition apparatus, and first, the following compound HT-1 is vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode line is formed, A compound HT-1 film having a thickness of 5 nm was formed. This HT-1 film functions as a hole injection layer.
  • the following compound HT-2 was vapor-deposited to form an HT-2 film having a thickness of 80 nm on the HT-1 film.
  • This HT-2 film functions as a first hole transport layer.
  • the following compound HT-3 was vapor-deposited to form an HT-film having a thickness of 15 nm on the HT-2 film.
  • This HT-3 film functions as a second hole transport layer.
  • the following compound BH-1 (host material) and the compound 4 (dopant material) were co-evaporated at a mass ratio of 25: 5 to form a light emitting layer having a thickness of 30 nm.
  • the following compound TB-1 was deposited on this light emitting layer to form a 20 nm thick barrier layer.
  • the following compound ET-1 which is an electron transport material, was deposited on the barrier layer to form an electron injection layer having a thickness of 5 nm.
  • LiF was vapor-deposited on this electron injection layer to form a 1-nm thick LiF film.
  • Metal Al was vapor-deposited on this LiF film to form a metal cathode having a thickness of 80 nm.
  • the organic EL element of Example 51 was produced.
  • Comparative example 1 The organic EL device of Comparative Example 1 was produced in the same manner as in Example 1 except that Compound 4 was changed to Comparative Compound in Example 51.
  • the organic EL device of Example 51 using Compound 4 as a dopant material has a smaller value of color purity CIEy than the organic EL device of Comparative Example 1 using a comparative compound. It can be seen that the emission peak wavelength is short, and the light is emitted with higher blue purity. From these results, it can be said that the compound of the present invention including Compound 4 is particularly useful for preparing a blue fluorescent element.
  • aromatic amine derivative of this invention although the example which light-emitted blue in the said Example is shown, it is not limited to this.
  • An aromatic amine derivative having a structure in which an aryl group or the like is directly bonded to a pyrene ring can emit green light.
  • the compounds D417 to D424 are mentioned.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
  • a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.

Landscapes

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

Abstract

L'invention concerne un dérivé d'amine aromatique représenté par la formule (1). Dans la formule générale (1), R1 à R10 représentent chacun indépendamment un atome d'hydrogène ou un groupe substituant. Dans la formule générale (1), n'importe lequel parmi R1 à R10 est représenté par la formule générale (2), et L1 à L3 représentent chacun indépendamment une liaison simple, un reste bivalent d'un groupe aryle ou similaire. Dans la formule générale (2), Ar1 est un groupe substituant monovalent ayant la formule générale (3) comme structure partielle ; X est un atome d'oxygène ou un atome de soufre ; et A et B représentent des cycles à six chaînons. Dans la formule générale (2), Ar2 est un groupe aryle, un groupe substituant monovalent ayant la formule générale (3) comme structure partielle ou similaire.
PCT/JP2012/073548 2011-09-16 2012-09-13 Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant Ceased WO2013039184A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-203851 2011-09-16
JP2011203851A JP2015013804A (ja) 2011-09-16 2011-09-16 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子

Publications (1)

Publication Number Publication Date
WO2013039184A1 true WO2013039184A1 (fr) 2013-03-21

Family

ID=47883401

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/073548 Ceased WO2013039184A1 (fr) 2011-09-16 2012-09-13 Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant

Country Status (3)

Country Link
JP (1) JP2015013804A (fr)
TW (1) TW201313696A (fr)
WO (1) WO2013039184A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014208614A (ja) * 2013-03-25 2014-11-06 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置
WO2015129896A1 (fr) * 2014-02-28 2015-09-03 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et appareil électronique
US20160093810A1 (en) * 2014-09-25 2016-03-31 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
KR20160055671A (ko) * 2014-11-07 2016-05-18 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자
US20160190450A1 (en) * 2014-12-24 2016-06-30 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light emitting device including the same
JP2017008023A (ja) * 2015-06-17 2017-01-12 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． モノアミン誘導体、及び有機電界発光素子
US9640773B2 (en) 2011-09-16 2017-05-02 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence element using same
US9780317B2 (en) 2012-12-05 2017-10-03 Samsung Display Co., Ltd. Amine derivative, organic luminescent material and organic electroluminescent device using the amine derivative or the organic luminescent material
US9997715B2 (en) 2014-11-18 2018-06-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
CN109305950A (zh) * 2017-07-26 2019-02-05 三星显示有限公司 光吸收剂和包括该光吸收剂的有机电致发光装置
US10205102B2 (en) 2015-06-17 2019-02-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
CN109694328A (zh) * 2017-10-20 2019-04-30 江苏三月光电科技有限公司 一种三芳香胺类化合物、其制备方法及其在有机电致发光器件中的应用
EP3502107A1 (fr) * 2017-12-20 2019-06-26 Samsung Display Co., Ltd. Composé basé sur le 1-aminodibenzofurane et dispositif électroluminescent organique le comprenant
US10693079B2 (en) * 2015-06-17 2020-06-23 Samsung Display Co., Ltd. Mono amine derivatives and organic electroluminescent device including the same
WO2020182070A1 (fr) * 2019-03-08 2020-09-17 江苏三月光电科技有限公司 Composé utilisant de la triarylamine contenant du pyrène ou de l'azapyrène comme noyau et son utilisation
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
JP2024501179A (ja) * 2020-12-22 2024-01-11 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、およびこれを含む有機発光素子
US11937500B2 (en) 2015-12-22 2024-03-19 Samsung Display Co., Ltd. Organic light-emitting device

