WO2005097943A1 - Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, écran et dispositif d'éclairage - Google Patents

Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, écran et dispositif d'éclairage Download PDF

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WO2005097943A1
WO2005097943A1 PCT/JP2005/004683 JP2005004683W WO2005097943A1 WO 2005097943 A1 WO2005097943 A1 WO 2005097943A1 JP 2005004683 W JP2005004683 W JP 2005004683W WO 2005097943 A1 WO2005097943 A1 WO 2005097943A1
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organic
organic electroluminescent
electroluminescent device
layer
general formula
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PCT/JP2005/004683
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Japanese (ja)
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Tomohiro Oshiyama
Eisaku Katoh
Hiroshi Kita
Shuichi Oi
Yoshio Inoue
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Konica Minolta Holdings, Inc.
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Priority to JP2006511956A priority Critical patent/JP5045100B2/ja
Publication of WO2005097943A1 publication Critical patent/WO2005097943A1/fr

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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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
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    • 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
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    • 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
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • H—ELECTRICITY
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    • 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
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
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    • 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
    • H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • 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
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • Organic electroluminescent device organic electroluminescent device
  • the present invention relates to a material for an organic electroluminescent device, a device for an organic electroluminescent device, a display device, and a lighting device.
  • ELD electroluminescent display
  • examples of ELD components include an inorganic electroluminescent device and an organic electroluminescent device (hereinafter, referred to as an organic EL device).
  • Inorganic electroluminescent devices have been used as flat light sources, but high voltage AC is required to drive the light emitting devices.
  • 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. Electrons and holes are injected into the light-emitting layer and recombined to generate excitons (exciton).
  • a stilbene derivative, a distyrylarylene derivative or a tris styrylarylene derivative is doped with a small amount of a phosphor to achieve an improvement in light emission luminance and a long life of the device. .
  • an element having an organic light-emitting layer obtained by using an 8-hydroxyquinoline aluminum complex as a host conjugate and adding a small amount of a phosphor thereto for example, JP-A-63-264692
  • a device having an organic light emitting layer in which a quinoline aluminum complex is used as a host conjugate and doped with a quinacridone dye for example, JP-A-3-255190
  • the upper limit of the internal quantum efficiency is 100%, so that the luminous efficiency is twice as high as that of the excited singlet, and performance almost equivalent to that of a cold cathode tube is not obtained. Because of the possibility that it may be used, it is attracting attention as a lighting application.
  • the light emission luminance and the light emission efficiency of the light emitting element are greatly improved as compared with the conventional element because the emitted light is derived from phosphorescence. There is a problem that the light lifetime is shorter than that of the conventional device.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2002-332291
  • Patent Document 2 JP-A-2002-332292
  • Patent Document 3 JP-A-2002-338588
  • Patent Document 4 JP 2002-226495 A
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-234894
  • Patent Document 6 International Publication No. 02Z15645 pamphlet
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2003-123982
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2002-117978
  • Patent Document 9 Japanese Patent Application Laid-Open No. 2003-146996
  • Patent Document 10 International Publication No. 04Z016711 pamphlet
  • Non-Patent Document 1 Inorganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002)
  • Non-patent document 2 Applied Physics Letters, Vol. 79, page 2082 (2001)
  • Non-patent document 3 Applied Physics Letters, Vol. 83, page 3818 (2003)
  • Non-patent document 4 New Journal of Chemistry, 26 Vol., P. 1171 (2002) Disclosure of the Invention
  • An object of the present invention is to provide an organic EL element, a lighting device, and a display device in which the emission wavelength is controlled, high luminous efficiency is exhibited, and luminescence life is long.
  • One embodiment of the present invention for achieving the above object is an organic electroluminescent device material comprising a metal complex having a partial structure represented by the following general formula (1). is there.
  • FIG. 1 is a schematic diagram showing an example of a display device configured with an organic EL element.
  • FIG. 2 is a schematic diagram of a display unit A.
  • FIG. 3 is an equivalent circuit diagram of a drive circuit forming a pixel.
  • FIG. 4 is a schematic view of a display device using a passive matrix system.
  • FIG. 5 is a schematic diagram of a sealing structure of an organic EL element OLED1-1.
  • FIG. 6 is a schematic view of a lighting device including an organic EL element.
  • An organic electroluminescent device material comprising a metal complex having a partial structure represented by the following general formula (1). —General formula (1)
  • R, R, R, R are hydrogen atoms or
  • M represents an element of Group 8, 9 or 10 in the periodic table.
  • Ra represents a substituent.
  • Xa represents an oxygen atom, a sulfur atom, or a nitrogen atom.
  • Na represents 1 or 2.
  • Rb, Rc, and Rd represent substituents, and Xb, Xc, and Xd represent an oxygen atom, a sulfur atom, or a nitrogen atom. Represents an elementary atom.
  • nb, nc, and nd represent 1 or 2.
  • R, R, R, R, R are hydrogen atoms or
  • M represents an element in group 8, 9 or 10 of the periodic table
  • Xd is a nitrogen atom
  • Xb and Xc are oxygen atoms.
