WO2010119891A1 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2010119891A1 WO2010119891A1 PCT/JP2010/056672 JP2010056672W WO2010119891A1 WO 2010119891 A1 WO2010119891 A1 WO 2010119891A1 JP 2010056672 W JP2010056672 W JP 2010056672W WO 2010119891 A1 WO2010119891 A1 WO 2010119891A1
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- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- ORQBXQOJMQIAOY-UHFFFAOYSA-N nobelium Chemical compound [No] ORQBXQOJMQIAOY-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical group C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
- C08G2261/598—Chemical stability
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/351—Thickness
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- 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]
- H10K50/14—Carrier transporting layers
-
- 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]
- H10K50/17—Carrier injection 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to an organic electroluminescence element.
- ELD electroluminescence display
- an inorganic electroluminescence element hereinafter also referred to as an inorganic EL element
- an organic electroluminescence element hereinafter also referred to as an organic EL element
- Inorganic EL elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
- an organic EL element 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 (exciton) are obtained.
- the organic EL element has a feature that it is a surface light source. Applications that can effectively utilize this characteristic include illumination light sources and various display backlights. In particular, it is also suitable to be used as a backlight of a liquid crystal full color display whose demand has been increasing in recent years.
- the light emission color is white or a light source exhibiting a so-called light bulb color (hereinafter collectively referred to as white).
- the light emitting layer is formed by stacking three layers of B / G / R or two layers having complementary colors such as B / Y (see, for example, Patent Document 1), multicolor light emission. Pixels, for example, blue, green, and red are painted separately and emitted simultaneously, and mixed to obtain a white color, or a color conversion dye is used to obtain a white color (for example, a blue light emitting material and a color conversion fluorescent dye Combination) This can be achieved by a method of adjusting a plurality of light emitting materials having different emission wavelengths in one element to obtain white color by mixing.
- the method using different colors of light emitting pixels has a problem that the manufacturing process such as mask alignment is complicated and yield is low, and the color conversion method has low light emission efficiency.
- the present invention has been made in view of the above problems, and its object is to solve the problems of the laminated structure and to improve the external extraction quantum efficiency and lifetime in manufacturing an organic EL element using a wet process. Is to provide.
- the object of the present invention can be achieved by the following configuration.
- the substrate has at least an anode, a cathode, and a laminated structure sandwiched between the anode and the cathode, and there are at least four layers formed by a wet process in the laminated structure.
- the hole injection layer contains a conductive polymer
- the hole transport layer is represented by the following general formula (1).
- An organic electroluminescent device comprising a polymer compound having a repeating unit, wherein the polymer compound has a weight average molecular weight of 50,000 to 200,000 in terms of polystyrene.
- Ar 1 and Ar 3 each independently represents an arylene group which may be independently present, and Ar 1 and Ar 3 may be bonded via a linking group.
- Ar 2 and Ar 4 are Each independently represents an optionally substituted aryl group or aromatic heterocyclic group, n1 and n2 each represent an integer of 0 to 2, and n1 and n2 are not 0 at the same time.) 2.
- T1 is the thickness of the hole injection layer
- T2 is the thickness of the hole transport layer.
- the light emitting layer contains a plurality of light emitting materials having different emission colors, and the light emission spectrum of the plurality of light emitting materials has at least two light emission maximums in a wavelength range of 420 to 650 nm and a light emission minimum in a wavelength range of 480 to 510 nm. 3.
- the organic electroluminescence device as described in 1 or 2 above.
- the light emitting material contained in the light emitting layer includes at least one compound having at least one partial structure selected from the following general formulas (3) to (5).
- the organic electroluminescent element of description includes at least one compound having at least one partial structure selected from the following general formulas (3) to (5).
- Ra represents a hydrogen atom, an aliphatic group, an aromatic hydrocarbon group or an aromatic heterocyclic group
- Rb and Rc each represents a hydrogen atom or a substituent
- A1 represents an aromatic hydrocarbon ring or an aromatic group. Represents a residue necessary to form a heterocycle
- M represents Ir or Pt.
- Ra represents a hydrogen atom, an aliphatic group, an aromatic hydrocarbon group or an aromatic heterocyclic group
- Rb, Rc, Rb 1 and Rc 1 each represents a hydrogen atom or a substituent
- a 1 represents an aromatic group.
