WO2006043440A1 - Organic electroluminescent device, display and illuminating device - Google Patents

Organic electroluminescent device, display and illuminating device Download PDF

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Publication number
WO2006043440A1
WO2006043440A1 PCT/JP2005/018672 JP2005018672W WO2006043440A1 WO 2006043440 A1 WO2006043440 A1 WO 2006043440A1 JP 2005018672 W JP2005018672 W JP 2005018672W WO 2006043440 A1 WO2006043440 A1 WO 2006043440A1
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general formula
represented
formula
organic
chemical
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PCT/JP2005/018672
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French (fr)
Japanese (ja)
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Shuichi Sugita
Hiroshi Kita
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Konica Minolta Holdings, Inc.
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Priority to JP2006542331A priority Critical patent/JP5309446B2/en
Publication of WO2006043440A1 publication Critical patent/WO2006043440A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • Organic electoluminescence device display device and lighting device
  • the present invention relates to an organic electoluminescence element, a display device, and a lighting device.
  • ELD electoric luminescence display
  • organic EL devices organic electroluminescence devices
  • Inorganic electoluminescent elements have been used as planar light sources, but an AC high voltage is required to drive the light emitting elements.
  • an organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. By injecting electrons and holes into the light emitting layer and recombining them, excitons are obtained.
  • This is an element that emits light by using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts.
  • fluorescence 'phosphorescence emission of light
  • it since it is a self-luminous type, it has a wide viewing angle, and since it is a thin-film type complete solid-state device with high visibility, it is attracting attention from the viewpoints of space saving and portability.
  • organic EL devices that emit light efficiently and with high brightness with lower power consumption are desired.
  • stilbene derivatives distyryl Technology that improves light emission luminance and extends device lifetime by doping a small amount of phosphor into an arylene derivative or tristyrylarylene derivative
  • 8-hydroxyquinoline aluminum complex A compound having an organic light-emitting layer doped with a trace amount of a phosphor (see, for example, Patent Document 2), 8-hydroxyquinoline aluminum complex as a host compound, and a quinacridone dye
  • a device having an organic light emitting layer doped with see, for example, Patent Document 3 is known.
  • Non-Patent Document 4 various electron transport materials are used as a host of phosphorescent compounds, and these are doped with a novel iridium complex (for example, see Non-Patent Document 4). Furthermore, high luminous efficiency is obtained by introducing a hole block layer (see, for example, Non-Patent Document 5).
  • Patent Document 1 Patent No. 3093796
  • Patent Document 2 Japanese Patent Laid-Open No. 63-264692
  • Patent Document 3 JP-A-3-255190
  • Patent Document 4 U.S. Patent No. 6,097,147
  • Patent Document 5 Japanese Patent Laid-Open No. 4-297076
  • Patent Document 6 Japanese Patent Laid-Open No. 2001-244079
  • Patent Document 7 International Publication No. 04Z074399 Pamphlet
  • Patent Document 8 Japanese Unexamined Patent Publication No. 2000-196140
  • Non-patent literature 1 MA Baldo et al., Nature, 395 ⁇ , 151–154 (1998)
  • Non-patent literature 2 MA Baldo et al., Nature, 403 ⁇ , 17, 750–753 (200 0) Year)
  • Non-Patent Document 3 S. Lamansky et al., J. Am. Chem. Soc., 123 ⁇ , 4304 (2 001)
  • Non-Patent Document 4 M. E. Tompson et al., The 10th Internatioternational Workshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu)
  • Non-Patent Document 5 Moon— Jae Youn. 0g, Tetsuo Tsutsuiet al., The 10th International Workshop on Inorganic and Organic Electroluminescence (EL, 00, Hamamatsu)
  • Non-Patent Document 6 Ikai et al, The 10th International Workshop on Inorga nic and Organic Electroluminescence (EL 5 00, Hamamatsu)
  • An object of the present invention is to provide an organic EL element, a lighting device, and a display device having a structure with excellent electro-optical characteristics, which has a low emission voltage due to a low resistance of the organic layer and a high luminous efficiency. Is to provide.
  • one embodiment of the present invention is an organic electoluminescence device having at least a light emitting layer between a cathode and an anode, and at least one layer of the following general formula ( An organic electrification device comprising a hole transport layer containing at least one compound represented by 1) and containing a hole transport material and an acceptor compound.
  • Z represents an aromatic heterocycle
  • Z represents an aromatic heterocycle or an aromatic hydrocarbon ring
  • Z represents a divalent linking group or a simple bond.
  • R represents a hydrogen atom or a substituent.
  • FIG. 1 is a schematic diagram showing an example of a display device that also has organic EL element force.
  • FIG. 2 is a schematic diagram of display unit A.
  • FIG. 3 is an equivalent circuit diagram of a drive circuit constituting a pixel.
  • FIG. 4 is a schematic diagram of a passive matrix display device.
  • FIG. 5 is a schematic view of a lighting device including an organic EL element.
  • An organic electoluminescence device having at least a light-emitting layer between a cathode and an anode, and at least one layer contains at least one compound represented by the following general formula (1)
  • an organic electroluminescence device having a hole transporting layer containing a hole transporting material and an acceptor compound.
  • Z represents an aromatic heterocycle
  • Z represents an aromatic heterocycle or an aromatic hydrocarbon ring
  • Z represents a divalent linking group or a simple bond.
  • R represents a hydrogen atom or a substituent.
  • An organic electoluminescence device having at least a light emitting layer between a cathode and an anode, and at least one layer contains at least one compound represented by the following general formula (1)
  • an organic electroluminescence device having an electron transport layer containing an electron transport material and a donor compound.
  • Z represents an aromatic heterocyclic ring
  • Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
  • Z represents a divalent linking group or a simple bond.
  • R represents a hydrogen atom or a substituent.
  • the (3) The organic electoluminescence device according to (1), further comprising an electron transport layer containing an electron transport material and a donor compound.
  • the organic electoluminescence device according to item 1 of ⁇ (3), displacement force.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 3 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent. Further, a plurality of R may be the same or different from each other.
  • the compound represented by the general formula (1) has at least one group represented by any one of the following general formulas (2-1) to (2-10):
  • R, R, R ⁇ : R and R-R each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 are each independently a hydrogen atom or a substituent having a small force R 1 to R 2)
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 2
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 5
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 2
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but na and nb are 6.
  • R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
  • At least one of the basic forces represented by the general formulas (2-1) to (2-10) is selected. Represents one group. )
  • 681 and 688 are each independently a force representing a hydrogen atom or a substituent R
  • At least one of 681 688 represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • At least one of R 1 to R 4 is a group represented by the general formula (2-1) to (2-10).
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • o and p each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
  • o and p each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
  • the acceptor compound is Au, Pt, W, Ir, POC1, AsF, CI, Br, I, TC
  • a display device comprising the organic electoluminescence device according to (40).
  • An illuminating device comprising the organic electoluminescence device according to (40).
  • a display device comprising the illumination device according to (42) and a liquid crystal element as display means.
  • the present invention relates to an organic electoluminescence having at least a light emitting layer between a cathode and an anode.
  • the organic electoluminescence element contains at least one compound represented by the general formula (1) in at least one layer, and contains a positive hole transport material and an acceptor compound. It is characterized by having a hole transport layer or having an electron transport layer containing an electron transport material and a donor compound, and further having both.
  • acceptor compounds include Au, Pt, W, Ir, POC1, AsF, CI, Br, and I.
  • TCNQ (7, 7, 8, 8—tetracyanoquinodimethane
  • TCNQF4 tetrafluorotetracyanodimethane
  • TCNE tetracyanoethylene
  • HCNB hexacia nobutagen
  • Compounds having a cyano group such as DDQ (dicyclodisianobenzoquinone), compounds having a -tro group such as TNF (tri-trofluorenone), DNF (dinitrofluorenone), organics such as fluoranil, chlorael and bromale Materials.
  • compounds having a cyano group such as TCNQ, TCNQF4, TCNE, HCNB, and DDQ are more preferred.
  • the addition ratio of the acceptor compound to the hole transport material is preferably 1 to 20% by mass.
  • Examples of donor compounds include those of the periodic table as alkali metals and alkaline earth metals, and examples of salts thereof include carboxylates (acetates, etc.), sulfonates (methanesulfonates). , Tosylates, etc.), halides (fluorides, chlorides, bromides and iodides), hydroxides, carbonates, nitrates and sulfates. Of these, a cesium salt is more preferred.
  • the addition ratio of the donor compound to the electron transporting material is preferably 1 to 20% by mass.
  • the compound represented by the general formula (1) according to the present invention is used as a constituent component of a constituent layer of an organic EL element described later.
  • the light emitting layer or the hole blocking layer it is particularly preferable that it is contained in the hole blocking layer.
  • the compound according to the present invention may be used in other constituent layers of the organic EL device, if necessary.
  • Z represents an aromatic heterocyclic ring which may have a substituent
  • Z represents a substituent
  • 1 2 represents an aromatic heterocycle or an aromatic hydrocarbon ring which may have a substituent, and Z represents a divalent linkage.
  • R represents a hydrogen atom or a substituent.
  • Aromatic heterocycles represented by Z and Z include furan ring, thiophene ring, pyridine ring,
  • the aromatic hydrocarbon ring represented by Z includes a benzene ring, a biphenyl ring, and a naphthalene ring.
  • the aromatic hydrocarbon ring is represented by R described later.
  • Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).
  • cycloalkyl group for example, cyclopentyl group, cyclohexyl group, etc.
  • Alkenyl group for example, buyl group, allyl group, etc.
  • alkynyl group for example, ethynyl group, propargyl group, etc.
  • aryl group for example,
  • aromatic heterocyclic group e.g. furyl group, chael group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, triazinyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, quinazolyl group, phthalazinyl group, etc.
  • heterocyclic group eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.
  • alkoxy group eg, methoxy group, ethoxy group, propyloxy group
  • cycloalkoxyl group eg, cyclopentyloxy group, cyclohexyloxy group etc.
  • Cyclopentylamino groups 2-ethylhexylamino groups, dodecylamino groups, a-lino groups, naphthylamino groups, 2-pyridylamino groups, etc., halogen atoms (eg fluorine atoms, chlorine atoms, bromine atoms, etc.), fluorinated hydrocarbons Group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyan group, nitro group, hydroxyl group, mercapto group, silyl group (for example, trimethylsilyl group, Triisopropylpropyl silyl group, triphenyl silyl group, phenyljetyl silyl group, etc.).
  • substituents may be further substituted with the above substituents!
  • a plurality of these substituents may be bonded to each other to form a ring.
  • the substituent is an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, or an aromatic heterocyclic group.
  • divalent linking group examples include hydrocarbon groups such as alkylene, alkene, alkylene, and arylene, and those that contain a heteroatom or thiophene 2, 5 diyl group. It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a pyrazine 2,3 diyl group (also referred to as a heteroaromatic compound), or it may be a force lucogen atom such as oxygen or sulfur. There may be. Further, it may be a group that joins heteroatoms such as an alkylimino group, a dialkylsilane diyl group, or a diarylgermandyl group.
  • hydrocarbon groups such as alkylene, alkene, alkylene, and arylene, and those that contain a heteroatom or thiophene 2, 5 diyl group. It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a pyrazine 2,3 diyl group (also referred to as a heteroar
  • the simple bond is a bond that directly bonds the substituents to be linked.
  • the Z-membered ring represented by the general formula (1) is preferable. This
  • the luminous efficiency can be further increased. Further, the life can be extended.
  • a z-membered ring is preferable. This increases the luminous efficiency
  • both Z and Z are 6-membered rings
  • the luminous efficiency can be further increased. It is preferable because it can further extend the service life.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • organic EL with higher luminous efficiency It can be set as an element.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent.
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R represents a hydrogen atom or a substituent.
  • a plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent.
  • the plurality of R may be the same or different.
  • an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be a long-life organic EL device.
  • the compound represented by the general formula (1) is preferably a compound having at least one group represented by any one of the general formulas (2-1) to (2-10). It is. In particular, it is more preferable that the molecule has 2 to 4 groups represented by deviations of the general formulas (2-1) to (2-10). At this time, in the structure represented by the general formula (1), R
  • R 1 to R 4 represent a hydrogen atom or a substituent
  • At least one of 601 606 601 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device having higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R to R represent a hydrogen atom or a substituent, but R to R
  • 611 620 At least one of 611 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 represent a hydrogen atom or a substituent
  • R 1 to R 5 At least one of the groups represents a group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R to R represent a hydrogen atom or a substituent.
  • 631 645 631 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 represent a hydrogen atom or a substituent
  • At least one of 651 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but the sum of na and nb is 6.
  • R to R represent a hydrogen atom or a substituent, but R to R
  • At least one of 661 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R 1 to R 5 represent a hydrogen atom or a substituent
  • 681 688 681 represents at least one group represented by any one of the general formulas (2-1) to (2-10).
  • an organic EL device with higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • R to R represent a hydrogen atom or a substituent.
  • At least one of R 1 represents a group represented by any one of the general formulas (2-1) to (2-10).
  • Examples of the divalent linking group represented by L include an alkylene group (for example, ethylene group, trimethylene).
  • At least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) N (R) —may be substituted with a group or the like.
  • divalent linking group represented by L for example, a group having a divalent heterocyclic group is used.
  • oxazole diyl group pyrimidine diyl group, pyridazine diyl group, pyrandyl group, pyrrolin diyl group, imidazoline diyl group, imidazolidine diyl group, pyrazolidine diyl group, pyrazoline diyl group, piperidine diyl group, piperazine diyl Group, morpholine diyl group, quinuclidine diyl group, etc., and compounds having an aromatic heterocycle such as thiophene 2,5 diyl group and pyrazine 2,3 diyl group (also called heteroaromatic compounds) ) Derived from a divalent linking group.
  • the alkylimino group, the dialkylsilane diyl group, and the diarylgermandyl group may be a group that connects and connects hetero atoms.
  • an organic EL device having higher luminous efficiency can be obtained.
  • the organic EL device can have a longer lifetime.
  • the substituent represented by 1 2 has the same meaning as the substituent represented by R in the general formula (1).
  • each of Z, Z, Z, and Z each represents a small number of nitrogen atoms.
  • 6-membered aromatic heterocyclic ring including both include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • each of Z and Z represents at least one nitrogen atom.
  • 6-membered aromatic heterocycle examples include pyridine ring, pyridazine ring, pyrimidine ring, Examples include a pyrazine ring.
  • Arylene groups represented by Ar and Ar include o-phenylene group and m-phenylene group, respectively.
  • P-phenylene naphthalenediyl, anthracenedyl, naphthacenedyl, pyrenezyl, naphthylnaphthalenediyl, biphenyl group (eg 3, 3'-biphenyl group, 3, 6-biphenyl group) Groups), terfelsyl groups, quaterfelsyl groups, kinkphenyl groups, sexphenyl groups, septiphenyl groups, octaphenyl groups, nobiphenyl groups, dephenyl groups, etc. .
  • the arylene group may further have a substituent described later.
  • the divalent aromatic heterocyclic groups represented by Ar and Ar are furan ring, thiophene ring,
  • Examples of the divalent linking group represented by L include the divalent group represented by L in the general formula (10).
  • the power which is synonymous with the linking group is preferably an alkylene group or a divalent group containing a chalcogen atom such as o s-, most preferably an alkylene group.
  • the aromatic heterocyclic group represented by 1 2 1 2 is a divalent group represented by Ar or Ar in the general formula (16).
  • heterocyclic ring examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • Examples of the divalent linking group represented by L include the divalent group represented by L in the general formula (10).
  • a force that is synonymous with the linking group of It is a divalent group containing a child, and is most preferably an alkylene group.
  • Exemplified Compound 74 was confirmed by 1 H-NMR ⁇ vector and mass spectrometry spectrum. The physical property data and spectrum data of Exemplified Compound 74 are shown below.
  • Exemplified Compound 60 was confirmed by NMR ⁇ vector and mass spectrometry spectrum.
  • the physical property data and spectrum data of Exemplified Compound 60 are shown below.
  • Exemplified Compound 143 was synthesized.
  • the compound represented by the general formula (1) according to the present invention preferably has a molecular weight of 00 or more, more preferably 450 or more, further preferably 600 or more, and particularly preferably.
  • the molecular weight is 800 or more.
  • the compound represented by the general formula (1) according to the present invention is a compound for an organic EL element (backlight, flat panel display, illumination light source, display element, electrophotographic light source, recording light source, exposure light source, Used for applications such as reading light sources, signs, signboards, interiors, optical communication devices, etc., but other uses include materials for organic semiconductor lasers (recording light sources, exposure light sources, reading light source optical communication devices, for electrophotography) Light source, etc.), electrophotographic photosensitive material, organic TFT element material (organic memory element, organic arithmetic element, organic switching element), organic wavelength conversion element material, photoelectric conversion element material (solar cell, photosensor, etc.) ) And can be used in a wide range of fields.
  • the hole transport layer is preferably adjacent to the anode, and the electron transport layer is preferably adjacent to the cathode.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, conductive transparent materials such as Cul, indium tinoxide (ITO), SnO, and ZnO. IDIXO (In O—ZnO) etc.
  • these electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by a single photolithography method. m or more), a pattern may be formed through a mask of a desired shape during the deposition or sputtering of the electrode material.
  • the transmittance is larger than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ Z or less.
  • the film thickness is a force depending on the material. Usually 10 to: L000 nm, preferably 10 to 20 Onm.
  • a cathode having a work function (4 eV or less) metal referred to as an electron injecting metal
  • an alloy referred to as an electrically conductive compound
  • a mixture thereof is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum Um (Al O)
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this, from the viewpoint of electron injecting properties and durability against acids, etc.
  • a magnesium Z silver mixture, a magnesium Z aluminum mixture, a magnesium Z indium mixture, an aluminum Z acid aluminum (Ai 2 o 3) mixture, a lithium Z aluminum mixture, aluminum and the like are suitable.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Also, the sheet resistance as a cathode is several hundred ⁇ / mouth or less, and the preferred film thickness is usually ⁇ !
  • the anode or the cathode of the organic EL element is transparent or semi-transparent to improve the emission luminance.
  • the transparent conductive material described in the description of the anode is formed thereon, whereby a transparent or translucent cathode is manufactured.
  • an element in which both the anode and the cathode are transmissive can be manufactured.
  • the injection layer is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. Hey.
  • the injection layer is a layer provided between the electrode and the organic layer in order to lower the driving voltage and improve the luminance of the light emission.
  • the organic EL element and the forefront of industrialization June 30, 1998) (Published by ES Co., Ltd.) ”, Chapter 2“ Chapter 2 Electrode Materials ”(pages 123-166) in detail, the hole injection layer (anode buffer layer) and electron injection layer (cathode buffer layer) There is.
  • anode buffer layer hole injection layer
  • a phthalocyanine buffer layer typified by phthalocyanine
  • an oxide buffer layer typified by vanadium oxide
  • an amorphous carbon buffer layer a polymer buffer layer using a conductive polymer such as polyarene (emeraldine) or polythiophene Etc.
  • the details of the cathode buffer layer are also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like.
  • the buffer layer is preferably a very thin film, although the film thickness is preferably in the range of 0.1 nm to 5 m, although it depends on the desired material.
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A-11 204258, 11-204359, and “Organic EL device and the forefront of its industrialization” (published by NTS Corporation on November 30, 1998). There is a hole blocking layer.
  • the hole blocking layer is an electron transporting layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.
  • the above-described compound according to the present invention is preferably contained as a hole blocking material of the hole blocking layer.
  • a hole blocking material of the hole blocking layer As a result, an organic EL device with even higher luminous efficiency can be obtained. Further, the lifetime can be further increased.
  • the electron blocking layer is a hole transport layer in a broad sense, and has a material force that has a function of transporting holes while transporting electrons, and is capable of transporting electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from an electrode, an electron transport layer, or a hole transport layer, and the light emitting portion is within the layer of the light emitting layer. It may be the interface between the light emitting layer and the adjacent layer.
  • the light emitting layer of the organic EL device of the present invention includes the following host compound and phosphorescent compound.
  • the present invention in which it is preferable to contain (also referred to as phosphorescent compound), it is preferable to use the compound according to the present invention described above as the host compound. As a result, the luminous efficiency can be further increased.
  • the host compound may contain a compound other than the compound according to the present invention.
  • the host compound is a room temperature among the compounds contained in the light emitting layer.
  • a phosphorescence quantum yield of phosphorescence emission at (25 ° C) is defined as a compound having a concentration of less than 0.01.
  • a plurality of known host compounds may be used in combination. By using multiple types of host compounds, it is possible to adjust the movement of charges, and the organic EL device can be made highly efficient. In addition, by using a plurality of phosphorescent compounds, it is possible to mix different light emission, thereby obtaining an arbitrary emission color. White light emission is possible by adjusting the type and amount of phosphorescent compound, and it can also be used for lighting and backlighting.
  • a compound having a hole transporting ability and an electron transporting ability, which prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • the light emitting layer further contains a host compound having a fluorescence maximum wavelength as the host compound. You may do it.
  • the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows electroluminescence as an organic EL device to be emitted from other host compounds having the maximum fluorescence wavelength.
  • What is preferable as a host compound having a fluorescence maximum wavelength is one having a high fluorescence quantum yield in a solution state.
  • the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.
  • Specific host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squame dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like.
  • the fluorescence quantum yield can be measured by the method described in the third edition of Experimental Chemistry Course 7, Spectroscopy II, page 362 (1992 edition, Maruzen).
  • the material used for the light emitting layer (hereinafter referred to as the light emitting material) preferably contains the above-mentioned host compound and at the same time contains a phosphorescent compound. As a result, an organic EL element with higher luminous efficiency can be obtained.
  • the phosphorescent compound according to the present invention is a compound in which light emission with an excited triplet force is observed, and is a compound that emits phosphorescence at room temperature (25 ° C). A compound having a rate of 0.01 or more at 25 ° C.
  • the phosphorescence quantum yield is preferably 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectra II, page 398 (1992 edition, Maruzen) of 4th edition, Experimental Chemistry Course 7.
  • the phosphorescence quantum yield in a solution can be measured using various solvents, but the phosphorescent compound used in the present invention achieves the above phosphorescence quantum yield in any solvent. Just do it.
  • the energy transfer type is to obtain light emission of phosphorescent compound force by transferring this energy to the phosphorescent compound, and the other is that the phosphorescent compound is a carrier trap.
  • This is a carrier trap type in which recombination of carriers occurs on the phosphorescent compound and light emission of a phosphorescent compound power is obtained.
  • the excited state energy of the phosphorescent compound is The condition is that the energy is lower than the excited state energy of the host compound.
  • the phosphorescent compound can be appropriately selected from known materials used for the light-emitting layer of the organic EL device.
  • the phosphorescent compound used in the present invention is preferably a complex compound containing a group 8 to group 10 metal in the periodic table of elements, more preferably an iridium compound or an osmium compound. Or a platinum compound (platinum complex compound) or a rare earth complex, and most preferred is an iridium compound.
  • the phosphorescent emission maximum wavelength of the phosphorescent compound is not particularly limited. In principle, by selecting a central metal, a ligand, a ligand substituent, and the like. The emission wavelength can be changed, but the phosphorescence emission wavelength of the phosphorescent compound is 3 It is preferable to have a phosphorescent maximum wavelength at 80-480nm! /. With such blue phosphorescent organic EL elements and white phosphorescent organic EL elements, the luminous efficiency can be further improved.
  • the light-emitting layer can be formed by depositing the above compound by a known thin film method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method.
  • the thickness of the light emitting layer is not particularly limited, but is usually selected within the range of 511111 to 5111, preferably 5 to 200 nm.
  • This light emitting layer may have a single layer structure in which these phosphorescent compounds and host compounds have one or more kinds of force, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions. ⁇ .
  • the hole transport layer is a hole transport material having a function of transporting holes.
  • a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has either injection or transport of holes and / or a barrier property of electrons, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, violazoline derivatives and pyrazolone derivatives, fluorenedamine derivatives, arylene amine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-1,4'-diamineamino; N, N' —Diphenyl N, N '— Bis (3-methylphenol) 1 [1, 1' — Biphenyl] 1, 4, 4 '— Diamine (TPD); 2, 2 Bis (4 Di-p-tolylaminophenol 1,1-bis (4 di-l-tri-laminophenol) cyclohexane; N, N, N ', N' —tetra-l-tolyl 4,4'-diaminobiphenyl; 1, 1 Bis (4 di-p-triaminophenol) 4 Phenol mouth hexane; Bis (4-dimethylamino 2-methylphenol) phenylmethane; Bis (4-di-p-triaminophenol) phenylmethane; N, N ' —Diphenyl N
  • No. 5,061,569 having two condensed aromatic rings in the molecule for example, 4, 4 ′ bis [N- (1-naphthyl) N ferroamino ] Biffle (NPD), three triphenylamine units described in Japanese Patent Laid-Open No. 4 308688 are connected in a starburst type 4, 4 ', A "— Tris [? ⁇ — (3 -Methylphenol) N-phenylamino] triphenylamine (MTD ATA).
  • a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used.
  • inorganic compounds such as p-type—Si and p-type—SiC can also be used as the hole injection material and the hole transport material.
  • the hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • the hole transport layer
  • the electron transport layer is a material force having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • An electron transport layer may be provided as a single layer or multiple layers.
  • an electron transport material also serving as a hole blocking material
  • Any material can be selected from conventionally known compounds as long as it has a function of transmitting electrons injected from the electrode to the light-emitting layer.
  • Examples include fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, strength rubodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxaziazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dibromone) 8quinolinol) aluminum, tris (2methyl 8-quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc., and the central metal of these metal complexes
  • Metal complexes in which is replaced with In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylvirazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, n-type—Si, n-type—SiC, etc. These inorganic semiconductors can also be used as electron transport materials.
  • the electron transport layer is obtained by thin-filming the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an inkjet method, or an LB method. Can be formed.
  • a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an inkjet method, or an LB method.
  • There is no particular limitation on the thickness of the electron transport layer but normally The thickness is about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
  • the electron transport layer may be a single layer structure having one or more of the above materials.
  • the organic EL device of the present invention is preferably formed on a substrate.
  • the substrate (hereinafter also referred to as substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is transparent.
  • the substrate is not particularly limited as long as it is used, but preferred examples of the substrate include glass, quartz, and a light-transmitting resin film.
  • a particularly preferable substrate is a resin film capable of imparting flexibility to the organic EL element.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyether etherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate. (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PES polyethersulfone
  • PC polyetherimide
  • polyether etherketone polyphenylene sulfide
  • PC cellulose triacetate
  • CAP cellulose acetate propionate
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted outside the organic EL element Z the number of electrons X 100 flowing through the organic EL element.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • a desired electrode material for example, a thin film having a material force for an anode is deposited by a method such as vapor deposition or sputtering so that the film thickness is 1 ⁇ m or less, preferably 10 to 200 nm.
  • a method such as vapor deposition or sputtering so that the film thickness is 1 ⁇ m or less, preferably 10 to 200 nm.
  • the deposition conditions are different due to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 to 10-2 Pa, deposition rate 0. 01 ⁇ 50nmZ seconds, substrate temperature-50 ⁇ 300. C, film thickness of 0.1 nm to 5 ⁇ m, preferably 5 to 200 nm, preferably selected appropriately.
  • a thin film that also has a material force for the cathode is formed thereon by a method such as vapor deposition or sputtering so that the film thickness becomes 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm.
  • a desired organic EL device can be obtained.
  • the organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
  • the multicolor display device of the present invention is provided with a shadow mask only at the time of forming a light emitting layer, and the other layers are common, so there is no need for patterning such as a shadow mask.
  • a film can be formed by a method, an inkjet method, a printing method, or the like.
  • the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable.
  • patterning using a shadow mask is preferred.
  • the order of preparation may be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode may be formed in this order.
  • a DC voltage is applied to the multi-color display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the anode as + and the cathode as one polarity.
  • An alternating voltage may be applied.
  • the AC waveform to be applied may be arbitrary.
  • the display device of the present invention can be used as a display device, a display, and various light emission sources. Display devices and displays can be displayed in full color by using three types of organic EL elements that emit blue, red, and green light.
  • Examples of the display device and display include a television, a computer, a mopile device, an AV device, a character broadcast display, and an information display in a car.
  • the driving method when used as a display device for reproducing moving images which may be used as a display device for reproducing still images or moving images, may be either a simple matrix (passive matrix) method or an active matrix method.
  • the lighting device of the present invention includes home lighting, interior lighting, backlights for clocks and liquid crystals, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Examples include, but are not limited to, a sensor light source.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the organic EL elements having such a resonator structure can be used for light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light sources of optical sensors, etc. It is not limited. In addition, it can be used for the above applications by causing laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device that projects an image, or a type that directly recognizes a still image or a moving image. It may be used as a display device (display).
  • the drive method may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using three or more organic EL elements of the present invention having different emission colors.
  • FIG. 1 is a schematic view showing an example of a display device configured with organic EL element power.
  • FIG. 2 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 also includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of the plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3, and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows the case where the light emitted from pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at orthogonal positions. (Details not shown).
  • the pixel 3 When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light according to the received image data.
  • Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • Full-color display can be performed by using organic EL elements of red, green, and blue light emission as organic EL elements 10 in a plurality of pixels and arranging them on the same substrate.
  • control unit B force is also connected to the drain of the switching transistor 11 via the data line 6.
  • An image data signal is applied to the screen.
  • a scanning signal is applied to the gate of the switching transistor 11 via the control unit B force scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of the star 12.
  • the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the organic EL element is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Current is supplied to element 10.
  • the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied.
  • the organic EL device 10 continues to emit light until it is seen.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for each of the organic EL elements 10 of each of the plurality of pixels.
  • Element 10 is emitting light.
  • Such a light emission method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission amount by a binary image data signal. On, even a talent! /.
  • the potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • FIG. 4 is a schematic diagram of a display device based on a noisy matrix method.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixel 3 connected to the applied scanning line 5 emits light in accordance with the image data signal.
  • the noisy matrix method pixel 3 has no active elements, and manufacturing costs can be reduced.
  • the organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by mixing colors.
  • the combination of multiple emission colors may include the three maximum emission wavelengths of the three primary colors of blue, green, and blue, and it uses the relationship of complementary colors such as blue and yellow, and blue-green and orange 2 It may be one containing two emission maximum wavelengths.
  • a combination of light-emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials (light-emitting dopants), a fluorescent material or a phosphorescent material that emits phosphorescence.
  • a dye material that emits light from the light emitting material as excitation light there is a difference between the light emitting materials!
