WO2010010924A1 - Dérivé anthracène, et élément organique électroluminescent le comprenant - Google Patents

Dérivé anthracène, et élément organique électroluminescent le comprenant Download PDF

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WO2010010924A1
WO2010010924A1 PCT/JP2009/063192 JP2009063192W WO2010010924A1 WO 2010010924 A1 WO2010010924 A1 WO 2010010924A1 JP 2009063192 W JP2009063192 W JP 2009063192W WO 2010010924 A1 WO2010010924 A1 WO 2010010924A1
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河村　昌宏
光則 伊藤
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出光興産株式会社
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    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • 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

Definitions

  • the present invention relates to an anthracene derivative and an organic electroluminescence element using the anthracene derivative.
  • an organic EL element (organic electroluminescence element) using light emission of an organic compound.
  • the organic EL element has a plurality of organic thin films stacked between an anode and a cathode.
  • a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively.
  • Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.
  • Patent Documents 1 to 10 disclose materials that can be used for the light emitting layer. However, any of the materials has problems such as low luminous efficiency and short lifetime of the organic EL element obtained.
  • An object of the present invention is to provide a novel luminescent material and an organic EL element using the luminescent material.
  • anthracene derivatives represented by the following formula (1) (excluding those represented by the following formula (1 ′)).
  • R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. However, Ar 1 does not include an orthophenylene structure. ) 2.
  • R 11 to R 15 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms
  • Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of R 11 ⁇ R 15 other than R 11 ⁇ R 15 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms
  • Any one of R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms
  • Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of R 21 ⁇ R 25 other than R 21 ⁇ R 25 is a substituted or unsubstituted heterocyclic group having 5 to
  • R 12 and R 22 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and R 11 , R 13 , 2.
  • R 14 , R 15 , R 21 , R 23 , R 24 and R 25 are hydrogen atoms. 4).
  • R 13 and R 23 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, and R 11 , R 12 , 2.
  • Ar 1 is an unsubstituted phenyl group, a fluorenyl group having a substituent at the 9-position, an unsubstituted condensed aromatic group having 10 to 20 nuclear carbon atoms, or an unsubstituted heterocyclic group having 5 to 20 nuclear atoms.
  • An anode and a cathode Having one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode;
  • the organic electroluminescent element in which at least 1 layer of the said organic thin film layer contains the organic electroluminescent element material of 8. 11.
  • the organic electroluminescence device according to 10 wherein the light emitting layer contains the material for an organic electroluminescence device.
  • 12 The organic electroluminescence device according to 11, wherein the material for an organic electroluminescence device is a host material.
  • an organic electroluminescence device containing at least one of a fluorescent dopant and a phosphorescent dopant.
  • R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. However, Ar 1 does not include an orthophenylene structure.
  • the organic electroluminescence device according to 13, wherein the fluorescent dopant is an arylamine compound. 16. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (2).
  • R e is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50
  • t is an integer of 0 to 10.
  • Ar 3 to Ar 6 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms. ) 17. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (3).
  • R f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50
  • u is an integer of 0-8.
  • Ar 7 to Ar 10 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. ) 18. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (4).
  • R g is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50
  • R 30 and R 31 are each a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.
  • Ar 11 to Ar 14 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms.
  • a novel light emitting material and an organic EL element using the light emitting material can be provided.
  • the anthracene derivative of the present invention is a compound represented by the following formula (1).
  • R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R 11 to R 15 and R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. However, Ar 1 does not include an orthophenylene structure. )
  • the “hydrogen atom” includes a deuterium atom.
  • “nuclear carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • the “nuclear atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • a phenyl group substituted with a naphthyl group is a substituted aryl group having 16 carbon atoms
  • a phenyl group substituted with a methyl group is an aryl group having 6 substituted nuclear carbon atoms.
  • the substituent in “substituted or unsubstituted...” includes an alkyl group, aryl group, cycloalkyl group, alkoxy group, heterocyclic group, halogen atom as described later. , A hydroxyl group, a nitro group, a cyano group, etc., preferably an alkyl group, an aryl group, a cycloalkyl group, or a heterocyclic group.
  • Ar 1 of the anthracene derivative of the present invention does not include an orthophenylene structure.