- M represents Ir or Pt.
- Ra represents a hydrogen atom, an aliphatic group, an aromatic hydrocarbon group or an aromatic heterocyclic group
- Rb and Rc each represents a hydrogen atom or a substituent
- A1 represents an aromatic hydrocarbon ring or an aromatic group. Represents a residue necessary to form a heterocycle
- M represents Ir or Pt.
- an organic electroluminescence device that can be stably manufactured by a wet process, emits light with high efficiency, and has a long lifetime can be provided.
- the inventors of the present invention limited the polymer compound as the hole transporting material of the hole transporting layer to a specific molecular weight range, so that the film forming property for the wet process is improved. As a result, it was found that the external extraction quantum efficiency and lifetime were improved, and the present invention was achieved.
- the weight average molecular weight of the polymer compound is 50,000 to 200,000 in terms of polystyrene. If the molecular weight is less than this range, there is a concern of mixing with other layers during film formation due to high solubility in a solvent. Even if a film can be formed, the light emission efficiency does not increase at a low molecular weight.
- examples of the arylene group which may have a substituent represented by Ar 1 or Ar 3 include phenylene and diphenylene. These groups may have a substituent such as a lower alkyl group or a lower alkoxy group. Ar 1 or Ar 3 may be bonded via a bonding group. What is a linking group?
- a divalent group such as Ar 1 or Ar 3 bonded via a linking group is, for example, that the linking group is —O— or —S—.
- Preferred Ar 1 or Ar 3 is
- Ar 2 or Ar 4 each independently represents an aryl group which may have a substituent, such as phenyl or diphenyl, or a heterocyclic group such as thienyl or furyl. These groups may have a substituent such as an alkyl group or an alkoxy group.
- Ar 2 or Ar 4 is a phenyl group having a phenyl group and an alkyl group or an alkoxy group as a substituent.
- N1 represents an integer of 0 to 2, preferably an integer of 0 to 1.
- n2 represents an integer of 0 to 2, preferably an integer of 0 to 1.
- n1 and n2 are not 0 at the same time.
- substituents that can be substituted in the general formula (1) include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group).
- alkyl groups for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group).
- oxazolyl group benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group, thienyl group, quinolyl group, Benzofuryl group, dibenzofuryl group, benzothienyl group, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom)
- Quinoxalinyl group pyridazini Group, triazinyl group, quinazolinyl group, phthalazinyl group, etc.
- heterocyclic group eg, pyrrolidyl group, imidazolidyl group, morpholyl group, ox
- 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 compound of the present invention is preferably end-capped.
- the end cap is described in detail in Patent Document 4, and the outline is as follows.
- an end-capping agent a compound that stops polymer growth
- an end-capping agent a compound that stops polymer growth
- the end-capping agent adds end groups to the polymer chain that are substantially incapable of undergoing coupling under polymerization conditions (eg, with other polymer precursors and / or other portions of the polymer chain)
- the end groups end-cap the polymer chain and substantially reduce (preferably stop) the possibility of further polymerization by blocking sites where the polymer chain would grow under polymerization conditions if not end-capped.
- the examples described in Patent Document 4 and Patent Document 5 can be cited.
- the effect of the present invention is that the polymer compound having a repeating unit represented by the general formula (1) is substantially composed of 90% by mass or more of the partial structure represented by the general formula (1). It is preferable in expressing.
- polymer compound having a repeating unit represented by the general formula (1) of the present invention include the following, but these do not limit the scope of the present invention.
- the weight average molecular weight of the polymer compound having the repeating unit represented by the general formula (1) is 50,000 to 200,000 in terms of polystyrene, and more preferably 50,000 to 80,000. . If the weight average molecular weight is less than this range, there is a concern of mixing with other layers during film formation due to the high solubility in the solvent. Even if a film can be formed, the light emission efficiency does not increase at a low molecular weight. When the weight average molecular weight is larger than this range, problems arise due to difficulty in synthesis and purification. Since the molecular weight distribution increases and the residual amount of impurities also increases, the light emission efficiency, voltage, and life of the organic EL element deteriorate.