  • the organic electroluminescent device material according to (1) or (2).
  • An organic electroluminescence device comprising the organic electroluminescence device according to any one of (1) to (9).
  • An organic electroluminescent device having a light-emitting layer as a constituent layer, wherein the light-emitting layer contains the organic electroluminescent device material described in (1) above.
  • a luminescence element A luminescence element.
  • An organic electroluminescence device comprising the organic electroluminescent device material according to claim 1.
  • a display device comprising the organic electroluminescent element according to any one of (10) to (12).
  • a lighting device comprising the organic electroluminescent element according to any one of (10) to (12).
  • the present inventors conducted studies based on the above guidelines as a means for shortening the emission wavelength to blue, and performed synthesis studies. As a result, control of the emission wavelength that almost satisfied the simulation results was performed. I can do it.
  • substituents such as alkylthio and arylthio groups have a small electron donating property, but the effect of improving the life is significantly increased. This is presumed to be because the electronic properties of these substituents have a function equivalent to that of a ⁇ -electron donating group due to the lawn pair present in the alkylthio group and arylthio group substituents.
  • the strong ⁇ property and the presence of at least two electron-donating groups in the molecule as a substituent can improve the lifetime of the light-emitting element even when an electron-withdrawing group is introduced at the 3 ⁇ -position or 5 ⁇ -position. I was helping.
  • Gaussian 98 (Revision A. 11.4, M. J. Frisch, G.
  • the phosphorescence wavelength was calculated by TD-DFT calculation, and the emission wavelength was obtained.
  • the layer containing the metal complex is preferably a light emitting layer and a Z or hole blocking layer.
  • the light emitting layer by using it as a light emitting dopant in the light emitting layer, it is possible to achieve an object of the present invention, that is, a longer light emitting life of the organic EL element.
  • the metal complex represented by the general formula (1) according to the present invention will be described.
  • A, B, and C each represent a force represented by a hydrogen atom or a substituent. At least two of them are represented by the general formula (2) and may be different from each other.
  • the substituents represented by A, B, and C are not particularly limited, but are preferably alkyl groups (for example, methyl group, isopropyl group, tert-butyl group, etc.), cycloalkyl groups (for example, cyclohexyl group, Cyclopentyl group, cyclopropyl group, etc.), alkenyl group (eg, butyl group, aryl group, 2-butenyl group, etc.), alkyl group (eg, ethur group, propynyl group, etc.), aryl group (eg, Phenyl, 2-naphthyl, 9-phenanthryl, 2-pyridyl, 2-chel, 3-furyl, mesityl, carbazolyl, fluoren
  • a silyl group eg, a triphenylsilyl group, a trimethylsilyl group, etc.
  • an amino group an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group and an aryl group.
  • an amino group an alkoxy group and an alkylthio group.
  • R, R, R, R, and R represent a hydrogen atom or a substituent.
  • R, R, and the substituents represented by R are described as the substituents represented by A, B, and C above. Synonymous with As the substituent represented by R or R, an electron withdrawing group (in the present invention,
  • the Hammett's ⁇ ⁇ value according to the present invention refers to Hammett's substituent constant ⁇ ⁇ .
  • the value of ⁇ ⁇ of Noh and Met is a substituent constant for which the electronic effect of the substituent on the hydrolysis of ethyl benzoate was determined by Hammett et al., “Structure-activity relationship of drugs” (Nan-Edo: 1979) And “SuDstituent Constants for Correlation Analysis chemistry and biology” (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979) and the like can be cited.
  • the following is an example of an electron-withdrawing group having ⁇ ⁇ of 0.10 or more.
  • ⁇ ⁇ force ⁇ examples of electron-withdrawing groups of 10 or more include, for example, ⁇ ( ⁇ ) (0.12),
  • M represents an element belonging to Group 8, 9 or 10 in the periodic table.
  • the Group 8, 9 or 10 element is preferably ruthenium, rhodium, palladium, osmium, iridium and platinum, most preferably iridium and platinum.
  • Ra represents a substituent.
  • the substituent represented by Ra has the same meaning as that described for the substituent represented by A, B, or C. Of these, an alkyl group is particularly preferred.
  • Xa represents an oxygen atom, a sulfur atom or a nitrogen atom.
  • na is 1 Or 2
  • the metal complex represented by the general formula (3) according to the present invention will be described.
  • Rb, Rc, and Rd represent substituents, and the substituents represented by Rb, Rc, and Rd include A and B in the general formula (1). Has the same meanings as those described for the substituent represented by C.
  • the substituent for Rb, Rc and Rd is preferably an alkyl group.
  • Xb, Xc and Xd represent an oxygen atom, a sulfur atom or a nitrogen atom.
  • Xb, Xc and Xd are (l) Xd is a nitrogen atom, Xb and Xc are oxygen atoms, (2) Xd is a sulfur atom, and Xb and Xc are oxygen atoms or (3) Xb, Xc and Xd are preferably oxygen atoms.