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10199589B2 (en) * 2015-01-09 2019-02-05 Toray Industries, Inc. Photoelectric conversion element and image sensor using same
CN107162916B (zh) * 2017-05-05 2020-04-17 吉林奥来德光电材料股份有限公司 有机电致发光材料及其制备方法和有机电致发光器件
CN111662189A (zh) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 一种以含有芘或者氮杂芘的三芳胺为核心的化合物及其应用
CN111662190A (zh) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 一种含芘或氮杂芘的有机化合物及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009542735A (ja) * 2006-07-11 2009-12-03 メルク パテント ゲーエムベーハー 有機エレクトロルミネセンス素子のための新規な材料
WO2010083873A1 (fr) * 2009-01-20 2010-07-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010083872A2 (fr) * 2009-01-20 2010-07-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011059099A1 (fr) * 2009-11-16 2011-05-19 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique le comprenant
JP2011173973A (ja) * 2010-02-24 2011-09-08 Toyo Ink Sc Holdings Co Ltd 有機エレクトロルミネッセンス素子用材料およびその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009542735A (ja) * 2006-07-11 2009-12-03 メルク パテント ゲーエムベーハー 有機エレクトロルミネセンス素子のための新規な材料
WO2010083873A1 (fr) * 2009-01-20 2010-07-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2010083872A2 (fr) * 2009-01-20 2010-07-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2011059099A1 (fr) * 2009-11-16 2011-05-19 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique le comprenant
JP2011173973A (ja) * 2010-02-24 2011-09-08 Toyo Ink Sc Holdings Co Ltd 有機エレクトロルミネッセンス素子用材料およびその用途

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HUANG,T. ET AL.: "Organic electroluminescent derivatives containing dibenzothiophene and diarylamine segments", JOURNAL OF MATERIALS CHEMISTRY, vol. 15, no. 31, 2005, pages 3233 - 3240, XP003018906, DOI: doi:10.1039/b507210g *
KU,Y. ET AL.: "Organic electroluminescent bis(diarylamino) dibenzofuran derivatives", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 53, no. 6, 2006, pages 1317 - 1324 *