  • the fact that it does not contain an orthophenylene structure means that it does not have a substituent at the ortho position of the phenyl moiety of Ar 1 directly bonded to the anthracene skeleton of the anthracene derivative of the present invention.
  • Ar 1 is a phenyl group
  • the following anthracene derivatives are not included in the present invention. (In the formula, X is a substituent.)
  • anthracene derivative of the present invention may exclude those represented by the following formula (1 ′).
  • Ar 1 is preferably an unsubstituted phenyl group, a fluorenyl group having a substituent at the 9-position, an unsubstituted condensed aromatic group having 10 to 20 nuclear carbon atoms, or an unsubstituted heterocyclic ring having 5 to 20 nuclear atoms. It is a group.
  • R 1 to R 7 of the anthracene derivative of the present invention are preferably hydrogen atoms from the viewpoint that it is easy to obtain light of a low wavelength side such as blue.
  • R 11 to R 15 and R 21 to 25 of the anthracene derivative of the present invention preferably satisfy any of the following (A) to (D).
  • At least one of R 11 to R 15 and at least one of R 21 to R 25 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms.
  • R 12 and R 22 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms
  • R 11 , R 13 , R 14 , R 15 , R 21 , R 23 , R 24 and R 25 are hydrogen atoms.
  • R 13 and R 23 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, R 11 , R 12 , R 14 , R 15 , R 21 , R 22 , R 24 and R 25 are hydrogen atoms.
  • any one of R 11 to R 15 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms; or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, or a substituted or all of R 11 ⁇ R 15 other than R 11 ⁇ R 15 is a heterocyclic group having 5 to 50 ring atoms unsubstituted hydrogen
  • any one of R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of R 21 ⁇ R 25 other than R 21 ⁇ R 25 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is It
  • Examples of the alkyl group having 1 to 20 carbon atoms of R 1 to R 7 , R 11 to R 15 and R 21 to R 25 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and an s-butyl group.
  • Examples of the cycloalkyl group having 3 to 20 carbon atoms of R 1 to R 7 , R 11 to R 15 and R 21 to R 25 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, 1 -Adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
  • it is a cyclopentyl group or a cyclohexyl group.
  • the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R 1 to R 7 , R 11 to R 15 and R 21 to R 25 is a group represented by —OZ, and Z is a group represented by R 1 to R 7 is selected from alkyl groups having 1 to 20 carbon atoms. Z is preferably a methyl group or an ethyl group.
  • Examples of substituted or unsubstituted silyl groups for R 1 to R 7 , R 11 to R 15 and R 21 to R 25 include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group. Group, triphenylsilyl group and the like. A trimethylsilyl group or a triphenylsilyl group is preferable.
  • Examples of the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms for R 11 to R 15 , R 21 to R 25 and Ar 1 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 6-chrysenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [C] phenanthryl group, 5-benzo [
  • a substituted or unsubstituted phenyl group and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms eg, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group
  • substituted or unsubstituted fluorenyl group (2 -Fluorenyl group
  • substituted or unsubstituted pyrenyl groups (1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group).
  • Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms of R 11 to R 15 , R 21 to R 25 and Ar 1 include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group 3-benzofuranyl group, 4-benzofurany
  • 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group Group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group and 9-carbazolyl group are preferable.
  • Examples of the substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms of R 11 to R 15 and R 21 to R 25 include a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 2-anthryl group.
  • 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group) from the viewpoint of appropriate molecular weight and durability to redox And a fluorenyl group (2-fluorenyl group) are preferred.
  • substituents may further have a substituent such as an alkyl group, a cycloalkyl group, an alkoxy group, a cyano group, a silyl group, an aryl group, a heterocyclic group, a halogen atom, etc.
  • An alkyl group, an aryl group, and a heterocyclic group are preferable, and an aryl group and a heterocyclic group are more preferable. Specific examples of these substituents are as described above.
  • anthracene derivative of the present invention and the anthracene derivative as a host used in combination with the dopant in the organic electroluminescence device will be shown.
  • the anthracene derivative of the present invention can be synthesized, for example, by the method described in WO2004 / 018587. Specific synthesis methods are shown in the examples described later.
  • the anthracene derivative of the present invention can be used as a light emitting material for an organic EL device, and is preferably used as a host material.
  • the organic EL device of the present invention is a device in which one or more organic thin film layers are formed between an anode and a cathode.