  • the layer structure of the organic-electric-mouth luminescence device for obtaining a plurality of emission colors includes a method in which a plurality of emission dopants exist in one emission layer, a plurality of emission layers, and each emission Examples thereof include a method in which dopants having different emission wavelengths are present in the layer, and a method in which minute pixels emitting light of different wavelengths are formed in a matrix.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like at the time of film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire device layer may be patterned.
  • the light emitting material used for the light emitting layer is not particularly limited.
  • the platinum complex according to the present invention is adapted so as to conform to the wavelength range corresponding to the CF (color filter) characteristics. If you select any of the known luminescent materials and combine them to make them white.
  • the white light-emitting organic EL element is used as a variety of light-emitting light sources and illuminating devices, in addition to the display device and display, and is a kind of lamp such as home lighting, interior lighting, and exposure light source In addition, it is also useful for display devices such as backlights of liquid crystal display devices.
  • light sources such as backlights for watches, billboard advertisements, traffic lights, optical storage media, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, and display devices are also required. And a wide range of uses such as general household appliances.
  • the ITO transparent electrode was provided after patterning was performed on a substrate ( ⁇ Techno Glass Co., Ltd. ⁇ 45) obtained by depositing ITO (indium tin oxide) on a 100 mm X 100 mm XI .1 mm glass substrate as an anode.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation system, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat, and 100 mg of TCNQ is placed in another molybdenum resistance heating boat.
  • an electron blocking layer was provided so that the heating boat containing ex NPD was energized and heated, and deposited on the hole transport layer at a deposition rate of 0. InmZ seconds to a film thickness of lOnm. . Furthermore, the heating boat containing CBP and Ir 12 was energized and heated, and co-deposited on the electron blocking layer at a deposition rate of 0.2 nmZ seconds and 0.012 nmZ seconds, respectively, so that the film thickness became 35 nm. A light emitting layer was provided. In addition, the substrate temperature at the time of vapor deposition was room temperature. Furthermore, the heating boat containing BCP is energized and heated, and deposited on the light emitting layer at a deposition rate of 0. InmZ seconds. Then, a hole blocking layer having a thickness of 10 nm was provided. On top of that, the heated boat with further Alq
  • the film was evaporated on the electron transport layer at a deposition rate of 0. InmZ seconds, and an electron transport layer having a thickness of 40 nm was further provided.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the organic compound was similarly prepared except that CBP was used as an acceptor compound for the hole transport layer, and CBP was used as a compound for TCNQ and a host compound.
  • EL elements 1-2-1 to 15 were produced.
  • the organic EL devices 11 to 115 manufactured as described below were evaluated according to the following method to evaluate the external extraction efficiency and the driving voltage.
  • the fabricated organic EL device was measured for external extraction quantum efficiency (%) and driving voltage (V) when a constant current of 2.5 mA / cm 2 was applied at 23 ° C in a dry nitrogen gas atmosphere.
  • a spectral radiance meter CS-1000 manufactured by Co-Camino Norta Sensing was used in the same manner. The results obtained are shown in Table 1.
  • this transparent ITO electrode was provided.
  • the support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaned for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation system, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat, and another molybdenum resistance heating boat is placed in another molybdenum resistance heating boat.
  • the substrate temperature during vapor deposition was room temperature. Further, the heating boat containing BCP was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0. InmZ seconds to provide a hole blocking layer having a thickness of lOnm. On top of that, the heating boat containing Alq and triphenylamine is further energized and heated for vapor deposition.
  • An electron transport layer having a thickness of 80 nm was formed by co-evaporation on the hole blocking layer at a speed of 0.2 nmZ seconds and 0.004 nmZ seconds.
  • the substrate temperature during vapor deposition was room temperature.
  • organic EL device 2-1 In the production of the organic EL device 2-1, the BCP used as the donor compound of the electron transport layer! /, The triphenylamine and the hole blocking material was replaced as shown in Table 2. Except for the above, organic EL elements 2-2 to 2-10 were produced in the same manner.
  • a positive electrode A pattern was formed on a substrate ( ⁇ Techno Glass Co., Ltd. ⁇ 45) on which ITO (indium tin oxide) was formed on a 1 mm glass substrate, and this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system. Meanwhile, 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat, and 100 mg of TCNQ is placed in another molybdenum resistance heating boat.
  • the energized heating boat containing a-NPD and TCNQ was energized and heated, and the deposition rate was 0.2 nmZ seconds and 0.004 nmZ seconds. Then, a hole transport layer was provided so that the film thickness was lOOnm by co-evaporation on the transparent support substrate. Furthermore, NPD The heating boat was energized and heated, and an electron blocking layer was provided so that the film thickness was lOnm by vapor deposition on the hole transport layer at a deposition rate of 0. InmZ seconds.
  • the heating boat containing CBP and Ir-12 was energized and heated, and co-deposited on the electron blocking layer at a deposition rate of 0.2 nmZ seconds and 0.012 nmZ seconds, respectively, so that the film thickness became 35 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing BCP was energized and heated, and deposited on the light emitting layer at a deposition rate of 0. InmZ seconds to provide a hole blocking layer having a thickness of lOnm.
  • the heating bottle containing Alq and triphenylamine is added.
  • An electron transport layer having a thickness of 80 nm was formed by co-evaporation on the hole blocking layer at a deposition rate of 0.2 nmZ seconds and 0.004 nmZ seconds.
  • the substrate temperature during vapor deposition was room temperature.
  • organic EL device 3-1 As an acceptor compound for a hole transport layer, it is used as a TCNQ, as a donor compound for an electron transport layer! /, Used as a triphenylamine and a hole blocking material.
  • organic EL devices 3-2-3-12 were fabricated in the same manner as 3-1, except that the BCP was replaced as shown in Table 3.
  • Examples of the organic EL device 1-15 of the present invention produced in Example 1, the organic EL device 2-6 of the present invention produced in Example 2, and the phosphorescent compound of the organic EL device 2-6 of the present invention A red light-emitting organic EL device produced in the same manner except that the compound Ir 9 was used was placed side by side on the same substrate to produce an active matrix type full-color display device shown in FIG. Fig. 2 shows only a schematic diagram of display section A of the full-color display device that was fabricated.
  • the same substrate there are a plurality of pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6.
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material force, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions (details Not shown).
  • the plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, by arranging the red, green, and blue pixels as appropriate, full color display is possible.
  • Example 3 a heating boat containing CBP, a boat containing Ir-12, and a boat containing Ir-9 (also called Btp Ir (acac)) were independently provided.
  • the deposition rate of)) was adjusted to 100: 5: 0.6, and the organic EL device was manufactured in the same manner as organic EL device 3-5 except that a light emitting layer was provided so that the film thickness was 30 nm. Element 5-1W was fabricated. The non-light-emitting surface of the obtained organic EL element 5-1W was covered with a glass case, and the lighting device shown in FIGS. 5 (a) and 5 (b) was obtained.
  • the illuminating device could be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life.
  • an organic EL element, an illumination device, and a display device having a structure with excellent electro-optical characteristics having a low light-emitting element by reducing the resistance of an organic layer and high luminous efficiency are provided. It was.

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Abstract

Disclosed is an organic electroluminescent device comprising at least a light-emitting layer between a cathode and an anode which is characterized by comprising at least one layer containing at least one compound represented by the general formula (1) below and a hole-transporting layer containing a hole-transporting material and an acceptor compound. (In the formula, Z1 represents an aromatic heterocyclic ring, Z2 represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring, Z3 represents a divalent linking group or a bonding hand, and R101 represents a hydrogen atom or a substituent.)

Description

明 細 書  Specification
有機エレクト口ルミネッセンス素子、表示装置及び照明装置  Organic electoluminescence device, display device and lighting device
技術分野  Technical field
[0001] 本発明は、有機エレクト口ルミネッセンス素子、表示装置及び照明装置に関する。  TECHNICAL FIELD [0001] The present invention relates to an organic electoluminescence element, a display device, and a lighting device.
背景技術  Background art
[0002] 従来、発光型の電子ディスプレイデバイスとして、エレクト口ルミネッセンスディスプレ ィ（ELD)がある。 ELDの構成要素としては、無機エレクト口ルミネッセンス素子や有 機エレクト口ルミネッセンス素子（以下、有機 EL素子ともいう）が挙げられる。  [0002] Conventionally, as a light-emitting electronic display device, there is an electoric luminescence display (ELD). Examples of ELD constituent elements include inorganic electoluminescence devices and organic electroluminescence devices (hereinafter also referred to as organic EL devices).
[0003] 無機エレクト口ルミネッセンス素子は平面型光源として使用されてきたが、発光素子 を駆動させるためには交流の高電圧が必要である。  [0003] Inorganic electoluminescent elements have been used as planar light sources, but an AC high voltage is required to drive the light emitting elements.
[0004] 一方、有機 EL素子は、発光する化合物を含有する発光層を、陰極と陽極で挟んだ 構成を有し、発光層に電子及び正孔を注入して、再結合させることにより励起子 (ェ キシトン)を生成させ、このエキシトンが失活する際の光の放出（蛍光'リン光)を利用 して発光する素子であり、数 V〜数十 V程度の電圧で発光が可能であり、更に、 自己 発光型であるために視野角に富み、視認性が高ぐ薄膜型の完全固体素子であるた めに省スペース、携帯性等の観点から注目されて 、る。  [0004] On the other hand, an organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. By injecting electrons and holes into the light emitting layer and recombining them, excitons are obtained. This is an element that emits light by using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Furthermore, since it is a self-luminous type, it has a wide viewing angle, and since it is a thin-film type complete solid-state device with high visibility, it is attracting attention from the viewpoints of space saving and portability.
[0005] 今後の実用化に向けた有機 EL素子の開発としては、更に低消費電力で効率よく 高輝度に発光する有機 EL素子が望まれているわけであり、例えば、スチルベン誘導 体、ジスチリルァリーレン誘導体またはトリススチリルァリーレン誘導体に、微量の蛍 光体をドープし、発光輝度の向上、素子の長寿命化を達成する技術 (例えば、特許 文献 1参照。）、 8—ヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これに 微量の蛍光体をドープした有機発光層を有する素子 (例えば、特許文献 2参照。）、 8 ーヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これにキナクリドン系色素 をドープした有機発光層を有する素子 (例えば、特許文献 3参照。）等が知られてい る。  [0005] For the development of organic EL devices for practical use in the future, organic EL devices that emit light efficiently and with high brightness with lower power consumption are desired. For example, stilbene derivatives, distyryl Technology that improves light emission luminance and extends device lifetime by doping a small amount of phosphor into an arylene derivative or tristyrylarylene derivative (see, for example, Patent Document 1), 8-hydroxyquinoline aluminum complex A compound having an organic light-emitting layer doped with a trace amount of a phosphor (see, for example, Patent Document 2), 8-hydroxyquinoline aluminum complex as a host compound, and a quinacridone dye A device having an organic light emitting layer doped with (see, for example, Patent Document 3) is known.
[0006] 上記特許文献に開示されている技術では、励起一重項からの発光を用いる場合、 一重項励起子と三重項励起子の生成比が 1： 3であるため発光性励起種の生成確率 が 25%であることと、光の取り出し効率が約 20%であるため、外部取り出し量子効率 ( η ext)の限界は 5%とされている。 [0006] In the technique disclosed in the above-mentioned patent document, when light emission from excited singlet is used, the generation ratio of singlet excitons and triplet excitons is 1: 3. Is 25% and the light extraction efficiency is about 20%, so the limit of external extraction quantum efficiency (η ext) is 5%.
[0007] ところが、プリンストン大より、励起三重項からのリン光発光を用いる有機 EL素子の 報告 (例えば、非特許文献 1参照。）がされて以来、室温でリン光を示す材料の研究 が活発になってきている (例えば、非特許文献 2及び特許文献 4参照。 )0励起三重 項を使用すると、内部量子効率の上限が 100%となるため、励起一重項の場合に比 ベて原理的に発光効率力 倍となり、冷陰極管とほぼ同等の性能が得られ照明用に も応用可能であり注目されている。 [0007] However, since Princeton University reported on organic EL devices that use phosphorescence emission from excited triplets (for example, see Non-Patent Document 1), research on materials that exhibit phosphorescence at room temperature has been active. (For example, see Non-Patent Document 2 and Patent Document 4.) When the 0- excited triplet is used, the upper limit of the internal quantum efficiency is 100%, which is more fundamental than the case of the excited singlet. At the same time, its luminous efficiency is doubled, and almost the same performance as a cold cathode tube is obtained.
[0008] 例えば、多くの化合物がイリジウム錯体系等重金属錯体を中心に合成検討されて いる (例えば、非特許文献 3参照。 )0 [0008] For example, it has been many synthesized and studied compounds mainly heavy metal complexes such as iridium complexes (e.g., see non-patent document 3.) 0
[0009] また、ドーパントとして、トリス（2—フエ-ルビリジン)イリジウムを用いた検討がされて いる（例えば、非特許文献 2参照。 )0その他、ドーパントとして L Ir (acac)、例えば (p [0009] In addition, studies using tris (2-phenolidyne) iridium as a dopant have been made (for example, see Non-Patent Document 2). 0 In addition, L Ir ( acac ), for example (p
2  2
py) Ir(acac) (例えば、非特許文献 4参照。）を、また、ドーパントとして、トリス（2— ( py) Ir (acac) (see, for example, Non-Patent Document 4) and Tris (2— (
2 2
3 V ^ 3 V ^
zq) )、Ir (bzq) C1P (Bu) 3等を用いた検討 (例えば、非特許文献 5参照。）が行われ zq)), Ir (bzq) C1P (Bu) 3 etc. (for example, see Non-Patent Document 5)
3 2 3 2
ている。  ing.
[0010] また、高い発光効率を得るために、ホール輸送性の化合物をリン光性ィ匕合物のホス トとして用いている（例えば、非特許文献 6参照。 )0 [0010] In order to obtain a high luminous efficiency, is used hole transporting compound as the host of the phosphorescent I匕合(e.g., Non-Patent Document 6 reference.) 0
[0011] また、各種電子輸送性材料をリン光性ィ匕合物のホストとして、これらに新規なイリジ ゥム錯体をドープして用いている（例えば、非特許文献 4参照)。更に、ホールブロッ ク層の導入により高い発光効率を得ている（例えば、非特許文献 5参照)。  [0011] Further, various electron transport materials are used as a host of phosphorescent compounds, and these are doped with a novel iridium complex (for example, see Non-Patent Document 4). Furthermore, high luminous efficiency is obtained by introducing a hole block layer (see, for example, Non-Patent Document 5).
[0012] また、正孔輸送層中にァクセプター化合物を、電子輸送層中にドナー化合物をド ープすることにより、熱平衡状態における正孔輸送層と電子輸送層内のキャリア濃度 を上げることで、有機層の導電率を向上される方法が提案されている (例えば、特許 文献 5、 6、 7参照。；)。また更に、ドナー化合物をドープした電子輸送層と正孔を効率 的に閉じ込める正孔阻止層力 成る有機エレクト口ルミネッセンス素子や、ァクセプタ 一化合物をドープした正孔輸送層と電子を効率的に閉じ込める電子阻止層から成る 有機エレクト口ルミネッセンス素子が提案され、更に高い発光効率を持つ電気光学特 性に優れた構成の有機エレクト口ルミネッセンス素子が得られている（例えば、特許文 献 8参照。）。 [0012] Further, by doping the acceptor compound in the hole transport layer and the donor compound in the electron transport layer, the carrier concentration in the hole transport layer and the electron transport layer in the thermal equilibrium state is increased, A method for improving the conductivity of the organic layer has been proposed (see, for example, Patent Documents 5, 6, and 7). Furthermore, the electron transport layer doped with the donor compound and the hole-blocking layer force that efficiently confines the holes, or the hole transport layer doped with the acceptor compound and the electrons that efficiently confine the electrons. An organic-electric-luminescence device consisting of a blocking layer has been proposed, and it has an electro-optic characteristic with higher luminous efficiency. An organic-electric-luminescence element with a superior structure has been obtained (see, for example, Patent Document 8).
[0013] し力しながら、更なる高い発光効率の向上、更なる有機層の低抵抗ィ匕による素子の 低電圧化された有機エレクト口ルミネッセンス素子が望まれている。  [0013] However, there is a demand for an organic electoluminescence device in which the voltage of the device is lowered by further improving the luminous efficiency and further reducing the resistance of the organic layer.
特許文献 1：特許第 3093796号明細書  Patent Document 1: Patent No. 3093796
特許文献 2：特開昭 63 - 264692号公報  Patent Document 2: Japanese Patent Laid-Open No. 63-264692
特許文献 3 :特開平 3— 255190号公報  Patent Document 3: JP-A-3-255190
特許文献 4:米国特許第 6, 097, 147号明細書  Patent Document 4: U.S. Patent No. 6,097,147
特許文献 5：特開平 4— 297076号公報  Patent Document 5: Japanese Patent Laid-Open No. 4-297076
特許文献 6：特開 2001— 244079号公報  Patent Document 6: Japanese Patent Laid-Open No. 2001-244079
特許文献 7：国際公開第 04Z074399号パンフレット  Patent Document 7: International Publication No. 04Z074399 Pamphlet
特許文献 8：特開 2000 - 196140号公報  Patent Document 8: Japanese Unexamined Patent Publication No. 2000-196140
非特許文献 1 : M. A. Baldo et al. , nature, 395卷、 151— 154頁（1998年） 非特許文献 2 : M. A. Baldo et al. , nature、 403卷、 17号、 750— 753頁（200 0年）  Non-patent literature 1: MA Baldo et al., Nature, 395 卷, 151–154 (1998) Non-patent literature 2: MA Baldo et al., Nature, 403 卷, 17, 750–753 (200 0) Year)
非特許文献 3 : S. Lamansky et al. , J. Am. Chem. Soc. , 123卷、 4304頁（2 001年）  Non-Patent Document 3: S. Lamansky et al., J. Am. Chem. Soc., 123 卷, 4304 (2 001)
非特許文献 4: M. E. Tompson et al. , The 10th Internatioternational Workshop on Inorganic and Organic Electroluminescence (EL ' 00、浜 松）  Non-Patent Document 4: M. E. Tompson et al., The 10th Internatioternational Workshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu)
非特許文献 5 : Moon— Jae Youn. 0g， Tetsuo Tsutsuiet al. , The 10th In ternational Workshop on Inorganic and Organic Electroluminescenc e (EL，00、浜松）  Non-Patent Document 5: Moon— Jae Youn. 0g, Tetsuo Tsutsuiet al., The 10th International Workshop on Inorganic and Organic Electroluminescence (EL, 00, Hamamatsu)
非特許文献 6 :Ikai et al.， The 10th International Workshop on Inorga nic and Organic Electroluminescence (EL 500、浜松) Non-Patent Document 6:. Ikai et al, The 10th International Workshop on Inorga nic and Organic Electroluminescence (EL 5 00, Hamamatsu)
発明の開示  Disclosure of the invention
[0014] 本発明の目的は、有機層の低抵抗化による素子の低電圧化、並びに高い発光効 率をもつ電気光学的特性に優れた構成の有機 EL素子、照明装置及び表示装置を 提供することである。 [0014] An object of the present invention is to provide an organic EL element, a lighting device, and a display device having a structure with excellent electro-optical characteristics, which has a low emission voltage due to a low resistance of the organic layer and a high luminous efficiency. Is to provide.
[0015] 上記目的を達成するための、本発明の態様の一つは、陰極と陽極との間に発光層 を少なくとも有する有機エレクト口ルミネッセンス素子にぉ 、て、少なくとも 1層に下記 一般式（1)で表される化合物の少なくとも 1種を含有し、且つ正孔輸送材料及びァク セプター化合物を含有する正孔輸送層を有することを特徴とする有機エレクト口ルミ ネッセンス素子にある。  [0015] In order to achieve the above object, one embodiment of the present invention is an organic electoluminescence device having at least a light emitting layer between a cathode and an anode, and at least one layer of the following general formula ( An organic electrification device comprising a hole transport layer containing at least one compound represented by 1) and containing a hole transport material and an acceptor compound.
[0016] [化 1]  [0016] [Chemical 1]
-般式 (1)-General formula (1)
Figure imgf000006_0001
Figure imgf000006_0001
[0017] (式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を表 (Wherein Z represents an aromatic heterocycle, Z represents an aromatic heterocycle or an aromatic hydrocarbon ring.
1 2  1 2
し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表 Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。）  The )
図面の簡単な説明  Brief Description of Drawings
[0018] [図 1]有機 EL素子力も構成される表示装置の一例を示した模式図である。 [0018] FIG. 1 is a schematic diagram showing an example of a display device that also has organic EL element force.
[図 2]表示部 Aの模式図である。  FIG. 2 is a schematic diagram of display unit A.
[図 3]画素を構成する駆動回路の等価回路図である。  FIG. 3 is an equivalent circuit diagram of a drive circuit constituting a pixel.
[図 4]パッシブマトリックス方式による表示装置の模式図である。  FIG. 4 is a schematic diagram of a passive matrix display device.
[図 5]有機 EL素子を具備してなる照明装置の模式図である。  FIG. 5 is a schematic view of a lighting device including an organic EL element.
発明を実施するための最良の形態  BEST MODE FOR CARRYING OUT THE INVENTION
[0019] 本発明の上記目的は、下記構成により達成された。 [0019] The above object of the present invention has been achieved by the following constitution.
(1) 陰極と陽極との間に発光層を少なくとも有する有機エレクト口ルミネッセンス素 子にお 1、て、少なくとも 1層に下記一般式（1)で表される化合物の少なくとも 1種を含 有し、且つ正孔輸送材料及びァクセプター化合物を含有する正孔輸送層を有するこ とを特徴とする有機エレクト口ルミネッセンス素子。 (1) An organic electoluminescence device having at least a light-emitting layer between a cathode and an anode, and at least one layer contains at least one compound represented by the following general formula (1) And an organic electroluminescence device having a hole transporting layer containing a hole transporting material and an acceptor compound.
[化 1] 一般式 (1 )
Figure imgf000007_0001
[Chemical formula 1] General formula (1)
Figure imgf000007_0001
[0021] (式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を表 (In the formula, Z represents an aromatic heterocycle, Z represents an aromatic heterocycle or an aromatic hydrocarbon ring.
1 2  1 2
し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表 Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。）  The )
(2) 陰極と陽極との間に発光層を少なくとも有する有機エレクト口ルミネッセンス素 子にお 1、て、少なくとも 1層に下記一般式（1)で表される化合物の少なくとも 1種を含 有し、且つ電子輸送材料及びドナー化合物を含有する電子輸送層を有することを特 徴とする有機エレクト口ルミネッセンス素子。  (2) An organic electoluminescence device having at least a light emitting layer between a cathode and an anode, and at least one layer contains at least one compound represented by the following general formula (1) And an organic electroluminescence device having an electron transport layer containing an electron transport material and a donor compound.
[0022] [化 1] 一般式 (1 >
Figure imgf000007_0002
[0022] [Chemical 1] General formula (1>
Figure imgf000007_0002
[0023] (式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を表 し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表[0023] (In the formula, Z represents an aromatic heterocyclic ring, Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring. Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。 ) (3) 電子輸送材料及びドナー化合物を含有する電子輸送層を更に有すること を特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子。  The (3) The organic electoluminescence device according to (1), further comprising an electron transport layer containing an electron transport material and a donor compound.
(4) 前記一般式（1)で表される化合物の Z力 員環であることを特徴とする前記（1)  (4) The above (1), which is a Z-membered ring of the compound represented by the general formula (1)
1  1
〜（3)の!、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to item 1 of ~ (3), displacement force.
(5) 前記一般式（1)で表される化合物の Z力 員環であることを特徴とする前記（1)  (5) The above-mentioned (1), which is a Z-membered ring of the compound represented by the general formula (1)
2  2
〜（4)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence element according to item 1 of ~ 4.
(6) 前記一般式（1)で表される化合物の Zが結合手であることを特徴とする前記（1  (6) Z in the compound represented by the general formula (1) is a bond,
3  Three
)〜（5)の!、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  ) To (5) !, displacement force The organic electoluminescence device according to item 1.
(7) 前記一般式（1)で表される化合物が分子量 450以上であることを特徴とする前 記（1)〜（6)の!、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (7) The organic electoluminescence device according to (1) to (6) above, wherein the compound represented by the general formula (1) has a molecular weight of 450 or more, and a displacement force of 1.
(8) 前記一般式（1)で表される化合物が下記一般式（1 1)で表されることを特徴 とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (8) The organic elect according to item (1), wherein the compound represented by the general formula (1) is represented by the following general formula (11): Mouth luminescence element.
[0024] [化 2] 一般式 ί1一 1)  [0024] [Chemical formula 2] General formula ί1 一 1)
Figure imgf000008_0001
Figure imgf000008_0001
[0025] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
501 507  501 507
(9) 前記一般式（1)で表される化合物が下記一般式（1 2)で表されることを特徴 とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (9) The organic elect described in (1) to (7) above, wherein the compound represented by the general formula (1) is represented by the following general formula (12): Mouth luminescence element.
[0026] [化 3] 一般式 (1一 2)
Figure imgf000009_0001
[0026] [Chemical 3] General formula (1 1 2)
Figure imgf000009_0001
[0027] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
511 517  511 517
(10) 前記一般式（1)で表される化合物が下記一般式（1 3)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (10) The organic compound according to item 1, wherein the compound represented by the general formula (1) is represented by the following general formula (13): Elect mouth luminescence element.
[0028] [化 4] 一般式 (1一 3)
Figure imgf000009_0002
[0028] [Chemical formula 4] General formula (1 1 3)
Figure imgf000009_0002
[0029] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
521 527  521 527
(11) 前記一般式（1)で表される化合物が下記一般式（1 4)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (11) The organic compound according to item 1 above, wherein the compound represented by the general formula (1) is represented by the following general formula (14): Elect mouth luminescence element.
[0030] [化 5] 一般式 (1一 4)
Figure imgf000009_0003
[0031] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [0030] [Chemical formula 5] General formula (1 1 4)
Figure imgf000009_0003
[Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
531 537  531 537
(12) 前記一般式（1)で表される化合物が下記一般式（1 5)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (12) The organic compound according to item 1, wherein the compound represented by the general formula (1) is represented by the following general formula (15): Elect mouth luminescence element.
[0032] [化 6] 一般式 (1—5)
Figure imgf000010_0001
[0032] [Chemical 6] General formula (1-5)
Figure imgf000010_0001
[0033] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 3 each independently represents a hydrogen atom or a substituent.]
541 548  541 548
(13) 前記一般式（1)で表される化合物が下記一般式（1 6)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (13) The organic compound according to (1) above, wherein the compound represented by the general formula (1) is represented by the following general formula (16): Elect mouth luminescence element.
[0034] [化 7] 一般式 (1一 6)
Figure imgf000010_0002
[0034] [Chemical formula 7] General formula (1 1 6)
Figure imgf000010_0002
[0035] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
551 558  551 558
(14) 前記一般式（1)で表される化合物が下記一般式（1 7)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (14) The organic compound according to item 1 above, wherein the compound represented by the general formula (1) is represented by the following general formula (17): Elect mouth luminescence element.
[0036] [化 8] -般式 (1一 7)
Figure imgf000011_0001
[0036] [Chemical 8] -General formula (1 1 7)
Figure imgf000011_0001
[0037] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
561 567  561 567
(15) 前記一般式（1)で表される化合物が下記一般式（1 8)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (15) The organic compound according to item 1, wherein the compound represented by the general formula (1) is represented by the following general formula (18): Elect mouth luminescence element.
[0038] [化 9] 一般式 (1一 8)
Figure imgf000011_0002
[0038] [Chemical 9] General formula (1-8)
Figure imgf000011_0002
[0039] (式中、 R 〜R は各々独立に水素原子または置換基を表す。） [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
571 577  571 577
(16) 前記一般式（1)で表される化合物が下記一般式（1 9)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (16) The organic compound according to item 1 above, wherein the compound represented by the general formula (1) is represented by the following general formula (19): Elect mouth luminescence element.
[0040] [化 10] [0040] [Chemical 10]
-般式 (1一 9)
Figure imgf000011_0003
-General formula (1 1 9)
Figure imgf000011_0003
(式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) (17) 前記一般式（1)で表される化合物が下記一般式（1 10)で表されることを特 徴とする前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。 (In the formula, R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different.) (17) The organic compound according to item 1, wherein the compound represented by the general formula (1) is represented by the following general formula (110): Elect mouth luminescence element.
[化 11] 一般式 (1一 10)
Figure imgf000012_0001
[Chemical formula 11] General formula (1 1 10)
Figure imgf000012_0001
[0043] (式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) [Wherein, R represents a hydrogen atom or a substituent. Further, a plurality of R may be the same or different from each other.)
(18) 前記一般式（1)で表される化合物が下記一般式（2— 1)〜（2— 10)のいずれ かで表される基を少なくとも一つ有することを特徴とする前記（1)〜（7)の 、ずれか 1 項に記載の有機エレクト口ルミネッセンス素子。  (18) The compound represented by the general formula (1) has at least one group represented by any one of the following general formulas (2-1) to (2-10): The organic electoluminescence device according to any one of items 1) to (7).
[0044] [化 12] [0044] [Chemical 12]
-般式 (2 1 ) 一般式 (2— 2)-General formula (2 1) General formula (2 — 2)
Figure imgf000013_0001
Figure imgf000013_0001
一般式 (2— 3) -般式 (2— 4) General formula (2-3)-General formula (2-4)
Figure imgf000013_0002
Figure imgf000013_0002
一般式 (2— 5) -般式 (2— 6) General formula (2— 5)-General formula (2— 6)
Figure imgf000013_0003
Figure imgf000013_0003
-般式 (2— 7) —般式 (2— 8)  -General formula (2—7) —General formula (2—8)
-般-General
Figure imgf000013_0004
(式中、 R ： R 〜： R 、： R 〜： R 、： R 〜： R 、： R
Figure imgf000013_0004
(In the formula, R: R-: R,: R-: R,: R-: R,: R
5
Figure imgf000013_0005
532 537 542 548 552 558 562Five
Figure imgf000013_0005
532 537 542 548 552 558 562
〜R 、 R , R 〜： R , R -R は各々独立に水素原子または置換基を表 ~ R, R, R ~: R and R-R each independently represents a hydrogen atom or a substituent.
577 588 592 598  577 588 592 598
し、該置換基は各々同一でもよぐ異なっていてもよい。 ) (19) 前記一般式（1)で表される化合物が下記一般式 (3)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。 The substituents may be the same or different. ) (19) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (3): Luminescence element.
