BRPI0009215B1 - complexos metálicos ciclometalizados como dopantes fosforescentes em diodos emissores de luz orgânicos - Google Patents
complexos metálicos ciclometalizados como dopantes fosforescentes em diodos emissores de luz orgânicos Download PDFInfo
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- BRPI0009215B1 BRPI0009215B1 BRPI0009215A BR0009215A BRPI0009215B1 BR PI0009215 B1 BRPI0009215 B1 BR PI0009215B1 BR PI0009215 A BRPI0009215 A BR PI0009215A BR 0009215 A BR0009215 A BR 0009215A BR PI0009215 B1 BRPI0009215 B1 BR PI0009215B1
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- 239000002019 doping agent Substances 0.000 title claims abstract description 21
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 6
- 239000002184 metal Substances 0.000 title claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 38
- 150000003057 platinum Chemical class 0.000 claims abstract description 8
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 66
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 10
- 230000010287 polarization Effects 0.000 claims description 7
- 239000000370 acceptor Substances 0.000 claims description 5
- 238000004020 luminiscence type Methods 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- -1 organometallic platinum complexes Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002800 charge carrier Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 108091006149 Electron carriers Proteins 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- KSHYDMGICWRWSL-UHFFFAOYSA-N 2-thiophen-2-ylquinoline Chemical compound C1=CSC(C=2N=C3C=CC=CC3=CC=2)=C1 KSHYDMGICWRWSL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- DCIVLRIRJUWCIS-UHFFFAOYSA-L ethylsulfanylethane;platinum(2+);dichloride Chemical compound [Cl-].[Cl-].[Pt+2].CCSCC.CCSCC DCIVLRIRJUWCIS-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QAFJHDNFUMKVIE-UHFFFAOYSA-N 2,2'-dinitrobiphenyl Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1[N+]([O-])=O QAFJHDNFUMKVIE-UHFFFAOYSA-N 0.000 description 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 229910003556 H2 SO4 Inorganic materials 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 229910017852 NH2NH2 Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- VJVOPINBJQWMNY-UHFFFAOYSA-N butanedioic acid;ethane-1,2-diol Chemical compound OCCO.OC(=O)CCC(O)=O VJVOPINBJQWMNY-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229930192419 itoside Natural products 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
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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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- 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
- 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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27460999A | 1999-03-23 | 1999-03-23 | |
| PCT/US2000/007574 WO2000057676A1 (en) | 1999-03-23 | 2000-03-22 | Cyclometallated metal complexes as phosphorescent dopants in organic leds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0009215A BR0009215A (pt) | 2002-04-16 |
| BRPI0009215B1 true BRPI0009215B1 (pt) | 2017-05-09 |
Family
ID=23048920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0009215A BRPI0009215B1 (pt) | 1999-03-23 | 2000-03-22 | complexos metálicos ciclometalizados como dopantes fosforescentes em diodos emissores de luz orgânicos |
Country Status (7)
| Country | Link |
|---|---|
| EP (2) | EP1181842B1 (enExample) |
| JP (1) | JP4619546B2 (enExample) |
| KR (2) | KR20100042665A (enExample) |
| CN (1) | CN1226902C (enExample) |
| AU (1) | AU3908400A (enExample) |
| BR (1) | BRPI0009215B1 (enExample) |
| WO (1) | WO2000057676A1 (enExample) |
Families Citing this family (171)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3321954A1 (en) * | 1999-05-13 | 2018-05-16 | The Trustees of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
| JP2001181617A (ja) * | 1999-12-27 | 2001-07-03 | Fuji Photo Film Co Ltd | オルトメタル化白金錯体からなる発光素子材料および発光素子 |
| JP4048521B2 (ja) | 2000-05-02 | 2008-02-20 | 富士フイルム株式会社 | 発光素子 |
| US6946688B2 (en) | 2000-06-30 | 2005-09-20 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US7476452B2 (en) | 2000-06-30 | 2009-01-13 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| 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 |
| US7132681B2 (en) | 2000-06-30 | 2006-11-07 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US7306856B2 (en) | 2000-07-17 | 2007-12-11 | Fujifilm Corporation | Light-emitting element and iridium complex |
| EP1175128B1 (en) | 2000-07-17 | 2010-09-22 | FUJIFILM Corporation | Light emitting element and azole compound |