  • nb, nc, and nd represent 1 or 2.
  • R, R, R, R, and R represent a hydrogen atom or a substituent.
  • R, R, and R represent the substituents represented by A, B, and C in the general formula (1).
  • M is an element of Group 8, 9 or 10 in the periodic table.
  • the Group 8, 9 or 10 element is preferably ruthenium, rhodium, palladium, osmium, iridium and platinum, most preferably iridium and platinum.
  • the organic EL element containing the above-mentioned organic EL element material means that the organic EL element material forms any of the organic layers constituting the organic EL element, or Represents the organic EL element contained in
  • the organic EL device material is preferably contained in the light emitting layer or the hole blocking layer.
  • the luminescent dopant (simply referred to as a dopant) and the luminescent host (simply referred to as a host) will be described.
  • a main component is called a host and other components are called a dopant, and represented by the general formula (1) according to the present invention.
  • Compounds are used as luminescent dopants.
  • the mixing ratio of the dopant to the host compound is preferably 0.
  • the light emitting dopant may be a mixture of a plurality of types of compounds.
  • the mixture may be made of a group 8, 9, or 10 metal complex having a different structure, or other phosphorescent compounds. It may be a dopant or a fluorescent dopant.
  • Light-emitting dopants are roughly classified into two types: fluorescent dopants that emit fluorescence and phosphorescent dopants that emit phosphorescence.
  • Representative examples of the former include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squarium dyes, and oxobenzanthracene dyes
  • fluorescein dyes rhodamine dyes
  • pyrylium dyes perylene dyes
  • stylbene dyes polythiophene dyes
  • rare earth complex fluorescent materials and other known fluorescent compounds.
  • Representative examples of the latter are preferably complex compounds containing a metal of Group 8, 9 or 10 in the periodic table of the elements, and more preferably an iridium compound. , Osmium compounds, palladium compounds or platinum compounds (platinum complex compounds
  • a light-emitting host (also referred to simply as a host!) Means a compound having the highest mixing ratio (mass) in a light-emitting layer composed of two or more compounds, and the other compounds are referred to as “do”.
  • One panto compound also simply referred to as a dopant
  • the luminescent host used in the present invention a compound having a shorter wavelength than the phosphorescent 0-0 band of the luminescent dopant used in combination is preferred, and the luminescent dopant is preferably the phosphorescent 0-0 band.
  • the emission host preferably has a phosphorescent 0-0 band power of 50 nm or less.
  • the luminescent host used in the present invention is not particularly limited in structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing complex ring compound, or thiophene.
  • a compound having a basic skeleton such as a derivative, a furan derivative, or an oligoarylene conjugate, and having the above-mentioned 0-0 band of 450 nm or less is preferable, and examples of the compound are U and conjugate.
  • the luminescent host used in the present invention may be a low-molecular compound or a high-molecular compound having a repeating unit, and may be a low-molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation-polymerizable luminescence). Host)
  • a compound that has a hole-transporting ability and an electron-transporting ability, prevents a longer emission wavelength, and has a high Tg (glass transition temperature) is preferable.
  • anode in the organic EL device a material having a large work function (4 eV or more), such as a metal, an alloy, an electrically conductive compound, and a mixture thereof is preferably used.
  • an electrode material include metals such as Au, and conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO. Also, IDIXO (In O ZnO) etc.
  • a material that is amorphous and can form a transparent conductive film may be used.
  • the anode is made of these electrode materials
  • a thin film is formed by a method such as evaporation or sputtering, and a pattern of a desired shape can be formed by a photolithography method, or when pattern accuracy is not required very much (about 100 ⁇ m or more) Alternatively, a pattern may be formed through a mask having a desired shape during the deposition or sputtering of the electrode material.
  • the transmittance be greater than 10%, and the sheet resistance of the anode is preferably several hundred ⁇ aperture or less.
  • the film thickness is selected within the range of usually 10-1000 nm, preferably 10-200 nm, depending on the material.
  • a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as an electrode material.
  • an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, a mixture of magnesium and copper, a mixture of magnesium and silver, a mixture of magnesium and aluminum, a mixture of indium and magnesium, and a mixture of aluminum and aluminum. (Al 2 O 3) mixture, indium, lithium Z aluminum mixture, rare earth metal, etc.
  • a mixture of an electron-injecting metal and a second metal that is a metal having a large work function and a stable work function such as a magnesium Z-silver mixture, from the viewpoint of the electron-injecting property and the durability against oxidation and the like.
  • a magnesium Z-silver mixture a metal having a large work function and a stable work function, such as a magnesium Z-silver mixture.
  • the cathode can be manufactured by forming a thin film from these electrode substances by a method such as evaporation or sputtering. Further, the sheet resistance as the cathode is preferably several hundred ⁇ / square or less, and the preferred film thickness is usually selected in the range of lOnm-1000 nm, preferably 50 nm-200 nm. In order to transmit light, if either the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is advantageously improved.
