JP4371818B2 - ３，４−アルキレンジオキシチオフェンコポリマー - Google Patents
３，４−アルキレンジオキシチオフェンコポリマー Download PDFInfo
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- JP4371818B2 JP4371818B2 JP2003554765A JP2003554765A JP4371818B2 JP 4371818 B2 JP4371818 B2 JP 4371818B2 JP 2003554765 A JP2003554765 A JP 2003554765A JP 2003554765 A JP2003554765 A JP 2003554765A JP 4371818 B2 JP4371818 B2 JP 4371818B2
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- JP
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- Prior art keywords
- water
- alkylenedioxythiophene
- copolymer
- solubility
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 239000006185 dispersion Substances 0.000 claims abstract description 48
- 229920000447 polyanionic polymer Polymers 0.000 claims abstract description 21
- 238000000576 coating method Methods 0.000 claims abstract description 7
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 30
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 57
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 15
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- -1 3,4-dihydro-2H-thieno [3,4-b] [1,4] dioxin-2-yl Chemical group 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- YFCHAINVYLQVBG-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethanol Chemical compound O1C(CO)COC2=CSC=C21 YFCHAINVYLQVBG-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229930192474 thiophene Natural products 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- UXHNWRUHTDYYAB-UHFFFAOYSA-N dimethyl 3-(acetyloxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylate Chemical compound O1C(COC(C)=O)COC2=C(C(=O)OC)SC(C(=O)OC)=C21 UXHNWRUHTDYYAB-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229920003171 Poly (ethylene oxide) Chemical group 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- MTPDXOGPSAQJHH-UHFFFAOYSA-N dimethyl 3-acetyloxy-3,4-dihydro-2h-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylate Chemical compound O1CC(OC(C)=O)COC2=C(C(=O)OC)SC(C(=O)OC)=C21 MTPDXOGPSAQJHH-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 229920000123 polythiophene Polymers 0.000 description 5
- NXFYICTWDZERRY-UHFFFAOYSA-N 3-(hydroxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid Chemical compound O1C(CO)COC2=C(C(O)=O)SC(C(O)=O)=C21 NXFYICTWDZERRY-UHFFFAOYSA-N 0.000 description 4
- JFRBXNTWJASGGD-UHFFFAOYSA-N 3h-dioxepin-3-ol Chemical compound OC1OOC=CC=C1 JFRBXNTWJASGGD-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 3
- WKUBGFWBSGWPEO-UHFFFAOYSA-N 2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)acetic acid Chemical compound O1C(COCC(=O)O)COC2=CSC=C21 WKUBGFWBSGWPEO-UHFFFAOYSA-N 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- WCRLHMRPQNFNMD-UHFFFAOYSA-N 3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1C(COCCOCCOCCOC)COC2=CSC=C21 WCRLHMRPQNFNMD-UHFFFAOYSA-N 0.000 description 3
