TWI247016B - Novel polythiophene dispersions - Google Patents
Novel polythiophene dispersions Download PDFInfo
- Publication number
- TWI247016B TWI247016B TW091104445A TW91104445A TWI247016B TW I247016 B TWI247016 B TW I247016B TW 091104445 A TW091104445 A TW 091104445A TW 91104445 A TW91104445 A TW 91104445A TW I247016 B TWI247016 B TW I247016B
- Authority
- TW
- Taiwan
- Prior art keywords
- polythiophene
- solution
- patent application
- dispersant
- ion complex
- Prior art date
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- 229920000123 polythiophene Polymers 0.000 title claims abstract description 38
- 239000006185 dispersion Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 239000011877 solvent mixture Substances 0.000 claims abstract description 4
- 239000002270 dispersing agent Substances 0.000 claims description 36
- 150000002500 ions Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 13
- -1 alkyl radical Chemical class 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 6
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 150000007519 polyprotic acids Polymers 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 3
- 239000003791 organic solvent mixture Substances 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical group N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000002079 cooperative effect Effects 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910017053 inorganic salt Inorganic materials 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 22
- 238000000576 coating method Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- WJMXTYZCTXTFJM-UHFFFAOYSA-N 1,1,1,2-tetraethoxydecane Chemical compound C(C)OC(C(OCC)(OCC)OCC)CCCCCCCC WJMXTYZCTXTFJM-UHFFFAOYSA-N 0.000 description 1
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000005569 Iron sulphate Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000015111 chews Nutrition 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 238000010137 moulding (plastic) Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NRYGNLJQFASBEF-UHFFFAOYSA-N thiophene-2,3-diol Chemical compound OC=1C=CSC=1O NRYGNLJQFASBEF-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/56—Solid electrolytes, e.g. gels; Additives therein
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electrochemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Electroluminescent Light Sources (AREA)
- Secondary Cells (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10111790A DE10111790A1 (de) | 2001-03-12 | 2001-03-12 | Neue Polythiophen-Dispersionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI247016B true TWI247016B (en) | 2006-01-11 |
Family
ID=7677127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091104445A TWI247016B (en) | 2001-03-12 | 2002-03-11 | Novel polythiophene dispersions |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US7008562B2 (enExample) |
| EP (1) | EP1373356B1 (enExample) |
| JP (2) | JP4225785B2 (enExample) |
| KR (1) | KR100856954B1 (enExample) |
| CN (1) | CN1219807C (enExample) |
| AT (1) | ATE294828T1 (enExample) |
| DE (2) | DE10111790A1 (enExample) |
| ES (1) | ES2240731T3 (enExample) |
| RU (1) | RU2299893C2 (enExample) |
| TW (1) | TWI247016B (enExample) |
| WO (1) | WO2002072660A1 (enExample) |
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| DE10103416A1 (de) * | 2001-01-26 | 2002-08-01 | Bayer Ag | Elektrolumineszierende Anordnungen |
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| DE10111790A1 (de) * | 2001-03-12 | 2002-09-26 | Bayer Ag | Neue Polythiophen-Dispersionen |
| WO2003048229A1 (en) | 2001-12-04 | 2003-06-12 | Agfa-Gevaert | Composition containing a polymer or copolymer of a 3,4-dialkoxythiophene and non-aqueous solvent |
| US7122130B2 (en) | 2001-12-04 | 2006-10-17 | Agfa Gevaert | Composition containing a polymer or copolymer of a 3,4-dialkoxythiophene and non-aqueous solvent |
| JP2005529474A (ja) * | 2002-06-14 | 2005-09-29 | シーメンス アクチエンゲゼルシヤフト | 導電性有機機能層を製造するための材料および該材料の使用 |
| WO2003107454A2 (de) * | 2002-06-14 | 2003-12-24 | Siemens Aktiengesellschaft | Material für eine dünne und niedrig leitfähige funktionsschicht für eine oled und herstellungsverfahren dazu |
