JP4934035B2 - 有機金属化合物およびかかる化合物で形成された素子 - Google Patents
有機金属化合物およびかかる化合物で形成された素子 Download PDFInfo
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- JP4934035B2 JP4934035B2 JP2007527757A JP2007527757A JP4934035B2 JP 4934035 B2 JP4934035 B2 JP 4934035B2 JP 2007527757 A JP2007527757 A JP 2007527757A JP 2007527757 A JP2007527757 A JP 2007527757A JP 4934035 B2 JP4934035 B2 JP 4934035B2
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- 150000001875 compounds Chemical class 0.000 title claims description 91
- 150000002902 organometallic compounds Chemical class 0.000 title description 28
- 239000000203 mixture Substances 0.000 claims description 39
- -1 polyphenylene Polymers 0.000 claims description 21
- 229920000547 conjugated polymer Polymers 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 5
- 229920000767 polyaniline Polymers 0.000 claims description 5
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 4
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 229920000412 polyarylene Polymers 0.000 claims description 3
- 229920002098 polyfluorene Polymers 0.000 claims description 3
- 229920000123 polythiophene Polymers 0.000 claims description 3
- 150000003513 tertiary aromatic amines Chemical class 0.000 claims description 3
- 239000003446 ligand Substances 0.000 description 108
- 239000010410 layer Substances 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000463 material Substances 0.000 description 56
- 238000000034 method Methods 0.000 description 35
- 229910052751 metal Inorganic materials 0.000 description 33
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- 239000000243 solution Substances 0.000 description 26
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- 125000000217 alkyl group Chemical group 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 230000005525 hole transport Effects 0.000 description 12
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 11
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
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- WOAORAPRPVIATR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1 WOAORAPRPVIATR-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
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- 239000012043 crude product Substances 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
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- 125000004104 aryloxy group Chemical group 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000004404 heteroalkyl group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- 238000010791 quenching Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
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- 125000004428 fluoroalkoxy group Chemical group 0.000 description 4
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- 150000002504 iridium compounds Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 3
- LOZUOAXDIFHKSF-UHFFFAOYSA-N 5-ethylnonane-2,4-dione Chemical compound CCCCC(CC)C(=O)CC(C)=O LOZUOAXDIFHKSF-UHFFFAOYSA-N 0.000 description 3
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
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- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
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- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
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- 239000002243 precursor Substances 0.000 description 3
- 229960001860 salicylate Drugs 0.000 description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- NVLYBJDGUWDDGH-UHFFFAOYSA-N undecane-4,6-dione Chemical compound CCCCCC(=O)CC(=O)CCC NVLYBJDGUWDDGH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 239000011800 void material Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- 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
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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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
- 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
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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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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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
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
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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
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
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US54559604P | 2004-06-09 | 2004-06-09 | |
US60/545,596 | 2004-06-09 | ||
PCT/US2005/020412 WO2005124889A1 (en) | 2004-06-09 | 2005-06-08 | Organometallic compounds and devices made with such compounds |
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JP2012009928A Division JP2012107030A (ja) | 2004-06-09 | 2012-01-20 | 有機金属化合物およびかかる化合物で形成された素子 |
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JP2008504371A JP2008504371A (ja) | 2008-02-14 |
JP2008504371A5 JP2008504371A5 (de) | 2008-07-31 |
JP4934035B2 true JP4934035B2 (ja) | 2012-05-16 |
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JP2007527757A Expired - Fee Related JP4934035B2 (ja) | 2004-06-09 | 2005-06-08 | 有機金属化合物およびかかる化合物で形成された素子 |
JP2012009928A Pending JP2012107030A (ja) | 2004-06-09 | 2012-01-20 | 有機金属化合物およびかかる化合物で形成された素子 |
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EP (1) | EP1754267A1 (de) |
JP (2) | JP4934035B2 (de) |
KR (2) | KR101292376B1 (de) |
WO (2) | WO2005124889A1 (de) |
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US7709100B2 (en) | 2004-07-07 | 2010-05-04 | Universal Display Corporation | Electroluminescent efficiency |
