WO2014017094A1 - Organic electroluminescence element - Google Patents

Organic electroluminescence element Download PDF

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WO2014017094A1
WO2014017094A1 PCT/JP2013/004523 JP2013004523W WO2014017094A1 WO 2014017094 A1 WO2014017094 A1 WO 2014017094A1 JP 2013004523 W JP2013004523 W JP 2013004523W WO 2014017094 A1 WO2014017094 A1 WO 2014017094A1
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group
substituted
unsubstituted
carbon atoms
ring
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PCT/JP2013/004523
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French (fr)
Japanese (ja)
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圭 吉田
俊裕 岩隈
英明 長島
亮平 橋本
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出光興産株式会社
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Priority to JP2014526773A priority Critical patent/JP6189296B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to an organic electroluminescence element.
  • Organic electroluminescence (EL) elements include a fluorescent type and a phosphorescent type, and an optimum element design has been studied according to each light emission mechanism. With respect to phosphorescent organic EL elements, it is known from their light emission characteristics that high-performance elements cannot be obtained by simple diversion of fluorescent element technology. The reason is generally considered as follows. Since phosphorescent light emission is light emission using triplet excitons, the energy gap of the compound used for the light emitting layer needs to be large. This is because the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).
  • a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must first be used for the light emitting layer.
  • Patent Documents 1 to 3 material enhancement and element design different from those of fluorescent organic EL elements are required for enhancing the performance of phosphorescent organic EL elements. Material research has been conducted intensively and several reports have been made (Patent Documents 1 to 3).
  • Patent Document 1 and Patent Document 2 benzimidazole compounds are exemplified and used as an electron transport layer material.
  • the triplet energy of the host material of the combined light emitting layer is small and the efficiency is low.
  • the host material to be combined has a structure that does not include a dibenzofuran ring or a dibenzothiophene ring, the charge injecting / transporting property is low and the voltage tends to be high.
  • Patent Document 3 exemplifies benzimidazole compounds and is used as an electron transport layer material, but their triplet energy is small, and the energy of the light emitting layer leaks to the electron transport layer side, so the efficiency is low.
  • An object of the present invention is to provide an organic EL element having a low voltage and a long lifetime.
  • the inventors of the present invention have used a benzimidazole compound having a specific structure excellent in electron injecting and transporting properties for a layer adjacent to the light emitting layer, and a combination using a compound having a specific structure for the light emitting layer. It was found that leakage of the term energy to the electron transport layer side can be suppressed, and an organic EL element having low voltage, high efficiency, and long life can be obtained.
  • the following organic EL elements and the like are provided. 1. Having two or more organic thin film layers including a light emitting layer between the anode and the cathode; The light emitting layer contains at least one compound represented by the following formula (1), The organic thin film layer in contact with the light emitting layer on the cathode side of the light emitting layer contains at least one benzimidazole compound represented by the following formula (A), Organic electroluminescence device.
  • G 1 to G 6 are each independently C—R 1 or a nitrogen atom.
  • G 11 to G 18 are each independently C—R 2 or a nitrogen atom.
  • R and R 1 are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 18 ring atoms, substituted or unsubstituted arylthio group having 6 to 18 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 18 ring atom
  • R 1 of G 2 and G 5 are each independently 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
  • Each R 2 independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atom
  • each R 2 may be the same or different.
  • R, R 1 and R 2 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms.
  • X represents an oxygen atom or a sulfur atom.
  • Ra to Rd, Re to Rf, Rh to Ri, Rj to Rk and Rm to Rn are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted group.
  • Rg and Rl are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon number, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
  • Re to Rf, Rh to Ri, Rj to Rk, and Rm to Rn is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or A substituted or unsubstituted dibenzothiophenyl group;
  • Ar 1 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, a substituted or unsubstituted metabiphenylyl group or metabiphenylylene group.
  • Substituted or unsubstituted metaterphenylyl group or metaterphenylylene group substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,6-pyridylene group Group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted or unsubstituted 2-dibenzothiophenyl Group or 2,8-dibenzothiophenylene group, or substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
  • Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group.
  • Metabiphenylyl group or metabiphenylylene group substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
  • the substituent R ′′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number.
  • m and n are each 0 or 1.
  • o and p are each an integer of 0 to 3.
  • G 221 to G 228 are each independently C—R 22 or a nitrogen atom.
  • Ga to Gk are each independently C—R 23 or a nitrogen atom.
  • R 21 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1;
  • R 22 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1
  • R 23 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1
  • the plurality of R 23 may be the same or different from each other.
  • R 21 , R 22 and R 23 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms
  • X 1 is an oxygen atom or a sulfur atom.
  • X 2 is an oxygen atom, a sulfur atom, or ⁇ C (CH 3 ) 2 . ) 3.
  • Y represents a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monocyclic heteroaromatic ring group having 5 to 7 ring atoms, or the following formula (3- It is group represented by 1).
  • G 311 to G 317 , G 321 to G 327 , and G 331 to G 337 are each independently C—R 31 or a nitrogen atom.
  • R 31 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1;
  • L 3 is a single bond, a divalent linking group containing an oxygen atom, a divalent linking group containing a silicon atom, a divalent linking group containing a sulfur atom, an alkylene group having 1 to 5 carbon atoms, or the number of ring-forming carbon atoms.
  • R 31 has a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a ring Cycloalkoxy group having 3 to 20 carbon atoms, aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, aryloxy group having 6 to 18 ring carbon atoms, heteroaromatic ring having 5 to 18 ring atoms Group, silyl group, fluorine atom, fluoroalkyl group, fluoroalkoxy group or cyano group.
  • X 3 is an oxygen atom or a sulfur atom.
  • R 41 , R 42 and R 43 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted group. It is an aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms.
  • R 41 , R 42 and R 43 may be directly bonded to each other to form a ring, may be bonded through an oxygen atom to form a ring, or may be bonded through a sulfur atom to form a ring.
  • G 41 to G 44 each independently represents C—R 44 or a nitrogen atom.
  • R 44 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • G 411 to G 418 are each independently C—R 45 or a nitrogen atom.
  • R 45 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • the plurality of R 45 may be the same or different from each other.
  • R 41 , R 42 , R 43 , R 44 and R 45 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 20 ring carbon atoms.
  • X 4 is an oxygen atom or a sulfur atom.
  • Rf, Rh, Rk and Rm is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl group, substituted or unsubstituted 5.
  • the organic electroluminescence device according to any one of 1 to 4, which is a 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group. 6).
  • Both Rf and Rh in the formula (A), or both Rk and Rm in the formula (A) are substituted or unsubstituted carbazolyl groups, substituted or unsubstituted azacarbazolyl groups, substituted or unsubstituted 2- Any one of 1 to 5 which is a dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group
  • Ar 1 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted 2-dibenzo group. 7.
  • Ar 2 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group.
  • Any one of 1 to 7 which is a substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group
  • An organic electroluminescence device according to any one of the above. 9.
  • the light emitting layer includes a phosphorescent material; 9.
  • the phosphorescent material is an orthometalated complex of one or more metal atoms selected from iridium (Ir), osmium (Os), and platinum (Pt). .
  • Ir iridium
  • Os osmium
  • Pt platinum
  • the organic electroluminescence device according to any one of 1 to 9 wherein an interface region between the cathode and the organic thin film layer contains an electron donating dopant.
  • R represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
  • Ra to Rd and Rj to Rn are each independently 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 ring carbon atoms, substituted or unsubstituted, Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaro
  • Rm and Rk is a substituted or unsubstituted carbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted A substituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group.
  • Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group.
  • Metabiphenylyl group or metabiphenylylene group substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
  • each of Rm and Rk independently represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted group.
  • 13 12.
  • an organic EL element with low voltage, high efficiency and long life can be provided.
  • the organic EL device of the present invention has two or more organic thin film layers including a light emitting layer between an anode and a cathode, and the light emitting layer contains at least one compound represented by the following formula (1).
  • the organic thin film layer in contact with the light emitting layer on the cathode side of the light emitting layer contains at least one benzimidazole compound represented by the following formula (A).
  • A benzimidazole compound represented by the following formula
  • the compound represented by the formula (A) is the following compound having a benzimidazole skeleton.
  • Ra to Rd, Re to Rf, Rh to Ri, Rj to Rk and Rm to Rn are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted group.
  • Rg and Rl are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon number, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
  • Re and Rf, Rh and Ri, Rj and Rk, and Rm and Rn is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, Or a substituted or unsubstituted dibenzothiophenyl group.
  • Ar 1 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, a substituted or unsubstituted metabiphenylyl group or metabiphenylylene group.
  • Substituted or unsubstituted metaterphenylyl group or metaterphenylylene group substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,6-pyridylene group Group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted or unsubstituted 2-dibenzothiophenyl Group or 2,8-dibenzothiophenylene group, or substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
  • Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group.
  • Metabiphenylyl group or metabiphenylylene group substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
  • the substituent R ′′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number.
  • m and n are each 0 or 1.
  • o and p are each an integer of 0 to 3.
  • m, n, o, and p satisfy m + o ⁇ 1 and n + p ⁇ 1.
  • the plurality of Ar 1 may be the same as or different from each other.
  • the plurality of Ar 2 may be the same as or different from each other.
  • Rf, Rh, Rk, and Rm is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl Group, substituted or unsubstituted 4-dibenzofuranyl group, substituted or unsubstituted 2-dibenzothiophenyl group, or substituted or unsubstituted 4-dibenzothiophenyl group, more preferably Rf, Rh, Rk, At least one of Rm is a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl group, or a substituted or unsubstituted 2-dibenzothiophenyl group.
  • both Rf and Rh, or both Rk and Rm are each a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2- A dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group;
  • Ar 1 is preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, substituted or unsubstituted An unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group, more preferably a single bond or a substituted group Alternatively, it is an unsubstituted alkyl group or alkylene group having 1 to 5 carbon atoms, or a substituted or unsubstituted phenyl group or metaphenylene group.
  • Ar 2 is preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted group.
  • An unsubstituted paraphenylene group a substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group; More preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 5 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, or a substituted or unsubstituted paraphenylene group.
  • n and n satisfy m + n ⁇ 1.
  • the compound represented by the formula (A) is preferably a compound represented by the following formula (a).
  • the compound of the present invention is represented by the following formula (a).
  • R represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
  • Ra to Rd, Rj to Rn, and Ar 2 are the same as in the formula (A).
  • At least one of Rm and Rk is a substituted or unsubstituted carbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted An azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group; n is 0 or 1. p is 0 or 1. n + p ⁇ 1. )
  • each of Rm and Rk independently represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted group.
  • a dibenzothiophenyl group, a substituted or unsubstituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group is preferable.
  • Rm and Rk are substituted or unsubstituted carbazolyl group.
  • the triplet energy of the benzimidazole compound represented by the formula (A) is preferably 2.85 eV or more, more preferably 2.90 eV or more.
  • the compound represented by the formula (A) can be produced by a known method, for example, a method described in JP-A-2009-155300, JP-A-2009-158848, or the like.
  • the compound represented by Formula (1) is the following compound.
  • G 1 to G 6 are each independently C—R 1 or a nitrogen atom.
  • G 11 to G 18 are each independently C—R 2 or a nitrogen atom.
  • R and R 1 are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryl
  • R 1 of G 2 and G 5 are each independently 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
  • Each R 2 independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atom
  • each R 2 may be the same or different.
  • R, R 1 and R 2 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms.
  • a heteroaromatic ring group a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
  • X represents an oxygen atom or a sulfur atom.
  • the compound represented by the formula (1) is preferably any of compounds represented by the following formulas (2a) to (2c), (3a) to (3c) and (4).
  • G 211 to G 214 are each independently C—R 21 or a nitrogen atom.
  • G 221 to G 228 are each independently C—R 22 or a nitrogen atom.
  • Ga to Gk are each independently C—R 23 or a nitrogen atom.
  • R 21 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atom
  • R 22 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1
  • R 23 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1
  • the plurality of R 23 may be the same or different from each other.
  • R 21 , R 22 and R 23 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms
  • X 1 is an oxygen atom or a sulfur atom.
  • X 2 is an oxygen atom, a
  • Y is a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monocyclic heteroaromatic ring group having 2 to 5 ring carbon atoms, or the following formula (3- It is group represented by 1).
  • G 311 to G 317 , G 321 to G 327 , and G 331 to G 337 are each independently C—R 31 or a nitrogen atom.
  • R 31 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ⁇ 20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atom
  • L 3 is a single bond, a divalent linking group containing an oxygen atom, a divalent linking group containing a silicon atom, a divalent linking group containing a sulfur atom, an alkylene group having 1 to 5 carbon atoms, or the number of ring-forming carbon atoms.
  • R 31 has a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a ring Cycloalkoxy group having 3 to 20 carbon atoms, aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, aryloxy group having 6 to 18 ring carbon atoms, heteroaromatic ring having 5 to 18 ring atoms
  • X 3 is an oxygen atom or a sulfur atom.
  • * Indicates a bond with a nitrogen atom.
  • G 341 ⁇ G 347 are each independently C-R 31 or a nitrogen atom, R 31 is the same as R 31 in the formula (3a) ⁇ formula (3c).
  • X 31 is a nitrogen atom, oxygen atom or sulfur atom having a substituent.
  • R 41 , R 42 and R 43 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted group. It is an aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms.
  • R 41 , R 42 and R 43 may be directly bonded to each other to form a ring, may be bonded through an oxygen atom to form a ring, or may be bonded through a sulfur atom to form a ring.
  • G 41 to G 44 each independently represents C—R 44 or a nitrogen atom.
  • R 44 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • G 411 to G 418 are each independently C—R 45 or a nitrogen atom.
  • R 45 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • the plurality of R 45 may be the same or different from each other.
  • R 41 , R 42 , R 43 , R 44 and R 45 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 20 ring carbon atoms.
  • X 4 is an oxygen atom or a sulfur atom.
  • the compounds represented by the formulas (1), (2a) to (2c), (3a) to (3c) and (4) preferably have a triplet energy of 2.9 eV or more.
  • the “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring
  • the “ring-forming atom” includes a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). ) Is a carbon atom and a hetero atom.
  • the hydrogen atom includes isotopes having different neutron numbers such as light hydrogen (protium), deuterium (deuterium), and tritium.
  • aryl group aromatic hydrocarbon group
  • aryl group aromatic hydrocarbon group
  • aryl group aromatic hydrocarbon group
  • phenyl group tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, Benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, fluoranthenyl group and the like are preferable.
  • aryl groups include both fused and non-fused aryl groups.
  • heteroaryl group aromatic heterocyclic group, heteroaromatic ring group, heterocyclic group
  • pyrrolyl group pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group, triazinyl group, indolyl group, Isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, Benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphth
  • the azacarbazolyl group is, for example, an azacarbazolyl group containing 2 to 5 nitrogen atoms, and examples thereof include monovalent groups derived from the following azacarbazole.
  • the bond may be present on any nitrogen atom or any carbon atom, and any nitrogen atom or any carbon atom may be substituted.
  • alkyl group examples include linear, branched and cyclic alkyl groups.
  • linear and branched alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.
  • the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
  • Preferred are a cyclopentyl group and a cyclohexyl group.
  • the alkoxy group is represented as —OY, and examples of Y include the above alkyl examples. Specific examples of the alkoxy group include a methoxy group and an ethoxy group.
  • the cycloalkoxy group is represented as —OY 2, and examples of Y 2 include the examples of the cycloalkyl group described above.
  • the cycloalkoxy group is, for example, a cyclopentyloxy group or a cyclohexyloxy group.
  • the aryloxy group is represented by —OZ, and examples of Z include the above aryl groups.
  • Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
  • the heteroaryloxy group is represented by —OZ ′, and examples of Z ′ include the above heteroaryl groups.
  • Specific examples of the heteroaryloxy group include (carbazol-3-yl) oxy group, (carbazol-4-yl) oxy group, (dibenzofuran-2-yl) oxy group, and the like.
  • the arylcarbonyl group is represented by —COZ, and examples of Z include the above aryl groups.
  • the arylthio group is represented by —SZ, and examples of Z include the above aryl groups.
  • the heteroarylthio group is represented by —SZ ′, and examples of Z ′ include the above heteroaryl groups.
  • Specific examples of the heteroaryloxy group include (carbazol-3-yl) thio group, (carbazol-4-yl) thio group, (dibenzofuran-2-yl) thio group, and the like.
  • the arylsulfonyl group is represented by —SO 2 Z, and examples of Z include the above aryl groups.
  • the heteroarylsulfonyl group is represented by —SO 2 Z ′, and examples of Z ′ include the above heteroaryl groups.
  • heteroaryloxy group examples include (carbazol-3-yl) sulfonyl group, (carbazol-4-yl) sulfonyl group, (dibenzofuran-2-yl) sulfonyl group, and the like.
  • the aralkyl group is represented by —Y—Z.
  • Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples.
  • the aryl part of the aralkyl group preferably has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
  • the alkyl moiety preferably has 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms.
  • benzyl group, phenylethyl group, 2-phenylpropan-2-yl group and the like can be mentioned.
  • halogenated alkyl group examples include groups in which one or more halogen atoms (a fluorine atom, a chlorine atom and a bromine atom are included, preferably a fluorine atom) are substituted on the above-described alkyl group.
  • halogen atoms a fluorine atom, a chlorine atom and a bromine atom are included, preferably a fluorine atom
  • Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a 2,2,2-trifluoroethyl group, and a pentafluoroethyl group.
  • they are a trifluoromethyl group and a pentafluoroethyl group.
  • Examples of the fluoroalkyl group include groups in which one or more fluorine atoms are substituted on the above-described alkyl group. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a 2,2,2-trifluoroethyl group, and a pentafluoroethyl group. Preferably, they are a trifluoromethyl group and a pentafluoroethyl group.
  • Examples of the fluoroalkoxy group include groups in which the alkyl portion of the alkoxy group described above is substituted with one or more fluorine atoms.
  • a fluoromethoxy group a difluoromethoxy group, a trifluoromethoxy group, a fluoroethoxy group, a 2,2,2-trifluoroethoxy group, and a pentafluoroethoxy group.
  • they are a trifluoromethoxy group and a pentafluoroethoxy group.
  • the substituted or unsubstituted silyl group includes, for example, a silyl group, an alkylsilyl group, a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
  • the substituted silyl group is represented by —Si (R a ) (R b ) (R c ), and examples of (R a ), (R b ) and (R c ) include the alkyl group, aryl group, hetero group described above. An aryl group etc. are mentioned.
  • the substituted or unsubstituted amino group includes, for example, an arylamino group, an alkylamino group, and an aralkylamino group.
  • the substituted amino group is represented by —N (Q a ) (Q b ), and examples of (Q a ) and (Q b ) include the alkyl group, aryl group, and aralkyl group described above.
  • alkylene group, cycloalkylene group, arylene group, and heteroarylene group examples include divalent residues corresponding to the above-described alkyl group, cycloalkyl group, aryl group, and heteroaryl group.
  • a metabiphenylyl group, a metabiphenylylene group, a metaterphenylyl group, and a metaterphenylylene group are groups represented by the following formulas, respectively.
  • the compound represented by the formula (A) is a material for an organic thin film layer of an organic EL device, and can be suitably used as an electron transport band layer material. Among the electron transport band layers, the compound is particularly suitable as an electron transport layer material. Can be used.
  • the compounds represented by the formulas (1) to (4) are materials for a light emitting layer of an organic EL device, can be suitably used as a host material for a light emitting layer, and are particularly suitably used as a host material for a blue phosphorescent light emitting layer. be able to.
  • the triplet energy of the compounds represented by the formulas (1) to (4) is sufficiently large, so even if a blue phosphorescent dopant material is used, the triplet energy of the phosphorescent dopant material is efficiently used. This is because it can be confined in the light emitting layer.
  • the compounds represented by the formulas (1) to (4) can be used not only in the blue light emitting layer but also in the light emitting layer of longer wavelength light (such as green to red).
  • the organic EL device of the present invention other configurations are not particularly limited as long as the organic thin film layer and the light emitting layer are configured as described above, and the organic thin film layer containing the compound represented by the formula (A) emits light. Adjacent on the cathode side of the layer.
  • the light emitting layer may contain one or more of the compounds represented by formulas (1) to (4), preferably one of the compounds represented by formulas (1) to (4). Including only.
  • FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
  • the organic EL element 1 has a configuration in which an anode 20, a hole transport zone 30, a phosphorescent light emitting layer 40, an electron transport zone 50, and a cathode 60 are laminated on a substrate 10 in this order.
  • the hole transport zone 30 means a hole transport layer and / or a hole injection layer.
  • the electron transport zone 50 means an electron transport layer and / or an electron injection layer. These need not be formed, but preferably one or more layers are formed.
  • the organic thin film layer is each organic layer provided in the hole transport zone 30, each phosphor layer and the organic layer provided in the electron transport zone 50.
  • FIG. 2 is a schematic view showing the layer structure of another embodiment of the organic EL element of the present invention.
  • the organic EL element 2 is an example of a hybrid organic EL element in which a phosphorescent light emitting layer and a fluorescent light emitting layer are laminated. is there.
  • the organic EL element 2 has the same configuration as the organic EL element 1 except that a space layer 42 and a fluorescent light emitting layer 44 are formed between the phosphorescent light emitting layer 40 and the electron transport zone 50.
  • the excitons formed in the phosphorescent light emitting layer 40 are not diffused into the fluorescent light emitting layer 44, so that a space layer 42 is provided between the fluorescent light emitting layer 44 and the phosphorescent light emitting layer 40. May be provided.
  • the compounds represented by the formulas (1) to (4) can function as a space layer because they have a large triplet energy.
  • the organic EL element 2 for example, when the phosphorescent light emitting layer 40 emits yellow light and the fluorescent light emitting layer 44 forms a blue light emitting layer, a white light emitting organic EL element can be obtained.
  • the phosphorescent light emitting layer 40 and the fluorescent light emitting layer 44 are formed one by one.
  • the present invention is not limited to this, and two or more layers may be formed. it can.
  • a full color light emitting device is formed using a white light emitting element and a color filter, a plurality of wavelength regions such as red, green, blue (RGB), red, green, blue, yellow (RGBY) are used from the viewpoint of color rendering. In some cases, it may be preferable to include luminescence.
  • the organic EL element of the present invention can employ various known configurations.
  • light emission of the light emitting layer can be extracted from the anode side, the cathode side, or both sides.
