WO2010113761A1 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- WO2010113761A1 WO2010113761A1 PCT/JP2010/055240 JP2010055240W WO2010113761A1 WO 2010113761 A1 WO2010113761 A1 WO 2010113761A1 JP 2010055240 W JP2010055240 W JP 2010055240W WO 2010113761 A1 WO2010113761 A1 WO 2010113761A1
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- Prior art keywords
- layer
- light emitting
- carbon atoms
- organic
- electron
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- 239000010410 layer Substances 0.000 claims abstract description 334
- 239000000463 material Substances 0.000 claims abstract description 87
- 230000005525 hole transport Effects 0.000 claims abstract description 76
- 230000000903 blocking effect Effects 0.000 claims abstract description 52
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 25
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012044 organic layer Substances 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical compound N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 claims description 43
- 238000002347 injection Methods 0.000 claims description 28
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 27
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
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- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
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- 229910052738 indium Inorganic materials 0.000 description 4
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- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 3
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- ZWHOTPNCEFWATE-AWEZNQCLSA-N (3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-AWEZNQCLSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- HLBBYXGGBXZYAU-UHFFFAOYSA-N 1-[2-(2-phenylphenyl)phenyl]-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 HLBBYXGGBXZYAU-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- SSFAUOAQOOISRQ-UHFFFAOYSA-N 2,2-diethoxy-n,n-dimethylethanamine Chemical compound CCOC(CN(C)C)OCC SSFAUOAQOOISRQ-UHFFFAOYSA-N 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical compound C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- APYSVLHTULYCDC-UHFFFAOYSA-N 2-(2-phenylphenyl)benzohydrazide Chemical group NNC(=O)C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 APYSVLHTULYCDC-UHFFFAOYSA-N 0.000 description 1
- VFTRKSBEFQDZKX-UHFFFAOYSA-N 3,3'-diindolylmethane Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4NC=3)=CNC2=C1 VFTRKSBEFQDZKX-UHFFFAOYSA-N 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N O=C(CCCC1)C1=O Chemical compound O=C(CCCC1)C1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ZYEGGTWSVNWDRS-UHFFFAOYSA-N [AlH2]N1CCCC1 Chemical compound [AlH2]N1CCCC1 ZYEGGTWSVNWDRS-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1cc(-[n]2c3ccccc3c3c2cccc3)ccc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1cc(-[n]2c3ccccc3c3c2cccc3)ccc1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- NSNKTSSANPWFJA-UHFFFAOYSA-N c1ccc2[nH]c3c4[nH]c5ccccc5c4ccc3c2c1 Chemical compound c1ccc2[nH]c3c4[nH]c5ccccc5c4ccc3c2c1 NSNKTSSANPWFJA-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
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- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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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]
- H10K50/18—Carrier blocking layers
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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
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- 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
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
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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
- H10K85/321—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
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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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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
Definitions
- the present invention relates to an organic electroluminescent element containing an indolocarbazole compound, and more particularly to a thin film device that emits light by applying an electric field to a light emitting layer made of an organic compound.
- an organic electroluminescence element (hereinafter referred to as an organic EL element) is composed of a pair of counter electrodes with a light emitting layer interposed therebetween as its simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode, holes are injected from the anode, and these are recombined in the light emitting layer to emit light. .
- organic EL elements using organic thin films have been developed.
- the type of electrode is optimized for the purpose of improving the efficiency of carrier injection from the electrode, and a hole transport layer made of aromatic diamine and a light emitting layer made of 8-hydroxyquinoline aluminum complex (Alq3)
- Alq3 8-hydroxyquinoline aluminum complex
- the organic EL element By the way, in the organic EL element, holes and electrons are injected from both electrodes into the light emitting layer in a well-balanced manner, and the injected holes and electrons are efficiently recombined in the light emitting layer. obtain.
- the charge injection into the light emitting layer and the transport balance of both electric charges in the light emitting layer are disrupted, resulting in leakage of charges to the transport layer, reducing the recombination probability in the light emitting layer.
- the recombination region in the light emitting layer is limited to a narrow region near the interface of the transport layer.
- Non-Patent Document 1 proposes to provide an electron and / or exciton blocking layer at the anode side interface of the light emitting layer using the following compound, which is effective in improving efficiency. Is raised.
- Non-Patent Documents 2 and 3 disclose examples in which 1,3-dicarbazolylbenzene (mCP) is used as an electron blocking layer or an exciton blocking layer.
- mCP 1,3-dicarbazolylbenzene
- hole transport of electrons and / or excitons is performed by inserting an organic layer between the hole transport layer and the light emitting layer.
- the organic layer inserted between the hole transport layer and the light-emitting layer is also referred to as an electron blocking layer or an exciton blocking layer because it prevents leakage of electrons and / or excitons to the hole transport layer.
- the electron and / or exciton blocking layer refers to this organic layer.
- the electron and / or exciton blocking layer is also referred to as an EB layer.
- Patent Document 2 and Patent Document 3 disclose the following indolocarbazole compounds.
- an indolocarbazole compound is contained as a charge transporting component, and a hole injection layer or a positive layer is disclosed.
- a hole transport layer it is recommended to use as a material for the hole transport layer, it does not teach the use as a material for the EB layer adjacent to the light emitting layer between the light emitting layer and the hole transport layer.
- An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
- the present invention relates to an organic electroluminescent device in which an organic layer including at least a hole transport layer and a light emitting layer is sandwiched between an anode and a cathode, the phosphorescent material is contained in the light emitting layer, and the hole transport layer
- EB layer electron and / or exciton blocking layer
- the present invention relates to an electroluminescent element.