| EP1514318A2 (de) * | 2002-06-14 | 2005-03-16 | Konarka Technologies, Inc. | MATERIAL FüR EINE FUNKTIONSSCHICHT EINES ORGANISCHEN ELEKTRONIKBAUTEILS HERSTELLUNGSVERFAHREN UND VERWENDUNG DAZU |
| US7317048B2 (en) * | 2003-01-06 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Variable resistance poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonate) for use in electronic devices |
| US7179534B2 (en) * | 2003-01-31 | 2007-02-20 | Princeton University | Conductive-polymer electronic switch |
| US6656763B1 (en) * | 2003-03-10 | 2003-12-02 | Advanced Micro Devices, Inc. | Spin on polymers for organic memory devices |
| DE102004006583A1 (de) * | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
| JP2007297637A (ja) * | 2005-02-16 | 2007-11-15 | Nissan Chem Ind Ltd | 固有導電性高分子の有機溶媒分散液 |
| CN1942510B (zh) * | 2005-02-16 | 2011-01-19 | 日产化学工业株式会社 | 固有导电性高分子的有机溶剂分散液的制造方法 |
| US20090120775A1 (en) * | 2005-11-16 | 2009-05-14 | Yoshiyuki Morita | Conductive resin composition, conductive film comprising the same, and resistive-film switch employing the same |
| KR20070096102A (ko) * | 2005-12-23 | 2007-10-02 | 삼성전자주식회사 | 현상기의 현상제 레벨 감지장치 및 그것이 구비된 화상형성장치 |
| US20080097009A1 (en) * | 2006-02-10 | 2008-04-24 | Tadayuki Isaji | Method for production of organic solvent dispersion of intrinsically conductive polymer |
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| EP2050778B1 (en) | 2006-08-10 | 2012-11-28 | Nissan Chemical Industries, Ltd. | Process for producing dispersion liquid of intrinsic electroconductive polymer in organic solvent |
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| DE102008003251A1 (de) | 2008-01-04 | 2009-07-09 | Ormecon Gmbh | Verfahren zur Herstellung von erhöhte Leitfähigkeit aufweisenden Beschichtungen auf Basis von Polythiophen und dessen Derivaten |
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| EP2105458A1 (en) | 2008-03-27 | 2009-09-30 | Agfa-Gevaert | Dispersable polythiophene composition. |
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| WO2010013660A1 (ja) | 2008-07-29 | 2010-02-04 | 日産化学工業株式会社 | 導電性コーティング組成物 |
| JP5470831B2 (ja) * | 2008-12-17 | 2014-04-16 | 東洋インキＳｃホールディングス株式会社 | ポリチオフェン組成物、およびそれを用いてなる導電膜、ならびに積層体 |
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| DE102013008460A1 (de) | 2013-05-21 | 2014-11-27 | Heraeus Precious Metals Gmbh & Co. Kg | Unpolare Lösungsmittel als Haftvermittler-Additiv in PEDOT/PSS-Dispersionen |
| JP6379523B2 (ja) * | 2013-04-04 | 2018-08-29 | 東ソー株式会社 | 導電性高分子水溶液、及び導電性高分子膜 |
| JP6311355B2 (ja) * | 2014-01-27 | 2018-04-18 | 東ソー株式会社 | 導電性高分子水溶液、及び導電性高分子膜 |
| JP6427887B2 (ja) * | 2014-02-05 | 2018-11-28 | 東ソー株式会社 | 導電性高分子水溶液、及び導電性高分子膜 |
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| JP7167570B2 (ja) * | 2017-11-09 | 2022-11-09 | 東ソー株式会社 | 導電性高分子水溶液、導電性高分子膜、及び被覆物品 |
| EP3587506B1 (en) * | 2018-06-28 | 2023-04-05 | Heraeus Deutschland GmbH & Co. KG | Liquid compositions comprising particles of a conductive polymer and an organic solvent forming an azeotrope with water |
| CN112889123A (zh) | 2018-08-10 | 2021-06-01 | 阿维科斯公司 | 包含本征导电聚合物的固体电解电容器 |
| JP7426986B2 (ja) | 2018-08-10 | 2024-02-02 | キョーセラ・エイブイエックス・コンポーネンツ・コーポレーション | ポリアニリンを含む固体電解キャパシタ |
| US11114250B2 (en) | 2018-08-10 | 2021-09-07 | Avx Corporation | Solid electrolytic capacitor formed from conductive polymer particles |
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| WO2020236573A1 (en) | 2019-05-17 | 2020-11-26 | Avx Corporation | Solid electrolytic capacitor |
| WO2021055707A1 (en) | 2019-09-18 | 2021-03-25 | Avx Corporation | Solid electroltyic capacitor for use at high voltages |
| US11776759B2 (en) | 2019-12-10 | 2023-10-03 | KYOCER AVX Components Corporation | Tantalum capacitor with increased stability |
| US11823846B2 (en) | 2019-12-10 | 2023-11-21 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor containing a pre-coat and intrinsically conductive polymer |
| RU2770151C2 (ru) * | 2020-01-31 | 2022-04-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет" (СПбГУ) | Полимерные полихинон-политиофеновые композиции для электрохимических источников тока |