  • the organic thin film layer in contact with the light emitting layer of the organic EL element on the cathode side contains a compound represented by the formula (A), and the light emitting layer has the formulas (1) to (4). It is not particularly limited as long as it contains one or more of the compounds represented by A known material etc. can be used for each layer of an organic EL element.
  • the organic thin film layer which touches the cathode side of any one light emitting layer should just contain the compound represented by Formula (A).
  • the electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region and has a high electron mobility.
  • the compound represented by the formula (A) includes the electron injection / transport layer. It can be suitably used as an electron transporting material used for the transport layer.
  • an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, such as a pyridine ring. , Pyrimidine ring, triazine ring, benzimidazole ring, phenanthroline ring, quinazoline ring and the like.
  • an organic layer having semiconductivity may be formed by doping a donor material (n) and acceptor material (p).
  • a donor material (n) and acceptor material (p) A typical example of N doping is to dope a metal such as Li or Cs into an electron transporting material, and a typical example of P doping is F4TCNQ (2,3,5,6-Tetrafluoro- 7,7,8,8-tetracyanoquinodimethane) and the like (see, for example, Patent 3695714).
  • the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several ⁇ m. However, particularly when the film thickness is large, in order to avoid a voltage increase, 10 4 to 10 6.
  • the electron mobility is preferably at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of V / cm is applied.
  • the phosphorescent layer containing one or more compounds represented by formulas (1) to (4) as a host contains a phosphorescent dopant (phosphorescent material).
  • a phosphorescent dopant include metal complex compounds, preferably a compound having a metal atom selected from Ir, Pt, Os, Au, Cu, Re and Ru and a ligand.
  • the ligand preferably has an ortho metal bond.
  • the phosphorescent dopant is preferably a compound containing a metal atom selected from Ir, Os and Pt in that the phosphorescent quantum yield is high and the external quantum efficiency of the light-emitting element can be further improved, and an iridium complex, It is more preferable that it is a metal complex such as an osmium complex and a platinum complex, among which an iridium complex and a platinum complex are more preferable, and an orthometalated iridium complex is most preferable.
  • the dopant may be a single type or a mixture of two or more types.
  • the addition concentration of the phosphorescent dopant in the phosphorescent light emitting layer is not particularly limited, but is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass.
  • the light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer. Moreover, it is good also as a double dopant.
  • each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
  • the phosphorescent light emitting layer is formed of a material other than the compounds represented by the formulas (1) to (4), a known material can be used as the material of the phosphorescent light emitting layer.
  • a known material can be used as the material of the phosphorescent light emitting layer.
  • Japanese Patent Application No. 2005-517938 may be referred to.
  • the organic EL device of the present invention may have a fluorescent light emitting layer like the device shown in FIG. A known material can be used for the fluorescent light emitting layer.
  • the host material of the light emitting layer other than the compounds represented by the formulas (1) to (4) a compound containing any of a carbazole ring, a dibenzofuran ring and a dibenzothiophene ring is preferable.
  • Preferred examples of the host material for the light emitting layer other than the compounds represented by the formulas (1) to (4) include compounds represented by the following formula (a). (Wherein L 11 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a heteroarylene group having 5 to 30 ring atoms.
  • X 11 represents O, S, Se, or Te.
  • R 14 and R 15 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted carbon group having 1 to 30 carbon atoms.
  • An alkyl group, a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group, or a substituted or unsubstituted heteroarylsilyl group is represented.
  • s represents an integer of 0 to 3.
  • t represents an integer of 0 to 4.
  • Cz represents a group represented by the following formula (a-1) or the following formula (a-2).
  • R 11 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R 12 and R 13 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms.
  • p and q each independently represents an integer of 0 to 4.
  • r represents an integer of 0 to 3.
  • Examples of the arylene group having 6 to 30 ring carbon atoms and the heteroarylene group having 5 to 30 ring atoms of L 11 in the formula (a) include those similar to L in the formula (1).
  • the aryl group having 6 to 30 ring carbon atoms, the heteroaryl group having 5 to 30 ring atoms, and the alkyl group having 1 to 30 ring atoms of R 11 in formula (a) are represented by R 401 in formula (4) and The same thing as Ra is mentioned.
  • the alkylsilyl group, arylsilyl group, and heteroarylsilyl group of R 11 are groups obtained by arbitrarily combining the alkyl group, the aryl group, the heteroaryl group, and the silyl group, respectively.
  • the aryl group having 6 to 30 ring carbon atoms, the heteroaryl group having 5 to 30 ring atoms, and the alkyl group having 1 to 30 carbon atoms of R 12 to R 15 in the formula (a) are represented by the formula (4): The same thing as Ra is mentioned.
  • the light emitting layer may be a single layer or a laminated structure.
  • the recombination region can be concentrated on the light emitting layer interface by accumulating electrons and holes at the light emitting layer interface. Thereby, quantum efficiency can be improved.
  • Blocking layer It is also preferable to use compounds represented by the formulas (1) to (4) in a layer adjacent to the phosphorescent light emitting layer 40.
  • a layer containing the material of the present invention an anode side adjacent layer
  • the layer functions as an electron barrier layer. It functions as an exciton blocking layer.
  • the layer When a layer containing a compound represented by the formulas (1) to (4) (cathode side adjacent layer) is formed between the phosphorescent light emitting layer 40 and the electron transport zone 50, the layer functions as a hole blocking layer. It can also function as an exciton blocking layer.
  • the barrier layer (blocking layer) is a layer having a function of a carrier movement barrier or an exciton diffusion barrier.
  • the organic layer for preventing electrons from leaking from the light-emitting layer to the hole transport zone can be defined mainly as an electron barrier layer, and the organic layer for preventing holes from leaking from the light-emitting layer to the electron transport zone is defined as a hole barrier. Can be defined as a layer.
  • an exciton blocking layer is an organic layer for preventing triplet excitons generated in the light emitting layer from diffusing into a peripheral layer having triplet energy lower than that of the light emitting layer. May be defined.
  • the compounds represented by the formulas (1) to (4) may be used in a layer adjacent to the phosphorescent light emitting layer 40 and further used in other organic thin film layers bonded to the adjacent layer.
  • the compounds represented by the formulas (1) to (4) can be suitably used as a material for the space layer formed between the light emitting layers.
  • the organic EL device of the present invention preferably has at least one of an electron donating dopant and an organometallic complex in an interface region between the cathode and the organic thin film layer. 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 transport layer or the electron injection layer in the electron transport zone 50 preferably contains a compound represented by formulas (1) to (4) and an electron donating dopant. Thereby, the drive voltage of an organic EL element can further be reduced.
  • Examples of 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.
  • Examples of 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 preferable.
  • K, Rb, and Cs are preferred, Rb and Cs are 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).
  • Ca calcium
  • strontium strontium
  • Ba barium
  • a work function of 2.9 eV or less is particularly preferable.
  • 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), include such terbium fluoride (TbF 3) is, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
  • the electron donating dopant and the organometallic complex it is preferable to form a layer or an island in the interface region.
  • a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material.
  • a method of dispersing at least one of the donor dopant and the organometallic complex is preferable.
  • the dispersion concentration is usually organic substance: electron donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.
  • At least one of the electron donating dopant and the organometallic complex is formed in a layered form
  • at least one of the electron donating dopant and the organometallic complex is formed.
  • These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
  • an electron donating dopant and an organometallic complex is formed in an island shape
  • a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
  • the hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less.
  • inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.
  • a glass plate, a polymer plate or the like can be used as the substrate.
  • the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.
  • the anode is made of, for example, a conductive material, and a conductive material having a work function larger than 4 eV is suitable.
  • the conductive material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and their alloys, ITO substrate, tin oxide used for NESA substrate, indium oxide, and the like.
  • examples thereof include metal oxides and organic conductive resins such as polythiophene and polypyrrole.
  • the anode may be formed with a layer structure of two or more layers if necessary.
  • the cathode is made of, for example, a conductive material, and a conductive material having a work function smaller than 4 eV is suitable.
  • the conductive material include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof.
  • the alloy 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 may be formed with a layer structure of two or more layers, and the cathode can be produced by forming a thin film from the conductive material by a method such as vapor deposition or sputtering.
  • the transmittance of the cathode for light emission is preferably greater 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.
  • each layer of the organic EL device of the present invention a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
  • a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating
  • a wet film forming method such as spin coating, dipping, or flow coating
  • the film thickness of each layer 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.
  • Synthesis Example 2 (Synthesis of Compound 8) (1) Synthesis of intermediate G Under an argon atmosphere, 4.95 g (8.6 mmol) of Pd (dba) 2 and 5.8 g (21 mmol) of tricyclohexylphosphine were added to 1.5 L of 1,4-dioxane, and then 80.2 g of bis (pinacolato) diboron ( 316 mmol), 42.2 g (420 mmol) of potassium acetate, and 100 g (286 mmol) of intermediate F were sequentially charged to the reaction solution at room temperature.
  • Synthesis Example 3 Synthesis of Compound 9) Similar to Synthesis Example 2 (3) except that Intermediate J (for example, synthesized by the method described in WO2013-038650) was used instead of dibenzofuran-2-boronic acid in Synthesis Example 2 (3).
  • Synthesis Example 6 Synthesis of Compound 20
  • Compound 20 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5) except that pivaloyl chloride was used instead of propionyl chloride in Synthesis Example 1 (3).
  • m / e 656 with respect to the molecular weight of 656.
  • Synthesis Example 8 (Synthesis of Compound 5)
  • the compound was prepared in the same manner as in Synthesis Example 1 (5), except that Intermediate K (for example, synthesized by the method described in EP2477172) was used instead of Intermediate E. 5 was synthesized.
  • Intermediate K for example, synthesized by the method described in EP2477172
  • Synthesis Example 9 (Synthesis of Compound 3)
  • 8- (dibenzofuran-2-yl) dibenzofuran-2-boronic acid (for example, synthesized by the method described in WO2013-038650) was used in place of Intermediate H.
  • Compound 3 was synthesized in the same manner as in Synthesis Example 2 (2).
  • m / e 602 with respect to molecular weight 602.
  • Synthesis Example 10 (Synthesis of Compound 4)
  • 1-bromo-4-iodobenzene was used instead of 1-bromo-3-iodobenzene
  • Synthesis Example 1 (3) n-butyryl chloride was used instead of propionyl chloride.
  • compound 4 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5).
  • m / e 642 with respect to the molecular weight 642.
  • Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode (manufactured by Geomatic) was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and further subjected to UV (Ultraviolet) ozone cleaning for 30 minutes. .
  • the glass substrate with the transparent electrode thus cleaned is attached to the substrate holder of the vacuum evaporation apparatus, and first, on the surface of the glass substrate on which the transparent electrode line is formed, the transparent electrode is covered, HTM1 was deposited with a thickness of 20 nm to obtain a hole injection layer. Subsequently, HTM2 was vapor-deposited with a thickness of 60 nm on this film to obtain a hole transport layer.
  • H-1 as a phosphorescent host material and D-1 as a phosphorescent material were co-evaporated at a thickness of 50 nm to obtain a phosphorescent layer.
  • the concentration of H-1 in the phosphorescent light emitting layer was 80% by mass, and the concentration of D-1 was 20% by mass.
  • Compound 1 was deposited on the phosphorescent light emitting layer with a thickness of 10 nm to obtain a first electron transporting layer.
  • ETM1 with a thickness of 10 nm to obtain a second electron transporting layer
  • 1 nm thick LiF and 80 nm thick metal Al were sequentially laminated to obtain a cathode. Note that LiF, which is an electron injecting electrode, was formed at a rate of 1 ⁇ / min.
  • Example 2 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound 1 was used instead of ETM1 as the material for the second electron transport layer. The results are shown in Table 1.
  • Example 3 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the following compound 2 was used instead of compound 1 as a material for the first electron transport layer. The results are shown in Table 1.
  • Example 4 An organic EL device was produced in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 as the material for the first electron transport layer, and Compound 2 was used instead of ETM1 as the material for the second electron transport layer. And evaluated. The results are shown in Table 1.
  • Example 5 An organic EL device was prepared in the same manner as in Example 1, except that the following compound H-2 was used instead of H-1 as the phosphorescent host material, and compound 2 was used instead of compound 1 as the material of the first electron transport layer. Prepared and evaluated. The results are shown in Table 1.
  • Example 6 An organic EL device was prepared in the same manner as in Example 1 except that the following compound H-3 was used instead of H-1 as the phosphorescent host material, and compound 2 was used instead of compound 1 as the material for the first electron transport layer. Prepared and evaluated. The results are shown in Table 1.
  • Comparative Example 1 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound A was used instead of Compound 1 as the material for the first electron transport layer. The results are shown in Table 1.
  • Comparative Example 2 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound B was used instead of Compound 1 as the material for the first electron transport layer. The results are shown in Table 1.
  • Comparative Example 3 An organic EL device was produced in the same manner as in Example 1 except that the following HA was used in place of H-1 as the phosphorescent host material, and compound 2 was used in place of compound 1 as the material for the first electron transport layer. And evaluated. The results are shown in Table 1.
  • ⁇ edge means that when the phosphorescence spectrum is represented by taking the phosphorescence intensity on the vertical axis and the wavelength on the horizontal axis, the tangent line is drawn with respect to the rising edge on the short wavelength side of the phosphorescence spectrum. Means the wavelength value (unit: nm) of the intersection.
  • an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. and an optional component for low temperature measurement were used.
  • the device of the example can obtain a device having a lower voltage, higher efficiency, and longer life than the device of the comparative example.
  • the effect of lowering the voltage and increasing the efficiency is great.
  • a benzimidazole compound having a high triplet energy is used as an electron transport layer material, and a host material having a carbazole ring and a dibenzofuran ring (or dibenzothiophene ring) in the same skeleton and having a high triplet energy is suitable.
  • This is due to the effect of the combination. That is, the high triplet energy necessary for blue phosphorescence emission is confined in the device and the carrier balance in the device is appropriately adjusted.
  • Examples 7-25 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that compounds 3 to 21 were used in place of compound 1 as the material for the first electron transport layer. The results are shown in Table 3.
  • Examples 26-29 As in Example 1, except that H-2 was used as the phosphorescent host material instead of H-1, and compounds 4, 6, 9, and 19 were used instead of compound 1 as the material for the first electron transport layer, respectively. Thus, an organic EL device was produced and evaluated. The results are shown in Table 3.
  • the device of the example can obtain a device with low voltage, high efficiency and long life.
  • the effect of lowering the voltage and increasing the efficiency is great.
  • a benzimidazole compound having a high triplet energy is used as an electron transport layer material, and a host material having a carbazole ring and a dibenzofuran ring (or dibenzothiophene ring) in the same skeleton and having a high triplet energy is suitable.
  • 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 an instrument, a display board, a marker lamp, and an illumination.

Abstract

In the present invention, an organic electroluminescence element has, between a positive electrode and a negative electrode, two or more organic thin film layers that include a light-emitting layer. The light-emitting layer contains at least one compound represented by formula (1) and the organic thin film layer that contacts the light-emitting layer on the negative pole side thereof contains at least one benzimidazole compound represented by formula (A).

Description

有機エレクトロルミネッセンス素子Organic electroluminescence device
　本発明は、有機エレクトロルミネッセンス素子に関する。 The present invention relates to an organic electroluminescence element.
　有機エレクトロルミネッセンス（ＥＬ）素子には、蛍光型及び燐光型があり、それぞれの発光メカニズムに応じ、最適な素子設計が検討されている。燐光型の有機ＥＬ素子については、その発光特性から、蛍光素子技術の単純な転用では高性能な素子が得られないことが知られている。その理由は、一般的に以下のように考えられている。
　燐光発光は、三重項励起子を利用した発光であるため、発光層に用いる化合物のエネルギーギャップが大きい必要がある。これは、ある化合物のエネルギーギャップ（以下、一重項エネルギーともいう。）の値は、通常、その化合物の三重項エネルギー（本発明では、最低励起三重項状態と基底状態とのエネルギー差をいう。）の値よりも大きいためである。 Organic electroluminescence (EL) elements include a fluorescent type and a phosphorescent type, and an optimum element design has been studied according to each light emission mechanism. With respect to phosphorescent organic EL elements, it is known from their light emission characteristics that high-performance elements cannot be obtained by simple diversion of fluorescent element technology. The reason is generally considered as follows.
Since phosphorescent light emission is light emission using triplet excitons, the energy gap of the compound used for the light emitting layer needs to be large. This is because the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).
　燐光発光性ドーパント材料の三重項エネルギーを効率的に発光層内に閉じ込めるためには、まず、燐光発光性ドーパント材料の三重項エネルギーよりも大きい三重項エネルギーのホスト材料を発光層に用いなければならない。 In order to efficiently confine the triplet energy of the phosphorescent dopant material in the light emitting layer, a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must first be used for the light emitting layer. .
　有機ＥＬ素子の駆動電圧を低減するためには、電荷注入性もしくは電荷輸送性に優れる材料を用いる必要がある。しかし、このように電荷注入性、電荷輸送性に優れる材料を用いる場合、駆動電圧が低減する代わりに、発光層内の電荷バランスが悪化し、素子の短寿命化に繋がるケースがある。即ち素子の寿命を維持した上で、駆動電圧を低減する電荷輸送材料が必要となる。 In order to reduce the driving voltage of the organic EL element, it is necessary to use a material having excellent charge injection property or charge transport property. However, in the case of using such a material excellent in charge injection property and charge transport property, there is a case in which, instead of reducing the driving voltage, the charge balance in the light emitting layer is deteriorated and the life of the device is shortened. That is, a charge transport material that reduces the driving voltage while maintaining the lifetime of the element is required.
　以上のような理由から、燐光型の有機ＥＬ素子の高性能化には、蛍光型の有機ＥＬ素子と異なる材料選択及び素子設計が必要になっている。
　材料研究は鋭意行われており、いくつかの報告がなされている（特許文献１～３） For the reasons described above, material enhancement and element design different from those of fluorescent organic EL elements are required for enhancing the performance of phosphorescent organic EL elements.
Material research has been conducted intensively and several reports have been made (Patent Documents 1 to 3).
　特許文献１及び特許文献２には、ベンズイミダゾール化合物が例示され、電子輸送層材料として用いられているが、組み合わせている発光層のホスト材料の三重項エネルギーが小さく、効率が低い。また、組み合わせるホスト材料がジベンゾフラン環やジベンゾチオフェン環を含まない構造であるため、電荷の注入性・輸送性が低く、電圧が高い傾向がある。 In Patent Document 1 and Patent Document 2, benzimidazole compounds are exemplified and used as an electron transport layer material. However, the triplet energy of the host material of the combined light emitting layer is small and the efficiency is low. In addition, since the host material to be combined has a structure that does not include a dibenzofuran ring or a dibenzothiophene ring, the charge injecting / transporting property is low and the voltage tends to be high.
　特許文献３には、ベンズイミダゾール化合物が例示され、電子輸送層材料として用いられているが、それらの三重項エネルギーは小さく、発光層のエネルギーが電子輸送層側に漏れてしまうため、効率が低くなる。 Patent Document 3 exemplifies benzimidazole compounds and is used as an electron transport layer material, but their triplet energy is small, and the energy of the light emitting layer leaks to the electron transport layer side, so the efficiency is low. Become.
特開２００９－１５５３００号公報JP 2009-155300 A 特開２００９－１５８８４８号公報JP 2009-158848 A 特開２０１０－１１８５９１号公報JP 2010-118591 A
　本発明の目的は、低電圧かつ長寿命な有機ＥＬ素子を提供することである。 An object of the present invention is to provide an organic EL element having a low voltage and a long lifetime.
　本発明者らは鋭意研究した結果、電子注入輸送性に優れた特定の構造を有するベンズイミダゾール化合物を発光層に隣接する層に用い、特定の構造を有する化合物を発光層に用いる組み合わせによって、三重項エネルギーを電子輸送層側へ漏れるのを抑制することができ、低電圧、高効率、長寿命な有機ＥＬ素子が得られることを見出した。 As a result of diligent research, the inventors of the present invention have used a benzimidazole compound having a specific structure excellent in electron injecting and transporting properties for a layer adjacent to the light emitting layer, and a combination using a compound having a specific structure for the light emitting layer. It was found that leakage of the term energy to the electron transport layer side can be suppressed, and an organic EL element having low voltage, high efficiency, and long life can be obtained.
