JP2007103558A - Solid electrolyte, electrolytic capacitor, and manufacturing method thereof - Google Patents
Solid electrolyte, electrolytic capacitor, and manufacturing method thereof Download PDFInfo
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- JP2007103558A JP2007103558A JP2005289728A JP2005289728A JP2007103558A JP 2007103558 A JP2007103558 A JP 2007103558A JP 2005289728 A JP2005289728 A JP 2005289728A JP 2005289728 A JP2005289728 A JP 2005289728A JP 2007103558 A JP2007103558 A JP 2007103558A
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- Prior art keywords
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- acid
- solid electrolyte
- compound
- conductive polymer
- Prior art date
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- 239000003990 capacitor Substances 0.000 title claims abstract description 52
- 239000007784 solid electrolyte Substances 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- -1 amide compound Chemical class 0.000 claims description 76
- 229920000447 polyanionic polymer Polymers 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 25
- 230000001590 oxidative effect Effects 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 description 42
- 239000000178 monomer Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 35
- 238000000034 method Methods 0.000 description 29
- 239000002253 acid Substances 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 22
- 150000001450 anions Chemical group 0.000 description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 16
- 125000000129 anionic group Chemical group 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 229920000123 polythiophene Polymers 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 125000005641 methacryl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- LNIMMWYNSBZESE-UHFFFAOYSA-N 2-Ethyl-3-methylpyrazine, 9CI Chemical compound CCC1=NC=CN=C1C LNIMMWYNSBZESE-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 4
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- 229910052758 niobium Inorganic materials 0.000 description 4
- 239000010955 niobium Substances 0.000 description 4
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 239000003792 electrolyte Substances 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- VXXGMHKGORIRTK-UHFFFAOYSA-N 3-methyl-3-propylpyrrolidine-2,5-dione Chemical compound CCCC1(C)CC(=O)NC1=O VXXGMHKGORIRTK-UHFFFAOYSA-N 0.000 description 2
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- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- MYOWBHNETUSQPA-UHFFFAOYSA-N tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCS(O)(=O)=O MYOWBHNETUSQPA-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- MPKQTNAUFAZSIJ-UHFFFAOYSA-N thiophene-3,4-diol Chemical compound OC1=CSC=C1O MPKQTNAUFAZSIJ-UHFFFAOYSA-N 0.000 description 1
- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
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- 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
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- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Conductive Materials (AREA)
Abstract
Description
本発明は、ポリチオフェン系のπ共役系導電性高分子を含む固体電解質に関する。また、π共役系導電性高分子を含む固体電解質層を陰極に備えた電解コンデンサ並びにその製造方法に関する。 The present invention relates to a solid electrolyte containing a polythiophene-based π-conjugated conductive polymer. The present invention also relates to an electrolytic capacitor having a solid electrolyte layer containing a π-conjugated conductive polymer on a cathode and a method for manufacturing the same.
近年、電子機器のデジタル化に伴い、これに用いられるコンデンサとしては高周波領域におけるインピーダンスが低いものが要求されてきている。従来から、この要求に対応すべく、アルミニウム、タンタル、ニオブなどの弁金属の酸化皮膜を誘電体とし、この表面にポリピロール、ポリチオフェンなどのπ共役系導電性高分子を形成して陰極とした、所謂、機能性コンデンサが使用されている。
機能性コンデンサの具体的構造としては、特許文献1に示されるように、弁金属多孔体を陽極とし、この表面に形成した誘電体酸化皮膜上に、π共役系導電性高分子を含む固体電解質層、カーボン層、銀層を積層した陰極材料を持つものが一般的である。
In recent years, with the digitization of electronic devices, capacitors having low impedance in the high frequency region have been required as capacitors used therefor. Conventionally, in order to meet this demand, an oxide film of a valve metal such as aluminum, tantalum, or niobium is used as a dielectric, and a π-conjugated conductive polymer such as polypyrrole or polythiophene is formed on this surface as a cathode. So-called functional capacitors are used.
As a specific structure of the functional capacitor, as disclosed in Patent Document 1, a solid electrolyte containing a π-conjugated conductive polymer on a dielectric oxide film formed on the surface of a porous valve metal body as an anode is disclosed. A material having a cathode material in which a layer, a carbon layer, and a silver layer are laminated is generally used.
π共役導電性高分子を含む固体電解質層は、多孔質状の誘電体酸化皮膜の内部にまで入り込んで、誘電体酸化皮膜との接触面積を大きくして、高容量を引き出すと共に、誘電体酸化皮膜の欠損部を修復して漏れ電流によるリークを防止する役割を果たす。このような役割を果たすためには、等価直列抵抗(ESR)が低いことが求められ、ESRを低くするためには、導電性を高くする必要がある。また、固体電解質層としては、使用環境下において信頼性を保つための安定性(例えば耐熱性)が求められる。 The solid electrolyte layer containing the π-conjugated conductive polymer penetrates into the porous dielectric oxide film, increases the contact area with the dielectric oxide film, draws out a high capacity, and oxidizes the dielectric. It plays the role of repairing the missing part of the film and preventing leakage due to leakage current. In order to play such a role, the equivalent series resistance (ESR) is required to be low, and in order to reduce the ESR, it is necessary to increase the conductivity. Further, the solid electrolyte layer is required to have stability (for example, heat resistance) for maintaining reliability in the use environment.
π共役系導電性高分子は不溶不融の固体物質であり、その形成法としては、通常、電解重合法と化学酸化重合法が採られる。例えば、特許文献2には、弁金属多孔体表面にマンガン酸化物からなる導電層を形成した後に、その導電層を電極としてπ共役系導電性高分子の前駆体モノマーを電解重合することが記載されている。また、特許文献3,4には、化学酸化重合法によりπ共役系導電性高分子を得る方法が開示されている。 The π-conjugated conductive polymer is an insoluble and infusible solid substance, and as its formation method, an electrolytic polymerization method and a chemical oxidative polymerization method are usually employed. For example, Patent Document 2 describes that after a conductive layer made of manganese oxide is formed on the surface of a valve metal porous body, a precursor monomer of a π-conjugated conductive polymer is electropolymerized using the conductive layer as an electrode. Has been. Patent Documents 3 and 4 disclose a method of obtaining a π-conjugated conductive polymer by a chemical oxidative polymerization method.
電解重合法はマンガン酸化物のような導電体をあらかじめ形成する必要があることから工程が煩雑になりやすく、主流は化学酸化重合法に移行してきている。化学酸化重合法においては、モノマーの反応性が工程の所要時間、設計を決める重要な要素となっているため、π共役系導電性高分子の前駆体モノマーとしては、反応性が高く、短時間で重合が完了し、副生成物の少ないものが求められる。その要求を満たすものとして、ピロール、3,4−エチレンジオキシチオフェンなどが挙げられる。
しかしながら、近年、電解コンデンサの使用される用途が広がり、使用環境も次第に苛酷な条件となってきており、導電性及び耐熱性のより一層の向上が求められている。
In the electrolytic polymerization method, a conductor such as manganese oxide needs to be formed in advance, so that the process tends to be complicated, and the mainstream has shifted to the chemical oxidation polymerization method. In chemical oxidative polymerization, monomer reactivity is an important factor in determining process time and design. Therefore, precursor monomers for π-conjugated conductive polymers are highly reactive and require a short time. Thus, the polymerization is completed, and a product with few by-products is required. Examples of those that satisfy the requirement include pyrrole and 3,4-ethylenedioxythiophene.
However, in recent years, the use of electrolytic capacitors has expanded, and the usage environment has become increasingly severe, and further improvements in conductivity and heat resistance are required.
また、電解重合、化学酸化重合をコンデンサ製造工程内で行うことは、煩雑であり、困難である。そのため、スルホ基、カルボキシル基等を持つポリアニオンを共存させながらアニリンを重合して、ポリアニリンの水溶液を調製し、そのポリアニオン水溶液を塗布、乾燥することが提案されている(特許文献5参照)。しかしながら、特許文献5の方法では、ポリアニオン水溶液の多孔質内部への浸透性が低く、満足のいく性能は得られなかった。
本発明は、導電性及び耐熱性に優れた固体電解質を提供することを目的とする。さらには、ESRが低く、しかも苛酷な条件に耐えうる電解コンデンサ並びにその製造方法を提供することを目的とする。 An object of this invention is to provide the solid electrolyte excellent in electroconductivity and heat resistance. It is another object of the present invention to provide an electrolytic capacitor having a low ESR and capable of withstanding severe conditions, and a method for manufacturing the same.
本発明の固体電解質は、化学式(1)で表されるπ共役系導電性高分子を含有することを特徴とする。
(化学式(1)におけるR1、R3は、それぞれ独立して、水素原子または炭素数1〜12のアルキル基であり、R2は置換されていてもよい炭素数1〜8のアルキレン基である。また、nは10以上の整数である。)
The solid electrolyte of the present invention contains a π-conjugated conductive polymer represented by the chemical formula (1).
(R 1 and R 3 in chemical formula (1) are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and R 2 is an optionally substituted alkylene group having 1 to 8 carbon atoms. And n is an integer of 10 or more.)
本発明の固体電解質においては、(a)アミド化合物、(b)窒素含有芳香環化合物、(c)2個以上のヒドロキシル基を有するヒドロキシル基含有芳香族性化合物、(d)グリシジル基を有する化合物、(e)アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種とヒドロキシル基とを有する化合物、から選ばれる1種または2種以上の導電性向上成分をさらに含有することが好ましい。
また、本発明の固体電解質においては、ポリアニオンをさらに含有することが好ましい。
本発明の電解コンデンサは、弁金属の多孔質体からなる陽極と、該陽極の表面が酸化されて形成された誘電体層と、該誘電体層上に形成され、上述した固体電解質からなる固体電解質層を備える陰極とを有することを特徴とする。
本発明の電解コンデンサの製造方法は、弁金属の多孔質体からなる陽極と該陽極の表面が酸化されて形成された酸化被膜の誘電体層とを有するコンデンサ中間体の誘電体層側表面に、導電性高分子溶液を塗布して固体電解質層を形成する電解コンデンサの製造方法であって、前記導電性高分子溶液が、上述した固体電解質を溶媒中に溶解又は分散した液であることを特徴とする。
In the solid electrolyte of the present invention, (a) an amide compound, (b) a nitrogen-containing aromatic ring compound, (c) a hydroxyl group-containing aromatic compound having two or more hydroxyl groups, and (d) a compound having a glycidyl group (E) one or more conductivity improving components selected from compounds having one kind selected from an allyl group, vinyl ether group, methacryl group, acrylic group, methacrylamide group, and acrylamide group and a hydroxyl group. Furthermore, it is preferable to contain.
The solid electrolyte of the present invention preferably further contains a polyanion.
The electrolytic capacitor of the present invention includes an anode made of a porous body of valve metal, a dielectric layer formed by oxidizing the surface of the anode, and a solid made of the solid electrolyte formed on the dielectric layer. And a cathode including an electrolyte layer.
The method for producing an electrolytic capacitor of the present invention includes a capacitor intermediate body having an anode made of a porous body of valve metal and an oxide film dielectric layer formed by oxidizing the surface of the anode. A method of manufacturing an electrolytic capacitor in which a conductive polymer solution is applied to form a solid electrolyte layer, wherein the conductive polymer solution is a solution obtained by dissolving or dispersing the solid electrolyte in a solvent. Features.
本発明の固体電解質は、導電性及び耐熱性に優れる。
本発明の電解コンデンサは、ESRが低く、容量を高くできる上に、漏れ電流を小さくでき、しかも苛酷な条件に耐えうる。
本発明の電解コンデンサの製造方法によれば、ESRが低く、容量を高くできる上に、漏れ電流を小さくでき、しかも苛酷な条件に耐えうる電解コンデンサの製造方法を提供する。
The solid electrolyte of the present invention is excellent in conductivity and heat resistance.
The electrolytic capacitor of the present invention has a low ESR, a high capacity, a small leakage current, and can withstand severe conditions.
According to the method for manufacturing an electrolytic capacitor of the present invention, there is provided a method for manufacturing an electrolytic capacitor that has a low ESR and a high capacity, can reduce a leakage current, and can withstand severe conditions.
(固体電解質)
本発明の固体電解質は、上記π共役系導電性高分子を含有し、必要に応じて、ポリアニオン、導電性向上成分、ドーパントなどを含有するものである。固体電解質中のπ共役系導電性高分子の含有量は、10〜100質量%であることが好ましい。
(Solid electrolyte)
The solid electrolyte of the present invention contains the π-conjugated conductive polymer, and contains a polyanion, a conductivity improving component, a dopant, and the like as necessary. The content of the π-conjugated conductive polymer in the solid electrolyte is preferably 10 to 100% by mass.
[π共役系導電性高分子]
本発明におけるπ共役系導電性高分子は、化学式(1)で表されるポリチオフェンである。このようなポリチオフェンは、化学式(2)で表されるモノマーの単独重合もしくは他のモノマーとの共重合により得られる。
なお、化学式(1),(2)におけるR1、R3は、それぞれ独立して、水素原子または炭素数1〜12のアルキル基であり、R2は置換されていてもよい炭素数1〜8のアルキレン基である。また、nは10以上の整数である。
[Π-conjugated conductive polymer]
The π-conjugated conductive polymer in the present invention is polythiophene represented by the chemical formula (1). Such a polythiophene is obtained by homopolymerization of a monomer represented by the chemical formula (2) or copolymerization with another monomer.
In the chemical formulas (1) and (2), R 1 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and R 2 is an optionally substituted carbon atom having 1 to 1 carbon atoms. 8 is an alkylene group. N is an integer of 10 or more.
π共役系導電性高分子が共重合体である場合の他のモノマーとしては、例えば、ピロール類及びその誘導体、チオフェン類及びその誘導体、アニリン類及びその誘導体等が挙げられる。
具体例としては、ピロール、N−メチルピロール、3−メチルピロール、3−エチルピロール、3−n−プロピルピロール、3−ブチルピロール、3−オクチルピロール、3−デシルピロール、3−ドデシルピロール、3,4−ジメチルピロール、3,4−ジブチルピロール、3−カルボキシピロール、3−メチル−4−カルボキシピロール、3−メチル−4−カルボキシエチルピロール、3−メチル−4−カルボキシブチルピロール、3−ヒドロキシピロール、3−メトキシピロール、3−エトキシピロール、3−ブトキシピロール、3−ヘキシルオキシピロール、3−メチル−4−ヘキシルオキシピロール、3−メチル−4−ヘキシルオキシピロール、チオフェン、3−メチルチオフェン、3−エチルチオフェン、3−プロピルチオフェン、3−ブチルチオフェン、3−ヘキシルチオフェン、3−ヘプチルチオフェン、3−オクチルチオフェン、3−デシルチオフェン、3−ドデシルチオフェン、3−オクタデシルチオフェン、3−ブロモチオフェン、3−クロロチオフェン、3−ヨードチオフェン、3−シアノチオフェン、3−フェニルチオフェン、3,4−ジメチルチオフェン、3,4−ジブチルチオフェン、3−ヒドロキシチオフェン、3−メトキシチオフェン、3−エトキシチオフェン、3−ブトキシチオフェン、3−ヘキシルオキシチオフェン、3−ヘプチルオキシチオフェン、3−オクチルオキシチオフェン、3−デシルオキシチオフェン、3−ドデシルオキシチオフェン、3−オクタデシルオキシチオフェン、3,4−ジヒドロキシチオフェン、3,4−ジメトキシチオフェン、3,4−ジエトキシチオフェン、3,4−ジプロポキシチオフェン、3,4−ジブトキシチオフェン、3,4−ジヘキシルオキシチオフェン、3,4−ジヘプチルオキシチオフェン、3,4−ジオクチルオキシチオフェン、3,4−ジデシルオキシチオフェン、3,4−ジドデシルオキシチオフェン、3,4−エチレンジオキシチオフェン、3,4−プロピレンジオキシチオフェン、3,4−ブテンジオキシチオフェン、3−メチル−4−メトキシチオフェン、3−メチル−4−エトキシチオフェン、3−カルボキシチオフェン、3−メチル−4−カルボキシチオフェン、3−メチル−4−カルボキシエチルチオフェン、3−メチル−4−カルボキシブチルチオフェン、アニリン、2−メチルアニリン、3−イソブチルアニリン、2−アニリンスルホン酸、3−アニリンスルホン酸等が挙げられる。
Examples of other monomers when the π-conjugated conductive polymer is a copolymer include pyrroles and derivatives thereof, thiophenes and derivatives thereof, anilines and derivatives thereof, and the like.