  • the organic thin film layer is a plurality of layers, one layer is a light emitting layer.
  • a light emitting layer as an organic thin film layer is formed between the anode and the cathode.
  • At least one of the organic thin film layers contains the anthracene derivative of the present invention, and further transports holes injected from the anode or electrons injected from the cathode to the light-emitting material. Further, a hole injection material or an electron injection material may be contained. Since the anthracene derivative of the present invention has its characteristic steric structure, it has high emission characteristics.
  • a material other than the anthracene derivative of the present invention may be used in combination.
  • compounds represented by the following (i) to (ix) can be used as a host material used in combination in the light emitting layer of the organic EL device of the present invention.
  • Ar 001 is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 50 nuclear carbon atoms.
  • Ar 002 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms.
  • X 001 to X 003 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted A substituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted nuclear atom number of 5 to 50 Aryloxy group, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, carboxyl group, halogen atom, cyano , A nitro group, and a hydroxy group, a, b and c are each an integer of
  • R 001 to R 010 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, Substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted A silyl group
  • Ar 005 and Ar 006 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms.
  • L 001 and L 002 are a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group, respectively.
  • m is an integer from 0 to 2
  • n is an integer from 1 to 4
  • s is an integer from 0 to 2
  • t is an integer from 0 to 4.
  • L 001 or Ar 005 binds to any of the 1-5 positions of pyrene
  • L 002 or Ar 006 binds to any of the 6-10 positions of pyrene.
  • n + t is an even number
  • Ar 005 , Ar 006 , L 001 , and L 002 satisfy the following (1) or (2).
  • a 001 and A 002 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.
  • Ar 007 and Ar 008 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms.
  • R 011 to R 020 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, Substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted A silyl group
  • Ar 007 , Ar 008 , R 019 and R 020 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure.
  • a group that is symmetrical with respect to the XY axis shown on the anthracene is not bonded to the 9th and 10th positions of the central anthracene.
  • R 021 to R 030 are each independently a hydrogen atom, alkyl group, cycloalkyl group, optionally substituted aryl group, alkoxyl group, aryloxy group, alkylamino group, alkenyl group, arylamino group, or substituted.
  • a and b each represent an integer of 1 to 5, and when they are 2 or more, R 021s or R 022s may be the same or different from each other Alternatively, R 021 or R 022 may be bonded to each other to form a ring, and R 023 and R 024 , R 025 and R 026 , R 027 and R 028 , R 029 and R 030 are L 003 may be a single bond, —O—, —S—, —N (R) — (where R is an alkyl group or an aryl group which may be substituted). Represents an alkylene group or an arylene group.)
  • R 031 to R 040 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group, or an optionally substituted multicyclic group
  • C, d, e and f each represent an integer of 1 to 5, and when they are 2 or more, R 031 to each other, R 032 to each other, R 036 to each other or R 037 to each other may be the same may be different, also R 031 together, R 032 together, may also be R 033 s or R 037 are bonded to each other to form a ring, R 033 and R 034, R 039 and R 040 are each other bonded to ring the optionally formed .
  • L 004 is a single bond, -O -, - S -, - N (R) - (R is an aryl group which may be alkyl or substituted
  • a 005 to A 008 are each independently a substituted or unsubstituted biphenylyl group or a substituted or unsubstituted naphthyl group.
  • a 011 to A 013 are each independently a substituted or unsubstituted arylene group having 6 to 50 nuclear carbon atoms.
  • a 014 to A 016 are each independently a hydrogen atom, or a substituted or unsubstituted group.
  • a substituted aryl group having 6 to 50 carbon atoms, R 041 to R 043 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 1 carbon atom; Alkoxy group having 6 to 6 carbon atoms, aryloxy group having 5 to 18 carbon atoms, aralkyloxy group having 7 to 18 carbon atoms, arylamino group having 5 to 16 carbon atoms, nitro group, cyano group, ester group having 1 to 6 carbon atoms Or a halogen atom, and at least one of A 011 to A 016 is a group having three or more condensed aromatic rings.
  • a fluorene compound represented by the following formula (ix) is represented by the following formula (ix).
  • R 051 and R 052 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted amino group, R 051 together to bind to.
  • R 053 and R 054 may be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group.
  • R 053 and R 054 representing an aromatic heterocyclic group and bonded to different fluorene groups are the same or different.