- IEXLMWZQCURUMB-UHFFFAOYSA-N 3-acetyl-1-(dimethylamino)-4,4a,6,7,11,12-hexahydroxy-11-methyl-1,11a,12,12a-tetrahydrotetracene-2,5-dione Chemical compound C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(=O)C(C(C)=O)=C(O)C4(O)C(=O)C3=C(O)C2=C1O IEXLMWZQCURUMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- NJPLDVZZEPDJMS-UHFFFAOYSA-N 3-hydroxy-3,4-dihydro-2h-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid Chemical compound O1CC(O)COC2=C(C(O)=O)SC(C(O)=O)=C12 NJPLDVZZEPDJMS-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- CJNYCXOZPQVMIV-UHFFFAOYSA-M sodium;4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-1-sulfonate Chemical compound [Na+].O1C(COCCCCS(=O)(=O)[O-])COC2=CSC=C21 CJNYCXOZPQVMIV-UHFFFAOYSA-M 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 0 *CCCCOCC1COc2c[s]cc2OC1 Chemical compound *CCCCOCC1COc2c[s]cc2OC1 0.000 description 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- YJQSEUFVWQCHCP-UHFFFAOYSA-N 3,4-dihydroxythiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C=1SC(C(O)=O)=C(O)C=1O YJQSEUFVWQCHCP-UHFFFAOYSA-N 0.000 description 1
- ZZWUTHDEIXYWSO-UHFFFAOYSA-N 3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]propane-1,2-diol Chemical compound COCCOCCOCCOCC(O)CO ZZWUTHDEIXYWSO-UHFFFAOYSA-N 0.000 description 1
- LZGXDQKQLYLULZ-UHFFFAOYSA-N 3-acetyloxy-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid Chemical compound O1CC(OC(=O)C)COC2=C(C(O)=O)SC(C(O)=O)=C21 LZGXDQKQLYLULZ-UHFFFAOYSA-N 0.000 description 1
- WQYWXQCOYRZFAV-UHFFFAOYSA-N 3-octylthiophene Chemical compound CCCCCCCCC=1C=CSC=1 WQYWXQCOYRZFAV-UHFFFAOYSA-N 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- LBPAOAJASTZUNG-UHFFFAOYSA-N CC(COCC(O)=O)COc1c[s]cc1O Chemical compound CC(COCC(O)=O)COc1c[s]cc1O LBPAOAJASTZUNG-UHFFFAOYSA-N 0.000 description 1
- MKAMVQIBBFMRDG-UHFFFAOYSA-N CCOC(COCC(CO)Oc1c[s]cc1C)=O Chemical compound CCOC(COCC(CO)Oc1c[s]cc1C)=O MKAMVQIBBFMRDG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YFTXAGYUQYGHOR-UHFFFAOYSA-N OC1COC2=CSCC2OC1 Chemical compound OC1COC2=CSCC2OC1 YFTXAGYUQYGHOR-UHFFFAOYSA-N 0.000 description 1
- NDVHIVXONKKUGA-UHFFFAOYSA-N OC1COc2c[s]cc2OC1 Chemical compound OC1COc2c[s]cc2OC1 NDVHIVXONKKUGA-UHFFFAOYSA-N 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- KMGARVOVYXNAOF-UHFFFAOYSA-N benzpiperylone Chemical compound C1CN(C)CCC1N1C(=O)C(CC=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 KMGARVOVYXNAOF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- ZZVINKJCOXPIKL-UHFFFAOYSA-N dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate Chemical compound COC(=O)C=1SC(C(=O)OC)=C(O)C=1O ZZVINKJCOXPIKL-UHFFFAOYSA-N 0.000 description 1
- 125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 description 1
- WJDPOAZQXGLVHO-UHFFFAOYSA-L disodium 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCCCOCC1COc2cscc2O1.[O-]S(=O)(=O)CCCCOCC1COc2cscc2O1 WJDPOAZQXGLVHO-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000004984 smart glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PLCGLUBPQGIIQM-UHFFFAOYSA-M sodium 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-1-sulfonate Chemical compound [Na+].O1C=2C(OCC1COC(CCC)S(=O)(=O)[O-])=CSC=2 PLCGLUBPQGIIQM-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Paints Or Removers (AREA)
- Hybrid Cells (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01000779A EP1323763A1 (en) | 2001-12-20 | 2001-12-20 | 3,4-Alkylenedioxy-thiophene copolymers |
