CN1662628A - 可溶液加工的磷光材料 - Google Patents
可溶液加工的磷光材料 Download PDFInfo
- Publication number
- CN1662628A CN1662628A CN03814689.4A CN03814689A CN1662628A CN 1662628 A CN1662628 A CN 1662628A CN 03814689 A CN03814689 A CN 03814689A CN 1662628 A CN1662628 A CN 1662628A
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- CN
- China
- Prior art keywords
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- oligopolymer
- polymkeric substance
- organo
- metallic
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 124
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 88
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 239000000126 substance Substances 0.000 claims description 132
- 239000004327 boric acid Substances 0.000 claims description 45
- 229910052751 metal Inorganic materials 0.000 claims description 43
- 239000002184 metal Substances 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 36
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000004820 halides Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 18
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 17
- 229910000085 borane Inorganic materials 0.000 claims description 16
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002800 charge carrier Substances 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 9
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005259 triarylamine group Chemical class 0.000 claims description 7
- 150000004867 thiadiazoles Chemical class 0.000 claims description 6
- 150000003577 thiophenes Chemical class 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 239000010970 precious metal Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 48
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- 229910052741 iridium Inorganic materials 0.000 description 44
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- 239000000243 solution Substances 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 28
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- 229910052796 boron Inorganic materials 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- FBQFCXDBCPREBP-UHFFFAOYSA-N 2-(4-bromophenyl)pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=N1 FBQFCXDBCPREBP-UHFFFAOYSA-N 0.000 description 14
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- 229910052794 bromium Inorganic materials 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
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- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
- 229910006400 μ-Cl Inorganic materials 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
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- 239000000539 dimer Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 5
- 238000005424 photoluminescence Methods 0.000 description 5
- -1 polyphenylene Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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- 241000276489 Merlangius merlangus Species 0.000 description 4
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
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- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 3
- UOPGXWZUDYOQEJ-UHFFFAOYSA-N 1-bromo-9,9-dioctylfluorene Chemical compound BrC1=CC=CC=2C3=CC=CC=C3C(C1=2)(CCCCCCCC)CCCCCCCC UOPGXWZUDYOQEJ-UHFFFAOYSA-N 0.000 description 3
- GQHAIOTZSHWLNY-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)-4-bromopyridine Chemical compound BrC1=CC(=NC=C1)C1=CC2=C(S1)C=CC=C2 GQHAIOTZSHWLNY-UHFFFAOYSA-N 0.000 description 3
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
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- DLTYISPGIFKYAD-UHFFFAOYSA-N [SiH3]C1=CC=CC=2C3=CC=CC=C3C(C12)(CCCCCCCC)CCCCCCCC Chemical compound [SiH3]C1=CC=CC=2C3=CC=CC=C3C(C12)(CCCCCCCC)CCCCCCCC DLTYISPGIFKYAD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