Specific examples include pyrrole, N-methylpyrrole, 3-methylpyrrole, 3-ethylpyrrole, 3-n-propylpyrrole, 3-butylpyrrole, 3-octylpyrrole, 3-decylpyrrole, 3-dodecylpyrrole, 3 , 4-dimethylpyrrole, 3,4-dibutylpyrrole, 3-carboxypyrrole, 3-methyl-4-carboxypyrrole, 3-methyl-4-carboxyethylpyrrole, 3-methyl-4-carboxybutylpyrrole, 3-hydroxy Pyrrole, 3-methoxypyrrole, 3-ethoxypyrrole, 3-butoxypyrrole, 3-hexyloxypyrrole, 3-methyl-4-hexyloxypyrrole, 3-methyl-4-hexyloxypyrrole, thiophene, 3-methylthiophene, 3-ethylthiophene, 3-propylthiophene 3-butylthiophene, 3-hexylthiophene, 3-heptylthiophene, 3-octylthiophene, 3-decylthiophene, 3-dodecylthiophene, 3-octadecylthiophene, 3-bromothiophene, 3-chlorothiophene, 3-iodothiophene , 3-cyanothiophene, 3-phenylthiophene, 3,4-dimethylthiophene, 3,4-dibutylthiophene, 3-hydroxythiophene, 3-methoxythiophene, 3-ethoxythiophene, 3-butoxythiophene, 3-hexyloxythiophene , 3-heptyloxythiophene, 3-octyloxythiophene, 3-decyloxythiophene, 3-dodecyloxythiophene, 3-octadecyloxythiophene, 3,4-dihydroxythiophene, 3,4-dimeth Cithiophene, 3,4-diethoxythiophene, 3,4-dipropoxythiophene, 3,4-dibutoxythiophene, 3,4-dihexyloxythiophene, 3,4-diheptyloxythiophene, 3,4-dioctyloxy Thiophene, 3,4-didecyloxythiophene, 3,4-didodecyloxythiophene, 3,4-ethylenedioxythiophene, 3,4-propylenedioxythiophene, 3,4-butenedioxythiophene, 3-methyl -4-methoxythiophene, 3-methyl-4-ethoxythiophene, 3-carboxythiophene, 3-methyl-4-carboxythiophene, 3-methyl-4-carboxyethylthiophene, 3-methyl-4-carboxybutylthiophene, aniline , 2-methylaniline, 3-isobutylanily , 2-aniline sulfonic acid, 3-aniline sulfonic acid and the like.
π共役系導電性高分子が、化学式(2)で表されるモノマー単位と上記他のモノマー単位とからなる共重合体である場合、他のモノマー単位は10〜90モル%であることが好ましい。 When the π-conjugated conductive polymer is a copolymer composed of the monomer unit represented by the chemical formula (2) and the other monomer unit, the other monomer unit is preferably 10 to 90 mol%. .
上記π共役系導電性高分子は、酸化剤又は酸化触媒存在下、化学式(2)で表されるモノマーと、必要に応じて、上記他のモノマーとを化学酸化重合することにより得られる。
ここで、酸化剤、酸化触媒としては、前記モノマーを酸化させてπ共役系導電性高分子を得ることができるものであればよく、例えば、ぺルオキソ二硫酸アンモニウム(過硫酸アンモニウム)、ぺルオキソ二硫酸ナトリウム(過硫酸ナトリウム)、ぺルオキソ二硫酸カリウム(過硫酸カリウム)等のぺルオキソ二硫酸塩、塩化第二鉄、硫酸第二鉄、硝酸第二鉄、塩化第二銅等の遷移金属化合物、三フッ化ホウ素、塩化アルミニウムなどの金属ハロゲン化合物、酸化銀、酸化セシウム等の金属酸化物、過酸化水素、オゾン等の過酸化物、過酸化ベンゾイル等の有機過酸化物、酸素等が挙げられる。
The π-conjugated conductive polymer can be obtained by chemical oxidative polymerization of the monomer represented by the chemical formula (2) and, if necessary, the other monomer in the presence of an oxidizing agent or an oxidation catalyst.
Here, the oxidizing agent and the oxidation catalyst are not particularly limited as long as they can oxidize the monomer to obtain a π-conjugated conductive polymer, such as ammonium peroxodisulfate (ammonium persulfate), peroxodisulfuric acid. Transition metal compounds such as sodium (sodium persulfate), peroxodisulfate such as potassium peroxodisulfate (potassium persulfate), ferric chloride, ferric sulfate, ferric nitrate, cupric chloride, Examples include metal halogen compounds such as boron trifluoride and aluminum chloride, metal oxides such as silver oxide and cesium oxide, peroxides such as hydrogen peroxide and ozone, organic peroxides such as benzoyl peroxide, and oxygen. .
π共役系導電性高分子を化学酸化重合により製造する際には、溶媒中で行うことが好ましい。溶媒としては特に限定されず、例えば、メタノール、エタノール、イソプロパノール(IPA)などのアルコール系溶媒、N−メチルピロリドン(NMP)、ジメチルアセトアミド(DMAc)、ジメチルホルムアミド(DMF)などのアミド系溶媒、メチルエチルケトン(MEK)、アセトン、シクロヘキサノンなどのケトン系溶媒、酢酸エチル、酢酸ブチルのようなエステル系溶媒、トルエン、キシレン、水など、これらの単独もしくは混合溶媒が用いられる。中でも、環境への負荷が小さいことから、水やアルコール系溶媒の使用が好ましい。 When the π-conjugated conductive polymer is produced by chemical oxidative polymerization, it is preferably performed in a solvent. The solvent is not particularly limited, and examples thereof include alcohol solvents such as methanol, ethanol and isopropanol (IPA), amide solvents such as N-methylpyrrolidone (NMP), dimethylacetamide (DMAc) and dimethylformamide (DMF), and methyl ethyl ketone. (MEK), ketone solvents such as acetone and cyclohexanone, ester solvents such as ethyl acetate and butyl acetate, toluene, xylene, water and the like alone or in combination. Among them, the use of water or an alcohol-based solvent is preferable because the load on the environment is small.
化学式(1)で表されるπ共役系導電性高分子は、反応性の高いモノマー(化学式(2))から合成されるため、短時間で得られる上に、副生成物が少ない。また、上記π共役系導電性高分子は、導電性及び耐熱性に優れる。 Since the π-conjugated conductive polymer represented by the chemical formula (1) is synthesized from a highly reactive monomer (chemical formula (2)), it is obtained in a short time and has few by-products. The π-conjugated conductive polymer is excellent in conductivity and heat resistance.
[ポリアニオン]
本発明の固体電解質は、導電性及び耐熱性がより高くなることから、ポリアニオンを含有することが好ましい。
ポリアニオンは、置換若しくは未置換のポリアルキレン、置換若しくは未置換のポリアルケニレン、置換若しくは未置換のポリイミド、置換若しくは未置換のポリアミド、置換若しくは未置換のポリエステル及びこれらの共重合体であって、アニオン基を有する構成単位からなるものまたは、アニオン基を有する構成単位とアニオン基を有さない構成単位とからなるものである。
このポリアニオンのアニオン基は、π共役系導電性高分子に対するドーパントとして機能し、π共役系導電性高分子の導電性と耐熱性をより向上させる。
[Polyanion]
The solid electrolyte of the present invention preferably contains a polyanion because it has higher conductivity and heat resistance.
The polyanion is a substituted or unsubstituted polyalkylene, a substituted or unsubstituted polyalkenylene, a substituted or unsubstituted polyimide, a substituted or unsubstituted polyamide, a substituted or unsubstituted polyester, and a copolymer thereof. It consists of a structural unit having a group or a structural unit having an anionic group and a structural unit not having an anionic group.
The anion group of this polyanion functions as a dopant for the π-conjugated conductive polymer, and further improves the conductivity and heat resistance of the π-conjugated conductive polymer.
ポリアルキレンとは、主鎖がメチレンの繰り返しで構成されているポリマーである。ポリアルキレンとしては、例えば、ポリエチレン、ポリプロピレン、ポリブテン、ポリペンテン、ポリヘキセン、ポリビニルアルコール、ポリビニルフェノール、ポリ3,3,3−トリフルオロプロピレン、ポリアクリロニトリル、ポリアクリレート、ポリスチレン等が挙げられる。 A polyalkylene is a polymer whose main chain is composed of repeating methylenes. Examples of the polyalkylene include polyethylene, polypropylene, polybutene, polypentene, polyhexene, polyvinyl alcohol, polyvinylphenol, poly3,3,3-trifluoropropylene, polyacrylonitrile, polyacrylate, polystyrene, and the like.
ポリアルケニレンとは、主鎖に不飽和結合(ビニル基)が1個以上含まれる構成単位からなるポリマーである。ポリアルケニレンの具体例としては、プロペニレン、1−メチルプロペニレン、1−ブチルプロペニレン、1−デシルプロペニレン、1−シアノプロペニレン、1−フェニルプロペニレン、1−ヒドロキシプロペニレン、1−ブテニレン、1−メチル−1−ブテニレン、1−エチル−1−ブテニレン、1−オクチル−1−ブテニレン、1−ペンタデシル−1−ブテニレン、2−メチル−1−ブテニレン、2−エチル−1−ブテニレン、2−ブチル−1−ブテニレン、2−ヘキシル−1−ブテニレン、2−オクチル−1−ブテニレン、2−デシル−1−ブテニレン、2−ドデシル−1−ブテニレン、2−フェニル−1−ブテニレン、2−ブテニレン、1−メチル−2−ブテニレン、1−エチル−2−ブテニレン、1−オクチル−2−ブテニレン、1−ペンタデシル−2−ブテニレン、2−メチル−2−ブテニレン、2−エチル−2−ブテニレン、2−ブチル−2−ブテニレン、2−ヘキシル−2−ブテニレン、2−オクチル−2−ブテニレン、2−デシル−2−ブテニレン、2−ドデシル−2−ブテニレン、2−フェニル−2−ブテニレン、2−プロピレンフェニル−2−ブテニレン、3−メチル−2−ブテニレン、3−エチル−2−ブテニレン、3−ブチル−2−ブテニレン、3−ヘキシル−2−ブテニレン、3−オクチル−2−ブテニレン、3−デシル−2−ブテニレン、3−ドデシル−2−ブテニレン、3−フェニル−2−ブテニレン、3−プロピレンフェニル−2−ブテニレン、2−ペンテニレン、4−プロピル−2−ペンテニレン、4−ブチル−2−ペンテニレン、4−ヘキシル−2−ペンテニレン、4−シアノ−2−ペンテニレン、3−メチル−2−ペンテニレン、4−エチル−2−ペンテニレン、3−フェニル−2−ペンテニレン、4−ヒドロキシ−2−ペンテニレン、ヘキセニレン等から選ばれる1種以上の構成単位を含む重合体が挙げられる。
これらの中でも、不飽和結合とπ共役系導電性高分子との相互作用があること、置換若しくは未置換のブタジエンを出発物質として合成しやすいことから、置換若しくは未置換のブテニレンが好ましい。
Polyalkenylene is a polymer composed of structural units containing one or more unsaturated bonds (vinyl groups) in the main chain. Specific examples of polyalkenylene include propenylene, 1-methylpropenylene, 1-butylpropenylene, 1-decylpropenylene, 1-cyanopropenylene, 1-phenylpropenylene, 1-hydroxypropenylene, 1-butenylene, 1-methyl-1-butenylene, 1-ethyl-1-butenylene, 1-octyl-1-butenylene, 1-pentadecyl-1-butenylene, 2-methyl-1-butenylene, 2-ethyl-1-butenylene, 2- Butyl-1-butenylene, 2-hexyl-1-butenylene, 2-octyl-1-butenylene, 2-decyl-1-butenylene, 2-dodecyl-1-butenylene, 2-phenyl-1-butenylene, 2-butenylene, 1-methyl-2-butenylene, 1-ethyl-2-butenylene, 1-octyl-2-butenylene 1-pentadecyl-2-butenylene, 2-methyl-2-butenylene, 2-ethyl-2-butenylene, 2-butyl-2-butenylene, 2-hexyl-2-butenylene, 2-octyl-2-butenylene, 2- Decyl-2-butenylene, 2-dodecyl-2-butenylene, 2-phenyl-2-butenylene, 2-propylenephenyl-2-butenylene, 3-methyl-2-butenylene, 3-ethyl-2-butenylene, 3-butyl 2-butenylene, 3-hexyl-2-butenylene, 3-octyl-2-butenylene, 3-decyl-2-butenylene, 3-dodecyl-2-butenylene, 3-phenyl-2-butenylene, 3-propylenephenyl- 2-butenylene, 2-pentenylene, 4-propyl-2-pentenylene, 4-butyl-2-pentenylene, 4-he Selected from sil-2-pentenylene, 4-cyano-2-pentenylene, 3-methyl-2-pentenylene, 4-ethyl-2-pentenylene, 3-phenyl-2-pentenylene, 4-hydroxy-2-pentenylene, hexenylene, etc. And a polymer containing one or more structural units.
Among these, substituted or unsubstituted butenylene is preferable because of the interaction between the unsaturated bond and the π-conjugated conductive polymer and the ease of synthesis using substituted or unsubstituted butadiene as a starting material.
ポリイミドとしては、ピロメリット酸二無水物、ビフェニルテトラカルボン酸二無水物、ベンゾフェノンテトラカルボン酸二無水物、2,2’,3,3’−テトラカルボキシジフェニルエーテル二無水物、2,2’−[4,4’−ジ(ジカルボキシフェニルオキシ)フェニル]プロパン二無水物等の無水物とオキシジアミン、パラフェニレンジアミン、メタフェニレンジアミン、ベンゾフェノンジアミン等のジアミンとからのポリイミドが挙げられる。
ポリアミドとしては、ポリアミド6、ポリアミド6,6、ポリアミド6,10等が挙げられる。
ポリエステルとしては、ポリエチレンテレフタレート、ポリブチレンテレフタレート等が挙げられる。
As polyimide, pyromellitic dianhydride, biphenyltetracarboxylic dianhydride, benzophenonetetracarboxylic dianhydride, 2,2 ′, 3,3′-tetracarboxydiphenyl ether dianhydride, 2,2 ′-[ Examples include polyimides from anhydrides such as 4,4′-di (dicarboxyphenyloxy) phenyl] propane dianhydride and diamines such as oxydiamine, paraphenylenediamine, metaphenylenediamine, and benzophenonediamine.
Examples of the polyamide include polyamide 6, polyamide 6,6,
Examples of the polyester include polyethylene terephthalate and polybutylene terephthalate.