| CN111393678B (zh) * | 2020-03-27 | 2023-03-28 | 徐宁 | 水性聚合物的有机溶剂分散液的制备方法 |
| WO2021205873A1 (ja) | 2020-04-06 | 2021-10-14 | 信越化学工業株式会社 | 導電性高分子組成物、基板、及び基板の製造方法 |
| US12398288B2 (en) | 2020-06-03 | 2025-08-26 | Shin-Etsu Chemical Co., Ltd. | Conductive polymer composition, substrate, and method for producing substrate |
| US11631548B2 (en) | 2020-06-08 | 2023-04-18 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor containing a moisture barrier |
| JP7492484B2 (ja) | 2021-03-31 | 2024-05-29 | 信越化学工業株式会社 | 導電性高分子組成物、基板、及び基板の製造方法 |
| CN116239803B (zh) * | 2023-02-28 | 2025-04-04 | 华中科技大学 | 一种溶剂交换制备醇相导电聚合物、方法及应用 |
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| EP0253594A3 (en) | 1986-07-16 | 1989-10-11 | COOKSON GROUP plc | Polymerisable thiophene monomers, their production and polymers prepared therefrom |
| DE3814730A1 (de) | 1988-04-30 | 1989-11-09 | Bayer Ag | Feststoff-elektrolyte und diese enthaltende elektrolyt-kondensatoren |
| DE59010247D1 (de) * | 1990-02-08 | 1996-05-02 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
| DE4202337A1 (de) | 1992-01-29 | 1993-08-05 | Bayer Ag | Verfahren zur durchkontaktierung von zweilagigen leiterplatten und multilayern |
| DE19627071A1 (de) | 1996-07-05 | 1998-01-08 | Bayer Ag | Elektrolumineszierende Anordnungen |
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| RU2154817C2 (ru) * | 1997-10-01 | 2000-08-20 | Ельяшевич Галина Казимировна | Электропроводящая композиционная полимерная мембрана |
| DE19757542A1 (de) * | 1997-12-23 | 1999-06-24 | Bayer Ag | Siebdruckpaste zur Herstellung elektrisch leitfähiger Beschichtungen |
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| US6692662B2 (en) * | 2001-02-16 | 2004-02-17 | Elecon, Inc. | Compositions produced by solvent exchange methods and uses thereof |
| US6692663B2 (en) * | 2001-02-16 | 2004-02-17 | Elecon, Inc. | Compositions produced by solvent exchange methods and uses thereof |
| DE10111790A1 (de) * | 2001-03-12 | 2002-09-26 | Bayer Ag | Neue Polythiophen-Dispersionen |
| JP4049744B2 (ja) * | 2001-12-04 | 2008-02-20 | アグフア−ゲヴエルト，ナームローゼ・フエンノートシヤツプ | ポリチオフェンまたはチオフェン共重合体の水性もしくは非水性溶液または分散液の製造方法 |
-
2001
- 2001-03-12 DE DE10111790A patent/DE10111790A1/de not_active Withdrawn
-
2002
- 2002-02-27 AT AT02722144T patent/ATE294828T1/de active
- 2002-02-27 CN CNB028064194A patent/CN1219807C/zh not_active Expired - Lifetime
- 2002-02-27 KR KR1020037011890A patent/KR100856954B1/ko not_active Expired - Lifetime
- 2002-02-27 EP EP02722144A patent/EP1373356B1/de not_active Expired - Lifetime
- 2002-02-27 ES ES02722144T patent/ES2240731T3/es not_active Expired - Lifetime
- 2002-02-27 DE DE50203008T patent/DE50203008D1/de not_active Expired - Lifetime
- 2002-02-27 RU RU2003130279/04A patent/RU2299893C2/ru not_active IP Right Cessation
- 2002-02-27 WO PCT/EP2002/002066 patent/WO2002072660A1/de not_active Ceased
- 2002-02-27 JP JP2002571564A patent/JP4225785B2/ja not_active Expired - Lifetime
- 2002-03-07 US US10/093,219 patent/US7008562B2/en not_active Expired - Fee Related
- 2002-03-11 TW TW091104445A patent/TWI247016B/zh not_active IP Right Cessation
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- 2005-11-29 US US11/288,703 patent/US20060071201A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1373356A1 (de) | 2004-01-02 |
| JP2004532298A (ja) | 2004-10-21 |
| DE50203008D1 (de) | 2005-06-09 |
| HK1063641A1 (en) | 2005-01-07 |
| RU2003130279A (ru) | 2005-04-10 |
| CN1219807C (zh) | 2005-09-21 |
| US20020173579A1 (en) | 2002-11-21 |
| US7008562B2 (en) | 2006-03-07 |
| US20130059953A1 (en) | 2013-03-07 |
| JP4225785B2 (ja) | 2009-02-18 |
| CN1496382A (zh) | 2004-05-12 |
| DE10111790A1 (de) | 2002-09-26 |
| JP2009046687A (ja) | 2009-03-05 |
| ATE294828T1 (de) | 2005-05-15 |
| JP5183395B2 (ja) | 2013-04-17 |
| ES2240731T3 (es) | 2005-10-16 |
| KR100856954B1 (ko) | 2008-09-04 |
| KR20030082974A (ko) | 2003-10-23 |
| US20060071201A1 (en) | 2006-04-06 |
| EP1373356B1 (de) | 2005-05-04 |
| RU2299893C2 (ru) | 2007-05-27 |
| WO2002072660A1 (de) | 2002-09-19 |
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