  • R 053 and R 054 bonded to the same fluorene group may be the same or different, and Ar 011 and Ar 012 may be a substituted or unsubstituted condensed group having a total of 3 or more benzene rings.
  • N represents an integer of 1 to 10.
  • the light emitting layer of the organic EL device of the present invention preferably contains a phosphorescent dopant and / or a fluorescent dopant. Further, a light emitting layer containing these dopants may be stacked on the light emitting layer containing the anthracene derivative of the present invention.
  • a phosphorescent dopant is a compound that can emit light from triplet excitons. Although it is not particularly limited as long as it emits light from triplet excitons, it is preferably a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os and Re, and is preferably a porphyrin metal complex or ortho Metalated metal complexes are preferred.
  • the phosphorescent compounds may be used alone or in combination of two or more.
  • the porphyrin metal complex is preferably a porphyrin platinum complex.
  • ligands that form orthometalated metal complexes.
  • Preferred ligands include compounds having a phenylpyridine skeleton, bipyridyl skeleton or phenanthroline skeleton, or 2-phenylpyridine derivatives, 7,8. -Benzoquinoline derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives, 2-phenylquinoline derivatives and the like.
  • These ligands may have a substituent as needed.
  • a fluorinated compound or a compound having a trifluoromethyl group introduced is preferable as a blue dopant.
  • you may have ligands other than the said ligands, such as an acetylacetonate and picric acid, as an auxiliary ligand.
  • metal complexes include tris (2-phenylpyridine) iridium, tris (2-phenylpyridine) ruthenium, tris (2-phenylpyridine) palladium, bis (2-phenylpyridine) platinum, tris (2- Phenylpyridine) osmium, tris (2-phenylpyridine) rhenium, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin, etc.
  • An appropriate complex is selected depending on the device performance and the host compound to be used.
  • content in the light emitting layer of a phosphorescent dopant there is no restriction
  • Fluorescent dopants are required from amine compounds, aromatic compounds, chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc. It is preferable to select a compound in accordance with the emission color, and a styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable. Moreover, the condensed polycyclic aromatic compound which is not an amine compound is also preferable. These fluorescent dopants may be used alone or in combination.
  • styrylamine compound and styryldiamine compound those represented by the following formula (A) are preferable.
  • Ar 101 is a p-valent group, and a corresponding p-valent group of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a stilbenyl group, or a distyrylaryl group
  • Ar 102 and Ar 103 are Each of them is an aromatic hydrocarbon group having 6 to 20 carbon atoms
  • Ar 101 , Ar 102 and Ar 103 may be substituted, and any one of Ar 101 to Ar 103 is substituted with a styryl group.
  • At least one of Ar 102 and Ar 103 is substituted with a styryl group, and p is an integer of 1 to 4, and preferably an integer of 1 to 2.
  • examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, and a terphenyl group.
  • arylamine compound and the aryldiamine compound those represented by the following formula (B) are preferable.
  • Ar 111 is a q-valent substituted or unsubstituted aromatic hydrocarbon group having 5 to 40 nuclear carbon atoms
  • Ar 112 and Ar 113 are each substituted or unsubstituted aryl having 5 to 40 nuclear carbon atoms.
  • Q is an integer of 1 to 4, preferably an integer of 1 to 2.
  • examples of the aryl group having 5 to 40 nuclear carbon atoms include phenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, coronyl, biphenyl, terphenyl, pyrrolyl, furyl, thienyl.
  • Preferred substituents substituted on the aryl group include alkyl groups having 1 to 6 carbon atoms (ethyl group, methyl group, i-propyl group, n-propyl group, s-butyl group, t-butyl group, pentyl group).
  • the light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary.
  • the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.
  • the light emitting layer preferably contains a fluorescent dopant.
  • the fluorescent dopant is preferably a styrylamine compound or an arylamine compound.
  • the arylamine compound is more preferably a compound represented by the following formulas (2) to (4).
  • R e is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms,
  • Ar 3 to Ar 6 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.
  • R f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50
  • Ar 7 to Ar 10 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms.
  • R g is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50
  • R 30 and R 31 are each a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.
  • Ar 11 to Ar 14 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms.
  • examples of the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert- Examples thereof include butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group and the like, preferably methyl group, ethyl group, propyl group, tert- It is a butyl group.