- the weight average molecular weight can be measured by a gel permeation chromatograph (GPC) method using tetrahydrofuran (THF) as a column solvent.
- GPC gel permeation chromatograph
- a measurement sample is dissolved in tetrahydrofuran so as to have a concentration of 1 mg / ml.
- dissolution conditions it is carried out at room temperature for 5 minutes using an ultrasonic disperser.
- a membrane filter having a pore size of 0.2 ⁇ m a 10 ⁇ L sample solution is injected into the GPC. Examples of GPC measurement conditions are shown below.
- HLC-8220 (manufactured by Tosoh) Column: G4000H XL -G3000H XL -G2000H XL -G2000H XL (manufactured by Tosoh Corporation) Column temperature: 40 ° C Solvent: Tetrahydrofuran Flow rate: 0.2 ml / min Detector: Refractive index detector (RI detector) In the measurement of the molecular weight of a sample, the molecular weight distribution of the sample is calculated using a calibration curve measured using monodisperse polystyrene standard particles. Ten polystyrenes were used for calibration curve measurement.
- Synthesis example 1 (Synthesis of Compound 50) Compound 50 was synthesized according to the following scheme.
- the aliphatic group represented by Ra is an alkyl group (for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, isopentyl group, 2-ethyl-hexyl).
- alkyl group for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, isopentyl group, 2-ethyl-hexyl.
- octyl group, undecyl group, dodecyl group, tetradecyl group cycloalkyl group (for example, cyclopentyl group, cyclohexyl group) and the like.
- examples of the aromatic hydrocarbon group represented by Ra include a phenyl group, a tolyl group, an azulenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrycenyl group, a naphthacenyl group, Examples include o-terphenyl group, m-terphenyl group, p-terphenyl group, acenaphthenyl group, coronenyl group, fluorenyl group, perylenyl group and the like.
- examples of the aromatic heterocyclic group represented by Ra include a pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazinyl group, Triazolyl group (for example, 1,2,4-triazol-1-yl group, 1,2,3-triazol-1-yl group, etc.), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group , Flazanyl group, thienyl group, quinolyl group, benzofuryl group, dibenzofuryl group, benzothienyl group, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (which constitutes the carboline ring of the carbolinyl group)
- the substituents represented by Rb, Rc, Rb 1 and Rc 1 are each an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, tert-butyl).
- These rings may further have a substituent represented by each of Rb and Rc.
- examples of the aromatic hydrocarbon ring formed by A1 include a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, Naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, Examples include a picene ring, a pyrene ring, a pyranthrene ring, and an anthraanthrene ring.
- These rings may further have a substituent represented by each of Rb and Rc.
- the aromatic heterocycle represented by A1 includes a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, and an oxadi Azole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline ring, diazacarbazole ring ( A ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom).
- These rings may further have a substituent represented by each of Rb and Rc.
- the structure represented by any one of the general formulas (3) to (5) is a partial structure, and in order to become a light-emitting dopant of a completed structure, it corresponds to the valence of M forming the partial structure.
- a ligand is required.
- halogen for example, fluorine atom, chlorine atom, bromine atom or iodine atom
- aryl group for example, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, biphenyl group, naphthyl group
- alkyl group eg, methyl group, ethyl group, isopropyl group, hydroxyethyl group, methoxymethyl group, trifluoromethyl group, t-butyl group, etc.
- alkyloxy group aryloxy group
- Alkylthio group, arylthio group aromatic heterocyclic group (for example, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazo
- M represents Ir or Pt. Among them, Ir is preferable. Further, a tris body having a completed structure with three partial structures of the general formulas (3) to (5) is preferable.
- a phosphorescent dopant having a partial structure of any one of the general formulas (3) to (5) (also referred to as a phosphorescent dopant or the like) is, for example, Inorg. Chem. 40, 1704 to 1711, and the like.
- the following conventionally known compounds can be used in combination.
- a white light emitting layer may be formed by laminating at least three light emitting layers.
- a non-light emitting intermediate layer may be provided between the light emitting layers.
- the organic EL element of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.
- the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
- the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferable to adjust in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 to 200 nm, and particularly preferably in the range of 10 to 100 nm.
- the light emitting layer of the organic EL device of the present invention contains a light emitting dopant (phosphorescent dopant, fluorescent dopant, etc.) compound and a light emitting host compound.
- the molecular weight of the light emitting material contained in the light emitting layer is preferably 3,000 or less.
- Luminescent dopant compound The luminescent dopant compound will be described.
- a fluorescent dopant compound also referred to as a fluorescent compound
- a phosphorescent dopant compound also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
- the luminescent dopant compound used in the light emitting layer or the light emitting unit of the organic EL device of the present invention is represented by the general formulas (3) to (5).
- the compound is contained as a phosphorescent dopant compound.
- the phosphorescent dopant compound according to the present invention is a compound in which light emission from an excited triplet is observed.
- the phosphorescent dopant compound is a compound that emits phosphorescence at room temperature (25 ° C.), and the phosphorescence quantum yield is Although defined as a compound of 0.01 or more at 25 ° C., a preferred phosphorescence quantum yield is 0.1 or more.
- the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant compound according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. Just do it.
- the phosphorescent dopant compound There are two types of light emission of the phosphorescent dopant compound in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the luminescent host compound, and this energy is phosphorescent. Energy transfer type that obtains light emission from phosphorescent dopant by transferring to dopant, the other is phosphorescent dopant compound becomes carrier trap, recombination of carriers on phosphorescent dopant causes light emission from phosphorescent dopant compound In either case, the excited state energy of the phosphorescent dopant compound is required to be lower than the excited state energy of the host compound.
- the phosphorescent dopant compound can be appropriately selected from the compounds represented by the general formulas (3) to (5).
- the light-emitting host compound has a mass ratio in the layer of 20% or more among the compounds contained in the light-emitting layer, and a phosphorescence quantum yield of phosphorescence emission at room temperature (25 ° C.). It is defined as a compound of less than 0.1.
- the phosphorescence quantum yield is preferably less than 0.01.
- the mass ratio in the layer is preferably 20% or more.
- the light-emitting host that can be used in the present invention is not particularly limited, and compounds conventionally used in organic EL devices can be used.
- a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
- the light-emitting host of the present invention may be used alone or in combination of two or more.
- the light emitting host used in the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (polymerizable light emitting host). Of course, one or more of such compounds may be used.
- the injection layer includes an electron injection layer and a hole injection layer. As described above, the injection layer may exist between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
- An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
- Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
- anode buffer layer hole injection layer
- JP-A-9-45479 JP-A-9-260062, JP-A-8-288069, and the like.
- cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
- Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc.
- the buffer layer (injection layer) is preferably an extremely thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m although it depends on the material. Particularly preferred is 20 to 100 nm.
- ⁇ Blocking layer hole blocking layer, electron blocking layer>
- 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 Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
- the hole blocking layer has a function of an electron transport 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. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
- the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
- the hole blocking layer preferably contains the carbazole derivative, carboline derivative or diazacarbazole derivative mentioned as the host compound.
- the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
- 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
- the light emitting layer contains a plurality of light emitting materials having different emission colors, and the light emission spectrum of the plurality of light emitting materials emits at least two light emission maxima in the wavelength range of 420 to 650 nm and light emission in the wavelength range of 480 to 510 nm. It is preferable to have a minimum.
- the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
- the film thickness of the hole blocking layer and the electron transporting layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.
- the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
- the hole transport layer can be provided as a single layer or a plurality of layers.
- the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
- a polymer compound having a repeating unit represented by the general formula (1) is used, but the following known compounds may be used in combination.
- triazole derivatives for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives,
- stilbene derivatives silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
- the above-mentioned materials can be used as the hole transport material, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds may be used.
- the hole transport layer can be formed by thinning the hole transport material by a known method such as a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
- the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm, and more preferably 10 to 50 nm.
- the hole transport layer may have a single layer structure composed of one or more of the above materials. Further, when the thickness of the hole injection layer is T1 and the thickness of the hole transport layer is T2, the sum of T1 and T2 is preferably 30 nm to 150 nm, and more preferably 50 nm to 80 nm.
- T1 and T2 When the sum of T1 and T2 is constant, if the relationship between T1 and T2 is T1> T2, the injection of holes from the electrode to the light emitting layer is performed more smoothly, the driving voltage is reduced, and the external extraction is performed. It is preferable because quantum efficiency and emission lifetime are increased.
- a hole transport layer having a high p property doped with impurities examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
- the electron transport layer is made of a material 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.
- the electron transport layer can be provided as a single layer or a plurality of layers.
- an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
- any material can be selected and used from among conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives Thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like.
- a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or 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) 3 , tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga or Pb can also be used as the electron transport material.
- 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 distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
- the electron transport layer can be formed by thinning the electron transport material by a known method such as a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
- the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
- the electron transport layer may have a single layer structure composed of one or more of the above materials.
- an electron transport layer having a high n property doped with impurities examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
- an electron transport layer having such a high n property because an element with lower power consumption can be produced. It is also desirable to use fluorinated alcohol to improve the rectification ratio.
- 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, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
- conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
- an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
- these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not required (about 100 ⁇ m or more)
- a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
- wet film-forming methods such as a printing system and a coating system, can also be used.
- the transmittance be greater than 10%
- the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness depends on the material, it is usually in the range of 10 to 1000 nm, preferably in the range of 10 to 200 nm.
- cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
- electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
- a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
- the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
- the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
- a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
- a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
- polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name, manufactured by JSR) or Appel (trade
- the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ⁇ 2)% RH) is preferably 0.01 g / (m 2 ⁇ 24 h) or less, and oxygen measured by a method according to JIS K 7126-1987.
- a high barrier film having a permeability of 10 ⁇ 3 cm 3 / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less is preferable. More preferably, the transmittance is 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less.
- the material for forming the barrier film may be any material that has a function of suppressing the intrusion of elements that cause deterioration of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
- the method for forming the barrier film is not particularly limited.
- the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
- the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
- the external extraction efficiency at room temperature of light emission of the organic EL element of the present invention is preferably 1% or more, more preferably 5% or more.
- the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
- 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.
- ⁇ Sealing> As a sealing means used for this invention, the method of adhere
- the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
- Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
- the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
- a polymer film and a metal film can be preferably used because the element can be thinned.
- the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 cm 3 / (m 2 ⁇ 24 h ⁇ atm) or less, and conforms to JIS K 7129-1992.
- the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured by the above method is preferably 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
- sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
- the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
- hot-melt type polyamide, polyester, and polyolefin can be mentioned.
- a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
- an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
- a desiccant may be dispersed in the adhesive.
- coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
- the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
- the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
- vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
- a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
- an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
- an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
- a vacuum is also possible.
- a hygroscopic compound can also be enclosed inside.
- Examples of the hygroscopic compound include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.), perchloric acids (eg perchloric acid) Barium, magnesium perchlorate, and the like), and anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
- metal oxides eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
- sulfates eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt
- a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
- the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
- the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
- the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because the light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the element, or between the transparent electrode or the light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.
- a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from the substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
- these methods can be used in combination with the organic EL device of the present invention.
- a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
- the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
- the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
- the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
- This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
- Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
- the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much. However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and light extraction efficiency is increased.
- the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
- the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
- the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
- the organic EL device of the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
- a specific direction for example, the device light emitting surface.
- quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
- One side is preferably 10 ⁇ m to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
- the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
- a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
- BEF brightness enhancement film
- the shape of the prism sheet for example, the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
- a light diffusion plate / film may be used in combination with the light collecting sheet.
- a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
- an anode is fabricated by forming a thin film made of a desired electrode material, for example, an anode material on a suitable substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 10 to 200 nm.
- a method for forming each of these layers there are a vapor deposition method and a wet process (spin coating method, casting method, ink jet method, printing method) as described above, but a uniform film is easily obtained and pinholes are hardly generated.
- a wet process is preferable, and film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is particularly preferable.
- liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
- Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO can be used.
- a dispersion method it can disperse
- a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm.
- a desired organic EL element can be obtained.
- a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode.
- An alternating voltage may be applied.
- the alternating current waveform to be applied may be arbitrary.
- the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
- lighting devices home lighting, interior lighting
- clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
- the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
- patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
- patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
- a conventionally known method is used. Can do.