ポリアニオンが置換基を有する場合、その置換基としては、アルキル基、ヒドロキシル基、アミノ基、カルボキシル基、シアノ基、フェニル基、フェノール基、エステル基、アルコキシル基等が挙げられる。溶媒への溶解性、耐熱性及び樹脂への相溶性等を考慮すると、アルキル基、ヒドロキシル基、フェノール基、エステル基が好ましい。
アルキル基は、極性溶媒又は非極性溶媒への溶解性及び分散性、樹脂への相溶性及び分散性等を高くすることができ、ヒドロキシル基は、他の水素原子等との水素結合を形成しやすくでき、有機溶媒への溶解性、樹脂への相溶性、分散性、接着性を高くすることができる。また、シアノ基及びヒドロキシフェニル基は、極性樹脂への相溶性、溶解性を高くすることができ、しかも、耐熱性も高くすることができる。
上記置換基の中では、アルキル基、ヒドロキシル基、エステル基、シアノ基が好ましい。
When the polyanion has a substituent, examples of the substituent include an alkyl group, a hydroxyl group, an amino group, a carboxyl group, a cyano group, a phenyl group, a phenol group, an ester group, and an alkoxyl group. In view of solubility in a solvent, heat resistance, compatibility with a resin, and the like, an alkyl group, a hydroxyl group, a phenol group, and an ester group are preferable.
Alkyl groups can increase solubility and dispersibility in polar or nonpolar solvents, compatibility and dispersibility in resins, etc., and hydroxyl groups form hydrogen bonds with other hydrogen atoms and the like. This makes it easy to increase solubility in organic solvents, compatibility with resins, dispersibility, and adhesion. In addition, the cyano group and the hydroxyphenyl group can increase the compatibility and solubility in the polar resin, and can also increase the heat resistance.
Among the above substituents, an alkyl group, a hydroxyl group, an ester group, and a cyano group are preferable.
前記アルキル基としては、メチル、エチル、プロピル、ブチル、イソブチル、t−ブチル、ペンチル、ヘキシル、オクチル、デシル、ドデシル等の鎖状アルキル基、シクロプロピル、シクロペンチル、シクロヘキシル等のシクロアルキル基が挙げられる。有機溶剤への溶解性、樹脂への分散性、立体障害等を考慮すると、炭素数1〜12のアルキル基がより好ましい。
前記ヒドロキシル基としては、ポリアニオンの主鎖に直接結合したヒドロキシル基又は他の官能基を介在して結合したヒドロキシル基が挙げられる。他の官能基としては、炭素数1〜7のアルキル基、炭素数2〜7のアルケニル基、アミド基、イミド基等が挙げられる。ヒドロキシル基はこれらの官能基の末端又は中に置換されている。これらの中では樹脂への相溶及び有機溶剤への溶解性から、主鎖に結合した炭素数1〜6のアルキル基の末端に結合したヒドロキシル基がより好ましい。
前記アミノ基としては、ポリアニオンの主鎖に直接結合したアミノ基又は他の官能基を介在して結合したアミノ基が挙げられる。他の官能基としては、炭素数1〜7のアルキル基、炭素数2〜7のアルケニル基、アミド基、イミド基等が挙げられる。アミノ基はこれらの官能基の末端又は中に置換されている。
前記フェノール基としては、ポリアニオンの主鎖に直接結合したフェノール基又は他の官能基を介在して結合したフェノール基が挙げられる。他の官能基としては、炭素数1〜7のアルキル基、炭素数2〜7のアルケニル基、アミド基、イミド基等が挙げられる。フェノール基はこれらの官能基の末端又は中に置換されている。
前記エステル基としては、ポリアニオンの主鎖に直接結合したアルキル系エステル基、芳香族系エステル基、他の官能基を介在してなるアルキル系エステル基又は芳香族系エステル基が挙げられる。
シアノ基としては、ポリアニオンの主鎖に直接結合したシアノ基、ポリアニオンの主鎖に結合した炭素数1〜7のアルキル基の末端に結合したシアノ基、ポリアニオンの主鎖に結合した炭素数2〜7のアルケニル基の末端に結合したシアノ基等を挙げることができる。
Examples of the alkyl group include chain alkyl groups such as methyl, ethyl, propyl, butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, decyl, and dodecyl, and cycloalkyl groups such as cyclopropyl, cyclopentyl, and cyclohexyl. . In consideration of solubility in an organic solvent, dispersibility in a resin, steric hindrance, and the like, an alkyl group having 1 to 12 carbon atoms is more preferable.
Examples of the hydroxyl group include a hydroxyl group directly bonded to the main chain of the polyanion or a hydroxyl group bonded via another functional group. Examples of other functional groups include an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an amide group, and an imide group. Hydroxyl groups are substituted at the ends or in these functional groups. In these, the hydroxyl group couple | bonded with the terminal of the C1-C6 alkyl group couple | bonded with the principal chain is more preferable from the compatibility to resin and the solubility to an organic solvent.
Examples of the amino group include an amino group directly bonded to the main chain of the polyanion or an amino group bonded via another functional group. Examples of other functional groups include an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an amide group, and an imide group. The amino group is substituted at the end or in these functional groups.
Examples of the phenol group include a phenol group directly bonded to the main chain of the polyanion or a phenol group bonded via another functional group. Examples of other functional groups include an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an amide group, and an imide group. The phenol group is substituted at the end or in these functional groups.
Examples of the ester group include an alkyl ester group directly bonded to the main chain of the polyanion, an aromatic ester group, and an alkyl ester group or an aromatic ester group having another functional group interposed therebetween.
The cyano group includes a cyano group directly bonded to the main chain of the polyanion, a cyano group bonded to the terminal of the alkyl group having 1 to 7 carbon atoms bonded to the main chain of the polyanion, and 2 to 2 carbon atoms bonded to the main chain of the polyanion. And a cyano group bonded to the terminal of 7 alkenyl group.
ポリアニオンのアニオン基としては、π共役系導電性高分子への化学酸化ドープが起こりうる官能基であればよいが、中でも、製造の容易さ及び安定性の観点からは、一置換硫酸エステル基、一置換リン酸エステル基、リン酸基、カルボキシル基、スルホ基等が好ましい。さらに、官能基のπ共役系導電性高分子へのドープ効果の観点より、スルホ基、一置換硫酸エステル基、カルボキシル基がより好ましい。 The anion group of the polyanion may be a functional group capable of undergoing chemical oxidation doping to the π-conjugated conductive polymer. Among them, from the viewpoint of ease of production and stability, a monosubstituted sulfate group, A monosubstituted phosphate group, a phosphate group, a carboxyl group, a sulfo group and the like are preferable. Furthermore, from the viewpoint of the doping effect of the functional group on the π-conjugated conductive polymer, a sulfo group, a monosubstituted sulfate group, and a carboxyl group are more preferable.
ポリアニオンの具体例としては、ポリビニルスルホン酸、ポリスチレンスルホン酸、ポリアリルスルホン酸、ポリアクリルスルホン酸、ポリメタクリルスルホン酸、ポリ(2−アクリルアミド−2−メチルプロパンスルホン酸)、ポリイソプレンスルホン酸、ポリビニルカルボン酸、ポリスチレンカルボン酸、ポリアリルカルボン酸、ポリアクリルカルボン酸、ポリメタクリルカルボン酸、ポリ(2−アクリルアミド−2−メチルプロパンカルボン酸)、ポリイソプレンカルボン酸、ポリアクリル酸等が挙げられる。これらの単独重合体であってもよいし、2種以上の共重合体であってもよい。
これらのうち、ポリアクリルスルホン酸、ポリメタクリルスルホン酸が好ましい。ポリアクリルスルホン酸、ポリメタクリルスルホン酸は、熱エネルギーを吸収して自ら分解することにより、π共役系導電性高分子成分の熱分解が緩和されるため、耐熱性、耐環境性により優れる。
Specific examples of polyanions include polyvinyl sulfonic acid, polystyrene sulfonic acid, polyallyl sulfonic acid, polyacryl sulfonic acid, polymethacryl sulfonic acid, poly (2-acrylamido-2-methylpropane sulfonic acid), polyisoprene sulfonic acid, polyvinyl Examples thereof include carboxylic acid, polystyrene carboxylic acid, polyallyl carboxylic acid, polyacryl carboxylic acid, polymethacryl carboxylic acid, poly (2-acrylamido-2-methylpropane carboxylic acid), polyisoprene carboxylic acid, polyacrylic acid and the like. These homopolymers may be sufficient and 2 or more types of copolymers may be sufficient.
Of these, polyacrylsulfonic acid and polymethacrylsulfonic acid are preferred. Polyacrylsulfonic acid and polymethacrylsulfonic acid are superior in heat resistance and environmental resistance because thermal decomposition of the π-conjugated conductive polymer component is relaxed by absorbing thermal energy and decomposing by itself.
ポリアニオンの重合度は、モノマー単位が10〜100,000個の範囲であることが好ましく、溶媒溶解性及び導電性の点からは、50〜10,000個の範囲がより好ましい。 The degree of polymerization of the polyanion is preferably in the range of 10 to 100,000 monomer units, and more preferably in the range of 50 to 10,000 from the viewpoint of solvent solubility and conductivity.
ポリアニオンの製造方法としては、例えば、酸を用いてアニオン基を有さないポリマーにアニオン基を直接導入する方法、アニオン基を有さないポリマーをスルホ化剤によりスルホン酸化する方法、アニオン基含有重合性モノマーの重合により製造する方法が挙げられる。
アニオン基含有重合性モノマーの重合により製造する方法は、溶媒中、アニオン基含有重合性モノマーを、酸化剤及び/又は重合触媒の存在下で、酸化重合又はラジカル重合によって製造する方法が挙げられる。具体的には、所定量のアニオン基含有重合性モノマーを溶媒に溶解させ、これを一定温度に保ち、それに予め溶媒に所定量の酸化剤及び/又は重合触媒を溶解した溶液を添加し、所定時間で反応させる。その反応により得られたポリマーは溶媒によって一定の濃度に調整される。この製造方法において、アニオン基含有重合性モノマーにアニオン基を有さない重合性モノマーを共重合させてもよい。
アニオン基含有重合性モノマーの重合に際して使用する酸化剤及び酸化触媒、溶媒は、π共役系導電性高分子を形成する前駆体モノマーを重合する際に使用するものと同様である。
得られたポリマーがポリアニオン塩である場合には、ポリアニオン酸に変質させることが好ましい。アニオン酸に変質させる方法としては、イオン交換樹脂を用いたイオン交換法、透析法、限外ろ過法等が挙げられ、これらの中でも、作業が容易な点から限外ろ過法が好ましい。
Examples of methods for producing polyanions include a method of directly introducing an anionic group into a polymer having no anionic group using an acid, a method of sulfonating a polymer having no anionic group with a sulfonating agent, and anionic group-containing polymerization. And a method of production by polymerization of a functional monomer.
Examples of the method for producing an anion group-containing polymerizable monomer by polymerization include a method for producing an anion group-containing polymerizable monomer in a solvent by oxidative polymerization or radical polymerization in the presence of an oxidizing agent and / or a polymerization catalyst. Specifically, a predetermined amount of the anionic group-containing polymerizable monomer is dissolved in a solvent, kept at a constant temperature, and a solution in which a predetermined amount of an oxidizing agent and / or a polymerization catalyst is dissolved in the solvent is added to the predetermined amount. React with time. The polymer obtained by the reaction is adjusted to a certain concentration by the solvent. In this production method, an anionic group-containing polymerizable monomer may be copolymerized with a polymerizable monomer having no anionic group.
The oxidizing agent, oxidation catalyst, and solvent used in the polymerization of the anionic group-containing polymerizable monomer are the same as those used in the polymerization of the precursor monomer that forms the π-conjugated conductive polymer.
When the obtained polymer is a polyanionic salt, it is preferably transformed into a polyanionic acid. Examples of the method for converting to an anionic acid include an ion exchange method using an ion exchange resin, a dialysis method, an ultrafiltration method, and the like. Among these, the ultrafiltration method is preferable from the viewpoint of easy work.
アニオン基含有重合性モノマーは、モノマーの一部が一置換硫酸エステル基、カルボキシル基、スルホ基等で置換されたものであり、例えば、置換若しくは未置換のエチレンスルホン酸化合物、置換若しくは未置換のスチレンスルホン酸化合物、置換若しくは未置換のアクリレートスルホン酸化合物、置換若しくは未置換のメタクリレートスルホン酸化合物、置換若しくは未置換のアクリルアミドスルホン酸化合物、置換若しくは未置換のシクロビニレンスルホン酸化合物、置換若しくは未置換のブタジエンスルホン酸化合物、置換若しくは未置換のビニル芳香族スルホン酸化合物が挙げられる。
具体的には、ビニルスルホン酸及びその塩類、アリルスルホン酸及びその塩類、メタリルスルホン酸及びその塩類、スチレンスルホン酸、メタリルオキシベンゼンスルホン酸及びその塩類、アリルオキシベンゼンスルホン酸及びその塩類、α−メチルスチレンスルホン酸及びその塩類、アクリルアミド−t−ブチルスルホン酸及びその塩類、2−アクリルアミド−2−メチルプロパンスルホン酸及びその塩類、シクロブテン−3−スルホン酸及びその塩類、イソプレンスルホン酸及びその塩類、1,3−ブタジエン−1−スルホン酸及びその塩類、1−メチル−1,3−ブタジエン−2−スルホン酸及びその塩類、1−メチル−1,3−ブタジエン−4−スルホン酸及びその塩類、アクリル酸エチルスルホン酸(CH2CH-COO-(CH2)2-SO3H)及びその塩類、アクリル酸プロピルスルホン酸(CH2CH-COO-(CH2)3-SO3H)及びその塩類、アクリル酸−t−ブチルスルホン酸(CH2CH-COO-C(CH3)2CH2-SO3H)及びその塩類、アクリル酸−n−ブチルスルホン酸(CH2CH-COO-(CH2)4-SO3H)及びその塩類、アリル酸エチルスルホン酸(CH2CHCH2-COO-(CH2)2-SO3H)及びその塩類、アリル酸−t−ブチルスルホン酸(CH2CHCH2-COO-C(CH3)2CH2-SO3H)及びその塩類、4−ペンテン酸エチルスルホン酸(CH2CH(CH2)2-COO-(CH2)2-SO3H)及びその塩類、4−ペンテン酸プロピルスルホン酸(CH2CH(CH2)2-COO-(CH2)3-SO3H)及びその塩類、4−ペンテン酸−n−ブチルスルホン酸(CH2CH(CH2)2-COO-(CH2)4-SO3H)及びその塩類、4−ペンテン酸−t−ブチルスルホン酸(CH2CH(CH2)2-COO-C(CH3)2CH2-SO3H)及びその塩類、4−ペンテン酸フェニレンスルホン酸(CH2CH(CH2)2-COO-C6H4-SO3H)及びその塩類、4−ペンテン酸ナフタレンスルホン酸(CH2CH(CH2)2-COO-C10H8-SO3H)及びその塩類、メタクリル酸エチルスルホン酸(CH2C(CH3)-COO-(CH2)2-SO3H)及びその塩類、メタクリル酸プロピルスルホン酸(CH2C(CH3)-COO-(CH2)3-SO3H)及びその塩類、メタクリル酸−t−ブチルスルホン酸(CH2C(CH3)-COO-C(CH3)2CH2-SO3H)及びその塩類、メタクリル酸−n−ブチルスルホン酸(CH2C(CH3)-COO-(CH2)4-SO3H)及びその塩類、メタクリル酸フェニレンスルホン酸(CH2C(CH3)-COO-C6H4-SO3H)及びその塩類、メタクリル酸ナフタレンスルホン酸(CH2C(CH3)-COO-C10H8-SO3H)及びその塩類、ポリビニルカルボン酸、ポリスチレンカルボン酸、ポリアリルカルボン酸、ポリアクリルカルボン酸、ポリメタクリルカルボン酸、ポリ−2−アクリルアミド−2−メチルプロパンカルボン酸、ポリイソプレンカルボン酸、ポリアクリル酸等が挙げられる。また、これらを2種以上含む共重合体であってもよい。
The anionic group-containing polymerizable monomer is one in which a part of the monomer is substituted with a monosubstituted sulfate group, a carboxyl group, a sulfo group, etc., for example, a substituted or unsubstituted ethylene sulfonic acid compound, a substituted or unsubstituted Styrene sulfonic acid compound, substituted or unsubstituted acrylate sulfonic acid compound, substituted or unsubstituted methacrylate sulfonic acid compound, substituted or unsubstituted acrylamide sulfonic acid compound, substituted or unsubstituted cyclovinylene sulfonic acid compound, substituted or unsubstituted And a substituted or unsubstituted vinyl aromatic sulfonic acid compound.