  • Examples of the substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms include benzyl 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
  • Examples of the substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms include, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, bicycloheptyl group, Bicyclooctyl group, tricycloheptyl group, adamantyl group and the like can be mentioned, and cyclopentyl group, cyclohexyl group, cycloheptyl group, bicycloheptyl group, bicyclooctyl group and adamantyl group are preferable.
  • the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms is a group represented by —OZ, and Z is selected from the above substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • the substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms is represented by —OY, and Y is selected from the following substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms.
  • Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms include a phenyl group, a methylphenyl group, an ethylphenyl group, a biphenyl group, a cyclopentylphenyl group, a cyclohexylphenyl group, a methylbiphenyl group, an ethylbiphenyl group, Examples include cyclopentylphenyl group, cyclohexylbiphenyl group, terphenyl group, naphthyl group, methylnaphthyl group, anthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group, perylenyl group, fluorenyl group, and the like, preferably phenyl group, naphthyl group , A fluorenyl group.
  • organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
  • the above-described fluorescent dopant and phosphorescent dopant a known light emitting material, doping material, hole injection material, or electron injection material may be used for the multiple layers as necessary. You can also.
  • 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. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission.
  • the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call.
  • an electron injection layer a layer that injects electrons from an electrode is referred to as an electron injection layer, and 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.
  • an electron injection layer a layer that injects electrons from an electrode
  • an electron transport layer a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, adhesion with the organic layer or the metal electrode.
  • Examples of host materials or doping materials that can be used in the light emitting layer together with the anthracene derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, anthracene derivatives, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, penta Condensed polycyclic aromatic compounds such as phenylcyclopentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like; Derivatives thereof, organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4-
  • the hole injection layer and the hole transport layer help to inject holes into the light emitting layer and transport to the light emitting region, and have a high hole mobility and a small ionization energy of usually 5.5 eV or less.
  • a material for such a hole injection layer and a hole transport layer a material that transports holes to the light emitting layer with lower electric field strength is preferable, and the hole mobility is, for example, 10 4 to 10 6 V / cm. When applying the electric field of 10 ⁇ 4 cm 2 / V ⁇ sec or more, it is preferable.
  • the material for the hole injection layer and the hole transport layer is not particularly limited, and is conventionally used as a charge transport material for holes in optical transmission materials, and the hole injection layer and holes for organic EL devices. An arbitrary thing can be selected and used from the well-known things used for the transport layer.
  • Ar 211 to Ar 213 , Ar 221 to Ar 223, and Ar 203 to Ar 208 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted number of 5 to 50 nuclear atoms.
  • a to c and p to r are integers of 0 to 3, respectively.
  • Ar 203 and Ar 204 , Ar 205 and Ar 206 , Ar 207 and Ar 208 may be connected to each other to form a saturated or unsaturated ring.
  • Ar 231 to Ar 234 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
  • L is a linking group, which is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
  • x is an integer of 0 to 5.
  • Ar 232 and Ar 233 may combine with each other to form a saturated or unsaturated ring. Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms and the substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms are the same as those described above. can give.
  • the material for the hole injection layer and the hole transport layer include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives. And amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (particularly thiophene oligomers).
  • the above materials can be used for the hole injection layer and the hole transport layer, but porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds should be used. Is preferred.
  • NPD 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl
  • MTDATA triphenylamine
  • R 201 to R 206 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R 201 and R 202 , R 203 and R 204 , R 205 and R 206 , R 201 and R 206 , R 202 and R 203 , or R 204 and R 205 may form a condensed ring.
  • R 211 to R 216 are substituents, each preferably an electron-withdrawing group such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group, or a halogen.
  • inorganic compounds such as p-type Si and p-type SiC can also be used as materials for the hole injection layer and the hole transport layer.
  • the hole injection layer and the hole transport layer can be formed by thinning the above-described compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
  • the thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
  • the hole injection layer and the hole transport layer may be composed of one or more layers made of the above-mentioned materials, or a plurality of hole injection layers and hole transport layers made of different compounds are laminated. There may be.
  • an electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer
  • the compound which prevents the movement to and is excellent in thin film forming ability is preferable.
  • the electron injecting material 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), such as tris (8-quinolinolato) aluminum, is injected. It can be used as a material.
  • examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.