　本発明によれば、以下の有機ＥＬ素子等が提供される。
１．陽極と陰極との間に、発光層を含む２層以上の有機薄膜層を有し、
　前記発光層が、下記式（１）で表わされる化合物を少なくとも１つ以上含み、
　前記発光層の陰極側で発光層と接する有機薄膜層が下記式（Ａ）で表わされるベンズイミダゾール化合物を少なくとも１つ以上含む、
　有機エレクトロルミネッセンス素子。
Figure JPOXMLDOC01-appb-C000001
 （式（１）中、
　Ｇ１～Ｇ６は、それぞれ独立に、Ｃ－Ｒ１又は窒素原子である。
　Ｇ１１～Ｇ１８は、それぞれ独立に、Ｃ－Ｒ２又は窒素原子である。
　Ｒ及びＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールオキシ基、置換もしくは無置換の環形成炭素数６～１８のアリールチオ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールチオ基、置換もしくは無置換の環形成炭素数６～１８のアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換のフルオロアルキル基、置換もしくは無置換のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ１が存在するとき、複数のＲ１は、互いに同一又は異なっていてもよい。
　但し、Ｇ２及び／又はＧ５がＣ－Ｒ１である場合は、Ｇ２及びＧ５のＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
　Ｒ２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２が存在するときは、それぞれのＲ２は同一又は異なっていてもよい。
　Ｒ、Ｒ１、Ｒ２が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘは、酸素原子又は硫黄原子を表す。）
Figure JPOXMLDOC01-appb-C000002
 （式（Ａ）中、Ｒａ～Ｒｄ、Ｒｅ～Ｒｆ、Ｒｈ～Ｒｉ、Ｒｊ～Ｒｋ及びＲｍ～Ｒｎは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｒｇ及びＲｌは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
　但し、Ｒｅ～Ｒｆ、Ｒｈ～Ｒｉ、Ｒｊ～Ｒｋ及びＲｍ～Ｒｎの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、又は置換もしくは無置換のジベンゾチオフェニル基である。
　Ａｒ１は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
　Ａｒ２は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
　Ｒａ～Ｒｎ、Ａｒ１及びＡｒ２が置換基を有する場合の当該置換基Ｒ’’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　ｍ及びｎは、それぞれ０又は１である。
　ｏ及びｐは、それぞれ０～３の整数である。
　但し、ｍ、ｎ、ｏ及びｐは、ｍ＋ｏ≧１及びｎ＋ｐ≧１を満たす。
　ｏが２又は３である場合、複数のＡｒ１は互いに同じでも異なってもよい。
　ｐが２又は３である場合、複数のＡｒ２は互いに同じでも異なってもよい。）
２．前記式（１）で表わされる化合物が、下記式（２ａ）で表わされる化合物、下記式（２ｂ）で表わされる化合物、又は下記式（２ｃ）で表わされる化合物である１に記載の有機エレクトロルミネッセンス素子。
Figure JPOXMLDOC01-appb-C000003
 （式（２ａ）～（２ｃ）中、
　Ｇ２１１～Ｇ２１４は、それぞれ独立に、Ｃ－Ｒ２１又は窒素原子である。
　Ｇ２２１～Ｇ２２８は、それぞれ独立に、Ｃ－Ｒ２２又は窒素原子である。
　Ｇａ～Ｇｋはそれぞれ独立に、Ｃ－Ｒ２３又は窒素原子である。
　Ｒ２１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２１が存在する場合、複数のＲ２１は、それぞれ同一又は異なっていてもよい。
　Ｒ２２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２２が存在する場合、複数のＲ２２は、それぞれ同一又は異なっていてもよい。
　Ｒ２３は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２３が存在する場合、複数のＲ２３は、それぞれ同一又は異なっていてもよい。
　Ｒ２１、Ｒ２２及びＲ２３が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘ１は、酸素原子、又は硫黄原子である。
　Ｘ２は、酸素原子、硫黄原子、又は＝Ｃ（ＣＨ３）２である。）
３．前記式（１）で表わされる化合物が、下記式（３ａ）で表わされる化合物、下記式（３ｂ）で表わされる化合物、又は下記式（３ｃ）で表わされる化合物である１に記載の有機エレクトロルミネッセンス素子。
Figure JPOXMLDOC01-appb-C000004
 （式（３ａ）～式（３ｃ）中、
　Ｙは、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成原子数５～７の単環ヘテロ芳香族環基、又は下記式（３－１）で表される基である。
　Ｇ３１１～Ｇ３１７、Ｇ３２１～Ｇ３２７、及びＧ３３１～Ｇ３３７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子である。
　Ｒ３１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ３１が存在するときは、複数のＲ３１は、それぞれ同一又は異なっていてもよい。
　Ｌ３は、単結合、酸素原子を含む２価の連結基、ケイ素原子を含む２価の連結基、硫黄原子を含む２価の連結基、炭素数１～５のアルキレン基、環形成炭素数３～６のシクロアルキレン基、環形成炭素数６～１８の芳香族炭化水素環基、又は環形成原子数５～１８のヘテロ芳香族環基である。
　Ｒ３１が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、フルオロアルキル基、フルオロアルコキシ基又はシアノ基である。
　Ｘ３は、酸素原子又は硫黄原子である。）
Figure JPOXMLDOC01-appb-C000005
 （式（３－１）中、
　＊は、窒素原子との結合を示す。
　Ｇ３４１～Ｇ３４７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子であり、Ｒ３１は式（３ａ）～式（３ｃ）のＲ３１と同じである。
　Ｘ３１は、置換基を有する窒素原子、酸素原子又は硫黄原子である。）
４．前記式（１）で表わされる化合物が、下記式（４）で表わされる化合物である１に記載の有機エレクトロルミネッセンス素子。
Figure JPOXMLDOC01-appb-C000006
 （式（４）中、
　Ｒ４１、Ｒ４２及びＲ４３は、それぞれ独立に、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、又は置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基である。
　Ｒ４１、Ｒ４２及びＲ４３は、互いに直接結合して環を形成してもよいし、酸素原子を介して結合して環を形成してもよいし、硫黄原子を介して結合して環を形成してもよいし、又はケイ素原子を介して結合して環を形成してもよい。
　Ｇ４１～Ｇ４４は、それぞれ独立に、Ｃ－Ｒ４４又は窒素原子である。
　Ｒ４４は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ４４が存在する場合、複数のＲ４４は、それぞれ同一又は異なっていてもよい。
　Ｇ４１１～Ｇ４１８は、それぞれ独立に、Ｃ－Ｒ４５又は窒素原子である。
　Ｒ４５は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ４５が存在する場合、複数のＲ４５は、それぞれ同一又は異なっていてもよい。
　Ｒ４１、Ｒ４２、Ｒ４３、Ｒ４４及びＲ４５が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘ４は、酸素原子又は硫黄原子である。）
５．前記式（Ａ）のＲｆ、Ｒｈ、Ｒｋ及びＲｍの少なくとも１つが、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基である１～４のいずれかに記載の有機エレクトロルミネッセンス素子。
６．前記式（Ａ）のＲｆ及びＲｈの両方、又は前記式（Ａ）のＲｋ及びＲｍの両方が、それぞれ置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基である１～５のいずれかに記載の有機エレクトロルミネッセンス素子。
７．前記式（Ａ）のＡｒ１が、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基である１～６のいずれかに記載の有機エレクトロルミネッセンス素子。
８．前記式（Ａ）のＡｒ２が、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基である１～７のいずれかに記載の有機エレクトロルミネッセンス素子。
９．前記発光層が燐光発光材料を含み、
　前記燐光発光材料が、イリジウム（Ｉｒ）、オスミウム（Ｏｓ）及び白金（Ｐｔ）から選択される１種以上の金属原子のオルトメタル化錯体である１～８のいずれかに記載の有機エレクトロルミネッセンス素子。
１０．前記陰極と前記有機薄膜層との界面領域が電子供与性ドーパントを含む１～９のいずれかに記載の有機エレクトロルミネッセンス素子。
１１．下記式（ａ）で表される化合物。
Figure JPOXMLDOC01-appb-C000007
 （式（ａ）中、Ｒは、置換もしくは無置換の炭素数１～２０のアルキル基、又は置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基である。
　Ｒａ～Ｒｄ、及びＲｊ～Ｒｎは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　但し、Ｒｍ及びＲｋの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基である。
　Ａｒ２は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
　ｎは、０又は１である。
　ｐは、０又は１である。
　ｎ＋ｐ≧１である。）
１２．前記式（ａ）において、Ｒｍ及びＲｋの両方が、それぞれ独立して、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基である１１に記載の化合物。
１３．前記式（ａ）において、Ｒｍ及びＲｋの少なくとも１つが、置換もしくは無置換のカルバゾリル基である１１に記載の化合物。 According to the present invention, the following organic EL elements and the like are provided.
1. Having two or more organic thin film layers including a light emitting layer between the anode and the cathode;
The light emitting layer contains at least one compound represented by the following formula (1),
The organic thin film layer in contact with the light emitting layer on the cathode side of the light emitting layer contains at least one benzimidazole compound represented by the following formula (A),
Organic electroluminescence device.
Figure JPOXMLDOC01-appb-C000001
 (In the formula (1),
G 1 to G 6 are each independently C—R 1 or a nitrogen atom.
G 11 to G 18 are each independently C—R 2 or a nitrogen atom.
R and R 1 are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 18 ring atoms, substituted or unsubstituted arylthio group having 6 to 18 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 18 ring atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted ring atom number 5-18 heteroarylsulfonyl group, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted fluoroalkyl group, substituted or An unsubstituted fluoroalkoxy group or a cyano group.
When a plurality of CR 1 are present, the plurality of R 1 may be the same as or different from each other.
However, if G 2 and / or G 5 is a C-R 1, R 1 of G 2 and G 5 are each independently 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
Each R 2 independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 2 are present, each R 2 may be the same or different.
When R, R 1 and R 2 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms. Alkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, and 5 to 18 ring atoms. A heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X represents an oxygen atom or a sulfur atom. )
Figure JPOXMLDOC01-appb-C000002
 (In the formula (A), Ra to Rd, Re to Rf, Rh to Ri, Rj to Rk and Rm to Rn are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted group. Or an unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted Substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms A cyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 2 It is a fluoroalkoxy group or a cyano group.
Rg and Rl are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon number, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
Provided that at least one of Re to Rf, Rh to Ri, Rj to Rk, and Rm to Rn is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or A substituted or unsubstituted dibenzothiophenyl group;
Ar 1 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, a substituted or unsubstituted metabiphenylyl group or metabiphenylylene group. Substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,6-pyridylene group Group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted or unsubstituted 2-dibenzothiophenyl Group or 2,8-dibenzothiophenylene group, or substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group. Metabiphenylyl group or metabiphenylylene group, substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
When Ra to Rn, Ar 1 and Ar 2 have a substituent, the substituent R ″ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number. An alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, and the number of ring atoms A heteroaromatic cyclic group having 5 to 18 carbon atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
m and n are each 0 or 1.
o and p are each an integer of 0 to 3.
However, m, n, o, and p satisfy m + o ≧ 1 and n + p ≧ 1.
When o is 2 or 3, the plurality of Ar 1 may be the same as or different from each other.
When p is 2 or 3, the plurality of Ar 2 may be the same as or different from each other. )
2. 2. The organic electroluminescence according to 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (2a), a compound represented by the following formula (2b), or a compound represented by the following formula (2c). element.
Figure JPOXMLDOC01-appb-C000003
 (In the formulas (2a) to (2c),
G 211 to G 214 are each independently C—R 21 or a nitrogen atom.
G 221 to G 228 are each independently C—R 22 or a nitrogen atom.
Ga to Gk are each independently C—R 23 or a nitrogen atom.
R 21 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 21 are present, the plurality of R 21 may be the same or different from each other.
R 22 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 22 are present, the plurality of R 22 may be the same or different from each other.
R 23 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 23 are present, the plurality of R 23 may be the same or different from each other.
When R 21 , R 22 and R 23 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms An 18 heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X 1 is an oxygen atom or a sulfur atom.
X 2 is an oxygen atom, a sulfur atom, or ═C (CH 3 ) 2 . )
3. 2. The organic electroluminescence according to 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (3a), a compound represented by the following formula (3b), or a compound represented by the following formula (3c). element.
Figure JPOXMLDOC01-appb-C000004
 (In the formulas (3a) to (3c),
Y represents a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monocyclic heteroaromatic ring group having 5 to 7 ring atoms, or the following formula (3- It is group represented by 1).
G 311 to G 317 , G 321 to G 327 , and G 331 to G 337 are each independently C—R 31 or a nitrogen atom.
R 31 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 31 are present, the plurality of R 31 may be the same or different from each other.
L 3 is a single bond, a divalent linking group containing an oxygen atom, a divalent linking group containing a silicon atom, a divalent linking group containing a sulfur atom, an alkylene group having 1 to 5 carbon atoms, or the number of ring-forming carbon atoms. A cycloalkylene group having 3 to 6 carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a heteroaromatic ring group having 5 to 18 ring atoms.
When R 31 has a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a ring Cycloalkoxy group having 3 to 20 carbon atoms, aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, aryloxy group having 6 to 18 ring carbon atoms, heteroaromatic ring having 5 to 18 ring atoms Group, silyl group, fluorine atom, fluoroalkyl group, fluoroalkoxy group or cyano group.
X 3 is an oxygen atom or a sulfur atom. )
Figure JPOXMLDOC01-appb-C000005
 (In the formula (3-1),
* Indicates a bond with a nitrogen atom.
G 341 ~ G 347 are each independently C-R 31 or a nitrogen atom, R 31 is the same as R 31 in the formula (3a) ~ formula (3c).
X 31 is a nitrogen atom, oxygen atom or sulfur atom having a substituent. )
4). 2. The organic electroluminescence device according to 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (4).
Figure JPOXMLDOC01-appb-C000006
 (In formula (4),
R 41 , R 42 and R 43 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted group. It is an aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms.
R 41 , R 42 and R 43 may be directly bonded to each other to form a ring, may be bonded through an oxygen atom to form a ring, or may be bonded through a sulfur atom to form a ring. Or may be bonded via a silicon atom to form a ring.
G 41 to G 44 each independently represents C—R 44 or a nitrogen atom.
R 44 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
When a plurality of C—R 44 are present, the plurality of R 44 may be the same or different from each other.
G 411 to G 418 are each independently C—R 45 or a nitrogen atom.
R 45 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
When a plurality of C—R 45 are present, the plurality of R 45 may be the same or different from each other.
When R 41 , R 42 , R 43 , R 44 and R 45 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 20 ring carbon atoms. A group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, A heteroaromatic cyclic group having 5 to 18 ring atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X 4 is an oxygen atom or a sulfur atom. )
5. In the formula (A), at least one of Rf, Rh, Rk and Rm is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl group, substituted or unsubstituted 5. The organic electroluminescence device according to any one of 1 to 4, which is a 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group.
6). Both Rf and Rh in the formula (A), or both Rk and Rm in the formula (A) are substituted or unsubstituted carbazolyl groups, substituted or unsubstituted azacarbazolyl groups, substituted or unsubstituted 2- Any one of 1 to 5 which is a dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group The organic electroluminescent element of description.
7). Ar 1 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted 2-dibenzo group. 7. The organic electroluminescence device according to any one of 1 to 6, which is a furanyl group or a 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or a 2,8-dibenzothiophenylene group.
8). Ar 2 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group. Any one of 1 to 7 which is a substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group An organic electroluminescence device according to any one of the above.
9. The light emitting layer includes a phosphorescent material;
9. The organic electroluminescence device according to any one of 1 to 8, wherein the phosphorescent material is an orthometalated complex of one or more metal atoms selected from iridium (Ir), osmium (Os), and platinum (Pt). .
10. 10. The organic electroluminescence device according to any one of 1 to 9, wherein an interface region between the cathode and the organic thin film layer contains an electron donating dopant.
11. A compound represented by the following formula (a).
Figure JPOXMLDOC01-appb-C000007
 (In the formula (a), R represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
Ra to Rd and Rj to Rn are each independently 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 ring carbon atoms, substituted or unsubstituted, Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group; A fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
However, at least one of Rm and Rk is a substituted or unsubstituted carbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted A substituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group.
Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group. Metabiphenylyl group or metabiphenylylene group, substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
n is 0 or 1.
p is 0 or 1.
n + p ≧ 1. )
12 In the formula (a), each of Rm and Rk independently represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted group. 12. The compound according to 11, which is a dibenzothiophenyl group, a substituted or unsubstituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group.
13. 12. The compound according to 11, wherein in the formula (a), at least one of Rm and Rk is a substituted or unsubstituted carbazolyl group.
　本発明によれば、低電圧、高効率かつ長寿命な有機ＥＬ素子が提供できる。 According to the present invention, an organic EL element with low voltage, high efficiency and long life can be provided.
本発明の有機ＥＬ素子の一実施形態を示す図である。It is a figure which shows one Embodiment of the organic EL element of this invention. 本発明の有機ＥＬ素子の他の実施形態を示す図である。It is a figure which shows other embodiment of the organic EL element of this invention.
　本発明の有機ＥＬ素子は、陽極と陰極との間に、発光層を含む２層以上の有機薄膜層を有し、発光層が、下記式（１）で表わされる化合物を少なくとも１つ以上含み、発光層の陰極側で発光層と接する有機薄膜層が下記式（Ａ）で表わされるベンズイミダゾール化合物を少なくとも１つ以上含む。
　以下、これら化合物について説明する。
Figure JPOXMLDOC01-appb-C000008
 The organic EL device of the present invention has two or more organic thin film layers including a light emitting layer between an anode and a cathode, and the light emitting layer contains at least one compound represented by the following formula (1). The organic thin film layer in contact with the light emitting layer on the cathode side of the light emitting layer contains at least one benzimidazole compound represented by the following formula (A).
Hereinafter, these compounds will be described.
Figure JPOXMLDOC01-appb-C000008
［式（Ａ）で表わされる化合物］
　式（Ａ）で表わされる化合物は、ベンズイミダゾール骨格を有する下記化合物である。
Figure JPOXMLDOC01-appb-C000009
 （式（Ａ）中、Ｒａ～Ｒｄ、Ｒｅ～Ｒｆ、Ｒｈ～Ｒｉ、Ｒｊ～Ｒｋ及びＲｍ～Ｒｎは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｒｇ及びＲｌは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
　但し、Ｒｅ及びＲｆ、Ｒｈ及びＲｉ、Ｒｊ及びＲｋ、並びにＲｍ及びＲｎの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、又は置換もしくは無置換のジベンゾチオフェニル基である。
　Ａｒ１は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
　Ａｒ２は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
　Ｒａ～Ｒｎ、Ａｒ１及びＡｒ２が置換基を有する場合の当該置換基Ｒ’’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　ｍ及びｎは、それぞれ０又は１である。
　ｏ及びｐは、それぞれ０～３の整数である。
　但し、ｍ、ｎ、ｏ及びｐは、ｍ＋ｏ≧１及びｎ＋ｐ≧１を満たす。
　ｏが２又は３である場合、複数のＡｒ１は互いに同じでも異なってもよい。
　ｐが２又は３である場合、複数のＡｒ２は互いに同じでも異なってもよい。） [Compound represented by formula (A)]
The compound represented by the formula (A) is the following compound having a benzimidazole skeleton.
Figure JPOXMLDOC01-appb-C000009
 (In the formula (A), Ra to Rd, Re to Rf, Rh to Ri, Rj to Rk and Rm to Rn are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted group. Or an unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted Substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms A cyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 2 It is a fluoroalkoxy group or a cyano group.
Rg and Rl are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon number, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
Provided that at least one of Re and Rf, Rh and Ri, Rj and Rk, and Rm and Rn is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, Or a substituted or unsubstituted dibenzothiophenyl group.
Ar 1 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, a substituted or unsubstituted metabiphenylyl group or metabiphenylylene group. Substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,6-pyridylene group Group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted or unsubstituted 2-dibenzothiophenyl Group or 2,8-dibenzothiophenylene group, or substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group. Metabiphenylyl group or metabiphenylylene group, substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
When Ra to Rn, Ar 1 and Ar 2 have a substituent, the substituent R ″ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number. An alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, and the number of ring atoms A heteroaromatic cyclic group having 5 to 18 carbon atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
m and n are each 0 or 1.
o and p are each an integer of 0 to 3.
However, m, n, o, and p satisfy m + o ≧ 1 and n + p ≧ 1.
When o is 2 or 3, the plurality of Ar 1 may be the same as or different from each other.
When p is 2 or 3, the plurality of Ar 2 may be the same as or different from each other. )
　式（Ａ）で表わされる化合物において、好ましくはＲｆ、Ｒｈ、Ｒｋ、Ｒｍの少なくとも１つが、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基であり、さらに好ましくはＲｆ、Ｒｈ、Ｒｋ、Ｒｍの少なくとも１つが、置換もしくは無置換のＮ－カルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、又は置換もしくは無置換の２－ジベンゾチオフェニル基である。 In the compound represented by the formula (A), preferably at least one of Rf, Rh, Rk, and Rm is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl Group, substituted or unsubstituted 4-dibenzofuranyl group, substituted or unsubstituted 2-dibenzothiophenyl group, or substituted or unsubstituted 4-dibenzothiophenyl group, more preferably Rf, Rh, Rk, At least one of Rm is a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl group, or a substituted or unsubstituted 2-dibenzothiophenyl group.
　式（Ａ）で表わされる化合物において、好ましくはＲｆ及びＲｈの両方、又はＲｋ及びＲｍの両方が、それぞれ置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基である。 In the compound represented by the formula (A), preferably both Rf and Rh, or both Rk and Rm are each a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2- A dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group;
　式（Ａ）で表わされる化合物において、Ａｒ１は、好ましくは単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基であり、より好ましくは単結合、置換もしくは無置換の炭素数１～５のアルキル基もしくはアルキレン基、又は置換もしくは無置換のフェニル基もしくはメタフェニレン基である。 In the compound represented by the formula (A), Ar 1 is preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, substituted or unsubstituted An unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group, more preferably a single bond or a substituted group Alternatively, it is an unsubstituted alkyl group or alkylene group having 1 to 5 carbon atoms, or a substituted or unsubstituted phenyl group or metaphenylene group.
　式（Ａ）で表わされる化合物において、Ａｒ２は、好ましくは単結合、置換もしくは無置換の炭素数１～１０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基であり、より好ましくは単結合、置換もしくは無置換の炭素数１～５のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、又は置換もしくは無置換のパラフェニレン基である。 In the compound represented by the formula (A), Ar 2 is preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted group. An unsubstituted paraphenylene group, a substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group; More preferably a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 5 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, or a substituted or unsubstituted paraphenylene group.
　式（Ａ）で表わされる化合物において、好ましくは、ｍ、ｎはｍ＋ｎ≧１を満たす。 In the compound represented by the formula (A), preferably, m and n satisfy m + n ≧ 1.
　また、式（Ａ）で表わされる化合物は、好ましくは下記式（ａ）で表される化合物である。
　本発明の化合物は下記式（ａ）で表される。
Figure JPOXMLDOC01-appb-C000010
 （式（ａ）中、Ｒは、置換もしくは無置換の炭素数１～２０のアルキル基、又は置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基である。
　Ｒａ～Ｒｄ、Ｒｊ～Ｒｎ、及びＡｒ２は、式（Ａ）と同じである。
　Ｒｍ及びＲｋの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基である。
　ｎは、０又は１である。
　ｐは、０又は１である。
　ｎ＋ｐ≧１である。） The compound represented by the formula (A) is preferably a compound represented by the following formula (a).
The compound of the present invention is represented by the following formula (a).
Figure JPOXMLDOC01-appb-C000010
 (In the formula (a), R represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
Ra to Rd, Rj to Rn, and Ar 2 are the same as in the formula (A).
At least one of Rm and Rk is a substituted or unsubstituted carbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted An azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group;
n is 0 or 1.
p is 0 or 1.
n + p ≧ 1. )
　前記式（ａ）において、Ｒｍ及びＲｋの両方が、それぞれ独立して、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基であると好ましい。 In the formula (a), each of Rm and Rk independently represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted group. A dibenzothiophenyl group, a substituted or unsubstituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group is preferable.
　前記式（ａ）において、Ｒｍ及びＲｋの少なくとも１つが、置換もしくは無置換のカルバゾリル基であると好ましい。 In the formula (a), it is preferable that at least one of Rm and Rk is a substituted or unsubstituted carbazolyl group.
　式（Ａ）で表されるベンズイミダゾール化合物の三重項エネルギーは、好ましくは、２．８５ｅＶ以上であり、より好ましくは、２．９０ｅＶ以上である。 The triplet energy of the benzimidazole compound represented by the formula (A) is preferably 2.85 eV or more, more preferably 2.90 eV or more.