  • Injection layer >>: electron injection layer, hole injection layer
  • the injection layer is provided as necessary, and has an electron injection layer and a hole injection layer. It may be present between the light emitting layer or the hole transporting layer and between the cathode and the light emitting layer or the electron transporting layer.
  • the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the light emission luminance, and is referred to as "the organic EL element and its forefront of industrial technology (November 30, 1998 The details are described in Chapter 2, Chapter 2, “Electrode Materials” (pages 123-166) of Vol. 2, No. 2, pp. 123-166, and the hole injection layer (anode buffer layer) and the electron injection layer (cathode buffer). One).
  • the anode buffer layer (hole injection layer) is described in detail in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like.
  • Copper phthalate One layer of phthalocyanine buffer typified by cyanine, one layer of oxide buffer typified by vanadium oxide, one layer of amorphous carbon buffer, polymer buffer using conductive polymer such as polyaline (emeraldine) or polythiophene And one layer.
  • cathode buffer electro injection layer
  • metal buffer represented by strontium ⁇ aluminum
  • alkali metal compound buffer represented by lithium fluoride
  • alkaline earth metal compound buffer represented by magnesium fluoride
  • aluminum oxide a buffer layer of the oxidizing substance to be used.
  • the thickness of the buffer layer is preferably in the range of 0.1 nm to 100 nm, although it depends on the desired material.
  • the blocking layer is provided as necessary in addition to the basic constituent layers of the organic compound thin film as described above.
  • the hole blocking layer is, in a broad sense, an electron transporting layer, a material that has a function of transporting electrons and has an extremely small ability to transport holes, and blocks holes while transporting electrons. This can improve the probability of recombination between electrons and holes.
  • an electron blocking layer is a hole transporting layer in a broad sense, and is a material having a very small ability to transport electrons while having a function of transporting holes. Obstruction By stopping, the recombination probability of electrons and holes can be improved.
  • the hole transport layer is made of a 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 injection layer can be formed by applying a thin film to the above-mentioned material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method.
  • the thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm.
  • the injection layer may have a single-layer structure in which one or more of the above-mentioned materials are used.
  • the group VIII metal complex of the present invention is preferably used as a luminescent dopant, but other known luminescent hosts and luminescent dopants may be used in combination.
  • Examples of the known light-emitting host that may be used in combination include an electron transporting material and a hole transporting material described below as preferable examples thereof, and when applied to a blue or white light-emitting element, a display device, and a lighting device.
  • the maximum fluorescence wavelength is preferably 415 nm or less, and the 0-0 band of phosphorescence is more preferably 450 nm or less.
  • This light emitting layer can be formed by forming the above compound by a known thin film forming method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method.
  • the thickness of the light emitting layer is not particularly limited, but is usually selected in the range of 5 nm to 5 ⁇ m.
  • the light-emitting layer may have a single-layer structure in which one or two or more of these light-emitting materials are used, or may have a stacked structure including a plurality of layers having the same composition or different compositions.
  • this light-emitting layer is formed by dissolving the light-emitting material together with a binder such as resin in a solvent to form a solution, and then spinning the solution.
  • the thin film can be formed by a coating method or the like.
  • the thickness of the light emitting layer thus formed is usually in the range of 5 nm to 5 ⁇ m.
  • the hole transport layer is made of a 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 may be provided as a single layer or a plurality of layers.
  • the hole transporting material is not particularly limited. Any material can be selected from those commonly used as injection / transport materials and known materials used for the hole injection layer and the hole transport layer of the EL element.
  • the hole transporting material has a hole injection / transport and / or electron barrier property, and may be either an organic substance or an inorganic substance.
  • triazole derivatives oxazidazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, furylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives , Stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the hole-transporting material As the hole-transporting material, the above-mentioned materials can be used. It is preferable to use porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds. ,.
  • aromatic tertiary amylide and the styrylamine diary include N, N, N ', N'-tetraphenyl-4,4'-diaminophenol; N, N '—Diphenyl N, N'-bis (3-methylphenyl) — [1,1'-biphenyl] 4,4'diamine (TPD); 2,2-bis (4-zy p-tolylaminophenol ) Propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ', N'-tetra-p-tolyl 4,4'diaminobiphenyl; 1,1bis ( 4-G-p-tolylaminophenyl) 4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-g-p-tolylaminophenyl)
  • Pat. No. 5,061,569 which has two condensed aromatic rings in the molecule, for example, 4,4'bis [N-(1naphthyl) N phenylamino] Bi-Fuel (NPD), a 3-star burst type tri-fluoramine unit described in JP-A-4-308688 4,4 ', A "-tris [? ⁇ -(3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) and the like.
  • NPD 4,4'bis [N-(1naphthyl) N phenylamino] Bi-Fuel
  • MTDATA triphenylamine
  • a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used 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 material of the hole transport layer preferably has a fluorescence maximum wavelength of 415 nm or less when applied to a blue or white light emitting element, a display device, and a lighting device. More preferably, the 0-0 band power of the phosphorescent light is 50 nm or less.