[化 13] 一般式 (3)
Figure imgf000014_0001
[Chemical 13] General formula (3)
Figure imgf000014_0001
[0047] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (Wherein R 1 to R 4 are each independently a hydrogen atom or a substituent having a small force R 1 to R 2)
601 606 601 606 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  601 606 601 606 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(20) 前記一般式（1)で表される化合物が下記一般式 (4)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (20) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (4): Luminescence element.
[0048] [化 14] 一般式 (4)
Figure imgf000014_0002
[0048] [Chem. 14] General formula (4)
Figure imgf000014_0002
[0049] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 2)
611 620 611 620 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  611 620 611 620 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(21) 前記一般式（1)で表される化合物が下記一般式 (5)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (21) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (5): Luminescence element.
[0050] [化 15] 一般式 (5)
Figure imgf000015_0001
[0050] [Chemical 15] General formula (5)
Figure imgf000015_0001
[0051] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [0051] (wherein R to R each independently represents a hydrogen atom or a substituent having a small force R to R)
621 623 621 623 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  621 623 621 623 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(22) 前記一般式（1)で表される化合物が下記一般式 (6)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (22) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (6): Luminescence element.
[0052] [化 16] 一般式 (6> [0052] [Chem. 16] General formula (6>
Figure imgf000015_0002
Figure imgf000015_0002
[0053] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [0053] (wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 5)
631 645 631 645 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  631 645 631 645 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(23) 前記一般式（1)で表される化合物が下記一般式 (7)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (23) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (7): Luminescence element.
[0054] [化 17] 一般式 (7)
Figure imgf000016_0001
[0054] [Chemical 17] General formula (7)
Figure imgf000016_0001
[0055] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [0055] (wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 2)
651 656 651 656 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの禾ロは 6である。）  651 656 651 656 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but na and nb are 6. )
(24) 前記一般式（1)で表される化合物が下記一般式 (8)で表されることを特徴と する前記（1)〜（7)のレ、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (24) The organic electo described in (1) to (7) above, wherein the compound represented by the general formula (1) is represented by the following general formula (8): Mouth luminescence element.
[0056] [化 18] 般式 (8)
Figure imgf000016_0002
[0056] [Chem. 18] General formula (8)
Figure imgf000016_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
661 672 661 672 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 ) 661 672 661 672 At least one of the basic forces represented by the general formulas (2-1) to (2-10) is selected. Represents one group. )
(25) 前記一般式（1)で表される化合物が下記一般式 (9)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (25) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (9): Luminescence element.
[0058] [化 19] 一般式 (9)  [0058] [Chem. 19] General formula (9)
Figure imgf000017_0001
Figure imgf000017_0001
[0059] (式中、 R 〜R 〜R [0059] (wherein R to R to R
681 688は各々独立に水素原子または置換基を表す力 R  681 and 688 are each independently a force representing a hydrogen atom or a substituent R
681 688の少な くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  At least one of 681 688 represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(26) 前記一般式（1)で表される化合物が下記一般式（10)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (26) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (10): Luminescence element.
[0060] [化 20] 般式 (10)
Figure imgf000017_0002
[0061] (式中、 R 〜R は各々独立に水素原子または置換基を表すが、 Lは 2価の連結基[0060] [Chemical formula 20] General formula (10)
Figure imgf000017_0002
[0061] (wherein R to R each independently represents a hydrogen atom or a substituent, L represents a divalent linking group)
691 700 1 691 700 1
を表す。 R 〜R の少なくとも一つは前記一般式（2— 1)〜（2— 10)で表される基  Represents. At least one of R 1 to R 4 is a group represented by the general formula (2-1) to (2-10).
691 700  691 700
力も選ばれる少なくとも一つの基を表す。 )  Force also represents at least one group selected. )
(27) 前記一般式（1)で表される化合物が下記一般式（11)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (27) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (11): Luminescence element.
[0062] [化 21] [0062] [Chemical 21]
Figure imgf000018_0001
Figure imgf000018_0001
[0063] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) (28) 前記一般式（1)で表される化合物が下記一般式（12)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. (28) The organic electr according to item (1), wherein the compound represented by the general formula (1) is represented by the following general formula (12): Mouth luminescence element.
[0064] [化 22] [0064] [Chemical 22]
Figure imgf000019_0001
Figure imgf000019_0001
[0065] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) (29) 前記一般式（1)で表される化合物が下記一般式（13)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. (29) The organic electr according to item (1), wherein the compound represented by the general formula (1) is represented by the following general formula (13): Mouth luminescence element.
[0066] [化 23] 一般式 (13)
Figure imgf000019_0002
[0066] [Chemical Formula 23] General formula (13)
Figure imgf000019_0002
[0067] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) (30) 前記一般式（1)で表される化合物が下記一般式（14)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。 [0068] [化 24] 一般式 (14)
Figure imgf000020_0001
K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. (30) The organic electr according to item (1), wherein the compound represented by the general formula (1) is represented by the following general formula (14): Mouth luminescence element. [0068] [Chemical formula 24] General formula (14)
Figure imgf000020_0001
[0069] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) (31) 前記一般式（1)で表される化合物が下記一般式（15)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. (31) The organic electr according to item 1 above, wherein the compound represented by the general formula (1) is represented by the following general formula (15): Mouth luminescence element.
[0070] [化 25] 一般式 (15)
Figure imgf000020_0002
[0070] [Chemical 25] General formula (15)
Figure imgf000020_0002
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 Z  K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z
1 1
、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複素環を表す。 ) (32) 前記一般式（1)で表される化合物が下記一般式（16)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。 , Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. ) (32) The organic elect mouth according to (1) above, wherein the compound represented by the general formula (1) is represented by the following general formula (16): Luminescence element.
[化 26] 一般式 Π6)
Figure imgf000021_0001
[Chemical formula 26] General formula Π6)
Figure imgf000021_0001
[0073] (式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳 [0073] (In the formula, o and p each represent an integer of 1 to 3, Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複  Represents an aromatic heterocyclic group. Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
1 2  1 2
素環を表し、 Lは 2価の連結基を表す。 )  Represents a prime ring, and L represents a divalent linking group. )
(33) 前記一般式（1)で表される化合物が下記一般式（17)で表されることを特徴と する前記（1)〜（7)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (33) The organic elect mouth according to (1), wherein the compound represented by the general formula (1) is represented by the following general formula (17): Luminescence element.
[0074] [化 27] 一般式 (17) [0074] [Chemical 27] General formula (17)
Figure imgf000021_0002
[0075] (式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳
Figure imgf000021_0002
[0075] (In the formula, o and p each represent an integer of 1 to 3, Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳  Represents an aromatic heterocyclic group. Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
1 2 3 4  1 2 3 4
香族複素環を表し、 Lは 2価の連結基を表す。 )  Represents an aromatic heterocycle, and L represents a divalent linking group. )
(34) 前記ァクセプター化合物が Au、 Pt、 W、 Ir、 POC1、 AsF、 CI、 Br、 I、 TC  (34) The acceptor compound is Au, Pt, W, Ir, POC1, AsF, CI, Br, I, TC
3 6 2 2 2 3 6 2 2 2
NQ、 TCNQF4、 TCNE、 HCNB、 DDQ、 TNF、 DNF、フルオラ-ル、クロラエル、 ブロマ-ルカ 選ばれることを特徴とする前記（1)、 (3)〜（33)の 、ずれか 1項に記 載の有機エレクト口ルミネッセンス素子。 NQ, TCNQF4, TCNE, HCNB, DDQ, TNF, DNF, fluoral, chlorael, bromale, selected from the above (1), (3) to (33) The organic-elect mouth luminescence element described.
(35) 前記正孔輸送層が陽極に隣接していることを特徴とする前記（1)、 （3)〜（34 )の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (35) The organic electroluminescent device according to (1), (3) to (34), wherein the hole transport layer is adjacent to the anode.
(36) 前記ドナー化合物がアルカリ金属、アルカリ土類金属もしくはそれらの塩であ ることを特徴とする前記（2)〜（33)の 、ずれか 1項に記載の有機エレクト口ルミネッセ ンス素子。  (36) The organic electroluminescence device according to any one of (2) to (33), wherein the donor compound is an alkali metal, an alkaline earth metal, or a salt thereof.
(37) 前記アルカリ金属の塩がセシウムの塩であることを特徴とする前記（36)に記 載の有機エレクト口ルミネッセンス素子。  (37) The organic electoluminescence device according to (36), wherein the alkali metal salt is a cesium salt.
(38) 前記電子輸送層が陰極に隣接していることを特徴とする前記 (2)〜（33)、 (3 6)、 (37)の!、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (38) The organic electoluminescence according to (1) above, wherein the electron transport layer is adjacent to the cathode, and (2) to (33), (36), (37)! element.
(39) 前記一般式（1)で表される化合物の少なくとも 1種を含有する層が正孔阻止 層であることを特徴とする前記（1)〜（38)の 、ずれか 1項に記載の有機エレクトロル ミネッセンス素子。  (39) The layer according to any one of (1) to (38), wherein the layer containing at least one compound represented by the general formula (1) is a hole blocking layer. Organic electroluminescence element.
(40) 発光が白色であることを特徴とする前記（1)〜（39)のいずれか 1項に記載の 有機エレクト口ルミネッセンス素子。  (40) The organic electoluminescence device according to any one of (1) to (39), wherein the light emission is white.
(41) 前記 (40)に記載の有機エレクト口ルミネッセンス素子を有することを特徴とす る表示装置。  (41) A display device comprising the organic electoluminescence device according to (40).
(42) 前記 (40)に記載の有機エレクト口ルミネッセンス素子を有することを特徴とす る照明装置。  (42) An illuminating device comprising the organic electoluminescence device according to (40).
(43) 前記 (42)に記載の照明装置と表示手段としての液晶素子を有することを特 徴とする表示装置。  (43) A display device comprising the illumination device according to (42) and a liquid crystal element as display means.
[0076] 本発明は、陰極と陽極との間に発光層を少なくとも有する有機エレクト口ルミネッセ ンス素子にお 、て、該有機エレクト口ルミネッセンス素子は少なくとも 1層に前記一般 式（1)で表される化合物の少なくとも 1種を含有し、且つ正孔輸送材料及びァクセプ ター化合物を含有する正孔輸送層を有すること、または電子輸送材料及びドナー化 合物を含有する電子輸送層を有すること、更にはその両者を有することを特徴として いる。 [0076] The present invention relates to an organic electoluminescence having at least a light emitting layer between a cathode and an anode. In the active element, the organic electoluminescence element contains at least one compound represented by the general formula (1) in at least one layer, and contains a positive hole transport material and an acceptor compound. It is characterized by having a hole transport layer or having an electron transport layer containing an electron transport material and a donor compound, and further having both.
[0077] ァクセプター化合物としては、 Au、 Pt、 W、 Ir、 POC1、 AsF、 CI、 Br、 I等の無  [0077] Examples of acceptor compounds include Au, Pt, W, Ir, POC1, AsF, CI, Br, and I.
3 6 2 2 2 機材料、 TCNQ (7, 7, 8, 8—テトラシァノキノジメタン）、 TCNQF4 (テトラフルォロ テトラシァノキノジメタン）、 TCNE (テトラシァノエチレン）、 HCNB (へキサシァノブタ ジェン）、 DDQ (ジシクロジシァノベンゾキノン）等のシァノ基を有する化合物、 TNF ( トリ-トロフルォレノン）、 DNF (ジニトロフルォレノン）等の-トロ基を有する化合物、フ ルオラニル、クロラエル、ブロマ-ル等の有機材料が挙げられる。この内、 TCNQ、 T CNQF4、 TCNE, HCNB, DDQ等のシァノ基を有する化合物がより好ましい。  3 6 2 2 2 Materials, TCNQ (7, 7, 8, 8—tetracyanoquinodimethane), TCNQF4 (tetrafluorotetracyanodimethane), TCNE (tetracyanoethylene), HCNB (hexacia nobutagen), Compounds having a cyano group such as DDQ (dicyclodisianobenzoquinone), compounds having a -tro group such as TNF (tri-trofluorenone), DNF (dinitrofluorenone), organics such as fluoranil, chlorael and bromale Materials. Of these, compounds having a cyano group such as TCNQ, TCNQF4, TCNE, HCNB, and DDQ are more preferred.
[0078] 正孔輸送材料に対するァクセプター化合物の添加割合は、 1〜20質量％であるこ とが好ましい。 [0078] The addition ratio of the acceptor compound to the hole transport material is preferably 1 to 20% by mass.
[0079] ドナー化合物としては、アルカリ金属及びアルカリ土類金属として周期表のものが 挙げられ、それらの塩としては、例えば、カルボン酸塩 (酢酸塩等）、スルホン酸塩 (メ タンスルホン酸塩、トシル酸塩等）、ハロゲン化物（フッ化物、塩化物、臭化物及びヨウ 化物）、水酸化物、炭酸塩、硝酸塩及び硫酸塩等が挙げられる。この中で、セシウム の塩がより好ましい。  [0079] Examples of donor compounds include those of the periodic table as alkali metals and alkaline earth metals, and examples of salts thereof include carboxylates (acetates, etc.), sulfonates (methanesulfonates). , Tosylates, etc.), halides (fluorides, chlorides, bromides and iodides), hydroxides, carbonates, nitrates and sulfates. Of these, a cesium salt is more preferred.
[0080] 電子輸送材料に対するドナー化合物の添加割合は、 1〜20質量％であることが好 ましい。  [0080] The addition ratio of the donor compound to the electron transporting material is preferably 1 to 20% by mass.
[0081] 本発明に係る一般式（1)で表される化合物は、後述する有機 EL素子の構成層の 構成成分として用いられるが、本発明では、本発明の有機 EL素子の構成層の中で 発光層または正孔阻止層に含有されることが好ましぐ特に好ましくは正孔阻止層に 含有される。但し、有機 EL素子の種々の物性コントロールの観点から、必要に応じて 本発明に係る化合物は、有機 EL素子のその他の構成層に用いてもょ 、。  [0081] The compound represented by the general formula (1) according to the present invention is used as a constituent component of a constituent layer of an organic EL element described later. In the light emitting layer or the hole blocking layer, it is particularly preferable that it is contained in the hole blocking layer. However, from the viewpoint of controlling various physical properties of the organic EL device, the compound according to the present invention may be used in other constituent layers of the organic EL device, if necessary.
[0082] 《一般式 (1)で表される化合物》  [0082] << Compound Represented by Formula (1) >>
本発明に係る一般式（1)で表される化合物につ 、て説明する。 [0083] 前記一般式（1)において、 Zは置換基を有してもよい芳香族複素環を表し、 Zは置 The compound represented by the general formula (1) according to the present invention will be described. [0083] In the general formula (1), Z represents an aromatic heterocyclic ring which may have a substituent, and Z represents a substituent.
1 2 換基を有してもよい芳香族複素環、もしくは芳香族炭化水素環を表し、 Zは 2価の連  1 2 represents an aromatic heterocycle or an aromatic hydrocarbon ring which may have a substituent, and Z represents a divalent linkage.
3 結基、もしくは単なる結合手を表す。 R は水素原子、もしくは置換基を表す。  3 Indicates a bond or a simple bond. R represents a hydrogen atom or a substituent.
101  101
[0084] Z、 Zで表される芳香族複素環としては、フラン環、チォフェン環、ピリジン環、ピリ  [0084] Aromatic heterocycles represented by Z and Z include furan ring, thiophene ring, pyridine ring,
1 2  1 2
ダジン環、ピリミジン環、ピラジン環、トリアジン環、ベンゾイミダゾール環、ォキサジァ ゾール環、トリァゾール環、イミダゾール環、ピラゾール環、チアゾール環、インドール 環、ベンゾイミダゾール環、ベンゾチアゾール環、ベンゾォキサゾール環、キノキサリ ン環、キナゾリン環、フタラジン環、力ルバゾール環、カルボリン環、ジァザカルバゾー ル環 (カルボリン環を構成する炭化水素環の炭素原子の一つが更に窒素原子で置 換されている環を示す)等が挙げられる。更に前記芳香族複素環は、後述する R で  Dazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxari Ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, diazacarbazole ring (showing a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further replaced by a nitrogen atom), etc. It is done. Further, the aromatic heterocycle is R as described later.
101 表される置換基を有してもょ ヽ。  101 It may have a substituent represented.
[0085] Zで表される芳香族炭化水素環としては、ベンゼン環、ビフエ-ル環、ナフタレン環  [0085] The aromatic hydrocarbon ring represented by Z includes a benzene ring, a biphenyl ring, and a naphthalene ring.
2  2
、ァズレン環、アントラセン環、フエナントレン環、ピレン環、タリセン環、ナフタセン環、 トリフエ-レン環、 o—テルフエ-ル環、 m—テルフエ-ル環、 p—テルフエ-ル環、ァ セナフテン環、コロネン環、フルオレン環、フルオラントレン環、ナフタセン環、ペンタ セン環、ペリレン環、ペンタフェン環、ピセン環、ピレン環、ピラントレン環、アンスラァ ントレン環等が挙げられる。更に前記芳香族炭化水素環は、後述する R で表される  , Azulene ring, anthracene ring, phenanthrene ring, pyrene ring, taricene ring, naphthacene ring, triphenylene ring, o-terfel ring, m-terfel ring, p-terfel ring, acenaphthene ring, coronene And a ring, a fluorene ring, a fluoranthrene ring, a naphthacene ring, a pentacene ring, a perylene ring, a pentaphen ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthanthrene ring. Further, the aromatic hydrocarbon ring is represented by R described later.
101 置換基を有してもよい。  101 may have a substituent.
[0086] R で表される置換基としては、アルキル基（例えば、メチル基、ェチル基、プロピル  [0086] Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).
101  101
基、イソプロピル基、 tert—ブチル基、ペンチル基、へキシル基、ォクチル基、ドデシ ル基、トリデシル基、テトラデシル基、ペンタデシル基等）、シクロアルキル基 (例えば 、シクロペンチル基、シクロへキシル基等）、ァルケ-ル基 (例えば、ビュル基、ァリル 基等）、アルキニル基 (例えば、ェチニル基、プロパルギル基等）、ァリール基 (例えば Group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.) Alkenyl group (for example, buyl group, allyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), aryl group (for example,
、フエ-ル基、ナフチル基等)、芳香族複素環基 (例えば、フリル基、チェ-ル基、ピリ ジル基、ピリダジ -ル基、ピリミジ -ル基、ピラジュル基、トリアジニル基、イミダゾリル 基、ピラゾリル基、チアゾリル基、キナゾリ-ル基、フタラジニル基等）、複素環基 (例 えば、ピロリジル基、イミダゾリジル基、モルホリル基、ォキサゾリジル基等）、アルコキ シル基 (例えば、メトキシ基、エトキシ基、プロピルォキシ基、ペンチルォキシ基、へキ シルォキシ基、ォクチルォキシ基、ドデシルォキシ基等）、シクロアルコキシル基 (例 えば、シクロペンチルォキシ基、シクロへキシルォキシ基等）、ァリールォキシ基 (例え ば、フエノキシ基、ナフチルォキシ基等）、アルキルチオ基 (例えば、メチルチオ基、ェ チルチオ基、プロピルチオ基、ペンチルチオ基、へキシルチオ基、ォクチルチオ基、 ドデシルチオ基等）、シクロアルキルチオ基 (例えば、シクロペンチルチオ基、シクロ へキシルチオ基等）、ァリールチオ基 (例えば、フエ-ルチオ基、ナフチルチオ基等） 、アルコキシカルボ-ル基（例えば、メチルォキシカルボ-ル基、ェチルォキシカルボ ニル基、ブチルォキシカルボ-ル基、ォクチルォキシカルボ-ル基、ドデシルォキシ カルボ-ル基等）、ァリールォキシカルボ-ル基（例えば、フエ-ルォキシカルボ-ル 基、ナフチルォキシカルボ-ル基等）、スルファモイル基（例えば、アミノスルホ -ル基 、メチルアミノスルホ -ル基、ジメチルアミノスルホ -ル基、ブチルアミノスルホ -ル基 、へキシルアミノスルホ -ル基、シクロへキシルアミノスルホ -ル基、ォクチルアミノス ルホ-ル基、ドデシルアミノスルホ-ル基、フエ-ルアミノスルホ -ル基、ナフチルアミ ノスルホ -ル基、 2—ピリジルアミノスルホ -ル基等）、ァシル基 (例えば、ァセチル基 、ェチルカルボ-ル基、プロピルカルボ-ル基、ペンチルカルボ-ル基、シクロへキ シルカルボ-ル基、ォクチルカルポ-ル基、 2—ェチルへキシルカルボ-ル基、ドデ シルカルボ-ル基、フ -ルカルポ-ル基、ナフチルカルボ-ル基、ピリジルカルボ -ル基等）、ァシルォキシ基 (例えば、ァセチルォキシ基、ェチルカルボニルォキシ 基、ブチルカルボ-ルォキシ基、ォクチルカルボ-ルォキシ基、ドデシルカルボ -ル ォキシ基、フエニルカルボ-ルォキシ基等）、アミド基 (例えば、メチルカルボ-ルアミ ノ基、ェチルカルボ-ルァミノ基、ジメチルカルボ-ルァミノ基、プロピルカルボ-ルァ ミノ基、ペンチルカルボ-ルァミノ基、シクロへキシルカルボ-ルァミノ基、 2—ェチル へキシルカルボ-ルァミノ基、ォクチルカルボ-ルァミノ基、ドデシルカルボ-ルァミノ 基、フ -ルカルポ-ルァミノ基、ナフチルカルボ-ルァミノ基等）、力ルバモイル基（ 例えば、ァミノカルボ-ル基、メチルァミノカルボ-ル基、ジメチルァミノカルボ-ル基 、プロピルアミノカルボ-ル基、ペンチルァミノカルボ-ル基、シクロへキシルァミノ力 ルポ-ル基、ォクチルァミノカルボ-ル基、 2—ェチルへキシルァミノカルボ-ル基、 ドデシルァミノカルボ-ル基、フエ-ルァミノカルボ-ル基、ナフチルァミノカルボ-ル 基、 2—ピリジルァミノカルボニル基等）、ウレイド基 (例えば、メチルウレイド基、ェチ ルゥレイド基、ペンチルゥレイド基、シクロへキシルウレイド基、ォクチルゥレイド基、ド デシルゥレイド基、フ ニルゥレイド基ナフチルウレイド基、 2—ピリジルアミノウレイド 基等）、スルフィエル基（例えば、メチルスルフィ-ル基、ェチルスルフィ-ル基、プチ ルスルフィ-ル基、シクロへキシルスルフィエル基、 2—ェチルへキシルスルフィエル 基、ドデシルスルフィエル基、フヱニルスルフィ-ル基、ナフチルスルフィ-ル基、 2— ピリジルスルフィ -ル基等）、アルキルスルホ -ル基（例えば、メチルスルホ -ル基、ェ チルスルホ-ル基、ブチルスルホ -ル基、シクロへキシルスルホ -ル基、 2—ェチル へキシルスルホ -ル基、ドデシルスルホ -ル基等）、ァリールスルホ -ル基（フエ-ル スルホ-ル基、ナフチルスルホ-ル基、 2—ピリジルスルホ -ル基等）、アミノ基（例え ば、アミノ基、ェチルァミノ基、ジメチルァミノ基、ブチルァミノ基、シクロペンチルァミノ 基、 2—ェチルへキシルァミノ基、ドデシルァミノ基、ァ-リノ基、ナフチルァミノ基、 2 ピリジルァミノ基等）、ハロゲン原子 (例えば、フッ素原子、塩素原子、臭素原子等） 、フッ化炭化水素基（例えば、フルォロメチル基、トリフルォロメチル基、ペンタフルォ 口ェチル基、ペンタフルォロフエ-ル基等）、シァノ基、ニトロ基、ヒドロキシル基、メル カプト基、シリル基 (例えば、トリメチルシリル基、トリイソプロビルシリル基、トリフエ-ル シリル基、フエ二ルジェチルシリル基等）、等が挙げられる。 , Phenyl group, naphthyl group, etc.), aromatic heterocyclic group (e.g. furyl group, chael group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, triazinyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, quinazolyl group, phthalazinyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propyloxy group) Group, pentyloxy group, hexyl Siloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (eg, cyclopentyloxy group, cyclohexyloxy group etc.), aryloxy group (eg, phenoxy group, naphthyloxy group etc.), alkylthio group (eg, methylthio group) Group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, etc.) , Naphthylthio group, etc.), alkoxy carbo yl groups (for example, methyloxy carbo yl group, eth oxy carbonyl group, butyl oxy carbo ol group, oct oxy oxy carbo ol group, dodecyloxy carbo ol- Group), aryloxy group (for example, For example, a phenyl group, a naphthyl group, etc.), a sulfamoyl group (for example, an aminosulfol group, a methylaminosulfol group, a dimethylaminosulfol group, a butylaminosulfol group, Hexylaminosulfol group, cyclohexylaminosulfol group, octylaminosulfur group, dodecylaminosulfol group, phenolaminosulfol group, naphthylaminosulfol group, 2-pyridylaminosulfol group Etc.), an acyl group (for example, an acetyl group, an ethyl carbonate group, a propyl carbon group, a pentyl carbonate group, a cyclohexyl carbonyl group, an octyl carboxyl group, a 2-ethylhexyl carbo ol group, Dodecylcarbol group, fullcarporo group, naphthylcarbol group, pyridylcarbol group, etc.), acyloxy group (for example, A cetyloxy group, an ethylcarbonyloxy group, a butylcarboxoxy group, an octylcarboxoxy group, a dodecylcarboxoxy group, a phenylcarboxoxy group, etc.), an amide group (for example, a methylcarboamino group, an ethylcarboluminamino group, Dimethyl carbolumino group, propyl carbolumino group, pentyl carbolumino group, cyclohexyl carbolumino group, 2-ethyl hexyl carbolumino group, octyl carbolumino group, dodecyl carbolumino group, furocarpo- Lumino group, naphthyl carbolumino group, etc.), rubamoyl group (for example, amino carbo group, methyl amino carbo ol group, dimethyl amino carbo ol group, propyl amino carbo ol group, pentyl amino carbo ol-) Group, cyclohexylamino group, group Ruaminokarubo - group, hexyl § to 2 Echiru amino carbo - group, dodecyl § amino carbo - group, Hue - Ruaminokarubo - group, naphthyl § amino carbo - Le Group, 2-pyridylaminocarbonyl group, etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc.), sulfier groups (for example, methylsulfyl group, ethylsulfuryl group, propylsulfuryl group, cyclohexylsulfifer group, 2-ethylhexylsulfiel group, dodecylsulfiel group, Phenylsulfyl group, naphthylsulfuryl group, 2-pyridylsulfyl group, etc.), alkylsulfol group (for example, methylsulfol group, ethylsulfol group, butylsulfol group, cyclohexylsulfol group) -Luyl group, 2-ethyl hexylsulfol group, dodecylsulfo- Group), arylsulfol group (phenylsulfol group, naphthylsulfol group, 2-pyridylsulfol group, etc.), amino group (eg, amino group, ethylamino group, dimethylamino group, butyramino group). , Cyclopentylamino groups, 2-ethylhexylamino groups, dodecylamino groups, a-lino groups, naphthylamino groups, 2-pyridylamino groups, etc., halogen atoms (eg fluorine atoms, chlorine atoms, bromine atoms, etc.), fluorinated hydrocarbons Group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyan group, nitro group, hydroxyl group, mercapto group, silyl group (for example, trimethylsilyl group, Triisopropylpropyl silyl group, triphenyl silyl group, phenyljetyl silyl group, etc.).
[0087] これらの置換基は上記の置換基によって更に置換されて!、てもよ!/、。また、これら の置換基は複数が互いに結合して環を形成して 、てもよ 、。好ま 、置換基としては 、アルキル基、シクロアルキル基、フッ化炭化水素基、ァリール基、芳香族複素環基 である。 [0087] These substituents may be further substituted with the above substituents! In addition, a plurality of these substituents may be bonded to each other to form a ring. Preferably, the substituent is an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, or an aromatic heterocyclic group.
[0088] 2価の連結基としては、アルキレン、ァルケ-レン、アルキ-レン、ァリーレンなどの 炭化水素基の他、ヘテロ原子を含むものであってもよぐまたチォフェン 2, 5 ジ ィル基ゃピラジン 2, 3 ジィル基のような芳香族複素環を有する化合物 (ヘテロ芳 香族化合物ともいう）に由来する 2価の連結基であってもよいし、酸素や硫黄などの力 ルコゲン原子であってもよい。また、アルキルイミノ基、ジアルキルシランジィル基ゃジ ァリールゲルマンジィル基のようなヘテロ原子を会して連結する基でもよい。  [0088] Examples of the divalent linking group include hydrocarbon groups such as alkylene, alkene, alkylene, and arylene, and those that contain a heteroatom or thiophene 2, 5 diyl group. It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a pyrazine 2,3 diyl group (also referred to as a heteroaromatic compound), or it may be a force lucogen atom such as oxygen or sulfur. There may be. Further, it may be a group that joins heteroatoms such as an alkylimino group, a dialkylsilane diyl group, or a diarylgermandyl group.
[0089] 単なる結合手とは、連結する置換基同士を直接結合する結合手である。 [0090] 本発明においては、前記一般式（1)の Z力 員環であることが好ましい。これにより [0089] The simple bond is a bond that directly bonds the substituents to be linked. In the present invention, the Z-membered ring represented by the general formula (1) is preferable. This
1  1
、より発光効率を高くすることができる。更に一層長寿命化させることができる。また、 本発明においては、 z力 ½員環であることが好ましい。これにより、より発光効率を高く  , The luminous efficiency can be further increased. Further, the life can be extended. In the present invention, a z-membered ring is preferable. This increases the luminous efficiency
2  2
することができる。更により一層長寿命化させることができる。更に Zと Zを共に 6員環  can do. Further, the lifetime can be further increased. Furthermore, both Z and Z are 6-membered rings
1 2  1 2
とすることで、より一層発光効率と高くすることができるので好ましい。更により一層長 寿命化させることができるので好まし 、。  It is preferable because the luminous efficiency can be further increased. It is preferable because it can further extend the service life.
[0091] 前記一般式（1)で表される化合物で好ましいのは、前記一般式（1 1)〜（1 10) で各々表される化合物である。  [0091] Among the compounds represented by the general formula (1), compounds represented by the general formulas (11) to (110) are preferable.
