CN100530745C - 具有导电聚合物的电致发磷光排列 - Google Patents
具有导电聚合物的电致发磷光排列 Download PDFInfo
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- CN100530745C CN100530745C CNB028205308A CN02820530A CN100530745C CN 100530745 C CN100530745 C CN 100530745C CN B028205308 A CNB028205308 A CN B028205308A CN 02820530 A CN02820530 A CN 02820530A CN 100530745 C CN100530745 C CN 100530745C
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- 229920001940 conductive polymer Polymers 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000000758 substrate Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 23
- -1 polypropylene Polymers 0.000 claims description 22
- 230000005611 electricity Effects 0.000 claims description 15
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 10
- 230000005684 electric field Effects 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- 229920000123 polythiophene Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 4
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims description 4
- 239000004695 Polyether sulfone Substances 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 238000010276 construction Methods 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229920006393 polyether sulfone Polymers 0.000 claims description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000002908 osmium compounds Chemical class 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920000128 polypyrrole Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 description 25
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 16
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
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- 238000000034 method Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
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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
- 238000004519 manufacturing process Methods 0.000 description 6
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- 125000001624 naphthyl group Chemical group 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
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- 239000011248 coating agent Substances 0.000 description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 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 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 208000037656 Respiratory Sounds Diseases 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical group OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008521 reorganization Effects 0.000 description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002259 gallium compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000005622 photoelectricity Effects 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 230000003746 surface roughness Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical class 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 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
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003208 poly(ethylene sulfide) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
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- 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
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- 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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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims (15)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10150477A DE10150477A1 (de) | 2001-10-16 | 2001-10-16 | Elektrophosphoreszierende Anordnung mit leitfähigen Polymeren |
DE10150477.2 | 2001-10-16 |
Publications (2)
Publication Number | Publication Date |
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CN1572031A CN1572031A (zh) | 2005-01-26 |
CN100530745C true CN100530745C (zh) | 2009-08-19 |
Family
ID=7702335
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB028205308A Expired - Fee Related CN100530745C (zh) | 2001-10-16 | 2002-10-04 | 具有导电聚合物的电致发磷光排列 |
Country Status (11)
Country | Link |
---|---|
US (1) | US6869697B2 (zh) |
EP (1) | EP1438756B1 (zh) |
JP (1) | JP2005506665A (zh) |
KR (2) | KR101218962B1 (zh) |
CN (1) | CN100530745C (zh) |
AT (1) | ATE392017T1 (zh) |
DE (2) | DE10150477A1 (zh) |
ES (1) | ES2303861T3 (zh) |
HK (1) | HK1073390A1 (zh) |
TW (1) | TWI242036B (zh) |
WO (1) | WO2003034512A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3605083B2 (ja) * | 2002-02-27 | 2004-12-22 | 三洋電機株式会社 | 発光素子用発光材料及び有機エレクトロルミネッセント素子 |
JP4683924B2 (ja) * | 2002-12-19 | 2011-05-18 | 株式会社半導体エネルギー研究所 | 発光材料、電界発光素子、及び発光装置 |
JP4858169B2 (ja) * | 2004-07-23 | 2012-01-18 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
US7737434B2 (en) * | 2004-11-25 | 2010-06-15 | Showa Denko K.K. | Light-emitting diode illumination source |
US20060177690A1 (en) * | 2005-02-07 | 2006-08-10 | Osram Opto Semiconductors Gmbh & Co. Ohg | Tri-layer PLED devices with both room-temperature and high-temperature operational stability |
KR101258311B1 (ko) * | 2006-12-18 | 2013-04-25 | 삼성전자주식회사 | 이리듐 유기금속 화합물을 이용한 유기 메모리 소자 및그의 제조방법 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NO170326C (no) | 1988-08-12 | 1992-10-07 | Bayer Ag | Dihydroksydifenylcykloalkaner |