Specifically, vinyl sulfonic acid and salts thereof, allyl sulfonic acid and salts thereof, methallyl sulfonic acid and salts thereof, styrene sulfonic acid, methallyloxybenzene sulfonic acid and salts thereof, allyloxybenzene sulfonic acid and salts thereof, α-methylstyrenesulfonic acid and its salts, acrylamide-t-butylsulfonic acid and its salts, 2-acrylamido-2-methylpropanesulfonic acid and its salts, cyclobutene-3-sulfonic acid and its salts, isoprenesulfonic acid and its Salts, 1,3-butadiene-1-sulfonic acid and its salts, 1-methyl-1,3-butadiene-2-sulfonic acid and its salts, 1-methyl-1,3-butadiene-4-sulfonic acid and its salts, ethyl acrylate sulfonic acid (CH 2 CH-COO- (CH 2 2 -SO 3 H) and its salts, acrylic acid propyl sulfonic acid (CH 2 CH-COO- (CH 2) 3 -SO 3 H) and its salts, acrylic acid -t- butyl sulfonic acid (CH 2 CH-COO -C (CH 3) 2 CH 2 -SO 3 H) and its salts, acrylic acid -n- butyl sulfonic acid (CH 2 CH-COO- (CH 2) 4 -SO 3 H) and salts thereof, ethyl allyl acid sulfonic acid (CH 2 CHCH 2 -COO- (CH 2) 2 -SO 3 H) and its salts, allyl acid -t- butyl sulfonic acid (CH 2 CHCH 2 -COO-C (CH 3) 2 CH 2 -SO 3 H) and salts thereof, 4-pentenoic acid ethyl sulfonic acid (CH 2 CH (CH 2) 2 -COO- (CH 2) 2 -SO 3 H) and salts thereof, 4-pentenoic acid propyl sulfonic acid (CH 2 CH (CH 2 ) 2 —COO— (CH 2 ) 3 -SO 3 H) and salts thereof, 4-pentenoic acid-n-butylsulfonic acid (CH 2 CH (CH 2 ) 2 —COO— (CH 2 ) 4 —SO 3 H) and salts thereof, 4-pentene Acid-t-butyl sulfonic acid (CH 2 CH (CH 2 ) 2 —COO—C (CH 3 ) 2 CH 2 —SO 3 H) and its salts, 4-pentenoic acid phenylene sulfonic acid (CH 2 CH (CH 2 2 ) -COO—C 6 H 4 —SO 3 H) and salts thereof, 4-pentenoic acid naphthalenesulfonic acid (CH 2 CH (CH 2 ) 2 —COO—C 10 H 8 —SO 3 H) and salts thereof, Ethyl methacrylate sulfonic acid (CH 2 C (CH 3 ) —COO— (CH 2 ) 2 —SO 3 H) and salts thereof, propyl methacrylate methacrylate (CH 2 C (CH 3 ) —COO— (CH 2 ) 3 -SO 3 H) and its salts, methacrylic acid-t-butylsulfate Acid (CH 2 C (CH 3) -COO-C (CH 3) 2 CH 2 -SO 3 H) and its salts, methacrylic acid -n- butyl sulfonic acid (CH 2 C (CH 3) -COO- ( CH 2 ) 4 —SO 3 H) and salts thereof, phenylene sulfonic acid methacrylate (CH 2 C (CH 3 ) —COO—C 6 H 4 —SO 3 H) and salts thereof, naphthalene sulfonic acid methacrylate (CH 2) C (CH 3 ) —COO—C 10 H 8 —SO 3 H) and salts thereof, polyvinyl carboxylic acid, polystyrene carboxylic acid, polyallyl carboxylic acid, polyacryl carboxylic acid, polymethacryl carboxylic acid, poly-2-acrylamide— Examples include 2-methylpropanecarboxylic acid, polyisoprene carboxylic acid, polyacrylic acid and the like. Moreover, the copolymer containing 2 or more types of these may be sufficient.
アニオン基を有さない重合性モノマーとしては、エチレン、プロぺン、1−ブテン、2−ブテン、1−ペンテン、2−ペンテン、1−ヘキセン、2−ヘキセン、スチレン、p−メチルスチレン、p−エチルスチレン、p−ブチルスチレン、2,4,6−トリメチルスチレン、p−メトキシスチレン、α−メチルスチレン、2−ビニルナフタレン、6−メチル−2−ビニルナフタレン、1−ビニルイミダゾール、ビニルピリジン、ビニルアセテート、アクリルアルデヒド、アクリルニトリル、N−ビニル−2−ピロリドン、N−ビニルアセトアミド、N−ビニルホルムアミド、N−ビニルイミダゾ−ル、アクリルアミド、N,N−ジメチルアクリルアミド、アクリル酸、アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸n−ブチル、アクリル酸イソブチル、アクリル酸t−ブチル、アクリル酸イソオクチル、アクリル酸イソノニルブチル、アクリル酸ラウリル、アクリル酸アリル、アクリル酸ステアリル、アクリル酸イソボニル、アクリル酸シクロヘキシル、アクリル酸ベンジル、アクリル酸エチルカルビトール、アクリル酸フェノキシエチル、アクリル酸ヒドロキシエチル、アクリル酸メトキシエチル、アクリル酸エトキシエチル、アクリル酸メトキシブチル、メタクリル酸、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸n−ブチル、メタクリル酸イソブチル、メタクリル酸t−ブチル、メタクリル酸2−エチルヘキシル、メタクリル酸ラウリル、メタクリル酸トリデシル、メタクリル酸ステアリル、メタクリル酸シクロヘキシル、メタクリル酸ベンジル、メタクリル酸2−ヒドロキシエチル、メタクリル酸2−ヒドロキシプロピル、アクリロイルモルホリン、ビニルアミン、N,N−ジメチルビニルアミン、N,N−ジエチルビニルアミン、N,N−ジブチルビニルアミン、N,N−ジ−t−ブチルビニルアミン、N,N−ジフェニルビニルアミン、N−ビニルカルバゾール、ビニルアルコール、塩化ビニル、フッ化ビニル、メチルビニルエーテル、エチルビニルエーテル、シクロプロペン、シクロブテン、シクロペンテン、シクロヘキセン、シクロヘプテン、シクロオクテン、2−メチルシクロヘキセン、ビニルフェノール、1,3−ブタジエン、1−メチル−1,3−ブタジエン、2−メチル−1,3−ブタジエン、1,4−ジメチル−1,3−ブタジエン、1,2−ジメチル−1,3−ブタジエン、1,3−ジメチル−1,3−ブタジエン、1−オクチル−1,3−ブタジエン、2−オクチル−1,3−ブタジエン、1−フェニル−1,3−ブタジエン、2−フェニル−1,3−ブタジエン、1−ヒドロキシ−1,3−ブタジエン、2−ヒドロキシ−1,3−ブタジエン等が挙げられる。
これらアニオン基を有さない重合性モノマーを共重合することで溶媒溶解性をコントロールすることができる。
Examples of the polymerizable monomer having no anionic group include ethylene, propene, 1-butene, 2-butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, styrene, p-methylstyrene, p. -Ethylstyrene, p-butylstyrene, 2,4,6-trimethylstyrene, p-methoxystyrene, α-methylstyrene, 2-vinylnaphthalene, 6-methyl-2-vinylnaphthalene, 1-vinylimidazole, vinylpyridine, Vinyl acetate, acrylaldehyde, acrylonitrile, N-vinyl-2-pyrrolidone, N-vinylacetamide, N-vinylformamide, N-vinylimidazole, acrylamide, N, N-dimethylacrylamide, acrylic acid, methyl acrylate, Ethyl acrylate, propyl acrylate, acrylic acid -Butyl, isobutyl acrylate, t-butyl acrylate, isooctyl acrylate, isononyl butyl acrylate, lauryl acrylate, allyl acrylate, stearyl acrylate, isobornyl acrylate, cyclohexyl acrylate, benzyl acrylate, ethyl acrylate Carbitol, phenoxyethyl acrylate, hydroxyethyl acrylate, methoxyethyl acrylate, ethoxyethyl acrylate, methoxybutyl acrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, methacryl T-butyl acid, 2-ethylhexyl methacrylate, lauryl methacrylate, tridecyl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, methacrylic acid Benzyl, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, acryloylmorpholine, vinylamine, N, N-dimethylvinylamine, N, N-diethylvinylamine, N, N-dibutylvinylamine, N, N-di -T-butylvinylamine, N, N-diphenylvinylamine, N-vinylcarbazole, vinyl alcohol, vinyl chloride, vinyl fluoride, methyl vinyl ether, ethyl vinyl ether, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, 2-methylcyclohexene, vinylphenol, 1,3-butadiene, 1-methyl-1,3-butadiene, 2-methyl-1,3-butadiene, 1,4-dimethyl-1,3-butadiene, 1,2- Dimethyl , 3-butadiene, 1,3-dimethyl-1,3-butadiene, 1-octyl-1,3-butadiene, 2-octyl-1,3-butadiene, 1-phenyl-1,3-butadiene, 2-phenyl -1,3-butadiene, 1-hydroxy-1,3-butadiene, 2-hydroxy-1,3-butadiene and the like.
Solvent solubility can be controlled by copolymerizing these polymerizable monomers having no anionic group.
ポリアニオンの含有量は、π共役系導電性高分子1モルに対して0.1〜10モルの範囲であることが好ましく、1〜7モルの範囲であることがより好ましい。ポリアニオンの含有量が0.1モルより少なくなると、π共役系導電性高分子へのドーピング効果が弱くなる傾向にあり、導電性が不足することがある。また、ポリアニオンの含有量が10モルより多くなると、π共役系導電性高分子の含有割合が少なくなり、やはり充分な導電性が得られにくい。 The content of the polyanion is preferably in the range of 0.1 to 10 mol, and more preferably in the range of 1 to 7 mol, with respect to 1 mol of the π-conjugated conductive polymer. When the polyanion content is less than 0.1 mol, the doping effect on the π-conjugated conductive polymer tends to be weak, and the conductivity may be insufficient. On the other hand, when the polyanion content is more than 10 mol, the content ratio of the π-conjugated conductive polymer decreases, and it is difficult to obtain sufficient conductivity.
[導電性向上成分]
固体電解質は、導電性をより高める上に、多孔体への浸透性及び耐熱性がより向上することから、(a)アミド化合物、(b)窒素含有芳香環化合物、(c)2個以上のヒドロキシル基を有するヒドロキシル基含有芳香族性化合物、(d)グリシジル基を有する化合物、(e)e)アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種とヒドロキシル基とを有する化合物、から選ばれる1種または2種以上の導電性向上成分をさらに含有することが好ましい。
[Conductivity improving component]
Since the solid electrolyte further enhances the conductivity, and further improves the permeability and heat resistance to the porous body, (a) an amide compound, (b) a nitrogen-containing aromatic ring compound, (c) two or more A hydroxyl group-containing aromatic compound having a hydroxyl group, (d) a compound having a glycidyl group, (e) e) one kind selected from an allyl group, a vinyl ether group, a methacryl group, an acrylic group, a methacrylamide group, and an acrylamide group; It is preferable to further contain one or more conductivity enhancing components selected from compounds having a hydroxyl group.
<(a)アミド化合物>
アミド化合物の具体例としては、アセトアミド、マロンアミド、スクシンアミド、マレアミド、フマルアミド、ベンズアミド、ナフトアミド、フタルアミド、イソフタルアミド、テレフタルアミド、ニコチンアミド、イソニコチンアミド、2−フルアミド、ホルムアミド、プロピオンアミド、プロピオルアミド、ブチルアミド、イソブチルアミド、メタクリルアミド、パルミトアミド、ステアリルアミド、オレアミド、オキサミド、グルタルアミド、アジプアミド、シンナムアミド、グルコールアミド、ラクトアミド、グリセルアミド、タルタルアミド、シトルアミド、グリオキシルアミド、プルブアミド、アセトアセトアミド、ベンジルアミド、アントラニルアミド、エチレンジアミンテトラアセトアミド、ジアセトアミド、トリアセトアミド、ジベンズアミド、トリベンズアミド、ローダニン、尿素、1−アセチル−2−チオ尿素、ビウレット、ブチル尿素、ジブチル尿素、1,3−ジメチル尿素、1,3−ジエチル尿素及びこれらの誘導体等が挙げられる。
アミド化合物の分子量は46〜5,000であることが好ましく、46〜1,000であることがより好ましく、46〜500であることが特に好ましい。
<(A) Amide compound>
Specific examples of the amide compound include acetamide, malonamide, succinamide, maleamide, fumaramide, benzamide, naphthamide, phthalamide, isophthalamide, terephthalamide, nicotinamide, isonicotinamide, 2-fluamide, formamide, propionamide, propionamide, Butyramide, Isobutylamide, Methacrylamide, Palmitoamide, Stearylamide, Oleamide, Oxamide, Glutaramide, Adipamide, Cinnamamide, Glucolamide, Lactamide, Glyceramide, Tartaramide, Citrulamide, Glyoxylamide, Plubuamide, Acetoacetamide, Benzylamide, Anthranilamide , Ethylenediaminetetraacetamide, diacetamide, triacetoa And dibenzamide, tribenzamide, rhodanine, urea, 1-acetyl-2-thiourea, biuret, butylurea, dibutylurea, 1,3-dimethylurea, 1,3-diethylurea, and derivatives thereof. .
The molecular weight of the amide compound is preferably 46 to 5,000, more preferably 46 to 1,000, and particularly preferably 46 to 500.
アミド化合物としては、導電性がより高くなることから、イミド結合を有する単分子化合物(以下、イミド化合物という。)が好ましい。
イミド化合物の具体例としては、1,8−ナフチルイミド、フタルイミド、3−ニトロフタルイミド、4−ニトロフタルイミド、3−アミノフタルイミド、4−アミノフタルイミド、シクロヘキサン−1,2−ジカルボキシイミド、アラントイン、ヒダントイン、バルビツル酸、アロキサン、グルタルイミド、スクシンイミド、5−ブチルヒダントイン酸、5,5−ジメチルヒダントイン、1−メチルヒダントイン、1,5,5−トリメチルヒダントイン、5−ヒダントイン酢酸、N−ヒドロキシ−5−ノルボルネン−2,3−ジカルボキシイミド、グルタルイミド、セミカルバジド、α,α−ジメチル−6−メチルスクシンイミド、ビス[2−(スクシンイミドオキシカルボニルオキシ)エチル]スルホン、α−メチル−α−プロピルスクシンイミド、シクロヘキシルイミド、1,3−ジプロピレン尿素、マレイミド、N−メチルマレイミド、N−エチルマレイミド、N−ヒドロキシマレイミド、1,4−ビスマレイミドブタン、1,6−ビスマレイミドヘキサン、1,8−ビスマレイミドオクタン、N−カルボキシヘプチルマレイミドなどが挙げられる。
As the amide compound, a monomolecular compound having an imide bond (hereinafter referred to as an imide compound) is preferable because of higher conductivity.
Specific examples of the imide compound include 1,8-naphthylimide, phthalimide, 3-nitrophthalimide, 4-nitrophthalimide, 3-aminophthalimide, 4-aminophthalimide, cyclohexane-1,2-dicarboximide, allantoin and hydantoin. , Barbituric acid, alloxan, glutarimide, succinimide, 5-butylhydantoic acid, 5,5-dimethylhydantoin, 1-methylhydantoin, 1,5,5-trimethylhydantoin, 5-hydantoin acetic acid, N-hydroxy-5-norbornene -2,3-dicarboximide, glutarimide, semicarbazide, α, α-dimethyl-6-methylsuccinimide, bis [2- (succinimidooxycarbonyloxy) ethyl] sulfone, α-methyl-α-propyl succin Imide, cyclohexylimide, 1,3-dipropyleneurea, maleimide, N-methylmaleimide, N-ethylmaleimide, N-hydroxymaleimide, 1,4-bismaleimidebutane, 1,6-bismaleimide hexane, 1,8- Examples thereof include bismaleimide octane and N-carboxyheptylmaleimide.
イミド化合物は両末端の官能基の種類によって、脂肪族イミド、芳香族イミド等の分類もされるが、その骨格より、フタルイミド及びフタルイミド誘導体、スクシンイミド及びスクシンイミド誘導体、ベンズイミド及びベンズイミド誘導体、マレイミド及びマレイミド誘導体、ナフタルイミド及びナフタルイミド誘導体などが挙げられる。溶解性の観点からは、脂肪族イミドが好ましい。 Imide compounds are also classified as aliphatic imides, aromatic imides, etc., depending on the type of functional groups at both ends, but from the skeleton, phthalimide and phthalimide derivatives, succinimide and succinimide derivatives, benzimide and benzimide derivatives, maleimide and maleimide derivatives , Naphthalimide and naphthalimide derivatives. From the viewpoint of solubility, an aliphatic imide is preferred.
さらに、脂肪族イミド化合物は、分子内の炭素間に不飽和結合を有する飽和脂肪族イミド化合物と、分子内の炭素間に不飽和結合を有する不飽和脂肪族イミド化合物とに分類される。
飽和脂肪族イミド化合物は、R1−CO−NH−CO−R2で表される化合物であり、R1,R2の両方が飽和炭化水素である化合物である。具体的には、シクロヘキサン−1,2−ジカルボキシイミド、アラントイン、ヒダントイン、バルビツル酸、アロキサン、グルタルイミド、スクシンイミド、5−ブチルヒダントイン酸、5,5−ジメチルヒダントイン、1−メチルヒダントイン、1,5,5−トリメチルヒダントイン、5−ヒダントイン酢酸、N−ヒドロキシ−5−ノルボルネン−2,3−ジカルボキシイミド、グルタルイミド、セミカルバジド、α,α−ジメチル−6−メチルスクシンイミド、ビス[2−(スクシンイミドオキシカルボニルオキシ)エチル]スルホン、α−メチル−α−プロピルスクシンイミド、シクロヘキシルイミドなどが挙げられる。
不飽和脂肪族イミド化合物は、R1−CO−NH−CO−R2で表される化合物であり、R1,R2の一方又は両方が1つ以上の不飽和結合である化合物である。具体例は、1,3−ジプロピレン尿素、マレイミド、N−メチルマレイミド、N−エチルマレイミド、N−ヒドロキシマレイミド、1,4−ビスマレイミドブタン、1,6−ビスマレイミドヘキサン、1,8−ビスマレイミドオクタン、N−カルボキシヘプチルマレイミドなどが挙げられる。
Furthermore, the aliphatic imide compound is classified into a saturated aliphatic imide compound having an unsaturated bond between carbons in the molecule and an unsaturated aliphatic imide compound having an unsaturated bond between carbons in the molecule.
The saturated aliphatic imide compound is a compound represented by R 1 —CO—NH—CO—R 2 , and is a compound in which both R 1 and R 2 are saturated hydrocarbons. Specifically, cyclohexane-1,2-dicarboximide, allantoin, hydantoin, barbituric acid, alloxan, glutarimide, succinimide, 5-butylhydantoic acid, 5,5-dimethylhydantoin, 1-methylhydantoin, 1,5 , 5-trimethylhydantoin, 5-hydantoin acetic acid, N-hydroxy-5-norbornene-2,3-dicarboximide, glutarimide, semicarbazide, α, α-dimethyl-6-methylsuccinimide, bis [2- (succinimideoxy) Carbonyloxy) ethyl] sulfone, α-methyl-α-propylsuccinimide, cyclohexylimide and the like.
The unsaturated aliphatic imide compound is a compound represented by R 1 —CO—NH—CO—R 2 , and one or both of R 1 and R 2 are one or more unsaturated bonds. Specific examples are 1,3-dipropylene urea, maleimide, N-methylmaleimide, N-ethylmaleimide, N-hydroxymaleimide, 1,4-bismaleimide butane, 1,6-bismaleimide hexane, 1,8-bis. Maleimide octane, N-carboxyheptylmaleimide and the like can be mentioned.
イミド化合物の分子量は60〜5,000であることが好ましく、70〜1,000であることがより好ましく、80〜500であることが特に好ましい。 The molecular weight of the imide compound is preferably 60 to 5,000, more preferably 70 to 1,000, and particularly preferably 80 to 500.
アミド化合物及びイミド化合物の含有量は、π共役系導電性高分子のドープに寄与していないポリアニオンのアニオン基に対して0.1〜100モル当量であることが好ましく、0.5〜50モル当量であることがより好ましく、1.0〜20モル当量であることが特に好ましい。アミド化合物及びイミド化合物の添加量が前記下限値未満であると、アミド化合物及びイミド化合物添加による効果が低くなるため好ましくない。また、前記上限値を超えると、π共役系導電性高分子濃度の低下に起因する導電性の低下が起こるため好ましくない。 The content of the amide compound and the imide compound is preferably 0.1 to 100 mole equivalents relative to the anion group of the polyanion not contributing to the doping of the π-conjugated conductive polymer, and 0.5 to 50 moles More preferably, it is equivalent to 1.0 to 20 molar equivalents. If the addition amount of the amide compound and the imide compound is less than the lower limit, the effect of the addition of the amide compound and the imide compound is lowered, which is not preferable. Moreover, when the said upper limit is exceeded, since the electroconductive fall resulting from the fall of (pi) conjugated system conductive polymer concentration will occur, it is unpreferable.
<(b)窒素含有芳香環化合物>
窒素含有芳香環化合物としては、窒素が芳香環に含まれる化合物であれば、芳香環に置換基が導入されていなくとも、置換されていても好適に使用することができる。また、芳香環にさらに芳香環が縮合された多環系芳香環も好適に使用することができる。前記置換基としては、アルキル基、ヒドロキシル基、カルボキシル基、シアノ基、フェニル基、フェノール基、エステル基、アルコキシル基、カルボニル基等が挙げられる。
<(B) Nitrogen-containing aromatic ring compound>
As the nitrogen-containing aromatic ring compound, any compound in which nitrogen is contained in the aromatic ring can be suitably used even if the aromatic ring is not substituted or substituted. A polycyclic aromatic ring in which an aromatic ring is further condensed to an aromatic ring can also be used suitably. Examples of the substituent include an alkyl group, a hydroxyl group, a carboxyl group, a cyano group, a phenyl group, a phenol group, an ester group, an alkoxyl group, and a carbonyl group.
窒素含有芳香環化合物としては、例えば、一つの窒素原子を含有するピリジン及びその誘導体、二つの窒素原子を含有するイミダゾール及びその誘導体、ピリミジン及びその誘導体、ピラジン及びその誘導体、三つの窒素原子を含有するトリアジン及びその誘導体等が挙げられる。溶媒溶解性等の観点から、ピリジン及びその誘導体、イミダゾール及びその誘導体、ピリミジン及びその誘導体が好ましい。 Examples of nitrogen-containing aromatic ring compounds include pyridine containing one nitrogen atom and derivatives thereof, imidazole containing two nitrogen atoms and derivatives thereof, pyrimidine and derivatives thereof, pyrazine and derivatives thereof, and containing three nitrogen atoms. And triazine and derivatives thereof. From the viewpoint of solvent solubility, pyridine and its derivatives, imidazole and its derivatives, and pyrimidine and its derivatives are preferable.
一つの窒素原子を含有するピリジン及びその誘導体の具体的な例としては、ピリジン、2−メチルピリジン、3−メチルピリジン、4−メチルピリジン、4−エチルピリジン、2,4−ジメチルピリジン、2,4,6−トリメチルピリジン、3−シアノ−5−メチルピリジン、2−ピリジンカルボン酸、6−メチル−2−ピリジンカルボン酸、2,6−ピリジン-ジカルボン酸、4−ピリジンカルボキシアルデヒド、4−アミノピリジン、2,3−ジアミノピリジン、2,6−ジアミノピリジン、2,6−ジアミノ−4−メチルピリジン、4−ヒドロキシピリジン、2,6−ジヒドロキシピリジン、6−ヒドロキシニコチン酸メチル、2−ヒドロキシ−5−ピリジンメタノール、6−ヒドロキシニコチン酸エチル、4−ピリジンメタノール、4−ピリジンエタノール、2−フェニルピリジン、3−メチルキノリン、3−エチルキノリン、キノリノール、2,3−シクロペンテノピリジン、2,3−シクロペキサノピリジン、1,2−ジ(4−ピリジル)エタン、1,2−ジ(4−ピリジル)プロパン、2−ピリジンカルボキシアルデヒド、2−ピリジンカルボン酸、2−ピリジンカルボニトリル、2,3−ピリジンジカルボン酸、2,4−ピリジンジカルボン酸、2,5−ピリジンジカルボン酸、2,6−ピリジンジカルボン酸、3−ピリジンスルホン酸等があげられる。 Specific examples of pyridine containing one nitrogen atom and derivatives thereof include pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 4-ethylpyridine, 2,4-dimethylpyridine, 2, 4,6-trimethylpyridine, 3-cyano-5-methylpyridine, 2-pyridinecarboxylic acid, 6-methyl-2-pyridinecarboxylic acid, 2,6-pyridine-dicarboxylic acid, 4-pyridinecarboxaldehyde, 4-amino Pyridine, 2,3-diaminopyridine, 2,6-diaminopyridine, 2,6-diamino-4-methylpyridine, 4-hydroxypyridine, 2,6-dihydroxypyridine, methyl 6-hydroxynicotinate, 2-hydroxy- 5-pyridinemethanol, ethyl 6-hydroxynicotinate, 4-pyridinemethanol, 4 -Pyridineethanol, 2-phenylpyridine, 3-methylquinoline, 3-ethylquinoline, quinolinol, 2,3-cyclopentenopyridine, 2,3-cyclopexanopyridine, 1,2-di (4-pyridyl) ethane 1,2-di (4-pyridyl) propane, 2-pyridinecarboxaldehyde, 2-pyridinecarboxylic acid, 2-pyridinecarbonitrile, 2,3-pyridinedicarboxylic acid, 2,4-pyridinedicarboxylic acid, 2,5 -Pyridinedicarboxylic acid, 2,6-pyridinedicarboxylic acid, 3-pyridinesulfonic acid and the like.
二つの窒素原子を含有するイミダゾール及びその誘導体の具体的な例としては、イミダゾール、2−メチルイミダゾール、2−プロピルイミダゾール、2−ウンデジルイミダゾール、2−フェニルイミダゾール、N−メチルイミダゾール、1−(2−ヒドロキシエチル)イミダゾール、2−エチル-4-メチルイミダゾール、1,2−ジメチルイミダゾール、1−ベンジル−2−メチルイミダゾール、1−ベンジル−2−フェニルイミダゾール、1−シアノエチル−2−メチルイミダゾール、1−シアノエチル−2−エチル−4−メチルイミダゾール、2−フェニル−4,5−ジヒドロキシメチルイミダゾール、1−アセチルイミダゾール、4,5−イミダゾールジカルボン酸、4,5−イミダゾールジカルボン酸ジメチル、ベンズイミダゾール、2−アミノべンズイミダゾール、2−アミノべンズイミダゾール−2−スルホン酸、2−アミノ−1−メチルべンズイミダゾール、2−ヒドロキシべンズイミダゾール、2−(2−ピリジル)べンズイミダゾール等が挙げられる。 Specific examples of imidazole containing two nitrogen atoms and derivatives thereof include imidazole, 2-methylimidazole, 2-propylimidazole, 2-undecylimidazole, 2-phenylimidazole, N-methylimidazole, 1- ( 2-hydroxyethyl) imidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 1-acetylimidazole, 4,5-imidazole dicarboxylic acid, dimethyl 4,5-imidazole dicarboxylate, benzimidazole Examples include 2-aminobenzimidazole, 2-aminobenzimidazole-2-sulfonic acid, 2-amino-1-methylbenzimidazole, 2-hydroxybenzimidazole, and 2- (2-pyridyl) benzimidazole. It is done.
二つの窒素原子を含有するピリミジン及びその誘導体の具体的な例としては、2−アミノ−4−クロロ−6−メチルピリミジン、2−アミノ−6−クロロ−4−メトキシピリミジン、2−アミノ−4,6−ジクロロピリミジン、2−アミノ−4,6−ジヒドロキシピリミジン、2−アミノ−4,6−ジメチルピリミジン、2−アミノ−4,6−ジメトキシピリミジン、2−アミノピリミジン、2−アミノ−4−メチルピリミジン、4,6−ジヒドロキシピリミジン、2,4−ジヒドロキシピリミジン−5−カルボン酸、2,4,6−トリアミノピリミジン、2,4−ジメトキシピリミジン、2,4,5−トリヒドロキシピリミジン、2,4−ピリミジンジオール等が挙げられる。 Specific examples of pyrimidines containing two nitrogen atoms and derivatives thereof include 2-amino-4-chloro-6-methylpyrimidine, 2-amino-6-chloro-4-methoxypyrimidine, 2-amino-4 , 6-dichloropyrimidine, 2-amino-4,6-dihydroxypyrimidine, 2-amino-4,6-dimethylpyrimidine, 2-amino-4,6-dimethoxypyrimidine, 2-aminopyrimidine, 2-amino-4- Methylpyrimidine, 4,6-dihydroxypyrimidine, 2,4-dihydroxypyrimidine-5-carboxylic acid, 2,4,6-triaminopyrimidine, 2,4-dimethoxypyrimidine, 2,4,5-trihydroxypyrimidine, 2 , 4-pyrimidinediol and the like.
二つの窒素原子を含有するピラジン及びその誘導体の具体的な例としては、ピラジン、2−メチルピラジン、2,5−ジメチルピラジン、ピラジンカルボン酸、2,3−ピラジンジカルボン酸、5−メチルピラジンカルボン酸、ピラジンアミド、5−メチルピラジンアミド、2−シアノピラジン、アミノピラジン、3−アミノピラジン−2−カルボン酸、2−エチル−3-メチルピラジン、2−エチル−3−メチルピラジン、2,3−ジメチルピラジン、2,3−ジエチルピラジン等が挙げられる。 Specific examples of pyrazine and its derivatives containing two nitrogen atoms include pyrazine, 2-methylpyrazine, 2,5-dimethylpyrazine, pyrazinecarboxylic acid, 2,3-pyrazinedicarboxylic acid, and 5-methylpyrazinecarboxylic acid. Acid, pyrazineamide, 5-methylpyrazineamide, 2-cyanopyrazine, aminopyrazine, 3-aminopyrazine-2-carboxylic acid, 2-ethyl-3-methylpyrazine, 2-ethyl-3-methylpyrazine, 2,3 -Dimethylpyrazine, 2,3-diethylpyrazine and the like.