[0092] 前記一般式（1 1)において、 R 〜R は各々独立に水素原子もしくは置換基を [0092] In the general formula (11), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
501 507  501 507
表す。一般式（1— 1)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-1), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0093] 前記一般式（1 2)において、 R 〜R は各々独立に水素原子もしくは置換基を [0093] In the general formula (12), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
511 517  511 517
表す。一般式（1— 2)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-2), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0094] 前記一般式（1 3)において、 R 〜R は各々独立に水素原子もしくは置換基を [0094] In the general formula (13), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
521 527  521 527
表す。一般式（1— 3)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-3), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0095] 前記一般式（1 4)において、 R 〜R は各々独立に水素原子もしくは置換基を [0095] In the general formula (14), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
531 537  531 537
表す。一般式（1—4)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-4), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0096] 前記一般式（1 5)において、 R 〜R は各々独立に水素原子もしくは置換基を [0096] In the general formula (15), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
541 548  541 548
表す。一般式（1— 5)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-5), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0097] 前記一般式（1 6)において、 R 〜R は各々独立に水素原子もしくは置換基を [0097] In the general formula (16), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
551 558  551 558
表す。一般式（1— 6)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-6), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0098] 前記一般式（1 7)において、 R 〜R は各々独立に水素原子もしくは置換基を [0098] In the general formula (17), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
561 567  561 567
表す。一般式（1— 7)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。 To express. By using the compound represented by general formula (1-7), organic EL with higher luminous efficiency It can be set as an element. In addition, the organic EL device can have a longer lifetime.
[0099] 前記一般式（1 8)において、 R 〜R は各々独立に水素原子もしくは置換基を [0099] In the general formula (18), R 1 to R 5 each independently represents a hydrogen atom or a substituent.
571 577  571 577
表す。一般式（1— 8)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。更により長寿命の有機 EL素子とすることができる。  To express. By using the compound represented by the general formula (1-8), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0100] 前記一般式（1— 9)において、 Rは水素原子もしくは置換基を表す。また、複数の R は各々同一でもよぐ異なっていてもよい。一般式（1 9)で表される化合物を用いる ことで、より発光効率の高い有機 EL素子とすることができる。更により長寿命の有機 E L素子とすることができる。  [0100] In the general formula (1-9), R represents a hydrogen atom or a substituent. A plurality of R may be the same or different. By using the compound represented by the general formula (19), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain an organic EL device having a longer life.
[0101] 前記一般式（1— 10)において、 Rは水素原子もしくは置換基を表す。また、複数の Rは各々同一でもよぐ異なっていてもよい。一般式（1 10)で表される化合物を用 いることで、より発光効率の高い有機 EL素子とすることができる。更に長寿命の有機 EL素子とすることができる。  [0101] In the general formula (1-10), R represents a hydrogen atom or a substituent. The plurality of R may be the same or different. By using the compound represented by the general formula (110), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be a long-life organic EL device.
[0102] また、前記一般式（1)で表される化合物で好ましいものは、前記一般式（2—1)〜（ 2— 10)のいずれかで表される基を少なくとも一つを有する化合物である。特に、分 子内に前記一般式（2— 1)〜（2— 10)の 、ずれかで表される基を 2つから 4つ有する ことがより好ましい。このとき、前記一般式（1)で表される構造において、 R  [0102] The compound represented by the general formula (1) is preferably a compound having at least one group represented by any one of the general formulas (2-1) to (2-10). It is. In particular, it is more preferable that the molecule has 2 to 4 groups represented by deviations of the general formulas (2-1) to (2-10). At this time, in the structure represented by the general formula (1), R
101を除いた 部分が前記一般式 (2— 1)〜（2— 10)に置き換わる場合を含む。  This includes the case where the part excluding 101 is replaced by the general formulas (2-1) to (2-10).
[0103] このとき、特に前記一般式 (3)〜（17)で表される化合物であることが本発明の効果 を得る上で好ましい。 [0103] At this time, the compounds represented by the general formulas (3) to (17) are particularly preferable for obtaining the effects of the present invention.
[0104] 前記一般式（3)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R  [0104] In the general formula (3), R 1 to R 4 represent a hydrogen atom or a substituent,
601 606 601 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 At least one of 601 606 601 represents a group represented by any one of the general formulas (2-1) to (2-10).
606 606
す。一般式 (3)で表される化合物を用いることにより、より発光効率の高い有機 EL素 子とすることができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (3), an organic EL device having higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0105] 前記一般式 (4)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R [0105] In the general formula (4), R to R represent a hydrogen atom or a substituent, but R to R
611 620 611 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 611 620 At least one of 611 represents a group represented by any one of the general formulas (2-1) to (2-10).
620 620
す。一般式 (4)で表される化合物を用いることで、より発光効率の高い有機 EL素子と することができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (4), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0106] 前記一般式（5)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表In the general formula (5), R 1 to R 5 represent a hydrogen atom or a substituent, and R 1 to R 5 At least one of the groups represents a group represented by any one of the general formulas (2-1) to (2-10).
623 623
す。一般式 (5)で表される化合物を用いることで、より発光効率の高い有機 EL素子と することができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (5), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0107] 前記一般式 (6)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R  [0107] In the general formula (6), R to R represent a hydrogen atom or a substituent.
631 645 631 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 631 645 631 represents a group represented by any one of the general formulas (2-1) to (2-10).
645 645
す。一般式 (6)で表される化合物を用いることで、より発光効率の高い有機 EL素子と することができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (6), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0108] 前記一般式（7)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R  [0108] In the general formula (7), R 1 to R 5 represent a hydrogen atom or a substituent,
651 656 651 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 651 656 At least one of 651 represents a group represented by any one of the general formulas (2-1) to (2-10).
656 656
す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの和が 6である。一 般式 (7)で表される化合物を用いることで、より発光効率の高!、有機 EL素子とするこ とができる。更により長寿命の有機 EL素子とすることができる。  The na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but the sum of na and nb is 6. By using the compound represented by the general formula (7), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0109] 前記一般式 (8)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R  [0109] In the general formula (8), R to R represent a hydrogen atom or a substituent, but R to R
661 672 661 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 661 672 At least one of 661 represents a group represented by any one of the general formulas (2-1) to (2-10).
672 672
す。一般式 (8)で表される化合物を用いることで、より発光効率の高い有機 EL素子と することができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (8), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0110] 前記一般式（9)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜R  [0110] In the general formula (9), R 1 to R 5 represent a hydrogen atom or a substituent,
681 688 681 の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表 681 688 681 represents at least one group represented by any one of the general formulas (2-1) to (2-10).
688 688
す。一般式 (9)で表される化合物を用いることで、より発光効率の高い有機 EL素子と することができる。更により長寿命の有機 EL素子とすることができる。  The By using the compound represented by the general formula (9), an organic EL device with higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0111] 前記一般式（10)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜  [0111] In the general formula (10), R to R represent a hydrogen atom or a substituent.
691 700 691 691 700 691
R の少なくとも一つは前記一般式（2— 1)〜（2— 10)のいずれかで表される基を表At least one of R 1 represents a group represented by any one of the general formulas (2-1) to (2-10).
700 700
す。  The
[0112] Lで表される 2価の連結基としては、アルキレン基 (例えば、エチレン基、トリメチレ  [0112] Examples of the divalent linking group represented by L include an alkylene group (for example, ethylene group, trimethylene).
1  1
ン基、テトラメチレン基、プロピレン基、ェチルエチレン基、ペンタメチレン基、へキサ メチレン基、 2, 2, 4 トリメチルへキサメチレン基、ヘプタメチレン基、オタタメチレン 基、ノナメチレン基、デカメチレン基、ゥンデカメチレン基、ドデカメチレン基、シクロへ キシレン基 (例えば、 1, 6 シクロへキサンジィル基等）、シクロペンチレン基 (例えば 、 1, 5 シクロペンタンジィル基など）等）、ァルケ-レン基 (例えば、ビ-レン基、プロ ベ-レン基等）、アルキ-レン基 (例えば、ェチ-レン基、 3—ペンチ-レン基等）、ァ リーレン基などの炭化水素基の他、ヘテロ原子を含む基 (例えば、 O 、一 S 等 のカルコゲン原子を含む 2価の基、—N (R)—基、ここで Rは水素原子またはアルキ ル基を表し、該アルキル基は、前記一般式（1)にお 、て R で表されるアルキル基と Group, tetramethylene group, propylene group, ethylethylene group, pentamethylene group, hexamethylene group, 2, 2, 4 trimethylhexamethylene group, heptamethylene group, otatamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group Group, cyclohexylene group (for example, 1,6-cyclohexanediyl group, etc.), cyclopentylene group (for example, , 1, 5 cyclopentandyl group, etc.), alkenylene group (for example, beylene group, probelene group, etc.), alkylene group (for example, ethylene group, 3-pentyl group) In addition to hydrocarbon groups such as arylene groups, etc., groups containing heteroatoms (eg, divalent groups containing chalcogen atoms such as O 1, 1 S, etc., —N (R) — groups, where R Represents a hydrogen atom or an alkyl group, and the alkyl group is an alkyl group represented by R in the general formula (1).
101  101
同義である）等が挙げられる。また、上記のアルキレン基、ァルケ-レン基、アルキ- レン基、ァリーレン基の各々においては、 2価の連結基を構成する炭素原子の少なく とも一つが、カルコゲン原子 (酸素、硫黄等)や前記 N (R)—基等で置換されてい てもよい。  And the like). Further, in each of the above alkylene group, alkene group, alkylene group, and arylene group, at least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) N (R) —may be substituted with a group or the like.
[0113] 更に Lで表される 2価の連結基としては、例えば、 2価の複素環基を有する基が用  [0113] Further, as the divalent linking group represented by L, for example, a group having a divalent heterocyclic group is used.
1  1
いられ、例えば、ォキサゾールジィル基、ピリミジンジィル基、ピリダジンジィル基、ピ ランジィル基、ピロリンジィル基、イミダゾリンジィル基、イミダゾリジンジィル基、ピラゾ リジンジィル基、ピラゾリンジィル基、ピぺリジンジィル基、ピぺラジンジィル基、モル ホリンジィル基、キヌクリジンジィル基等が挙げられ、またチォフェン 2, 5 ジィル 基や、ピラジン 2, 3 ジィル基のような、芳香族複素環を有する化合物 (ヘテロ芳 香族化合物ともいう）に由来する 2価の連結基であってもよい。また、アルキルイミノ基 、ジアルキルシランジィル基ゃジァリールゲルマンジィル基のようなヘテロ原子を会し て連結する基であってもよ 、。  For example, oxazole diyl group, pyrimidine diyl group, pyridazine diyl group, pyrandyl group, pyrrolin diyl group, imidazoline diyl group, imidazolidine diyl group, pyrazolidine diyl group, pyrazoline diyl group, piperidine diyl group, piperazine diyl Group, morpholine diyl group, quinuclidine diyl group, etc., and compounds having an aromatic heterocycle such as thiophene 2,5 diyl group and pyrazine 2,3 diyl group (also called heteroaromatic compounds) ) Derived from a divalent linking group. In addition, the alkylimino group, the dialkylsilane diyl group, and the diarylgermandyl group may be a group that connects and connects hetero atoms.
[0114] 前記一般式（10)で表される化合物を用いることで、より発光効率の高!ヽ有機 EL素 子とすることができる。更により長寿命の有機 EL素子とすることができる。  [0114] By using the compound represented by the general formula (10), an organic EL device having higher luminous efficiency can be obtained. In addition, the organic EL device can have a longer lifetime.
[0115] 前記一般式（11)〜一般式（15)で各々表される化合物において、 R、 Rで各々表  [0115] In the compounds represented by the general formula (11) to the general formula (15),
1 2 される置換基としては、前記一般式（1)において R で表される置換基と同義である  The substituent represented by 1 2 has the same meaning as the substituent represented by R in the general formula (1).
101  101
[0116] 前記一般式（15)において、 Z、 Z、 Z、 Zで各々表される、各々窒素原子を少なく [0116] In the general formula (15), each of Z, Z, Z, and Z each represents a small number of nitrogen atoms.
1 2 3 4  1 2 3 4
とも一つ含む 6員の芳香族複素環としては、例えば、ピリジン環、ピリダジン環、ピリミ ジン環、ピラジン環等が挙げられる。  Examples of the 6-membered aromatic heterocyclic ring including both include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
[0117] 前記一般式（16)において、 Z、 Zで各々表される、各々窒素原子を少なくとも一つ [0117] In the general formula (16), each of Z and Z represents at least one nitrogen atom.
1 2  1 2
含む 6員の芳香族複素環としては、例えば、ピリジン環、ピリダジン環、ピリミジン環、 ピラジン環等が挙げられる。 Examples of the 6-membered aromatic heterocycle include pyridine ring, pyridazine ring, pyrimidine ring, Examples include a pyrazine ring.
[0118] Ar、 Arで各々表されるァリーレン基としては、 o—フエ-レン基、 m—フエ-レン基  [0118] Arylene groups represented by Ar and Ar include o-phenylene group and m-phenylene group, respectively.
1 2  1 2
、 p—フエ-レン基、ナフタレンジィル基、アントラセンジィル基、ナフタセンジィル基、 ピレンジィル基、ナフチルナフタレンジィル基、ビフエ-ルジィル基（例えば、 3, 3' ービフヱ-ルジィル基、 3, 6—ビフヱ-ルジィル基等）、テルフエ-ルジィル基、クァ テルフエ-ルジィル基、キンクフエ-ルジィル基、セキシフエ-ルジィル基、セプチフ ェ-ルジィル基、ォクチフエ-ルジィル基、ノビフエ-ルジィル基、デシフエ-ルジィ ル基等が挙げられる。また前記ァリーレン基は、更に後述する置換基を有していても よい。 Ar、 Arで各々表される 2価の芳香族複素環基は、フラン環、チォフェン環、ピ  , P-phenylene, naphthalenediyl, anthracenedyl, naphthacenedyl, pyrenezyl, naphthylnaphthalenediyl, biphenyl group (eg 3, 3'-biphenyl group, 3, 6-biphenyl group) Groups), terfelsyl groups, quaterfelsyl groups, kinkphenyl groups, sexphenyl groups, septiphenyl groups, octaphenyl groups, nobiphenyl groups, dephenyl groups, etc. . The arylene group may further have a substituent described later. The divalent aromatic heterocyclic groups represented by Ar and Ar are furan ring, thiophene ring,
1 2  1 2
リジン環、ピリダジン環、ピリミジン環、ピラジン環、トリアジン環、ベンゾイミダゾール環 、ォキサジァゾール環、トリァゾール環、イミダゾール環、ピラゾール環、チアゾール環 、インドール環、ベンゾイミダゾール環、ベンゾチアゾール環、ベンゾォキサゾール環 、キノキサリン環、キナゾリン環、フタラジン環、力ルバゾール環、カルボリン環、カルボ リン環を構成する炭化水素環の炭素原子が更に窒素原子で置換されている環等か ら導出される 2価の基等が挙げられる。更に前記芳香族複素環基は、前記 R で表さ  Lysine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring , Quinoxaline, quinazoline, phthalazine, carbazole, carboline, divalent groups derived from rings in which the carbon atom of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom, etc. Is mentioned. Further, the aromatic heterocyclic group is represented by R.
101 れる置換基を有してもよい。  It may have a substituent.
[0119] Lで表される 2価の連結基としては、前記一般式（10)において、 Lで表される 2価  [0119] Examples of the divalent linking group represented by L include the divalent group represented by L in the general formula (10).
1  1
の連結基と同義である力 好ましくはアルキレン基、 o s—等のカルコゲン原 子を含む 2価の基であり、最も好ましくはアルキレン基である。  The power which is synonymous with the linking group is preferably an alkylene group or a divalent group containing a chalcogen atom such as o s-, most preferably an alkylene group.
[0120] 前記一般式（17)において、 Ar、 Arで各々表されるァリーレン基は、前記一般式（ In the general formula (17), the arylene groups represented by Ar and Ar each have the general formula (
1 2  1 2
16)において Ar、 Arで各々表されるァリーレン基と同義である。 Ar、 Arで各々表  In 16), these are synonymous with the arylene groups represented by Ar and Ar, respectively. Ar and Ar respectively
1 2 1 2 される芳香族複素環基は、前記一般式（16)において Ar、 Arで各々表される 2価の  The aromatic heterocyclic group represented by 1 2 1 2 is a divalent group represented by Ar or Ar in the general formula (16).
1 2  1 2
芳香族複素環基と同義である。  Synonymous with aromatic heterocyclic group.
[0121] Z、 Z、 Z、 Zで各々表される、各々窒素原子を少なくとも一つ含む 6員の芳香族 [0121] A six-membered aromatic group each containing at least one nitrogen atom represented by Z, Z, Z, or Z
1 2 3 4  1 2 3 4
複素環としては、例えば、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環等が挙 げられる。  Examples of the heterocyclic ring include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
[0122] Lで表される 2価の連結基としては、前記一般式（10)において、 Lで表される 2価  [0122] Examples of the divalent linking group represented by L include the divalent group represented by L in the general formula (10).
1  1
の連結基と同義である力 好ましくはアルキレン基、 o s—等のカルコゲン原 子を含む 2価の基であり、最も好ましくはアルキレン基である。 A force that is synonymous with the linking group of It is a divalent group containing a child, and is most preferably an alkylene group.
[0123] 以下に、本発明に係る一般式（1)で表される化合物の具体例を示すが、本発明は これらに限定されない。 [0123] Specific examples of the compound represented by the general formula (1) according to the present invention are shown below, but the present invention is not limited thereto.
[0124] [化 28] [0124] [Chemical 28]
Figure imgf000032_0001
Figure imgf000032_0001
[0125] [化 29] [0S^ ] [92 TO] [0125] [Chemical 29] [0S ^] [92 TO]
Figure imgf000033_0001
Figure imgf000033_0001
i.98lO/SOOZdf/13d 0W£f"0/900Z OAV i.98lO / SOOZdf / 13d 0W £ f "0 / 900Z OAV
Figure imgf000034_0001
Figure imgf000034_0001
[0127] [化 31] [Z ^] [82 TO] [0127] [Chemical 31] [Z ^] [82 TO]
Figure imgf000035_0001
Figure imgf000035_0001
Z.98lO/SOOZdf/X3d 88 0/900Z OAV 化合物 中心骨格 Z.98lO / SOOZdf / X3d 88 0 / 900Z OAV Compound Central skeleton
Figure imgf000036_0001
3] 化合物 中心骨格 A
Figure imgf000036_0001
3] Compound Central skeleton A
Figure imgf000037_0001
4]
Figure imgf000037_0001
Four]
Figure imgf000038_0001
Figure imgf000038_0001
[0131] [化 35] [0131] [Chemical 35]
Figure imgf000039_0001
Figure imgf000039_0001
[0132] [化 36]
Figure imgf000040_0001
[0132] [Chem 36]
Figure imgf000040_0001
Figure imgf000040_0002
Figure imgf000040_0003
Figure imgf000040_0002
Figure imgf000040_0003
[0133] [化 37] [0133] [Chemical 37]
Figure imgf000041_0001
Figure imgf000041_0001
[0134] [化 38] [0134] [Chemical 38]
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000042_0003
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000042_0003
[0135] [化 39] [0135] [Chemical 39]
Figure imgf000043_0001
Figure imgf000043_0001
[0136] [化 40] [0136] [Chemical 40]
Figure imgf000044_0001
Figure imgf000044_0001
H,C CH2 H, C CH 2
\ I\ I
H2C- CH2 H 2 C- CH 2
[0137] [化 41] [0137] [Chemical 41]
Figure imgf000045_0001
Figure imgf000045_0001
[0138] [化 42] [0138] [Chemical 42]
Figure imgf000046_0001
Figure imgf000046_0001
[0139] [化 43] [0139] [Chemical 43]
Figure imgf000047_0001
Figure imgf000047_0001
[0140] [化 44] [m [mo] [0140] [Chemical 44] [m [mo]
Figure imgf000048_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000049_0001
Figure imgf000049_0002
Figure imgf000049_0002
[0142] [化 46] [0142] [Chem 46]
Figure imgf000050_0001
Figure imgf000050_0001
[0143] [化 47] [0143] [Chemical 47]
Figure imgf000051_0001
Figure imgf000051_0001
[0144] [化 48] [0144] [Chemical 48]
Figure imgf000052_0001
Figure imgf000052_0001
[0145] [化 49] [oe ] [9W0] [0145] [Chemical 49] [oe] [9W0]
Figure imgf000053_0001
[TS^ ] [ ΐθ]
Figure imgf000053_0001
[TS ^] [ΐθ]
Figure imgf000054_0001
[2S ] [8W0]
Figure imgf000054_0001
[2S] [8W0]
Figure imgf000055_0001
l [6 0]
Figure imgf000055_0001
l [6 0]
Figure imgf000056_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000057_0001
Figure imgf000057_0002
Figure imgf000057_0002
[0150] [化 54] [0150] [Chemical 54]
Figure imgf000058_0001
Figure imgf000058_0002
Figure imgf000058_0003
Figure imgf000058_0004
Figure imgf000058_0001
Figure imgf000058_0002
Figure imgf000058_0003
Figure imgf000058_0004
[0151] [化 55] 147 [0151] [Chemical 55] 147
Figure imgf000059_0001
Figure imgf000059_0001
6] 6]
Figure imgf000060_0001
Figure imgf000060_0001
Figure imgf000060_0002
Figure imgf000060_0002
[0153] [化 57] [0153] [Chemical 57]
Figure imgf000061_0001
Figure imgf000061_0001
[0154] [化 58] 158 159
Figure imgf000062_0001
[0154] [Chemical 58] 158 159
Figure imgf000062_0001
Figure imgf000062_0002
Figure imgf000062_0002
9] 9]
Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0003
Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0003
[0156] [化 60] 170 [0156] [Chemical 60] 170
Figure imgf000064_0001
1]
Figure imgf000064_0001
1]
[29^ ] [83 TO] [29 ^] [83 TO]
Figure imgf000065_0001
Figure imgf000065_0001
l.98I0/S00Zdf/13d ε9 l.98I0 / S00Zdf / 13d ε9
Figure imgf000066_0001
Figure imgf000066_0001
Figure imgf000066_0002
Figure imgf000066_0002
以下に本発明に係る化合物の代表的な合成例を示すが、本発明はこれらに限定さ れない。 [0160] 《例示化合物 73の合成》 Although the typical synthesis example of the compound concerning this invention is shown below, this invention is not limited to these. [0160] <Synthesis of Exemplified Compound 73>
[0161] [化 63] [0161] [Chemical 63]
Figure imgf000067_0001
Figure imgf000067_0001
[0162] 4, 4' —ジョードビフエ-ル 6. 87g、 β—カルボリン 6. OOgを Ν, N—ジメチルァセ トアミド 50ml中に添加した混合液に、銅粉 4. 5g、炭酸カリウム 7. 36gをカ卩え、 15時 間加熱還流した。放冷後水クロ口ホルムを加え、不溶物を濾去した。有機層を分離し 、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣を酢酸に溶解し、活 性炭処理後、再結晶して，例示化合物 73の無色結晶 4. 2gを得た。 [0162] 4, 4 '— Jodhbi-Fell 6.87 g, β-carboline 6. OOg in 50 ml of N, N-dimethylacetamide, 4.5 g of copper powder and 7.36 g of potassium carbonate were added. It was heated and refluxed for 15 hours. After standing to cool, water-cold form was added and insolubles were removed by filtration. The organic layer was separated, washed with water and saturated brine, and concentrated under reduced pressure. The obtained residue was dissolved in acetic acid, treated with activated charcoal, and recrystallized to give colorless crystals of Exemplified Compound 73 4 2g was obtained.
[0163] 例示化合物 73の構造は1 H—NMR ^ベクトル及び質量分析スペクトルによって確 認した。例示化合物 73の物性データ、スペクトルデータを下記に示す。 [0163] The structure of Exemplified Compound 73 was confirmed by 1 H-NMR ^ vector and mass spectrometry spectrum. The physical property data and spectrum data of Exemplified Compound 73 are shown below.
[0164] 無色結晶、融点 200°C  [0164] Colorless crystals, melting point 200 ° C
MS (FAB) m/z： 487 (M+ 1)  MS (FAB) m / z: 487 (M + 1)
'H-NMR (400MHz, CDC1 )： δ /ppm 7. 3— 7. 5 (m、2H)、 7. 5— 7. 6 (  'H-NMR (400MHz, CDC1): δ / ppm 7.3—7.5 (m, 2H), 7.5—7.6 (
3  Three
m, 4H)、 7. 7- 7. 8 (m, 4H)、 7. 9— 8. 0 (m, 4H)、 8. 06 (d, J= 5. 1Hz, 2H) 、 8. 24 (d, J = 7. 8Hz, 2H)、 8. 56 (d, J = 5. 1Hz, 2H)、 8. 96 (s, 2H) 《例示化合物 74の合成》  m, 4H), 7. 7- 7.8 (m, 4H), 7.9—8.00 (m, 4H), 8.06 (d, J = 5.1 Hz, 2H), 8. 24 ( d, J = 7.8 Hz, 2H), 8.56 (d, J = 5.1 Hz, 2H), 8.96 (s, 2H) << Synthesis of Exemplified Compound 74 >>
[0165] [化 64] [0165] [Chemical 64]
Figure imgf000068_0001
Figure imgf000068_0001
Figure imgf000068_0002
Figure imgf000068_0002
[0166] 酢酸パラジウム 0. 32g、トリ— tert ブチルホスフィン 1. 17gを無水トルエン 10ml に溶解し、水素化ホウ素ナトリウム 50mgを添加し、室温で 10分間攪拌した後、 δ - カルボリン 5. OOg、 4, 4' ージョードビフエ-ル 5. 87g、ナトリウム tert ブトキシ ド 3.42gを無水キシレン 50ml中に分散し、窒素雰囲気下、還流温度にて 10時間撹 拌した。得られた反応混合物を放冷後クロ口ホルムと水を加えて有機層を分離し、有 機層を、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣をテトラヒドロ フランに溶解し、活性炭処理を施した後、再結晶して例示化合物 74の無色結晶 5. 0 gを得た。 [0166] Palladium acetate 0.32g, tri-tertbutylphosphine 1.17g dissolved in anhydrous toluene 10ml, sodium borohydride 50mg was added and stirred at room temperature for 10 minutes, then δ-carboline 5.OOg, 4 , 4′-Jordobiphal 5.87 g and sodium tert-butoxide 3.42 g were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. The resulting reaction mixture was allowed to cool and then added with chloroform and water to separate the organic layer. The organic layer was washed with water and saturated brine, and then concentrated under reduced pressure. It was dissolved in furan, treated with activated carbon, and recrystallized to obtain 5.0 g of colorless crystals of Exemplified Compound 74.
[0167] 例示化合物 74の構造は1 H— NMR ^ベクトル及び質量分析スペクトルによって確 認した。例示化合物 74の物性データ、スペクトルデータを下記に示す。 [0167] The structure of Exemplified Compound 74 was confirmed by 1 H-NMR ^ vector and mass spectrometry spectrum. The physical property data and spectrum data of Exemplified Compound 74 are shown below.
[0168] MS (FAB) m/z： 487 (M+ 1) [0168] MS (FAB) m / z: 487 (M + 1)
^H—NMR (400MHz, CDC1 )： δ /ppm 7. 37(dd, J=4. 7Hz, J = 8. 3Hz,  ^ H—NMR (400MHz, CDC1): δ / ppm 7.37 (dd, J = 4.7Hz, J = 8.3Hz,
3  Three
2H)、 7.4-7. 5(m, 2H)、 7. 5— 7. 6(m, 4H)、 7. 7— 7. 8(m, 4H)、 7. 81 (d d, J=l. 2Hz, J = 8. 3Hz, 2H)、 7. 9— 8. 0(m, 4H)、 8. 48(d, J = 7. 8Hz, 2 H), 8. 65 (dd, J=l. 2Hz, J=4. 6Hz, 2H)  2H), 7.4-7.5 (m, 2H), 7.5-7.6 (m, 4H), 7.7-7.7.8 (m, 4H), 7.81 (dd, J = l. 2Hz, J = 8.3Hz, 2H), 7.9-8.0 (m, 4H), 8.48 (d, J = 7.8Hz, 2H), 8.65 (dd, J = l. (2Hz, J = 4.6 Hz, 2H)
《例示化合物 60の合成》  << Synthesis of Exemplified Compound 60 >>
[0169] [化 65] [0169] [Chemical 65]
Figure imgf000069_0001
Figure imgf000069_0001
[0170] 4, 4' —ジョードビフエ-ル 6. 87g、 y—カルボリン 6. OOgを N, N ジメチルァセ トアミド 50ml中に添加した混合液に、銅粉 4. 5g、炭酸カリウム 7. 36gをカ卩え、 15時 間加熱還流した。放冷後水クロ口ホルムを加え、不溶物を濾去した。有機層を分離し 、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣をシリカゲルクロマト グラフィ一に付した後、ジクロロメタン Zシクロへキサン中で結晶化させ、例示化合物 60の無色結晶 4. 3gを得た。 [0170] 4, 4'—Jordobi-Fell 6.87g, y-carboline 6. To a mixture of OOg in 50ml of N, N dimethylacetamide, add 4.5g of copper powder and 7.36g of potassium carbonate. The mixture was heated to reflux for 15 hours. After standing to cool, water-cold form was added and insolubles were removed by filtration. The organic layer was separated, washed with water and saturated brine, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, crystallized in dichloromethane Z cyclohexane, and exemplified compound 60 There were obtained 4.3 g of colorless crystals.
[0171] 例示化合物 60の構造は、 NMR ^ベクトル及び質量分析スペクトルによって確 認した。例示化合物 60の物性データ、スペクトルデータを下記に示す。  [0171] The structure of Exemplified Compound 60 was confirmed by NMR ^ vector and mass spectrometry spectrum. The physical property data and spectrum data of Exemplified Compound 60 are shown below.
