JP2018123213A - ポリチオフェン及びその組成物、並びにその用途 - Google Patents
ポリチオフェン及びその組成物、並びにその用途 Download PDFInfo
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- JP2018123213A JP2018123213A JP2017015212A JP2017015212A JP2018123213A JP 2018123213 A JP2018123213 A JP 2018123213A JP 2017015212 A JP2017015212 A JP 2017015212A JP 2017015212 A JP2017015212 A JP 2017015212A JP 2018123213 A JP2018123213 A JP 2018123213A
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- Prior art keywords
- polythiophene
- group
- formula
- molecular weight
- dihydrothieno
- 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.)
- Granted
Links
- 229920000123 polythiophene Polymers 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 title claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- -1 amine compound Chemical class 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 17
- 230000014759 maintenance of location Effects 0.000 claims description 9
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 47
- 229930192474 thiophene Natural products 0.000 abstract description 23
- 150000001768 cations Chemical class 0.000 abstract description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract description 3
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical group O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 38
- 239000007800 oxidant agent Substances 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- 239000010408 film Substances 0.000 description 26
- 239000000178 monomer Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 15
- 229920001940 conductive polymer Polymers 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000001590 oxidative effect Effects 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000003990 capacitor Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 239000003729 cation exchange resin Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000002280 amphoteric surfactant Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002505 iron Chemical class 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 238000000108 ultra-filtration Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 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
- ZYNOESUJJLFWCB-UHFFFAOYSA-M sodium 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-2-sulfonate Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)[O-])C)=CSC2.[Na+] ZYNOESUJJLFWCB-UHFFFAOYSA-M 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OIRKLPHRLOQDLU-UHFFFAOYSA-N 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-1-sulfonic acid Chemical group O1C(COCCCCS(=O)(=O)O)COC2=CSC=C21 OIRKLPHRLOQDLU-UHFFFAOYSA-N 0.000 description 2
- DGLHVZNTYXDOSR-UHFFFAOYSA-N 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)butane-2-sulfonic acid Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)O)C)=CSC2 DGLHVZNTYXDOSR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000004373 Pullulan Substances 0.000 description 2
- 229920001218 Pullulan Polymers 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000007611 bar coating method Methods 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019423 pullulan Nutrition 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000006104 solid solution Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229910001428 transition metal ion Inorganic materials 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- DUEGWVMKCWNFPK-UHFFFAOYSA-N 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)-6-methylheptane-3-sulfonic acid Chemical compound CC(C)CCC(CCOCC1COc2cscc2O1)S(O)(=O)=O DUEGWVMKCWNFPK-UHFFFAOYSA-N 0.000 description 1
- FOWGLOZKDUVILH-UHFFFAOYSA-N 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)heptane-3-sulfonic acid Chemical compound CCCCC(CCOCC1COc2cscc2O1)S(O)(=O)=O FOWGLOZKDUVILH-UHFFFAOYSA-N 0.000 description 1
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-M octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-M 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- CLPMBSBBTZMITH-UHFFFAOYSA-M sodium 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)-5-methylhexane-3-sulfonate Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)[O-])CC(C)C)=CSC2.[Na+] CLPMBSBBTZMITH-UHFFFAOYSA-M 0.000 description 1