  • the hole transport material is preferably a compound having a high Tg.
  • This hole transport layer is formed by thinning the above-mentioned hole transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method. be able to.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 to 5000 nm.
  • the hole transport layer may have a single-layer structure made of one or more of the above materials.
  • the electron transport layer is a material having a function of transporting electrons.
  • an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided as a single layer or a plurality of layers.
  • the Group VIII metal complex of the present invention for the hole blocking layer, but in addition to these, a known electron transporting material (also serving as a hole blocking material) may be used in combination. A little bit.
  • the electron transporting material also serving as a hole blocking material
  • the electron transporting material used for an electron transporting layer having a single layer and an electron transporting layer adjacent to the light emitting layer on the cathode side with respect to the light emitting layer includes the following.
  • the above materials are known.
  • the electron transporting layer may be any material that has been selected from conventionally known compounds as long as it has a function of transmitting electrons injected from the cathode to the light emitting layer. You can be there.
  • electron transport material examples include heterocyclic substituted fluorene derivatives, difluoroquinone derivatives, thiopyrandioxide derivatives, and naphthalene perylene.
  • examples include tetracarboxylic anhydride, carbodiimide, fluorenylidene methane derivative, anthraquinodimethane and anthrone derivative, oxaziazole derivative and the like.
  • a thiadiazole derivative in which an 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 the electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain, can also be used.
  • metal complexes of 8-quinolinol derivatives for example, tris (8-quinolinol) aluminum- (Alq), tris (5,7-dichrolic-8-quinolinol) aluminum, tris (5,7-dibromo
  • Metal complexes that replace Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • metal-free or metal phthalocyanine, or those whose terminals are substituted with an alkyl group ⁇ sulfonic acid group or the like can be preferably used as the electron transporting material.
  • the distyryl virazine derivative exemplified as the material of the light emitting layer can be used as the electron transporting material, and like the hole injection layer and the hole transporting layer, n-type Si, n-type SiC, etc.
  • Inorganic semiconductors can also be used as electron transport materials.
  • the fluorescent maximum wavelength is preferably 415 nm or less.
  • the zero band force is 50 nm or less.
  • the compound used for the electron transport layer a compound having a high Tg is preferable.
  • the electron transporting layer is formed by thinning the electron transporting material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an inkjet method, and an LB method. Can.
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 to 5000 nm.
  • the electron transport layer may have a single-layer structure made of one or more of the above materials.
  • the substrate for the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent. And a light-transmitting resin film.
  • Particularly preferred V is a resin film that can provide flexibility to the organic EL device.
  • Examples of the resin film include, but are not particularly limited to, polyesters such as polyethylene terephthalate and polyethylene naphthalate, polyethylene, polypropylene, cellophane, senorelose diacetate, senorelostriacetate, senorelose acetate butyrate, and senolle.
  • polyesters such as polyethylene terephthalate and polyethylene naphthalate, polyethylene, polypropylene, cellophane, senorelose diacetate, senorelostriacetate, senorelose acetate butyrate, and senolle.
  • Cellulose esters such as Loose acetate propionate, Senolerose acetate phthalate, Senolerose nitrate or derivatives thereof, polychlorinated bilidene, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, poly Methylpentene, polyetherketone, polyimide, polyethersulfone, polysulfones, polyetherketoneimide, polya De, fluorine resin, nylon, polymethyl methacrylate, acrylic or polyarylate, Arton (trade name: manufactured by JSR Corporation) or Abel (trade name: manufactured by Mitsui Chemicals, Inc.)!
  • Examples include norbornene (or cycloolefin) resin, organic-inorganic hybrid resin, and the like.
  • Examples of the organic-inorganic hybrid resin include those obtained by combining an inorganic polymer (for example, silica, alumina, titer, zirconia, and the like) obtained by an organic resin-norgel reaction.
  • An inorganic or organic coating or a hybrid coating of both may be formed on the surface of the resin film.
  • the coating include a silica layer formed by a sol-gel method, and an organic layer formed by coating a polymer (for example, an organic material film having a polymerizable group is post-treated by means such as ultraviolet irradiation or heating).
  • Metal oxide, metal nitride forming metal oxide film and metal nitride film examples include metal oxides such as silicon oxide, titanium oxide, and aluminum oxide; metal nitrides such as silicon nitride; and metal oxynitrides such as silicon oxynitride and titanium oxynitride.
  • the water vapor permeability of the resin film having an inorganic or organic film or a hybrid film of both formed on the surface is preferably a high noria film of 0.01 gZm 2 'dayatm or less. ,.
  • the external extraction efficiency of light emission of the organic EL device of the present invention at room temperature is preferably 1% or more, more preferably 2% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element Z The number of electrons flowing to the organic EL element X 100.
  • a hue improvement filter such as a color filter may be used in combination.
  • a film having a roughened surface (such as an anti-glare film) may be used in combination to reduce light emission unevenness.