三つの窒素原子を含有するトリアジン及びその誘導体の具体的な例としては、1,3,5−トリアジン、2−アミノ−1,3,5−トリアジン、3−アミノ−1,2,4−トリアジン、2,4−ジアミノ−6−フェニル−1,3,5−トリアジン、2,4,6−トリアミノ−1,3,5−トリアジン、2,4,6−トリス(トリフルオロメチル)−1,3,5−トリアジン、2,4,6−トリ−2−ピリジン−1,3,5−トリアジン、3−(2−ピリジン)−5,6−ビス(4−フェニルスルホン酸)−1,2,4−トリアジン二ナトリウム、3−(2−ピリジン)−5,6−ジフェニル−1,2,4−トリアジン、3−(2−ピリジン)−5,6−ジフェニル−1,2,4−トリアジン−ρ,ρ’−ジスルホン酸二ナトリウム、2−ヒドロキシ−4,6−ジクロロ−1,3,5、−トリアジン等が挙げられる。
また、前記窒素含有芳香環化合物に他の官能基を付加することによって得られる前記窒素含有芳香環化合物カチオンと陰イオンで構成される塩を添加しても同様の効果が得られる。
窒素含有芳香環化合物とカチオンを形成する官能基としては、水素、アルキル基、ヒドロキシル基、カルボキシル基、シアノ基、フェニル基、フェノ−ル基、エステル基、アルコキシル基、カルボニル基等が挙げられる。
前記陰イオンとしては、前記窒素含有芳香環化合物カチオンと塩を構成すれば、ここで特に限定されるものではない。例えば、ハロゲンイオン、硫酸イオン、亜塩酸イオン、前記有機スルホン酸イオン等が挙げられる。
Specific examples of triazine and its derivatives containing three nitrogen atoms include 1,3,5-triazine, 2-amino-1,3,5-triazine, and 3-amino-1,2,4-triazine. 2,4-diamino-6-phenyl-1,3,5-triazine, 2,4,6-triamino-1,3,5-triazine, 2,4,6-tris (trifluoromethyl) -1, 3,5-triazine, 2,4,6-tri-2-pyridine-1,3,5-triazine, 3- (2-pyridine) -5,6-bis (4-phenylsulfonic acid) -1,2 , 4-Triazine disodium, 3- (2-pyridine) -5,6-diphenyl-1,2,4-triazine, 3- (2-pyridine) -5,6-diphenyl-1,2,4-triazine -Ρ, ρ'-disulphonic acid disodium salt, 2-hydro Shi-4,6-dichloro-1,3,5, - triazine.
The same effect can be obtained by adding a salt composed of the nitrogen-containing aromatic ring compound cation and an anion obtained by adding another functional group to the nitrogen-containing aromatic ring compound.
Examples of the functional group that forms a cation with the nitrogen-containing aromatic ring compound include hydrogen, an alkyl group, a hydroxyl group, a carboxyl group, a cyano group, a phenyl group, a phenol group, an ester group, an alkoxyl group, and a carbonyl group.
The anion is not particularly limited as long as it forms a salt with the nitrogen-containing aromatic ring compound cation. For example, halogen ion, sulfate ion, chlorite ion, the above-mentioned organic sulfonate ion and the like can be mentioned.
窒素含有芳香環化合物の含有量は、ポリアニオンのアニオン基1モルに対して0.1〜100モルの範囲であることが好ましく、1〜30モルの範囲であることがより好ましく、固体電解質の物性及び導電性の観点から3〜10モルの範囲であることが特に好ましい。窒素含有芳香環化合物の含有量が0.1モルより少なくなると、窒素含有芳香環化合物とドーパント及びπ共役系導電性高分子との相互作用が弱く、充分な効果が得られず高い導電性が得られにくく、固体電解質中に窒素含環化有芳香合物が100モルを超えて含まれるとπ共役系導電性高分子の含有量が少なくなり、やはり充分な導電性が低くなる傾向にある。 The content of the nitrogen-containing aromatic ring compound is preferably in the range of 0.1 to 100 mol, more preferably in the range of 1 to 30 mol, based on 1 mol of the anion group of the polyanion, and the physical properties of the solid electrolyte And from the viewpoint of conductivity, the range of 3 to 10 mol is particularly preferable. When the content of the nitrogen-containing aromatic ring compound is less than 0.1 mol, the interaction between the nitrogen-containing aromatic ring compound, the dopant, and the π-conjugated conductive polymer is weak, and a sufficient effect cannot be obtained with high conductivity. It is difficult to obtain, and when the nitrogen ring-containing aromatic compound exceeds 100 mol in the solid electrolyte, the content of the π-conjugated conductive polymer is decreased, and the sufficient conductivity tends to be lowered. .
<(c)2個以上のヒドロキシル基を有するヒドロキシル基含有芳香族性化合物>
2個以上のヒドロキシル基を有するヒドロキシル基含有芳香族性化合物は、芳香族環に、ヒドロキシル基が2個以上置換されているものである。例えば、1,4−ジヒドロキシベンゼン、1,3−ジヒドロキシベンゼン、2,3−ジヒドロキシ−1−ペンタデシルベンゼン、2,4−ジヒドロキシアセトフェノン、2,5−ジヒドロキシアセトフェノン、2,4−ジヒドロキシベンゾフェノン、2,6−ジヒドロキシベンゾフェノン、3,4−ジヒドロキシベンゾフェノン、3,5−ジヒドロキシベンゾフェノン、2,4’−ジヒドロキシジフェニルスルフォン、2,2’,5,5’−テトラヒドロキシジフェニルスルフォン、3,3’,5,5’−テトラメチル−4,4’−ジヒドロキシジフェニルスルフォン、ヒドロキシキノンカルボン酸及びその塩類、2,3−ジヒドロキシ安息香酸、2,4−ジヒドロキシ安息香酸、2,5−ジヒドロキシ安息香酸、2,6−ジヒドロキシ安息香酸、3,5−ジヒドロキシ安息香酸、1,4−ヒドロキノンスルホン酸及びその塩類、4,5−ヒドロキシベンゼン−1,3−ジスルホン酸及びその塩類、1,5−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、2,6−ジヒドロキシナフタレン、2,7−ジヒドロキシナフタレン、2,3−ジヒドロキシナフタレン、1,5−ジヒドロキシナフタレン−2,6−ジカルボン酸、1,6−ジヒドロキシナフタレン−2,5−ジカルボン酸、1,5−ジヒドロキシナフトエ酸、1,4−ジヒドロキシ−2−ナフトエ酸フェニルエステル、4,5−ジヒドロキシナフタレン−2,7−ジスルホン酸及びその塩類、1,8−ジヒドロキシ−3,6−ナフタレンジスルホン酸及びその塩類、6,7−ジヒドロキシ−2−ナフタレンスルホン酸及びその塩類、1,2,3−トリヒドロキシベンゼン(ピロガロール)、1,2,4−トリヒドロキシベンゼン、5−メチル−1,2,3−トリヒドロキシベンゼン、5−エチル−1,2,3−トリヒドロキシベンゼン、5−プロピル−1,2,3−トリヒドロキシベンゼン、トリヒドロキシ安息香酸、トリヒドロキシアセトフェノン、トリヒドロキシベンゾフェノン、トリヒドロキシベンゾアルデヒド、トリヒドロキシアントラキノン、2,4,6−トリヒドロキシベンゼン、テトラヒドロキシ−p−ベンゾキノン、テトラヒドロキシアントラキノン等が挙げられる。
ヒドロキシル基含有芳香族性化合物の中でも、導電性の点からは、π共役系導電性高分子にドーピングしうる、アニオン基であるスルホ基及び/又はカルボキシル基を有する化合物がより好ましい。
<(C) Hydroxyl group-containing aromatic compound having two or more hydroxyl groups>
The hydroxyl group-containing aromatic compound having two or more hydroxyl groups is one in which two or more hydroxyl groups are substituted on the aromatic ring. For example, 1,4-dihydroxybenzene, 1,3-dihydroxybenzene, 2,3-dihydroxy-1-pentadecylbenzene, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,4-dihydroxybenzophenone, 2 , 6-dihydroxybenzophenone, 3,4-dihydroxybenzophenone, 3,5-dihydroxybenzophenone, 2,4′-dihydroxydiphenyl sulfone, 2,2 ′, 5,5′-tetrahydroxydiphenyl sulfone, 3,3 ′, 5 , 5′-tetramethyl-4,4′-dihydroxydiphenylsulfone, hydroxyquinonecarboxylic acid and its salts, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2, 6-dihydroxybenzoic acid, 3 5-dihydroxybenzoic acid, 1,4-hydroquinonesulfonic acid and its salts, 4,5-hydroxybenzene-1,3-disulfonic acid and its salts, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 1,5-dihydroxynaphthalene-2,6-dicarboxylic acid, 1,6-dihydroxynaphthalene-2,5-dicarboxylic acid, 1,5 -Dihydroxynaphthoic acid, 1,4-dihydroxy-2-naphthoic acid phenyl ester, 4,5-dihydroxynaphthalene-2,7-disulfonic acid and its salts, 1,8-dihydroxy-3,6-naphthalenedisulfonic acid and its Salts, 6,7-dihydroxy-2-naphthalenesulfonic acid And salts thereof, 1,2,3-trihydroxybenzene (pyrogallol), 1,2,4-trihydroxybenzene, 5-methyl-1,2,3-trihydroxybenzene, 5-ethyl-1,2,3- Trihydroxybenzene, 5-propyl-1,2,3-trihydroxybenzene, trihydroxybenzoic acid, trihydroxyacetophenone, trihydroxybenzophenone, trihydroxybenzaldehyde, trihydroxyanthraquinone, 2,4,6-trihydroxybenzene, Examples thereof include tetrahydroxy-p-benzoquinone and tetrahydroxyanthraquinone.
Among the hydroxyl group-containing aromatic compounds, from the viewpoint of conductivity, compounds having a sulfo group and / or a carboxyl group, which are anionic groups, which can be doped into the π-conjugated conductive polymer are more preferable.
ヒドロキシル基置換芳香族性化合物の含有量は、ポリアニオンのアニオン基単位1モルに対して0.05〜10モルの範囲であることが好ましく、0.3〜5モルの範囲であることがより好ましい。ヒドロキシル基置換芳香族性化合物の含有量が、ポリアニオンのアニオン基単位1モルに対して0.05モルより少なくなると、導電性及び耐熱性が不足することがある。また、ヒドロキシル基置換芳香族性化合物の含有量が、ポリアニオンのアニオン基単位1モルに対して10モルより多くなると、固体電解質中のπ共役系導電性高分子の含有量が少なくなり、やはり充分な導電性が得られにくくなることがある。 The content of the hydroxyl group-substituted aromatic compound is preferably in the range of 0.05 to 10 mol, more preferably in the range of 0.3 to 5 mol, per 1 mol of the anion group unit of the polyanion. . When the content of the hydroxyl group-substituted aromatic compound is less than 0.05 mol with respect to 1 mol of the anion group unit of the polyanion, conductivity and heat resistance may be insufficient. Moreover, when the content of the hydroxyl group-substituted aromatic compound is more than 10 moles relative to 1 mole of the anion group unit of the polyanion, the content of the π-conjugated conductive polymer in the solid electrolyte is decreased, which is also sufficient. May be difficult to obtain.
<(d)グリシジル基を有する化合物>
グリシジル基を有する化合物としては、下記(d−1)〜(d−3)の化合物が挙げられる。
(d−1):グリシジル基と、アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種とを有する化合物(以下、化合物(d−1)という。)。
(d−2):グリシジル基を2つ以上有する化合物(以下、化合物(d−2)という。)。
(d−3):グリシジル基を1つ有する化合物であって、化合物(d−1)以外の化合物(以下、化合物(d−3)という。)。
<(D) Compound having glycidyl group>
Examples of the compound having a glycidyl group include the following compounds (d-1) to (d-3).
(D-1): A compound having a glycidyl group and one kind selected from an allyl group, a vinyl ether group, a methacryl group, an acrylic group, a methacrylamide group, and an acrylamide group (hereinafter referred to as compound (d-1)).
(D-2): a compound having two or more glycidyl groups (hereinafter referred to as compound (d-2)).
(D-3): A compound having one glycidyl group, and a compound other than the compound (d-1) (hereinafter referred to as compound (d-3)).
化合物(d−1)のうち、グリシジル基とアクリル(メタクリル)基を有する化合物として、グリシジルアクリレート、グリシジルメタクリレート等が挙げられる。
グリシジル基とアリル基を有する化合物として、アリルグリシジルエーテル、2−メチルアリルグリシジルエーテル、アリルフェノールグリシジルエーテル等が挙げられる。
グリシジル基とヒドロキシル基とを有する化合物として、1,4−ジヒドロキシメチルベンゼンジグリシジルエーテル、グリセリンジグリシジルエーテル等が挙げられる。
グリシジル基とヒドロキシル基とアリル基とを有する化合物として、3−アリル−1,4−ジヒドロキシメチルベンゼンジグリシジルエーテル等が挙げられる。
Among the compounds (d-1), examples of the compound having a glycidyl group and an acrylic (methacrylic) group include glycidyl acrylate and glycidyl methacrylate.
Examples of the compound having a glycidyl group and an allyl group include allyl glycidyl ether, 2-methylallyl glycidyl ether, and allylphenol glycidyl ether.
Examples of the compound having a glycidyl group and a hydroxyl group include 1,4-dihydroxymethylbenzene diglycidyl ether and glycerin diglycidyl ether.
Examples of the compound having a glycidyl group, a hydroxyl group, and an allyl group include 3-allyl-1,4-dihydroxymethylbenzene diglycidyl ether.
化合物(d−2)としては、例えば、エチレングリコールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ビスフェノールAジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、ダイマー酸ジグリシジルエステル、フタル酸ジグリシジル、トリグリシジルイソシアヌレート、テトラグリシジルジアミノジフェニルメタン、ジグリシジルテトラフタレート等が挙げられ1種類または2種類以上の混合として用いることができる。 Examples of the compound (d-2) include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, bisphenol A diglycidyl ether, polyethylene glycol diglycidyl ether. , Propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, dimer acid diglycidyl ester, diglycidyl phthalate, triglycidyl isocyanurate, tetraglycidyl diaminodiphenylmethane, diglycidyl tetraphthalate, etc. Or it can be used as a mixture of two or more.
化合物(d−3)としては、例えば、アルキルグリシジルエーテル、エチレングリコールグリシジルエーテル、メチルグリシジルエーテル、フェニルグリシジルエーテル、ブチルフェニルグリシジルエーテル、クレジルグリシジルエーテル等が挙げられる。 Examples of the compound (d-3) include alkyl glycidyl ether, ethylene glycol glycidyl ether, methyl glycidyl ether, phenyl glycidyl ether, butylphenyl glycidyl ether, and cresyl glycidyl ether.
グリシジル基を有する化合物の含有量は、ポリアニオンのアニオン基に対して、0.1〜100モル当量であることが好ましく、2〜50モル当量であることがより好ましい。グリシジル基を有する化合物含有量がポリアニオンのアニオン基に対して100モル当量を超える場合には、当該化合物が過剰になり、導電性を低下させるおそれがある。また、ポリアニオンのアニオン基に対して0.1モル当量未満では、導電性、耐熱性、成膜性、耐磨耗性、基材密着性を向上させることが困難になる傾向にある。 The content of the compound having a glycidyl group is preferably 0.1 to 100 molar equivalents, and more preferably 2 to 50 molar equivalents, relative to the anion group of the polyanion. When the content of the compound having a glycidyl group exceeds 100 molar equivalents relative to the anion group of the polyanion, the compound becomes excessive and there is a possibility that the conductivity is lowered. Moreover, if it is less than 0.1 molar equivalent with respect to the anion group of a polyanion, it exists in the tendency for it to become difficult to improve electroconductivity, heat resistance, film-forming property, abrasion resistance, and base-material adhesiveness.