　式（Ａ）で表わされる化合物の具体例を以下に示す。但し、式（Ａ）で表わされる化合物は、下記具体例に限定されない。
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
 Specific examples of the compound represented by the formula (A) are shown below. However, the compound represented by the formula (A) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
　式（Ａ）で表わされる化合物は公知の方法で製造することができ、例えば特開２００９－１５５３００号公報、特開２００９－１５８８４８号公報等に記載の方法で製造することができる。 The compound represented by the formula (A) can be produced by a known method, for example, a method described in JP-A-2009-155300, JP-A-2009-158848, or the like.
［式（１）で表わされる化合物］
　式（１）で表わされる化合物は、下記化合物である。
Figure JPOXMLDOC01-appb-C000018
 （式（１）中、
　Ｇ１～Ｇ６は、それぞれ独立に、Ｃ－Ｒ１又は窒素原子である。
　Ｇ１１～Ｇ１８は、それぞれ独立に、Ｃ－Ｒ２又は窒素原子である。
　Ｒ及びＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールオキシ基、置換もしくは無置換の環形成炭素数６～１８のアリールチオ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールチオ基、置換もしくは無置換の環形成炭素数６～１８のアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ１が存在するとき、複数のＲ１は、互いに同一又は異なっていてもよい。
　但し、Ｇ２及び／又はＧ５がＣ－Ｒ１である場合は、Ｇ２及びＧ５のＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
　Ｒ２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２が存在するときは、それぞれのＲ２は同一又は異なっていてもよい。
　Ｒ、Ｒ１、Ｒ２が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘは、酸素原子又は硫黄原子を表す。） [Compound represented by Formula (1)]
The compound represented by Formula (1) is the following compound.
Figure JPOXMLDOC01-appb-C000018
 (In the formula (1),
G 1 to G 6 are each independently C—R 1 or a nitrogen atom.
G 11 to G 18 are each independently C—R 2 or a nitrogen atom.
R and R 1 are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 18 ring atoms, substituted or unsubstituted arylthio group having 6 to 18 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 18 ring atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted ring atom number 5- to 18-heteroarylsulfonyl group, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted 1 to 20 carbon atoms A fluoroalkyl group, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group;
When a plurality of CR 1 are present, the plurality of R 1 may be the same as or different from each other.
However, if G 2 and / or G 5 is a C-R 1, R 1 of G 2 and G 5 are each independently 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
Each R 2 independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 2 are present, each R 2 may be the same or different.
When R, R 1 and R 2 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms. Alkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, and 5 to 18 ring atoms. A heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X represents an oxygen atom or a sulfur atom. )
　式（１）で表わされる化合物は、好ましくは下記式（２ａ）～（２ｃ）、（３ａ）～（３ｃ）及び（４）で表わされる化合物のいずれかである。
Figure JPOXMLDOC01-appb-C000019
 （式（２ａ）～（２ｃ）中、
　Ｇ２１１～Ｇ２１４は、それぞれ独立に、Ｃ－Ｒ２１又は窒素原子である。
　Ｇ２２１～Ｇ２２８は、それぞれ独立に、Ｃ－Ｒ２２又は窒素原子である。
　Ｇａ～Ｇｋはそれぞれ独立に、Ｃ－Ｒ２３又は窒素原子である。
　Ｒ２１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２１が存在する場合、複数のＲ２１は、それぞれ同一又は異なっていてもよい。
　Ｒ２２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２２が存在する場合、複数のＲ２２は、それぞれ同一又は異なっていてもよい。
　Ｒ２３は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ２３が存在する場合、複数のＲ２３は、それぞれ同一又は異なっていてもよい。
　Ｒ２１、Ｒ２２及びＲ２３が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘ１は、酸素原子、又は硫黄原子である。
　Ｘ２は、酸素原子、硫黄原子、又は＝Ｃ（ＣＨ３）２である。） The compound represented by the formula (1) is preferably any of compounds represented by the following formulas (2a) to (2c), (3a) to (3c) and (4).
Figure JPOXMLDOC01-appb-C000019
 (In the formulas (2a) to (2c),
G 211 to G 214 are each independently C—R 21 or a nitrogen atom.
G 221 to G 228 are each independently C—R 22 or a nitrogen atom.
Ga to Gk are each independently C—R 23 or a nitrogen atom.
R 21 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 21 are present, the plurality of R 21 may be the same or different from each other.
R 22 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 22 are present, the plurality of R 22 may be the same or different from each other.
R 23 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 23 are present, the plurality of R 23 may be the same or different from each other.
When R 21 , R 22 and R 23 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms An 18 heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X 1 is an oxygen atom or a sulfur atom.
X 2 is an oxygen atom, a sulfur atom, or ═C (CH 3 ) 2 . )
Figure JPOXMLDOC01-appb-C000020
 （式（３ａ）～式（３ｃ）中、
　Ｙは、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数２～５の単環ヘテロ芳香族環基、又は下記式（３－１）で表される基である。
　Ｇ３１１～Ｇ３１７、Ｇ３２１～Ｇ３２７、及びＧ３３１～Ｇ３３７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子である。
　Ｒ３１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ３１が存在するときは、複数のＲ３１は、それぞれ同一又は異なっていてもよい。
　Ｌ３は、単結合、酸素原子を含む２価の連結基、ケイ素原子を含む２価の連結基、硫黄原子を含む２価の連結基、炭素数１～５のアルキレン基、環形成炭素数３～６のシクロアルキレン基、環形成炭素数６～１８の芳香族炭化水素環基、又は環形成原子数５～１８のヘテロ芳香族環基である。
　Ｒ３１が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘ３は、酸素原子又は硫黄原子である。）
Figure JPOXMLDOC01-appb-C000021
 （式（３－１）中、
　＊は、窒素原子との結合を示す。
　Ｇ３４１～Ｇ３４７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子であり、Ｒ３１は式（３ａ）～式（３ｃ）のＲ３１と同じである。
　Ｘ３１は、置換基を有する窒素原子、酸素原子又は硫黄原子である。）
Figure JPOXMLDOC01-appb-C000020
 (In the formulas (3a) to (3c),
Y is a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monocyclic heteroaromatic ring group having 2 to 5 ring carbon atoms, or the following formula (3- It is group represented by 1).
G 311 to G 317 , G 321 to G 327 , and G 331 to G 337 are each independently C—R 31 or a nitrogen atom.
R 31 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
When a plurality of C—R 31 are present, the plurality of R 31 may be the same or different from each other.
L 3 is a single bond, a divalent linking group containing an oxygen atom, a divalent linking group containing a silicon atom, a divalent linking group containing a sulfur atom, an alkylene group having 1 to 5 carbon atoms, or the number of ring-forming carbon atoms. A cycloalkylene group having 3 to 6 carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a heteroaromatic ring group having 5 to 18 ring atoms.
When R 31 has a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a ring Cycloalkoxy group having 3 to 20 carbon atoms, aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, aryloxy group having 6 to 18 ring carbon atoms, heteroaromatic ring having 5 to 18 ring atoms A silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X 3 is an oxygen atom or a sulfur atom. )
Figure JPOXMLDOC01-appb-C000021
 (In the formula (3-1),
* Indicates a bond with a nitrogen atom.
G 341 ~ G 347 are each independently C-R 31 or a nitrogen atom, R 31 is the same as R 31 in the formula (3a) ~ formula (3c).
X 31 is a nitrogen atom, oxygen atom or sulfur atom having a substituent. )
Figure JPOXMLDOC01-appb-C000022
 （式（４）中、
　Ｒ４１、Ｒ４２及びＲ４３は、それぞれ独立に、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、又は置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基である。
　Ｒ４１、Ｒ４２及びＲ４３は、互いに直接結合して環を形成してもよいし、酸素原子を介して結合して環を形成してもよいし、硫黄原子を介して結合して環を形成してもよいし、又はケイ素原子を介して結合して環を形成してもよい。
　Ｇ４１～Ｇ４４は、それぞれ独立に、Ｃ－Ｒ４４又は窒素原子である。
　Ｒ４４は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ４４が存在する場合、複数のＲ４４は、それぞれ同一又は異なっていてもよい。
　Ｇ４１１～Ｇ４１８は、それぞれ独立に、Ｃ－Ｒ４５又は窒素原子である。
　Ｒ４５は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　複数のＣ－Ｒ４５が存在する場合、複数のＲ４５は、それぞれ同一又は異なっていてもよい。
　Ｒ４１、Ｒ４２、Ｒ４３、Ｒ４４及びＲ４５が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
　Ｘ４は、酸素原子又は硫黄原子である。）
Figure JPOXMLDOC01-appb-C000022
 (In formula (4),
R 41 , R 42 and R 43 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted group. It is an aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms.
R 41 , R 42 and R 43 may be directly bonded to each other to form a ring, may be bonded through an oxygen atom to form a ring, or may be bonded through a sulfur atom to form a ring. Or may be bonded via a silicon atom to form a ring.
G 41 to G 44 each independently represents C—R 44 or a nitrogen atom.
R 44 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
When a plurality of C—R 44 are present, the plurality of R 44 may be the same or different from each other.
G 411 to G 418 are each independently C—R 45 or a nitrogen atom.
R 45 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
When a plurality of C—R 45 are present, the plurality of R 45 may be the same or different from each other.
When R 41 , R 42 , R 43 , R 44 and R 45 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 20 ring carbon atoms. A group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, A heteroaromatic cyclic group having 5 to 18 ring atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
X 4 is an oxygen atom or a sulfur atom. )
　式（１）、（２ａ）～（２ｃ）、（３ａ）～（３ｃ）及び（４）で表わされる化合物は、好ましくは三重項エネルギーが２．９ｅＶ以上である。 The compounds represented by the formulas (1), (2a) to (2c), (3a) to (3c) and (4) preferably have a triplet energy of 2.9 eV or more.
　式（１）、（２ａ）～（２ｃ）、（３ａ）～（３ｃ）及び（４）で表わされる化合物の具体例を以下に示す。但し、式（１）、（２ａ）～（２ｃ）、（３ａ）～（３ｃ）及び（４）で表わされる化合物は、下記具体例に限定されない。
　Ｘは酸素原子もしくは硫黄原子を表す。
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000039
 Specific examples of the compounds represented by the formulas (1), (2a) to (2c), (3a) to (3c) and (4) are shown below. However, the compounds represented by the formulas (1), (2a) to (2c), (3a) to (3c) and (4) are not limited to the following specific examples.
X represents an oxygen atom or a sulfur atom.
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000039
　以下、式（Ａ）で表わされる化合物、及び式（１）、（２ａ）～（２ｃ）、（３ａ）～（３ｃ）及び（４）で表わされる化合物の各置換基について説明する。
　尚、「環形成炭素」とは飽和環、不飽和環、又は芳香環を構成する炭素原子を意味し、「環形成原子」とはヘテロ環（飽和環、不飽和環、及び芳香環を含む）を構成する炭素原子及びヘテロ原子を意味する。
　また、本願において水素原子には、中性子数が異なる同位体である軽水素（protium）、重水素（deuterium）、三重水素（tritium）を包含する。 Hereinafter, the compound represented by the formula (A) and each substituent of the compounds represented by the formulas (1), (2a) to (2c), (3a) to (3c) and (4) will be described.
The “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring, and the “ring-forming atom” includes a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). ) Is a carbon atom and a hetero atom.
In the present application, the hydrogen atom includes isotopes having different neutron numbers such as light hydrogen (protium), deuterium (deuterium), and tritium.
　アリール基（芳香族炭化水素基）の具体例としては、フェニル基、トリル基、キシリル基、ナフチル基、フェナントリル基、ピレニル基、クリセニル基、ベンゾ［ｃ］フェナントリル基、ベンゾ［ｇ］クリセニル基、ベンゾアントリル基、トリフェニレニル基、フルオレニル基、９，９－ジメチルフルオレニル基、ベンゾフルオレニル基、ジベンゾフルオレニル基、ビフェニル基、ターフェニル基、フルオランテニル基等が挙げられ、好ましくはフェニル基、ビフェニル基、ナフチル基である。
　置換基を有する芳香族炭化水素基としては、トリル基、キシリル基、９，９－ジメチルフルオレニル基等が挙げられる。
　具体例が示すように、アリール基は、縮合アリール基及び非縮合アリール基の両方を含む。 Specific examples of the aryl group (aromatic hydrocarbon group) include phenyl group, tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, Benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, fluoranthenyl group and the like are preferable. Are a phenyl group, a biphenyl group, and a naphthyl group.
Examples of the aromatic hydrocarbon group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.
As specific examples indicate, aryl groups include both fused and non-fused aryl groups.
　ヘテロアリール基（芳香族複素環基、ヘテロ芳香族環基、複素環基）の具体例としては、ピロリル基、ピラゾリル基、ピラジニル基、ピリミジニル基、ピリダジニル基、ピリジル基、トリアジニル基、インドリル基、イソインドリル基、イミダゾリル基、ベンズイミダゾリル基、インダゾリル基、イミダゾ［１，２－ａ］ピリジニル基、フリル基、ベンゾフラニル基、イソベンゾフラニル基、ジベンゾフラニル基、アザジベンゾフラニル基、チオフェニル基、ベンゾチオフェニル基、ジベンゾチオフェニル基、アザジベンゾチオフェニル基、キノリル基、イソキノリル基、キノキサリニル基、キナゾリニル基、ナフチリジニル基、カルバゾリル基、アザカルバゾリル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、オキサゾリル基、オキサジアゾリル基、フラザニル基、ベンズオキサゾリル基、チエニル基、チアゾリル基、チアジアゾリル基、ベンズチアゾリル基、トリアゾリル基、テトラゾリル基等が挙げられ、好ましくは、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基、である。 Specific examples of the heteroaryl group (aromatic heterocyclic group, heteroaromatic ring group, heterocyclic group) include pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group, triazinyl group, indolyl group, Isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, Benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl Group Nazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzthiazolyl group, triazolyl group, tetrazolyl group, etc., preferably A dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group.
　上記アザカルバゾリル基は、例えば２～５個の窒素原子を含むアザカルバゾリル基であり、下記アザカルバゾールから誘導される１価の基が挙げられる。結合手はいずれの窒素原子、いずれの炭素原子上に存在していてもよく、また、いずれの窒素原子、いずれの炭素原子も置換されていてもよい。
Figure JPOXMLDOC01-appb-C000040
 The azacarbazolyl group is, for example, an azacarbazolyl group containing 2 to 5 nitrogen atoms, and examples thereof include monovalent groups derived from the following azacarbazole. The bond may be present on any nitrogen atom or any carbon atom, and any nitrogen atom or any carbon atom may be substituted.
Figure JPOXMLDOC01-appb-C000040
　アルキル基としては、直鎖状、分岐状及び環状のアルキル基がある。直鎖状及び分岐状のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基等が挙げられ、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基が挙げられ、さらに好ましくはメチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、ｓ－ブチル基、ｔ－ブチル基である。
　シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、１－ノルボルニル基、２－ノルボルニル基等が挙げられる。好ましくはシクロペンチル基、シクロヘキシル基である。 Examples of the alkyl group include linear, branched and cyclic alkyl groups. Examples of linear and branched alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl. Group, n-heptyl group, n-octyl group and the like, preferably methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group. More preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and t-butyl group.
Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Preferred are a cyclopentyl group and a cyclohexyl group.
　アルコキシ基は、－ＯＹと表され、Ｙの例として上記のアルキルの例が挙げられる。具体的なアルコキシ基の例としては、メトキシ基、エトキシ基等が挙げられる。
　シクロアルコキシ基は、－ＯＹ２と表され、Ｙ２の例として上記のシクロアルキル基の例が挙げられる。シクロアルコキシ基は、例えばシクロペンチルオキシ基、シクロヘキシルオキシ基である。 The alkoxy group is represented as —OY, and examples of Y include the above alkyl examples. Specific examples of the alkoxy group include a methoxy group and an ethoxy group.
The cycloalkoxy group is represented as —OY 2, and examples of Y 2 include the examples of the cycloalkyl group described above. The cycloalkoxy group is, for example, a cyclopentyloxy group or a cyclohexyloxy group.
　アリールオキシ基は、－ＯＺで表わされ、Ｚの例としては上記アリール基が挙げられる。具体的なアリールオキシ基の例としては、例えばフェノキシ基、ナフチルオキシ基等が挙げられる。
　ヘテロアリールオキシ基は、－ＯＺ’で表わされ、Ｚ’の例としては上記ヘテロアリール基が挙げられる。具体的なヘテロアリールオキシ基の例としては、例えば、（カルバゾール－３－イル）オキシ基、（カルバゾール－４－イル）オキシ基、（ジベンゾフラン－２－イル）オキシ基等が挙げられる。
　アリールカルボニル基は、－ＣＯＺで表わされ、Ｚの例としては上記アリール基が挙げられる。 The aryloxy group is represented by —OZ, and examples of Z include the above aryl groups. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
The heteroaryloxy group is represented by —OZ ′, and examples of Z ′ include the above heteroaryl groups. Specific examples of the heteroaryloxy group include (carbazol-3-yl) oxy group, (carbazol-4-yl) oxy group, (dibenzofuran-2-yl) oxy group, and the like.
The arylcarbonyl group is represented by —COZ, and examples of Z include the above aryl groups.
　アリールチオ基は、－ＳＺで表わされ、Ｚの例としては上記アリール基が挙げられる。
　ヘテロアリールチオ基は、－ＳＺ’で表わされ、Ｚ’の例としては上記ヘテロアリール基が挙げられる。具体的なヘテロアリールオキシ基の例としては、例えば、（カルバゾール－３－イル）チオ基、（カルバゾール－４－イル）チオ基、（ジベンゾフラン－２－イル）チオ基等が挙げられる。
　アリールスルホニル基は、－ＳＯ２Ｚで表わされ、Ｚの例としては上記アリール基が挙げられる。
　ヘテロアリールスルホニル基は、－ＳＯ２Ｚ’で表わされ、Ｚ’の例としては上記ヘテロアリール基が挙げられる。具体的なヘテロアリールオキシ基の例としては、例えば、（カルバゾール－３－イル）スルホニル基、（カルバゾール－４－イル）スルホニル基、（ジベンゾフラン－２－イル）スルホニル基等が挙げられる。 The arylthio group is represented by —SZ, and examples of Z include the above aryl groups.
The heteroarylthio group is represented by —SZ ′, and examples of Z ′ include the above heteroaryl groups. Specific examples of the heteroaryloxy group include (carbazol-3-yl) thio group, (carbazol-4-yl) thio group, (dibenzofuran-2-yl) thio group, and the like.
The arylsulfonyl group is represented by —SO 2 Z, and examples of Z include the above aryl groups.
The heteroarylsulfonyl group is represented by —SO 2 Z ′, and examples of Z ′ include the above heteroaryl groups. Specific examples of the heteroaryloxy group include (carbazol-3-yl) sulfonyl group, (carbazol-4-yl) sulfonyl group, (dibenzofuran-2-yl) sulfonyl group, and the like.
　アラルキル基は、－Ｙ－Ｚと表され、Ｙの例として上記のアルキルの例に対応するアルキレンの例が挙げられ、Ｚの例として上記のアリールの例が挙げられる。アラルキル基のアリール部分は、炭素数が６～２０が好ましく、特に好ましくは６～１２である。アルキル部分は炭素数１～１０が好ましく、特に好ましくは１～６である。例えば、ベンジル基、フェニルエチル基、２－フェニルプロパン－２－イル基等が挙げられる。 The aralkyl group is represented by —Y—Z. Examples of Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples. The aryl part of the aralkyl group preferably has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. The alkyl moiety preferably has 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms. For example, benzyl group, phenylethyl group, 2-phenylpropan-2-yl group and the like can be mentioned.
　ハロゲン化アルキル基としては、上述したアルキル基に１つ以上のハロゲン原子（フッ素原子、塩素原子及び臭素原子が挙げられ、好ましくはフッ素原子である。）が置換した基が挙げられる。具体的には、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、フルオロエチル基、２，２，２－トリフルオロエチル基、ペンタフルオロエチル基等が挙げられる。好ましくは、トリフルオロメチル基、ペンタフルオロエチル基である。
　フルオロアルキル基としては、上述したアルキル基に１つ以上のフッ素原子が置換した基が挙げられる。具体的には、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、フルオロエチル基、２，２，２－トリフルオロエチル基、ペンタフルオロエチル基等が挙げられる。好ましくは、トリフルオロメチル基、ペンタフルオロエチル基である。
　フルオロアルコキシ基としては、上述したアルコキシ基のアルキル部分が１つ以上のフッ素原子で置換された基が挙げられる。具体的には、フルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメトキシ基、フルオロエトキシ基、２，２，２－トリフルオロエトキシ基、ペンタフルオロエトキシ基等が挙げられる。好ましくは、トリフルオロメトキシ基、ペンタフルオロエトキシ基である。 Examples of the halogenated alkyl group include groups in which one or more halogen atoms (a fluorine atom, a chlorine atom and a bromine atom are included, preferably a fluorine atom) are substituted on the above-described alkyl group. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a 2,2,2-trifluoroethyl group, and a pentafluoroethyl group. Preferably, they are a trifluoromethyl group and a pentafluoroethyl group.
Examples of the fluoroalkyl group include groups in which one or more fluorine atoms are substituted on the above-described alkyl group. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a 2,2,2-trifluoroethyl group, and a pentafluoroethyl group. Preferably, they are a trifluoromethyl group and a pentafluoroethyl group.
Examples of the fluoroalkoxy group include groups in which the alkyl portion of the alkoxy group described above is substituted with one or more fluorine atoms. Specific examples include a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a fluoroethoxy group, a 2,2,2-trifluoroethoxy group, and a pentafluoroethoxy group. Preferably, they are a trifluoromethoxy group and a pentafluoroethoxy group.
　置換もしくは無置換のシリル基は、例えばシリル基、アルキルシリル基、ジアルキルアリールシリル基、アルキルジアリールシリル基、トリアリールシリル基を含む。
　置換シリル基は、－Ｓｉ（Ｒａ）（Ｒｂ）（Ｒｃ）と表され、（Ｒａ）、（Ｒｂ）及び（Ｒｃ）の例としては上述したアルキル基、アリール基、ヘテロアリール基等が挙げられる。 The substituted or unsubstituted silyl group includes, for example, a silyl group, an alkylsilyl group, a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
The substituted silyl group is represented by —Si (R a ) (R b ) (R c ), and examples of (R a ), (R b ) and (R c ) include the alkyl group, aryl group, hetero group described above. An aryl group etc. are mentioned.