| PCT/EP2002/013157 WO2003054052A1 (en) | 2001-12-20 | 2002-11-22 | 3,4-alkylenedioxy-thiophene copolymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005513219A JP2005513219A (ja) | 2005-05-12 |
| JP2005513219A5 JP2005513219A5 (enExample) | 2006-01-05 |
| JP4371818B2 true JP4371818B2 (ja) | 2009-11-25 |
Family
ID=8176115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554765A Expired - Fee Related JP4371818B2 (ja) | 2001-12-20 | 2002-11-22 | ３，４−アルキレンジオキシチオフェンコポリマー |
Country Status (6)
| Country | Link |
|---|---|
| EP (2) | EP1323763A1 (enExample) |
| JP (1) | JP4371818B2 (enExample) |
| AU (1) | AU2002349042A1 (enExample) |
| DE (1) | DE60220095T2 (enExample) |
| TW (1) | TW200409789A (enExample) |
| WO (1) | WO2003054052A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1321483A1 (en) * | 2001-12-20 | 2003-06-25 | Agfa-Gevaert | 3,4-alkylenedioxythiophene compounds and polymers thereof |
| DE10206294A1 (de) * | 2002-02-15 | 2003-08-28 | Bayer Ag | Transparente Polythiophenschichten hoher Leitfähigkeit |
| DE10215706A1 (de) * | 2002-04-10 | 2003-11-06 | Bayer Ag | Alkylendioxythiophene und Poly(alkylendioxythiophen)e mit Urethangruppierungen enthaltenden Seitengruppen |
| JP4077675B2 (ja) | 2002-07-26 | 2008-04-16 | ナガセケムテックス株式会社 | ポリ（３，４−ジアルコキシチオフェン）とポリ陰イオンとの複合体の水分散体およびその製造方法 |
| DE10237577A1 (de) * | 2002-08-16 | 2004-02-26 | H.C. Starck Gmbh | Substituierte Poly(alkylendioxythiophene) als Feststoffelektrolyte in Elektrolytkondensatoren |
| JP4619660B2 (ja) * | 2004-02-04 | 2011-01-26 | 信越ポリマー株式会社 | 光電変換素子およびその製造方法 |
| DE10343873A1 (de) * | 2003-09-23 | 2005-04-21 | Starck H C Gmbh | Verfahren zur Reinigung von Thiophenen |
| DE102004006583A1 (de) | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
| WO2007143124A1 (en) * | 2006-06-01 | 2007-12-13 | E. I. Du Pont De Nemours And Company | Conductive polymer compositions |
| WO2009054814A1 (en) * | 2007-10-25 | 2009-04-30 | Agency For Science, Technology And Research | Functionalized poly (3,4-alkylenebridgedthiophene) (pabt) |
| WO2009094361A2 (en) | 2008-01-21 | 2009-07-30 | University Of Connecticut | Conjugated polymers from substituted 3,4-propylenedioxythiophene, compositions, method of making, and use thereof |
| JP4565522B2 (ja) * | 2008-10-31 | 2010-10-20 | テイカ株式会社 | 導電性高分子の分散液の製造方法、導電性高分子の分散液、導電性高分子およびその用途 |
| US8710177B2 (en) | 2009-12-04 | 2014-04-29 | Tayca Corporation | Conductive polymer and a solid electrolytic capacitor using the same as a solid electrolyte |
| US8535571B2 (en) | 2009-12-30 | 2013-09-17 | Korea University Research And Business Foundation | Water-soluble electrically conductive polymers |
| US8404515B2 (en) | 2010-03-25 | 2013-03-26 | The University Of Connecticut | Formation of conjugated polymers for solid-state devices |
| JP5682189B2 (ja) * | 2010-09-14 | 2015-03-11 | コニカミノルタ株式会社 | 光電変換素子、光電変換素子の製造方法および太陽電池 |
| EP2681255A4 (en) | 2011-03-02 | 2015-08-19 | Univ Connecticut | MONOMERS AND CONJUGATED SELENBASE POLYMERS, METHOD OF MANUFACTURING THEREOF AND USE THEREOF |
| JP5712873B2 (ja) * | 2011-09-02 | 2015-05-07 | コニカミノルタ株式会社 | 光電変換素子およびそれを含む太陽電池 |
| JP5751100B2 (ja) * | 2011-09-05 | 2015-07-22 | コニカミノルタ株式会社 | 色素増感型太陽電池及び製造方法 |
| TWI460203B (zh) * | 2011-12-30 | 2014-11-11 | Eternal Materials Co Ltd | 電解質材料調配物、由此形成之電解質材料組合物及其用途 |