- Z represents an n-valent aromatic hydrocarbon group having 6 to 50 carbon atoms or an aromatic heterocyclic group having 3 to 50 carbon atoms
- Y represents a group represented by the formula (1a).
- N represents an integer of 1 to 6.
- n is 2 or more, Y may be the same or different.
- ring A represents an aromatic ring represented by formula (1b) that is condensed with an adjacent ring
- ring B represents a heterocyclic ring represented by formula (1c) that is condensed with an adjacent ring.
- R 1 and R 2 each independently represent hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 11 carbon atoms.
- X represents methine or nitrogen
- R 3 represents hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic group having 3 to 11 carbon atoms.
- a heterocyclic group which may be condensed with a ring containing X to form a condensed ring.
- Ar represents an aromatic hydrocarbon group having 6 to 50 carbon atoms or an aromatic heterocyclic group having 3 to 50 carbon atoms.
- indolocarbazole compound represented by the general formula (1) there is an indolocarbazole compound represented by the following general formula (2).
- ring B represents a heterocycle represented by formula (1c) that is condensed with an adjacent ring.
- Z, Ar, R 1 and R 2 are the same as those in the general formula (1).
- R 3 represents hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 11 carbon atoms.
- n represents an integer of 1 or 2.
- indolocarbazole compound represented by the general formula (2) there is an indolocarbazole compound selected from the compounds represented by the general formulas (3) to (6).
- the organic electroluminescent device it is preferable to use a phosphorescent material and an electron transporting host material in combination in the light emitting layer.
- the phosphorescent material and the electron transporting host material may be a single compound or a mixture.
- the organic electroluminescence device further has an electron transport layer, and the electron transfer speed of at least one material used for the electron transport layer is 1 ⁇ 10 ⁇ 7 cm 2 / V ⁇ s or more.
- the LUMO energy of the indolocarbazole compound contained in the EB layer is preferably larger than the LUMO energy of the host material contained in the light emitting layer adjacent to the EB layer.
- the LUMO energy of this indolocarbazole compound is preferably ⁇ 1.2 eV or more.
- the light emitting layer uses a phosphorescent light emitting material and an electron transporting host material in combination, it is derived from the LUMO energy of the electron transporting host material, and when the electron transporting host material is a mixture, the LUMO energy of the main component compound Derived from.
- the HOMO energy of the hole transporting material contained in the hole transporting layer is larger than the HOMO energy of the indolocarbazole compound contained in the EB layer.
- the HOMO energy of the hole transporting material contained in the hole transport layer adjacent to the anode or the hole injection layer is preferably ⁇ 4.8 eV or more.
- Sectional drawing of an example of an organic EL element is shown.
- 1 shows a 1 H-NMR chart of Compound 1-1.
- 1 shows a 1 H-NMR chart of Compound 2-1.
- 1 shows a 1 H-NMR chart of Compound 3-1.
- an organic layer composed of a plurality of layers including at least a hole transport layer and a light emitting layer is sandwiched between an anode and a cathode. And it has EB layer adjacent to the light emitting layer at the side of a positive hole transport layer, and a positive hole transport layer is arrange
- the light emitting layer contains a phosphorescent light emitting material
- the EB layer contains an indolocarbazole compound represented by the general formula (1).
- indolocarbazole compounds represented by the general formula (1) are known in the above-mentioned patent documents and the like, but their use forms are different. However, any indolocarbazole compound known as a hole transporting material can be advantageously used.
- Z represents an n-valent aromatic hydrocarbon group having 6 to 50 carbon atoms and an aromatic heterocyclic group having 3 to 50 carbon atoms, and n Represents an integer of 1 to 6.
- Y represents a group having an indolocarbazole skeleton represented by the formula (1a).
- aromatic hydrocarbon group and aromatic heterocyclic group having no substituent include benzene, pyridine, pyrimidine, triazine, indole, carbazole, naphthalene, quinoline, isoquinoline, quinoxaline, naphthyridine, or these aromatic rings.
- an n-valent group formed by removing n hydrogen atoms from a plurality of linked aromatic compounds and more preferably, benzene, pyridine, pyrimidine, triazine, indole, carbazole, naphthalene, or a combination of these aromatic rings.
- n-valent groups generated by removing hydrogen from the aromatic compound are examples of the aromatic hydrocarbon group and aromatic heterocyclic group having no substituent.
- the number connected is preferably 2 to 10, more preferably 2 to 7.
- the position of connection with Y is not limited, and it may be a terminal ring or a central ring.
- a group generated from an aromatic compound in which a plurality of aromatic rings are connected is represented by the following formula, for example.
- Ar 1 to Ar 6 are unsubstituted monocyclic or condensed aromatic rings
- Specific examples of the group generated by removing hydrogen from the aromatic compound in which a plurality of aromatic rings are connected include biphenyl, terphenyl, bipyridine, bipyrimidine, vitriazine, terpyridine, bistriazylbenzene, dicarbazolylbenzene, carbazolyl.
- substituents include alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 2 carbon atoms, acetyl groups, and 6 to 6 carbon atoms.
- the group which arises from the aromatic compound with which multiple aromatic rings were connected can also have a substituent.
- the total number of substituents is 1 to 10. Preferably it is 1-6, more preferably 1-4. Moreover, when the said aromatic hydrocarbon group or aromatic heterocyclic group has two or more substituents, they may be the same or different. Further, in the calculation of the carbon number of the aromatic hydrocarbon group or aromatic heterocyclic group, when it has a substituent, the carbon number of the substituent is included.
- n is an integer of 1 to 6, preferably 1 to 4, and more preferably 1 to 3.
- Y is represented by formula (1a)
- ring A in formula (1a) is represented by formula (1b).
- X is methine or nitrogen.
- R 3 is hydrogen, an alkyl group hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aromatic heterocyclic group having 3 to 11 carbon atoms, or a six-membered ring containing X Represents a group to be condensed.
- a ring obtained by removing the six-membered ring containing X from a condensed ring formed by condensation includes a pyrrole ring, a furan ring, a thiophene ring, an indole ring, a benzofuran A ring, a benzothiophene ring, a benzene ring, a naphthalene ring, and the like. These rings may have a substituent, and are preferably indole rings which may have a substituent.
- a carbazole ring may be formed.
- R 3 is condensed with a 6-membered ring containing X
- R 3 is a case where the carbon adjacent to the position substituted for the 6-membered ring containing X has a replaceable hydrogen, and becomes a carbazole ring.
- X is methine.
- the ring B is represented by the formula (1c).
- Ar represents an aromatic hydrocarbon group having 6 to 50 carbon atoms and an aromatic heterocyclic group having 3 to 50 carbon atoms. These aromatic hydrocarbon groups and aromatic heterocyclic groups may or may not have a substituent. Preferable examples of these aromatic hydrocarbon groups and aromatic heterocyclic groups are the same as the aromatic hydrocarbon group or aromatic heterocyclic group constituting Z described above except that they are monovalent groups. Moreover, the substitution position of N and Ar in Formula (1c) is not limited.
- aromatic hydrocarbon group and aromatic heterocyclic group having no substituent include monovalent groups generated from benzene, pyridine, pyrimidine, triazine, indole, carbazole, naphthalene, quinoline, isoquinoline, quinoxaline, and naphthyridine. And more preferably, a monovalent group derived from benzene, pyridine, pyrimidine, triazine, indole, carbazole or naphthalene.
- monovalent groups generated from aromatic compounds in which a plurality of these aromatic rings are connected are also preferred, for example, biphenyl, terphenyl, bipyridine, bipyrimidine, vitriazine, terpyridine, bistriazylbenzene, dicarbazolylbenzene, carbazolyl.
- substituents are an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, an acetyl group, or a diarylamino group having 6 to 24 carbon atoms. More preferably, it is a methyl group or a diphenylamino group.
- R 1 and R 2 are each independently hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic group having 3 to 11 carbon atoms. Represents a heterocyclic group.
- Preferred is hydrogen, an alkyl group having 1 to 4 carbon atoms, phenyl group, pyridyl group, pyrimidyl group, triazyl group, naphthyl group, biphenylyl group, bipyrimidyl group or carbazolyl group, and more preferred is hydrogen, phenyl group or carbazolyl group. is there.
- R 1 , R 2 and R 3 are an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 11 carbon atoms. In each case, preferred groups are common.
- an indolocarbazole compound represented by the general formula (2) is preferable.
- ring B represents a heterocycle represented by formula (1c) that is condensed with an adjacent ring.
- the ring B or formula (1c) has the same meaning as the ring B or formula (1c) in the general formula (1).
- Z, Ar, R 1 and R 2 have the same meaning as Z, Ar, R 1 and R 2 in the general formula (1).
- R 3 represents hydrogen, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 11 carbon atoms.
- n represents an integer of 1 or 2.
- an indolocarbazole compound represented by any one of the general formulas (3) to (6) is preferable.
- the indolocarbazole compounds represented by the general formulas (1) to (6) can be synthesized using a known method.
- the indolocarbazole skeleton of the indolocarbazole compound represented by the general formula (3) is Synlett, 2005, No. 1; 1, p42-48 can be synthesized according to the following reaction formula with reference to the synthesis example.
- indolocarbazole skeleton represented by the general formulas (4) and (5) can be obtained from the synthesis examples shown in The Journal of Organic Chemistry, 2007, 72 (15) 5886 and Tetrahedron, 1999, 55, p2371. Can be synthesized according to the following reaction formula. *
- indolocarbazole skeleton represented by the general formula (6) is obtained by the following reaction formula with reference to the synthesis example shown in Archiv der Pharmacie (Weinheim, Germany), 1987, 320 (3), p280-2. Can be synthesized.
- each indolocarbazole obtained in the above reaction formula is subjected to a coupling reaction with a corresponding halogen-substituted aromatic compound, etc., so that hydrogen substituted for two nitrogen atoms present in the indolocarbazole skeleton is replaced with an aromatic group.
- the indolocarbazole compounds of the present invention represented by the general formulas (1) to (6) can be synthesized.
- indolocarbazole compound represented by the general formulas (1) to (6) are shown, but the indolocarbazole compound used in the present invention is not limited to these.
- the organic EL device of the present invention comprises an organic layer including a hole transport layer and a light emitting layer sandwiched between an anode and a cathode, contains a phosphorescent material in the light emitting layer, and includes a hole transport layer and a light emitting layer.
- an EB layer containing an indolocarbazole compound represented by the general formula (1) is provided adjacent to the light emitting layer.
- the indolocarbazole compound represented by the general formula (1) is used as a hole transporting material for a hole transporting layer or a host material for a light emitting layer.
- the EB layer is provided between the hole transport layer and the light emitting layer.
- the material used for the hole transport layer provided separately from the EB layer is a hole transport material having a HOMO energy larger than the HOMO energy of the indolocarbazole compound used for the EB layer. Hole transport materials other than compounds are preferably used.
- One of the adjacent layers of the EB layer is a light emitting layer, and the other is preferably a hole transport layer or a layer containing a hole transport material.
- the layer containing the hole transporting material disposed between the EB layer and the anode also functions as a hole transport layer, this layer is also referred to as a hole transport layer in this specification. Therefore, the hole transport layer may be a single layer or two or more layers.
- the LUMO energy of the indolocarbazole compound contained in the EB layer is preferably larger than the LUMO energy of the compound contained in the adjacent light emitting layer.
- the adjacent light emitting layer contains a plurality of compounds, it is preferably larger than the compound as the main component.
- the LUMO energy of the indolocarbazole compound should be 0.1 eV or more, preferably 0.3 eV or more, and more preferably 0.5 eV or more than the LUMO energy of the compound (main component) contained in the light emitting layer.
- the LUMO energy of the indolocarbazole compound is preferably ⁇ 1.2 eV or more, more preferably ⁇ 1.0 eV or more, and most preferably ⁇ 0.9 eV or more.
- the HOMO energy of the hole transporting material contained in the hole transporting layer is larger than the HOMO energy of the indolocarbazole compound represented by the general formula (1).
- the HOMO energy of the hole transport material adjacent to the anode or the hole injection layer is preferably ⁇ 4.8 eV or more.
- the light emitting layer contains at least one phosphorescent light emitting material and at least one electron transporting host material.
- EBL electrons flowing in the light emitting layer are efficiently blocked by EBL, and leakage of electrons to the hole transport layer is reduced.
- the recombination probability of holes and electrons in the light emitting layer is improved, and the light emission efficiency of the phosphorescent light emitting material is improved.
- an electron transport layer is provided between the cathode and the light emitting layer in addition to the above.
- the preferable electron transfer speed of the material used for the electron transport layer is 1 ⁇ 10 ⁇ 7 cm 2 / V ⁇ s or more, more preferably 1 ⁇ 10 ⁇ 6 cm 2 / V ⁇ s or more, and most preferably 1 ⁇ 10 ⁇ 7 cm 2 / V ⁇ s. ⁇ 10 ⁇ 5 cm 2 / V ⁇ s or more.
- the values of LUMO energy and HOMO energy in this specification are values obtained using Gaussian 03, a molecular orbital calculation software manufactured by Gaussian, USA, and structure optimization calculation at B3LYP / 6-31G * level. It is defined as the value calculated by
- the structure of the organic EL element of the present invention will be described with reference to the drawings.
- the structure of the organic EL element of the present invention is not limited to the illustrated one.
- FIG. 1 is a cross-sectional view schematically showing a structural example of a general organic EL element used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, Represents an EB layer, 6 represents a light emitting layer, 7 represents an electron transport layer, and 8 represents a cathode.
- the organic EL device of the present invention has an anode, a hole transport layer, an EB layer, a light emitting layer, and a cathode as essential layers.
- it has an anode, a hole transport layer, an EB layer, a light emitting layer, an electron transport layer and a cathode.
- the organic EL device of the present invention can also have an electron transport layer, an electron injection layer, and a hole blocking layer in layers other than the essential layers.
- the hole transport layer may be a hole injection / transport layer having a hole injection function
- the electron transport layer may be an electron injection / transport layer having an electron injection function.
- the organic EL device of the present invention has a structure opposite to that shown in FIG. 1, that is, a cathode 8, an electron transport layer 7, a light emitting layer 6, an EB layer 5, a hole transport layer 4 and an anode 2 on the substrate 1 in this order. Stacking is also possible, and in this case, layers can be added or omitted as necessary.
- the organic EL element of the present invention is preferably supported on a substrate.
- the substrate is not particularly limited as long as it is conventionally used for an organic EL element.
- a substrate made of glass, transparent plastic, quartz, or the like can be used.
- 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.
- an electrode substance include conductive transparent materials such as metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
- conductive transparent materials such as metals such as Au, 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 the pattern accuracy is not required (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply
- the 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.
- an electron injecting metal a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy referred to as an electron injecting metal
- an alloy referred to as an electron injecting metal
- 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 anode or the cathode of the organic EL element is transparent or translucent.
- a transparent or semi-transparent cathode can be produced.
- an element in which both the anode and the cathode are transparent is used. Can be produced.
- the light emitting layer is a phosphorescent light emitting layer and includes a phosphorescent light emitting material and a host material.
- a phosphorescent material in the light emitting layer a material containing an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold is preferable.
- organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
- Preferable phosphorescent materials include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 ⁇ acac3, and complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.
- the amount of the phosphorescent light emitting material contained in the light emitting layer is in the range of 1 to 20% by weight, preferably 5 to 10% by weight.
- the host material in the light emitting layer is known from many patent documents and the like, it can be selected from them.
- Specific examples of the host material are not particularly limited, but include indole derivatives, carbazole derivatives, indolocarbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, Pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidine compounds, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyr
- metal complexes represented by tetracarboxylic acid anhydrides, metal complexes of phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, metal complexes of benzoxazole and benzothiazole derivatives, polysilane compounds, poly (N-vinylcarbazole) derivatives, Examples include aniline-based copolymers, thiophene oligomers, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, and polyfluorene derivatives.
- the host material is preferably a compound that prevents the emission of light from becoming longer in wavelength and has a high glass transition temperature. In this specification, the host material is defined as a material that does not emit phosphorescence while the organic EL element is driven.
- the host material has the ability to transport both holes and electrons.
- a material with excellent hole transport performance is a hole transportable host material, and a material with excellent electron transport ability is an electron. Called a transportable host material.
- an electron transporting host material In the organic EL device of the present invention, it is preferable to use an electron transporting host material.
- the electron transporting host material in this specification is defined as a host material having an electron mobility higher than a hole transfer rate or a host material having an electron transfer rate of 1 ⁇ 10 ⁇ 7 cm 2 / V ⁇ s or more.
- the electron transporting host material preferably has an electron moving speed of 1 ⁇ 10 ⁇ 6 cm 2 / V ⁇ s or more.
- Specific electron transporting host materials include carbazole derivatives, indolocarbazole derivatives, pyridine, pyrimidine, triazine, imidazole derivatives, pyrazoles, triazole derivatives, oxazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone.
- Derivatives diphenylquinone derivatives, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine derivatives, 8-quinolinol derivatives
- metal complexes represented by metal complexes, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as a ligand.
- the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission, and includes a hole injection layer and an electron injection layer, And between the cathode and the light emitting layer or the electron transport layer.
- the injection layer can be provided as necessary.
- the blocking layer can block diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer.
- the electron blocking layer can be disposed between the light emitting layer and the hole transport layer and blocks electrons from passing through the light emitting layer toward the hole transport layer.
- a hole blocking layer can be disposed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer toward the electron transporting layer.
- the blocking layer can also be used to block excitons from diffusing outside the light emitting layer. That is, each of the electron blocking layer and the hole blocking layer can also function as an exciton blocking layer.
- the EB layer as used in the present specification is used in the sense of including a layer having a function of an electron blocking layer and / or an exciton blocking layer in one layer.
- the hole blocking layer has a role of blocking holes from reaching the electron transport layer while transporting electrons, thereby improving the recombination probability of electrons and holes in the light emitting layer.
- Examples of the material for the hole blocking layer include aluminum metal complexes, styryl derivatives, triazole derivatives, phenanthroline derivatives, oxadiazole derivatives, and boron derivatives.
- the electron blocking layer has a role to block electrons from reaching the hole transport layer while transporting holes, thereby improving the probability of recombination of electrons and holes in the light emitting layer. .
- an indolocarbazole compound represented by the general formula (1) As the material for the electron blocking layer, it is preferable to use an indolocarbazole compound represented by the general formula (1).
- the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved.
- the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
- the layer when the exciton blocking layer is provided on the anode side, the layer can be inserted adjacent to the light emitting layer between the hole transport layer and the light emitting layer, and when inserted on the cathode side, the light emitting layer and the cathode Between the luminescent layer and the light-emitting layer.
- a hole injection layer, an electron blocking layer, or the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer, and the excitation adjacent to the cathode and the cathode side of the light emitting layer can be provided.
- an electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided between the child blocking layer.
- the EB layer according to the present invention functions as an electron blocking layer and / or an exciton blocking layer, it is advantageous not to provide an electron blocking layer and an exciton blocking layer in addition to the EB layer between the light emitting layer and the anode. It is. In addition, it can provide between a light emitting layer and a cathode as needed.
- the thickness of the EB layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
- an indolocarbazole compound represented by the general formula (1) is preferably used, and the derivative is more preferably used as an exciton blocking layer on the anode side.
- the exciton blocking material may be used.
- exciton blocking layer materials examples include 1,3-dicarbazolylbenzene (mCP) and bis (2-methyl-8-quinolinolato) -4-phenylphenolatoaluminum (III) (BAlq ).
- the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
- the hole transport layer is provided between the EB layer and the anode and contains a hole transport material.
- the hole transport layer is preferably adjacent to the anode or the hole injection layer.
- the hole transport material has a hole transport function and may also serve as an injection function.
- the hole transport material may be either organic or inorganic.
- Examples of known hole transport materials that can be used include triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Examples include 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. It is preferable to use an aromatic tertiary amine compound and a styrylamine compound, and it is more preferable to use an aromatic
- the indolocarbazole compound contained in the EB layer is also a kind of hole transport material, but functions as an EB layer by arranging a layer containing this compound on the light emitting layer side separately from the hole transport layer. .
- An organic EL device using two or more hole transport layers is known, but an example in which an indolocarbazole compound is used in a position such as an EB layer in the organic EL device of the present invention is known. Absent. And providing the said EB layer shows the remarkable effect which is not until now.
- This excellent EB layer has excellent electron blocking effect due to large LUMO energy, moderate HOMO energy and hole transport capability, preventing electrons and excitons from leaking from the light emitting layer, and stable and good device characteristics. Seems to give. Even in a situation where a large number of hole transport materials are known, a compound for the EB layer that gives such good device characteristics is not known, and the present inventors have found it for the first time.
- the indolocarbazole compound is contained in a normal hole transport layer, if the hole transport layer is a single layer, the HOMO energy does not match, the drive voltage becomes higher, or the life tendency tends to be shorter. It becomes.
- the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
- the electron transport material only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
- electron transport layers that can be used include aluminum complexes typified by Alq3, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxalates. And diazole derivatives.
- a thiadiazole derivative in which the 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.
- phosphorus-containing derivatives and silicon-containing attractants have a high electron transfer rate and are preferable electron transport materials.
- 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.
- the EB layer is an electron blocking layer, an exciton blocking layer, or a layer having both functions, and contains an indolocarbazole compound represented by the general formula (1).
- the organic EL element of the present invention may be any one of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix.
- the organic EL device of the present invention by providing an EB layer between the hole transport layer and the phosphorescent light emitting layer adjacent to the light emitting layer, leakage of electrons and / or excitons from the light emitting layer to the hole transport layer is achieved. Therefore, it is possible to obtain an element having higher luminous efficiency than that of a conventional element and having greatly improved driving stability.
- intermediate A 14.1 g (0.061 mol), N, N-dimethylaminoacetaldehyde diethyl acetal 11.4 g (0.071 mol) and 110.0 g acetic acid were stirred at 118 ° C. for 8 hours with heating under reflux. After the reaction solution was cooled to room temperature, the precipitated crystals were collected by filtration and washed with acetic acid (30 ml). The obtained crystals were purified by reslurry to obtain 10.4 g of intermediate B (yield 67%) as white crystals.