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9640773B2 (en) 2011-09-16 2017-05-02 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence element using same
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
US10629830B2 (en) 2012-12-05 2020-04-21 Samsung Display Co., Ltd. Organic electroluminescent device
US9780317B2 (en) 2012-12-05 2017-10-03 Samsung Display Co., Ltd. Amine derivative, organic luminescent material and organic electroluminescent device using the amine derivative or the organic luminescent material
JP2014208614A (ja) * 2013-03-25 2014-11-06 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置
WO2015129896A1 (fr) * 2014-02-28 2015-09-03 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et appareil électronique
US12274162B2 (en) 2014-02-28 2025-04-08 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic apparatus
US11616200B2 (en) 2014-02-28 2023-03-28 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic apparatus
JP2017114903A (ja) * 2014-02-28 2017-06-29 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
JPWO2015129896A1 (ja) * 2014-02-28 2017-03-30 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
US10333075B2 (en) 2014-09-25 2019-06-25 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
KR20160037059A (ko) * 2014-09-25 2016-04-05 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 사용한 유기 전계 발광 소자
US20160093810A1 (en) * 2014-09-25 2016-03-31 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US9972787B2 (en) * 2014-09-25 2018-05-15 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US10333076B2 (en) 2014-09-25 2019-06-25 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
JP2016066723A (ja) * 2014-09-25 2016-04-28 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子用材料及びこれを用いた有機電界発光素子
KR102488020B1 (ko) * 2014-09-25 2023-01-13 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 사용한 유기 전계 발광 소자
KR20160055671A (ko) * 2014-11-07 2016-05-18 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자
US10937969B2 (en) 2014-11-07 2021-03-02 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
JP2016092302A (ja) * 2014-11-07 2016-05-23 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子用材料及びこれを用いた有機電界発光素子
KR102471097B1 (ko) * 2014-11-07 2022-11-28 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자
US10347844B2 (en) 2014-11-07 2019-07-09 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US9997715B2 (en) 2014-11-18 2018-06-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
US11793063B2 (en) * 2014-12-24 2023-10-17 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light emitting device including the same
US20160190450A1 (en) * 2014-12-24 2016-06-30 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light emitting device including the same
US10693079B2 (en) * 2015-06-17 2020-06-23 Samsung Display Co., Ltd. Mono amine derivatives and organic electroluminescent device including the same
JP2017008023A (ja) * 2015-06-17 2017-01-12 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． モノアミン誘導体、及び有機電界発光素子
US10205102B2 (en) 2015-06-17 2019-02-12 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
US11937500B2 (en) 2015-12-22 2024-03-19 Samsung Display Co., Ltd. Organic light-emitting device
US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
KR20190012305A (ko) * 2017-07-26 2019-02-11 삼성디스플레이 주식회사 광 흡수제 및 이를 포함하는 유기 전계 발광 소자
KR102469542B1 (ko) * 2017-07-26 2022-11-23 삼성디스플레이 주식회사 광 흡수제 및 이를 포함하는 유기 전계 발광 소자
CN109305950B (zh) * 2017-07-26 2023-08-22 三星显示有限公司 光吸收剂和包括该光吸收剂的有机电致发光装置
CN109305950A (zh) * 2017-07-26 2019-02-05 三星显示有限公司 光吸收剂和包括该光吸收剂的有机电致发光装置
US11683955B2 (en) * 2017-07-26 2023-06-20 Samsung Display Co., Ltd. Light absorber and organic electroluminescence device including the same
CN109694328A (zh) * 2017-10-20 2019-04-30 江苏三月光电科技有限公司 一种三芳香胺类化合物、其制备方法及其在有机电致发光器件中的应用
EP3502107B1 (fr) * 2017-12-20 2022-01-26 Samsung Display Co., Ltd. Composé basé sur le 1-aminodibenzofurane et dispositif électroluminescent organique le comprenant
CN109942557A (zh) * 2017-12-20 2019-06-28 三星显示有限公司 胺类化合物和包括该胺类化合物的有机发光装置
EP3502107A1 (fr) * 2017-12-20 2019-06-26 Samsung Display Co., Ltd. Composé basé sur le 1-aminodibenzofurane et dispositif électroluminescent organique le comprenant
WO2020182070A1 (fr) * 2019-03-08 2020-09-17 江苏三月光电科技有限公司 Composé utilisant de la triarylamine contenant du pyrène ou de l'azapyrène comme noyau et son utilisation
JP2024501179A (ja) * 2020-12-22 2024-01-11 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、およびこれを含む有機発光素子
EP4269414A4 (fr) * 2020-12-22 2025-03-05 LT Materials Co., Ltd. Composé hétérocyclique et dispositif électroluminescent organique le comprenant

Also Published As

Publication number Publication date
JP2015013804A (ja) 2015-01-22
TW201313696A (zh) 2013-04-01

Similar Documents

Publication Publication Date Title
JP6082179B2 (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP6434073B2 (ja) 有機エレクトロルミネッセンス素子
JP6088979B2 (ja) 芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子
JP6424002B2 (ja) 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料
JP6129075B2 (ja) ビスカルバゾール誘導体およびこれを用いた有機エレクトロルミネッセンス素子
KR101441177B1 (ko) 비스카르바졸 유도체를 사용한 유기 일렉트로루미네선스 소자
WO2013039184A1 (fr) Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant
JP6101248B2 (ja) 新規化合物、有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子
WO2013039221A1 (fr) Dérivé d'amine aromatique et élément électroluminescent organique l'utilisant
JP6060095B2 (ja) カルバゾール化合物、有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子
JP2013063931A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
WO2013042775A1 (fr) Dérivé d'amine aromatique et élément électroluminescent organique l'employant
JP2015135836A (ja) 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料
WO2013058343A1 (fr) Élément à électroluminescence organique et matériau pour élément à électroluminescence organique
JPWO2012090967A1 (ja) 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2013042769A1 (fr) Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci
JP2013107853A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP2013063929A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP2015051925A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP5868652B2 (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP2015013805A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子
JP6047116B2 (ja) 新規なアントラセン化合物及びこれを用いた有機エレクトロルミネッセンス素子
JP2015013807A (ja) 芳香族アミン誘導体およびそれを用いた有機エレクトロルミネッセンス素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12831758

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12831758

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP