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WO2006043440A1 - Dispositif électroluminescent organique, afficheur et dispositif d’éclairage - Google Patents

Dispositif électroluminescent organique, afficheur et dispositif d’éclairage 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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Japanese (ja)
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Shuichi Sugita
Hiroshi Kita
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Konica Minolta Inc
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Konica Minolta Inc
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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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  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant au moins une couche émettrice de lumière entre une cathode et une anode, qui est caractérisé en ce qu’il comprend au moins une couche contenant au moins un composé représenté par la formule générale (1) ci-dessous et une couche de transport de trous contenant un matériau de transport de trous et un composé accepteur. (Dans la formule, Z1 représente un noyau hétérocyclique aromatique, Z2 représente un noyau hétérocyclique aromatique ou un anneau d’hydrocarbure aromatique, Z3 représente un groupe de liaison divalent ou un élément de liaison et R101 représente un atome d’hydrogène ou un substituant.)
PCT/JP2005/018672 2004-10-19 2005-10-11 Dispositif électroluminescent organique, afficheur et dispositif d’éclairage Ceased WO2006043440A1 (fr)

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
WO2011024976A1 (fr) * 2009-08-31 2011-03-03 富士フイルム株式会社 Elément électroluminescent organique
JP2011071461A (ja) * 2009-08-31 2011-04-07 Fujifilm Corp 有機電界発光素子
KR101400387B1 (ko) 2010-10-29 2014-05-27 엘지디스플레이 주식회사 유기전계발광소자용 인광 물질
US9045471B2 (en) 2010-10-28 2015-06-02 Lg Display Co., Ltd. Phosphorescent compound and organic electroluminescent device using the same
KR101792099B1 (ko) * 2010-11-09 2017-10-31 엘지디스플레이 주식회사 유기전계발광소자용 인광 물질

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CN115819430A (zh) * 2023-02-07 2023-03-21 烟台显华科技集团股份有限公司 一种氮杂二苯并五元环化合物及其应用

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JP2001244079A (ja) * 2000-02-29 2001-09-07 Junji Kido 有機エレクトロルミネッセント素子、有機エレクトロルミネッセント素子群及びその発光スペクトルの制御方法
WO2004053019A1 (fr) * 2002-12-12 2004-06-24 Idemitsu Kosan Co., Ltd. Materiau pour dispositif electroluminescent organique et dispositif electroluminescent organique utilisant un tel materiau
WO2004074399A1 (fr) * 2003-02-20 2004-09-02 Idemitsu Kosan Co., Ltd. Matiere pour dispositifs electroluminescents organiques, et dispositif electroluminescent organique comportant une telle matiere

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JPH04297076A (ja) * 1991-01-31 1992-10-21 Toshiba Corp 有機ｅｌ素子
JP2001244079A (ja) * 2000-02-29 2001-09-07 Junji Kido 有機エレクトロルミネッセント素子、有機エレクトロルミネッセント素子群及びその発光スペクトルの制御方法
WO2004053019A1 (fr) * 2002-12-12 2004-06-24 Idemitsu Kosan Co., Ltd. Materiau pour dispositif electroluminescent organique et dispositif electroluminescent organique utilisant un tel materiau
WO2004074399A1 (fr) * 2003-02-20 2004-09-02 Idemitsu Kosan Co., Ltd. Matiere pour dispositifs electroluminescents organiques, et dispositif electroluminescent organique comportant une telle matiere

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011024976A1 (fr) * 2009-08-31 2011-03-03 富士フイルム株式会社 Elément électroluminescent organique
JP2011071461A (ja) * 2009-08-31 2011-04-07 Fujifilm Corp 有機電界発光素子
US9045471B2 (en) 2010-10-28 2015-06-02 Lg Display Co., Ltd. Phosphorescent compound and organic electroluminescent device using the same
US9240559B2 (en) 2010-10-28 2016-01-19 Lg Display Co., Ltd. Phosphorescent compound and organic electroluminescent device using the same
DE102011054855B4 (de) 2010-10-28 2019-07-11 Lg Display Co., Ltd. Phosphoreszierende Verbindung und diese verwendende organische elektrolumineszente Vorrichtung
DE102011123066B3 (de) 2010-10-28 2023-04-06 Lg Display Co., Ltd. Phosphoreszierende Verbindung und diese verwendende organische elektrolumineszente Vorrichtung
KR101400387B1 (ko) 2010-10-29 2014-05-27 엘지디스플레이 주식회사 유기전계발광소자용 인광 물질
KR101792099B1 (ko) * 2010-11-09 2017-10-31 엘지디스플레이 주식회사 유기전계발광소자용 인광 물질

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