- DCZP 2,6-di (4-carbazolylphenyl) pyridine
- TOF Time Of Flight
- DCZP is used as a host material
- Alq3 is used as an electron transport material.
- Alq3 1 ⁇ 10 ⁇ 6 cm 2 / V ⁇ s
- Table 1 shows LUMO energies calculated by structural optimization calculation at B3LYP / 6-31G * level for some compounds using Gaussian 03.
- Table 2 shows the HOMO energies calculated by B3LYP / 6-31G * level structure optimization calculation for several compounds using Gaussian 03.
- Example 1 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed.
- CuPc was formed as a hole injection layer with a thickness of 25 nm on ITO
- NPB was formed as a hole transport layer with a thickness of 30 nm.
- Compound 1-1 was formed as an EB layer to a thickness of 10 nm on the hole transport layer.
- DCZP and Ir (PPy) 3 were co-deposited from different vapor deposition sources as a light emitting layer to form a thickness of 40 nm.
- the concentration of Ir (PPy) 3 was 6.0 wt%.
- Alq3 was formed to a thickness of 20 nm as an electron transport layer.
- lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer.
- Al aluminum as an electrode was formed to a thickness of 170 nm to produce an organic EL element.
- the organic EL element had the light emission characteristics as shown in Table 3.
- Table 1 the luminance, voltage, and luminous efficiency, shown when driving at 2.5 mA / cm 2, also the brightness half time was evaluated at constant current driving of 20 mA / cm 2, the initial this result The value converted in the case of luminance 1000 cd / m 2 is shown.
- the maximum wavelength of the device emission spectrum was 517 nm, and it was found that light emission from Ir (PPy) 3 was obtained.
- Example 2 In Example 1, an organic EL device was produced in the same manner as in Example 1 except that a compound other than Compound 2-1 was used as the EB layer. The maximum wavelength of the device emission spectrum was 517 nm, and it was found that light emission from Ir (PPy) 3 was obtained. The obtained light emission characteristics are shown in Table 1.
- Example 3 In Example 1, an organic EL device was produced in the same manner as in Example 1 except that a compound other than Compound 3-1 was used as the EB layer. The maximum wavelength of the device emission spectrum was 517 nm, and it was found that light emission from Ir (PPy) 3 was obtained. The obtained light emission characteristics are shown in Table 1.
- Example 4 In Example 1, an organic EL device was produced in the same manner as in Example 1 except that compounds other than Compound 1-7 were used as the EB layer.
- Example 5 an organic EL device was produced in the same manner as in Example 1 except that the EB layer other than Compound 2-12 was used.
- Example 6 an organic EL device was prepared in the same manner as in Example 1 except that the compound other than Compound 6-2 was used as the EB layer.
- Example 1 an organic EL device was prepared in the same manner as in Example 1 except that the film thickness of NPB as the hole transport layer was 40 nm and no electron blocking layer was used.
- Example 2 an organic EL device was prepared in the same manner as in Example 1 except that Compound 1-1 was used as the hole transport layer, the film thickness was 40 nm, and no EB layer was used.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that mCP was used as the EB layer.
- the maximum wavelengths of the device emission spectra of the organic EL devices obtained in Examples 1 to 6 and Comparative Examples 1 to 3 were all 517 nm, indicating that light emission from Ir (PPy) 3 was obtained. .
- the emission characteristics are shown in Table 3.
- Example 7 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed.
- CuPc was formed as a hole injection layer on ITO with a thickness of 25 nm
- NPB was formed as a hole transport layer with a thickness of 45 nm.
- Compound 1-1 was formed as an EB layer to a thickness of 10 nm on the hole transport layer.
- DCZP and Ir (piq) 2 acac were co-deposited as a light emitting layer from different evaporation sources to form a thickness of 40 nm.
- the concentration of Ir (piq) 2 acac was 4.5 wt%.
- Alq3 was formed to a thickness of 37.5 nm as an electron transport layer.
- lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer.
- Al (Al) as an electrode was formed to a thickness of 170 nm to produce an organic EL element.
- the organic EL element had light emission characteristics as shown in Table 4.
- Table 4 the luminance, voltage, and luminous efficiency, shown when the current drive of 2.5 mA / cm 2, also the brightness half time was evaluated at constant current driving of 20 mA / cm 2, the initial this result The value converted in the case of luminance 1000 cd / m 2 is shown.
- the maximum wavelength of the device emission spectrum was 620 nm, and it was found that light was emitted from Ir (piq) 2 acac.
- Example 8 an organic EL device was produced in the same manner as in Example 7 except that compounds other than Compound 1-40 were used as the EB layer.
- Example 9 an organic EL device was produced in the same manner as in Example 7 except that compounds other than Compound 2-12 were used as the EB layer.
- Example 10 an organic EL device was produced in the same manner as in Example 7 except that the compound other than Compound 6-2 was used as the EB layer.
- Example 4 an organic EL device was produced in the same manner as in Example 4 except that the film thickness of NPB as the hole transport layer was 55 nm and the EB layer was not used.
- the indolocarbazole compound used in the present invention exhibits good hole transport properties and has a large LUMO energy. Therefore, by providing the EB layer containing this adjacent to the phosphorescent light emitting layer between the hole transporting layer and the phosphorescent light emitting layer, the hole can be effectively transported from the anode to the light emitting layer. It is possible to prevent leakage of electrons and excitons from the light emitting layer to the hole transport layer, and as a result, it is possible to improve the light emitting efficiency of the device and improve the driving life. That is, the EB layer in the present invention functions as an electron blocking layer and / or an exciton blocking layer, and this EB layer greatly improves the initial characteristics and driving life of the organic EL element.