  • organic EL elements When used as a display device, there are at least two types of organic EL elements having different emission maximum wavelengths, but a preferred example of manufacturing an organic EL element will be described.
  • a desired electrode material for example, a thin film as a material for an anode is formed on an appropriate substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably lOnm-200 nm.
  • a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably lOnm-200 nm.
  • Examples of the method for forming a thin film of the organic compound thin film include a spin coating method, a casting method, an ink jet method, a vapor deposition method, and a printing method as described above.
  • the vacuum evaporation method or the spin coating method is particularly preferred in terms of, for example, the fact that the formation of a film is difficult. Further, a different film forming method may be applied to each layer.
  • the deposition conditions may vary due to kinds of materials used, generally boat temperature 50- 450 ° C, vacuum degree of 10- 6 Pa- 10- 2 Pa, deposition rate 0 Olnm—50nmZ seconds, substrate temperature It is desirable to select a temperature within a range of 50 ° C to 300 ° C and a film thickness of 0.1 nm to 5 ⁇ m.
  • a thin film that also acts as a material for the cathode is formed thereon by a method such as evaporation or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 5 Onm-200 nm.
  • a desired organic EL device can be obtained by forming and providing a cathode. In the production of this organic EL device, it is preferable to produce from the hole injection layer to the cathode consistently by one evacuation, but it is not tough to take it out and apply a different film forming method. At that time, consideration must be given to performing the work in a dry inert gas atmosphere.
  • a shadow mask is provided only when a light emitting layer is formed, and a film can be formed on one surface by an evaporation method, a casting method, a spin coating method, an inkjet method, a printing method, or the like.
  • the method is not particularly limited, but is preferably an evaporation method, an inkjet method, or a printing method.
  • a pattern Jung using a shadow mask is preferable.
  • the production order can 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 can be manufactured in this order.
  • the display device of the present invention can be used as a display device, a display, and various light emission light sources.
  • full-color display is possible by using three types of organic EL elements emitting blue, red and green light.
  • Examples of the display device and display include a television, a personal computer, a mono device, an AV device, a character broadcast display, and an information display in a car.
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • Luminescent light sources include home lighting, car interior lighting, backlights for watches and LCDs, and billboard advertising Illumination devices such as a light source of a traffic light, a light source of an optical storage medium, a light source of an electrophotographic copier, a light source of an optical communication processor, and a light source of an optical sensor, but are not limited thereto.
  • the organic EL device according to the present invention may be used as an organic EL device having a resonator structure.
  • the intended use of the organic EL device having such a resonator structure includes a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, and the like.
  • the present invention is not limited to these. In addition, it can be used for the above applications by causing laser oscillation.
  • the organic EL device of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device of a type for projecting an image, and a type of a device for directly recognizing a still image or a moving image. It may be used as a display device (display).
  • the driving 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 two or more kinds of the organic EL elements of the present invention having different emission colors.
  • FIG. 1 is a schematic diagram showing an example of a display device configured with an organic EL element.
  • FIG. 2 is a schematic view of a display such as a mobile phone for displaying image information by light emission of an organic EL element.
  • the display 1 also has a display unit A having a plurality of pixels and a control unit B for performing image scanning of the display unit A based on image information.
  • the control unit B is electrically connected to the display unit A, sends a scan signal and an image data signal to each of the plurality of pixels based on image information from the outside, and controls the pixels for each scan line by the scan signal. , Sequentially emit light according to the image data signal, perform image scanning, and display image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A has a wiring portion including a plurality of scanning lines 5 and data lines 6, and a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • the figure shows a case where the light power emitted by the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning lines 5 and the plurality of data lines 6 of 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 are 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 in accordance with the received image data.
  • the pixel 3 By properly arranging pixels in the red, green, and blue light emission regions on the same substrate, full color display is possible.
  • 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.
  • a full-color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 for a plurality of pixels and juxtaposing them on the same substrate.
  • an image data signal is applied to the drain of the switching transistor 11 via the data line 6 in the control section B.
  • a scanning signal is applied to the gate of the switching transistor 11 via the control unit B 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 star 12.
  • the capacitor 13 is charged according to the potential of the image data signal, and the driving of the driving transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 10, and an organic EL element connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Element 10 is supplied with current.
  • 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 element 10 continues to emit light until the light is emitted.
  • 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.
  • the element 10 emits light.
  • Such a light emitting 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-valued image data signal having a plurality of gradation potentials, or a predetermined light emission amount by a binary image data signal. No, it's a talent! /.
  • the potential of the capacitor 13 may be maintained until the next scan signal is applied, or may be discharged immediately before the next scan signal is applied.
  • the present invention is not limited to the active matrix method described above, but may be a passive matrix light emission drive in which an organic EL element emits light in accordance with a data signal only when a scanning signal is scanned.
  • FIG. 4 is a schematic diagram of a display device using a noisy matrix method.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a grid pattern facing each other with the pixel 3 interposed therebetween.
  • the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
  • the manufacturing cost can be reduced because an active element is connected to the pixel 3.