[0172] MS (FAB) m/z： 487 (M+ 1)  [0172] MS (FAB) m / z: 487 (M + 1)
'H-NMR (400MHz, CDC1 )： δ /ppm 7. 4— 7. 4 (m, 4H)、 7. 4— 7. 5 (  'H-NMR (400MHz, CDC1): δ / ppm 7.4—7.4 (m, 4H), 7.4—7.5 (
3  Three
m, 4H)、 7. 7- 7. 8 (m, 4H) 7. 9— 8. 0 (m, 4H)、 8. 25 (d, J = 7. 8Hz, 2H)、 8. 57 (d, J = 5. 6Hz, 2H)、 9. 42 (s, 1H)  m, 4H), 7. 7- 7.8 (m, 4H) 7.9—8.0 (m, 4H), 8.25 (d, J = 7.8Hz, 2H), 8.57 (d , J = 5.6Hz, 2H), 9.42 (s, 1H)
《例示化合物 144の合成》  << Synthesis of Exemplified Compound 144 >>
[0173] [化 66] [0173] [Chemical 66]
Figure imgf000070_0001
Figure imgf000070_0001
Figure imgf000070_0002
Figure imgf000070_0002
[0174] 酢酸パラジウム 0. 16g、トリ— tert—ブチルホスフィン 0. 58gを無水トルエン 10ml に溶解し、水素化ホウ素ナトリウム 25mgを添加し、室温で 10分間攪拌した後、 δ - カルボリン 2. OOg、中間体 a3. 20g、ナトリウム— tert—ブ卜キシド 1. 37gを無水キシ レン 50ml中に分散し、窒素雰囲気下、還流温度にて 10時間撹拌した。放冷後クロ口 ホルムと水を加えて有機層を分離し、有機層を水、飽和食塩水で洗浄した後減圧下 に濃縮し、得られた残渣を酢酸力も再結晶して例示化合物 144の無色結晶 1. 5gを 得た。 [0174] 0.16 g of palladium acetate and 0.58 g of tri-tert-butylphosphine were dissolved in 10 ml of anhydrous toluene, 25 mg of sodium borohydride was added, and the mixture was stirred at room temperature for 10 minutes. Then, δ-carboline 2.OOg, Intermediate a3. 20 g and sodium-tert-butoxide 1.37 g were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. After cooling, the organic layer is separated by adding chloroform and water, and the organic layer is washed with water and saturated brine and then concentrated under reduced pressure. 1.5 g of colorless crystals were obtained.
[0175] 例示化合物 144の構造は、 ^H— NMRスペクトル及び質量分析スペクトルによって 確認した。例示化合物 144のスペクトルデータは以下の通りである。  [0175] The structure of Exemplified Compound 144 was confirmed by ^ H-NMR spectrum and mass spectrometry spectrum. The spectrum data of Exemplified Compound 144 are as follows.
[0176] MS (FAB) m/z： 647 (M + 1) [0176] MS (FAB) m / z: 647 (M + 1)
'H-NMR (400MHz, CDC1 )： δ /ppm 1. 80 (S, 12H)、 7. 27 (S, 4H)、 7  'H-NMR (400MHz, CDC1): δ / ppm 1.80 (S, 12H), 7.27 (S, 4H), 7
3  Three
. 34 (dd, J=4. 9Hz, J = 8. 3Hz, 2H)、 7. 3— 7. 4 (m, 2H)、 7. 4— 7. 5 (m, 1 2H)、 7. 76 (dd, J= l. 3Hz, J = 8. 3Hz、 2H)、 8. 45 (d, J = 7. 8Hz, 2H)、 8. 6 3 (dd, J= l. 3Hz, J=4. 9Hz, 2H)  34 (dd, J = 4.9 Hz, J = 8.3 Hz, 2H), 7.3—7.4 (m, 2H), 7.4—7.5 (m, 1 2H), 7.76 (dd, J = l. 3Hz, J = 8.3Hz, 2H), 8.45 (d, J = 7.8Hz, 2H), 8.6 3 (dd, J = l. 3Hz, J = 4. (9Hz, 2H)
《例示化合物 143の合成》  << Synthesis of Exemplified Compound 143 >>
[0177] [化 67] [0177] [Chemical 67]
Figure imgf000071_0001
Figure imgf000071_0001
[0178] 4, 4' —ジクロ口一 3, 3' —ビビリジル 0. 85g、ジァミン bO. 59g、ジベンジリデン アセトンパラジウム 44mg、イミダゾリゥム塩 36mg、ナトリウム tert ブトキシド 1. 09 gをジメトキシェタン 5mlに添加し、 80°Cで 24時間加温攪拌した。放冷後クロ口ホルム と水を加えて有機層を分離し、有機層を水、飽和食塩水で洗浄した後減圧下に濃縮 し、得られた残渣を酢酸ェチルカ 再結晶して例示化合物 143の無色結晶 0. 3gを 得た。 [0178] 4, 4 '— Diclomental 1, 3' — Bibilidil 0.85 g, Diamine bO. 59 g, Dibenzylidene Acetonepalladium 44 mg, Imidazolium salt 36 mg, Sodium tert Butoxide 1.09 g added to 5 ml dimethoxyethane The mixture was heated and stirred at 80 ° C for 24 hours. After standing to cool, the organic layer is separated by adding chloroform and water, and the organic layer is washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue is recrystallized from ethyl acetate to recrystallize Exemplified Compound 143. 0.3 g of colorless crystals was obtained.
[0179] 例示化合物 143の構造は、 ^H—NMRスペクトル及び質量分析スペクトルによって 確認した。例示化合物 143のスペクトルデータを下記に示す。  [0179] The structure of Exemplified Compound 143 was confirmed by ^ H-NMR spectrum and mass spectrometry spectrum. The spectral data of Exemplified Compound 143 is shown below.
[0180] MS (FAB) m/z： 639 (M+ 1) [0180] MS (FAB) m / z: 639 (M + 1)
iH—NMR (400MHz, CDC1 )： δ /ppm 7. 46 (d, J = 5. 7Hz, 4H)、 7. 6—  iH—NMR (400MHz, CDC1): δ / ppm 7.46 (d, J = 5.7Hz, 4H), 7. 6—
3  Three
7. 7 (m, 4H)、 7. 8— 7. 9 (m, 4H)、 8. 67 (d, J = 5. 7Hz, 4H)、 9. 51 (S, 4H) 《例示化合物 145の合成》  7. 7 (m, 4H), 7.8—7.9 (m, 4H), 8.67 (d, J = 5.7 Hz, 4H), 9.51 (S, 4H) << Example Compound 145 Synthesis
例示化合物 143の合成において、 4, 4' ージクロロー 3, 3' —ビビリジルの一方 のピリジン環をベンゼンに変更した、 3—（2 クロ口フエ二ノレ）ー4 クロ口ピリジンを 用いた以外は同様にして、例示化合物 145を合成した。  In the synthesis of Exemplified Compound 143, except that one of the pyridine rings of 4,4'-dichloro-3,3'-bibilidyl was changed to benzene, and 3- (2 chlorophenol) -4 chloropyridine was used. Thus, Exemplified Compound 145 was synthesized.
[0181] 例示化合物 145の構造は、 ^H—NMRスペクトル及び質量分析スペクトルによって 確認した。例示化合物 145のスペクトルデータを下記に示す。  [0181] The structure of Exemplified Compound 145 was confirmed by ^ H-NMR spectrum and mass spectrometry spectrum. The spectral data of Exemplified Compound 145 is shown below.
[0182] MS (FAB) m/z： 637 (M+ 1) 'H-NMR (400MHz, CDC1 )： δ /ppm 7. 3— 7. 4 (m, 2H)、 7. 6— 7. 7 ( [0182] MS (FAB) m / z: 637 (M + 1) 'H-NMR (400MHz, CDC1): δ / ppm 7.3—7.4 (m, 2H), 7.6—7.7 (
3  Three
m, 4H)、 7. 7- 7. 8 (m, 4H) 7. 8— 7. 9 (m, 4H)、 8. 06 (d, J = 5. 3Hz, 2H)、 8. 23 (d, J = 7. 8Hz, 2H)、8. 56 (d, J = 5. 3Hz, 2H) , 8. 96 (S, 2H)  m, 4H), 7. 7- 7.8 (m, 4H) 7.8—7.9 (m, 4H), 8.06 (d, J = 5.3 Hz, 2H), 8.23 (d , J = 7.8Hz, 2H), 8.56 (d, J = 5.3Hz, 2H), 8.96 (S, 2H)
なお、上記の合成例以外に、これらの化合物のァザカルバゾール環やその類緑体 ίま、 J. Chem. Soc. , Perkin Trans. 1, 1505— 1510 (1999)、 Pol. J. Chem. , 54, 1585 (1980)、 (Tetrahedron  In addition to the above synthesis examples, the azacarbazole ring of these compounds and their chloroplasts, J. Chem. Soc., Perkin Trans. 1, 1505-1510 (1999), Pol. J. Chem. , 54, 1585 (1980), (Tetrahedron
Lett. 41 (2000) , 481— 484)に記載される合成法に従って合成することができる 。合成されたァザカルバゾール環やその類緑体と、芳香環、複素環、アルキル基など の、コア、連結基への導入は、ウルマンカップリング、 Pd触媒を用いたカップリング、 スズキカップリングなど公知の方法を用いることができる。  Lett. 41 (2000), 481-484). Introduction of the synthesized azacarbazole ring or its chloroplast to the core or linking group of aromatic ring, heterocyclic ring, alkyl group, etc., Ullman coupling, coupling using Pd catalyst, Suzuki coupling, etc. A known method can be used.
[0183] 本発明に係る一般式（1)で表される化合物は分子量力 00以上であることが好まし ぐ 450以上であることがより好ましぐ更に好ましくは 600以上であり、特に好ましくは 分子量が 800以上である。これによりガラス転移温度を上昇させ熱安定性が向上し、 より一層長寿命化をさせることができる。  [0183] The compound represented by the general formula (1) according to the present invention preferably has a molecular weight of 00 or more, more preferably 450 or more, further preferably 600 or more, and particularly preferably. The molecular weight is 800 or more. As a result, the glass transition temperature is raised, the thermal stability is improved, and the life can be further extended.
[0184] 本発明に係る一般式（1)で表される化合物は、各々有機 EL素子用材料 (バックラ イト、フラットパネルディスプレイ、照明光源、表示素子、電子写真用光源、記録光源 、露光光源、読み取り光源、標識、看板、インテリア、光通信デバイスなど)等の用途 に用いられるが、その他の用途しては、有機半導体レーザ用材料 (記録光源、露光 光源、読み取り光源光通信デバイス、電子写真用光源など)、電子写真用感光体材 料、有機 TFT素子用材料 (有機メモリ素子、有機演算素子、有機スイッチング素子） 、有機波長変換素子用材料、光電変換素子用材料 (太陽電池、光センサーなど)な どの広い分野に利用可能である。  [0184] The compound represented by the general formula (1) according to the present invention is a compound for an organic EL element (backlight, flat panel display, illumination light source, display element, electrophotographic light source, recording light source, exposure light source, Used for applications such as reading light sources, signs, signboards, interiors, optical communication devices, etc., but other uses include materials for organic semiconductor lasers (recording light sources, exposure light sources, reading light source optical communication devices, for electrophotography) Light source, etc.), electrophotographic photosensitive material, organic TFT element material (organic memory element, organic arithmetic element, organic switching element), organic wavelength conversion element material, photoelectric conversion element material (solar cell, photosensor, etc.) ) And can be used in a wide range of fields.
[0185] 次に、本発明の有機 EL素子の構成層について詳細に説明する。本発明において 、有機 EL素子の層構成の好ましい具体例を以下に示すが、本発明はこれらに限定 されない。  Next, the constituent layers of the organic EL element of the present invention will be described in detail. In the present invention, preferred specific examples of the layer structure of the organic EL element are shown below, but the present invention is not limited thereto.
[0186] (i)陽極 Z発光層 Z電子輸送層 Z陰極  [0186] (i) Anode Z light emitting layer Z electron transport layer Z cathode
(ii)陽極 Z正孔輸送層 Z発光層 Z電子輸送層 Z陰極  (ii) Anode Z hole transport layer Z light emitting layer Z electron transport layer Z cathode
(iii)陽極 Z正孔輸送層 Z発光層 Z正孔阻止層 Z電子輸送層 Z陰極 (iv)陽極 z正孔輸送層 z発光層 z正孔阻止層 z電子輸送層 z陰極バッファ一層(iii) Anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z cathode (iv) Anode z Hole transport layer z Light emitting layer z Hole blocking layer z Electron transport layer z Cathode buffer layer
Z陰極 Z cathode
(v)陽極 Z陽極バッファ一層 Z正孔輸送層 Z発光層 Z正孔阻止層 Z電子輸送層 Z陰極バッファ一層 Z陰極  (v) Anode Z anode buffer layer Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer layer Z cathode
なお、正孔輸送層は陽極に隣接し、電子輸送層は陰極に隣接していることが好まし い。  The hole transport layer is preferably adjacent to the anode, and the electron transport layer is preferably adjacent to the cathode.
[0187] 《陽極》  [0187] 《Anode》
有機 EL素子における陽極としては、仕事関数の大きい (4eV以上)金属、合金、電 気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。こ のような電極物質の具体例としては Au等の金属、 Cul、インジウムチンォキシド (ITO ) , SnO、 ZnO等の導電性透明材料が挙げられる。また、 IDIXO (In O— ZnO)等 As the anode in the organic EL device, an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, conductive transparent materials such as Cul, indium tinoxide (ITO), SnO, and ZnO. IDIXO (In O—ZnO) etc.
2 2 3 非晶質で透明導電膜を作製可能な材料を用いてもょ ヽ。陽極はこれらの電極物質を 蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィ一法で所望 の形状のパターンを形成してもよぐあるいはパターン精度をあまり必要としない場合 は（100 μ m以上程度）、上記電極物質の蒸着やスパッタリング時に所望の形状のマ スクを介してパターンを形成してもよい。この陽極より発光を取り出す場合には、透過 率を 10%より大きくすることが望ましぐまた陽極としてのシート抵抗は数百 Ω Zロ以 下が好ましい。更に膜厚は材料にもよる力 通常 10〜： L000nm、好ましくは 10〜20 Onmの範囲で選ばれる。 2 2 3 Use an amorphous material that can produce a transparent conductive film. For the anode, these electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by a single photolithography method. m or more), a pattern may be formed through a mask of a desired shape during the deposition or sputtering of the electrode material. In the case of taking out light emission from this anode, it is desirable to make the transmittance larger than 10%, and the sheet resistance as the anode is preferably several hundred ΩZ or less. Further, the film thickness is a force depending on the material. Usually 10 to: L000 nm, preferably 10 to 20 Onm.
[0188] 《陰極》 [0188] 《Cathode》
一方、陰極としては、仕事関数の小さい (4eV以下)金属 (電子注入性金属と称する )、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる 。このような電極物質の具体例としては、ナトリウム、ナトリウム一カリウム合金、マグネ シゥム、リチウム、マグネシウム Z銅混合物、マグネシウム Z銀混合物、マグネシウム Zアルミニウム混合物、マグネシウム Zインジウム混合物、アルミニウム Z酸ィ匕アルミ -ゥム (Al O )  On the other hand, a cathode having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum Um (Al O)
2 3混合物、インジウム、リチウム Zアルミニウム混合物、希土類金属等が 挙げられる。これらの中で、電子注入性及び酸ィ匕等に対する耐久性の点から、電子 注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物 、例えば、マグネシウム Z銀混合物、マグネシウム Zアルミニウム混合物、マグネシゥ ム Zインジウム混合物、アルミニウム Z酸ィ匕アルミニウム (Ai 2 o 3 )混合物、リチウム Z アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着 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。 また、陰極としてのシート抵抗は数百 Ω /口以下が好ましぐ膜厚は通常 ΙΟηπ！〜 5 μ m、好ましくは 50〜200nmの範囲で選ばれる。なお、発光した光を透過させるた め、有機 EL素子の陽極または陰極のいずれか一方力 透明または半透明であれば 発光輝度が向上し好都合である。 2 3 Mixture, indium, lithium Z aluminum mixture, rare earth metal, etc. Among these, a mixture of an electron injecting metal and a second metal, which is a stable metal having a larger work function value than this, from the viewpoint of electron injecting properties and durability against acids, etc. For example, a magnesium Z silver mixture, a magnesium Z aluminum mixture, a magnesium Z indium mixture, an aluminum Z acid aluminum (Ai 2 o 3) mixture, a lithium Z aluminum mixture, aluminum and the like are suitable. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Also, the sheet resistance as a cathode is several hundred Ω / mouth or less, and the preferred film thickness is usually ΙΟηπ! ˜5 μm, preferably selected in the range of 50 to 200 nm. In addition, since the emitted light is transmitted, it is convenient that either the anode or the cathode of the organic EL element is transparent or semi-transparent to improve the emission luminance.
[0189] また、陰極に上記金属を l〜20nmの膜厚で作製した後に、陽極の説明で挙げた 導電性透明材料をその上に作製することで、透明または半透明の陰極を作製するこ とができ、これを応用することで陽極と陰極の両方が透過性を有する素子を作製する ことができる。 [0189] Further, after the metal is formed to a thickness of 1 to 20 nm on the cathode, the transparent conductive material described in the description of the anode is formed thereon, whereby a transparent or translucent cathode is manufactured. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
[0190] 次に、本発明の有機 EL素子の構成層として用いられる、注入層、阻止層、電子輸 送層等について説明する。  Next, an injection layer, a blocking layer, an electron transport layer, and the like used as a constituent layer of the organic EL element of the present invention will be described.
[0191] 《注入層：電子注入層、正孔注入層》 [0191] <Injection layer: electron injection layer, hole injection layer>
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記の如く陽極と 発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在 させてちょい。  The injection layer is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. Hey.
[0192] 注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる 層のことで、「有機 EL素子とその工業化最前線（ 1998年 11月 30日ェヌ'ティー ·ェ ス社発行)」の第 2編第 2章「電極材料」（123〜166頁）に詳細に記載されており、正 孔注入層（陽極バッファ一層）と電子注入層（陰極バッファ一層）とがある。  [0192] The injection layer is a layer provided between the electrode and the organic layer in order to lower the driving voltage and improve the luminance of the light emission. “The organic EL element and the forefront of industrialization (November 30, 1998) (Published by ES Co., Ltd.) ”, Chapter 2“ Chapter 2 Electrode Materials ”(pages 123-166) in detail, the hole injection layer (anode buffer layer) and electron injection layer (cathode buffer layer) There is.
[0193] 陽極バッファ一層（正孔注入層）は、特開平 9— 45479号公報、同 9 260062号 公報、同 8— 288069号公報等にもその詳細が記載されており、具体例として、銅フ タロシアニンに代表されるフタロシアニンバッファ一層、酸ィ匕バナジウムに代表される 酸化物バッファ一層、アモルファスカーボンバッファ一層、ポリア-リン（ェメラルディ ン)やポリチォフェン等の導電性高分子を用いた高分子バッファ一層等が挙げられる [0194] 陰極バッファ一層（電子注入層）は、特開平 6— 325871号公報、同 9— 17574号 公報、同 10— 74586号公報等にもその詳細が記載されており、具体的にはストロン チウムゃアルミニウム等に代表される金属バッファ一層、フッ化リチウムに代表される アルカリ金属化合物バッファ一層、フッ化マグネシウムに代表されるアルカリ土類金 属化合物バッファ一層、酸ィヒアルミニウムに代表される酸ィヒ物バッファ一層等が挙げ られる。上記バッファ一層（注入層）はごく薄い膜であることが望ましぐ素材にもよる がその膜厚は 0. lnm〜5 mの範囲が好ましい。 [0193] The details of the anode buffer layer (hole injection layer) are also described in JP-A-9-45479, JP-A-9260062, JP-A-8-288069 and the like. A phthalocyanine buffer layer typified by phthalocyanine, an oxide buffer layer typified by vanadium oxide, an amorphous carbon buffer layer, a polymer buffer layer using a conductive polymer such as polyarene (emeraldine) or polythiophene Etc. [0194] The details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Metal buffer layer typified by aluminum or titanium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, acid typified by acid aluminum One thing buffer. The buffer layer (injection layer) is preferably a very thin film, although the film thickness is preferably in the range of 0.1 nm to 5 m, although it depends on the desired material.
[0195] 《阻止層：正孔阻止層、電子阻止層》  [0195] <Blocking layer: hole blocking layer, electron blocking layer>
阻止層は、上記の如ぐ有機化合物薄膜の基本構成層の他に必要に応じて設けら れるものである。例えば、特開平 11 204258号公報、同 11— 204359号公報、及 び「有機 EL素子とその工業化最前線（ 1998年 11月 30日ェヌ'ティー ·エス社発行） 」の 237頁等に記載されて 、る正孔阻止（ホールブロック）層がある。  The blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A-11 204258, 11-204359, and “Organic EL device and the forefront of its industrialization” (published by NTS Corporation on November 30, 1998). There is a hole blocking layer.
[0196] 正孔阻止層とは広い意味では電子輸送層であり、電子を輸送する機能を有しつつ 正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔 を阻止することで電子と正孔の再結合確率を向上させることができる。  [0196] The hole blocking layer is an electron transporting layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
[0197] 本発明の有機 EL素子の正孔阻止層は、発光層に隣接して設けられている。  [0197] The hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.
[0198] 本発明では、正孔阻止層の正孔阻止材料として前述した本発明に係る化合物を含 有させることが好ましい。これにより、より一層発光効率の高い有機 EL素子とすること ができる。更により一層長寿命化させることができる。  [0198] In the present invention, the above-described compound according to the present invention is preferably contained as a hole blocking material of the hole blocking layer. As a result, an organic EL device with even higher luminous efficiency can be obtained. Further, the lifetime can be further increased.
[0199] 一方、電子阻止層とは広い意味では正孔輸送層であり、正孔を輸送する機能を有 しつつ電子を輸送する能力が著しく小さい材料力 なり、正孔を輸送しつつ電子を阻 止することで電子と正孔の再結合確率を向上させることができる。  [0199] On the other hand, the electron blocking layer is a hole transport layer in a broad sense, and has a material force that has a function of transporting holes while transporting electrons, and is capable of transporting electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
[0200] 《発光層》  [0200] 《Light emitting layer》
本発明に係る発光層は、電極または電子輸送層、正孔輸送層カゝら注入されてくる 電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であつ ても発光層と隣接層との界面であってもよ 、。  The light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from an electrode, an electron transport layer, or a hole transport layer, and the light emitting portion is within the layer of the light emitting layer. It may be the interface between the light emitting layer and the adjacent layer.
[0201] (ホストイ匕合物） [0201] (Hosty compound)
本発明の有機 EL素子の発光層には、以下に示す、ホストイ匕合物とリン光性ィ匕合物 (リン光発光性ィ匕合物ともいう）が含有されることが好ましぐ本発明においては、ホス ト化合物として前述した本発明に係る化合物を用いることが好ましい。これにより、より 一層発光効率を高くすることができる。また、ホストイ匕合物として、上記の本発明に係 る化合物以外の化合物を含有してもよ ヽ。 The light emitting layer of the organic EL device of the present invention includes the following host compound and phosphorescent compound. In the present invention in which it is preferable to contain (also referred to as phosphorescent compound), it is preferable to use the compound according to the present invention described above as the host compound. As a result, the luminous efficiency can be further increased. Further, the host compound may contain a compound other than the compound according to the present invention.
[0202] ここで、本発明においてホストイ匕合物とは、発光層に含有される化合物の内で室温  [0202] Here, in the present invention, the host compound is a room temperature among the compounds contained in the light emitting layer.
(25°C)においてリン光発光のリン光量子収率が、 0. 01未満の化合物と定義される。  A phosphorescence quantum yield of phosphorescence emission at (25 ° C) is defined as a compound having a concentration of less than 0.01.
[0203] 更に公知のホストイ匕合物を複数種併用して用いてもよい。ホスト化合物を複数種用 いることで、電荷の移動を調整することが可能であり、有機 EL素子を高効率化するこ とができる。また、リン光性ィ匕合物を複数種用いることで、異なる発光を混ぜることが 可能となり、これにより任意の発光色を得ることができる。リン光性化合物の種類、ド 一プ量を調整することで白色発光が可能であり、照明、バックライトへの応用もできる  [0203] Further, a plurality of known host compounds may be used in combination. By using multiple types of host compounds, it is possible to adjust the movement of charges, and the organic EL device can be made highly efficient. In addition, by using a plurality of phosphorescent compounds, it is possible to mix different light emission, thereby obtaining an arbitrary emission color. White light emission is possible by adjusting the type and amount of phosphorescent compound, and it can also be used for lighting and backlighting.
[0204] これらの公知のホスト化合物としては、正孔輸送能、電子輸送能を有しつつ、且つ 発光の長波長化を防ぎ、なお且つ高 Tg (ガラス転移温度)である化合物が好ま 、。 [0204] As these known host compounds, a compound having a hole transporting ability and an electron transporting ability, which prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
[0205] 公知のホストイ匕合物の具体例としては、以下の文献に記載されている化合物が挙 げられる。  [0205] Specific examples of known host compound compounds include compounds described in the following documents.
[0206] 特開 2001— 257076号公報、同 2002— 308855号公報、同 2001— 313179号 公報、同 2002— 319491号公報、同 2001— 357977号公報、同 2002— 334786 号公報、同 2002— 8860号公報、同 2002— 334787号公報、同 2002— 15871号 公報、同 2002— 334788号公報、同 2002— 43056号公報、同 2002— 334789 号公報、同 2002— 75645号公報、同 2002— 338579号公報、同 2002— 10544 5号公報、同 2002— 343568号公報、同 2002— 141173号公報、同 2002— 352 957号公報、同 2002— 203683号公報、同 2002— 363227号公報、同 2002— 2 31453号公報、同 2003— 3165号公報、同 2002— 234888号公報、同 2003— 2 7048号公報、同 2002— 255934号公報、同 2002— 260861号公報、同 2002— 280183号公報、同 2002— 299060号公報、同 2002— 302516号公報、同 2002 — 305083号公報、同 2002— 305084号公報、同 2002— 308837号公報等。  [0206] JP 2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357977, 2002-334786, 2002-8860 No., 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579 Gazette, 2002-10544-5, 2002-343568, 2002-141173, 2002-352 957, 2002-203683, 2002-363227, 2002-2 31453, 2003-3165, 2002-234888, 2003-2 7048, 2002-255934, 2002-260861, 2002-280183, 2002- No. 299060, No. 2002-302516, No. 2002-305083, No. 2002-305084, No. 2002-308837, etc.
[0207] また、発光層はホストイ匕合物として更に蛍光極大波長を有するホストイ匕合物を含有 していてもよい。この場合、他のホスト化合物とリン光性化合物から蛍光性化合物へ のエネルギー移動で、有機 EL素子としての電界発光は蛍光極大波長を有する他の ホストィヒ合物からの発光も得られる。蛍光極大波長を有するホストィヒ合物として好まし いのは、溶液状態で蛍光量子収率が高いものである。ここで、蛍光量子収率は 10% 以上、特に 30%以上が好ましい。具体的な蛍光極大波長を有するホスト化合物とし ては、クマリン系色素、ピラン系色素、シァニン系色素、クロコニゥム系色素、スクァリ ゥム系色素、ォキソベンツアントラセン系色素、フルォレセイン系色素、ローダミン系 色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチォフェン系色素 等が挙げられる。蛍光量子収率は、前記第 4版実験化学講座 7の分光 IIの 362頁（1 992年版、丸善）に記載の方法により測定することができる。 [0207] The light emitting layer further contains a host compound having a fluorescence maximum wavelength as the host compound. You may do it. In this case, the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows electroluminescence as an organic EL device to be emitted from other host compounds having the maximum fluorescence wavelength. What is preferable as a host compound having a fluorescence maximum wavelength is one having a high fluorescence quantum yield in a solution state. Here, the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more. Specific host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squame dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like. The fluorescence quantum yield can be measured by the method described in the third edition of Experimental Chemistry Course 7, Spectroscopy II, page 362 (1992 edition, Maruzen).
[0208] (リン光性化合物（リン光発光性化合物) )  [0208] (Phosphorescent Compound (Phosphorescent Compound))
発光層に使用される材料 (以下、発光材料という）としては、上記のホスト化合物を 含有すると同時に、リン光性ィ匕合物を含有することが好ましい。これにより、より発光 効率の高!、有機 EL素子とすることができる。  The material used for the light emitting layer (hereinafter referred to as the light emitting material) preferably contains the above-mentioned host compound and at the same time contains a phosphorescent compound. As a result, an organic EL element with higher luminous efficiency can be obtained.
[0209] 本発明に係るリン光性ィ匕合物は、励起三重項力もの発光が観測される化合物であ り、室温（25°C)にてリン光発光する化合物であり、リン光量子収率が、 25°Cにおいて 0. 01以上の化合物である。リン光量子収率は好ましくは 0. 1以上である。上記リン 光量子収率は、第 4版実験化学講座 7の分光 IIの 398頁（1992年版、丸善）に記載 の方法により測定できる。溶液中でのリン光量子収率は種々の溶媒を用いて測定で きるが、本発明に用いられるリン光性ィ匕合物は、任意の溶媒のいずれかにおいて上 記リン光量子収率が達成されればよい。  [0209] The phosphorescent compound according to the present invention is a compound in which light emission with an excited triplet force is observed, and is a compound that emits phosphorescence at room temperature (25 ° C). A compound having a rate of 0.01 or more at 25 ° C. The phosphorescence quantum yield is preferably 0.1 or more. The phosphorescent quantum yield can be measured by the method described in Spectra II, page 398 (1992 edition, Maruzen) of 4th edition, Experimental Chemistry Course 7. The phosphorescence quantum yield in a solution can be measured using various solvents, but the phosphorescent compound used in the present invention achieves the above phosphorescence quantum yield in any solvent. Just do it.
[0210] リン光性ィ匕合物の発光は原理としては 2種挙げられ、一つはキャリアが輸送されるホ ストィ匕合物上でキャリアの再結合が起こってホストイ匕合物の励起状態が生成し、この エネルギーをリン光性ィ匕合物に移動させることでリン光性ィ匕合物力 の発光を得ると いうエネルギー移動型、もう一つはリン光性ィ匕合物がキャリアトラップとなり、リン光性 化合物上でキャリアの再結合が起こりリン光性ィ匕合物力もの発光が得られるというキ ャリアトラップ型であるが、いずれの場合においても、リン光性化合物の励起状態の エネルギーはホストイ匕合物の励起状態のエネルギーよりも低いことが条件である。 [0211] リン光性ィ匕合物は、有機 EL素子の発光層に使用される公知のものの中から適宜選 択して用いることができる。 [0210] There are two types of luminescence of phosphorescent compounds, one of which is the excited state of the host compound due to carrier recombination on the host compound to which carriers are transported. The energy transfer type is to obtain light emission of phosphorescent compound force by transferring this energy to the phosphorescent compound, and the other is that the phosphorescent compound is a carrier trap. This is a carrier trap type in which recombination of carriers occurs on the phosphorescent compound and light emission of a phosphorescent compound power is obtained. In either case, the excited state energy of the phosphorescent compound is The condition is that the energy is lower than the excited state energy of the host compound. [0211] The phosphorescent compound can be appropriately selected from known materials used for the light-emitting layer of the organic EL device.
[0212] 本発明で用いられるリン光性ィ匕合物としては、好ましくは元素の周期表で 8族〜 10 族の金属を含有する錯体系化合物であり、更に好ましくはイリジウム化合物、ォスミゥ ム化合物、または白金化合物（白金錯体系化合物）、希土類錯体であり、中でも最も 好まし 、のはイリジウム化合物である。 [0212] The phosphorescent compound used in the present invention is preferably a complex compound containing a group 8 to group 10 metal in the periodic table of elements, more preferably an iridium compound or an osmium compound. Or a platinum compound (platinum complex compound) or a rare earth complex, and most preferred is an iridium compound.