- the indolocarbazole compound is found to have good thin film stability and thermal stability, and the organic EL device having an EB layer containing the compound exhibits excellent driving stability and high durability. It was revealed that.
- the organic EL device of the present invention has practically satisfactory levels of light emission characteristics, drive life and durability, and is a flat panel display (mobile phone display device, in-vehicle display device, OA computer display device, television, etc.), surface light emission. Its technical value is great in applications to light sources (lighting, light sources for copying machines, backlight light sources for liquid crystal displays and instruments), display boards, and sign lamps that make use of the characteristics of the body.
Abstract
Description
式(1a)中、環Aは隣接環と縮合する式(1b)で表される芳香族環を示し、環Bは隣接環と縮合する式(1c)で表される複素環を表す。R1、R2はそれぞれ独立に、水素、炭素数1~10の脂肪族炭化水素基、炭素数6~12の芳香族炭化水素基又は炭素数3~11の芳香族複素環基を示す。
式(1b)中、Xはメチン又は窒素を示し、R3は水素、炭素数1~10の脂肪族炭化水素基、炭素数6~12の芳香族炭化水素基又は炭素数3~11の芳香族複素環基を示すが、Xを含む環と縮合して縮合環を形成しても良い。
式(1c)中、Arは炭素数6~50の芳香族炭化水素基又は炭素数3~50の芳香族複素環基を示す。
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。
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。更に膜厚は材料にもよるが、通常10~1000nm、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素子の陽極又は陰極のいずれか一方が、透明又は半透明である。
発光層は燐光発光層であり、燐光発光材料とホスト材料を含む。発光層における燐光発光材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。かかる有機金属錯体は、前記特許文献等で公知であり、これらが選択されて使用可能である。
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。
阻止層は、発光層中に存在する電荷(電子若しくは正孔)及び/又は励起子の発光層外への拡散を阻止することができる。電子阻止層は、発光層及び正孔輸送層の間に配置されることができ、電子が正孔輸送層の方に向かって発光層を通過することを阻止する。同様に、正孔阻止層は発光層及び電子輸送層の間に配置されることができ、正孔が電子輸送層の方に向かって発光層を通過することを阻止する。阻止層はまた、励起子が発光層の外側に拡散することを阻止するために用いることができる。すなわち電子阻止層、正孔阻止層はそれぞれ励起子阻止層としての機能も兼ね備えることができる。本明細書でいうEB層は、一つの層で電子阻止層及び/又は励起子阻止層の機能を有する層を含む意味で使用される。
正孔阻止層は電子を輸送しつつ、正孔が電子輸送層へ到達することを阻止する役割があり、これにより発光層中での電子と正孔の再結合確率を向上させることができる。正孔阻止層の材料としては、アルミニウム金属錯体、スチリル誘導体、トリアゾール誘導体、フェナントロリン誘導体、オキサジアゾール誘導体、ボロン誘導体等が挙げられる。
電子阻止層は正孔を輸送しつつ、電子が正孔輸送層へ到達することを阻止する役割があり、これにより発光層中での電子と正孔が再結合する確率を向上させることができる。
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、本層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。すなわち、励起子阻止層を陽極側に有する場合、正孔輸送層と発光層の間に、発光層に隣接して該層を挿入することができ、陰極側に挿入する場合、発光層と陰極との間に、発光層に隣接して該層を挿入することができる。また、陽極と、発光層の陽極側に隣接する励起子阻止層との間には、正孔注入層や電子阻止層などを有することができ、陰極と、発光層の陰極側に隣接する励起子阻止層との間には、電子注入層、電子輸送層、正孔阻止層などを有することができる。
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、正孔輸送層は単層又は複数層設けることができる。正孔輸送層はEB層と陽極の間に設けられ、正孔輸送材料を含有する。正孔輸送層は、陽極又は正孔注入層に隣接することが好ましい。
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、電子輸送層は単層又は複数層設けることができる。
EB層は、電子阻止層、励起子阻止層又は両者の機能を有する層であり、一般式(1)で表されるインドロカルバゾール化合物を含有する。
以下に示す数値は、電場E1/2=500(V/cm)1/2の時の値を示す。
DCZP:3×10-6cm2/V・s
Alq3:1×10-6cm2/V・s
膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔注入層としてCuPcを25nmの厚さに形成し、次に孔輸送層としてNPBを30nmの厚さに形成した。次に、正孔輸送層上に、EB層として化合物1-1を10nmの厚さに形成した。次に発光層としてDCZPとIr(PPy)3とを異なる蒸着源から、共蒸着し、40nmの厚さに形成した。この時、Ir(PPy)3の濃度は6.0wt%であった。次に、電子輸送層としてAlq3を20nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
実施例1において、EB層として化合物2-1以外を用いた以外は実施例1と同様にして有機EL素子を作成した。素子発光スペクトルの極大波長は517nmであり、Ir(PPy)3からの発光が得られていることがわかった。得られた発光特性を表1に示す。