| WO2014018472A1 (en) | 2012-07-23 | 2014-01-30 | The University Of Connecticut | Electrochromic copolymers from precursors, method of making, and use thereof |
| DE102012018976A1 (de) | 2012-09-27 | 2014-03-27 | Heraeus Precious Metals Gmbh & Co. Kg | Verwendung von Mischungen aus selbstdotierten und fremddotierten leitfähigen Polymeren in einem Kondensator |
| KR101526196B1 (ko) * | 2014-04-25 | 2015-06-08 | 주식회사 한국엔티켐 | 전도성 고분자 용액의 제조방법 및 이를 제조하기 위한 장치 |
| US10323178B2 (en) | 2014-05-16 | 2019-06-18 | The University Of Connecticut | Color tuning of electrochromic devices using an organic dye |
| EP3037497B1 (en) * | 2014-12-23 | 2025-02-26 | Heraeus Epurio GmbH | Process for producing functionalized polythiophenes |
| JP2016188348A (ja) * | 2015-03-30 | 2016-11-04 | 東ソー株式会社 | チオフェンポリマー、その組成物、及びその用途 |
| CZ2015452A3 (cs) * | 2015-06-30 | 2016-11-02 | Centrum organickĂ© chemie s.r.o. | Způsob vodivé a antistatické permanentní úpravy textilních materiálů a textilní materiál upravený tímto způsobem |
| WO2017011822A1 (en) | 2015-07-16 | 2017-01-19 | Georgia Tech Research Corporation | Processable polymers and methods of making and using thereof |
| JP6753092B2 (ja) * | 2016-03-22 | 2020-09-09 | 東ソー株式会社 | 水溶性導電性共重合体、その製造方法、及びその水溶液 |
| JP6919192B2 (ja) * | 2016-03-31 | 2021-08-18 | 東ソー株式会社 | 導電性高分子水溶液及びその用途 |
| JP7094137B2 (ja) * | 2017-05-08 | 2022-07-01 | 東ソー株式会社 | ３，４－エチレンジオキシチオフェン構造を有するスルホン酸エステル、およびそれから誘導されるポリ（３，４－エチレンジオキシチオフェン）誘導体の合成法 |
| CN112074558B (zh) * | 2018-05-04 | 2024-03-26 | 图尔库大学 | 制备pedot膜的方法 |
| JP7142466B2 (ja) * | 2018-05-22 | 2022-09-27 | 東ソー株式会社 | ３，４－エチレンジオキシチオフェン構造を有する共重合体 |
| JP7184274B2 (ja) * | 2018-09-11 | 2022-12-06 | 国立大学法人山梨大学 | 導電性高分子溶液の製造方法 |
| WO2022258501A1 (en) * | 2021-06-08 | 2022-12-15 | Agfa-Gevaert Nv | Novel polythiophene/polyanion compositions |
| EP4324866A1 (en) * | 2022-08-17 | 2024-02-21 | Heraeus Epurio GmbH | High purity sulfonated thiophene monomers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5111327A (en) * | 1991-03-04 | 1992-05-05 | General Electric Company | Substituted 3,4-polymethylenedioxythiophenes, and polymers and electro responsive devices made therefrom |
| DE19841804A1 (de) * | 1998-09-12 | 2000-03-16 | Bayer Ag | Leiterbahnen aus Polyalkylendioxythiophen |
-
2001
- 2001-12-20 EP EP01000779A patent/EP1323763A1/en not_active Withdrawn
-
2002
- 2002-11-22 WO PCT/EP2002/013157 patent/WO2003054052A1/en not_active Ceased
- 2002-11-22 EP EP02781326A patent/EP1458785B1/en not_active Expired - Lifetime
- 2002-11-22 DE DE60220095T patent/DE60220095T2/de not_active Expired - Lifetime
- 2002-11-22 AU AU2002349042A patent/AU2002349042A1/en not_active Abandoned
- 2002-11-22 JP JP2003554765A patent/JP4371818B2/ja not_active Expired - Fee Related
- 2002-12-04 TW TW091135114A patent/TW200409789A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200409789A (en) | 2004-06-16 |
| DE60220095D1 (de) | 2007-06-21 |
| EP1323763A1 (en) | 2003-07-02 |
| AU2002349042A1 (en) | 2003-07-09 |
| WO2003054052A1 (en) | 2003-07-03 |
| EP1458785A1 (en) | 2004-09-22 |
| DE60220095T2 (de) | 2008-01-10 |
| EP1458785B1 (en) | 2007-05-09 |
| JP2005513219A (ja) | 2005-05-12 |
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