WO2014017094A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique 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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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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    • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un élément électroluminescent organique qui possède au moins deux couches minces organiques contenant des couches luminescentes, entre une anode et une cathode. Lesdites couches luminescentes contiennent au moins un composé représenté par la formule (1). Les couches minces organiques connectant les couches luminescentes côté cathode de ces dernières, contiennent au moins un composé benzimidazole représenté par la formule (A).
PCT/JP2013/004523 2012-07-25 2013-07-25 Élément électroluminescent organique WO2014017094A1 (fr)

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CN106753340A (zh) * 2016-12-20 2017-05-31 中节能万润股份有限公司 一种苯并咪唑类有机电致发光材料及其制备方法和应用
CN106941133A (zh) * 2017-03-16 2017-07-11 武汉华星光电技术有限公司 一种有机发光器件及其制备方法
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CN104362261A (zh) * 2014-10-23 2015-02-18 上海道亦化工科技有限公司 一种基于磷光发光主体材料的有机电致发光器件
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CN105349137B (zh) * 2015-12-14 2017-07-11 陕西师范大学 具有双极载流子传输性能的电致发光材料及作为有机电致发光器件主体材料的应用
CN105968041A (zh) * 2016-07-22 2016-09-28 吉林奥来德光电材料股份有限公司 联苯基双咔唑类化合物及其制备方法和由该化合物制成的有机发光器件
CN105968041B (zh) * 2016-07-22 2019-03-22 吉林奥来德光电材料股份有限公司 联苯基双咔唑类化合物及其制备方法和由该化合物制成的有机发光器件
CN106753340A (zh) * 2016-12-20 2017-05-31 中节能万润股份有限公司 一种苯并咪唑类有机电致发光材料及其制备方法和应用
CN106941133A (zh) * 2017-03-16 2017-07-11 武汉华星光电技术有限公司 一种有机发光器件及其制备方法
US10825994B2 (en) 2017-03-16 2020-11-03 Wuhan China Star Optoelectronics Technology, Ltd. Organic light emitting device and preparation method thereof
US11795185B2 (en) 2017-12-13 2023-10-24 Lg Display Co., Ltd. Compound for electron-transport material and organic light emitting diode including the same

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