[0213] 以下に、リン光性化合物の具体例を示すが、本発明はこれらに限定されない。これ らの化合物は、例えば、 Inorg. Chem. 40卷、 1704〜1711に記載の方法等により 合成できる。 [0213] Specific examples of the phosphorescent compound are shown below, but the present invention is not limited thereto. These compounds can be synthesized, for example, by the method described in Inorg. Chem. 40 卷, 1704-1711.
[0214] [化 68] [0214] [Chemical 68]
Figure imgf000079_0001
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[0215] [化 69] [0Ζ^ ] [9 ISO]
Figure imgf000080_0001
[0215] [Chem 69] [0Ζ ^] [9 ISO]
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Figure imgf000081_0001
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[0217] [化 71] [0217] [Chemical 71]
Figure imgf000081_0002
Figure imgf000081_0002
[0218] [化 72] [0218] [Chemical 72]
Rh-1 Rh-2 Rh-3
Figure imgf000081_0003
Rh-1 Rh-2 Rh-3
Figure imgf000081_0003
[0219] [化 73] [0219] [Chemical 73]
Figure imgf000082_0001
Figure imgf000082_0001
Figure imgf000082_0002
Figure imgf000082_0002
本発明においては、リン光性ィ匕合物のリン光発光極大波長としては特に制限される ものではなぐ原理的には中心金属、配位子、配位子の置換基等を選択することで 得られる発光波長を変化させることができるが、リン光性ィ匕合物のリン光発光波長が 3 80〜480nmにリン光発光の極大波長を有することが好まし!/、。このような青色リン光 発光の有機 EL素子や、白色リン光発光の有機 EL素子で、より一層発光効率を高め ることがでさる。 In the present invention, the phosphorescent emission maximum wavelength of the phosphorescent compound is not particularly limited. In principle, by selecting a central metal, a ligand, a ligand substituent, and the like. The emission wavelength can be changed, but the phosphorescence emission wavelength of the phosphorescent compound is 3 It is preferable to have a phosphorescent maximum wavelength at 80-480nm! /. With such blue phosphorescent organic EL elements and white phosphorescent organic EL elements, the luminous efficiency can be further improved.
[0222] 本発明の有機 EL素子や本発明に係る化合物の発光する色は、「新編色彩科学ハ ンドブック」（日本色彩学会編、東京大学出版会、 1985)の 108頁の図 4. 16におい て、分光放射輝度計 CS - 1000 (コ-力ミノルタセンシング社製)で測定した結果を C IE色度座標に当てはめたときの色で決定される。  [0222] The light emission color of the organic EL device of the present invention and the compound of the present invention is shown in Fig. 4.16 on page 108 of "New Color Science Handbook" (Edited by the Japan Society for Color Science, University of Tokyo Press, 1985). Therefore, it is determined by the color when the result measured with the spectral radiance meter CS-1000 (manufactured by Co-Force Minolta Sensing) is applied to the C IE chromaticity coordinates.
[0223] 発光層は上記化合物を、例えば、真空蒸着法、スピンコート法、キャスト法、 LB法、 インクジェット法等の公知の薄膜ィ匕法により製膜して形成することができる。発光層と しての膜厚は特に制限はないが、通常は511111〜5 111、好ましくは 5〜200nmの範 囲で選ばれる。この発光層はこれらのリン光性化合物やホスト化合物が 1種または 2 種以上力もなる一層構造であってもよいし、あるいは同一組成または異種組成の複 数層からなる積層構造であってもよ ヽ。  [0223] The light-emitting layer can be formed by depositing the above compound by a known thin film method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. The thickness of the light emitting layer is not particularly limited, but is usually selected within the range of 511111 to 5111, preferably 5 to 200 nm. This light emitting layer may have a single layer structure in which these phosphorescent compounds and host compounds have one or more kinds of force, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.ヽ.
[0224] 《正孔輸送層》  [0224] << Hole Transport Layer >>
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料力 なり、広い意味で 正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層または複数 層設けることができる。  The hole transport layer is a hole transport material having a function of transporting holes. In a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.
[0225] 正孔輸送材料としては、正孔の注入または輸送、電子の障壁性の!/、ずれかを有す るものであり、有機物、無機物のいずれであってもよい。例えば、トリァゾール誘導体 、ォキサジァゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ビラ ゾリン誘導体及びピラゾロン誘導体、フ -レンジァミン誘導体、ァリールァミン誘導 体、ァミノ置換カルコン誘導体、ォキサゾール誘導体、スチリルアントラセン誘導体、 フルォレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、ァニリ ン系共重合体、また導電性高分子オリゴマー、特にチォフェンオリゴマー等が挙げら れる。  [0225] The hole transport material has either injection or transport of holes and / or a barrier property of electrons, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, violazoline derivatives and pyrazolone derivatives, fluorenedamine derivatives, arylene amine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
[0226] 正孔輸送材料としては上記のものを使用することができる力 ボルフイリンィ匕合物、 芳香族第 3級ァミン化合物及びスチリルアミン化合物、特に芳香族第 3級アミンィ匕合 物を用いることが好ましい。 [0227] 芳香族第 3級アミンィ匕合物及びスチリルアミンィ匕合物の代表例としては、 N, N, N ' , N' —テトラフエニル一 4, 4' —ジァミノフエ-ル； N, N' —ジフエ-ル一 N, N ' —ビス（3—メチルフエ-ル）一〔1 , 1' —ビフエ-ル〕一 4, 4' —ジァミン（TPD) ; 2, 2 ビス（4 ジ一 p トリルァミノフエ-ル）プロパン； 1 , 1—ビス（4 ジ一 p トリ ルァミノフエ-ル）シクロへキサン； N, N, N' , N' —テトラ一 p トリル一 4, 4' - ジアミノビフエ-ル； 1 , 1 ビス（4 ジ一 p トリルァミノフエ-ル） 4 フエ-ルシク 口へキサン；ビス（4 -ジメチルァミノ 2 メチルフエ-ル）フエニルメタン；ビス（4 -ジ —p トリルァミノフエ-ル）フエ-ルメタン； N, N' —ジフエ-ル一 N, N' —ジ（4— メトキシフエ-ル） 4, 4' ージアミノビフエニル； N, N, N' , N' —テトラフエ-ル —4, 4' ージアミノジフエ-ルエーテル； 4, 4' ビス（ジフエ-ルァミノ）クオ一ドリフ ェ -ル； N, N, N トリ（p トリル）ァミン； 4— (ジ— p トリルァミノ）— 4' —〔4— (ジ —p トリルァミノ）スチリル〕スチルベン； 4— N, N ジフエ-ルァミノ—（2 ジフエ- ルビ-ル）ベンゼン； 3—メトキシ一 4' — N, N ジフエニルアミノスチルベンゼン； N フエ-ルカルバゾール、更には米国特許第 5, 061 , 569号明細書に記載されて いる 2個の縮合芳香族環を分子内に有するもの、例えば、 4, 4' ビス〔N—（1ーナ フチル） N フエ-ルァミノ〕ビフヱ-ル（NPD)、特開平 4 308688号公報に記 載されているトリフエ-ルァミンユニットが 3つスターバースト型に連結された 4, 4' , A" —トリス〔?^— (3—メチルフエ-ル） N フエ-ルァミノ〕トリフエ-ルァミン（MTD ATA)等が挙げられる。 [0226] The ability to use the above-mentioned materials as the hole transport material [0226] It is possible to use a borfilin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound. preferable. [0227] Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-1,4'-diamineamino; N, N' —Diphenyl N, N '— Bis (3-methylphenol) 1 [1, 1' — Biphenyl] 1, 4, 4 '— Diamine (TPD); 2, 2 Bis (4 Di-p-tolylaminophenol 1,1-bis (4 di-l-tri-laminophenol) cyclohexane; N, N, N ', N' —tetra-l-tolyl 4,4'-diaminobiphenyl; 1, 1 Bis (4 di-p-triaminophenol) 4 Phenol mouth hexane; Bis (4-dimethylamino 2-methylphenol) phenylmethane; Bis (4-di-p-triaminophenol) phenylmethane; N, N ' —Diphenyl N, N ′ —Di (4-methoxyphenyl) 4, 4 ′ diaminobiphenyl; N, N, N ′, N ′ —Tetraphenyl —4, 4 ′ diaminodiph -Luether; 4, 4 'Bis (diphenylamino) quadryl; N, N, N Tri (p tolyl) amine; 4— (Di-p-tolylamino) — 4 ′ — [4— (Di — p-tolylamino) styryl] stilbene; 4-N, N diphenylamino- (2 diphenyl) benzene; 3-methoxy 1'-N, N diphenylaminostilbenzene; N phenolcarbazole, and more US Pat. No. 5,061,569 having two condensed aromatic rings in the molecule, for example, 4, 4 ′ bis [N- (1-naphthyl) N ferroamino ] Biffle (NPD), three triphenylamine units described in Japanese Patent Laid-Open No. 4 308688 are connected in a starburst type 4, 4 ', A "— Tris [? ^ — (3 -Methylphenol) N-phenylamino] triphenylamine (MTD ATA).
[0228] 更に、これらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖と した高分子材料を用いることもできる。また、 p型— Si、 p型— SiC等の無機化合物も 正孔注入材料、正孔輸送材料として使用することができる。  [0228] Further, a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used. In addition, inorganic compounds such as p-type—Si and p-type—SiC can also be used as the hole injection material and the hole transport material.
[0229] 正孔輸送層は上記正孔輸送材料を、例えば、真空蒸着法、スピンコート法、キャス ト法、インクジェット法を含む印刷法、 LB法等の公知の方法により、薄膜ィ匕することに より形成することができる。正孔輸送層の膜厚については特に制限はないが、通常は 5nm〜5 μ m程度、好ましくは 5〜200nmである。この正孔輸送層は上記材料の 1 種または 2種以上力もなる一層構造であってもよ 、。  [0229] The hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The hole transport layer may have a single layer structure that can be one or more of the above materials.
[0230] 《電子輸送層》 電子輸送層とは電子を輸送する機能を有する材料力 なり、広い意味で電子注入 層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層または複数層設けるこ とがでさる。 [0230] 《Electron Transport Layer》 The electron transport layer is a material force having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. An electron transport layer may be provided as a single layer or multiple layers.
[0231] 従来、単層の電子輸送層、及び複数層とする場合は発光層に対して陰極側に隣 接する電子輸送層に用いられる電子輸送材料 (正孔阻止材料を兼ねる）としては、陰 極より注入された電子を発光層に伝達する機能を有していればよぐその材料として は従来公知の化合物の中から任意のものを選択して用いることができ、例えば、 -ト 口置換フルオレン誘導体、ジフヱ-ルキノン誘導体、チォピランジオキシド誘導体、力 ルボジイミド、フレオレニリデンメタン誘導体、アントラキノジメタン及びアントロン誘導 体、ォキサジァゾール誘導体等が挙げられる。更に、上記ォキサジァゾール誘導体 にお 、て、ォキサジァゾール環の酸素原子を硫黄原子に置換したチアジアゾール誘 導体、電子吸引基として知られているキノキサリン環を有するキノキサリン誘導体も、 電子輸送材料として用いることができる。更にこれらの材料を高分子鎖に導入した、 またはこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。  Conventionally, in the case of a single electron transport layer and a plurality of layers, as an electron transport material (also serving as a hole blocking material) used for an electron transport layer adjacent to the light emitting layer on the cathode side, Any material can be selected from conventionally known compounds as long as it has a function of transmitting electrons injected from the electrode to the light-emitting layer. Examples include fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, strength rubodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxaziazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material. Further, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
[0232] また、 8 キノリノール誘導体の金属錯体、例えば、トリス（8 キノリノール)アルミ- ゥム（Alq)、トリス（5, 7—ジクロロ一 8—キノリノール）アルミニウム、トリス（5, 7—ジブ ロモ一 8 キノリノール）アルミニウム、トリス（2 メチル 8 -キノリノール）アルミ-ゥ ム、トリス（5—メチル 8—キノリノール）アルミニウム、ビス（8—キノリノール）亜鉛（Zn q)等、及びこれらの金属錯体の中心金属が In、 Mg、 Cu、 Ca、 Sn、 Gaまたは Pbに 置き替わった金属錯体も、電子輸送材料として用いることができる。その他、メタルフ リーもしくはメタルフタロシアニン、またはそれらの末端がアルキル基ゃスルホン酸基 等で置換されているものも、電子輸送材料として好ましく用いることができる。また、発 光層の材料として例示したジスチリルビラジン誘導体も、電子輸送材料として用いる ことができるし、正孔注入層、正孔輸送層と同様に、 n型— Si、 n型— SiC等の無機半 導体も電子輸送材料として用いることができる。  [0232] In addition, metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dibromone) 8quinolinol) aluminum, tris (2methyl 8-quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc., and the central metal of these metal complexes Metal complexes in which is replaced with In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials. In addition, metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material. In addition, the distyrylvirazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, n-type—Si, n-type—SiC, etc. These inorganic semiconductors can also be used as electron transport materials.
[0233] 電子輸送層は上記電子輸送材料を、例えば、真空蒸着法、スピンコート法、キャス ト法、インクジェット法を含む印刷法、 LB法等の公知の方法により、薄膜ィ匕することに より形成することができる。電子輸送層の膜厚については特に制限はないが、通常は 5nm〜5 μ m程度、好ましくは 5〜200nmである。電子輸送層は上記材料の 1種ま たは 2種以上力もなる一層構造であってもよ 、。 [0233] The electron transport layer is obtained by thin-filming the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an inkjet method, or an LB method. Can be formed. There is no particular limitation on the thickness of the electron transport layer, but normally The thickness is about 5 nm to 5 μm, preferably 5 to 200 nm. The electron transport layer may be a single layer structure having one or more of the above materials.
[0234] 《基体》  [0234] <Substrate>
本発明の有機 EL素子は、基体上に形成されているのが好ましい。  The organic EL device of the present invention is preferably formed on a substrate.
[0235] 本発明の有機 EL素子に用いることのできる基体 (以下、基板、基材、支持体等とも いう）としては、ガラス、プラスチック等の種類には特に限定はなぐまた、透明のもの であれば特に制限はないが、好ましく用いられる基板としては、例えば、ガラス、石英 、光透過性榭脂フィルムを挙げることができる。特に好ましい基体は、有機 EL素子に フレキシブル性を与えることが可能な榭脂フィルムである。  [0235] The substrate (hereinafter also referred to as substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is transparent. The substrate is not particularly limited as long as it is used, but preferred examples of the substrate include glass, quartz, and a light-transmitting resin film. A particularly preferable substrate is a resin film capable of imparting flexibility to the organic EL element.
[0236] 榭脂フィルムとしては、例えば、ポリエチレンテレフタレート（PET)、ポリエチレンナ フタレート（PEN)、ポリエーテルスルホン（PES)、ポリエーテルイミド、ポリエーテル エーテルケトン、ポリフエ-レンスルフイド、ポリアリレート、ポリイミド、ポリカーボネート (PC)、セルローストリアセテート (TAC)、セルロースアセテートプロピオネート（CAP )等力もなるフィルム等が挙げられる。榭脂フィルムの表面には、無機物、有機物の被 膜またはその両者のハイブリッド被膜が形成されて 、てもよ 、。  [0236] Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyether etherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate. (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like. On the surface of the resin film, an inorganic film, an organic film, or a hybrid film of the both may be formed.
[0237] 本発明の有機 EL素子の発光の室温における外部取り出し効率は 1%以上であるこ と力 子ましく、より好ましくは 5%以上である。ここに、外部取り出し量子効率（％) =有 機 EL素子外部に発光した光子数 Z有機 EL素子に流した電子数 X 100である。  [0237] The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted outside the organic EL element Z the number of electrons X 100 flowing through the organic EL element.
[0238] また、カラーフィルタ一等の色相改良フィルタ一等を併用しても、有機 EL素子から の発光色を蛍光体を用いて多色へ変換する色変換フィルターを併用してもよ ヽ。色 変換フィルターを用いる場合においては、有機 EL素子の発光の λ maxは 480nm以 下が好ましい。  [0238] In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination. In the case of using a color conversion filter, the λ max of light emission of the organic EL element is preferably 480 nm or less.
[0239] 《有機 EL素子の作製方法》  [0239] <Method for manufacturing organic EL element>
本発明の有機 EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層 Z発光層 Z電子輸送層 Z電子注入層 Z陰極からなる有機 EL素子の作製法につい て説明する。  As an example of the method for producing the organic EL device of the present invention, a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z cathode will be described.
[0240] まず適当な基体上に所望の電極物質、例えば、陽極用物質力 なる薄膜を 1 μ m 以下、好ましくは 10〜200nmの膜厚になるように、蒸着やスパッタリング等の方法に より形成させ、陽極を作製する。次に、この上に有機 EL素子材料である正孔注入層 、正孔輸送層、発光層、電子輸送層、電子注入層、正孔阻止層の有機化合物薄膜 を形成させる。 [0240] First, on a suitable substrate, a desired electrode material, for example, a thin film having a material force for an anode is deposited by a method such as vapor deposition or sputtering so that the film thickness is 1 μm or less, preferably 10 to 200 nm. To form an anode. Next, an organic compound thin film of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer, which is an organic EL element material, is formed thereon.
[0241] この有機化合物薄膜の薄膜ィ匕の方法としては、前記の如く蒸着法、ウエットプロセス  [0241] As a method of thin film formation of this organic compound thin film, as described above, vapor deposition method, wet process
(スピンコート法、キャスト法、インクジェット法、印刷法)等があるが、均質な膜が得ら れやすぐ且つピンホールが生成しにくい等の点から、真空蒸着法、スピンコート法、 インクジェット法、印刷法が特に好ましい。更に層毎に異なる製膜法を適用してもよい 。製膜に蒸着法を採用する場合、その蒸着条件は使用する化合物の種類等により異 なるが、一般にボート加熱温度 50〜450°C、真空度 10—6〜10—2Pa、蒸着速度 0. 01 〜50nmZ秒、基板温度— 50〜300。C、膜厚 0. lnm〜5 μ m、好ましくは 5〜200 nmの範囲で適宜選ぶことが望まし 、。 (Spin coating method, casting method, ink jet method, printing method) etc., but vacuum deposition method, spin coating method, ink jet method from the point that a homogeneous film is obtained and pinholes are not easily generated. The printing method is particularly preferred. Further, a different film forming method may be applied for each layer. When employing the vapor deposition film, the deposition conditions are different due to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 to 10-2 Pa, deposition rate 0. 01 ~ 50nmZ seconds, substrate temperature-50 ~ 300. C, film thickness of 0.1 nm to 5 μm, preferably 5 to 200 nm, preferably selected appropriately.
[0242] これらの層を形成後、その上に陰極用物質力もなる薄膜を、 1 μ m以下好ましくは 5 0nm〜200nmの範囲の膜厚になるように、例えば、蒸着やスパッタリング等の方法 により形成させ、陰極を設けることにより所望の有機 EL素子が得られる。この有機 EL 素子の作製は、一回の真空引きで一貫して正孔注入層から陰極まで作製するのが 好ましいが、途中で取り出して異なる製膜法を施しても構わない。その際、作業を乾 燥不活性ガス雰囲気下で行う等の配慮が必要となる。  [0242] After these layers are formed, a thin film that also has a material force for the cathode is formed thereon by a method such as vapor deposition or sputtering so that the film thickness becomes 1 μm or less, preferably in the range of 50 nm to 200 nm. By forming the cathode and providing the cathode, a desired organic EL device can be obtained. The organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
[0243] 本発明の多色の表示装置は発光層形成時のみシャドーマスクを設け、他層は共通 であるのでシャドーマスク等のパターユングは不要であり、一面に蒸着法、キャスト法 、スピンコート法、インクジェット法、印刷法等で膜を形成できる。発光層のみパター- ングを行う場合、その方法に限定はないが、好ましくは蒸着法、インクジェット法、印 刷法である。蒸着法を用いる場合においては、シャドーマスクを用いたパターユング が好ましい。  [0243] The multicolor display device of the present invention is provided with a shadow mask only at the time of forming a light emitting layer, and the other layers are common, so there is no need for patterning such as a shadow mask. A film can be formed by a method, an inkjet method, a printing method, or the like. When patterning only the light emitting layer, the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable. When using the vapor deposition method, patterning using a shadow mask is preferred.
[0244] また作製順序を逆にして、陰極、電子注入層、電子輸送層、発光層、正孔輸送層、 正孔注入層、陽極の順に作製することも可能である。このようにして得られた多色の 表示装置に、直流電圧を印加する場合には、陽極を +、陰極を一の極性として電圧 2〜40V程度を印加すると、発光が観測できる。また交流電圧を印加してもよい。な お、印加する交流の波形は任意でよい。 [0245] 本発明の表示装置は、表示デバイス、ディスプレイ、各種発光光源として用いること ができる。表示デバイス、ディスプレイにおいて、青、赤、緑発光の 3種の有機 EL素 子を用いることにより、フルカラーの表示が可能となる。 [0244] Alternatively, the order of preparation may be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode may be formed in this order. When a DC voltage is applied to the multi-color display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the anode as + and the cathode as one polarity. An alternating voltage may be applied. The AC waveform to be applied may be arbitrary. [0245] The display device of the present invention can be used as a display device, a display, and various light emission sources. Display devices and displays can be displayed in full color by using three types of organic EL elements that emit blue, red, and green light.
[0246] 表示デバイス、ディスプレイとしてはテレビ、ノ ソコン、モパイル機器、 AV機器、文 字放送表示、 自動車内の情報表示等が挙げられる。特に静止画像や動画像を再生 する表示装置として使用してもよぐ動画再生用の表示装置として使用する場合の駆 動方式は単純マトリックス (パッシブマトリックス）方式でもアクティブマトリックス方式で もどちらでもよい。  [0246] Examples of the display device and display include a television, a computer, a mopile device, an AV device, a character broadcast display, and an information display in a car. In particular, the driving method when used as a display device for reproducing moving images, which may be used as a display device for reproducing still images or moving images, may be either a simple matrix (passive matrix) method or an active matrix method.
[0247] 本発明の照明装置は家庭用照明、車内照明、時計や液晶用のバックライト、看板 広告、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源 、光センサーの光源等が挙げられるがこれに限定するものではない。  [0247] The lighting device of the present invention includes home lighting, interior lighting, backlights for clocks and liquid crystals, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Examples include, but are not limited to, a sensor light source.
[0248] また、本発明の有機 EL素子に共振器構造を持たせた有機 EL素子として用いても よい。このような共振器構造を有した有機 EL素子の使用目的としては、光記憶媒体 の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙 げられる力 これらに限定されない。また、レーザ発振をさせることにより、上記用途に 使用してちょい。  [0248] Further, the organic EL element of the present invention may be used as an organic EL element having a resonator structure. The organic EL elements having such a resonator structure can be used for light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light sources of optical sensors, etc. It is not limited. In addition, it can be used for the above applications by causing laser oscillation.
[0249] 《表示装置》  [0249] <Display device>
本発明の有機 EL素子は、照明用や露光光源のような 1種のランプとして使用しても よいし、画像を投影するタイプのプロジェクシヨン装置や、静止画像や動画像を直接 視認するタイプの表示装置 (ディスプレイ）として使用してもよい。動画再生用の表示 装置として使用する場合の駆動方式は単純マトリックス (パッシブマトリックス)方式で もアクティブマトリックス方式でもどちらでもよい。または、異なる発光色を有する本発 明の有機 EL素子を 3種以上使用することにより、フルカラー表示装置を作製すること が可能である。または、一色の発光色、例えば、白色発光をカラーフィルターを用い て BGRにし、フルカラー化することも可能である。更に有機 ELの発光色を色変換フィ ルターを用いて他色に変換しフルカラー化することも可能であるが、その場合、有機 EL発光の λ maxは 480nm以下であることが好ましい。  The organic EL element of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device that projects an image, or a type that directly recognizes a still image or a moving image. It may be used as a display device (display). When used as a display device for video playback, the drive method may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using three or more organic EL elements of the present invention having different emission colors. Alternatively, it is possible to make a single color emission color, for example, white emission, into BGR by using a color filter to achieve full color. Furthermore, it is possible to convert the emission color of the organic EL to another color using a color conversion filter, and in this case, the λ max of the organic EL emission is preferably 480 nm or less.
[0250] 本発明の有機 EL素子力 構成される表示装置の一例を図面に基づいて説明する [0251] 図 1は、有機 EL素子力 構成される表示装置の一例を示した模式図である。有機 EL素子の発光により画像情報の表示を行う、例えば、携帯電話等のディスプレイの 模式図である。 [0250] An example of a display device comprising the organic EL element power of the present invention will be described with reference to the drawings. FIG. 1 is a schematic view showing an example of a display device configured with organic EL element power. FIG. 2 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
[0252] ディスプレイ 1は、複数の画素を有する表示部 A、画像情報に基づいて表示部 Aの 画像走査を行う制御部 B等力もなる。  [0252] The display 1 also includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
[0253] 制御部 Bは、表示部 Aと電気的に接続され、複数の画素それぞれに外部からの画 像情報に基づいて走査信号と画像データ信号を送り、走査信号により走査線毎の画 素が画像データ信号に応じて順次発光して画像走査を行って画像情報を表示部 A に表示する。 [0253] The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of the plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.
[0254] 図 2は、表示部 Aの模式図である。 FIG. 2 is a schematic diagram of the display unit A.
[0255] 表示部 Aは基板上に、複数の走査線 5及びデータ線 6を含む配線部と、複数の画 素 3等とを有する。表示部 Aの主要な部材の説明を以下に行う。図 2においては、画 素 3の発光した光が、白矢印方向（下方向）へ取り出される場合を示して 、る。  [0255] The display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3, and the like on a substrate. The main members of the display unit A will be described below. FIG. 2 shows the case where the light emitted from pixel 3 is extracted in the direction of the white arrow (downward).
[0256] 配線部の走査線 5及び複数のデータ線 6は、各々導電材料からなり、走査線 5とデ ータ線 6は格子状に直交して、直交する位置で画素 3に接続している（詳細は図示せ ず)。  [0256] The scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at orthogonal positions. (Details not shown).
[0257] 画素 3は、走査線 5から走査信号が印加されると、データ線 6から画像データ信号を 受け取り、受け取った画像データに応じて発光する。発光の色が赤領域の画素、緑 領域の画素、青領域の画素を、適宜、同一基板上に並置することによって、フルカラ 一表示が可能となる。  [0257] When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light according to the received image data. Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
[0258] 次に、画素の発光プロセスを説明する。  Next, the light emission process of the pixel will be described.
[0259] 図 3は、画素の模式図である。  [0259] FIG. 3 is a schematic diagram of a pixel.
[0260] 画素は、有機 EL素子 10、スイッチングトランジスタ 11、駆動トランジスタ 12、コンデ ンサ 13等を備えている。複数の画素に有機 EL素子 10として、赤色、緑色、青色発 光の有機 EL素子を用い、これらを同一基板上に並置することでフルカラー表示を行 うことができる。  [0260] The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. Full-color display can be performed by using organic EL elements of red, green, and blue light emission as organic EL elements 10 in a plurality of pixels and arranging them on the same substrate.
[0261] 図 3において、制御部 B力もデータ線 6を介してスイッチングトランジスタ 11のドレイ ンに画像データ信号が印加される。そして、制御部 B力 走査線 5を介してスィッチン グトランジスタ 11のゲートに走査信号が印加されると、スイッチングトランジスタ 11の 駆動がオンし、ドレインに印加された画像データ信号がコンデンサ 13と駆動トランジ スタ 12のゲートに伝達される。 [0261] In FIG. 3, the control unit B force is also connected to the drain of the switching transistor 11 via the data line 6. An image data signal is applied to the screen. When a scanning signal is applied to the gate of the switching transistor 11 via the control unit B force scanning line 5, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of the star 12.
[0262] 画像データ信号の伝達により、コンデンサ 13が画像データ信号の電位に応じて充 電されるとともに、駆動トランジスタ 12の駆動がオンする。駆動トランジスタ 12は、ドレ インが電源ライン 7に接続され、ソースが有機 EL素子 10の電極に接続されており、ゲ 一トに印加された画像データ信号の電位に応じて電源ライン 7から有機 EL素子 10に 電流が供給される。 [0262] By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the organic EL element is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Current is supplied to element 10.
[0263] 制御部 Bの順次走査により走査信号が次の走査線 5に移ると、スイッチングトランジ スタ 11の駆動がオフする。しかし、スイッチングトランジスタ 11の駆動がオフしてもコン デンサ 13は充電された画像データ信号の電位を保持するので、駆動トランジスタ 12 の駆動はオン状態が保たれて、次の走査信号の印加が行われるまで有機 EL素子 1 0の発光が継続する。順次走査により次に走査信号が印加されたとき、走査信号に 同期した次の画像データ信号の電位に応じて駆動トランジスタ 12が駆動して有機 E L素子 10が発光する。  [0263] When the scanning signal is moved to the next scanning line 5 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The organic EL device 10 continues to emit light until it is seen. When a scanning signal is next applied by sequential scanning, the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
[0264] すなわち、有機 EL素子 10の発光は、複数の画素それぞれの有機 EL素子 10に対 して、アクティブ素子であるスイッチングトランジスタ 11と駆動トランジスタ 12を設けて 、複数の画素 3それぞれの有機 EL素子 10の発光を行っている。このような発光方法 をアクティブマトリックス方式と呼んで 、る。  That is, the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for each of the organic EL elements 10 of each of the plurality of pixels. Element 10 is emitting light. Such a light emission method is called an active matrix method.
[0265] ここで、有機 EL素子 10の発光は、複数の階調電位を持つ多値の画像データ信号 による複数の階調の発光でもよ 、し、 2値の画像データ信号による所定の発光量の オン、才フでもよ！/、。  Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission amount by a binary image data signal. On, even a talent! /.
[0266] また、コンデンサ 13の電位の保持は、次の走査信号の印加まで継続して保持して もよ 、し、次の走査信号が印加される直前に放電させてもょ 、。  [0266] Further, the potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
[0267] 本発明にお 、ては、上述したアクティブマトリックス方式に限らず、走査信号が走査 されたときのみデータ信号に応じて有機 EL素子を発光させるパッシブマトリックス方 式の発光駆動でもよい。 [0268] 図 4は、ノッシブマトリックス方式による表示装置の模式図である。図 4にお 、て、複 数の走査線 5と複数の画像データ線 6が画素 3を挟んで対向して格子状に設けられ ている。 [0267] In the present invention, not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned. [0268] FIG. 4 is a schematic diagram of a display device based on a noisy matrix method. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
[0269] 順次走査により走査線 5の走査信号が印加されたとき、印加された走査線 5に接続 して 、る画素 3が画像データ信号に応じて発光する。ノッシブマトリックス方式では画 素 3にアクティブ素子がなく、製造コストの低減が計れる。  [0269] When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixel 3 connected to the applied scanning line 5 emits light in accordance with the image data signal. With the noisy matrix method, pixel 3 has no active elements, and manufacturing costs can be reduced.