  • Ar 1 , Ar 2 , Ar 3 , Ar 5 , Ar 6 , and Ar 9 each represent a substituted or unsubstituted aryl group, and may be the same or different from each other.
  • Ar 4 , Ar 7 and Ar 8 represent a substituted or unsubstituted arylene group, and may be the same or different.
  • materials represented by the following general formulas (A) to (F) can also be used as the electron injection material.
  • a 1 to A 3 are each independently a nitrogen atom or a carbon atom.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms
  • Ar 2 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • any one of Ar 1 and Ar 2 is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms, or a substituted or unsubstituted monoheterocondensed ring group having 5 to 60 nucleus atoms.
  • L 1 , L 2 and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or a substituted or unsubstituted An unsubstituted fluorenylene group.
  • R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R 1 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or —L 1 —Ar 1 —Ar 2 The nitrogen-containing heterocyclic derivative represented by this.
  • HAr-L-Ar 1 -Ar 2 (Wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent, L has a single bond, an arylene group having 6 to 60 nuclear carbon atoms which may have a substituent, a heteroarylene group having 5 to 60 nuclear atoms which may have a substituent, or a substituent.
  • a fluorenylene group which may be Ar 1 is an optionally substituted divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms
  • Ar 2 is an aryl group having 6 to 60 nuclear carbon atoms which may have a substituent or a heterocyclic group having 5 to 60 nuclear atoms which may have a substituent.
  • X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group, a substituted group Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring
  • R 1 to R 4 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, Alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy
  • R 1 to R 8 and Z 2 are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, or an alkoxy group.
  • an aryloxy group, X, Y and Z 1 each independently represent a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group;
  • the substituents of Z 1 and Z 2 may be bonded to each other to form a condensed ring.
  • N represents an integer of 1 to 3, and when n is 2 or more, Z 1 may be different.
  • Q 1 and Q 2 each independently represent a ligand represented by the following general formula (G)
  • L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, —OR 1 (R 1 is a hydrogen atom, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group) or —O—Ga—Q 3 (Q 4 ) (Q 3 and Q 4 are the same as Q 1 and Q 2 ).
  • rings A 1 and A 2 are 6-membered aryl ring structures condensed with each other which may have a substituent.
  • This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.
  • the alkyl group, aromatic hydrocarbon group, aryl group, heterocyclic group, condensed aromatic group and the like described in the above-described dopant hole injecting material, hole transporting material, and electron injecting material in the present invention are represented by the above formula (1). The examples given above for R 1 to R 22 can be applied.
  • the organic EL device of the present invention include a device containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer.
  • the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals.
  • preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV).
  • a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. .
  • alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element.
  • a combination of two or more alkali metals is also preferable.
  • a combination containing Cs such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K.
  • Cs such as Cs and Na, Cs and K, Cs and Rb, or Cs.
  • Na and K a combination of Na and K.
  • an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved.
  • an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
  • preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
  • preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe
  • preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl.
  • preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.
  • a cathode what uses a metal, an alloy, an electroconductive compound, and a mixture thereof with a small work function (4 eV or less) as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li 2 O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
  • This cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the transmittance of the light emitted from the cathode is larger than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit.
  • an insulating thin film layer may be inserted between the pair of electrodes.
  • Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum 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.
  • Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like.
  • 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. If necessary, the anode and the cathode may be formed of two or more layers.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering.
  • the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
  • the substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
  • Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
  • each layer of the organic EL device for the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to.
  • 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 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 resin or additive may be used for improving film formability and preventing pinholes in the film.
  • Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.
  • the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
  • 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 light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
  • the material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.
  • Example 1 Compound 1 was synthesized according to the following synthesis scheme.
  • the obtained crystals were washed with methanol, water, and methanol, and then recrystallized with toluene to obtain pale yellow crystals.
  • Example 2 Compound 2 was synthesized according to the following synthesis scheme.
  • Example 3 Compound 3 was synthesized according to the following synthesis scheme.
  • Example 4 Compound 4 was synthesized according to the following synthesis scheme.
  • Example 5 Compound 5 was synthesized according to the following synthesis scheme.
  • 9,10-dibromo-2-phenylanthracene 9,10-dibromo-2- (2-naphthyl) anthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid.
  • Compound 5 was synthesized and identified in the same manner as in Example 1 except that (2-naphthyl) phenylboronic acid was used.