　置換もしくは無置換のアミノ基は、例えばアリールアミノ基、アルキルアミノ基、アラルキルアミノ基を含む。
　置換アミノ基は、－Ｎ（Ｑａ）（Ｑｂ）と表され、（Ｑａ）及び（Ｑｂ）の例としては上述したアルキル基、アリール基、アラルキル基が挙げられる。 The substituted or unsubstituted amino group includes, for example, an arylamino group, an alkylamino group, and an aralkylamino group.
The substituted amino group is represented by —N (Q a ) (Q b ), and examples of (Q a ) and (Q b ) include the alkyl group, aryl group, and aralkyl group described above.
　アルキレン基、シクロアルキレン基、アリーレン基及びヘテロアリーレン基としては、上述したアルキル基、シクロアルキル基、アリール基及びヘテロアリール基に対応する２価の残基がそれぞれ挙げられる。
　尚、メタビフェニリル基、メタビフェニリレン基、メタターフェニリル基及びメタターフェニリレン基は、それぞれ下記式で表わされる基である。
Figure JPOXMLDOC01-appb-C000041
 Examples of the alkylene group, cycloalkylene group, arylene group, and heteroarylene group include divalent residues corresponding to the above-described alkyl group, cycloalkyl group, aryl group, and heteroaryl group.
In addition, a metabiphenylyl group, a metabiphenylylene group, a metaterphenylyl group, and a metaterphenylylene group are groups represented by the following formulas, respectively.
Figure JPOXMLDOC01-appb-C000041
　式（Ａ）で表わされる化合物は、有機ＥＬ素子の有機薄膜層用材料であり、電子輸送帯域層材料として好適に用いることができ、当該電子輸送帯域層のうち、電子輸送層材料として特に好適に用いることができる。
　式（１）～（４）で表わされる化合物は、有機ＥＬ素子の発光層用材料であり、発光層のホスト材料として好適に用いることができ、青色燐光発光層のホスト材料として特に好適に用いることができる。これは、式（１）～（４）で表わされる化合物は、三重項エネルギーが十分に大きいため、青色の燐光発光性ドーパント材料を使用しても、燐光発光性ドーパント材料の三重項エネルギーを効率的に発光層内に閉じ込めることができるからである。
　式（１）～（４）で表わされる化合物は、青色発光層に限らず、より長波長の光（緑～赤色等）の発光層にも使用できる。 The compound represented by the formula (A) is a material for an organic thin film layer of an organic EL device, and can be suitably used as an electron transport band layer material. Among the electron transport band layers, the compound is particularly suitable as an electron transport layer material. Can be used.
The compounds represented by the formulas (1) to (4) are materials for a light emitting layer of an organic EL device, can be suitably used as a host material for a light emitting layer, and are particularly suitably used as a host material for a blue phosphorescent light emitting layer. be able to. This is because the triplet energy of the compounds represented by the formulas (1) to (4) is sufficiently large, so even if a blue phosphorescent dopant material is used, the triplet energy of the phosphorescent dopant material is efficiently used. This is because it can be confined in the light emitting layer.
The compounds represented by the formulas (1) to (4) can be used not only in the blue light emitting layer but also in the light emitting layer of longer wavelength light (such as green to red).
［素子構成］
　本発明の有機ＥＬ素子では、上述した有機薄膜層及び発光層の素子構成を有していれば、他の構成は特に限定されず、式（Ａ）で表わされる化合物を含む有機薄膜層が発光層の陰極側で隣接している。
　また、発光層は、式（１）～（４）で表わされる化合物を１種単独で、又は２種以上を含んでもよく、好ましくは式（１）～（４）で表わされる化合物の１種類のみを含む。 [Element structure]
In the organic EL device of the present invention, other configurations are not particularly limited as long as the organic thin film layer and the light emitting layer are configured as described above, and the organic thin film layer containing the compound represented by the formula (A) emits light. Adjacent on the cathode side of the layer.
The light emitting layer may contain one or more of the compounds represented by formulas (1) to (4), preferably one of the compounds represented by formulas (1) to (4). Including only.
　本発明の有機ＥＬ素子は公知の素子構成を採用できる。以下、有機ＥＬ素子の形態例を、図面を用いて説明する。
　図１は、本発明の有機ＥＬ素子の一実施形態の層構成を示す概略図である。
　有機ＥＬ素子１は、基板１０上に、陽極２０、正孔輸送帯域３０、燐光発光層４０、電子輸送帯域５０及び陰極６０を、この順で積層した構成を有する。
　正孔輸送帯域３０は、正孔輸送層及び／又は正孔注入層等を意味する。同様に、電子輸送帯域５０は、電子輸送層及び／又は電子注入層等を意味する。これらは形成しなくともよいが、好ましくは１層以上形成する。
　この素子１において有機薄膜層は、正孔輸送帯域３０に設けられる各有機層、燐光発光層４０及び電子輸送帯域５０に設けられる各有機層である。 The organic EL element of the present invention can employ a known element configuration. Hereinafter, the example of an organic EL element is demonstrated using drawing.
FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
The organic EL element 1 has a configuration in which an anode 20, a hole transport zone 30, a phosphorescent light emitting layer 40, an electron transport zone 50, and a cathode 60 are laminated on a substrate 10 in this order.
The hole transport zone 30 means a hole transport layer and / or a hole injection layer. Similarly, the electron transport zone 50 means an electron transport layer and / or an electron injection layer. These need not be formed, but preferably one or more layers are formed.
In this element 1, the organic thin film layer is each organic layer provided in the hole transport zone 30, each phosphor layer and the organic layer provided in the electron transport zone 50.
　図２は、本発明の有機ＥＬ素子の他の実施形態の層構成を示す概略図であり、有機ＥＬ素子２は、燐光発光層と蛍光発光層を積層したハイブリッド型の有機ＥＬ素子の例である。
　有機ＥＬ素子２は、燐光発光層４０と電子輸送帯域５０の間にスペース層４２と蛍光発光層４４を形成した他は、上記有機ＥＬ素子１と同様な構成を有する。燐光発光層４０及び蛍光発光層４４を積層した構成では、燐光発光層４０で形成された励起子を蛍光発光層４４に拡散させないため、蛍光発光層４４と燐光発光層４０の間にスペース層４２を設けることがある。
　尚、式（１）～（４）で表わされる化合物は、三重項エネルギーが大きいため、スペース層として機能できる。 FIG. 2 is a schematic view showing the layer structure of another embodiment of the organic EL element of the present invention. The organic EL element 2 is an example of a hybrid organic EL element in which a phosphorescent light emitting layer and a fluorescent light emitting layer are laminated. is there.
The organic EL element 2 has the same configuration as the organic EL element 1 except that a space layer 42 and a fluorescent light emitting layer 44 are formed between the phosphorescent light emitting layer 40 and the electron transport zone 50. In the configuration in which the phosphorescent light emitting layer 40 and the fluorescent light emitting layer 44 are laminated, the excitons formed in the phosphorescent light emitting layer 40 are not diffused into the fluorescent light emitting layer 44, so that a space layer 42 is provided between the fluorescent light emitting layer 44 and the phosphorescent light emitting layer 40. May be provided.
The compounds represented by the formulas (1) to (4) can function as a space layer because they have a large triplet energy.
　有機ＥＬ素子２において、例えば、燐光発光層４０を黄色発光とし、蛍光発光層４４を青色発光層とすることにより、白色発光の有機ＥＬ素子が得られる。尚、本実施形態では燐光発光層４０及び蛍光発光層４４を１層ずつとしているが、これに限らず、それぞれ２層以上形成してもよく、照明や表示装置等、用途に合わせて適宜設定できる。例えば、白色発光素子とカラーフィルタを利用してフルカラー発光装置とする場合、演色性の観点から、赤、緑、青（ＲＧＢ）、赤、緑、青、黄（ＲＧＢＹ）等、複数の波長領域の発光を含んでいることが好ましい場合がある。 In the organic EL element 2, for example, when the phosphorescent light emitting layer 40 emits yellow light and the fluorescent light emitting layer 44 forms a blue light emitting layer, a white light emitting organic EL element can be obtained. In the present embodiment, the phosphorescent light emitting layer 40 and the fluorescent light emitting layer 44 are formed one by one. However, the present invention is not limited to this, and two or more layers may be formed. it can. For example, when a full color light emitting device is formed using a white light emitting element and a color filter, a plurality of wavelength regions such as red, green, blue (RGB), red, green, blue, yellow (RGBY) are used from the viewpoint of color rendering. In some cases, it may be preferable to include luminescence.
　上述した実施形態の他に、本発明の有機ＥＬ素子は、公知の様々な構成を採用できる。また、発光層の発光は、陽極側、陰極側、又は両側から取り出すことができる。 In addition to the above-described embodiments, the organic EL element of the present invention can employ various known configurations. In addition, light emission of the light emitting layer can be extracted from the anode side, the cathode side, or both sides.
　以下、各層の材料等について説明するが、有機ＥＬ素子の発光層と発光層の陰極側で接する有機薄膜層が式（Ａ）で表わされる化合物を含み、発光層が式（１）～（４）で表わされる化合物の１以上を含むば特に限定されない。有機ＥＬ素子の各層は、公知の材料等を使用できる。
　尚、有機ＥＬ素子が発光層を複数有する場合、複数の発光層のいずれか１つの発光層の陰極側で接する有機薄膜層が式（Ａ）で表わされる化合物を含めばよい。 Hereinafter, materials of each layer will be described. The organic thin film layer in contact with the light emitting layer of the organic EL element on the cathode side contains a compound represented by the formula (A), and the light emitting layer has the formulas (1) to (4). It is not particularly limited as long as it contains one or more of the compounds represented by A known material etc. can be used for each layer of an organic EL element.
In addition, when an organic EL element has two or more light emitting layers, the organic thin film layer which touches the cathode side of any one light emitting layer should just contain the compound represented by Formula (A).
［電子注入層及び電子輸送層］
　電子注入・輸送層は、発光層への電子の注入を助け、発光領域まで輸送する層であって、電子移動度が大きい層であり、式（Ａ）で表わされる化合物は、当該電子注入・輸送層に用いる電子輸送性材料として好適に用いることができる。
　式（Ａ）で表わされる化合物以外の電子輸送性材料としては、分子内にヘテロ原子を１個以上含有する芳香族ヘテロ環化合物が好ましく用いられ、特に含窒素環誘導体が好ましい。また、含窒素環誘導体としては、含窒素６員環もしくは５員環骨格を有する芳香族環、又は含窒素６員環もしくは５員環骨格を有する縮合芳香族環化合物が好ましく、例えば、ピリジン環、ピリミジン環、トリアジン環、ベンズイミダゾール環、フェナントロリン環、キナゾリン環等を骨格に含む化合物が挙げられる。 [Electron injection layer and electron transport layer]
The electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region and has a high electron mobility. The compound represented by the formula (A) includes the electron injection / transport layer. It can be suitably used as an electron transporting material used for the transport layer.
As the electron transporting material other than the compound represented by the formula (A), an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. The nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, such as a pyridine ring. , Pyrimidine ring, triazine ring, benzimidazole ring, phenanthroline ring, quinazoline ring and the like.
　その他、ドナー性材料のドーピング（ｎ）、アクセプター材料のドーピング（ｐ）により、半導体性を備えた有機層を形成してもよい。Ｎドーピングの代表例は、電子輸送性材料にＬｉやＣｓ等の金属をドーピングさせるものであり、Ｐドーピングの代表例は、正孔輸送性材料にＦ４ＴＣＮＱ（2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane）等のアクセプター材をドープするものである（例えば、特許３６９５７１４参照）。 In addition, an organic layer having semiconductivity may be formed by doping a donor material (n) and acceptor material (p). A typical example of N doping is to dope a metal such as Li or Cs into an electron transporting material, and a typical example of P doping is F4TCNQ (2,3,5,6-Tetrafluoro- 7,7,8,8-tetracyanoquinodimethane) and the like (see, for example, Patent 3695714).
　有機ＥＬ素子は発光した光が電極（例えば陰極）により反射するため、直接陽極から取り出される発光と、電極による反射を経由して取り出される発光とが干渉することが知られている。この干渉効果を効率的に利用するため、電子注入・輸送層は数ｎｍ～数μｍの膜厚で適宜選ばれるが、特に膜厚が厚いとき、電圧上昇を避けるために、１０４～１０６Ｖ／ｃｍの電界印加時に電子移動度が少なくとも１０－５ｃｍ２／Ｖｓ以上であることが好ましい。 In the organic EL element, since emitted light is reflected by an electrode (for example, a cathode), it is known that light emitted directly from the anode interferes with light emitted via reflection by the electrode. In order to efficiently use this interference effect, the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several μm. However, particularly when the film thickness is large, in order to avoid a voltage increase, 10 4 to 10 6. The electron mobility is preferably at least 10 −5 cm 2 / Vs or more when an electric field of V / cm is applied.
［発光層］
　式（１）～（４）で表わされる化合物をホストとして１以上含む燐光発光層は、燐光ドーパント（燐光発光性材料）を含有する。
　燐光ドーパントとしては、金属錯体化合物が挙げられ、好ましくはＩｒ，Ｐｔ，Ｏｓ，Ａｕ，Ｃｕ，Ｒｅ及びＲｕから選択される金属原子と、配位子とを有する化合物である。配位子は、オルトメタル結合を有すると好ましい。
　燐光量子収率が高く、発光素子の外部量子効率をより向上させることができるという点で、燐光ドーパントは、Ｉｒ，Ｏｓ及びＰｔから選ばれる金属原子を含有する化合物であると好ましく、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体であるとさらに好ましく、中でもイリジウム錯体及び白金錯体がより好ましく、オルトメタル化イリジウム錯体が最も好ましい。
　ドーパントは、１種単独でも、２種以上の混合物でもよい。 [Light emitting layer]
The phosphorescent layer containing one or more compounds represented by formulas (1) to (4) as a host contains a phosphorescent dopant (phosphorescent material).
Examples of the phosphorescent dopant include metal complex compounds, preferably a compound having a metal atom selected from Ir, Pt, Os, Au, Cu, Re and Ru and a ligand. The ligand preferably has an ortho metal bond.
The phosphorescent dopant is preferably a compound containing a metal atom selected from Ir, Os and Pt in that the phosphorescent quantum yield is high and the external quantum efficiency of the light-emitting element can be further improved, and an iridium complex, It is more preferable that it is a metal complex such as an osmium complex and a platinum complex, among which an iridium complex and a platinum complex are more preferable, and an orthometalated iridium complex is most preferable.
The dopant may be a single type or a mixture of two or more types.
　燐光発光層における燐光ドーパントの添加濃度は特に限定されるものではないが、好ましくは０．１～３０質量％、より好ましくは０．１～２０質量％である The addition concentration of the phosphorescent dopant in the phosphorescent light emitting layer is not particularly limited, but is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass.
　発光層は、ダブルホスト（ホスト・コホストともいう）としてもよい。具体的に、発光層において電子輸送性のホストと正孔輸送性のホストを組み合わせることで、発光層内のキャリアバランスを調整してもよい。
　また、ダブルドーパントとしてもよい。発光層において、量子収率の高いドーパント材料を２種類以上入れることによって、それぞれのドーパントが発光する。例えば、ホストと赤色ドーパント、緑色のドーパントを共蒸着することによって、黄色の発光層を実現することがある。 The light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer.
Moreover, it is good also as a double dopant. In the light emitting layer, each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
　式（１）～（４）で表わされる化合物以外の材料で燐光発光層を形成する場合、燐光発光層の材料として公知の材料が使用できる。具体的には、特願２００５－５１７９３８等を参照すればよい。
　本発明の有機ＥＬ素子は、図２に示す素子のように蛍光発光層を有していてもよい。蛍光発光層としては、公知の材料が使用できる。 When the phosphorescent light emitting layer is formed of a material other than the compounds represented by the formulas (1) to (4), a known material can be used as the material of the phosphorescent light emitting layer. Specifically, Japanese Patent Application No. 2005-517938 may be referred to.
The organic EL device of the present invention may have a fluorescent light emitting layer like the device shown in FIG. A known material can be used for the fluorescent light emitting layer.
　式（１）～（４）で表わされる化合物以外の発光層のホスト材料としては、カルバゾール環、ジベンゾフラン環及びジベンゾチオフェン環のいずれかを含む化合物が好ましい。
　式（１）～（４）で表わされる化合物以外の発光層のホスト材料としては、下記式（ａ）で表わされる化合物が好適に挙げられる。
Figure JPOXMLDOC01-appb-C000042
 （式中、Ｌ１１は、単結合、置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は環形成原子数５～３０のヘテロアリーレン基を表す。
　Ｘ１１は、Ｏ、Ｓ、Ｓｅ又はＴｅを表す。
　Ｒ１４及びＲ１５は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～３０のアリール基、環形成原子数５～３０のヘテロアリール基、置換もしくは無置換の炭素数１～３０のアルキル基、置換もしくは無置換のアルキルシリル基、置換もしくは無置換のアリールシリル基、置換もしくは無置換のヘテロアリールシリル基を表す。
　ｓは、０～３の整数を表す。
　ｔは、０～４の整数を表す。
　Ｃｚは、下記式（ａ―１）又は下記式（ａ―２）で表される基を表す。）
Figure JPOXMLDOC01-appb-C000043
 （式中、＊は、Ｌ１１との結合位置を表す。
　Ｒ１１は、水素原子、置換もしくは無置換の環形成炭素数６～３０のアリール基、環形成原子数５～３０のヘテロアリール基、又は置換もしくは無置換の炭素数１～３０のアルキル基を表す。
　Ｒ１２及びＲ１３は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～３０のアリール基、環形成原子数５～３０のヘテロアリール基、又は置換もしくは無置換の炭素数１～３０のアルキル基を表す。
　ｐ及びｑは、それぞれ独立に、０～４の整数を表す。
　ｒは、０～３の整数を表す。） As the host material of the light emitting layer other than the compounds represented by the formulas (1) to (4), a compound containing any of a carbazole ring, a dibenzofuran ring and a dibenzothiophene ring is preferable.
Preferred examples of the host material for the light emitting layer other than the compounds represented by the formulas (1) to (4) include compounds represented by the following formula (a).
Figure JPOXMLDOC01-appb-C000042
 (Wherein L 11 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a heteroarylene group having 5 to 30 ring atoms.
X 11 represents O, S, Se, or Te.
R 14 and R 15 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted carbon group having 1 to 30 carbon atoms. An alkyl group, a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group, or a substituted or unsubstituted heteroarylsilyl group is represented.
s represents an integer of 0 to 3.
t represents an integer of 0 to 4.
Cz represents a group represented by the following formula (a-1) or the following formula (a-2). )
Figure JPOXMLDOC01-appb-C000043
 (Wherein, * represents a bonding position to L 11.
R 11 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. To express.
R 12 and R 13 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms. Represents an alkyl group.
p and q each independently represents an integer of 0 to 4.
r represents an integer of 0 to 3. )
　式（ａ）のＬ１１の環形成炭素数６～３０のアリーレン基、及び環形成原子数５～３０のヘテロアリーレン基としては、式（１）のＬと同様のものが挙げられる。
　式（ａ）のＲ１１の環形成炭素数６～３０のアリール基、環形成原子数５～３０のヘテロアリール基、及び炭素数１～３０のアルキル基は、式（４）のＲ４０１及びＲａと同様のものが挙げられる。また、Ｒ１１のアルキルシリル基、アリールシリル基及びヘテロアリールシリル基は、それぞれ上記アルキル基、上記アリール基及び上記ヘテロアリール基とシリル基を任意に組み合わせた基である。
　式（ａ）のＲ１２～Ｒ１５の環形成炭素数６～３０のアリール基、環形成原子数５～３０のヘテロアリール基、及び炭素数１～３０のアルキル基は、式（４）のＲａと同様のものが挙げられる。 Examples of the arylene group having 6 to 30 ring carbon atoms and the heteroarylene group having 5 to 30 ring atoms of L 11 in the formula (a) include those similar to L in the formula (1).
The aryl group having 6 to 30 ring carbon atoms, the heteroaryl group having 5 to 30 ring atoms, and the alkyl group having 1 to 30 ring atoms of R 11 in formula (a) are represented by R 401 in formula (4) and The same thing as Ra is mentioned. The alkylsilyl group, arylsilyl group, and heteroarylsilyl group of R 11 are groups obtained by arbitrarily combining the alkyl group, the aryl group, the heteroaryl group, and the silyl group, respectively.
The aryl group having 6 to 30 ring carbon atoms, the heteroaryl group having 5 to 30 ring atoms, and the alkyl group having 1 to 30 carbon atoms of R 12 to R 15 in the formula (a) are represented by the formula (4): The same thing as Ra is mentioned.
　式（ａ）で表わされる化合物の具体例を以下に示す。
　但し、式（ａ）で表わされる化合物は、以下に限定されない。また、以下に示す化合物中、Ｘは酸素原子又は硫黄原子を表し、Ｒ’は水素原子又はメチル基を表す。
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000052
 Specific examples of the compound represented by the formula (a) are shown below.
However, the compound represented by the formula (a) is not limited to the following. In the compounds shown below, X represents an oxygen atom or a sulfur atom, and R ′ represents a hydrogen atom or a methyl group.
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000052
　発光層は単層でもよく、また、積層構造でもよい。発光層を積層させると、発光層界面に電子と正孔を蓄積させることによって再結合領域を発光層界面に集中させることができる。これによって、量子効率を向上させることができる。 The light emitting layer may be a single layer or a laminated structure. When the light emitting layer is stacked, the recombination region can be concentrated on the light emitting layer interface by accumulating electrons and holes at the light emitting layer interface. Thereby, quantum efficiency can be improved.
［阻止層］
　燐光発光層４０に隣接する層に式（１）～（４）で表わされる化合物を使用することも好ましい。例えば、図１の素子の正孔輸送帯域３０と燐光発光層４０の間に、本発明の材料を含有する層（陽極側隣接層）を形成した場合、該層は電子障壁層としての機能や励起子阻止層としての機能を有する。 [Blocking layer]
It is also preferable to use compounds represented by the formulas (1) to (4) in a layer adjacent to the phosphorescent light emitting layer 40. For example, when a layer containing the material of the present invention (an anode side adjacent layer) is formed between the hole transport zone 30 and the phosphorescent light emitting layer 40 of the device of FIG. 1, the layer functions as an electron barrier layer. It functions as an exciton blocking layer.