[(e)アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種と、ヒドロキシル基とを有する化合物]
アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種と、ヒドロキシル基とを有する化合物のうち、例えば、ヒドロキシル基とビニルエーテル基とを有する化合物としては、2−ヒドロキシエチルビニルエーテル、4−ヒドロキシブチルビニルエーテル、ジエチレングリコールモノビニルエーテル等が挙げられる。
ヒドロキシル基とアクリル(メタクリル)基を有する化合物としては、2−ヒドロキシエチルアクリレート(メタクリレート)、2−ヒドロキシプロピルアクリレート(メタクリレート)、4−ヒドロキシブチルアクリレート(メタクリレート)、エチル−α−ヒドロキシメチルアクリレート、ジペンタエリストリトールモノヒドロキシペンタアクリレート等が挙げられる。
ヒドロキシル基とアクリルアミド(メタクリルアミド)基を有する化合物としては、2−ヒドロキシエチルアクリルアミド、2−ヒドロキシエチルメタクリルアミドが挙げられる。
[(E) Compound having one kind selected from allyl group, vinyl ether group, methacryl group, acrylic group, methacrylamide group, acrylamide group and hydroxyl group]
Among compounds having a hydroxyl group and one kind selected from an allyl group, a vinyl ether group, a methacryl group, an acrylic group, a methacrylamide group, and an acrylamide group, for example, as a compound having a hydroxyl group and a vinyl ether group, 2- Examples thereof include hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, diethylene glycol monovinyl ether and the like.
Examples of the compound having a hydroxyl group and an acrylic (methacrylic) group include 2-hydroxyethyl acrylate (methacrylate), 2-hydroxypropyl acrylate (methacrylate), 4-hydroxybutyl acrylate (methacrylate), ethyl-α-hydroxymethyl acrylate, di Examples include pentaerythritol monohydroxypentaacrylate.
Examples of the compound having a hydroxyl group and an acrylamide (methacrylamide) group include 2-hydroxyethyl acrylamide and 2-hydroxyethyl methacrylamide.
アリル基、ビニルエーテル基、メタクリル基、アクリル基、メタクリルアミド基、アクリルアミド基から選ばれる1種と、ヒドロキシル基とを有する化合物(e)の含有量は、ポリアニオンのアニオン基に対して0.1〜100モル当量であることが好ましく、2〜50モル当量であることがより好ましい。当該化合物(e)の含有量がポリアニオンのアニオン基に対して100モル当量を超える場合には、当該化合物(e)が過剰になり、導電性を低下させるおそれがある。また、ポリアニオンのアニオン基に対して0.1モル当量未満では、導電性、耐熱性、成膜性、耐磨耗性、基材密着性を向上させることが困難になる傾向にある。 The content of the compound (e) having one kind selected from an allyl group, a vinyl ether group, a methacryl group, an acryl group, a methacrylamide group, and an acrylamide group and a hydroxyl group is from 0.1 to the anion group of the polyanion. It is preferably 100 molar equivalents, and more preferably 2 to 50 molar equivalents. When content of the said compound (e) exceeds 100 molar equivalent with respect to the anion group of a polyanion, the said compound (e) will become excess and there exists a possibility of reducing electroconductivity. Moreover, if it is less than 0.1 molar equivalent with respect to the anion group of a polyanion, it exists in the tendency for it to become difficult to improve electroconductivity, heat resistance, film-forming property, abrasion resistance, and base-material adhesiveness.
[ドーパント]
固体電解質においては、ポリアニオン以外に他のドーパントを添加してもよい。他のドーパントとしては、π共役系導電性高分子を酸化還元させることができればドナー性のものであってもよく、アクセプタ性のものであってもよい。
[Dopant]
In the solid electrolyte, other dopants may be added in addition to the polyanion. Other dopants may be donor or acceptor as long as the π-conjugated conductive polymer can be oxidized and reduced.
<ドナー性ドーパント>
ドナー性ドーパントとしては、例えば、ナトリウム、カリウム等のアルカリ金属、カルシウム、マグネシウム等のアルカリ土類金属、テトラメチルアンモニウム、テトラエチルアンモニウム、テトラプロピルアンモニウム、テトラブチルアンモニウム、メチルトリエチルアンモニウム、ジメチルジエチルアンモニウム等の4級アミン化合物等が挙げられる。
<Donor dopant>
Examples of the donor dopant include alkali metals such as sodium and potassium, alkaline earth metals such as calcium and magnesium, tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, methyltriethylammonium, dimethyldiethylammonium, and the like. A quaternary amine compound etc. are mentioned.
<アクセプタ性ドーパント>
アクセプタ性ドーパントとしては、例えば、ハロゲン化合物、ルイス酸、プロトン酸、有機シアノ化合物、有機金属化合物、フラーレン、水素化フラーレン、水酸化フラーレン、カルボン酸化フラーレン、スルホン酸化フラーレン等を使用できる。
さらに、ハロゲン化合物としては、例えば、塩素(Cl2)、臭素(Br2)、ヨウ素(I2)、塩化ヨウ素(ICl)、臭化ヨウ素(IBr)、フッ化ヨウ素(IF)等が挙げられる。
ルイス酸としては、例えば、PF5、AsF5、SbF5、BF5、BCl5、BBr5、SO3等が挙げられる。
有機シアノ化合物としては、共役結合に二つ以上のシアノ基を含む化合物が使用できる。例えば、テトラシアノエチレン、テトラシアノエチレンオキサイド、テトラシアノベンゼン、ジクロロジシアノベンゾキノン(DDQ)、テトラシアノキノジメタン、テトラシアノアザナフタレン等が挙げられる。
<Acceptor dopant>
As the acceptor dopant, for example, a halogen compound, Lewis acid, proton acid, organic cyano compound, organometallic compound, fullerene, hydrogenated fullerene, hydroxylated fullerene, carboxylated fullerene, sulfonated fullerene, or the like can be used.
Furthermore, examples of the halogen compound include chlorine (Cl 2 ), bromine (Br 2 ), iodine (I 2 ), iodine chloride (ICl), iodine bromide (IBr), and iodine fluoride (IF). .
Examples of the Lewis acid include PF 5 , AsF 5 , SbF 5 , BF 5 , BCl 5 , BBr 5 , SO 3 and the like.
As the organic cyano compound, a compound containing two or more cyano groups in a conjugated bond can be used. Examples include tetracyanoethylene, tetracyanoethylene oxide, tetracyanobenzene, dichlorodicyanobenzoquinone (DDQ), tetracyanoquinodimethane, and tetracyanoazanaphthalene.
プロトン酸としては、無機酸、有機酸が挙げられる。さらに、無機酸としては、例えば、塩酸、硫酸、硝酸、リン酸、ホウフッ化水素酸、フッ化水素酸、過塩素酸等が挙げられる。また、有機酸としては、有機カルボン酸、有機スルホン酸等が挙げられる。 Examples of the protonic acid include inorganic acids and organic acids. Furthermore, examples of the inorganic acid include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, borohydrofluoric acid, hydrofluoric acid, and perchloric acid. Moreover, organic carboxylic acid, organic sulfonic acid, etc. are mentioned as an organic acid.
有機カルボン酸としては、脂肪族、芳香族、環状脂肪族等にカルボキシル基を一つ又は二つ以上を含むものを使用できる。例えば、ギ酸、酢酸、シュウ酸、安息香酸、フタル酸、マレイン酸、フマル酸、マロン酸、酒石酸、クエン酸、乳酸、コハク酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、トリフルオロ酢酸、ニトロ酢酸、トリフェニル酢酸等が挙げられる。 As the organic carboxylic acid, aliphatic, aromatic, cycloaliphatic or the like containing one or more carboxyl groups can be used. For example, formic acid, acetic acid, oxalic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, malonic acid, tartaric acid, citric acid, lactic acid, succinic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, nitroacetic acid, And triphenylacetic acid.
有機スルホン酸としては、脂肪族、芳香族、環状脂肪族等にスルホ基を一つ又は二つ以上含むもの、又は、スルホ基を含む高分子を使用できる。
スルホ基を一つ含むものとして、例えば、メタンスルホン酸、エタンスルホン酸、1−プロパンスルホン酸、1−ブタンスルホン酸、1−ヘキサンスルホン酸、1−ヘプタンスルホン酸、1−オクタンスルホン酸、1−ノナンスルホン酸、1−デカンスルホン酸、1−ドデカンスルホン酸、1−テトラデカンスルホン酸、1−ペンタデカンスルホン酸、2−ブロモエタンスルホン酸、3−クロロ−2−ヒドロキシプロパンスルホン酸、トリフルオロメタンスルホン酸、トリフルオロエタンスルホン酸、コリスチンメタンスルホン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、アミノメタンスルホン酸、1−アミノ−2−ナフトール−4−スルホン酸、2−アミノ−5−ナフトール−7−スルホン酸、3−アミノプロパンスルホン酸、N−シクロヘキシル−3−アミノプロパンスルホン酸、ベンゼンスルホン酸、アルキルベンゼンスルホン酸、p−トルエンスルホン酸、キシレンスルホン酸、エチルベンゼンスルホン酸、プロピルベンゼンスルホン酸、ブチルベンゼンスルホン酸、ペンチルベンゼンスルホン酸、ヘキチルベンゼンスルホン酸、ヘプチルベンゼンスルホン酸、オクチルベンゼンスルホン酸、ノニルベンゼンスルホン酸、デシルベンゼンスルホン酸、ウンデシルベンゼンスルホン酸、ドデシルベンゼンスルホン酸、ペンタデシルベンゼンスルホン酸、ヘキサデシルベンゼンスルホン酸、2,4−ジメチルベンゼンスルホン酸、ジプロピルベンゼンスルホン酸、4−アミノベンゼンスルホン酸、o−アミノベンゼンスルホン酸、m−アミノベンゼンスルホン酸、4−アミノ−2−クロロトルエン−5−スルホン酸、4−アミノ−3−メチルベンゼン−1−スルホン酸、4−アミノ−5−メトキシ−2−メチルベンゼンスルホン酸、2−アミノ−5−メチルベンゼン−1−スルホン酸、4−アミノ−2−メチルベンゼン−1−スルホン酸、5−アミノ−2−メチルベンゼン−1−スルホン酸、4−アミノ−3−メチルベンゼン−1−スルホン酸、4−アセトアミド−3−クロロベンゼンスルホン酸、4−クロロ−3−ニトロベンゼンスルホン酸、p−クロロベンゼンスルホン酸、ナフタレンスルホン酸、メチルナフタレンスルホン酸、プロピルナフタレンスルホン酸、ブチルナフタレンスルホン酸、ペンチルナフタレンスルホン酸、4−アミノ−1−ナフタレンスルホン酸、8−クロロナフタレン−1−スルホン酸、ナフタレンスルホン酸ホルマリン重縮合物、メラミンスルホン酸ホルマリン重縮合物、アントラキノンスルホン酸、ピレンスルホン酸等が挙げられる。また、これらの金属塩も使用できる。
As the organic sulfonic acid, aliphatic, aromatic, cycloaliphatic or the like containing one or more sulfo groups, or a polymer containing sulfo groups can be used.
As one containing one sulfo group, for example, methanesulfonic acid, ethanesulfonic acid, 1-propanesulfonic acid, 1-butanesulfonic acid, 1-hexanesulfonic acid, 1-heptanesulfonic acid, 1-octanesulfonic acid, 1 -Nonanesulfonic acid, 1-decanesulfonic acid, 1-dodecanesulfonic acid, 1-tetradecanesulfonic acid, 1-pentadecanesulfonic acid, 2-bromoethanesulfonic acid, 3-chloro-2-hydroxypropanesulfonic acid, trifluoromethanesulfone Acid, trifluoroethanesulfonic acid, colistin methanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, aminomethanesulfonic acid, 1-amino-2-naphthol-4-sulfonic acid, 2-amino-5-naphthol- 7-sulfonic acid, 3-aminopropanesulfone N-cyclohexyl-3-aminopropanesulfonic acid, benzenesulfonic acid, alkylbenzenesulfonic acid, p-toluenesulfonic acid, xylenesulfonic acid, ethylbenzenesulfonic acid, propylbenzenesulfonic acid, butylbenzenesulfonic acid, pentylbenzenesulfonic acid, hex Tylbenzenesulfonic acid, heptylbenzenesulfonic acid, octylbenzenesulfonic acid, nonylbenzenesulfonic acid, decylbenzenesulfonic acid, undecylbenzenesulfonic acid, dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid, hexadecylbenzenesulfonic acid, 2, 4-dimethylbenzenesulfonic acid, dipropylbenzenesulfonic acid, 4-aminobenzenesulfonic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid 4-amino-2-chlorotoluene-5-sulfonic acid, 4-amino-3-methylbenzene-1-sulfonic acid, 4-amino-5-methoxy-2-methylbenzenesulfonic acid, 2-amino-5-methyl Benzene-1-sulfonic acid, 4-amino-2-methylbenzene-1-sulfonic acid, 5-amino-2-methylbenzene-1-sulfonic acid, 4-amino-3-methylbenzene-1-sulfonic acid, 4 -Acetamide-3-chlorobenzenesulfonic acid, 4-chloro-3-nitrobenzenesulfonic acid, p-chlorobenzenesulfonic acid, naphthalenesulfonic acid, methylnaphthalenesulfonic acid, propylnaphthalenesulfonic acid, butylnaphthalenesulfonic acid, pentylnaphthalenesulfonic acid, 4 -Amino-1-naphthalenesulfonic acid, 8-chloronaphthalene-1- Examples include sulfonic acid, naphthalene sulfonic acid formalin polycondensate, melamine sulfonic acid formalin polycondensate, anthraquinone sulfonic acid, and pyrene sulfonic acid. These metal salts can also be used.
スルホ基を二つ以上含むものとしては、例えば、エタンジスルホン酸、ブタンジスルホン酸、ペンタンジスルホン酸、デカンジスルホン酸、o−ベンゼンジスルホン酸、m−ベンゼンジスルホン酸、p−ベンゼンジスルホン酸、トルエンジスルホン酸、キシレンジスルホン酸、クロロベンゼンジスルホン酸、フルオロベンゼンジスルホン酸、ジメチルベンゼンジスルホン酸、ジエチルベンゼンジスルホン酸、アニリン−2,4−ジスルホン酸、アニリン−2,5−ジスルホン酸、3,4−ジヒドロキシ−1,3−ベンゼンジスルホン酸、ナフタレンジスルホン酸、メチルナフタレンジスルホン酸、エチルナフタレンジスルホン酸、ペンタデシルナフタレンジスルホン酸、3−アミノ−5−ヒドロキシ−2,7−ナフタレンジスルホン酸、1−アセトアミド−8−ヒドロキシ−3,6−ナフタレンジスルホン酸、2−アミノ−1,4−ベンゼンジスルホン酸、1−アミノ−3,8−ナフタレンジスルホン酸、3−アミノ−1,5−ナフタレンジスルホン酸、8−アミノ−1−ナフトール−3,6−ジスルホン酸、4−アミノ−5−ナフトール−2,7−ジスルホン酸、4−アセトアミド−4’−イソチオ−シアノトスチルベン−2,2’−ジスルホン酸、4−アセトアミド−4’−イソチオシアナトスチルベン−2,2’−ジスルホン酸、4−アセトアミド−4’−マレイミジルスチルベン−2,2’−ジスルホン酸、ナフタレントリスルホン酸、ジナフチルメタンジスルホン酸、アントラキノンジスルホン酸、アントラセンスルホン酸等が挙げられる。また、これらの金属塩も使用できる。 Examples of those containing two or more sulfo groups include ethanedisulfonic acid, butanedisulfonic acid, pentanedisulfonic acid, decanedisulfonic acid, o-benzenedisulfonic acid, m-benzenedisulfonic acid, p-benzenedisulfonic acid, and toluenedisulfonic acid. Xylene disulfonic acid, chlorobenzene disulfonic acid, fluorobenzene disulfonic acid, dimethylbenzene disulfonic acid, diethylbenzene disulfonic acid, aniline-2,4-disulfonic acid, aniline-2,5-disulfonic acid, 3,4-dihydroxy-1,3 -Benzenedisulfonic acid, naphthalene disulfonic acid, methyl naphthalene disulfonic acid, ethyl naphthalene disulfonic acid, pentadecyl naphthalene disulfonic acid, 3-amino-5-hydroxy-2,7-naphthalene disulfonic acid, 1- Cetamide-8-hydroxy-3,6-naphthalenedisulfonic acid, 2-amino-1,4-benzenedisulfonic acid, 1-amino-3,8-naphthalenedisulfonic acid, 3-amino-1,5-naphthalenedisulfonic acid, 8-Amino-1-naphthol-3,6-disulfonic acid, 4-amino-5-naphthol-2,7-disulfonic acid, 4-acetamido-4'-isothio-cyanotostilbene-2,2'-disulfonic acid 4-acetamido-4′-isothiocyanatostilbene-2,2′-disulfonic acid, 4-acetamido-4′-maleimidylstilbene-2,2′-disulfonic acid, naphthalenetrisulfonic acid, dinaphthylmethanedisulfone An acid, anthraquinone disulfonic acid, anthracene sulfonic acid, etc. are mentioned. These metal salts can also be used.