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- NPRDEIDCAUHOJU-UHFFFAOYSA-N [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NPRDEIDCAUHOJU-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
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- 229920006237 degradable polymer Polymers 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
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- 239000011229 interlayer Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000011022 operating instruction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
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- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
体系 | Lum.max(cd/m2) | 启动电压(V) | CIE X | CIE Y | 效率(cd/A) | ELQY(%) | 颜色 |
LNOP | 60434001400 | 4.05.05.56.0 | 0.370.480.480.46 | 0.590.510.510.53 | 2.5*10-39.9*10-36.9*10-27.3*10-2 | 7.4*10-43.3*10-32.2*10-27.3*10-2 | 黄绿色绿黄色黄色绿黄色 |
体系 | Lum.max(cd/m2) | 启动电压(V) | CIE X | CIE Y | 效率(cd/A) | ELQY(%) | 颜色 |
PF8中的LPF8中的N | 225190 | 5.57.5 | 0.350.44 | 0.480.52 | 0.160.15 | 7.6*10-25.6*10-2 | 黄绿色绿黄色 |
体系 | Lum.max(cd/m2) | 启动电压(V) | CIE X | CIE Y | 效率(cd/A) | ELQY(%) | 颜色 |
R1 | 10 | 8.5 | 0.29 | 0.45 | 7.0*10-2 | 2.6*10-2 | 黄绿色 |
R2S1S2S3 | 6042163304 | 8.59.57.06.0 | 0.330.420.470.42 | 0.440.340.430.40 | 0.137.6*10-20.190.18 | 7.1*10-23.6*10-27.9*10-27.9*10-2 | 黄绿色粉红色泛白色的橙色泛白色的橙色 |
Ir(1)-C(7)2.00(2)Ir(1)-C(20)2.02(2)Ir(1)-N(1)2.067(18)Ir(1)-N(2)2.074(17)Ir(1)-O(1)2.139(15)Ir(1)-O(2)2.133(14)C(7)-Ir(1)-C(20)92.1(8)C(7)-Ir(1)-N(1)80.5(8) | C(20)-Ir(1)-N(2)78.9(8)C(20)-Ir(1)-O(2)89.4(7)N(1)-Ir(1)-O(2)92.6(6)N(2)-Ir(1)-O(2)85.0(6)C(7)-Ir(1)-O(1)90.0(7)N(1)-Ir(1)-O(1)89.0(6)N(2)-Ir(1)-O(1)90.7(6)O(2)-Ir(1)-O(1)89.5(5) |
Claims (30)
Priority Applications (1)
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CN200710167957.5A CN101230264B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
Applications Claiming Priority (2)
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GB0209652.7 | 2002-04-26 | ||
GBGB0209652.7A GB0209652D0 (en) | 2002-04-26 | 2002-04-26 | Solution-processable phosphorescent materials |
Related Child Applications (2)
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CN200710167957.5A Division CN101230264B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
CN200710167956.0A Division CN101230263B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
Publications (2)
Publication Number | Publication Date |
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CN1662628A true CN1662628A (zh) | 2005-08-31 |
CN100355856C CN100355856C (zh) | 2007-12-19 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB038146894A Expired - Fee Related CN100355856C (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
CN200710167956.0A Expired - Fee Related CN101230263B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
CN200710167957.5A Expired - Fee Related CN101230264B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
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CN200710167956.0A Expired - Fee Related CN101230263B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
CN200710167957.5A Expired - Fee Related CN101230264B (zh) | 2002-04-26 | 2003-04-24 | 可溶液加工的磷光材料 |
Country Status (8)
Country | Link |
---|---|
US (1) | US9023978B2 (zh) |
EP (2) | EP1501907B1 (zh) |
JP (2) | JP5226927B2 (zh) |
CN (3) | CN100355856C (zh) |
AU (1) | AU2003227881A1 (zh) |
GB (1) | GB0209652D0 (zh) |
HK (1) | HK1081984A1 (zh) |
WO (1) | WO2003091355A2 (zh) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
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US8206838B2 (en) * | 2000-06-12 | 2012-06-26 | Sumitomo Chemical Co., Ltd. | Polymer matrix electroluminescent materials and devices |
US20060093852A1 (en) * | 2002-06-04 | 2006-05-04 | Dirk Marsitzky | Phosphorescent and luminescent conjugated polymers and their use in electroluminescent assemblies |