　燐光発光層４０と電子輸送帯域５０の間に式（１）～（４）で表わされる化合物を含有する層（陰極側隣接層）を形成した場合、該層は正孔障壁層としての機能や励起子阻止層としても機能できる。
　上記障壁層（阻止層）とは、キャリアの移動障壁、又は励起子の拡散障壁の機能を有する層である。発光層から正孔輸送帯域へ電子が漏れることを防ぐための有機層を主に電子障壁層と定義でき、発光層から電子輸送帯域へ正孔が漏れることを防ぐための有機層を正孔障壁層と定義できる。また、発光層で生成された三重項励起子が、三重項エネルギーが発光層よりも低い準位を有する周辺層へ拡散することを防止するための有機層を励起子阻止層（トリプレット障壁層）と定義する場合がある。
　また、式（１）～（４）で表わされる化合物を燐光発光層４０に隣接する層に用い，かつ更にその隣接する層に接合する他の有機薄膜層に用いてもよい。
　加えて、発光層を２層以上形成する場合、式（１）～（４）で表わされる化合物は、発光層間に形成するスペース層材料としても好適に用いることができる。 When a layer containing a compound represented by the formulas (1) to (4) (cathode side adjacent layer) is formed between the phosphorescent light emitting layer 40 and the electron transport zone 50, the layer functions as a hole blocking layer. It can also function as an exciton blocking layer.
The barrier layer (blocking layer) is a layer having a function of a carrier movement barrier or an exciton diffusion barrier. The organic layer for preventing electrons from leaking from the light-emitting layer to the hole transport zone can be defined mainly as an electron barrier layer, and the organic layer for preventing holes from leaking from the light-emitting layer to the electron transport zone is defined as a hole barrier. Can be defined as a layer. In addition, an exciton blocking layer (triplet barrier layer) is an organic layer for preventing triplet excitons generated in the light emitting layer from diffusing into a peripheral layer having triplet energy lower than that of the light emitting layer. May be defined.
Further, the compounds represented by the formulas (1) to (4) may be used in a layer adjacent to the phosphorescent light emitting layer 40 and further used in other organic thin film layers bonded to the adjacent layer.
In addition, when two or more light emitting layers are formed, the compounds represented by the formulas (1) to (4) can be suitably used as a material for the space layer formed between the light emitting layers.
　本発明の有機ＥＬ素子は、陰極と有機薄膜層との界面領域に電子供与性ドーパント及び有機金属錯体の少なくともいずれかを有することも好ましい。
　このような構成によれば、有機ＥＬ素子における発光輝度の向上や長寿命化が図られる。
　また、本発明の有機ＥＬ素子は、電子輸送帯域５０における電子輸送層又は電子注入層に、式（１）～（４）で表わされる化合物と電子供与性ドーパントとを含むことが好ましい。これにより、有機ＥＬ素子の駆動電圧をさらに低減できる。 The organic EL device of the present invention preferably has at least one of an electron donating dopant and an organometallic complex in an interface region between the cathode and the organic thin film layer.
According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
In the organic EL device of the present invention, the electron transport layer or the electron injection layer in the electron transport zone 50 preferably contains a compound represented by formulas (1) to (4) and an electron donating dopant. Thereby, the drive voltage of an organic EL element can further be reduced.
　電子供与性ドーパントとしては、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属化合物、希土類金属、及び希土類金属化合物等から選ばれた少なくとも１種類が挙げられる。
　有機金属錯体としては、アルカリ金属を含む有機金属錯体、アルカリ土類金属を含む有機金属錯体、及び希土類金属を含む有機金属錯体等から選ばれた少なくとも１種類が挙げられる。 Examples of 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.
Examples of 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.
　アルカリ金属としては、リチウム（Ｌｉ）（仕事関数：２．９３ｅＶ）、ナトリウム（Ｎａ）（仕事関数：２．３６ｅＶ）、カリウム（Ｋ）（仕事関数：２．２８ｅＶ）、ルビジウム（Ｒｂ）（仕事関数：２．１６ｅＶ）、セシウム（Ｃｓ）（仕事関数：１．９５ｅＶ）等が挙げられ、仕事関数が２．９ｅＶ以下のものが好ましい。これらのうち好ましくはＫ、Ｒｂ、Ｃｓ、さらに好ましくはＲｂ又はＣｓであり、最も好ましくはＣｓである。 Examples of the alkali metal 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 preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
　アルカリ土類金属としては、カルシウム（Ｃａ）（仕事関数：２．９ｅＶ）、ストロンチウム（Ｓｒ）（仕事関数：２．０ｅＶ以上２．５ｅＶ以下）、バリウム（Ｂａ）（仕事関数：２．５２ｅＶ）等が挙げられ、仕事関数が２．９ｅＶ以下のものが特に好ましい。 Examples of the alkaline earth metal 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.
　希土類金属としては、スカンジウム（Ｓｃ）、イットリウム（Ｙ）、セリウム（Ｃｅ）、テルビウム（Ｔｂ）、イッテルビウム（Ｙｂ）等が挙げられ、仕事関数が２．９ｅＶ以下のものが特に好ましい。 Examples of the rare earth metal 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.
　以上の金属のうち好ましい金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機ＥＬ素子における発光輝度の向上や長寿命化が可能である。 Among these metals, 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.
　アルカリ金属化合物としては、酸化リチウム（Ｌｉ２Ｏ）、酸化セシウム（Ｃｓ２Ｏ）、酸化カリウム（Ｋ２Ｏ）等のアルカリ酸化物、フッ化リチウム（ＬｉＦ）、フッ化ナトリウム（ＮａＦ）、フッ化セシウム（ＣｓＦ）、フッ化カリウム（ＫＦ）等のアルカリハロゲン化物等が挙げられ、フッ化リチウム（ＬｉＦ）、酸化リチウム（Ｌｉ２Ｏ）、フッ化ナトリウム（ＮａＦ）が好ましい。 Examples of the alkali metal compound 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. Examples thereof include 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.
　アルカリ土類金属化合物としては、酸化バリウム（ＢａＯ）、酸化ストロンチウム（ＳｒＯ）、酸化カルシウム（ＣａＯ）及びこれらを混合したストロンチウム酸バリウム（ＢａｘＳｒ１－ｘＯ）（０＜ｘ＜１）、カルシウム酸バリウム（ＢａｘＣａ１－ｘＯ）（０＜ｘ＜１）等が挙げられ、ＢａＯ、ＳｒＯ、ＣａＯが好ましい。 Examples of the alkaline earth metal compound 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.
　希土類金属化合物としては、フッ化イッテルビウム（ＹｂＦ３）、フッ化スカンジウム（ＳｃＦ３）、酸化スカンジウム（ＳｃＯ３）、酸化イットリウム（Ｙ２Ｏ３）、酸化セリウム（Ｃｅ２Ｏ３）、フッ化ガドリニウム（ＧｄＦ３）、フッ化テルビウム（ＴｂＦ３）等が挙げられ、ＹｂＦ３、ＳｃＦ３、ＴｂＦ３が好ましい。 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), include such terbium fluoride (TbF 3) is, YbF 3, ScF 3, TbF 3 are preferable.
　有機金属錯体としては、上記の通り、それぞれ金属イオンとしてアルカリ金属イオン、アルカリ土類金属イオン、希土類金属イオンの少なくとも１つ含有するものであれば特に限定はない。また、配位子にはキノリノール、ベンゾキノリノール、アクリジノール、フェナントリジノール、ヒドロキシフェニルオキサゾール、ヒドロキシフェニルチアゾール、ヒドロキシジアリールオキサジアゾール、ヒドロキシジアリールチアジアゾール、ヒドロキシフェニルピリジン、ヒドロキシフェニルベンゾイミダゾール、ヒドロキシベンゾトリアゾール、ヒドロキシフルボラン、ビピリジル、フェナントロリン、フタロシアニン、ポルフィリン、シクロペンタジエン、β－ジケトン類、アゾメチン類、及びそれらの誘導体等が好ましいが、これらに限定されるものではない。 The organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above. The ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
　電子供与性ドーパント及び有機金属錯体の添加形態としては、界面領域に層状又は島状に形成することが好ましい。形成方法としては、抵抗加熱蒸着法により電子供与性ドーパント及び有機金属錯体の少なくともいずれかを蒸着しながら、界面領域を形成する発光材料や電子注入材料である有機物を同時に蒸着させ、有機物中に電子供与性ドーパント及び有機金属錯体の少なくともいずれかを分散する方法が好ましい。分散濃度は通常、モル比で有機物：電子供与性ドーパント及び／又は有機金属錯体＝１００：１～１：１００であり、好ましくは５：１～１：５である。 As the addition form of the electron donating dopant and the organometallic complex, it is preferable to form a layer or an island in the interface region. As a forming method, while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material. A method of dispersing at least one of the donor dopant and the organometallic complex is preferable. The dispersion concentration is usually organic substance: electron donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.
　電子供与性ドーパント及び有機金属錯体の少なくともいずれかを層状に形成する場合は、界面の有機層である発光材料や電子注入材料を層状に形成した後に、電子供与性ドーパント及び有機金属錯体の少なくともいずれかを単独で抵抗加熱蒸着法により蒸着し、好ましくは層の厚み０．１ｎｍ以上１５ｎｍ以下で形成する。 In the case where at least one of the electron donating dopant and the organometallic complex is formed in a layered form, after forming the light emitting material or the electron injecting material that is the organic layer at the interface in a layered form, at least one of the electron donating dopant and the organometallic complex is formed. These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
　電子供与性ドーパント及び有機金属錯体の少なくともいずれかを島状に形成する場合は、界面の有機層である発光材料や電子注入材料を島状に形成した後に、電子供与性ドーパント及び有機金属錯体の少なくともいずれかを単独で抵抗加熱蒸着法により蒸着し、好ましくは島の厚み０．０５ｎｍ以上１ｎｍ以下で形成する。 In the case where at least one of an electron donating dopant and an organometallic complex is formed in an island shape, a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
　また、本発明の有機ＥＬ素子における、主成分と、電子供与性ドーパント及び有機金属錯体の少なくともいずれかの割合としては、モル比で、主成分：電子供与性ドーパント及び／又は有機金属錯体＝５：１～１：５であると好ましく、２：１～１：２であるとさらに好ましい。 In the organic EL device of the present invention, the ratio of at least one of the main component and the electron donating dopant and the organometallic complex is, as a molar ratio, the main component: the electron donating dopant and / or the organometallic complex = 5. It is preferably 1 to 1: 5, and more preferably 2: 1 to 1: 2.
［正孔注入層及び正孔輸送層（正孔注入・輸送層）］
　正孔注入・輸送層は、発光層への正孔注入を助け、発光領域まで輸送する層であって、正孔移動度が大きく、イオン化エネルギーが通常５．６ｅＶ以下と小さい層である。
　また、ｐ型Ｓｉ、ｐ型ＳｉＣ等の無機化合物も正孔注入材料として使用することができる。 [Hole injection layer and hole transport layer (hole injection / transport layer)]
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.
［基板］
　基板としてはガラス板、ポリマー板等を用いることができる。
　ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等が挙げられる。また、ポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルフォン、ポリサルフォン等を挙げることができる。 [substrate]
As the substrate, a glass plate, a polymer plate or the like can be used.
Examples of the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.
［陽極］
　陽極は例えば導電性材料からなり、４ｅＶより大きな仕事関数を有する導電性材料が適している。
　上記導電性材料としては、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等及びそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板に使用される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂が挙げられる。
　陽極は、必要があれば２層以上の層構成により形成されていてもよい。 [anode]
The anode is made of, for example, a conductive material, and a conductive material having a work function larger than 4 eV is suitable.
Examples of the conductive material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and their alloys, ITO substrate, tin oxide used for NESA substrate, indium oxide, and the like. Examples thereof include metal oxides and organic conductive resins such as polythiophene and polypyrrole.
The anode may be formed with a layer structure of two or more layers if necessary.
［陰極］
　陰極は例えば導電性材料からなり、４ｅＶより小さな仕事関数を有する導電性材料が適している。
　上記導電性材料としては、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン、アルミニウム、フッ化リチウム等及びこれらの合金が挙げられるが、これらに限定されるものではない。
　また、上記合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウム等が代表例として挙げられるが、これらに限定されるものではない。合金の比率は、蒸着源の温度、雰囲気、真空度等により制御され、適切な比率に選択される。
　陰極は、必要があれば２層以上の層構成により形成されていてもよく、陰極は上記導電性材料を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。 [cathode]
The cathode is made of, for example, a conductive material, and a conductive material having a work function smaller than 4 eV is suitable.
Examples of the conductive material include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof.
Examples of the alloy 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 cathode may be formed with a layer structure of two or more layers, and the cathode can be produced by forming a thin film from the conductive material by a method such as vapor deposition or sputtering.
　発光層からの発光を陰極から取り出す場合、陰極の発光に対する透過率は１０％より大きくすることが好ましい。
　また、陰極としてのシート抵抗は数百Ω／□以下が好ましく、膜厚は通常１０ｎｍ～１μｍであり、好ましくは５０～２００ｎｍである。 When light emitted from the light emitting layer is taken out from the cathode, the transmittance of the cathode for light emission is preferably greater than 10%.
The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 nm.
　本発明の有機ＥＬ素子の各層の形成は、真空蒸着、スパッタリング、プラズマ、イオンプレーティング等の乾式成膜法やスピンコーティング、ディッピング、フローコーティング等の湿式成膜法等の公知の方法を適用することができる。 For the formation of each layer of the organic EL device of the present invention, a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
　各層の膜厚は特に限定されるものではないが、適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要になり効率が悪くなる。膜厚が薄すぎるとピンホール等が発生して、電界を印加しても充分な発光輝度が得られない。通常の膜厚は５ｎｍ～１０μｍの範囲が適しているが、１０ｎｍ～０．２μｍの範囲がさらに好ましい。 The film thickness of each layer 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 μm, but more preferably in the range of 10 nm to 0.2 μm.
合成例１（化合物６の合成）
（１）中間体Ａの合成
Figure JPOXMLDOC01-appb-C000053
 　アルゴン雰囲気下、２－ニトロアニリン３５．０ｇ（２５３ｍｍｏｌ）、１－ブロモ－３－ヨードベンゼン８６．１ｇ（３０４ｍｍｏｌ）、ヨウ化銅４．８ｇ（２５．３ｍｍｏｌ）、ｔｒａｎｓ－１，２－ジアミノシクロヘキサン５．８ｇ（５０．６ｍｍｏｌ）、リン酸三カリウム１１８．２ｇ（５５７ｍｍｏｌ）を脱水１，４－ジオキサン４００ｍｌに加えて、９０℃で２０時間加熱撹拌した。反応溶液に水を加えて析出した固体を集め、この固体を水及びメタノールで洗浄することにより中間体Ａ７１．１ｇ（収率９５％）を得た。 Synthesis Example 1 (Synthesis of Compound 6)
(1) Synthesis of intermediate A
Figure JPOXMLDOC01-appb-C000053
 Under an argon atmosphere, 35.0 g (253 mmol) of 2-nitroaniline, 86.1 g (304 mmol) of 1-bromo-3-iodobenzene, 4.8 g (25.3 mmol) of copper iodide, trans-1,2-diaminocyclohexane 5.8 g (50.6 mmol) and tripotassium phosphate 118.2 g (557 mmol) were added to 400 ml of dehydrated 1,4-dioxane, and the mixture was heated and stirred at 90 ° C. for 20 hours. Water was added to the reaction solution, and the precipitated solid was collected, and this solid was washed with water and methanol to obtain 71.1 g of Intermediate A (yield 95%).
（２）中間体Ｂの合成
Figure JPOXMLDOC01-appb-C000054
 　アルゴン雰囲気下、中間体Ａ７１．１ｇ（２４２ｍｍｏｌ）、テトラヒドロフラン２８０ｍｌ、メタノール６０ｍｌを加えた反応溶液に、水３００ｍｌに溶解したハイドロサルファイトナトリウム８４．３ｇ（４８４ｍｍｏｌ）を室温で１時間かけて滴下装入した。２時間撹拌した後、さらにハイドロサルファイトナトリウム４２．１ｇ（２４２ｍｍｏｌ）を加え、２４時間撹拌した。有機相を分取し、水相に酢酸エチルと炭酸水素ナトリウム水溶液を加え、有機相を分取して合わせた。この有機相をシリカゲルカラムクロマトグラフィーで精製することにより、中間体Ｂ３０．２ｇ（収率４７％）を得た。シリカゲルカラムクロマトグラフィーの展開溶媒は、ヘプタンのみ、ヘプタン：トルエン＝１：１の溶媒、トルエン：酢酸エチル＝１０：１の溶媒をこの順に用いた。 (2) Synthesis of intermediate B
Figure JPOXMLDOC01-appb-C000054
 Under an argon atmosphere, 84.3 g (484 mmol) of hydrosulfite sodium dissolved in 300 ml of water was added dropwise at room temperature over 1 hour to a reaction solution in which 71.1 g (242 mmol) of intermediate A, 280 ml of tetrahydrofuran and 60 ml of methanol were added. did. After stirring for 2 hours, 42.1 g (242 mmol) of hydrosulfite sodium was further added and stirred for 24 hours. The organic phase was separated, ethyl acetate and aqueous sodium hydrogen carbonate solution were added to the aqueous phase, and the organic phase was separated and combined. This organic phase was purified by silica gel column chromatography to obtain 30.2 g of intermediate B (yield 47%). As developing solvents for silica gel column chromatography, heptane alone, heptane: toluene = 1: 1 solvent, and toluene: ethyl acetate = 10: 1 solvent were used in this order.
（３）中間体Ｃの合成
Figure JPOXMLDOC01-appb-C000055
 　アルゴン雰囲気下、中間体Ｂ３０．２ｇ（１１５ｍｍｏｌ）をＮ－メチルピロリドン（ＮＭＰ）１７０ｍｌに加えた反応溶液に、プロピオニルクロリド１１．７ｇ（１２６ｍｍｏｌ）を１０～１５℃で滴下装入し、室温で１時間撹拌した。水２００ｍｌを加えて析出した固体を集め、水で洗浄することにより中間体Ｃ３９．４ｇを得た。これ以上の精製はせずに、次の工程に用いた。 (3) Synthesis of intermediate C
Figure JPOXMLDOC01-appb-C000055
 Under an argon atmosphere, 11.7 g (126 mmol) of propionyl chloride was added dropwise at 10 to 15 ° C. to a reaction solution in which 30.2 g (115 mmol) of the intermediate B was added to 170 ml of N-methylpyrrolidone (NMP). Stir for hours. 200 ml of water was added and the precipitated solid was collected and washed with water to obtain 39.4 g of Intermediate C. It was used in the next step without further purification.
（４）中間体Ｄの合成
Figure JPOXMLDOC01-appb-C000056
 　アルゴン雰囲気下、中間体Ｃ３９．４ｇ、ｐ－トルエンスルホン酸水和物６．５ｇ（３４．２ｍｍｏｌ）、キシレン３００ｍｌを加え、Ｄｅａｎ－Ｓｔａｒｋ管を取り付けた反応容器で生成する水を除去しながら、１４０℃で２時間加熱撹拌した。室温に戻した後、水３Ｌを加えて分液し、有機相を減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：トルエン）で精製し、さらにトルエン溶媒で再結晶を繰り返すことにより、中間体Ｄ２５．５ｇ（中間体Ｂからの収率：７４％）を得た。 (4) Synthesis of intermediate D
Figure JPOXMLDOC01-appb-C000056
 Under an argon atmosphere, intermediate C39.4 g, p-toluenesulfonic acid hydrate 6.5 g (34.2 mmol) and xylene 300 ml were added, and water generated in a reaction vessel equipped with a Dean-Stark tube was removed. The mixture was heated and stirred at 140 ° C. for 2 hours. After returning to room temperature, 3 L of water was added for liquid separation, and the organic phase was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene), and further recrystallized with a toluene solvent to obtain 25.5 g of intermediate D (yield from intermediate B: 74%). .
（５）化合物６の合成
Figure JPOXMLDOC01-appb-C000057
 　アルゴン雰囲気下、中間体Ｄ３．０ｇ（１０ｍｍｏｌ）、中間体Ｅ（例えば、ＵＳ２０１３／０８２５９１公報に記載の方法で合成できる。）４．５ｇ（１０ｍｍｏｌ）、Ｐｄ（ＰＰｈ３）４０．２３ｇ（０．２ｍｍｏｌ）、２Ｍ炭酸ナトリウム水溶液１０ｍｌを１，２－ジメトキシエタン（ＤＭＥ）５０ｍｌに加え、還流条件下で加熱撹拌した。メタノールを加えて析出した固体を集め、ジクロロメタンに溶かした油状物をシリカゲルカラムクロマトグラフィーで精製することにより、化合物６　４．３ｇ（収率６８％）を得た。シリカゲルカラムクロマトグラフィーの展開溶媒は、ヘキサン：ジクロロメタン＝１０：１の溶媒、ヘキサン：ジクロロメタン＝３：１の溶媒をこの順に用いた。
　ＦＤ－ＭＳ分析の結果、分子量６２８に対してｍ／ｅ＝６２８であった。 (5) Synthesis of compound 6
Figure JPOXMLDOC01-appb-C000057
 Under an argon atmosphere, Intermediate D 3.0 g (10 mmol), Intermediate E (for example, synthesized by the method described in US2013 / 082591) 4.5 g (10 mmol), Pd (PPh 3 ) 4 0.23 g (0 0.2 mmol), 10 ml of 2M aqueous sodium carbonate solution was added to 50 ml of 1,2-dimethoxyethane (DME), and the mixture was heated and stirred under reflux conditions. Methanol was added and the precipitated solid was collected, and the oil dissolved in dichloromethane was purified by silica gel column chromatography to obtain 4.3 g of Compound 6 (yield 68%). As developing solvents for silica gel column chromatography, a solvent of hexane: dichloromethane = 10: 1 and a solvent of hexane: dichloromethane = 3: 1 were used in this order.
As a result of FD-MS analysis, it was m / e = 628 with respect to the molecular weight 628.