| 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 |
| JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
| US6893743B2 (en) | 2000-10-04 | 2005-05-17 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
| JP3855675B2 (ja) * | 2000-11-30 | 2006-12-13 | 三菱化学株式会社 | 有機電界発光素子 |
| JP4154145B2 (ja) * | 2000-12-01 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
| SG138466A1 (en) | 2000-12-28 | 2008-01-28 | Semiconductor Energy Lab | Luminescent device |
| JP4994564B2 (ja) * | 2001-03-02 | 2012-08-08 | ザ、トラスティーズ オブ プリンストン ユニバーシティ | 二重ドープ層燐光有機発光装置 |
| CN1267525C (zh) | 2001-03-08 | 2006-08-02 | 香港大学 | 有机金属光发射材料 |
| EP2259285B1 (en) | 2001-05-16 | 2014-10-22 | The Trustees Of Princeton University | High efficiency multi-color electro-phosphorescent OLEDs. |
| JP2002352957A (ja) * | 2001-05-23 | 2002-12-06 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
| US6855438B2 (en) | 2001-06-15 | 2005-02-15 | Konica Corporation | Organic electroluminescent element and full color display |
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| JP5849867B2 (ja) | 2012-06-21 | 2016-02-03 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| KR20240154693A (ko) * | 2012-08-03 | 2024-10-25 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 장치 및 조명 장치 |
| CN104641484B (zh) | 2012-09-21 | 2017-09-08 | 株式会社半导体能源研究所 | 发光元件、发光装置、电子设备及照明装置 |
| WO2014092014A1 (ja) | 2012-12-10 | 2014-06-19 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
| US9944629B2 (en) | 2012-12-10 | 2018-04-17 | Konica Minolta, Inc. | Material for organic electroluminescent element, organic electroluminescent element, illumination device, and display device |
| WO2014204696A1 (en) * | 2013-06-17 | 2014-12-24 | University Of South Florida | Transparent contacts organic solar panel by spray |
| US10593886B2 (en) | 2013-08-25 | 2020-03-17 | Molecular Glasses, Inc. | OLED devices with improved lifetime using non-crystallizable molecular glass mixture hosts |
| CN106164033B (zh) | 2014-01-10 | 2019-04-19 | 国立研究开发法人产业技术综合研究所 | 环金属化铱配合物的原料及制造方法 |
| EP3216066B1 (en) * | 2014-11-05 | 2021-05-26 | Okinawa Institute of Science and Technology School Corporation | Doping engineered hole transport layer for perovskite-based device |
| DE112016006231T5 (de) | 2016-01-14 | 2018-10-18 | National Institute Of Advanced Industrial Science And Technology | Verfahren zum Herstellen eines cyclometallierten Iridiumkomplexes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4885211A (en) * | 1987-02-11 | 1989-12-05 | Eastman Kodak Company | Electroluminescent device with improved cathode |
| US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
| DE69514495T2 (de) | 1994-08-11 | 2000-08-10 | Koninklijke Philips Electronics N.V., Eindhoven | Festkörper-bildverstärker und röntgenuntersuchungsgerät mit einem festkörper-bildverstärker |
| US5703436A (en) * | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| US6048630A (en) * | 1996-07-02 | 2000-04-11 | The Trustees Of Princeton University | Red-emitting organic light emitting devices (OLED's) |
| US6097147A (en) * | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
| JP4154140B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
| US9515790B2 (en) | 2012-02-29 | 2016-12-06 | Lg Electronics Inc. | Method for reducing inter-cell interference in cooperative multi-cell wireless communication system, and apparatus for same |
| CN103376058A (zh) | 2012-04-28 | 2013-10-30 | 鸿富锦精密工业（深圳）有限公司 | 温度补偿系统及方法 |
-
2000
- 2000-03-22 KR KR1020107007163A patent/KR20100042665A/ko not_active Ceased
- 2000-03-22 EP EP00918238.7A patent/EP1181842B1/en not_active Revoked
- 2000-03-22 KR KR1020017012164A patent/KR101166264B1/ko not_active Expired - Lifetime
- 2000-03-22 JP JP2000607445A patent/JP4619546B2/ja not_active Expired - Lifetime
- 2000-03-22 EP EP16171124.7A patent/EP3076759A1/en not_active Withdrawn
- 2000-03-22 AU AU39084/00A patent/AU3908400A/en not_active Abandoned
- 2000-03-22 BR BRPI0009215A patent/BRPI0009215B1/pt active IP Right Grant
- 2000-03-22 WO PCT/US2000/007574 patent/WO2000057676A1/en not_active Ceased
- 2000-03-22 CN CNB008073279A patent/CN1226902C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR0009215A (pt) | 2002-04-16 |
| EP1181842A1 (en) | 2002-02-27 |
| EP1181842A4 (en) | 2005-04-06 |
| EP3076759A1 (en) | 2016-10-05 |
| CN1226902C (zh) | 2005-11-09 |
| CN1350768A (zh) | 2002-05-22 |
| KR20020004982A (ko) | 2002-01-16 |
| KR20100042665A (ko) | 2010-04-26 |
| KR101166264B1 (ko) | 2012-07-17 |
| JP2002540572A (ja) | 2002-11-26 |
| AU3908400A (en) | 2000-10-09 |
| WO2000057676A1 (en) | 2000-09-28 |
| JP4619546B2 (ja) | 2011-01-26 |
| EP1181842B1 (en) | 2016-05-25 |
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