実施例1において、EB層として化合物3-1以外を用いた以外は実施例1と同様にして有機EL素子を作成した。素子発光スペクトルの極大波長は517nmであり、Ir(PPy)3からの発光が得られていることがわかった。得られた発光特性を表1に示す。
実施例1において、EB層として化合物1-7以外を用いた以外は実施例1と同様にして有機EL素子を作成した。
実施例1において、EB層として化合物2-12以外を用いた以外は実施例1と同様にして有機EL素子を作成した。
実施例1において、EB層として化合物6-2以外を用いた以外は実施例1と同様にして有機EL素子を作成した。
実施例1において、正孔輸送層としてのNPBの膜厚を40nmとし、電子阻止層を使用しない以外は、実施例1と同様にして有機EL素子を作成した。
実施例1において、正孔輸送層として化合物1-1を用い、その膜厚を40nmとし、EB層を使用しない以外は、実施例1と同様にして有機EL素子を作成した
実施例1において、EB層としてmCPを用いた以外は実施例1と同様にして有機EL素子を作成した。
膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔注入層としてCuPcを25nmの厚さに形成し、次に孔輸送層としてNPBを45nmの厚さに形成した。次に、正孔輸送層上に、EB層として化合物1-1を10nmの厚さに形成した。次に発光層としてDCZPとIr(piq)2acacとを異なる蒸着源から、共蒸着し、40nmの厚さに形成した。この時、Ir(piq)2acacの濃度は4.5wt%であった。次に、電子輸送層としてAlq3を37.5nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
実施例7において、EB層として化合物1-40以外を用いた以外は実施例7と同様にして有機EL素子を作成した。
実施例7において、EB層として化合物2-12以外を用いた以外は実施例7と同様にして有機EL素子を作成した。
実施例7において、EB層として化合物6-2以外を用いた以外は実施例7と同様にして有機EL素子を作成した。
実施例4において、正孔輸送層としてのNPBの膜厚を55nmとし、EB層を使用しない以外は、実施例4と同様にして有機EL素子を作成した。
加えて、該インドロカルバゾール化合物は良好な薄膜安定性と熱安定性を有することを見出し、これを含むEB層を有する有機EL素子が、優れた駆動安定性を示す耐久性の高い有機EL素子であることを明らかにした。
本発明の有機EL素子は、発光特性、駆動寿命ならびに耐久性において、実用上満足できるレベルにあり、フラットパネルディスプレイ(携帯電話表示素子、車載表示素子、OAコンピュータ表示素子やテレビ等)、面発光体としての特徴を生かした光源(照明、複写機の光源、液晶ディスプレイや計器類のバックライト光源)、表示板や標識灯等への応用において、その技術的価値は大きいものである。
Claims (9)
- 陽極と陰極の間に、少なくとも正孔輸送層と発光層を含む有機層を挟持してなる有機電界発光素子において、発光層に燐光発光材料を含有し、正孔輸送層と発光層の間に、発光層と隣接して一般式(1)で表されるインドロカルバゾール化合物を含有する電子及び/又は励起子阻止層を有することを特徴とする有機電界発光素子。
一般式(1)中、Zはn価の炭素数6~50の芳香族炭化水素基又は炭素数3~50の芳香族複素環基を示し、Yは式(1a)で表される基を示し、nは1~6の整数を示す。nが2以上の場合、Yは同一でも異なっていても良い。
式(1a)中、環Aは隣接環と縮合する式(1b)で表される芳香族環を示し、環Bは隣接環と縮合する式(1c)で表される複素環を示す。R1、R2はそれぞれ独立に、水素、炭素数1~10の脂肪族炭化水素基、炭素数6~12の芳香族炭化水素基又は炭素数3~11の芳香族複素環基を示す。
式(1b)中、Xはメチン又は窒素を示し、R3は水素、炭素数1~10の脂肪族炭化水素基、炭素数6~12の芳香族炭化水素基又は炭素数3~11の芳香族複素環基を示すが、Xを含む環と縮合して縮合環を形成しても良い。
式(1c)中、Arは炭素数6~50の芳香族炭化水素基又は炭素数3~50の芳香族複素環基を示す。 - 発光層に、燐光発光材料と、電子輸送性ホスト材料とを含有することを特徴とする請求項1に記載の有機電界発光素子。
- 有機層が更に電子輸送層を有し、該電子輸送層に用いる材料の少なくとも一つの材料の電子移動速度が1×10-7cm2/V・s以上であることを特徴とする請求項1に記載の有機電界発光素子。
- 電子及び/又は励起子阻止層に含有されるインドロカルバゾール化合物のLUMOエネルギーが、発光層に含有されるホスト材料のLUMOエネルギーよりも大きいことを特徴とする請求項1に記載の有機電界発光素子。
- インドロカルバゾール化合物のLUMOエネルギーが、-1.2eV以上であることを特徴とする請求項1に記載の有機電界発光素子。
- 正孔輸送層に含有される正孔輸送性材料のHOMOエネルギーが、電子及び/又は励起子阻止層に含有されるインドロカルバゾール化合物のHOMOエネルギーよりも大きいことを特徴とする請求項1に記載の有機電界発光素子。
- 陽極又は正孔注入層に隣接して正孔輸送層を有し、該正孔輸送層に含有される正孔輸送材料のHOMOエネルギーが、-4.8eV以上であることを特徴とする請求項1に記載の有機電界発光素子。
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JPWO2011080972A1 (ja) * | 2009-12-28 | 2013-05-09 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
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Also Published As
Publication number | Publication date |
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TWI468494B (zh) | 2015-01-11 |
JP5723764B2 (ja) | 2015-05-27 |
KR101759966B1 (ko) | 2017-07-20 |
TW201107447A (en) | 2011-03-01 |
EP2416627A4 (en) | 2014-02-26 |
EP2416627B1 (en) | 2019-01-02 |
US20120007070A1 (en) | 2012-01-12 |
CN102362551A (zh) | 2012-02-22 |
JPWO2010113761A1 (ja) | 2012-10-11 |
CN102362551B (zh) | 2016-03-23 |
US9299947B2 (en) | 2016-03-29 |
EP2416627A1 (en) | 2012-02-08 |
KR20120003922A (ko) | 2012-01-11 |
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