CN1610467A - 双核有机金属配合物和使用其的有机电致发光器件 - Google Patents
双核有机金属配合物和使用其的有机电致发光器件 Download PDFInfo
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- CN1610467A CN1610467A CNA200410068766XA CN200410068766A CN1610467A CN 1610467 A CN1610467 A CN 1610467A CN A200410068766X A CNA200410068766X A CN A200410068766XA CN 200410068766 A CN200410068766 A CN 200410068766A CN 1610467 A CN1610467 A CN 1610467A
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- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 37
- 238000005401 electroluminescence Methods 0.000 title abstract description 5
- 239000012044 organic layer Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 15
- -1 hydroxy, mercapto Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 claims description 3
- DONUJQOZMIKGPR-UHFFFAOYSA-N (carbamoylamino) dihydrogen phosphate Chemical compound NC(=O)NOP(O)(O)=O DONUJQOZMIKGPR-UHFFFAOYSA-N 0.000 claims description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims 1
- 125000006740 (C6-C20) heteroaryloxy group Chemical group 0.000 claims 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims 1
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- 239000010410 layer Substances 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 238000010894 electron beam technology Methods 0.000 description 1
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- 230000005281 excited state Effects 0.000 description 1
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- 239000007888 film coating Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000327 poly(triphenylamine) polymer Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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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
-
- 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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- 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
- 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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- 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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- 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
- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
式 | HOMO(eV) | 最大(nm)溶液中 | 最大(nm)膜中 | LUMO(eV) | CIE(x,y) | 分解温度 |
2 | 6.20 | 462 | 463 | 2.85 | (0.15,0.26) | 300 |
3 | 6.32 | 450,477 | 450,477 | 3.57 | (0.14,0.18) | 266 |
4 | 6.26 | 461,488 | 462 | 2.91 | (0.14,0.22) | 250 |
5 | 6.40 | 460 | 460 | 2.96 | (0.14,0.22) | 290 |
6 | 6.15 | 460 | 461 | 3.46 | (0.14,0.21) | 315 |
7 | 6.11 | 460 | 461 | 3.42 | (0.14,0.20) | 310 |
8 | 6.12 | 468 | 467 | 2.86 | (0.14,0.26) | 305 |
9 | - | 462 | 461 | - | (0.16,0.28) | 280 |
10 | - | 494 | 498 | - | (0.19,0.51) | 295 |
11 | - | 480 | 482 | - | (0.15,0.27) | 290 |
Claims (14)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR62371/03 | 2003-09-06 | ||
KR1020030062371A KR100718100B1 (ko) | 2003-09-06 | 2003-09-06 | 이핵 유기금속 착물 및 이를 이용한 유기 전계 발광 소자 |
KR62371/2003 | 2003-09-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1610467A true CN1610467A (zh) | 2005-04-27 |
CN100456525C CN100456525C (zh) | 2009-01-28 |
Family
ID=34374126
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB200410068766XA Expired - Lifetime CN100456525C (zh) | 2003-09-06 | 2004-09-06 | 双核有机金属配合物和使用其的有机电致发光器件 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7306857B2 (zh) |
EP (1) | EP1538153A1 (zh) |
JP (1) | JP4713864B2 (zh) |
KR (1) | KR100718100B1 (zh) |
CN (1) | CN100456525C (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102317405A (zh) * | 2008-07-16 | 2012-01-11 | 索尔维公司 | 包括多核络合物的发光材料 |