- the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
- the substrate was transferred to a nitrogen atmosphere, a solution of compound 50a (weight average molecular weight 5,000) dissolved in 0.5% in chlorobenzene was formed by spin coating at 1500 rpm for 30 seconds, and then dried at 160 ° C. for 30 minutes. And it was set as the 30-nm-thick hole transport layer.
- compound 50a weight average molecular weight 5,000
- a light emitting layer composition having the following composition was formed by spin coating at 1500 rpm for 30 seconds, and then dried at 120 ° C. for 30 minutes to form a light emitting layer having a thickness of 50 nm.
- the substrate was attached to a vacuum deposition apparatus without being exposed to the atmosphere.
- a molybdenum resistance heating boat containing KF was attached to a vacuum deposition apparatus, and after the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 5 Pa, the boat was energized and heated to KF 0.02 nm / second. To deposit an electron injecting layer having a thickness of 2 nm. Then, 100 nm of aluminum was vapor-deposited, the cathode was formed, and the organic EL element 1 was produced.
- FIG. 1 shows a schematic diagram of a lighting device, in which an organic EL element 101 is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is performed in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere.
- FIG. 2 shows a cross-sectional view of the lighting device.
- 105 denotes a cathode
- 106 denotes an organic EL layer
- 107 denotes a glass substrate with a transparent electrode.
- the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
- the organic EL device was turned on at room temperature (about 23 to 25 ° C.) and under a constant luminance condition of 1000 cd / m 2 , and the external extraction quantum efficiency ( ⁇ ), drive voltage, and emission spectrum immediately after the start of lighting were measured.
- CS-1000 manufactured by Konica Minolta Sensing
- the external extraction quantum efficiency and the driving voltage are expressed as relative values with the organic EL element 2 as 100.
- the organic EL element was continuously lit at room temperature under a constant current condition with a current having an initial luminance of 1000 cd / m 2, and the time ( ⁇ 1/2 ) required to achieve half the initial luminance was measured.
- the light emission lifetime was expressed as a relative value with the organic EL element 2 as 100.
- the rectification ratio was calculated from a forward voltage flowing through the organic EL element at room temperature and a reverse voltage of 500 ⁇ A / cm 2 .
- the evaluation criteria were ⁇ when the rectification ratio was 100 or more and x when the rectification ratio was less than 100.
Abstract
Description
2.前記正孔注入層の膜厚を(T1)、前記正孔輸送層の膜厚を(T2)としたとき、下記式が成り立つことを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
3.前記発光層が発光色の異なる複数の発光材料を含有し、複数の発光材料の発光スペクトルが420~650nmの波長範囲に少なくとも2つの発光極大と、480~510nmの波長範囲に発光極小を有することを特徴とする前記1または2に記載の有機エレクトロルミネッセンス素子。
6.ウェットプロセスで電子輸送層を形成する際に、フッ化アルコールを使用することを特徴とする前記1~5のいずれか1項に記載の有機エレクトロルミネッセンス素子。
本発明の一般式(1)で表される化合物について説明する。
カラム:G4000HXL-G3000HXL-G2000HXL-G2000HXL(東ソー製)
カラム温度:40℃
溶媒:テトラヒドロフラン
流速:0.2ml/min
検出器:屈折率検出器(RI検出器)
試料の分子量測定では、試料の有する分子量分布を単分散のポリスチレン標準粒子を用いて測定した検量線を用いて算出する。検量線測定用のポリスチレンとしては10点用いた。
(化合物50の合成)
下記スキームにより、化合物50を合成した。
本発明に係る一般式(3)~(5)から選ばれる少なくとも1つの部分構造を有する化合物について説明する。
本発明の有機EL素子の構成層について説明する。本発明において、有機EL素子の層構成の好ましい具体例を以下に示すが、本発明はこれらに限定されない。
(i)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(ii)陽極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
本発明の有機EL素子においては、青色発光層の発光極大波長は430~480nmにあるものが好ましく、緑色発光層は発光極大波長が510~550nm、赤色発光層は発光極大波長が600~640nmの範囲にある単色発光層であることが好ましく、これらを用いた表示装置であることが好ましい。また、これらの少なくとも3層の発光層を積層して白色発光層としたものであってもよい。さらに、発光層間には非発光性の中間層を有していてもよい。本発明の有機EL素子としては白色発光層であることが好ましく、これらを用いた照明装置であることが好ましい。
本発明に係る発光層は、電極または電子輸送層、正孔輸送層から注入されてくる電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であっても発光層と隣接層との界面であってもよい。
発光性ドーパント化合物について説明する。
本発明に係るリン光ドーパント化合物について説明する。
本発明において発光ホスト化合物は、発光層に含有される化合物の内で、その層中での質量比が20%以上であり、かつ室温(25℃)においてリン光発光のリン光量子収率が、0.1未満の化合物と定義される。好ましくはリン光量子収率が0.01未満である。
注入層には、電子注入層と正孔注入層があり、上記の如く陽極と発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在させてもよい。
阻止層は、上記の如く有機化合物薄膜の基本構成層の他に必要に応じて設けられるものである。例えば、特開平11-204258号公報、同11-204359号公報、及び「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の237頁等に記載されている正孔阻止(ホールブロック)層がある。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層または複数層設けることができる。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層または複数層設けることができる。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。さらに膜厚は材料にもよるが、通常は、10~1000nmの範囲であり、好ましくは10~200nmの範囲で選ばれる。
一方、陰極としては仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μm、好ましくは50~200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極または陰極のいずれか一方が透明または半透明であれば発光輝度が向上し好都合である。
本発明の有機EL素子に用いることのできる支持基板(以下、基体、基板、基材、支持体等とも言う)としては、ガラス、プラスチック等の種類には特に限定はなく、また透明であっても不透明であってもよい。支持基板側から光を取り出す場合には、支持基板は透明であることが好ましい。好ましく用いられる透明な支持基板としては、ガラス、石英、透明樹脂フィルムを挙げることができる。特に好ましい支持基板は、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。
本発明に用いられる封止手段としては、例えば、封止部材と電極、支持基板とを接着剤で接着する方法を挙げることができる。
有機層を挟み支持基板と対向する側の前記封止膜、あるいは前記封止用フィルムの外側に、素子の機械的強度を高めるために保護膜、あるいは保護板を設けてもよい。特に封止が前記封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜、保護板を設けることが好ましい。これに使用することができる材料としては、前記封止に用いたのと同様なガラス板、ポリマー板・フィルム、金属板・フィルム等を用いることができるが、軽量かつ薄膜化ということからポリマーフィルムを用いることが好ましい。
有機EL素子は空気よりも屈折率の高い(屈折率が1.7~2.1程度)層の内部で発光し、発光層で発生した光のうち15%から20%程度の光しか取り出せないことが一般的に言われている。これは、臨界角以上の角度θで界面(透明基板と空気との界面)に入射する光は、全反射を起こし素子外部に取り出すことができないことや、透明電極ないし発光層と透明基板との間で光が全反射を起こし、光が透明電極ないし発光層を導波し、結果として光が素子側面方向に逃げるためである。
本発明の有機EL素子は基板の光取り出し側に、例えば、マイクロレンズアレイ状の構造を設けるように加工したり、あるいは所謂集光シートと組み合わせることにより、特定方向、例えば、素子発光面に対し正面方向に集光したりすることにより、特定方向上の輝度を高めることができる。
本発明の有機EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極からなる有機EL素子の作製法を説明する。
本発明の有機EL素子は、表示デバイス、ディスプレイ、各種発光光源として用いることができる。発光光源として、例えば、照明装置(家庭用照明、車内照明)、時計や液晶用バックライト、看板広告、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるがこれに限定するものではないが、特に液晶表示装置のバックライト、照明用光源としての用途に有効に用いることができる。
《有機EL素子1の作製》
陽極としてガラス上にITOを100nm成膜した基板(NHテクノグラス社製:NA-45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso-プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
H-A 22.4質量部
Ir-16 2.5質量部
Ir-1 0.05質量部
Ir-14 0.05質量部
酢酸ブチル 2,000質量部
続いて、30mgのET-Aを4mlのテトラフルオロプロパノール(TFPO)に溶解した溶液を1500rpm、30秒でスピンコート法により製膜した後、120℃で30分間乾燥し、膜厚30nmの電子輸送層とした。
有機EL素子1の作製において、正孔注入層塗布液濃度、正孔輸送層材料(重量平均分子量がそれぞれ異なる50b~50e)、正孔輸送層塗布液濃度、発光層ドーパント、電子輸送層溶媒、正孔注入層膜厚(T1)、正孔輸送層膜厚(T2)を表1に記載のように変更した以外は同様にして、有機EL素子2~10を作製した。
得られた有機EL素子1~10を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて封止し、図1、図2に示すような照明装置を形成して評価した。
有機EL素子を室温(約23~25℃)、1000cd/m2の定輝度条件下による点灯を行い、点灯開始直後の外部取り出し量子効率(η)、駆動電圧、及び発光スペクトルを測定した。ここで、発光輝度の測定はCS-1000(コニカミノルタセンシング製)を用いた。外部取り出し量子効率、駆動電圧は有機EL素子2を100とする相対値で表した。
有機EL素子を室温下、初期輝度1000cd/m2となる電流による定電流条件下で連続点灯を行い、初期輝度の半分の輝度になるのに要する時間(τ1/2)を測定した。発光寿命は有機EL素子2を100とする相対値で表した。
有機EL素子を室温下、500μA/cm2流れる順電圧とその逆電圧による電流値より整流比を算出した。評価基準は整流比が100以上のものを○、100未満のものを×とした。
102 ガラスカバー
105 陰極
106 有機EL層
107 透明電極付きガラス基板
108 窒素ガス
109 捕水剤
Claims (6)
- 基板上に、少なくとも陽極、陰極、及び該陽極、陰極間に挟まれた積層構造を持ち、該積層構造中にウェットプロセスで形成された層が少なくとも4層あり、該ウェットプロセスで形成された層に正孔注入層、正孔輸送層、発光層を少なくとも有する有機エレクトロルミネッセンス素子において、該正孔注入層が導電性高分子を含有し、かつ該正孔輸送層が下記一般式(1)で表される繰り返し単位を有する高分子化合物からなり、かつ該高分子化合物の重量平均分子量が、ポリスチレン換算で50,000~200,000であることを特徴とする有機エレクトロルミネッセンス素子。
- 前記正孔注入層の膜厚を(T1)、前記正孔輸送層の膜厚を(T2)としたとき、下記式が成り立つことを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
式 T1>T2 - 前記発光層が発光色の異なる複数の発光材料を含有し、複数の発光材料の発光スペクトルが420~650nmの波長範囲に少なくとも2つの発光極大と、480~510nmの波長範囲に発光極小を有することを特徴とする請求項1または2に記載の有機エレクトロルミネッセンス素子。
- 前記発光層に含まれる発光材料の分子量が3,000以下であることを特徴とする請求項1~3のいずれか1項に記載の白色発光有機エレクトロルミネッセンス素子。
- 前記発光層に含まれる発光材料として、少なくとも下記一般式(3)~(5)から選ばれる少なくとも1つの部分構造を有する化合物を含有することを特徴とする請求項1~4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
(式中、Raは水素原子、脂肪族基、芳香族炭化水素基または芳香族複素環基を表し、Rb、Rcは各々水素原子または置換基を表し、A1は芳香族炭化水素環または芳香族複素環を形成するのに必要な残基を表し、MはIrまたはPtを表す。)
(式中、Raは水素原子、脂肪族基、芳香族炭化水素基または芳香族複素環基を表し、Rb、Rc、Rb1、Rc1は各々水素原子または置換基を表し、A1は芳香族炭化水素環または芳香族複素環を形成するのに必要な残基を表し、MはIrまたはPtを表す。)
(式中、Raは水素原子、脂肪族基、芳香族炭化水素基または芳香族複素環基を表し、Rb、Rcは各々水素原子または置換基を表し、A1は芳香族炭化水素環または芳香族複素環を形成するのに必要な残基を表し、MはIrまたはPtを表す。) - ウェットプロセスで電子輸送層を形成する際に、フッ化アルコールを使用することを特徴とする請求項1~5のいずれか1項に記載の有機エレクトロルミネッセンス素子。
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