[0270] 本発明に係わる有機 EL材料は、また、照明装置として、実質白色の発光を生じる 有機 EL素子に適用できる。複数の発光材料により複数の発光色を同時に発光させ て混色により白色発光を得る。複数の発光色の組み合わせとしては、青色、緑色、青 色の 3原色の 3つの発光極大波長を含有させたものでもよいし、青色と黄色、青緑と 橙色等の補色の関係を利用した 2つの発光極大波長を含有したものでもよい。  [0270] The organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by mixing colors. The combination of multiple emission colors may include the three maximum emission wavelengths of the three primary colors of blue, green, and blue, and it uses the relationship of complementary colors such as blue and yellow, and blue-green and orange 2 It may be one containing two emission maximum wavelengths.
[0271] また、複数の発光色を得るための発光材料の組み合わせは、複数のリン光または 蛍光を発光する材料 (発光ドーパント）を、複数組み合わせたもの、蛍光またはリン光 を発光する発光材料と、該発光材料からの光を励起光として発光する色素材料とを 組み合わせたものの 、ずれでもよ!/ヽが、本発明に係わる白色有機エレクト口ルミネッ センス素子においては、発光ドーパントを複数組み合わせる方式が好ましい。  [0271] In addition, a combination of light-emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials (light-emitting dopants), a fluorescent material or a phosphorescent material that emits phosphorescence. Although it is combined with a dye material that emits light from the light emitting material as excitation light, there is a difference between the light emitting materials! In the white organic electoluminescence device according to the present invention, there is a method of combining a plurality of light emitting dopants. preferable.
[0272] 複数の発光色を得るための有機エレクト口ルミネッセンス素子の層構成としては、複 数の発光ドーパントを、一つの発光層中に複数存在させる方法、複数の発光層を有 し、各発光層中に発光波長の異なるドーパントをそれぞれ存在させる方法、異なる波 長に発光する微小画素をマトリックス状に形成する方法等が挙げられる。  [0272] The layer structure of the organic-electric-mouth luminescence device for obtaining a plurality of emission colors includes a method in which a plurality of emission dopants exist in one emission layer, a plurality of emission layers, and each emission Examples thereof include a method in which dopants having different emission wavelengths are present in the layer, and a method in which minute pixels emitting light of different wavelengths are formed in a matrix.
[0273] 本発明に係わる白色有機エレクト口ルミネッセンス素子においては、必要に応じ製 膜時にメタルマスクやインクジェットプリンティング法等でパター-ングを施してもよい 。 ノターニングする場合は、電極のみをパター-ングしてもいいし、電極と発光層を ノ ターニングしても 、 、し、素子全層をパター-ングしても 、 、。  [0273] In the white organic electoluminescence device according to the present invention, patterning may be performed by a metal mask, an ink jet printing method, or the like at the time of film formation, if necessary. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire device layer may be patterned.
[0274] 発光層に用いる発光材料としては特に制限はなぐ例えば液晶表示素子における ノ ックライトであれば、 CF (カラーフィルター)特性に対応した波長範囲に適合するよ うに、本発明に係わる白金錯体、また公知の発光材料の中から任意のものを選択し て組み合わせて白色化すればょ 、。 [0275] このように、白色発光有機 EL素子は、前記表示デバイス、ディスプレイにカ卩えて、 各種発光光源、照明装置として、家庭用照明、車内照明、また、露光光源のような 1 種のランプとして、液晶表示装置のバックライト等、表示装置にも有用に用いられる。 [0274] The light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a knocklight in a liquid crystal display element, the platinum complex according to the present invention is adapted so as to conform to the wavelength range corresponding to the CF (color filter) characteristics. If you select any of the known luminescent materials and combine them to make them white. [0275] As described above, the white light-emitting organic EL element is used as a variety of light-emitting light sources and illuminating devices, in addition to the display device and display, and is a kind of lamp such as home lighting, interior lighting, and exposure light source In addition, it is also useful for display devices such as backlights of liquid crystal display devices.
[0276] その他、時計等のバックライト、看板広告、信号機、光記憶媒体等の光源、電子写 真複写機の光源、光通信処理機の光源、光センサーの光源等、更には表示装置を 必要とする一般の家庭用電気器具等広い範囲の用途が挙げられる。  [0276] Other light sources such as backlights for watches, billboard advertisements, traffic lights, optical storage media, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, and display devices are also required. And a wide range of uses such as general household appliances.
実施例  Example
[0277] 以下、実施例により本発明を説明するが、本発明はこれらに限定されない。  [0277] Hereinafter, the present invention will be described by way of examples, but the present invention is not limited thereto.
[0278] ここで、実施例に使用する化合物を下記示す。 [0278] Here, compounds used in Examples are shown below.
[0279] [化 75] [0279] [Chemical 75]
Figure imgf000092_0001
Figure imgf000092_0001
[0280] [化 76] TCNQ 卜リフエニルァミン [0280] [Chemical 76] TCNQ 卜 Liphenylamine
Figure imgf000093_0001
Figure imgf000093_0001
[0281] 実施例 1 [0281] Example 1
《有機 EL素子 1—1の作製》  << Production of organic EL element 1-1 >>
陽極として 100mm X 100mm X I . 1mmのガラス基板上に ITO (インジウムチンォ キシド)を lOOnm製膜した基板 (ΝΗテクノグラス社製 ΝΑ45)にパターユングを行つ た後、この ITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波 洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行なった。この透明支持基 板を市販の真空蒸着装置の基板ホルダーに固定し、一方、モリブデン製抵抗加熱ボ ートに α—NPDを 200mg入れ、別のモリブデン製抵抗加熱ボートに、 TCNQを 100 mg入れ、別のモリブデン製抵抗加熱ボートにホスト化合物として CBPを 200mg入れ 、別のモリブデン製抵抗加熱ボートにバソキュプロイン（BCP)を 200mg入れ、別の モリブデン製抵抗加熱ボートに Ir— 12を lOOmg入れ、更に別のモリブデン製抵抗力口 熱ボートに Alqを 200mg入れ、真空蒸着装置に取付けた。  The ITO transparent electrode was provided after patterning was performed on a substrate (ΝΗ Techno Glass Co., Ltd. ΝΑ45) obtained by depositing ITO (indium tin oxide) on a 100 mm X 100 mm XI .1 mm glass substrate as an anode. The transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation system, while 200 mg of α-NPD is placed in a molybdenum resistance heating boat, and 100 mg of TCNQ is placed in another molybdenum resistance heating boat. 200 mg of CBP as a host compound is put into another molybdenum resistance heating boat, 200 mg of bathocuproin (BCP) is put into another molybdenum resistance heating boat, Ir-12 is put into another molybdenum resistance heating boat, and another 100 mg Molybdenum resistance port 200 mg of Alq was placed in a thermal boat and attached to a vacuum evaporation system.
3  Three
[0282] 次!、で、真空槽を 4 X 10— 4Paまで減圧した後、 α—NPDと TCNQの入った前記加 熱ボートに通電して加熱し、蒸着速度 0. 2nmZ秒、 0. 004nmZ秒で透明支持基 板に共蒸着して膜厚が lOOnmになるように正孔輸送層を設けた。 [0282] Next !, in, after pressure in the vacuum tank was reduced to 4 X 10- 4 Pa, heated by supplying an electric current to the pressure heat boat containing alpha-NPD and TCNQ, deposition rate 0. 2NmZ seconds, 0. A hole transport layer was provided so that the film thickness was lOOnm by co-evaporation on a transparent support substrate at 004 nmZ seconds.
[0283] 更に ex NPDの入った前記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒 で前記正孔輸送層上に蒸着して膜厚が lOnmになるように電子阻止層を設けた。更 に CBPと Ir 12の入った前記加熱ボートに通電して加熱し、それぞれ蒸着速度 0. 2 nmZ秒、 0. 012nmZ秒で前記電子阻止層上に共蒸着して、膜厚 35nmになるよう に発光層を設けた。なお、蒸着時の基板温度は室温であった。更に BCPの入った前 記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒で前記発光層の上に蒸着し て膜厚 10nmの正孔阻止層を設けた。その上に、更に Alqの入った前記加熱ボート [0283] Further, an electron blocking layer was provided so that the heating boat containing ex NPD was energized and heated, and deposited on the hole transport layer at a deposition rate of 0. InmZ seconds to a film thickness of lOnm. . Furthermore, the heating boat containing CBP and Ir 12 was energized and heated, and co-deposited on the electron blocking layer at a deposition rate of 0.2 nmZ seconds and 0.012 nmZ seconds, respectively, so that the film thickness became 35 nm. A light emitting layer was provided. In addition, the substrate temperature at the time of vapor deposition was room temperature. Furthermore, the heating boat containing BCP is energized and heated, and deposited on the light emitting layer at a deposition rate of 0. InmZ seconds. Then, a hole blocking layer having a thickness of 10 nm was provided. On top of that, the heated boat with further Alq
3  Three
に通電して加熱し、蒸着速度 0. InmZ秒で前記電子輸送層の上に蒸着して、更に 膜厚 40nmの電子輸送層を設けた。なお、蒸着時の基板温度は室温であった。  Then, the film was evaporated on the electron transport layer at a deposition rate of 0. InmZ seconds, and an electron transport layer having a thickness of 40 nm was further provided. In addition, the substrate temperature at the time of vapor deposition was room temperature.
[0284] 引き続きフッ化リチウム 0. 5nm及びアルミニウム 11 Onmを蒸着して陰極を形成し、 有機 EL素子 1— 1を作製した。  Subsequently, lithium fluoride 0.5 nm and aluminum 11 Onm were vapor-deposited to form a cathode, and an organic EL device 1-1 was produced.
[0285] 《有機 EL素子 1— 2〜1— 15の作製》  [0285] <Production of organic EL elements 1-2-1-15>
有機 EL素子 1—1の作製において、正孔輸送層のァクセプター化合物として用い て 、る TCNQ及びホストイ匕合物として用いて 、る CBPを表 1に示すように置き換えた 以外は同様にして、有機 EL素子 1— 2〜1— 15を各々作製した。  In the production of the organic EL device 1-1, the organic compound was similarly prepared except that CBP was used as an acceptor compound for the hole transport layer, and CBP was used as a compound for TCNQ and a host compound. EL elements 1-2-1 to 15 were produced.
[0286] 《有機 EL素子 1 1〜1 15の評価》  [0286] <Evaluation of organic EL elements 1 1 to 1 15>
以下のようにして作製した有機 EL素子 1 1〜1 15につ 、て、下記方法に従!、、 外部取り出し効率及び駆動電圧を評価した。  The organic EL devices 11 to 115 manufactured as described below were evaluated according to the following method to evaluate the external extraction efficiency and the driving voltage.
[0287] 《外部取りだし量子効率、駆動電圧》  [0287] 《External extraction quantum efficiency, drive voltage》
作製した有機 EL素子について、 23°C、乾燥窒素ガス雰囲気下で 2. 5mA/cm2 定電流を印カロしたときの外部取り出し量子効率 (％)、駆動電圧 (V)を測定した。なお 測定には同様に分光放射輝度計 CS— 1000 (コ-カミノルタセンシング社製)を用い た。得られた結果を表 1に示す。 The fabricated organic EL device was measured for external extraction quantum efficiency (%) and driving voltage (V) when a constant current of 2.5 mA / cm 2 was applied at 23 ° C in a dry nitrogen gas atmosphere. For the measurement, a spectral radiance meter CS-1000 (manufactured by Co-Camino Norta Sensing) was used in the same manner. The results obtained are shown in Table 1.
[0288] [表 1] [0288] [Table 1]
有機 一般式 （I) で ァクセプター 駆動電圧 外部取り出し収率 Organic In general formula (I) Acceptor Drive voltage External extraction yield
備考 Remarks
EL素子 表される化合物 化合物 (V) (%) EL element Compound represented Compound (V) (%)
1 -1 CBP TCNQ 4.5 9.5 比較例 1 -1 CBP TCNQ 4.5 9.5 Comparative example
1-2 7 none 7 12.9 比較例1-2 7 none 7 12.9 Comparative example
1-3 7 TCNQ 4.3 13.8 本発明1-3 7 TCNQ 4.3 13.8 Present invention
1一 4 60 DDQ 4.2 13.7 本発明1 1 4 60 DDQ 4.2 13.7 The present invention
1一 5 53 DNH 4.4 13.1 本発明1 1 5 53 DNH 4.4 13.1 Present invention
1一 6 72 TCNQF4 4.2 14 本発明1 1 6 72 TCNQF4 4.2 14 Present invention
1一 7 74 TCNQ 4 15 本発明1 1 7 74 TCNQ 4 15 The present invention
1一 8 78 Pt 4.5 12.8 本発明1 1 8 78 Pt 4.5 12.8 The present invention
1 -9 79 クロラニル 4.5 12.9 本発明1 -9 79 Chloranil 4.5 12.9 Present invention
1 -10 80 フルオラニル 4.4 13 本発明1 -10 80 Fluoranil 4.4 13 The present invention
1 -11 84 TNF 4.3 13.2 本発明1 -11 84 TNF 4.3 13.2 The present invention
1 -12 105 TCNE 4.3 13.9 本発明1 -12 105 TCNE 4.3 13.9 The present invention
1 -13 111 HCNB 4.3 14 本発明1 -13 111 HCNB 4.3 14 Present invention
1 -14 118 TCNQ 4.1 14.5 本発明1 -14 118 TCNQ 4.1 14.5 The present invention
1 -15 129 DDQ 4.1 14.6 本発明 1 -15 129 DDQ 4.1 14.6 The present invention
[0289] 表 1から、比較に比べて本発明の試料は、外部取りだし量子効率が高ぐ且つ駆動 電圧が低!ヽことが明らかである。 [0289] From Table 1, it is clear that the sample of the present invention has higher external extraction quantum efficiency and lower drive voltage than the comparison.
[0290] 実施例 2 [0290] Example 2
《有機 EL素子 2—1の作製》  << Preparation of organic EL element 2-1 >>
陽極として lOOmmX 100mm XI.1mmのガラス基板上に ITO (インジウムチンォ キシド）を lOOnm製膜した基板 (ΝΗテクノグラス社製 ΝΑ45)にパターユングを行つ た後、この ITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波 洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行なった。この透明支持基 板を市販の真空蒸着装置の基板ホルダーに固定し、一方モリブデン製抵抗加熱ボ ートに α— NPDを 200mg入れ、別のモリブデン製抵抗加熱ボートに、別のモリブデ ン製抵抗加熱ボートにホストイ匕合物として CBPを 200mg入れ、別のモリブデン製抵 抗加熱ボートにバソキュプロイン（BCP)を 200mg入れ、別のモリブデン製抵抗加熱 ボートに Ir—12を lOOmg入れ、更に別のモリブデン製抵抗加熱ボートに Alqを 200  After putting a lOOnm film on a lOOmmX 100mm XI.1mm glass substrate as an anode (ITOTechno Glass Co., Ltd. ΝΑ45), this transparent ITO electrode was provided. The support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaned for 5 minutes. This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation system, while 200 mg of α-NPD is placed in a molybdenum resistance heating boat, and another molybdenum resistance heating boat is placed in another molybdenum resistance heating boat. 200 mg CBP as a host compound in a boat, 200 mg bathocuproin (BCP) in another molybdenum resistance heating boat, another molybdenum resistance heating boat, Ir-12, lOOmg, and another molybdenum resistance 200 Alq on heated boat
3 mg入れ、更に別のボートにトリフエニルァミンを lOOmg入れ、真空蒸着装置に取付 [0291] 次 、で、真空槽を 4 X 10— 4Paまで減圧した後、 a—NPDの入った前記加熱ボート に通電して加熱し、蒸着速度 0. InmZ秒で透明支持基板に蒸着して膜厚が 40nm になるように正孔輸送層を設けた。更に、 CBPと Ir— 12の入った前記加熱ボートに 通電して加熱し、それぞれ蒸着速度 0. 2nmZ秒、 0. 012nmZ秒で前記電子阻止 層上に共蒸着して、膜厚 35nmになるように発光層を設けた。なお、蒸着時の基板温 度は室温であった。更に BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒で前記発光層の上に蒸着して膜厚 lOnmの正孔阻止層を設けた。その 上に、更に Alqとトリフエ-ルァミンの入った前記加熱ボートに通電して加熱し、蒸着 Add 3 mg, and add another lOOmg of triphenylamine to another boat and attach it to the vacuum evaporation system. [0291] in the following, after pressure in the vacuum tank was reduced to 4 X 10- 4 Pa, and heated by supplying an electric current to the boat containing a-NPD, was deposited on the transparent supporting substrate at a deposition rate of 0. InmZ sec Thus, a hole transport layer was provided so that the film thickness was 40 nm. Further, the heating boat containing CBP and Ir-12 was energized and heated, and co-deposited on the electron blocking layer at a deposition rate of 0.2 nmZ seconds and 0.012 nmZ seconds, respectively, so that the film thickness became 35 nm. A light emitting layer was provided. The substrate temperature during vapor deposition was room temperature. Further, the heating boat containing BCP was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0. InmZ seconds to provide a hole blocking layer having a thickness of lOnm. On top of that, the heating boat containing Alq and triphenylamine is further energized and heated for vapor deposition.
3  Three
速度 0. 2nmZ秒、 0. 004nmZ秒で前記正孔阻止層の上に共蒸着して膜厚 80nm の電子輸送層を設けた。なお蒸着時の基板温度は室温であった。  An electron transport layer having a thickness of 80 nm was formed by co-evaporation on the hole blocking layer at a speed of 0.2 nmZ seconds and 0.004 nmZ seconds. The substrate temperature during vapor deposition was room temperature.
[0292] 引き続きフッ化リチウム 0. 5nm及びアルミニウム 11 Onmを蒸着して陰極を形成し、 有機 EL素子 2— 1を作製した。  Subsequently, lithium fluoride 0.5 nm and aluminum 11 Onm were vapor-deposited to form a cathode, and an organic EL device 2-1 was produced.
[0293] 《有機 EL素子 2— 2〜2— 10の作製》  [0293] << Production of organic EL elements 2-2 to 2-10 >>
有機 EL素子 2— 1の作製にぉ 、て、電子輸送層のドナー化合物として用いて!/、るト リフエ-ルァミン及び正孔阻止材料として用いている BCPを表 2に示すように置き換 えた以外は、同様にして有機 EL素子 2— 2〜2— 10を各々作製した。  In the production of the organic EL device 2-1, the BCP used as the donor compound of the electron transport layer! /, The triphenylamine and the hole blocking material was replaced as shown in Table 2. Except for the above, organic EL elements 2-2 to 2-10 were produced in the same manner.
[0294] 《有機EL素子2—1〜2— 10の評価》  [0294] << Evaluation of Organic EL Elements 2-1 to 2-10 >>
有機 EL素子 2— 1〜2— 10を各々、実施例 1に記載と同様に評価した。得られた結 果を表 2に示す。  Each of the organic EL devices 2-1 to 2-10 was evaluated in the same manner as described in Example 1. Table 2 shows the results obtained.
[0295] [表 2] [0295] [Table 2]
有機 一般式 （I) で 駆動電圧 外部取り出し収率 Organic General formula (I) Drive voltage External extraction yield
ドナー化合物 備考 Donor compound Remarks
EL素子 表される化合物 (V) {%) EL element Compound (V) (%)
2-1 BCP 卜リフエニルァミン 5.5 9 比較例 2-1 BCP 卜 Liphenylamine 5.5 9 Comparative Example
2-2 1 卜リフエニルァミン 5.5 10.5 比較例2-2 1 Liphenylamine 5.5 10.5 Comparative Example
2-3 1 Ca 4.8 13.5 本発明2-3 1 Ca 4.8 13.5 The present invention
2— 4 44 Na 4.7 13.6 本発明2— 4 44 Na 4.7 13.6 The present invention
2-5 73 Cs 4.6 13.7 本発明2-5 73 Cs 4.6 13.7 The present invention
2-6 74 CS2CO3 4.4 14.5 本発明2-6 74 CS2CO3 4.4 14.5 The present invention
2-7 129 CHsCOOCs 4.5 14.3 本発明2-7 129 CHsCOOCs 4.5 14.3 The present invention
2-8 134 CsCI 4.5 14.4 本発明2-8 134 CsCI 4.5 14.4 The present invention
2-9 1 4 CsBr 4.4 14.4 本発明2-9 1 4 CsBr 4.4 14.4 The present invention
2-10 148 CH3SO3CS 4.5 14.4 本発明 2-10 148 CH3SO3CS 4.5 14.4 Present invention
[0296] 表 2から、比較に比べて本発明の試料は、外部取りだし量子効率が高ぐ且つ駆動 電圧が低レヽことが明らかである。 [0296] From Table 2, it is clear that the sample of the present invention has a higher external extraction quantum efficiency and a lower driving voltage than the comparison.
[0297] 実施例 3 [0297] Example 3
《有機 EL素子 3—1の作製》  << Production of organic EL element 3-1 >>
陽極として 100mm X 100mm XI. 1mmのガラス基板上に ITO (インジウムチンォ キシド)を lOOnm製膜した基板 (ΝΗテクノグラス社製 ΝΑ45)にパターユングを行つ た後、この ITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波 洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行なった。この透明支持基 板を市販の真空蒸着装置の基板ホルダーに固定し、一方、モリブデン製抵抗加熱ボ ートに α— NPDを 200mg入れ、別のモリブデン製抵抗加熱ボートに、 TCNQを 100 mg入れ、別のモリブデン製抵抗加熱ボートにホストイ匕合物として CBPを 200mg入れ 、別のモリブデン製抵抗加熱ボートにバソキュプロイン (BCP)を 200mg入れ、別の モリブデン製抵抗加熱ボートに Ir— 12を lOOmg入れ、更に別のモリブデン製抵抗力口 熱ボートに Alqを 200mg入れ、更に別のボートにトリフエ-ルァミンを lOOmg入れ、  100 mm X 100 mm XI. As a positive electrode A pattern was formed on a substrate (ΝΗ Techno Glass Co., Ltd. ΝΑ45) on which ITO (indium tin oxide) was formed on a 1 mm glass substrate, and this ITO transparent electrode was provided. The transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system. Meanwhile, 200 mg of α-NPD is placed in a molybdenum resistance heating boat, and 100 mg of TCNQ is placed in another molybdenum resistance heating boat. Put another 200 mg CBP as a host compound in another resistance heating boat made of molybdenum, put 200 mg bathocuproin (BCP) in another resistance heating boat made of molybdenum, and put lOO mg Ir-12 in another resistance heating boat made of molybdenum. Put another 200mg Alq into a resistance boat made of molybdenum and put another lOOmg of triphenylamine into another boat.
3  Three
真空蒸着装置に取付けた。  It was attached to a vacuum evaporation system.
[0298] 次 、で、真空槽を 4 X lO^Paまで減圧した後、 a—NPDと TCNQの入った前記カロ 熱ボートに通電して加熱し、蒸着速度 0. 2nmZ秒、 0. 004nmZ秒で透明支持基 板に共蒸着して膜厚が lOOnmになるように正孔輸送層を設けた。更にひ— NPDの 入った前記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒で前記正孔輸送層 上に蒸着して膜厚が lOnmになるように電子阻止層を設けた。更に CBPと Ir— 12の 入った前記加熱ボートに通電して加熱し、それぞれ蒸着速度 0. 2nmZ秒、 0. 012 nmZ秒で前記電子阻止層上に共蒸着して、膜厚 35nmになるように発光層を設け た。なお、蒸着時の基板温度は室温であった。更に BCPの入った前記加熱ボートに 通電して加熱し、蒸着速度 0. InmZ秒で前記発光層の上に蒸着して膜厚 lOnmの 正孔阻止層を設けた。その上に、更に Alqとトリフエニルァミンの入った前記加熱ボ [0298] Next, after depressurizing the vacuum chamber to 4 X lO ^ Pa, the energized heating boat containing a-NPD and TCNQ was energized and heated, and the deposition rate was 0.2 nmZ seconds and 0.004 nmZ seconds. Then, a hole transport layer was provided so that the film thickness was lOOnm by co-evaporation on the transparent support substrate. Furthermore, NPD The heating boat was energized and heated, and an electron blocking layer was provided so that the film thickness was lOnm by vapor deposition on the hole transport layer at a deposition rate of 0. InmZ seconds. Further, the heating boat containing CBP and Ir-12 was energized and heated, and co-deposited on the electron blocking layer at a deposition rate of 0.2 nmZ seconds and 0.012 nmZ seconds, respectively, so that the film thickness became 35 nm. Was provided with a light emitting layer. In addition, the substrate temperature at the time of vapor deposition was room temperature. Furthermore, the heating boat containing BCP was energized and heated, and deposited on the light emitting layer at a deposition rate of 0. InmZ seconds to provide a hole blocking layer having a thickness of lOnm. On top of that, the heating bottle containing Alq and triphenylamine is added.
3  Three
ートに通電して加熱し、蒸着速度 0. 2nmZ秒、 0. 004nmZ秒で前記正孔阻止層 の上に共蒸着して膜厚 80nmの電子輸送層を設けた。なお蒸着時の基板温度は室 温であった。  An electron transport layer having a thickness of 80 nm was formed by co-evaporation on the hole blocking layer at a deposition rate of 0.2 nmZ seconds and 0.004 nmZ seconds. The substrate temperature during vapor deposition was room temperature.
[0299] 引き続きフッ化リチウム 0. 5nm及びアルミニウム 11 Onmを蒸着して陰極を形成し、 有機 EL素子 3— 1を作製した。  Subsequently, lithium fluoride 0.5 nm and aluminum 11 Onm were vapor-deposited to form a cathode, and an organic EL device 3-1 was produced.
[0300] 《有機 EL素子 3— 2〜3— 12の作製》 [0300] << Production of organic EL elements 3-2-3-12 >>
有機 EL素子 3—1の作製において、正孔輸送層のァクセプター化合物として用い て 、る TCNQ、電子輸送層のドナー化合物として用いて!/、るトリフエ-ルァミン及び 正孔阻止材料として用 、て 、る BCPを表 3に示すように置き換えた以外は、 3— 1と 同様にして有機 EL素子 3— 2〜3— 12を各々作製した。  In the production of the organic EL device 3-1, as an acceptor compound for a hole transport layer, it is used as a TCNQ, as a donor compound for an electron transport layer! /, Used as a triphenylamine and a hole blocking material. Organic EL devices 3-2-3-12 were fabricated in the same manner as 3-1, except that the BCP was replaced as shown in Table 3.
[0301] 《有機EL素子3— 1〜3— 12の評価》 [0301] << Evaluation of Organic EL Elements 3-1-3-12 >>
得られた有機 EL素子 3— 1〜3— 12を各々実施例 1と同様に評価した。得られた結 果を表 3に示す。  The obtained organic EL devices 3-1 to 3-12 were evaluated in the same manner as in Example 1. Table 3 shows the results obtained.
[0302] [表 3] [0302] [Table 3]
一般式 （I) で ァクセブタ一 ドナ一 In general formula (I)
有機 EL素子 駆動電圧外部取り出し収率 備考 表される化合物 化合物 化合物 (V)  Organic EL device Drive voltage External yield Remarks Represented compound Compound Compound (V)
3—1 BCP TCNQ ト リフエニルァミン 4.5 8.1 比較例  3-1 BCP TCNQ Triphenylamine 4.5 8.1 Comparative Example
44 none none 8 12.9 比較例 44 none none 8 12.9 Comparative example
3-3 44 TCNQ Cs 3.8 13.3 本発明3-3 44 TCNQ Cs 3.8 13.3 Invention
3-4 73 剛 Na 4 13 本発明3-4 73 Go Na 4 13 The present invention
3-5 74 TCNQ 3.5 14.2 本発明3-5 74 TCNQ 3.5 14.2 The present invention
3-6 78 クロラニル Ca 3.9 13,4 本発明3-6 78 Chloranil Ca 3.9 13,4 The present invention
3-7 79 TCNE し ί 3.8 13,3 本発明3-7 79 TCNE ί 3.8 13,3 The present invention
3-8 84 T F Mg 3.8 13,2 本発明3-8 84 T F Mg 3.8 13,2 The present invention
3-9 129 DDQ CHaCOOCs 3.6 14.1 本発明3-9 129 DDQ CHaCOOCs 3.6 14.1 The present invention
3-10 134 TCNQF4 CsCI 3.6 14.1 本発明3-10 134 TCNQF4 CsCI 3.6 14.1 The present invention
3-11 1 4 HCNB CsBr 3.5 14 本発明3-11 1 4 HCNB CsBr 3.5 14 Present invention
3-12 1 8 TCNQ CHaSOsCs 3.5 14.1 本発明 3-12 1 8 TCNQ CHaSOsCs 3.5 14.1 The present invention
[0303] 表 3から、比較に比べて本発明の試料は、外部取りだし量子効率が高ぐ且つ駆動 電圧が低!/ヽことが明らかである。 [0303] From Table 3, it is clear that the sample of the present invention has higher external extraction quantum efficiency and lower driving voltage than the comparison.
[0304] 実施例 4 [0304] Example 4
実施例 1で作製した本発明の有機 EL素子 1— 15と、実施例 2で作製した本発明の 有機 EL素子 2— 6と、本発明の有機 EL素子 2— 6のリン光性化合物を例示化合物 Ir 9に置き換えた以外は、同様にして作製した赤色発光有機 EL素子を同一基板上 に並置し、図 1に示すアクティブマトリクス方式フルカラー表示装置を作製した。図 2 には作製したフルカラー表示装置の表示部 Aの模式図のみを示した。即ち同一基板 上に、複数の走査線 5及びデータ線 6を含む配線部と並置した複数の画素 3 (発光の 色が赤領域の画素、緑領域の画素、青領域の画素等）とを有し、配線部の走査線 5 及び複数のデータ線 6はそれぞれ導電材料力 なり、走査線 5とデータ線 6は格子状 に直交して、直交する位置で画素 3に接続している（詳細は図示せず)。前記複数の 画素 3は、それぞれの発光色に対応した有機 EL素子、アクティブ素子であるスィッチ ングトランジスタと駆動トランジスタそれぞれが設けられたアクティブマトリクス方式で 駆動されており、走査線 5から走査信号が印加されると、データ線 6から画像データ 信号を受け取り、受け取った画像データに応じて発光する。このように各赤、緑、青の 画素を適宜、並置することによって、フルカラー表示が可能となる。  Examples of the organic EL device 1-15 of the present invention produced in Example 1, the organic EL device 2-6 of the present invention produced in Example 2, and the phosphorescent compound of the organic EL device 2-6 of the present invention A red light-emitting organic EL device produced in the same manner except that the compound Ir 9 was used was placed side by side on the same substrate to produce an active matrix type full-color display device shown in FIG. Fig. 2 shows only a schematic diagram of display section A of the full-color display device that was fabricated. In other words, on the same substrate, there are a plurality of pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6. In addition, the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material force, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions (details Not shown). The plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, by arranging the red, green, and blue pixels as appropriate, full color display is possible.
