JP2009538973A - 導電性ポリマー組成物 - Google Patents
導電性ポリマー組成物 Download PDFInfo
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- JP2009538973A JP2009538973A JP2009513304A JP2009513304A JP2009538973A JP 2009538973 A JP2009538973 A JP 2009538973A JP 2009513304 A JP2009513304 A JP 2009513304A JP 2009513304 A JP2009513304 A JP 2009513304A JP 2009538973 A JP2009538973 A JP 2009538973A
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- Prior art keywords
- polymer
- acid
- fluorinated
- conductive polymer
- group
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- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 229920000642 polymer Polymers 0.000 claims abstract description 125
- 239000002253 acid Substances 0.000 claims abstract description 91
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 230000008859 change Effects 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- 239000006185 dispersion Substances 0.000 description 55
- -1 hydrogen ions Chemical class 0.000 description 48
- 125000000217 alkyl group Chemical group 0.000 description 40
- 229910052739 hydrogen Inorganic materials 0.000 description 36
- 239000002243 precursor Substances 0.000 description 36
- 239000001257 hydrogen Substances 0.000 description 31
- 229920001577 copolymer Polymers 0.000 description 30
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 230000002378 acidificating effect Effects 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 22
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 18
- 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 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 239000007800 oxidant agent Substances 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000003456 ion exchange resin Substances 0.000 description 14
- 229920003303 ion-exchange polymer Polymers 0.000 description 14
- 239000012528 membrane Substances 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 150000007942 carboxylates Chemical class 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- 230000001590 oxidative effect Effects 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 239000012510 hollow fiber Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000003729 cation exchange resin Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 229910052711 selenium Inorganic materials 0.000 description 10
- 239000011669 selenium Substances 0.000 description 10
- 229910052714 tellurium Inorganic materials 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 9
- 239000003957 anion exchange resin Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011148 porous material Substances 0.000 description 9
- 229910000077 silane Inorganic materials 0.000 description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 0 CC(C1=C(*2)C=CC1)=C2C=CI Chemical compound CC(C1=C(*2)C=CC1)=C2C=CI 0.000 description 7
- 125000004450 alkenylene group Chemical group 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 150000001768 cations Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 125000000542 sulfonic acid group Chemical group 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000005341 cation exchange Methods 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 125000004404 heteroalkyl group Chemical group 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 5
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 150000003673 urethanes Chemical class 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940123973 Oxygen scavenger Drugs 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 239000002482 conductive additive Substances 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- ZAHSNWXGKUBLHM-UHFFFAOYSA-N hydroperoxy(hydroxy)silane Chemical compound OO[SiH2]O ZAHSNWXGKUBLHM-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 125000004474 heteroalkylene group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002923 metal particle Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 150000005082 selenophenes Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000005087 tellurophenes Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- TUFKHKZLBZWCAW-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonyl fluoride Chemical compound C=COCC(C)OCCS(F)(=O)=O TUFKHKZLBZWCAW-UHFFFAOYSA-N 0.000 description 1
- RFJVDJWCXSPUBY-UHFFFAOYSA-N 2-(difluoromethylidene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)=C1OC(F)(F)C(F)(C(F)(F)F)O1 RFJVDJWCXSPUBY-UHFFFAOYSA-N 0.000 description 1
- JAIXJKPOHMMBKS-UHFFFAOYSA-N 2-chloro-1,1,3,4,4,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C(=C(F)F)Cl)F)(F)F)F)(F)F JAIXJKPOHMMBKS-UHFFFAOYSA-N 0.000 description 1
- SVQOKUWDNBOKFD-UHFFFAOYSA-N 2-ethenoxyethanesulfonyl fluoride Chemical compound FS(=O)(=O)CCOC=C SVQOKUWDNBOKFD-UHFFFAOYSA-N 0.000 description 1
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- 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