CN101016317B (zh) * | 2006-02-11 | 2013-02-20 | 三星显示有限公司 | 环金属化过渡金属络合物及使用其的有机电致发光器件 |
CN102076817B (zh) * | 2008-07-17 | 2014-10-01 | 默克专利有限公司 | 有机电致发光器件 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101300029B1 (ko) * | 2005-06-30 | 2013-08-29 | 코닌클리즈케 필립스 일렉트로닉스 엔.브이. | 전계발광 금속 착체 |
WO2008117633A1 (en) * | 2007-03-23 | 2008-10-02 | Semiconductor Energy Laboratory Co., Ltd. | Composition, method for fabricating light-emitting element, light-emitting element, light-emitting device, and electronic device |
JP5458890B2 (ja) * | 2007-11-08 | 2014-04-02 | 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 |
JP5733663B2 (ja) * | 2011-04-27 | 2015-06-10 | 公立大学法人大阪市立大学 | 錯体 |
EP2757608B1 (en) | 2011-09-12 | 2016-03-23 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
JPWO2013038929A1 (ja) | 2011-09-12 | 2015-03-26 | 新日鉄住金化学株式会社 | 含ケイ素四員環構造を有する有機電界発光素子用材料及び有機電界発光素子 |
WO2013088934A1 (ja) | 2011-12-12 | 2013-06-20 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びそれを用いた有機電界発光素子 |
KR102005723B1 (ko) | 2012-03-12 | 2019-07-31 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자 |
KR102014888B1 (ko) | 2012-06-28 | 2019-08-27 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계발광 소자용 재료 및 유기 전계발광 소자 |
JP6169078B2 (ja) | 2012-07-19 | 2017-07-26 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
TWI599570B (zh) | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
GB2522457B (en) * | 2014-01-24 | 2016-05-25 | Cambridge Display Tech Ltd | Compound, composition and organic light-emitting device |
KR102455107B1 (ko) | 2016-07-25 | 2022-10-14 | 메르크 파텐트 게엠베하 | 트리포달 두자리 부분 리간드를 함유하는 이핵 및 올리고핵 금속 착물 및 전자 소자에서의 이들의 용도 |
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KR200276545Y1 (ko) * | 1999-05-07 | 2002-05-24 | 김학교 | 고압살수기 |
EP2566302B1 (en) | 2000-08-11 | 2015-12-16 | The Trustees of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorence |
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 |
JP4154138B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP4299144B2 (ja) * | 2001-12-26 | 2009-07-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フッ素化フェニルピリジン、フェニルピリミジン、およびフェニルキノリンを含むエレクトロルミネッセンスイリジウム化合物ならびにこのような化合物を用いて製造されるデバイス |
KR200286950Y1 (ko) * | 2002-05-31 | 2002-08-24 | 원 회 양 | 경량 방파제 구조 |
EP1394171A1 (de) * | 2002-08-09 | 2004-03-03 | Bayer Aktiengesellschaft | Mehrkernige Metallkomplexe als Phosphoreszenzemitter in elektrolumineszierenden Schichtanordnungen |
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2003
- 2003-09-06 KR KR1020030062371A patent/KR100718100B1/ko active IP Right Grant
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2004
- 2004-08-26 EP EP04255158A patent/EP1538153A1/en not_active Withdrawn
- 2004-09-02 US US10/932,228 patent/US7306857B2/en active Active
- 2004-09-06 CN CNB200410068766XA patent/CN100456525C/zh not_active Expired - Lifetime
- 2004-09-06 JP JP2004258987A patent/JP4713864B2/ja not_active Expired - Lifetime
Cited By (3)
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CN101016317B (zh) * | 2006-02-11 | 2013-02-20 | 三星显示有限公司 | 环金属化过渡金属络合物及使用其的有机电致发光器件 |
CN102317405A (zh) * | 2008-07-16 | 2012-01-11 | 索尔维公司 | 包括多核络合物的发光材料 |
CN102076817B (zh) * | 2008-07-17 | 2014-10-01 | 默克专利有限公司 | 有机电致发光器件 |
Also Published As
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US20050069728A1 (en) | 2005-03-31 |
JP4713864B2 (ja) | 2011-06-29 |
CN100456525C (zh) | 2009-01-28 |
JP2005082598A (ja) | 2005-03-31 |
KR100718100B1 (ko) | 2007-05-14 |
US7306857B2 (en) | 2007-12-11 |
KR20050026750A (ko) | 2005-03-16 |
EP1538153A1 (en) | 2005-06-08 |
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