DE112006000604T5 (de) | 2005-03-15 | 2008-01-24 | Isis Innovation Ltd. | Hochverzweigte Dendrimere |
US8218615B2 (en) | 2005-03-29 | 2012-07-10 | Qualcomm Incorporated | Method and apparatus for block-wise decision-feedback equalization for wireless communication |
JP4801928B2 (ja) * | 2005-04-25 | 2011-10-26 | 富士フイルム株式会社 | 有機電界発光素子 |
US7851072B2 (en) | 2005-05-19 | 2010-12-14 | Universal Display Corporation | Stable and efficient electroluminescent materials |
GB0600249D0 (en) | 2006-01-06 | 2006-02-15 | Isis Innovation | Branched compounds and their use in sensors |
JP5145652B2 (ja) * | 2006-05-12 | 2013-02-20 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子用組成物および有機電界発光素子 |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8519130B2 (en) | 2006-12-08 | 2013-08-27 | Universal Display Corporation | Method for synthesis of iriduim (III) complexes with sterically demanding ligands |
KR101634508B1 (ko) * | 2007-03-08 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
CN105153235B (zh) * | 2007-03-08 | 2019-05-10 | 通用显示公司 | 磷光材料 |
US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
JP5484690B2 (ja) | 2007-05-18 | 2014-05-07 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
US20090066234A1 (en) * | 2007-07-05 | 2009-03-12 | Hyun Sik Chae | Light emitting devices and compositions |
JP5481385B2 (ja) * | 2007-11-15 | 2014-04-23 | 日東電工株式会社 | 発光素子および発光組成物 |
GB0814971D0 (en) * | 2008-08-15 | 2008-09-24 | Cambridge Display Tech Ltd | Opto-electrical devices and methods of manufacturing the same |
TWI482756B (zh) * | 2008-09-16 | 2015-05-01 | Universal Display Corp | 磷光物質 |
JP2012505298A (ja) | 2008-10-13 | 2012-03-01 | 日東電工株式会社 | 印刷可能な発光組成物 |
DE102010046412B4 (de) | 2010-09-23 | 2022-01-13 | Merck Patent Gmbh | Metall-Ligand Koordinationsverbindungen |
US20130331577A1 (en) * | 2010-12-23 | 2013-12-12 | Solvay Sa | Preparation of a fac-isomer for a tris homoleptic metal complex |
US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
TW201326361A (zh) | 2011-09-28 | 2013-07-01 | Solvay | 發光材料 |
KR102613306B1 (ko) | 2011-09-30 | 2023-12-14 | 유디씨 아일랜드 리미티드 | 유기 전계 발광 소자, 및 신규 이리듐 착물 |
CN103483387A (zh) * | 2012-06-15 | 2014-01-01 | 李晓常 | 稳定易制的有机光电材料及应用 |
US10199581B2 (en) * | 2013-07-01 | 2019-02-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2014012672A (ja) * | 2013-07-24 | 2014-01-23 | Mitsubishi Chemicals Corp | 有機金属錯体組成物、有機金属錯体含有組成物、有機電界発光素子、有機elディスプレイおよび有機el照明 |
US10003033B2 (en) | 2014-02-18 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9312503B2 (en) | 2014-05-13 | 2016-04-12 | Shenzhen China Star Optoelectronics Technology Co., Ltd | Green light iridium (III) complex and a method of preparing the same |
KR101888934B1 (ko) | 2015-04-24 | 2018-08-16 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시장치 |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10835895B2 (en) * | 2016-04-01 | 2020-11-17 | The University Of Tokyo | Compound and synthesis method therefor |
EP3719028B1 (de) * | 2017-11-29 | 2024-06-12 | Mitsubishi Chemical Corporation | Iridiumkomplexverbindung, diese verbindung und lösungsmittel enthaltende zusammensetzung, organisches elektrolumineszenzelement mit dieser verbindung, anzeigevorrichtung und beleuchtungsvorrichtung |
KR20190115422A (ko) | 2018-04-02 | 2019-10-11 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
US11459348B2 (en) * | 2018-04-02 | 2022-10-04 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
CN117362353A (zh) * | 2018-09-20 | 2024-01-09 | 北京夏禾科技有限公司 | 含有新型辅助配体的有机发光材料 |
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US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP4067286B2 (ja) * | 2000-09-21 | 2008-03-26 | 富士フイルム株式会社 | 発光素子及びイリジウム錯体 |
EP1348711B1 (de) * | 2000-11-30 | 2018-06-13 | Canon Kabushiki Kaisha | Lumineszentes element und display |
US7592074B2 (en) * | 2001-02-20 | 2009-09-22 | Isis Innovation Limited | Metal-containing dendrimers |
JP4438042B2 (ja) * | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
EP1491074B1 (de) * | 2002-03-18 | 2017-07-26 | Oxford University Innovation Limited | Phosphoreszierende dendrimere zur verwendung in lichtemittierenden vorrichtungen |
TWI277617B (en) * | 2002-03-26 | 2007-04-01 | Sumitomo Chemical Co | Metal complexes and organic electro luminescence elements |
JP2003321546A (ja) * | 2002-04-26 | 2003-11-14 | Nippon Hoso Kyokai <Nhk> | 燐光発光性高分子化合物ならびにこれを用いた発光材料および有機el素子 |
AU2003231528A1 (en) * | 2002-04-26 | 2003-11-10 | Nippon Hoso Kyokai | Phosphorescent polymer compound, light emitting material and organic electroluminescent (el) device using the compound |
AU2003263929A1 (en) * | 2002-08-16 | 2004-03-03 | The University Of Southern California | Organic light emitting materials and devices |
DE10238903A1 (de) * | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
GB0219987D0 (en) * | 2002-08-28 | 2002-10-09 | Isis Innovation | Intramolecular interactions in organometallics |
GB0220080D0 (en) * | 2002-08-29 | 2002-10-09 | Isis Innovation | Blended dendrimers |
US20040086743A1 (en) * | 2002-11-06 | 2004-05-06 | Brown Cory S. | Organometallic compounds for use in electroluminescent devices |
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2005
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- 2005-06-08 EP EP05759481A patent/EP1754267A1/de not_active Withdrawn
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2012
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KR20070033350A (ko) | 2007-03-26 |
WO2005124889A1 (en) | 2005-12-29 |
WO2005124890A1 (en) | 2005-12-29 |
JP2008504371A (ja) | 2008-02-14 |
JP2012107030A (ja) | 2012-06-07 |
KR20120052425A (ko) | 2012-05-23 |
EP1754267A1 (de) | 2007-02-21 |
KR101233855B1 (ko) | 2013-02-15 |
KR101292376B1 (ko) | 2013-08-01 |
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