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- 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
- H01B1/122—Ionic conductors
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- 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
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- 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
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
Landscapes
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- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
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| PCT/US2007/012992 WO2007143124A1 (en) | 2006-06-01 | 2007-06-01 | Conductive polymer compositions |
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| US (1) | US8147719B2 (enExample) |
| EP (2) | EP2360200A1 (enExample) |
| JP (1) | JP2009538973A (enExample) |
| KR (1) | KR101398780B1 (enExample) |
| CN (1) | CN101454371B (enExample) |
| TW (1) | TW200849280A (enExample) |
| WO (1) | WO2007143124A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010174243A (ja) * | 2009-01-14 | 2010-08-12 | Air Products & Chemicals Inc | セレン含有導電性ポリマー及び導電性ポリマーの製造方法 |
| WO2014155421A1 (ja) * | 2013-03-29 | 2014-10-02 | パナソニック株式会社 | 導電性高分子微粒子分散体の製造方法およびその導電性高分子微粒子分散体を用いた電解コンデンサの製造方法 |
| JP2017019924A (ja) * | 2015-07-09 | 2017-01-26 | 信越化学工業株式会社 | 導電性高分子組成物、被覆品、及びパターン形成方法 |
| WO2019054191A1 (ja) * | 2017-09-14 | 2019-03-21 | 富士フイルム株式会社 | 固体電解質組成物、その製造方法、保存方法及びキット、固体電解質含有シート、その保存方法及びキット、並びに、全固体二次電池 |
| JP2023101147A (ja) * | 2022-01-07 | 2023-07-20 | 信越ポリマー株式会社 | 導電性高分子含有液の保存方法、導電性高分子含有液の製造方法、導電性積層体の製造方法、及び導電性複合体保存器 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080251768A1 (en) * | 2007-04-13 | 2008-10-16 | Che-Hsiung Hsu | Electrically conductive polymer compositions |
| US7901852B2 (en) * | 2008-02-29 | 2011-03-08 | Freescale Semiconductor, Inc. | Metrology of bilayer photoresist processes |
| EP2145916B1 (en) * | 2008-07-17 | 2013-06-19 | W.L.Gore & Associates Gmbh | Substrate coating comprising a complex of an ionic fluoropolymer and surface charged nanoparticles |
| JP2017521530A (ja) * | 2014-07-11 | 2017-08-03 | ローディア オペレーションズ | 導電性ポリマー複合体およびそのような複合体を含有する電子デバイス |
| CN104485480B (zh) * | 2014-12-09 | 2017-01-11 | 西南石油大学 | 自掺杂凝胶聚合物电解质及其制备方法 |
| CN110197869B (zh) * | 2019-04-29 | 2021-11-09 | 哈尔滨工业大学（深圳） | 一种聚离子液体基热电材料的制备方法 |
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- 2007-06-01 WO PCT/US2007/012992 patent/WO2007143124A1/en not_active Ceased
- 2007-06-01 EP EP11162701A patent/EP2360200A1/en not_active Withdrawn
- 2007-06-01 EP EP07777362A patent/EP2021395A1/en not_active Withdrawn
- 2007-06-01 CN CN2007800198434A patent/CN101454371B/zh not_active Expired - Fee Related
- 2007-06-01 US US11/756,985 patent/US8147719B2/en not_active Expired - Fee Related
- 2007-06-04 TW TW096120027A patent/TW200849280A/zh unknown
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010174243A (ja) * | 2009-01-14 | 2010-08-12 | Air Products & Chemicals Inc | セレン含有導電性ポリマー及び導電性ポリマーの製造方法 |
| WO2014155421A1 (ja) * | 2013-03-29 | 2014-10-02 | パナソニック株式会社 | 導電性高分子微粒子分散体の製造方法およびその導電性高分子微粒子分散体を用いた電解コンデンサの製造方法 |
| US9472348B2 (en) | 2013-03-29 | 2016-10-18 | Panasonic Intellectual Property Management Co., Ltd. | Method of producing conductive polymer particle dispersion, and method of producing electrolytic capacitor using said conductive polymer particle dispersion |
| JPWO2014155421A1 (ja) * | 2013-03-29 | 2017-02-16 | パナソニックＩｐマネジメント株式会社 | 導電性高分子微粒子分散体の製造方法およびその導電性高分子微粒子分散体を用いた電解コンデンサの製造方法 |
| JP2017019924A (ja) * | 2015-07-09 | 2017-01-26 | 信越化学工業株式会社 | 導電性高分子組成物、被覆品、及びパターン形成方法 |
| WO2019054191A1 (ja) * | 2017-09-14 | 2019-03-21 | 富士フイルム株式会社 | 固体電解質組成物、その製造方法、保存方法及びキット、固体電解質含有シート、その保存方法及びキット、並びに、全固体二次電池 |
| JPWO2019054191A1 (ja) * | 2017-09-14 | 2019-12-12 | 富士フイルム株式会社 | 固体電解質組成物、その製造方法、保存方法及びキット、固体電解質含有シート、その保存方法及びキット、並びに、全固体二次電池 |
| JP7035067B2 (ja) | 2017-09-14 | 2022-03-14 | 富士フイルム株式会社 | 固体電解質組成物、その製造方法、保存方法及びキット、固体電解質含有シート、その保存方法及びキット、並びに、全固体二次電池 |
| US11621436B2 (en) | 2017-09-14 | 2023-04-04 | Fujifilm Corporation | Solid electrolyte composition, manufacturing method thereof, storage method thereof, kit thereof, solid electrolyte-containing sheet, storage method thereof, kit thereof, and all-solid state secondary battery |
| JP2023101147A (ja) * | 2022-01-07 | 2023-07-20 | 信越ポリマー株式会社 | 導電性高分子含有液の保存方法、導電性高分子含有液の製造方法、導電性積層体の製造方法、及び導電性複合体保存器 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101398780B1 (ko) | 2014-06-18 |
| CN101454371A (zh) | 2009-06-10 |
| KR20090024235A (ko) | 2009-03-06 |
| US20080017834A1 (en) | 2008-01-24 |
| TW200849280A (en) | 2008-12-16 |
| EP2021395A1 (en) | 2009-02-11 |
| EP2360200A1 (en) | 2011-08-24 |
| US8147719B2 (en) | 2012-04-03 |
| WO2007143124A1 (en) | 2007-12-13 |
| CN101454371B (zh) | 2013-07-17 |
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