合成例２（化合物８の合成）
（１）中間体Ｇの合成
Figure JPOXMLDOC01-appb-C000058
 　アルゴン雰囲気下、Ｐｄ（ｄｂａ）２４．９５ｇ（８．６ｍｍｏｌ）、トリシクロヘキシルホスフィン５．８ｇ（２１ｍｍｏｌ）を１，４－ジオキサン１．５Ｌに加え、次いで、ビス（ピナコラート）ジボロン８０．２ｇ（３１６ｍｍｏｌ）、酢酸カリウム４２．２ｇ（４２０ｍｍｏｌ）、中間体Ｆ１００ｇ（２８６ｍｍｏｌ）を順に室温で反応溶液に装入した。中間体Ｆは、合成例１（３）においてプロピオニルクロリドの代わりに塩化ベンゾイルを用いた以外は、合成例１（１）～（４）と同様の方法で合成した。
　装入後、還流条件下で８時間加熱撹拌し、室温に戻した後、トルエンと水を加えて、有機相を分取した。有機相を中性になるまで炭酸水素ナトリウム水溶液で洗浄し、溶媒を減圧下で留去した。得られた固体をヘプタンで洗浄することにより、中間体Ｇ９１ｇ（収率８０％）を得た。 Synthesis Example 2 (Synthesis of Compound 8)
(1) Synthesis of intermediate G
Figure JPOXMLDOC01-appb-C000058
 Under an argon atmosphere, 4.95 g (8.6 mmol) of Pd (dba) 2 and 5.8 g (21 mmol) of tricyclohexylphosphine were added to 1.5 L of 1,4-dioxane, and then 80.2 g of bis (pinacolato) diboron ( 316 mmol), 42.2 g (420 mmol) of potassium acetate, and 100 g (286 mmol) of intermediate F were sequentially charged to the reaction solution at room temperature. Intermediate F was synthesized in the same manner as in Synthesis Examples 1 (1) to (4) except that benzoyl chloride was used instead of propionyl chloride in Synthesis Example 1 (3).
After charging, the mixture was heated and stirred for 8 hours under reflux conditions, and after returning to room temperature, toluene and water were added to separate the organic phase. The organic phase was washed with an aqueous sodium bicarbonate solution until neutral, and the solvent was distilled off under reduced pressure. The obtained solid was washed with heptane to obtain 91 g of intermediate G (yield 80%).
（２）中間体Ｉの合成
Figure JPOXMLDOC01-appb-C000059
 　アルゴン雰囲気下、中間体Ｇ４．０ｇ（１０ｍｍｏｌ）、中間体Ｈ（例えば、Ｔｅｔｒａｈｅｄｒｏｎ　Ｌｅｔｔｅｒｓ、６９４２～６９４７ページ（２０１１年）に記載の方法で合成できる。）４．０ｇ（１０ｍｍｏｌ）、Ｐｄ（ＰＰｈ３）４０．２３ｇ（０．２ｍｍｏｌ）、２Ｍ炭酸ナトリウム水溶液１０ｍｌを１，２－ジメトキシエタン（ＤＭＥ）５０ｍｌに加え、還流条件下で加熱撹拌した。メタノールを加えて析出した固体を集め、ジクロロメタンに溶かした油状物をシリカゲルカラムクロマトグラフィーで精製することにより、中間体Ｉ１．６ｇ（収率２７％）を得た。シリカゲルカラムクロマトグラフィーの展開溶媒は、ヘキサン：ジクロロメタン＝１０：１の溶媒、ヘキサン：ジクロロメタン＝３：１の溶媒をこの順に用いた。 (2) Synthesis of intermediate I
Figure JPOXMLDOC01-appb-C000059
 Under an argon atmosphere, Intermediate G 4.0 g (10 mmol), Intermediate H (for example, can be synthesized by the method described in Tetrahedron Letters, pages 6942-6947 (2011)) 4.0 g (10 mmol), Pd (PPh 3 4 ) 0.23 g (0.2 mmol), 2M aqueous sodium carbonate solution (10 ml) was added to 1,2-dimethoxyethane (DME) (50 ml), and the mixture was heated and stirred under reflux conditions. Methanol was added and the precipitated solid was collected, and the oil dissolved in dichloromethane was purified by silica gel column chromatography to obtain 1.6 g of intermediate I (yield 27%). As developing solvents for silica gel column chromatography, a solvent of hexane: dichloromethane = 10: 1 and a solvent of hexane: dichloromethane = 3: 1 were used in this order.
（３）化合物８の合成
Figure JPOXMLDOC01-appb-C000060
 　アルゴン雰囲気下、中間体Ｉ１．６g（２．７ｍｍｏｌ）、ジベンゾフラン－２－ボロン酸０．５７ｇ（２．７ｍｍｏｌ）、Ｐｄ（ＰＰｈ３）４９４ｍｇ（０．０８１ｍｍｏｌ）、２Ｍ炭酸ナトリウム水溶液５ｍｌを１，２－ジメトキシエタン（ＤＭＥ）２０ｍｌに加え、還流条件下で加熱撹拌した。メタノールを加えて析出した固体を集め、ジクロロメタンに溶かした油状物をシリカゲルカラムクロマトグラフィーで精製することにより、化合物８　１．５ｇ（収率８２％）を得た。シリカゲルカラムクロマトグラフィーの展開溶媒は、ヘキサン：ジクロロメタン＝１０：１の溶媒、ヘキサン：ジクロロメタン＝３：１の溶媒をこの順に用いた。
　ＦＤ－ＭＳ分析の結果、分子量６７７に対してｍ／ｅ＝６７７であった。 (3) Synthesis of Compound 8
Figure JPOXMLDOC01-appb-C000060
 Under an argon atmosphere, 1.6 g (2.7 mmol) of the intermediate I, 0.57 g (2.7 mmol) of dibenzofuran-2-boronic acid, 94 mg (0.081 mmol) of Pd (PPh 3 ) 4, 5 ml of 2M aqueous sodium carbonate solution , 2-Dimethoxyethane (DME) in 20 ml and stirred under reflux. Methanol was added, and the precipitated solid was collected, and an oily substance dissolved in dichloromethane was purified by silica gel column chromatography to obtain 1.5 g of Compound 8 (yield 82%). As developing solvents for silica gel column chromatography, a solvent of hexane: dichloromethane = 10: 1 and a solvent of hexane: dichloromethane = 3: 1 were used in this order.
As a result of FD-MS analysis, m / e = 677 relative to molecular weight 677.
合成例３（化合物９の合成）
Figure JPOXMLDOC01-appb-C000061
 　合成例２（３）のジベンゾフラン－２－ボロン酸の代わりに、中間体Ｊ（例えば、ＷＯ２０１３－０３８６５０公報に記載の方法で合成できる。）を用いた以外は、合成例２（３）と同様の方法で、化合物９を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６７８に対してｍ／ｅ＝６７８であった。 Synthesis Example 3 (Synthesis of Compound 9)
Figure JPOXMLDOC01-appb-C000061
 Similar to Synthesis Example 2 (3) except that Intermediate J (for example, synthesized by the method described in WO2013-038650) was used instead of dibenzofuran-2-boronic acid in Synthesis Example 2 (3). Compound 9 was synthesized by this method.
As a result of FD-MS analysis, it was m / e = 678 with respect to the molecular weight 678.
合成例４（化合物１３の合成）
　合成例１（３）において、プロピオニルクロリドの代わりにｎ－ブチリルクロリドを用いた以外は、合成例１（１）～（５）と同様の方法で化合物１３を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６４２に対してｍ／ｅ＝６４２であった。 Synthesis Example 4 (Synthesis of Compound 13)
Compound 13 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5) except that n-butyryl chloride was used in place of propionyl chloride in Synthesis Example 1 (3).
As a result of FD-MS analysis, it was m / e = 642 with respect to the molecular weight 642.
合成例５（化合物１５の合成）
　合成例１（３）において、プロピオニルクロリドの代わりにイソブチリルクロリドを用いた以外は、合成例１（１）～（５）と同様の方法で化合物１５を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６４２に対してｍ／ｅ＝６４２であった。 Synthesis Example 5 (Synthesis of Compound 15)
Compound 15 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5) except that in Example 1 (3), isobutyryl chloride was used instead of propionyl chloride.
As a result of FD-MS analysis, it was m / e = 642 with respect to the molecular weight 642.
合成例６（化合物２０の合成）
　合成例１（３）において、プロピオニルクロリドの代わりにピバロイルクロリドを用いた以外は、合成例１（１）～（５）と同様の方法で化合物２０を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６５６に対してｍ／ｅ＝６５６であった。 Synthesis Example 6 (Synthesis of Compound 20)
Compound 20 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5) except that pivaloyl chloride was used instead of propionyl chloride in Synthesis Example 1 (3).
As a result of FD-MS analysis, m / e = 656 with respect to the molecular weight of 656.
合成例７（化合物２１の合成）
　合成例１（３）において、プロピオニルクロリドの代わりに２－メチルブチリルクロリドを用いた以外は、合成例１（１）～（５）と同様の方法で化合物２１を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６５６に対してｍ／ｅ＝６５６であった。 Synthesis Example 7 (Synthesis of Compound 21)
Compound 21 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5) except that 2-methylbutyryl chloride was used in place of propionyl chloride in Synthesis Example 1 (3).
As a result of FD-MS analysis, m / e = 656 with respect to the molecular weight of 656.
合成例８（化合物５の合成）
Figure JPOXMLDOC01-appb-C000062
 　合成例１（５）において、中間体Ｅの代わりに、中間体Ｋ（例えば、ＥＰ２４７１７７２公報に記載の方法で合成できる。）を用いた以外は、合成例１（５）と同様の方法で化合物５を合成した。
　ＦＤ－ＭＳ分析の結果、分子量５３９に対してｍ／ｅ＝５３９であった。 Synthesis Example 8 (Synthesis of Compound 5)
Figure JPOXMLDOC01-appb-C000062
 In Synthesis Example 1 (5), the compound was prepared in the same manner as in Synthesis Example 1 (5), except that Intermediate K (for example, synthesized by the method described in EP2477172) was used instead of Intermediate E. 5 was synthesized.
As a result of FD-MS analysis, it was m / e = 539 with respect to the molecular weight of 539.
合成例９（化合物３の合成）
　合成例２（２）において、中間体Ｈの代わりに８－（ジベンゾフラン－２－イル）ジベンゾフラン－２－ボロン酸（例えば、ＷＯ２０１３－０３８６５０公報に記載の方法で合成できる。）を用いた以外は、合成例２（２）と同様の方法で化合物３を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６０２に対してｍ／ｅ＝６０２であった。 Synthesis Example 9 (Synthesis of Compound 3)
In Synthesis Example 2 (2), 8- (dibenzofuran-2-yl) dibenzofuran-2-boronic acid (for example, synthesized by the method described in WO2013-038650) was used in place of Intermediate H. Compound 3 was synthesized in the same manner as in Synthesis Example 2 (2).
As a result of FD-MS analysis, m / e = 602 with respect to molecular weight 602.
合成例１０（化合物４の合成）
　合成例１（１）において、１－ブロモ－３－ヨードベンゼンの代わりに１－ブロモ－４－ヨードベンゼンを、合成例１（３）において、プロピオニルクロリドの代わりにｎ－ブチリルクロリドを用いた以外は、合成例１（１）～（５）と同様の方法で化合物４を合成した。
　ＦＤ－ＭＳ分析の結果、分子量６４２に対してｍ／ｅ＝６４２であった。 Synthesis Example 10 (Synthesis of Compound 4)
In Synthesis Example 1 (1), 1-bromo-4-iodobenzene was used instead of 1-bromo-3-iodobenzene, and in Synthesis Example 1 (3), n-butyryl chloride was used instead of propionyl chloride. Except for the above, compound 4 was synthesized in the same manner as in Synthesis Examples 1 (1) to (5).
As a result of FD-MS analysis, it was m / e = 642 with respect to the molecular weight 642.
実施例１
　２５ｍｍ×７５ｍｍ×１．１ｍｍのＩＴＯ透明電極付きガラス基板（ジオマティック社製）に、イソプロピルアルコール中での５分間の超音波洗浄を施し、さらに、３０分間のＵＶ（Ｕｌｔｒａｖｉｏｌｅｔ）オゾン洗浄を施した。
　このようにして洗浄した透明電極付きガラス基板を、真空蒸着装置の基板ホルダーに装着し、まず、ガラス基板の透明電極ラインが形成されている側の面上に、透明電極を覆うようにして、ＨＴＭ１を厚さ２０ｎｍで蒸着し、正孔注入層を得た。次いで、この膜上に、ＨＴＭ２を厚さ６０ｎｍで蒸着し、正孔輸送層を得た。
　この正孔輸送層上に、燐光ホスト材料としてＨ－１と燐光発光材料であるＤ－１とを厚さ５０ｎｍで共蒸着し、燐光発光層を得た。燐光発光層内におけるＨ－１の濃度は８０質量％、Ｄ－１の濃度は２０質量％であった。
　続いて、この燐光発光層上に化合物１を厚さ１０ｎｍで蒸着し、第１電子輸送層を得た。さらに、ＥＴＭ１を厚さ１０ｎｍで蒸着して第２電子輸送層を得た後、厚さ１ｎｍのＬｉＦ、厚さ８０ｎｍの金属Ａｌを順次積層し、陰極を得た。尚、電子注入性電極であるＬｉＦについては、１Å／ｍｉｎの速度で形成した。 Example 1
A 25 mm × 75 mm × 1.1 mm glass substrate with an ITO transparent electrode (manufactured by Geomatic) was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and further subjected to UV (Ultraviolet) ozone cleaning for 30 minutes. .
The glass substrate with the transparent electrode thus cleaned is attached to the substrate holder of the vacuum evaporation apparatus, and first, on the surface of the glass substrate on which the transparent electrode line is formed, the transparent electrode is covered, HTM1 was deposited with a thickness of 20 nm to obtain a hole injection layer. Subsequently, HTM2 was vapor-deposited with a thickness of 60 nm on this film to obtain a hole transport layer.
On this hole transport layer, H-1 as a phosphorescent host material and D-1 as a phosphorescent material were co-evaporated at a thickness of 50 nm to obtain a phosphorescent layer. The concentration of H-1 in the phosphorescent light emitting layer was 80% by mass, and the concentration of D-1 was 20% by mass.
Subsequently, Compound 1 was deposited on the phosphorescent light emitting layer with a thickness of 10 nm to obtain a first electron transporting layer. Furthermore, after depositing ETM1 with a thickness of 10 nm to obtain a second electron transporting layer, 1 nm thick LiF and 80 nm thick metal Al were sequentially laminated to obtain a cathode. Note that LiF, which is an electron injecting electrode, was formed at a rate of 1 Å / min.
　実施例で使用した化合物は、以下の通りである。
Figure JPOXMLDOC01-appb-C000063
 The compounds used in the examples are as follows.
Figure JPOXMLDOC01-appb-C000063
［有機ＥＬ素子の発光性能評価］
　作製した有機ＥＬ素子を直流電流駆動により発光させ、輝度、電流密度を測定し、電流密度１ｍＡ／ｃｍ２における電圧及び発光効率（外部量子効率）を求めた。さらに初期輝度３，０００ｃｄ／ｍ２における輝度７０％寿命（輝度が７０％まで低下する時間）を求めた。これら発光性能の評価結果を表１に示す。 [Light-emitting performance evaluation of organic EL elements]
The produced organic EL element was caused to emit light by direct current drive, and the luminance and current density were measured, and the voltage and luminous efficiency (external quantum efficiency) at a current density of 1 mA / cm 2 were determined. Furthermore, the brightness | luminance 70% lifetime (time when a brightness | luminance falls to 70%) in initial stage brightness | luminance 3,000cd / m < 2 > was calculated | required. The evaluation results of these light emitting performances are shown in Table 1.
実施例２
　第２電子輸送層の材料としてＥＴＭ１の代わりに化合物１を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。 Example 2
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound 1 was used instead of ETM1 as the material for the second electron transport layer. The results are shown in Table 1.
実施例３
　第１電子輸送層の材料として化合物１の代わりに下記化合物２を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000064
 Example 3
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the following compound 2 was used instead of compound 1 as a material for the first electron transport layer. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000064
実施例４
　第１電子輸送層の材料として化合物１の代わりに化合物２を用い、第２電子輸送層の材料としてＥＴＭ１の代わりに化合物２を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。 Example 4
An organic EL device was produced in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 as the material for the first electron transport layer, and Compound 2 was used instead of ETM1 as the material for the second electron transport layer. And evaluated. The results are shown in Table 1.
実施例５
　燐光ホスト材料としてＨ－１の代わりに下記化合物Ｈ－２を用い、第１電子輸送層の材料として化合物１の代わりに化合物２を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000065
 Example 5
An organic EL device was prepared in the same manner as in Example 1, except that the following compound H-2 was used instead of H-1 as the phosphorescent host material, and compound 2 was used instead of compound 1 as the material of the first electron transport layer. Prepared and evaluated. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000065
実施例６
　燐光ホスト材料としてＨ－１の代わりに下記化合物Ｈ－３を用い、第１電子輸送層の材料として化合物１の代わりに化合物２を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000066
 Example 6
An organic EL device was prepared in the same manner as in Example 1 except that the following compound H-3 was used instead of H-1 as the phosphorescent host material, and compound 2 was used instead of compound 1 as the material for the first electron transport layer. Prepared and evaluated. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000066
比較例１
　第１電子輸送層の材料として化合物１の代わりに化合物Ａを用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000067
 Comparative Example 1
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound A was used instead of Compound 1 as the material for the first electron transport layer. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000067
比較例２
　第１電子輸送層の材料として化合物１の代わりに化合物Ｂを用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000068
 Comparative Example 2
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound B was used instead of Compound 1 as the material for the first electron transport layer. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000068
比較例３
　燐光ホスト材料としてＨ－１の代わりに下記Ｈ－Ａを用い、第１電子輸送層の材料として化合物１の代わりに化合物２を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表１に示す。
Figure JPOXMLDOC01-appb-C000069
 Comparative Example 3
An organic EL device was produced in the same manner as in Example 1 except that the following HA was used in place of H-1 as the phosphorescent host material, and compound 2 was used in place of compound 1 as the material for the first electron transport layer. And evaluated. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　また、実施例及び比較例で使用したホスト材料及び第１電子輸送層材料の三重項エネルギーを測定した。結果を表２に示す。 In addition, the triplet energy of the host material and the first electron transport layer material used in Examples and Comparative Examples was measured. The results are shown in Table 2.
　尚、三重項エネルギー（ＥＴ（ｅＶ））は、下記方法で評価した。
　まず、試料をＥＰＡ溶媒（ジエチルエーテル：イソペンタン：エタノール＝５：５：２（容積比））に１０μｍｏｌ／Ｌで溶解させ、燐光測定用試料とした。この燐光測定用試料を石英セルに入れ、温度７７Ｋで励起光を照射し、放射される燐光スペクトルを測定した。これを基に換算式ＥＴ（ｅＶ）＝１２３９．８５／λｅｄｇｅによって求めた値を三重項エネルギーと定義した。上記「λｅｄｇｅ」とは、縦軸に燐光強度、横軸に波長をとって、燐光スペクトルを表したときに、燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸の交点の波長値（単位：ｎｍ）を意味する。
　燐光スペクトルの測定には、（株）日立ハイテクノロジー製のＦ－４５００型分光蛍光光度計本体と低温測定用オプション部品を用いた。 Triplet energy (E T (eV)) was evaluated by the following method.
First, a sample was dissolved in an EPA solvent (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) at 10 μmol / L to obtain a sample for phosphorescence measurement. This phosphorescence measurement sample was placed in a quartz cell, irradiated with excitation light at a temperature of 77 K, and the emitted phosphorescence spectrum was measured. Based on this, a value obtained by the conversion formula E T (eV) = 1239.85 / λ edge was defined as triplet energy. The above-mentioned “λ edge ” means that when the phosphorescence spectrum is represented by taking the phosphorescence intensity on the vertical axis and the wavelength on the horizontal axis, the tangent line is drawn with respect to the rising edge on the short wavelength side of the phosphorescence spectrum. Means the wavelength value (unit: nm) of the intersection.
For the measurement of the phosphorescence spectrum, an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. and an optional component for low temperature measurement were used.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
　表１及び２の結果より、実施例の素子は、比較例の素子より低電圧、高効率かつ長寿命化する素子が得られることが分かった。特に、低電圧化、高効率化の効果は大きいことが分かる。これは、高い三重項エネルギーを有するベンズイミダゾール化合物を電子輸送層材料として用いて、さらに、カルバゾール環とジベンゾフラン環（もしくはジベンゾチオフェン環）を同一骨格に持ち、高い三重項エネルギーを有するホスト材料を適切に組み合わせたことによる効果によるものである。即ち、青色燐光発光に必要な高い三重項エネルギーを素子内に閉じ込め、かつ、素子内のキャリアバランスを適切に整えたためである。 From the results of Tables 1 and 2, it was found that the device of the example can obtain a device having a lower voltage, higher efficiency, and longer life than the device of the comparative example. In particular, it can be seen that the effect of lowering the voltage and increasing the efficiency is great. This is because a benzimidazole compound having a high triplet energy is used as an electron transport layer material, and a host material having a carbazole ring and a dibenzofuran ring (or dibenzothiophene ring) in the same skeleton and having a high triplet energy is suitable. This is due to the effect of the combination. That is, the high triplet energy necessary for blue phosphorescence emission is confined in the device and the carrier balance in the device is appropriately adjusted.
実施例７～２５
　第１電子輸送層の材料として化合物１の代わりに化合物３～化合物２１を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表３に示す。 Examples 7-25
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that compounds 3 to 21 were used in place of compound 1 as the material for the first electron transport layer. The results are shown in Table 3.
実施例２６～２９
　燐光ホスト材料として、Ｈ－１の代わりにＨ－２を用い、第１電子輸送層の材料として化合物１の代わりにそれぞれ化合物４、６、９、１９を用いた以外は、実施例１と同様にして有機ＥＬ素子を作製し、評価した。結果を表３に示す。 Examples 26-29
As in Example 1, except that H-2 was used as the phosphorescent host material instead of H-1, and compounds 4, 6, 9, and 19 were used instead of compound 1 as the material for the first electron transport layer, respectively. Thus, an organic EL device was produced and evaluated. The results are shown in Table 3.
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　また、実施例７～２９で使用した第１電子輸送層材料の三重項エネルギーを上記と同様にして測定した。結果を表４に示す。 Further, the triplet energy of the first electron transport layer material used in Examples 7 to 29 was measured in the same manner as described above. The results are shown in Table 4.