  • 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. Simultaneous emission of multiple luminescent colors by multiple luminescent materials White light emission is obtained by mixing colors. As a combination of a plurality of emission colors, a combination of three emission maximum wavelengths of the three primary colors of blue, green, and blue may be used, or a combination of complementary colors such as blue and yellow, and blue-green and orange may be used. It may contain two emission maximum wavelengths.
  • a combination of a plurality of light-emitting materials for obtaining a plurality of luminescent colors includes a combination of a plurality of materials emitting a plurality of phosphorescent or fluorescent lights, and a combination of a luminescent material emitting a fluorescent or phosphorescent light and a luminescent material.
  • Any combination of a dye material that emits light as excitation light may be used, but in the white organic EL device according to the present invention, it is only necessary to mix and combine a plurality of light emitting dopants!
  • the light emitting layer or the hole transport layer is provided with a mask only at the time of forming the electron transport layer or the like, and may be simply arranged by separately applying the mask.
  • an electrode film can be formed on one surface by a vapor deposition method, a casting method, a spin coating method, an inkjet method, a printing method, or the like, and the productivity is also improved.
  • the element itself emits white light, unlike a white organic EL device in which light-emitting elements of a plurality of colors are arranged in parallel in an array.
  • the light emitting material used for the light emitting layer is not particularly limited.
  • the platinum complex according to the present invention may be adjusted to a wavelength range corresponding to CF (color filter) characteristics. Also, whitening may be performed by selecting and combining arbitrary ones from known light emitting materials.
  • the white light-emitting organic EL element of the present invention can be used as a kind of lamp such as home lighting, vehicle interior lighting, and exposure light as various light-emitting light sources and lighting devices, as well as the display device and display. It is also useful for display devices such as backlights of liquid crystal display devices.
  • a backlight such as a clock, a signboard advertisement, a traffic light, a light source such as an optical storage medium, a light source of an electronic photocopier, a light source of an optical communication processor, a light source of an optical sensor, and a display device are required.
  • a wide range of applications such as general household electric appliances.
  • Substrate with 150 nm ITO deposited on glass as anode (NH-Techno Glass: NA-45) After the patterning, the transparent support substrate provided with the ITO transparent electrode was ultrasonically washed with isopropyl alcohol, dried with dry nitrogen gas, and washed with UV ozone for 5 minutes.
  • the transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while five tantalum-made resistance boats were coated with ⁇ -NPD, CBP, Ir-12, BCP, and Alq, respectively. Entering
  • lithium fluoride was placed in a resistance heating boat made of tantalum, and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
  • the heating boat containing the BCP was energized and heated to provide a hole blocking layer having a thickness of lOnm at a deposition rate of 0.1-0.2n mZ seconds.
  • the heating boat containing Alq was energized and heated to provide a hole blocking layer having a thickness of lOnm at a deposition rate of 0.1-0.2n mZ seconds.
  • the heating boat containing Alq was energized and heated to provide a hole blocking layer having a thickness of lOnm at a deposition rate of 0.1-0.2n mZ seconds.
  • Alq Alq
  • An electron transport layer having a thickness of 40 nm was provided at a deposition rate of 0.1-0.2 nmZ seconds by applying a current and heating.
  • barium oxide 105 which is a water trapping agent, is made of a high purity barium oxide powder manufactured by Aldrich Co., Ltd. by using a fluororesin semi-permeable membrane with adhesive (Microtex S-NTF80 31Q manufactured by Nitto Denko). What was pasted on the sealing can 104 was prepared and used in advance. The sealing can was bonded to the organic EL element using an ultraviolet curable adhesive 107, and irradiated with an ultraviolet lamp to bond the two together to produce a sealing element.
  • an ultraviolet curable adhesive 107 is an ultraviolet curable adhesive
  • reference numeral 101 denotes a glass substrate provided with a transparent electrode
  • 102 denotes an organic EL layer composed of a hole injection Z transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and the like
  • 103 denotes a cathode.
  • An organic EL element OLED1-2-141 was produced in the same manner as in the production of the organic EL element OLED1-1 except that the emission dopant was changed as shown in Table 1. (How to make 0LED1-42, 43)
  • OLED1-1 In the fabrication of OLED1-1, the emission host was changed from CBP to AZ1, and the emission dopant was changed.
  • Organic EL devices 1-42 and 43 were produced in the same manner as in OLED1-1, except that the metal complex of the present invention (indicated by compound No. in the table) was used.
  • OLED1-1 was prepared in the same manner as OLED1-1, except that the light-emitting host was changed from CBP to CDBP and the light-emitting dopant was the metal complex of the present invention (indicated by compound No. in the table). EL devices 1-44 to 47 were produced.
  • the obtained organic EL device OLED1-1-147 was evaluated as follows.
  • the organic EL element OLED1- 1- 1 47 room temperature (about 23- 25 ° C), 2. the 5MAZcm 2 constant-performs lighting by conditions, measuring the lighting start immediately after the emission luminance (L) [cdZm 2] As a result, the external extraction quantum efficiency (r?) was calculated.