US7090929B2 (en) * | 2002-07-30 | 2006-08-15 | E.I. Du Pont De Nemours And Company | Metallic complexes covalently bound to conjugated polymers and electronic devices containing such compositions |
KR100798205B1 (ko) * | 2003-08-01 | 2008-01-24 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전기발광 소자 |
GB0329364D0 (en) | 2003-12-19 | 2004-01-21 | Cambridge Display Tech Ltd | Optical device |
DE10361385B4 (de) * | 2003-12-29 | 2011-07-28 | OSRAM Opto Semiconductors GmbH, 93055 | Polymere, phosphoreszierende, organisch halbleitende Emittermaterialien auf Basis perarylierter Borane, Verfahren zu deren Herstellung und Verwendungen davon |
GB0411582D0 (en) * | 2004-05-24 | 2004-06-23 | Cambridge Display Tech Ltd | Metal complex |
US7927717B2 (en) | 2004-06-30 | 2011-04-19 | Merck Patent Gmbh | Electroluminescent materials and devices |
GB0422391D0 (en) | 2004-10-08 | 2004-11-10 | Cambridge Display Tech Ltd | Light emitting device |
GB0427266D0 (en) | 2004-12-13 | 2005-01-12 | Cambridge Display Tech Ltd | Phosphorescent OLED |
TW200639193A (en) * | 2004-12-18 | 2006-11-16 | Merck Patent Gmbh | Electroluminescent polymers and their use |
WO2007063896A1 (ja) * | 2005-11-30 | 2007-06-07 | Sumitomo Chemical Company, Limited | 高分子系材料及びそれを用いた高分子発光素子 |
JP4804197B2 (ja) * | 2006-03-31 | 2011-11-02 | キヤノン株式会社 | 蛍光およびリン光を同時発光する有機化合物とそれを有する有機発光素子 |
US9118020B2 (en) | 2006-04-27 | 2015-08-25 | Global Oled Technology Llc | Electroluminescent devices including organic eil layer |
US9444065B2 (en) | 2006-05-12 | 2016-09-13 | The University Of Utah Research Foundation | π-conjugated heavy-metal polymers for organic white-light-emitting diodes |
KR20090013826A (ko) * | 2006-05-15 | 2009-02-05 | 닛토덴코 가부시키가이샤 | 발광 소자 및 조성물 |
JP2008013700A (ja) | 2006-07-07 | 2008-01-24 | Canon Inc | 発光材料及び発光素子 |
GB0617167D0 (en) | 2006-08-31 | 2006-10-11 | Cdt Oxford Ltd | Compounds for use in opto-electrical devices |
JP5444715B2 (ja) * | 2006-09-08 | 2014-03-19 | 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 |
US8034465B2 (en) | 2007-06-20 | 2011-10-11 | Global Oled Technology Llc | Phosphorescent oled having double exciton-blocking layers |
WO2009006550A1 (en) | 2007-07-05 | 2009-01-08 | Nitto Denko Corporation | Light emitting devices and compositions |
US20090179552A1 (en) | 2007-11-15 | 2009-07-16 | Jesse Froehlich | Light emitting devices and compositions |
GB2456788B (en) | 2008-01-23 | 2011-03-09 | Cambridge Display Tech Ltd | White light emitting material |
JP5609022B2 (ja) * | 2008-06-23 | 2014-10-22 | 住友化学株式会社 | 金属錯体の残基を含む高分子化合物及びそれを用いた素子 |
TWI477564B (zh) * | 2008-07-28 | 2015-03-21 | Sharp Kk | A polymer pigment material, a color conversion film thereof, and a multi-color light emitting organic EL device |
US8053536B2 (en) * | 2008-12-05 | 2011-11-08 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
US8048956B2 (en) * | 2008-12-05 | 2011-11-01 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
JP5720097B2 (ja) * | 2009-01-20 | 2015-05-20 | 住友化学株式会社 | メタフェニレン系高分子化合物及びそれを用いた発光素子 |
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US20060063026A1 (en) | 2006-03-23 |
GB0209652D0 (en) | 2002-06-05 |
EP2264123A3 (en) | 2012-07-18 |
CN101230264B (zh) | 2015-08-12 |
WO2003091355A2 (en) | 2003-11-06 |
CN101230263B (zh) | 2014-12-03 |
WO2003091355A3 (en) | 2004-03-04 |
EP1501907B1 (en) | 2016-07-27 |
JP5226927B2 (ja) | 2013-07-03 |
CN100355856C (zh) | 2007-12-19 |
US9023978B2 (en) | 2015-05-05 |
CN101230263A (zh) | 2008-07-30 |
AU2003227881A1 (en) | 2003-11-10 |
JP5836894B2 (ja) | 2015-12-24 |
CN101230264A (zh) | 2008-07-30 |
JP2005524725A (ja) | 2005-08-18 |
EP2264123A2 (en) | 2010-12-22 |
EP1501907A2 (en) | 2005-02-02 |
AU2003227881A8 (en) | 2003-11-10 |
EP2264123B1 (en) | 2016-12-28 |
JP2012229431A (ja) | 2012-11-22 |
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