- TWQHZBCICZFXKQ-UHFFFAOYSA-M sodium 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)hexane-3-sulfonate Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)[O-])CCC)=CSC2.[Na+] TWQHZBCICZFXKQ-UHFFFAOYSA-M 0.000 description 1
- GJBFYQRGMOQENE-UHFFFAOYSA-M sodium 1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)nonane-3-sulfonate Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)[O-])CCCCCC)=CSC2.[Na+] GJBFYQRGMOQENE-UHFFFAOYSA-M 0.000 description 1
- OAJZFHFBPIVWMO-UHFFFAOYSA-M sodium 3-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)-1-fluoropropane-1-sulfonate Chemical compound O1C=2C(OCC1COCCC(S(=O)(=O)[O-])F)=CSC2.[Na+] OAJZFHFBPIVWMO-UHFFFAOYSA-M 0.000 description 1
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- JFKDGEWTJLDVDQ-UHFFFAOYSA-M sodium;3-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)propane-1-sulfonate Chemical compound [Na+].O1C(COCCCS(=O)(=O)[O-])COC2=CSC=C21 JFKDGEWTJLDVDQ-UHFFFAOYSA-M 0.000 description 1
- 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 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Description
本発明の重量平均分子量は、ゲル浸透クロマトグラフ法で分析値であり、プルラン換算の分子量である。
式(8)におけるMで表される金属イオンとしては、特に限定するものではないが、例えば、遷移金属イオン、貴金属イオン、非鉄金属イオン、アルカリ金属イオン(例えば、Liイオン、Naイオン、及びKイオン)、又はアルカリ土類金属イオン等が挙げられる。
上記一般式(5)及び(6)で表される繰り返し単位については、上記式(8)で表されるチオフェンモノマーの重合の際に、下記一般式(9)で表されるチオフェンモノマーが原料として共存する場合に生じるものである。すなわち、本発明のポリチオフェンを合成する際に、モノマー原料として下記式(9)で表されるチオフェンモノマーを20重量%以上含有しないことが導電性の観点から好ましい。
式(9)におけるMで表される金属イオンとしては、特に限定するものではないが、例えば、遷移金属イオン、貴金属イオン、非鉄金属イオン、アルカリ金属イオン(例えば、Liイオン、Naイオン、及びKイオン)、又はアルカリ土類金属イオン等が挙げられる。
鉄(II)塩としては、特に限定するものではないが、例えば、FeSO4・7H2Oが好ましい。鉄(III)塩としては、特に限定するものではないが、例えば、FeCl3、Fe2(SO4)3が好ましい。
本発明の導電性組成物における架橋剤としては、特に限定するものではないが、シラン化合物、ブロックイソシアネート化合物等が挙げられる。これらは2種類以上を併用して使用してもよい。
調製する際の雰囲気は、特に限定するものではないが、大気中でも、不活性ガス中でもよい。
本発明のポリチオフェンを0.7〜1.0重量%程度含む水溶液2.0gに50重量%濃度のN、N−ジイソプロピルアミンのメタノール溶液1.2gを加え一晩ゆっくりと撹拌した。濃縮後、65℃で真空乾燥して得られた固形分を1重量%濃度になるようにDMSOに溶解させた。その後、PVDFフィルター(0.45μm)に通液処理した液を下記ゲル浸透クロマトグラフィー分析条件で分析した。
・カラム:東ソー社製TSKgel α−M + guard Column α
・溶離液:DMSO / 10mM−LiBr
・流速:0.6mL / min
・検出:UV(335nm)
・温度:50℃
・注入量:1000ppm(20μL)
・標準:Pullulan
[自己ドープ型導電性高分子の導電率測定]
・フィルムの製膜
スライドガラス(26×70 mm)の真中にビニールテープを貼り,半分の面積(26×35 mm)にポリチオフェン水溶液(約1.0 重量%)を滴下する。赤外水分計(MOC−120H,島津製作所)を用いて空気中,120℃で加熱乾燥後,200℃30分熱処理することで導電性フィルムを作製した。
スライドガラスに貼ったビニールテープを剥がし,ガラス基板と導電性フィルムの段差を触針式段差計(D−100,KLA Tencor)で測定した。ガラス基板でベースライン補正した後,段差測定から導電性フィルムの膜厚を算出した。
導電性フィルムの電導度は,抵抗率計(ロレスタGP,MCP−T610型,三菱化学)を用いて測定した。4探針プローブ(PSPプローブ,三菱化学)をスタンドに固定し,フィルムを持ち上げることでプローブに接触させた。フィルムサイズ(26×35 mm)および膜厚を入力し,最低3サンプルの測定平均から電導度を算出した。
ポリチオフェン(A)[下記式(10)及び下記式(11)で表される繰り返し構造を含む重合体]の合成
120.0gの3−[(2、3−ジヒドロチエノ[3、4−b]−[1、4]ジオキシン−2−イル)メトキシ]−1−メチル−1−プロパンスルホン酸ナトリウム(99.5%LC純度)と62.5mLの硫酸を約1000mLの純水に溶解した。この混合液に60.55gの硫酸鉄七水和物を加え、さらに165.67gの過硫酸アンモニウムを含む水溶液滴下し、最後に全重量が1500gになるよう純水を加えて調製した。全重量に対するモノマーの仕込み濃度は8.0重量%であった。混合溶液を20℃で13時間、反応液全体が流動するように均一強撹拌させながら重合反応を行った。その後、反応溶液のイオン交換処理、脱塩等を行い、本発明の自己ドープ型ポリチオフェン水溶液(A)を得た。得られたポリチオフェン(A)の重量平均分子量(Mw)は53,167であった。また、保持時間の最も早いピークトップ(X)の分子量(Mp)が54,001であり、そのピーク強度と保持時間がその次に早いピークトップ(Y)のピーク強度の比(Xピーク強度/Yピーク強度)は1.09であった。ゲル浸透クロマトグラフィーチャートを図2に点線で示した。この水溶液をガラス基板上に成膜して得た塗膜の導電率は948S/cmであった。
ポリチオフェン(B)[上記式(10)及び上記式(11)で表される繰り返し構造を含む重合体]の合成.
500mLセパラブルフラスコに3−[(2,3−ジヒドロチエノ[3,4−b]−[1,4]ジオキシン−2−イル)メトキシ]−1−メチル−1−プロパンスルホン酸ナトリウム 10.0g(30mmol)と水 150gを加えた。溶解後、室温下、無水塩化鉄(III) 2.94g(18.1mmol)を加えて20分ゆるやかに攪拌した。その後、過硫酸ナトリウム 14.5g(60.4mmol)と水 100gからなる混合溶液を反応液温度が30℃以下を保持し、ゆるやかに撹拌しながら滴下した。重合液中のモノマー濃度は3.6重量%であった。室温で3時間ゆるやかに攪拌したのち、反応液を800gのアセトンに滴下させ黒色のNa型のポリマーを析出させた。ポリマーを濾過・真空乾燥することで、18.0gの3−[(2,3−ジヒドロチエノ[3,4−b]−[1,4]ジオキシン−2−イル)メトキシ]−1−メチル−1−プロパンスルホン酸ナトリウムの粗ポリマーを得た。
Claims (8)
- 重量平均分子量が3万以上であることを特徴とする請求項1に記載のポリチオフェン。
- 重量平均分子量が3万以上10万以下であることを特徴とする請求項1に記載のポリチオフェン。
- ゲル浸透クロマトグラムにおいて、2つ以上のピークを有し、尚且つ保持時間の最も早い第1のピークトップの分子量(Mp)が2.5万以上であることを特徴とする請求項1乃至請求項3のいずれか一項に記載のポリチオフェン。
- ゲル浸透クロマトグラムにおいて、2つ以上のピークを有し、尚且つ保持時間の最も早い第1のピークトップのピーク強度が、次に保持時間の早い第2のピークトップのピーク強度の0.5倍以上であることを特徴とする請求項1乃至請求項4のいずれか一項に記載のポリチオフェン。
- 導電率が300S/cm以上であることを特徴とする請求項1乃至請求項5のいずれか一項に記載のポリチオフェン。
- 請求項1乃至請求項7のいずれか一項に記載のポリチオフェンを含むことを特徴とする導電性組成物。
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