US5227458A (en) | 1988-08-12 | 1993-07-13 | Bayer Aktiengesellschaft | Polycarbonate from dihydroxydiphenyl cycloalkane |
EP0440957B1 (de) | 1990-02-08 | 1996-03-27 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
JP3069139B2 (ja) | 1990-03-16 | 2000-07-24 | 旭化成工業株式会社 | 分散型電界発光素子 |
EP0602713B1 (en) | 1992-12-17 | 1998-10-14 | Agfa-Gevaert N.V. | Permanent antistatic primer layer |
DE19507413A1 (de) * | 1994-05-06 | 1995-11-09 | Bayer Ag | Leitfähige Beschichtungen |
US5719467A (en) | 1995-07-27 | 1998-02-17 | Hewlett-Packard Company | Organic electroluminescent device |
DE19627071A1 (de) * | 1996-07-05 | 1998-01-08 | Bayer Ag | Elektrolumineszierende Anordnungen |
RU2123773C1 (ru) | 1998-04-20 | 1998-12-20 | Некоммерческое партнерство "Полимерная электроника" | Электролюминесцентное устройство и способ его изготовления |
DE19824127A1 (de) * | 1998-05-29 | 1999-12-02 | Bayer Ag | Elektrochrome Anordnung auf Basis von Poly-(3,4-ethylendioxy-thiophen)-Derivaten in Kombination mit einer Gegenelektrode, die Metalloxide aus der VI. oder VIII. Nebengruppe enthält |
DE19824126A1 (de) * | 1998-05-29 | 1999-12-02 | Bayer Ag | UV-geschützte elektrochrome Anordnung auf Basis von Poly-(3,4-ethylendioxy-thiophen)-Derivaten |
DE19824186A1 (de) * | 1998-05-29 | 1999-12-02 | Bayer Ag | Elektrochrome Anordnung auf Basis von Poly-(3,4-ethylendioxy-thiophen)-Derivaten und Gel-Elektrolyt mit UV-Schutz |
DE19839947A1 (de) * | 1998-09-02 | 2000-03-09 | Bayer Ag | Elektrolumineszierende Anordnungen mit Thiophencarboxylat-Metallkomplexen |
JP3893774B2 (ja) * | 1998-10-26 | 2007-03-14 | セイコーエプソン株式会社 | 電界発光素子およびその製造方法 |
US6312304B1 (en) * | 1998-12-15 | 2001-11-06 | E Ink Corporation | Assembly of microencapsulated electronic displays |
CN100382354C (zh) * | 1999-02-15 | 2008-04-16 | 出光兴产株式会社 | 有机场致发光元件及其制造方法 |
DE29908783U1 (de) * | 1999-05-19 | 1999-09-09 | Me Technology Europe GmbH, 04430 Dölzig | Eingabegerät für Geschäftsvorfälle |
US6372154B1 (en) * | 1999-12-30 | 2002-04-16 | Canon Kabushiki Kaisha | Luminescent ink for printing of organic luminescent devices |
JP2001244077A (ja) * | 2000-03-01 | 2001-09-07 | Fuji Photo Film Co Ltd | 有機発光素子 |
US6392250B1 (en) * | 2000-06-30 | 2002-05-21 | Xerox Corporation | Organic light emitting devices having improved performance |
US6614175B2 (en) * | 2001-01-26 | 2003-09-02 | Xerox Corporation | Organic light emitting devices |
US6756474B2 (en) * | 2001-02-09 | 2004-06-29 | E. I. Du Pont De Nemours And Company | Aqueous conductive dispersions of polyaniline having enhanced viscosity |
SG105534A1 (en) * | 2001-03-07 | 2004-08-27 | Bayer Ag | Multilayered arrangement for electro-optical devices |
-
2001
- 2001-10-16 DE DE10150477A patent/DE10150477A1/de not_active Withdrawn
-
2002
- 2002-09-20 US US10/251,597 patent/US6869697B2/en not_active Expired - Fee Related
- 2002-10-04 ES ES02774685T patent/ES2303861T3/es not_active Expired - Lifetime
- 2002-10-04 KR KR1020107005934A patent/KR101218962B1/ko not_active IP Right Cessation
- 2002-10-04 WO PCT/EP2002/011130 patent/WO2003034512A1/de active Application Filing
- 2002-10-04 AT AT02774685T patent/ATE392017T1/de active
- 2002-10-04 JP JP2003537134A patent/JP2005506665A/ja active Pending
- 2002-10-04 CN CNB028205308A patent/CN100530745C/zh not_active Expired - Fee Related
- 2002-10-04 KR KR1020047005523A patent/KR20050033536A/ko not_active Application Discontinuation
- 2002-10-04 EP EP02774685A patent/EP1438756B1/de not_active Expired - Lifetime
- 2002-10-04 DE DE50212080T patent/DE50212080D1/de not_active Expired - Lifetime
- 2002-10-15 TW TW091123627A patent/TWI242036B/zh not_active IP Right Cessation
-
2005
- 2005-07-19 HK HK05106106.3A patent/HK1073390A1/xx not_active IP Right Cessation
Non-Patent Citations (5)
Title |
---|
"plastic" LED: a flexible light-emitting device using apolyaniline transparent electrode. GUSTAFSSON G ET AL.Synthetic Metals,Vol.57 No.1. 1993 |
"plastic" LED: a flexible light-emitting device using apolyaniline transparent electrode. GUSTAFSSON G ET AL.Synthetic Metals,Vol.57 No.1. 1993 * |
. . |
characteristics of organic electroluminescent devices usingpolypyrrole conducting layer and undoped conjugatedpolymer layer. PARK J-W et al.Thin Solid Films,Vol.363 No.1-2. 2000 |
characteristics of organic electroluminescent devices usingpolypyrrole conducting layer and undoped conjugatedpolymer layer. PARK J-W et al.Thin Solid Films,Vol.363 No.1-2. 2000 * |
Also Published As
Publication number | Publication date |
---|---|
DE10150477A1 (de) | 2003-04-17 |
ES2303861T3 (es) | 2008-09-01 |
KR20050033536A (ko) | 2005-04-12 |
DE50212080D1 (de) | 2008-05-21 |
US20030108769A1 (en) | 2003-06-12 |
TWI242036B (en) | 2005-10-21 |
US6869697B2 (en) | 2005-03-22 |
CN1572031A (zh) | 2005-01-26 |
JP2005506665A (ja) | 2005-03-03 |
EP1438756B1 (de) | 2008-04-09 |
KR101218962B1 (ko) | 2013-01-04 |
WO2003034512A1 (de) | 2003-04-24 |
EP1438756A1 (de) | 2004-07-21 |
ATE392017T1 (de) | 2008-04-15 |
KR20100036393A (ko) | 2010-04-07 |
HK1073390A1 (en) | 2005-09-30 |
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