  • Example 6 Compound 6 was synthesized according to the following synthesis scheme.
  • 9,10-Dibromo-2- (2-naphthyl) anthracene instead of 9,10-dibromo-2-phenylanthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid.
  • Compound 6 was synthesized and identified in the same manner as in Example 1 except that (1-naphthyl) phenylboronic acid was used.
  • Example 7 Compound 7 was synthesized according to the following synthesis scheme.
  • 9,10-dibromo-2-phenylanthracene 9,10-dibromo-2- (2-naphthyl) anthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid.
  • the compound was synthesized and identified in the same manner as in Example 1 except that (2-naphthyl) phenylboronic acid was used.
  • Example 8 Compound 8 was synthesized according to the following synthesis scheme.
  • Example 9 Compound 9 was synthesized according to the following synthesis scheme.
  • Example 10 Compound 10 was synthesized according to the following synthesis scheme.
  • Example 11 [Production of organic EL element] 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 cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and first, a compound A-1 having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Subsequent to the formation of the A-1 film, A-2 having a thickness of 20 nm was formed on the A-1 film. Further, a compound 1 (host material) synthesized in Example 1 and a dopant material D-1 were formed in a film thickness ratio of 40: 2 on the A-2 film at a film thickness of 40 nm to form a light emitting layer.
  • ITO transparent electrode anode
  • the compound ET-1 was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode, thereby forming an organic EL device. When voltage was applied to this organic EL element, blue light emission was obtained.
  • Examples 12 to 125 and Comparative Examples 1 to 30 In Example 11, organic EL devices were similarly produced using the host materials and dopant materials shown in Tables 1 to 4 instead of the host material compound 1 and the dopant material D-1.
  • Tables 1 to 4 show the light emission efficiency, the half-life at an initial luminance of 1000 cd / m 2, and the light emission color of the organic EL devices obtained in Examples 11 to 125 and Comparative Examples 1 to 30, respectively. From the results in Tables 1 to 4, it was found that the organic EL device using the anthracene derivative of the present invention has excellent light emission characteristics.
  • Compound 2 which is an anthracene derivative of the present invention, has an energy gap smaller than that of Compound (A) and exhibits an emission wavelength close to that of Compound (A). Therefore, it is presumed that Compound 2 can emit light with smaller energy and can extend the lifetime of the organic EL device.
  • the compound (B) and the compound (C) also have a small energy gap like the compound 2. However, since these compounds have a longer emission wavelength than the compound 2, energy transfer to the blue dopant is difficult, and the blue element It is estimated that the light emission efficiency decreases.
  • the anthracene derivative of the present invention has an appropriate energy gap and emission wavelength even in the green color, as can be seen from the organic EL devices of Examples 26 to 125, the anthracene derivative of the present invention is highly efficient. A long-life green element is obtained.
  • the organic EL element using the organic light emitting medium of the present invention is useful as a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.
  • a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un dérivé anthracène représenté par la formule (1) (à l'exclusion d'un composé représenté par la formule (1')).
PCT/JP2009/063192 2008-07-25 2009-07-23 Dérivé anthracène, et élément organique électroluminescent le comprenant WO2010010924A1 (fr)

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JP2014177442A (ja) * 2013-03-15 2014-09-25 Idemitsu Kosan Co Ltd ジアミノアントラセン誘導体及び有機エレクトロルミネッセンス素子
US9166179B2 (en) 2009-04-24 2015-10-20 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US9331285B2 (en) 2009-12-16 2016-05-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
US9373792B2 (en) 2009-05-29 2016-06-21 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescent element using the same
WO2016117848A1 (fr) * 2015-01-20 2016-07-28 에스에프씨 주식회사 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci
US20180019430A1 (en) * 2016-07-14 2018-01-18 Sfc Co., Ltd. Organic light-emitting diode with high efficiency
US9902687B2 (en) 2014-09-19 2018-02-27 Idemitsu Kosan Co., Ltd. Compound
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
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US10103338B1 (en) 2017-08-14 2018-10-16 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and electronic device
JP2020132571A (ja) * 2019-02-20 2020-08-31 エルジー・ケム・リミテッド ジベンゾフラン−１−イル又はジベンゾチオフェン−１−イル基を有するアントラセン誘導体及びそれを用いた有機電子デバイス

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