  • the emission luminance was measured using the CS-10 00 (manufactured by Minolta) was used.
  • the external extraction quantum efficiency was a relative value when the organic EL element OLED1-1 was set to 100.
  • the organic EL element OLED1-1- 1 47, 2. performs continuous lighting by constant current conditions 5mAZcm 2, the time required to becomes half of the initial luminance (tau
  • the light emission lifetime was represented by a relative value when the organic EL element OLED1-1 was set to 100.
  • the CIE chromaticity was measured using CS-1000 (manufactured by Minolta). ⁇ was determined according to the following equation.
  • the external extraction quantum efficiency was a relative value when the organic EL element OLED1-1 was set to 100.
  • OLED1 45 _30 125 164 0,23 The present invention
  • the organic EL element of the present invention has a higher luminous efficiency and a longer luminous life than the comparative organic EL element.
  • the emission colors of the organic EL devices of the present invention were all green.
  • the organic EL element OLED 1-11 of Example 1 was used as a blue light emitting element. [0213] (Production of green light-emitting element)
  • the organic EL element OLED2-7 of Example 2 was used as a green light emitting element.
  • the red, green, and blue light-emitting organic EL elements were juxtaposed on the same substrate to produce an active matrix full-color display device having the form as shown in FIG. 1, and FIG. Only a schematic diagram of the display unit A of the display device is shown. That is, on the same substrate, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, etc.)
  • the scanning line 5 and the plurality of data lines 6 of the wiring portion are made of conductive material, respectively, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid and connected to the pixel 3 at orthogonal positions.
  • the plurality of pixels 3 are driven by an active matrix method including 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.
  • an active matrix method including 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.
  • a full-color display device was manufactured by appropriately arranging the red, green, and blue pixels.
  • the electrode of the transparent electrode substrate of Example 1 was patterned into 20 mm ⁇ 20 mm, and ⁇ -NPD was formed thereon as a hole injection / transport layer with a thickness of 25 nm as in Example 1, and further,
  • the heated boat containing CBP, the boat containing compound P-9 of the present invention, and the boat containing Ir 9 are energized independently of each other, and CBP, which is a luminescent host, and compound P-9, which is a luminescent dopant, and
  • the deposition rate of Ir 9 was adjusted so as to be 100: 5: 0.6, and the deposition was performed so as to have a thickness of 30 nm to provide a light emitting layer.
  • BCP was formed by lOnm to form a hole blocking layer.
  • Alq is deposited at 40nm
  • An electron transport layer was provided.
  • Example 2 a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron transport layer, and 0.5 nm of lithium fluoride and a cathode were formed as a cathode buffer layer.
  • a cathode buffer layer was formed by vapor deposition of aluminum with a thickness of 150 nm.
  • FIG. 6 shows a schematic diagram of a flat lamp.
  • Fig. 6 (a) shows a schematic plan view and Fig. 6 (b) shows a schematic cross-sectional view.
  • an organic EL element a lighting device, and a display device in which the emission wavelength is controlled, which exhibits high emission efficiency, and which has a long emission life.

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Abstract

Est diffusé un matériau de dispositif électroluminescent organique, caractérisé par le fait qu'il contient un complexe métallique ayant une structure partielle représentée par la formule générale (1) ou la formule générale (3) présentée dans la description. Est également présenté un dispositif électroluminescent organique, caractérisé par le fait qu'il contient ce matériau de dispositif électroluminescent organique et qu'il a une grande efficacité lumineuse et une grande durée de vie d'émission, dans lequel l'on contrôle la longueur d'onde d'émission. Sont également présentés un écran et un dispositif d'éclairage, utilisant chacun ce dispositif électroluminescent organique.
PCT/JP2005/004683 2004-03-31 2005-03-16 Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, écran et dispositif d'éclairage WO2005097943A1 (fr)

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EP1640365A1 (fr) * 2003-07-02 2006-03-29 Idemitsu Kosan Co., Ltd. Compose de complexe metallique et dispositif electroluminescent organique renfermant celui-ci
DE102007046445A1 (de) 2007-09-28 2009-04-16 Osram Opto Semiconductors Gmbh Organisches selbstemittierendes Bauteil
DE102008033929A1 (de) 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement
US20100270540A1 (en) * 2007-12-06 2010-10-28 Inktec Co., Ltd. Iridium Complex Containing Carbazole-Substituted Pyridine and Phenyl Derivatives as Main Ligand and Organic Light-Emitting Diodes Containing the Same
DE102009031683A1 (de) 2009-07-03 2011-03-24 Siemens Aktiengesellschaft Phophoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement
DE102010005634A1 (de) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Neuartige Verwendung des Guanidinium-Kations und lichtemittierendes Bauelement
DE102010005632A1 (de) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung und lichtemittierendes Bauelement
JP2012502046A (ja) * 2008-09-03 2012-01-26 ユニバーサル ディスプレイ コーポレイション リン光性材料
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