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
　表３及び表４の結果より、実施例の素子は、低電圧、高効率かつ長寿命化する素子が得られることが分かった。特に、低電圧化、高効率化の効果は大きいことが分かる。これは、高い三重項エネルギーを有するベンズイミダゾール化合物を電子輸送層材料として用いて、さらに、カルバゾール環とジベンゾフラン環（もしくはジベンゾチオフェン環）を同一骨格に持ち、高い三重項エネルギーを有するホスト材料を適切に組み合わせたことによる効果によるものである。即ち、青色燐光発光に必要な高い三重項エネルギーを素子内に閉じ込め、かつ、素子内のキャリアバランスを適切に整えたためである。 From the results of Tables 3 and 4, it was found that the device of the example can obtain a device with low voltage, high efficiency and long life. In particular, it can be seen that the effect of lowering the voltage and increasing the efficiency is great. This is because a benzimidazole compound having a high triplet energy is used as an electron transport layer material, and a host material having a carbazole ring and a dibenzofuran ring (or dibenzothiophene ring) in the same skeleton and having a high triplet energy is suitable. This is due to the effect of the combination. That is, the high triplet energy necessary for blue phosphorescence emission is confined in the device and the carrier balance in the device is appropriately adjusted.
　本発明の有機ＥＬ素子は、壁掛けテレビのフラットパネルディスプレイ等の平面発光体、複写機、プリンター、液晶ディスプレイのバックライト又は計器類等の光源、表示板、標識灯、照明等に利用できる。 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 an instrument, a display board, a marker lamp, and an illumination.
　上記に本発明の実施形態及び／又は実施例を幾つか詳細に説明したが、当業者は、本発明の新規な教示及び効果から実質的に離れることなく、これら例示である実施形態及び／又は実施例に多くの変更を加えることが容易である。従って、これらの多くの変更は本発明の範囲に含まれる。
　本願のパリ優先の基礎となる日本出願明細書の内容を全てここに援用する。 Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will appreciate that these exemplary embodiments and / or embodiments are substantially without departing from the novel teachings and advantages of the present invention. It is easy to make many changes to the embodiment. Accordingly, many of these modifications are within the scope of the present invention.
All the contents of the Japanese application specification that is the basis of the priority of Paris in this application are incorporated herein.

Claims (13)

  1. 　陽極と陰極との間に、発光層を含む２層以上の有機薄膜層を有し、
    　前記発光層が、下記式（１）で表わされる化合物を少なくとも１つ以上含み、
    　前記発光層の陰極側で発光層と接する有機薄膜層が下記式（Ａ）で表わされるベンズイミダゾール化合物を少なくとも１つ以上含む、
    　有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000072
     （式（１）中、
    　Ｇ１～Ｇ６は、それぞれ独立に、Ｃ－Ｒ１又は窒素原子である。
    　Ｇ１１～Ｇ１８は、それぞれ独立に、Ｃ－Ｒ２又は窒素原子である。
    　Ｒ及びＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールオキシ基、置換もしくは無置換の環形成炭素数６～１８のアリールチオ基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールチオ基、置換もしくは無置換の環形成炭素数６～１８のアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロアリールスルホニル基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換のフルオロアルキル基、置換もしくは無置換のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ１が存在するとき、複数のＲ１は、互いに同一又は異なっていてもよい。
    　但し、Ｇ２及び／又はＧ５がＣ－Ｒ１である場合は、Ｇ２及びＧ５のＲ１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
    　Ｒ２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ２が存在するときは、それぞれのＲ２は同一又は異なっていてもよい。
    　Ｒ、Ｒ１、Ｒ２が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　Ｘは、酸素原子又は硫黄原子を表す。）
    Figure JPOXMLDOC01-appb-C000073
     （式（Ａ）中、Ｒａ～Ｒｄ、Ｒｅ～Ｒｆ、Ｒｈ～Ｒｉ、Ｒｊ～Ｒｋ及びＲｍ～Ｒｎは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　Ｒｇ及びＲｌは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、又は置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基である。
    　但し、Ｒｅ～Ｒｆ、Ｒｈ～Ｒｉ、Ｒｊ～Ｒｋ及びＲｍ～Ｒｎの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、又は置換もしくは無置換のジベンゾチオフェニル基である。
    　Ａｒ１は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
    　Ａｒ２は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
    　Ｒａ～Ｒｎ、Ａｒ１及びＡｒ２が置換基を有する場合の当該置換基Ｒ’’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　ｍ及びｎは、それぞれ０又は１である。
    　ｏ及びｐは、それぞれ０～３の整数である。
    　但し、ｍ、ｎ、ｏ及びｐは、ｍ＋ｏ≧１及びｎ＋ｐ≧１を満たす。
    　ｏが２又は３である場合、複数のＡｒ１は互いに同じでも異なってもよい。
    　ｐが２又は３である場合、複数のＡｒ２は互いに同じでも異なってもよい。）     Having two or more organic thin film layers including a light emitting layer between the anode and the cathode;
    The light emitting layer contains at least one compound represented by the following formula (1),
    The organic thin film layer in contact with the light emitting layer on the cathode side of the light emitting layer contains at least one benzimidazole compound represented by the following formula (A),
    Organic electroluminescence device.
    Figure JPOXMLDOC01-appb-C000072
     (In the formula (1),
    G 1 to G 6 are each independently C—R 1 or a nitrogen atom.
    G 11 to G 18 are each independently C—R 2 or a nitrogen atom.
    R and R 1 are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 18 ring atoms, substituted or unsubstituted arylthio group having 6 to 18 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 18 ring atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted ring atom number 5-18 heteroarylsulfonyl group, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted fluoroalkyl group, substituted or An unsubstituted fluoroalkoxy group or a cyano group.
    When a plurality of CR 1 are present, the plurality of R 1 may be the same as or different from each other.
    However, if G 2 and / or G 5 is a C-R 1, R 1 of G 2 and G 5 are each independently 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
    Each R 2 independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
    When a plurality of C—R 2 are present, each R 2 may be the same or different.
    When R, R 1 and R 2 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms. Alkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, and 5 to 18 ring atoms. A heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
    X represents an oxygen atom or a sulfur atom. )
    Figure JPOXMLDOC01-appb-C000073
     (In the formula (A), Ra to Rd, Re to Rf, Rh to Ri, Rj to Rk and Rm to Rn are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted group. Or an unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted Substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms A cyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 1 to 2 It is a fluoroalkoxy group or a cyano group.
    Rg and Rl are each independently 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 ring carbon atoms, a substituted or unsubstituted carbon number, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
    Provided that at least one of Re to Rf, Rh to Ri, Rj to Rk, and Rm to Rn is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or A substituted or unsubstituted dibenzothiophenyl group;
    Ar 1 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or metaphenylene group, a substituted or unsubstituted metabiphenylyl group or metabiphenylylene group. Substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,6-pyridylene group Group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted or unsubstituted 2-dibenzothiophenyl Group or 2,8-dibenzothiophenylene group, or substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
    Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group. Metabiphenylyl group or metabiphenylylene group, substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
    When Ra to Rn, Ar 1 and Ar 2 have a substituent, the substituent R ″ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number. An alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, and the number of ring atoms A heteroaromatic cyclic group having 5 to 18 carbon atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
    m and n are each 0 or 1.
    o and p are each an integer of 0 to 3.
    However, m, n, o, and p satisfy m + o ≧ 1 and n + p ≧ 1.
    When o is 2 or 3, the plurality of Ar 1 may be the same as or different from each other.
    When p is 2 or 3, the plurality of Ar 2 may be the same as or different from each other. )
  2. 　前記式（１）で表わされる化合物が、下記式（２ａ）で表わされる化合物、下記式（２ｂ）で表わされる化合物、又は下記式（２ｃ）で表わされる化合物である請求項１に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000074
     （式（２ａ）～（２ｃ）中、
    　Ｇ２１１～Ｇ２１４は、それぞれ独立に、Ｃ－Ｒ２１又は窒素原子である。
    　Ｇ２２１～Ｇ２２８は、それぞれ独立に、Ｃ－Ｒ２２又は窒素原子である。
    　Ｇａ～Ｇｋはそれぞれ独立に、Ｃ－Ｒ２３又は窒素原子である。
    　Ｒ２１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ２１が存在する場合、複数のＲ２１は、それぞれ同一又は異なっていてもよい。
    　Ｒ２２は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ２２が存在する場合、複数のＲ２２は、それぞれ同一又は異なっていてもよい。
    　Ｒ２３は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ２３が存在する場合、複数のＲ２３は、それぞれ同一又は異なっていてもよい。
    　Ｒ２１、Ｒ２２及びＲ２３が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　Ｘ１は、酸素原子、又は硫黄原子である。
    　Ｘ２は、酸素原子、硫黄原子、又は＝Ｃ（ＣＨ３）２である。）     The organic compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (2a), a compound represented by the following formula (2b), or a compound represented by the following formula (2c). Electroluminescence element.
    Figure JPOXMLDOC01-appb-C000074
     (In the formulas (2a) to (2c),
    G 211 to G 214 are each independently C—R 21 or a nitrogen atom.
    G 221 to G 228 are each independently C—R 22 or a nitrogen atom.
    Ga to Gk are each independently C—R 23 or a nitrogen atom.
    R 21 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
    When a plurality of C—R 21 are present, the plurality of R 21 may be the same or different from each other.
    R 22 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
    When a plurality of C—R 22 are present, the plurality of R 22 may be the same or different from each other.
    R 23 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
    When a plurality of C—R 23 are present, the plurality of R 23 may be the same or different from each other.
    When R 21 , R 22 and R 23 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms An 18 heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
    X 1 is an oxygen atom or a sulfur atom.
    X 2 is an oxygen atom, a sulfur atom, or ═C (CH 3 ) 2 . )
  3. 　前記式（１）で表わされる化合物が、下記式（３ａ）で表わされる化合物、下記式（３ｂ）で表わされる化合物、又は下記式（３ｃ）で表わされる化合物である請求項１に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000075
     （式（３ａ）～式（３ｃ）中、
    　Ｙは、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成原子数５～７の単環ヘテロ芳香族環基、又は下記式（３－１）で表される基である。
    　Ｇ３１１～Ｇ３１７、Ｇ３２１～Ｇ３２７、及びＧ３３１～Ｇ３３７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子である。
    　Ｒ３１は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ３１が存在するときは、複数のＲ３１は、それぞれ同一又は異なっていてもよい。
    　Ｌ３は、単結合、酸素原子を含む２価の連結基、ケイ素原子を含む２価の連結基、硫黄原子を含む２価の連結基、炭素数１～５のアルキレン基、環形成炭素数３～６のシクロアルキレン基、環形成炭素数６～１８の芳香族炭化水素環基、又は環形成原子数５～１８のヘテロ芳香族環基である。
    　Ｒ３１が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、フルオロアルキル基、フルオロアルコキシ基又はシアノ基である。
    　Ｘ３は、酸素原子又は硫黄原子である。）
    Figure JPOXMLDOC01-appb-C000076
     （式（３－１）中、
    　＊は、窒素原子との結合を示す。
    　Ｇ３４１～Ｇ３４７は、それぞれ独立に、Ｃ－Ｒ３１又は窒素原子であり、Ｒ３１は式（３ａ）～式（３ｃ）のＲ３１と同じである。
    　Ｘ３１は、置換基を有する窒素原子、酸素原子又は硫黄原子である。）     The organic compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (3a), a compound represented by the following formula (3b), or a compound represented by the following formula (3c). Electroluminescence element.
    Figure JPOXMLDOC01-appb-C000075
     (In the formulas (3a) to (3c),
    Y represents a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monocyclic heteroaromatic ring group having 5 to 7 ring atoms, or the following formula (3- It is group represented by 1).
    G 311 to G 317 , G 321 to G 327 , and G 331 to G 337 are each independently C—R 31 or a nitrogen atom.
    R 31 each independently represents 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 ring carbon atoms, a substituted or unsubstituted carbon number of 1; Alkoxy group having ˜20, substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, substituted or unsubstituted silyl group, fluorine atom, substituted or unsubstituted carbon atoms of 1 to 20 Or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms or a cyano group.
    When a plurality of C—R 31 are present, the plurality of R 31 may be the same or different from each other.
    L 3 is a single bond, a divalent linking group containing an oxygen atom, a divalent linking group containing a silicon atom, a divalent linking group containing a sulfur atom, an alkylene group having 1 to 5 carbon atoms, or the number of ring-forming carbon atoms. A cycloalkylene group having 3 to 6 carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a heteroaromatic ring group having 5 to 18 ring atoms.
    When R 31 has a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a ring Cycloalkoxy group having 3 to 20 carbon atoms, aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, aryloxy group having 6 to 18 ring carbon atoms, heteroaromatic ring having 5 to 18 ring atoms Group, silyl group, fluorine atom, fluoroalkyl group, fluoroalkoxy group or cyano group.
    X 3 is an oxygen atom or a sulfur atom. )
    Figure JPOXMLDOC01-appb-C000076
     (In the formula (3-1),
    * Indicates a bond with a nitrogen atom.
    G 341 ~ G 347 are each independently C-R 31 or a nitrogen atom, R 31 is the same as R 31 in the formula (3a) ~ formula (3c).
    X 31 is a nitrogen atom, oxygen atom or sulfur atom having a substituent. )
  4. 　前記式（１）で表わされる化合物が、下記式（４）で表わされる化合物である請求項１に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000077
     （式（４）中、
    　Ｒ４１、Ｒ４２及びＲ４３は、それぞれ独立に、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、又は置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基である。
    　Ｒ４１、Ｒ４２及びＲ４３は、互いに直接結合して環を形成してもよいし、酸素原子を介して結合して環を形成してもよいし、硫黄原子を介して結合して環を形成してもよいし、又はケイ素原子を介して結合して環を形成してもよい。
    　Ｇ４１～Ｇ４４は、それぞれ独立に、Ｃ－Ｒ４４又は窒素原子である。
    　Ｒ４４は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ４４が存在する場合、複数のＲ４４は、それぞれ同一又は異なっていてもよい。
    　Ｇ４１１～Ｇ４１８は、それぞれ独立に、Ｃ－Ｒ４５又は窒素原子である。
    　Ｒ４５は、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　複数のＣ－Ｒ４５が存在する場合、複数のＲ４５は、それぞれ同一又は異なっていてもよい。
    　Ｒ４１、Ｒ４２、Ｒ４３、Ｒ４４及びＲ４５が置換基を有する場合の当該置換基Ｒ’は、水素原子、炭素数１～２０のアルキル基、環形成炭素数３～２０のシクロアルキル基、炭素数１～２０のアルコキシ基、環形成炭素数３～２０のシクロアルコキシ基、環形成炭素数６～１８の芳香族炭化水素環基、環形成炭素数６～１８のアリールオキシ基、環形成原子数５～１８のヘテロ芳香族環基、シリル基、フッ素原子、炭素数１～２０のフルオロアルキル基、炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　Ｘ４は、酸素原子又は硫黄原子である。）     The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (4).
    Figure JPOXMLDOC01-appb-C000077
     (In formula (4),
    R 41 , R 42 and R 43 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted group. It is an aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms.
    R 41 , R 42 and R 43 may be directly bonded to each other to form a ring, may be bonded through an oxygen atom to form a ring, or may be bonded through a sulfur atom to form a ring. Or may be bonded via a silicon atom to form a ring.
    G 41 to G 44 each independently represents C—R 44 or a nitrogen atom.
    R 44 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
    When a plurality of C—R 44 are present, the plurality of R 44 may be the same or different from each other.
    G 411 to G 418 are each independently C—R 45 or a nitrogen atom.
    R 45 represents 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 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 18 carbon atoms An aryloxy group, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted C1-C20 fluoroalkoxy group or cyano group.
    When a plurality of C—R 45 are present, the plurality of R 45 may be the same or different from each other.
    When R 41 , R 42 , R 43 , R 44 and R 45 have a substituent, the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 20 ring carbon atoms. A group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ring carbon atoms, an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, A heteroaromatic cyclic group having 5 to 18 ring atoms, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
    X 4 is an oxygen atom or a sulfur atom. )
  5. 　前記式（Ａ）のＲｆ、Ｒｈ、Ｒｋ及びＲｍの少なくとも１つが、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基である請求項１～４のいずれかに記載の有機エレクトロルミネッセンス素子。 In the formula (A), at least one of Rf, Rh, Rk and Rm is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted 2-dibenzofuranyl group, substituted or unsubstituted The organic electroluminescence device according to claim 1, which is a 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group.
  6. 　前記式（Ａ）のＲｆ及びＲｈの両方、又は前記式（Ａ）のＲｋ及びＲｍの両方が、それぞれ置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換の２－ジベンゾフラニル基、置換もしくは無置換の４－ジベンゾフラニル基、置換もしくは無置換の２－ジベンゾチオフェニル基、又は置換もしくは無置換の４－ジベンゾチオフェニル基である請求項１～５のいずれかに記載の有機エレクトロルミネッセンス素子。 Both Rf and Rh in the formula (A), or both Rk and Rm in the formula (A) are substituted or unsubstituted carbazolyl groups, substituted or unsubstituted azacarbazolyl groups, substituted or unsubstituted 2- 6. A dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group. An organic electroluminescence device according to any one of the above.
  7. 　前記式（Ａ）のＡｒ１が、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基である請求項１～６のいずれかに記載の有機エレクトロルミネッセンス素子。 Ar 1 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted 2-dibenzo group. The organic electroluminescence according to any one of claims 1 to 6, which is a furanyl group or a 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or a 2,8-dibenzothiophenylene group. element.
  8. 　前記式（Ａ）のＡｒ２が、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、又は置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基である請求項１～７のいずれかに記載の有機エレクトロルミネッセンス素子。 Ar 2 in the formula (A) is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group. A substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, or a substituted or unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothiophenylene group; An organic electroluminescence device according to any one of the above.
  9. 　前記発光層が燐光発光材料を含み、
    　前記燐光発光材料が、イリジウム（Ｉｒ）、オスミウム（Ｏｓ）及び白金（Ｐｔ）から選択される１種以上の金属原子のオルトメタル化錯体である請求項１～８のいずれかに記載の有機エレクトロルミネッセンス素子。     The light emitting layer includes a phosphorescent material;
    The organic electrophoretic material according to any one of claims 1 to 8, wherein the phosphorescent material is an orthometalated complex of one or more metal atoms selected from iridium (Ir), osmium (Os), and platinum (Pt). Luminescence element.
  10. 　前記陰極と前記有機薄膜層との界面領域が電子供与性ドーパントを含む請求項１～９のいずれかに記載の有機エレクトロルミネッセンス素子。 10. The organic electroluminescence device according to claim 1, wherein an interface region between the cathode and the organic thin film layer contains an electron donating dopant.
  11. 　下記式（ａ）で表される化合物。
    Figure JPOXMLDOC01-appb-C000078
     （式（ａ）中、Ｒは、置換もしくは無置換の炭素数１～２０のアルキル基、又は置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基である。
    　Ｒａ～Ｒｄ、及びＲｊ～Ｒｎは、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１～２０のアルキル基、置換もしくは無置換の環形成炭素数３～２０のシクロアルキル基、置換もしくは無置換の炭素数１～２０のアルコキシ基、置換もしくは無置換の環形成炭素数３～２０のシクロアルコキシ基、置換もしくは無置換の環形成炭素数６～１８の芳香族炭化水素環基、置換もしくは無置換の環形成炭素数６～１８のアリールオキシ基、置換もしくは無置換の環形成原子数５～１８のヘテロ芳香族環基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基、フッ素原子、置換もしくは無置換の炭素数１～２０のフルオロアルキル基、置換もしくは無置換の炭素数１～２０のフルオロアルコキシ基又はシアノ基である。
    　但し、Ｒｍ及びＲｋの少なくとも１つは、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基である。
    　Ａｒ２は、単結合、置換もしくは無置換の炭素数１～２０のアルキル基もしくはアルキレン基、置換もしくは無置換のフェニル基もしくはメタフェニレン基、置換もしくは無置換のパラフェニレン基、置換もしくは無置換のメタビフェニリル基もしくはメタビフェニリレン基、置換もしくは無置換のメタターフェニリル基もしくはメタターフェニリレン基、置換もしくは無置換の３－ピリジル基もしくは３，５－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，６－ピリジレン基、置換もしくは無置換の２－ピリジル基もしくは２，４－ピリジレン基、置換もしくは無置換の２－ジベンゾフラニル基もしくは２，８－ジベンゾフラニレン基、置換もしくは無置換の２－ジベンゾチオフェニル基もしくは２，８－ジベンゾチオフェニレン基、又は置換もしくは無置換の３－カルバゾリル基もしくは３，６－カルバゾリレン基である。
    　ｎは、０又は１である。
    　ｐは、０又は１である。
    　ｎ＋ｐ≧１である。）     A compound represented by the following formula (a).
    Figure JPOXMLDOC01-appb-C000078
     (In the formula (a), R represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
    Ra to Rd and Rj to Rn are each independently 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 ring carbon atoms, substituted or unsubstituted, Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group; A fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
    However, at least one of Rm and Rk is a substituted or unsubstituted carbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted A substituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group.
    Ar 2 is a single bond, a substituted or unsubstituted alkyl group or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group or a metaphenylene group, a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted group. Metabiphenylyl group or metabiphenylylene group, substituted or unsubstituted metaterphenylyl group or metaterphenylylene group, substituted or unsubstituted 3-pyridyl group or 3,5-pyridylene group, substituted or unsubstituted 2 -Pyridyl group or 2,6-pyridylene group, substituted or unsubstituted 2-pyridyl group or 2,4-pyridylene group, substituted or unsubstituted 2-dibenzofuranyl group or 2,8-dibenzofuranylene group, substituted Or an unsubstituted 2-dibenzothiophenyl group or 2,8-dibenzothio A phenylene group, or a substituted or unsubstituted 3-carbazolyl group or 3,6-carbazolylene group.
    n is 0 or 1.
    p is 0 or 1.
    n + p ≧ 1. )
  12. 　前記式（ａ）において、Ｒｍ及びＲｋの両方が、それぞれ独立して、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のアザカルバゾリル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のアザジベンゾフラニル基、又は置換もしくは無置換のアザジベンゾチオフェニル基である請求項１１に記載の化合物。 In the formula (a), each of Rm and Rk independently represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted group. The compound according to claim 11, which is a dibenzothiophenyl group, a substituted or unsubstituted azadibenzofuranyl group, or a substituted or unsubstituted azadibenzothiophenyl group.
  13. 　前記式（ａ）において、Ｒｍ及びＲｋの少なくとも１つが、置換もしくは無置換のカルバゾリル基である請求項１１に記載の化合物。 The compound according to claim 11, wherein in the formula (a), at least one of Rm and Rk is a substituted or unsubstituted carbazolyl group.
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