[0305] フルカラー表示装置を駆動することにより、外部とりだし量子効率が高ぐ耐久性の 良好な、鮮明なフルカラー動画表示が得られた。 [0305] By driving a full-color display device, the external extraction quantum efficiency is high and the durability is high. Good and clear full-color moving image display was obtained.
[0306] 実施例 5  [0306] Example 5
《照明装置の作製》  <Production of lighting device>
実施例 3で作製した有機 EL素子 3— 5において、 CBPの入った加熱ボートと Ir— 1 2の入ったボート、 Ir- 9 (Btp Ir (acac)ともいう）の入ったボートをそれぞれ独立に通  In the organic EL device 3-5 prepared in Example 3, a heating boat containing CBP, a boat containing Ir-12, and a boat containing Ir-9 (also called Btp Ir (acac)) were independently provided. Through
2  2
電して発光ホストである CBPと発光ドーパントである Ir— 12及び Ir—9 (Btp Ir (acac  CBP as the luminescent host and Ir-12 and Ir-9 as the luminescent dopant (Btp Ir (acac
2 2
；) )の蒸着速度が、 100 : 5 : 0. 6になるように調節し、膜厚が 30nmになるように発光 層を設けた以外は有機 EL素子 3— 5と同様の方法で有機 EL素子 5— 1Wを作製し た。得られた有機 EL素子 5 - 1Wの非発光面をガラスケースで覆 、、図 5 (a)及び図 5 (b)で示す照明装置とした。照明装置は、発光効率が高く発光寿命の長い白色光 を発する薄型の照明装置として使用することができた。 ;) The deposition rate of)) was adjusted to 100: 5: 0.6, and the organic EL device was manufactured in the same manner as organic EL device 3-5 except that a light emitting layer was provided so that the film thickness was 30 nm. Element 5-1W was fabricated. The non-light-emitting surface of the obtained organic EL element 5-1W was covered with a glass case, and the lighting device shown in FIGS. 5 (a) and 5 (b) was obtained. The illuminating device could be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life.
なお、図 5 (a)および図 5 (b)における各部の名称は以下の通りである。  Note that the names of the parts in FIGS. 5 (a) and 5 (b) are as follows.
[0307] 101 透明電極付きガラス基板 [0307] 101 Glass substrate with transparent electrode
102 有機 EL層  102 OLED layer
103 陰極  103 cathode
104 ガラス製封止缶  104 glass sealing can
105 酸化バリウム (捕水剤）  105 Barium oxide (water trapping agent)
107 紫外線硬化型接着剤  107 UV curable adhesive
産業上の利用可能性  Industrial applicability
[0308] 本発明により、有機層の低抵抗化による素子の低電圧化、並びに高い発光効率を もつ電気光学的特性に優れた構成の有機 EL素子、照明装置及び表示装置を提供 することでさた。 [0308] According to the present invention, an organic EL element, an illumination device, and a display device having a structure with excellent electro-optical characteristics having a low light-emitting element by reducing the resistance of an organic layer and high luminous efficiency are provided. It was.

Claims

請求の範囲  The scope of the claims
[1] 陰極と陽極との間に発光層を少なくとも有する有機エレクト口ルミネッセンス素子に お 、て、少なくとも 1層に下記一般式（1)で表される化合物の少なくとも 1種を含有し [1] An organic electoluminescence device having at least a light emitting layer between a cathode and an anode, wherein at least one layer contains at least one compound represented by the following general formula (1).
、且つ正孔輸送材料及びァクセプター化合物を含有する正孔輸送層を有することを 特徴とする有機エレクト口ルミネッセンス素子。 And an organic electroluminescence device having a hole transport layer containing a hole transport material and an acceptor compound.
[化 1] 一般式 (1)  [Chemical formula 1] General formula (1)
^101  ^ 101
. - -c ゝ c- - -ヽ --c ゝ c---ヽ
i z2 iz 2
、1 \ c - -z3 - -C I ノ2 , 1 \ c--z 3 --CI no 2
(式中、 Z (Where Z
1は芳香族複素環を表し、 Z  1 represents an aromatic heterocycle, Z
2は芳香族複素環または芳香族炭化水素環を表 し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表 2 represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring, and Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。）  The )
[2] 陰極と陽極との間に発光層を少なくとも有する有機エレクト口ルミネッセンス素子に お 、て、少なくとも 1層に下記一般式（1)で表される化合物の少なくとも 1種を含有し 、且つ電子輸送材料及びドナー化合物を含有する電子輸送層を有することを特徴と する有機エレクト口ルミネッセンス素子。  [2] In an organic electoluminescence device having at least a light emitting layer between a cathode and an anode, at least one layer contains at least one compound represented by the following general formula (1), and an electron An organic electoluminescence device comprising an electron transport layer containing a transport material and a donor compound.
[化 1] 一般式 (1)  [Chemical formula 1] General formula (1)
^101  ^ 101
. - -C ゝ c- -、、 --C ゝ c--,
i \ c -Z3 - C I z2 i \ c -Z 3 -CI z 2
ノ2 2
(式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を表 し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表(In the formula, Z represents an aromatic heterocyclic ring, Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring. Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。）  The )
[3] 電子輸送材料及びドナー化合物を含有する電子輸送層を更に有することを特徴と する請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  [3] The organic electroluminescent device according to claim 1, further comprising an electron transport layer containing an electron transport material and a donor compound.
[4] 前記一般式（1)で表される化合物の Z力 ½員環であることを特徴とする請求の範囲 [4] The Z-membered ring of the compound represented by the general formula (1)
1  1
第 1項に記載の有機エ Iレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to item 1.
[5] 前記一般式（1)で表される化合物の Z力 ½員環であることを特徴とする請求の範囲 [5] The Z-membered ring of the compound represented by the general formula (1)
2  2
第 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to item 1.
[6] 前記一般式（1)で表される化合物の Zが結合手であることを特徴とする請求の範 [6] The compound according to claim 1, wherein Z of the compound represented by the general formula (1) is a bond.
3  Three
囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. An organic electoluminescence device according to item 1.
[7] 前記一般式（1)で表される化合物が分子量 450以上であることを特徴とする請求の 範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 [7] The organic electoluminescence device according to [1], wherein the compound represented by the general formula (1) has a molecular weight of 450 or more.
[8] 前記一般式（1)で表される化合物が下記一般式（1 1)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 [8] The organic electoluminescence device according to [1], wherein the compound represented by the general formula (1) is represented by the following general formula (11).
[化 2]  [Chemical 2]
一般式 (1一 1 )
Figure imgf000102_0001
General formula (1 1 1)
Figure imgf000102_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
501 507  501 507
前記一般式（1)で表される化合物が下記一般式（ 1 2)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (12).
[化 3] 一般式 (1一 2)
Figure imgf000103_0001
[Chemical 3] General formula (1 1 2)
Figure imgf000103_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
511 517  511 517
前記一般式（1)で表される化合物が下記一般式（ 1 3)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (13).
[化 4] [Chemical 4]
一般式 (1—3)
Figure imgf000103_0002
General formula (1-3)
Figure imgf000103_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
521 527  521 527
前記一般式（1)で表される化合物が下記一般式（1 4)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (14).
[化 5] [Chemical 5]
一般式 (1一 4)
Figure imgf000103_0003
General formula (1 1 4)
Figure imgf000103_0003
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） 前記一般式（1)で表される化合物が下記一般式（ 1 5)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 (In the formula, R to R each independently represent a hydrogen atom or a substituent.) 2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (15).
[化 6] 一般式 (1一 5)
Figure imgf000104_0001
[Chemical formula 6] General formula (1 1 5)
Figure imgf000104_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
541 548  541 548
前記一般式（1)で表される化合物が下記一般式（ 1 6)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (16).
[化 7] 一般式 (1一 6)
Figure imgf000104_0002
[Chemical formula 7] General formula (1 1 6)
Figure imgf000104_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
551 558  551 558
[14] 前記一般式（1)で表される化合物が下記一般式（1— 7)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  14. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (1-7).
[化 8] 般式 (1—7)
Figure imgf000105_0001
[Chemical 8] General formula (1-7)
Figure imgf000105_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
561 567  561 567
前記一般式（1)で表される化合物が下記一般式（ 1 8)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (18).
[化 9] [Chemical 9]
—般式 (1—8)
Figure imgf000105_0002
—General formula (1-8)
Figure imgf000105_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
571 577  571 577
前記一般式（1)で表される化合物が下記一般式（ 1 9)で表されることを特徴とす る請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (19).
[化 10] [Chemical 10]
—般式 (1一 9)
Figure imgf000105_0003
—General formula (1 1 9)
Figure imgf000105_0003
(式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) (In the formula, R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different. You may go on. )
前記一般式（1)で表される化合物が下記一般式（1 10)で表されることを特徴と する請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (110).
[化 11] [Chemical 11]
—般式 (1—10) —General formula (1-10)
Figure imgf000106_0001
Figure imgf000106_0001
(式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) (In the formula, R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different.)
前記一般式（1)で表される化合物が下記一般式（2— 1)〜（2— 10)の 、ずれかで 表される基を少なくとも一つ有することを特徴とする請求の範囲第 1項に記載の有機 エレクトロノレミネッセンス素子。  The compound represented by the general formula (1) has at least one group represented by any of the following general formulas (2-1) to (2-10): The organic electroreluminescence element described in the item.
[化 12] [Chemical 12]
一般式 (2— 1 ) -般式 (2— 2)General formula (2— 1)-General formula (2— 2)
Figure imgf000107_0001
Figure imgf000107_0001
-般式 (2— 3) 一般式 (2— 4) -General formula (2-3) General formula (2-4)
Figure imgf000107_0002
Figure imgf000107_0002
-般 -General
Figure imgf000107_0003
Figure imgf000107_0003
-般式 (2— 7) 一般式 (2— 8) -General formula (2—7) General formula (2—8)
Figure imgf000107_0004
Figure imgf000107_0004
-般式 (2— 9) 一般式 (2— 10) -General formula (2— 9) General formula (2— 10)
Figure imgf000107_0005
Figure imgf000107_0005
(式中、 R 〜R 、R 〜R 、R 〜R 、R 〜R 、R 〜R 、R 〜R 、R  (In the formula, R to R, R to R, R to R, R to R, R to R, R to R, R
502 507 512 517 522 527 532 537 542 548 552 558 562 502 507 512 517 522 527 532 537 542 548 552 558 562
〜R 、R 〜R 、R 〜R 、R 〜R は各々独立に水素原子または置換基を表 ~ R, R ~ R, R ~ R, R ~ R each independently represents a hydrogen atom or a substituent.
567 572 577 582 588 592 598  567 572 577 582 588 592 598
し、該置換基は各々同一でもよぐ異なっていてもよい。 ) [19] 前記一般式（1)で表される化合物が下記一般式 (3)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 The substituents may be the same or different. ) [19] The organic electroluminescent device according to item 1 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (3).
[化 13]  [Chemical 13]
Figure imgf000108_0001
Figure imgf000108_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
601 606 601 606 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  601 606 601 606 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
[20] 前記一般式（1)で表される化合物が下記一般式 (4)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  [20] The organic electoluminescence device according to item 1 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (4).
[化 14]  [Chemical 14]
Figure imgf000108_0002
Figure imgf000108_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
611 620 611 620 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  611 620 611 620 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
[21] 前記一般式（1)で表される化合物が下記一般式 (5)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  [21] The organic electroluminescent device according to item 1 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (5).
[化 15] 一般式 (5)
Figure imgf000109_0001
[Chemical 15] General formula (5)
Figure imgf000109_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
621 623 621 623 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  621 623 621 623 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (6)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (6).
[化 16] [Chemical 16]
般式 (6)  General formula (6)
Figure imgf000109_0002
Figure imgf000109_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
631 645 631 645 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  631 645 631 645 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (7)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (7).
[化 17] 一般式 (7) [Chemical 17] General formula (7)
Figure imgf000110_0001
Figure imgf000110_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
651 656 651 656 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの和は 6である。）  651 656 651 656 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but the sum of na and nb is 6. )
前記一般式（1)で表される化合物が下記一般式 (8)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (8).
[化 18] [Chemical 18]
Figure imgf000110_0002
Figure imgf000110_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
661 672 661 672 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  661 672 661 672 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (9)で表されることを特徴とする請 求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 [化 19] 2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (9). [Chemical 19]
一般式 (9)  General formula (9)
Figure imgf000111_0001
Figure imgf000111_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
681 688 681 688 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  681 688 681 688 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式（10)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (10).
[化 20] [Chemical 20]
一般式 (10)
Figure imgf000111_0002
General formula (10)
Figure imgf000111_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表すが、 Lは 2価の連結基 (Wherein R to R each independently represents a hydrogen atom or a substituent, L represents a divalent linking group.
691 700 1  691 700 1
を表す。 R 〜R の少なくとも一つは前記一般式（2— 1)〜（2— 10)で表される基 Represents. At least one of R 1 to R 4 is a group represented by the general formula (2-1) to (2-10).
691 700  691 700
から選ばれる少なくとも一つの基を表す。 ) Represents at least one group selected from )
前記一般式（1)で表される化合物が下記一般式（11)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (11).
[化 21] 一般式 (11)
Figure imgf000112_0001
[Chemical 21] General formula (11)
Figure imgf000112_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（12)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (12).
[化 22] [Chemical 22]
般式 (12)
Figure imgf000112_0002
General formula (12)
Figure imgf000112_0002
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（13)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (13).
[化 23] 般式 (13)
Figure imgf000113_0001
[Chemical 23] General formula (13)
Figure imgf000113_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（14)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 2. The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (14).
[化 24] [Chemical 24]
般式 (14)
Figure imgf000113_0002
General formula (14)
Figure imgf000113_0002
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（15)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 2. The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (15).
[化 25] [Chemical 25]
Figure imgf000114_0001
Figure imgf000114_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 Z K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z
1 1
、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複素環を表す。 ), Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. )
2 3 4 2 3 4
前記一般式（1)で表される化合物が下記一般式（16)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (16).
[化 26] 一般式 (16) [Chemical formula 26] General formula (16)
Figure imgf000114_0002
Figure imgf000114_0002
(式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳 (In the formula, o and p each represent an integer of 1 to 3, and Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複 Represents an aromatic heterocyclic group. Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
1 2  1 2
素環を表し、 Lは 2価の連結基を表す。 ) Represents a prime ring, and L represents a divalent linking group. )
前記一般式（1)で表される化合物が下記一般式（17)で表されることを特徴とする 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  2. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (17).
[化 27] 般式 (17) [Chemical 27] General formula (17)
Figure imgf000115_0001
Figure imgf000115_0001
(式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳  (In the formula, o and p each represent an integer of 1 to 3, and Ar and Ar each represent an arylene group or a divalent aromatic group.
2  2
香族複素環基を表す。 Z、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳  Represents an aromatic heterocyclic group. Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
1 2 3 4  1 2 3 4
香族複素環を表し、 Lは 2価の連結基を表す。 )  Represents an aromatic heterocycle, and L represents a divalent linking group. )
[34] 前記ァクセプター化合物が Au、 Pt、 W、 Ir、 POC1、 AsF、 CI、 Br、 I、 TCNQ、 [34] The acceptor compound is Au, Pt, W, Ir, POC1, AsF, CI, Br, I, TCNQ,
3 6 2 2 2  3 6 2 2 2
TCNQF4、 TCNE、 HCNB、 DDQ、 TNF、 DNF、フルオラ-ル、クロラエル、ブロ マ二ルカ 選ばれることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミ ネッセンス素子。  2. The organic electroluminescent element according to claim 1, wherein TCNQF4, TCNE, HCNB, DDQ, TNF, DNF, fluoral, chlorael, bromilluca are selected.
[35] 前記正孔輸送層が陽極に隣接していることを特徴とする請求の範囲第 1項に記載 の有機エレクト口ルミネッセンス素子。  [35] The organic electoluminescence device according to [1], wherein the hole transport layer is adjacent to the anode.
[36] 前記ドナー化合物がアルカリ金属、アルカリ土類金属もしくはそれらの塩であること を特徴とする請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  [36] The organic electoluminescence device according to [2], wherein the donor compound is an alkali metal, an alkaline earth metal or a salt thereof.
[37] 前記アルカリ金属の塩がセシウムの塩であることを特徴とする請求の範囲第 36項に 記載の有機エレクト口ルミネッセンス素子。  [37] The organic electoluminescence device according to item 36, wherein the alkali metal salt is a cesium salt.
[38] 前記電子輸送層が陰極に隣接していることを特徴とする請求の範囲第 2項に記載 の有機エレクト口ルミネッセンス素子。  [38] The organic electoluminescence device according to [2], wherein the electron transport layer is adjacent to the cathode.
[39] 前記一般式（1)で表される化合物の少なくとも 1種を含有する層が正孔阻止層であ ることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子。  [39] The organic electoluminescence device according to [1], wherein the layer containing at least one compound represented by the general formula (1) is a hole blocking layer.
[40] 発光が白色であることを特徴とする請求の範囲第 1項に記載の有機エレクトロルミネ ッセンス素子。  [40] The organic electroluminescence device according to claim 1, wherein the light emission is white.
[41] 請求の範囲第 40項に記載の有機エレクト口ルミネッセンス素子を有することを特徴 とする表示装置。 [41] The organic electroluminescent device according to claim 40, Display device.
[42] 請求の範囲第 40項に記載の有機エレクト口ルミネッセンス素子を有することを特徴 とする照明装置。  [42] An illumination device comprising the organic electoluminescence element according to claim 40.
[43] 請求の範囲第 42項に記載の照明装置と表示手段としての液晶素子を有することを 特徴とする表示装置。  [43] A display device comprising the illumination device according to claim 42 and a liquid crystal element as display means.
[44] 前記一般式（1)で表 Iさ 5れる化合物の Z力 ½員環であることを特徴とする請求の範囲  [44] The Z-membered ring of the compound represented by Table I in the general formula (1),
1  1
第 2項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to item 2.
[45] 前記一般式（1)で表される化合物の Z力 ½員環であることを特徴とする請求の範囲 [45] The Z-membered ring of the compound represented by the general formula (1).
2  2
第 2項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to item 2.
[46] 前記一般式（1)で表される化合物の Zが結合手であることを特徴とする請求の範 [46] The compound represented by the general formula (1), wherein Z is a bond.
3  Three
囲第 2項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to item 2.
[47] 前記一般式（1)で表される化合物が分子量 450以上であることを特徴とする請求の 範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 [47] The organic electroluminescent device according to claim 2, wherein the compound represented by the general formula (1) has a molecular weight of 450 or more.
[48] 前記一般式（1)で表される化合物が下記一般式（1 1)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 [48] The organic electroluminescence device according to item 2, wherein the compound represented by the general formula (1) is represented by the following general formula (11).
[化 2] 一般式 (1一 1 )
Figure imgf000116_0001
[Chemical formula 2] General formula (1 1 1)
Figure imgf000116_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
501 507  501 507
前記一般式（1)で表される化合物が下記一般式（ 1 2)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (12).
[化 3] 一般式 (1一 2)
Figure imgf000117_0001
[Chemical 3] General formula (1 1 2)
Figure imgf000117_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
511 517  511 517
前記一般式（1)で表される化合物が下記一般式（ 1 3)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (13).
[化 4] [Chemical 4]
一般式 (1—3)
Figure imgf000117_0002
General formula (1-3)
Figure imgf000117_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
521 527  521 527
前記一般式（1)で表される化合物が下記一般式（1 4)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (14).
[化 5] [Chemical 5]
一般式 (1一 4)
Figure imgf000117_0003
General formula (1 1 4)
Figure imgf000117_0003
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） 前記一般式（1)で表される化合物が下記一般式（ 1 5)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 (In the formula, R to R each independently represent a hydrogen atom or a substituent.) 3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (15).
[化 6] 一般式 (1一 5)
Figure imgf000118_0001
[Chemical formula 6] General formula (1 1 5)
Figure imgf000118_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
541 548  541 548
前記一般式（1)で表される化合物が下記一般式（ 1 6)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (16).
[化 7] 一般式 (1一 6)
Figure imgf000118_0002
[Chemical formula 7] General formula (1 1 6)
Figure imgf000118_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
551 558  551 558
[54] 前記一般式（1)で表される化合物が下記一般式（1— 7)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  [54] The organic electroluminescent device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (1-7).
[化 8] 般式 (1—7)
Figure imgf000119_0001
[Chemical 8] General formula (1-7)
Figure imgf000119_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
561 567  561 567
前記一般式（1)で表される化合物が下記一般式（ 1 8)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (18).
[化 9] [Chemical 9]
—般式 (1—8)
Figure imgf000119_0002
—General formula (1-8)
Figure imgf000119_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す。） (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
571 577  571 577
前記一般式（1)で表される化合物が下記一般式（ 1 9)で表されることを特徴とす る請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (19).
[化 10] [Chemical 10]
—般式 (1一 9)
Figure imgf000119_0003
—General formula (1 1 9)
Figure imgf000119_0003
(式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) (In the formula, R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different. You may go on. )
前記一般式（1)で表される化合物が下記一般式（1 10)で表されることを特徴と する請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (110).
[化 11] [Chemical 11]
—般式 (1—10) —General formula (1-10)
Figure imgf000120_0001
Figure imgf000120_0001
(式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) (In the formula, R represents a hydrogen atom or a substituent, and a plurality of R may be the same or different.)
前記一般式（1)で表される化合物が下記一般式（2— 1)〜（2— 10)の 、ずれかで 表される基を少なくとも一つ有することを特徴とする請求の範囲第 2項に記載の有機 エレクトロノレミネッセンス素子。  The compound represented by the general formula (1) has at least one group represented by any of the following general formulas (2-1) to (2-10): The organic electroreluminescence element described in the item.
[化 12] [Chemical 12]
一般式 (2— 1 ) -般式 (2— 2)General formula (2— 1)-General formula (2— 2)
Figure imgf000121_0001
Figure imgf000121_0001
-般式 (2— 3) 一般式 (2— 4) -General formula (2-3) General formula (2-4)
Figure imgf000121_0002
Figure imgf000121_0002
-般 -General
Figure imgf000121_0003
Figure imgf000121_0003
-般式 (2— 7) 一般式 (2— 8) -General formula (2—7) General formula (2—8)
Figure imgf000121_0004
Figure imgf000121_0004
-般式 (2— 9) 一般式 (2— 10) -General formula (2— 9) General formula (2— 10)
Figure imgf000121_0005
Figure imgf000121_0005
(式中、 R 〜R 、R 〜R 、R 〜R 、R 〜R 、R 〜R 、R 〜R 、R  (In the formula, R to R, R to R, R to R, R to R, R to R, R to R, R
502 507 512 517 522 527 532 537 542 548 552 558 562 502 507 512 517 522 527 532 537 542 548 552 558 562
〜R 、R 〜R 、R 〜R 、R 〜R は各々独立に水素原子または置換基を表 ~ R, R ~ R, R ~ R, R ~ R each independently represents a hydrogen atom or a substituent.
567 572 577 582 588 592 598  567 572 577 582 588 592 598
し、該置換基は各々同一でもよぐ異なっていてもよい。 ) [59] 前記一般式（1)で表される化合物が下記一般式 (3)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 The substituents may be the same or different. ) [59] The organic electroluminescent device according to item 2 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (3).
[化 13]  [Chemical 13]
Figure imgf000122_0001
Figure imgf000122_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
601 606 601 606 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  601 606 601 606 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
[60] 前記一般式（1)で表される化合物が下記一般式 (4)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  [60] The organic electroluminescent device according to item 2 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (4).
[化 14]  [Chemical 14]
Figure imgf000122_0002
Figure imgf000122_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
611 620 611 620 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  611 620 611 620 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
[61] 前記一般式（1)で表される化合物が下記一般式 (5)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  [61] The organic electroluminescent device according to item 2 of the claim, wherein the compound represented by the general formula (1) is represented by the following general formula (5).
[化 15] 一般式 (5)
Figure imgf000123_0001
[Chemical 15] General formula (5)
Figure imgf000123_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
621 623 621 623 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  621 623 621 623 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (6)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electroluminescent device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (6).
[化 16] [Chemical 16]
般式 (6)  General formula (6)
Figure imgf000123_0002
Figure imgf000123_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
631 645 631 645 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  631 645 631 645 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (7)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electroluminescent device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (7).
[化 17] 一般式 (7) [Chemical 17] General formula (7)
Figure imgf000124_0001
Figure imgf000124_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
651 656 651 656 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの和は 6である。）  651 656 651 656 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but the sum of na and nb is 6. )
前記一般式（1)で表される化合物が下記一般式 (8)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electroluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (8).
[化 18] [Chemical 18]
Figure imgf000124_0002
Figure imgf000124_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
661 672 661 672 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  661 672 661 672 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式 (9)で表されることを特徴とする請 求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 [化 19] 3. The organic electroluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (9). [Chemical 19]
一般式 (9)  General formula (9)
Figure imgf000125_0001
Figure imgf000125_0001
(式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な (In the formula, R to R each independently represents a small amount of force R to R representing a hydrogen atom or a substituent.
681 688 681 688 くとも一つは前記一般式（2— 1)〜（2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  681 688 681 688 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
前記一般式（1)で表される化合物が下記一般式（10)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (10).
[化 20] [Chemical 20]
一般式 (10)
Figure imgf000125_0002
General formula (10)
Figure imgf000125_0002
(式中、 R 〜R は各々独立に水素原子または置換基を表すが、 Lは 2価の連結基 (Wherein R to R each independently represents a hydrogen atom or a substituent, L represents a divalent linking group.
691 700 1  691 700 1
を表す。 R 〜R の少なくとも一つは前記一般式（2— 1)〜（2— 10)で表される基 Represents. At least one of R 1 to R 4 is a group represented by the general formula (2-1) to (2-10).
691 700  691 700
から選ばれる少なくとも一つの基を表す。 ) Represents at least one group selected from )
前記一般式（1)で表される化合物が下記一般式（11)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (11).
[化 21] 一般式 (11)
Figure imgf000126_0001
[Chemical 21] General formula (11)
Figure imgf000126_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（12)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (12).
[化 22] [Chemical 22]
般式 (12)
Figure imgf000126_0002
General formula (12)
Figure imgf000126_0002
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（13)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (13).
[化 23] 般式 (13)
Figure imgf000127_0001
[Chemical 23] General formula (13)
Figure imgf000127_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（14)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (14).
[化 24] [Chemical 24]
般式 (14)
Figure imgf000127_0002
General formula (14)
Figure imgf000127_0002
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 ) 前記一般式（1)で表される化合物が下記一般式（15)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. 3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (15).
[化 25] [Chemical 25]
Figure imgf000128_0001
Figure imgf000128_0001
(式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 (In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、且つ l+m= 5である。 Z K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z
1 1
、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複素環を表す。 ), Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. )
2 3 4 2 3 4
前記一般式（1)で表される化合物が下記一般式（16)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  3. The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (16).
[化 26] 一般式 (16) [Chemical formula 26] General formula (16)
Figure imgf000128_0002
Figure imgf000128_0002
(式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳 (In the formula, o and p each represent an integer of 1 to 3, and Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複 Represents an aromatic heterocyclic group. Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
1 2  1 2
素環を表し、 Lは 2価の連結基を表す。 ) Represents a prime ring, and L represents a divalent linking group. )
前記一般式（1)で表される化合物が下記一般式（17)で表されることを特徴とする 請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to claim 2, wherein the compound represented by the general formula (1) is represented by the following general formula (17).
[化 27] 般式 (17) [Chemical 27] General formula (17)
Figure imgf000129_0001
Figure imgf000129_0001
(式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳  (In the formula, o and p each represent an integer of 1 to 3, and Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳  Represents an aromatic heterocyclic group. Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
1 2 3 4  1 2 3 4
香族複素環を表し、 Lは 2価の連結基を表す。 )  Represents an aromatic heterocycle, and L represents a divalent linking group. )
[74] 前記一般式（1)で表される化合物の少なくとも 1種を含有する層が正孔阻止層であ ることを特徴とする請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子。 74. The organic electroluminescent device according to claim 2, wherein the layer containing at least one compound represented by the general formula (1) is a hole blocking layer.
[75] 発光が白色であることを特徴とする請求の範囲第 2項に記載の有機エレクトロルミネ ッセンス素子。 [75] The organic electroluminescence device according to claim 2, wherein the light emission is white.
[76] 請求の範囲第 75項に記載の有機エレクト口ルミネッセンス素子を有することを特徴 とする表示装置。  [76] A display device comprising the organic electoluminescence device according to claim 75.
[77] 請求の範囲第 75項に記載の有機エレクト口ルミネッセンス素子を有することを特徴 とする照明装置。  [77] An illuminating device comprising the organic electoluminescence device according to claim 75.
[78] 請求項 77に記載の照明装置と表示手段としての液晶素子を有することを特徴とす  [78] The illumination device according to claim 77, and a liquid crystal element as display means
PCT/JP2005/018672 2004-10-19 2005-10-11 Organic electroluminescent device, display and illuminating device WO2006043440A1 (en)

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KR101400387B1 (en) 2010-10-29 2014-05-27 엘지디스플레이 주식회사 Phosphorescent material for Organic electroluminescent device
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WO2011024976A1 (en) * 2009-08-31 2011-03-03 富士フイルム株式会社 Organic electroluminescent element
JP2011071461A (en) * 2009-08-31 2011-04-07 Fujifilm Corp Organic electroluminescent element
US9045471B2 (en) 2010-10-28 2015-06-02 Lg Display Co., Ltd. Phosphorescent compound and organic electroluminescent device using the same
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KR101400387B1 (en) 2010-10-29 2014-05-27 엘지디스플레이 주식회사 Phosphorescent material for Organic electroluminescent device
KR101792099B1 (en) * 2010-11-09 2017-10-31 엘지디스플레이 주식회사 Phosphorescent material for Organic electroluminescent device

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