本発明の固体電解質は、上記特定のπ共役系導電性高分子を含有するため、導電性及び耐熱性に優れている。このような固体電解質は、例えば、電極や固体電解質膜、帯電防止膜などとして好適に利用できる。 Since the solid electrolyte of the present invention contains the specific π-conjugated conductive polymer, it is excellent in conductivity and heat resistance. Such a solid electrolyte can be suitably used as, for example, an electrode, a solid electrolyte membrane, or an antistatic membrane.
(電解コンデンサ及びその製造方法)
以下、本発明の電解コンデンサ及びその製造方法について説明する。
図1に、本発明の電解コンデンサの一例を示す。この電解コンデンサ10は、弁金属の多孔質体からなる陽極11と、陽極11の表面が酸化されて形成された誘電体層12と、誘電体層12上に形成された陰極13とを有して概略構成されている。
(Electrolytic capacitor and manufacturing method thereof)
Hereinafter, the electrolytic capacitor of the present invention and the manufacturing method thereof will be described.
FIG. 1 shows an example of the electrolytic capacitor of the present invention. The
陽極11をなす弁金属としては、例えば、アルミニウム、タンタル、ニオブ、チタン、ハフニウム、ジルコニウム、亜鉛、タングステン、ビスマス、アンチモンなどが挙げられる。これらのうち、アルミニウム、タンタル、ニオブが好適である。
陽極11の具体例としては、アルミニウム箔をエッチングして表面積を増加させた後、その表面を酸化処理したものや、タンタル粒子やニオブ粒子の焼結体表面を酸化処理してペレットにしたものが挙げられる。このように処理されたものは表面に凹凸が形成されている。
Examples of the valve metal forming the
Specific examples of the
誘電体層12は、例えば、アジピン酸アンモニウム水溶液などの電解液中にて、陽極11の表面を陽極酸化することで形成されたものである。よって、図1に示すように、陽極11と同様に誘電体層12の表面にも凹凸が形成されている。
The
陰極13は、固体電解質層13aと、固体電解質層13a上に形成されたカーボン、銀、アルミニウム等で構成されている陰極導電層13bとを具備し、固体電解質層が上記固体電解質からなるものである。
陰極導電層13bがカーボン、銀等で構成される場合には、例えば、カーボン、銀等の導電体を含む導電性ペーストから形成することができる。また、陰極導電層13bがアルミニウムで構成される場合には、例えば、アルミニウム箔から形成することができる。
また、固体電解質層13aと陰極導電層13bとの間には、必要に応じて、セパレータを設けることができる。
The
When the
Moreover, a separator can be provided between the
本発明の電解コンデンサの製造方法では、まず、弁金属の多孔質体からなる陽極と該陽極の表面が酸化されて形成された酸化被膜の誘電体層とを有するコンデンサ中間体を用意し、そのコンデンサ中間体の誘電体層側表面に、上記π共役系導電性高分子とポリアニオンと溶媒とを含む導電性高分子溶液を塗布して固体電解質層を形成する。次いで、その固体電解質層上に、カーボンペースト、銀ペーストによって陰極を形成したり、セパレータを介して陰極電極を対向したりして陰極を形成して電解コンデンサを得る。
ここで、導電性高分子溶液は、例えば、ポリアニオンを、これを溶解する溶媒に溶解してポリアニオン溶液を調製し、このポリアニオン溶液にπ共役系導電性高分子の前駆体モノマーを加え、さらに酸化剤を加えて前駆体モノマーを重合する。その後、余剰の酸化剤や前駆体モノマーを分離、精製することにより得られる。
導電性高分子溶液の塗布方法としては、例えば、コーティング、浸漬、スプレーなどの方法を採ることができる。
このような、導電性高分子溶液を塗布する方法は、工程が簡便であり、大量生産に向いており、コストも安く出来るという利点を有する。
In the method for producing an electrolytic capacitor of the present invention, first, a capacitor intermediate having an anode made of a porous body of valve metal and an oxide film dielectric layer formed by oxidizing the surface of the anode is prepared, A conductive polymer solution containing the π-conjugated conductive polymer, polyanion, and solvent is applied to the dielectric layer side surface of the capacitor intermediate to form a solid electrolyte layer. Next, on the solid electrolyte layer, a cathode is formed by carbon paste or silver paste, or a cathode electrode is opposed through a separator to form a cathode, thereby obtaining an electrolytic capacitor.
Here, the conductive polymer solution is prepared by, for example, preparing a polyanion solution by dissolving a polyanion in a solvent for dissolving the polyanion, adding a precursor monomer of a π-conjugated conductive polymer to the polyanion solution, and further oxidizing the polyanion solution. An agent is added to polymerize the precursor monomer. Thereafter, it is obtained by separating and purifying excess oxidant and precursor monomer.
As a method for applying the conductive polymer solution, for example, a method such as coating, dipping or spraying can be employed.
Such a method of applying the conductive polymer solution has advantages that the process is simple, suitable for mass production, and cost can be reduced.
なお、本発明の電解コンデンサは、上記製造方法以外の方法で製造することもできる。例えば、固体電解質層を形成する際に、上記のように導電性高分子溶液を塗布する方法以外に、化学酸化重合法、電解重合法を適用することができる。
化学酸化重合では、例えば、上記π共役系導電性高分子の前駆体モノマー溶液と酸化剤の溶液とをそれぞれ用意し、コンデンサ中間体をこれらに交互に浸漬してコンデンサ中間体表面に導電性高分子を重合させる。
電解重合では、例えば、アセトニトリルなどの溶媒にモノマーを加え、ドーパントを電解質として加えた電解槽に表面に導電層を形成したコンデンサ中間体を電極として仕込み、電圧を加えることによってコンデンサ中間体上に固体電解質を重合させる。
In addition, the electrolytic capacitor of this invention can also be manufactured by methods other than the said manufacturing method. For example, when forming the solid electrolyte layer, a chemical oxidation polymerization method and an electrolytic polymerization method can be applied in addition to the method of applying the conductive polymer solution as described above.
In chemical oxidative polymerization, for example, a precursor monomer solution of the π-conjugated conductive polymer and a solution of an oxidizing agent are prepared, respectively, and a capacitor intermediate is alternately immersed in these, so that the surface of the capacitor intermediate has high conductivity. Polymerize the molecules.
In electrolytic polymerization, for example, a capacitor intermediate in which a conductive layer is formed on an electrolytic cell in which a monomer is added to a solvent such as acetonitrile and a dopant is added as an electrolyte is used as an electrode, and a solid is formed on the capacitor intermediate by applying voltage. Polymerize the electrolyte.
本発明の電解コンデンサは、陰極として、上記固体電解質を含み、導電性に優れた固体電解質層を備えるものを用いているため、ESRが低く、高容量にできる上に、漏れ電流を小さくできる。また、耐熱性にも優れるため、苛酷な条件に耐えうる。 Since the electrolytic capacitor of the present invention includes a solid electrolyte layer that includes the above solid electrolyte and is excellent in conductivity as a cathode, the ESR is low, the capacity can be increased, and the leakage current can be reduced. Moreover, since it is excellent in heat resistance, it can withstand severe conditions.
以下、実施例により本発明をさらに詳しく説明する。
(合成例1)チオフェン単量体(I)の合成
69.6gの3,4−ジヒドロキシ−2,5−ジカルボキシジメチルエステルと、28.2gのN,N’−ジメチル−1,2−エチレンジアミンと、0.5gのp−トルエンスルホン酸を、100mlのN,N’−ジメチルアセトアミドと250mlのトルエンに加え、24時間還流して反応液を得た。その後、その反応液を20℃まで冷却し、さらに100mlのトルエンを加えた。これに200mlの5質量%塩酸水溶液を添加して抽出を行った。この操作を4回繰り返した後、得られた塩酸層に10質量%の水酸化ナトリウム水溶液を添加し、150mlのトルエンで3回抽出を行った。そして、これを分留して化学式(3)で表されるチオフェン単量体(I)7.8gを得た。
Hereinafter, the present invention will be described in more detail with reference to examples.
Synthesis Example 1 Synthesis of Thiophene Monomer (I) 69.6 g of 3,4-dihydroxy-2,5-dicarboxydimethyl ester and 28.2 g of N, N′-dimethyl-1,2-ethylenediamine Then, 0.5 g of p-toluenesulfonic acid was added to 100 ml of N, N′-dimethylacetamide and 250 ml of toluene, and refluxed for 24 hours to obtain a reaction solution. Thereafter, the reaction solution was cooled to 20 ° C., and 100 ml of toluene was further added. 200 ml of 5 mass% hydrochloric acid aqueous solution was added to this and extracted. After repeating this operation four times, a 10% by mass aqueous sodium hydroxide solution was added to the resulting hydrochloric acid layer, and extraction was performed three times with 150 ml of toluene. This was fractionated to obtain 7.8 g of thiophene monomer (I) represented by chemical formula (3).
(実施例1)導電性高分子水溶液の合成
16.8g(0.1mol)のチオフェン単量体(I)と、27.5g(0.15mol)のポリスチレンスルホン酸(質量平均分子量;約150,000)とを2000mlのイオン交換水に溶解してモノマー混合液を得た。このモノマー混合液を20℃に保ち、これに、200mlのイオン交換水に溶解した29.64g(0.13mol)の過硫酸アンモニウムと8.0g(0.02mol)の硫酸第二鉄の溶液を、攪拌しながら加え、1時間反応させた。得られた反応液を透析し、未反応モノマー及び酸化剤を除去して、1.5質量%のポリスチレンスルホン酸ドープポリチオフェン(I)を得た。
得られた水溶液を導電性高分子溶液としてガラス板上に塗布し、120℃の熱風乾燥機で乾燥して導電膜を形成し、その導電膜の電気伝導度をローレスタ(三菱化学社製)により測定した。その結果を表1に示す。
(Example 1) Synthesis of aqueous conductive polymer solution 16.8 g (0.1 mol) of thiophene monomer (I) and 27.5 g (0.15 mol) of polystyrene sulfonic acid (mass average molecular weight; about 150, 000) was dissolved in 2000 ml of ion exchange water to obtain a monomer mixture. This monomer mixture was kept at 20 ° C., and a solution of 29.64 g (0.13 mol) ammonium persulfate and 8.0 g (0.02 mol) ferric sulfate dissolved in 200 ml of ion-exchanged water was It was added with stirring and allowed to react for 1 hour. The obtained reaction solution was dialyzed to remove unreacted monomers and oxidant to obtain 1.5% by mass of polystyrenesulfonic acid-doped polythiophene (I).
The obtained aqueous solution was applied as a conductive polymer solution on a glass plate, dried with a hot air dryer at 120 ° C. to form a conductive film, and the electrical conductivity of the conductive film was measured by Loresta (manufactured by Mitsubishi Chemical Corporation). It was measured. The results are shown in Table 1.
(実施例2)
実施例1で得たポリスチレンスルホン酸ドープポリチオフェン(I)溶液100mlに2.5gのイミダゾールを添加した以外は実施例1と同様にして導電性高分子溶液を得た。そして、実施例1と同様にして電気伝導度を測定した。その結果を表1に示す。
(Example 2)
A conductive polymer solution was obtained in the same manner as in Example 1 except that 2.5 g of imidazole was added to 100 ml of the polystyrenesulfonic acid-doped polythiophene (I) solution obtained in Example 1. Then, the electrical conductivity was measured in the same manner as in Example 1. The results are shown in Table 1.
(実施例3)
実施例1で得たポリスチレンスルホン酸ドープポリチオフェン(I)溶液100mlに2.8gの1,4−ジヒドロキシベンゼンを添加した以外は実施例1と同様にして導電性高分子溶液を得た。そして、実施例1と同様にして電気伝導度を測定した。その結果を表1に示す。
(Example 3)
A conductive polymer solution was obtained in the same manner as in Example 1 except that 2.8 g of 1,4-dihydroxybenzene was added to 100 ml of the polystyrenesulfonic acid-doped polythiophene (I) solution obtained in Example 1. Then, the electrical conductivity was measured in the same manner as in Example 1. The results are shown in Table 1.
(実施例4)
実施例1で得たポリスチレンスルホン酸ドープポリスチレンスルホン酸ドープポリチオフェン(I)溶液100mlに1.2gのグリシジルアクリレートを添加した以外は実施例1と同様にして導電性高分子溶液を得た。そして、実施例1と同様にして電気伝導度を測定した。その結果を表1に示す。
Example 4
A conductive polymer solution was obtained in the same manner as in Example 1 except that 1.2 g of glycidyl acrylate was added to 100 ml of the polystyrenesulfonic acid-doped polystyrenesulfonic acid-doped polythiophene (I) solution obtained in Example 1. Then, the electrical conductivity was measured in the same manner as in Example 1. The results are shown in Table 1.
(実施例5)
実施例1で得たポリスチレンスルホン酸ドープポリスチレンスルホン酸ドープポリチオフェン(I)溶液100mlに2.2gのアセトアミドを添加した以外は実施例1と同様にして導電性高分子溶液を得た。そして、実施例1と同様にして電気伝導度を測定した。その結果を表1に示す。
(Example 5)
A conductive polymer solution was obtained in the same manner as in Example 1 except that 2.2 g of acetamide was added to 100 ml of the polystyrenesulfonic acid-doped polystyrenesulfonic acid-doped polythiophene (I) solution obtained in Example 1. Then, the electrical conductivity was measured in the same manner as in Example 1. The results are shown in Table 1.
表1に示すように、化学式(1)で表されるポリチオフェンを含む実施例1〜5の導電性高分子溶液は、電気伝導度(導電性)に優れていた。 As shown in Table 1, the conductive polymer solutions of Examples 1 to 5 containing polythiophene represented by the chemical formula (1) were excellent in electrical conductivity (conductivity).
(実施例6)電解コンデンサの作製
エッチドアルミ箔に、陽極リード端子を接続した後、アジピン酸アンモニウム10%水溶液中で化成して、表面に誘電体酸化皮膜を形成し、コンデンサ中間体とした。
次に、陰極リード端子を溶接させた対向アルミ陰極箔と、前記の陽極箔との間に、セパレータを挟み、円筒状に巻き取り、コンデンサ素子を準備した。
次いで、実施例1の導電性高分子溶液にコンデンサ中間体を含むコンデンサ素子を、浸漬した後、真空引きし、120℃の熱風乾燥機で乾燥し、コンデンサ中間体表面に固体電解質層を形成させた。
その後、アルミ製のケースに、上記コンデンサ素子と、電解液であるアジピン酸水素アンモニウム20%−エチレングリコール80%溶液を入れ、封口ゴムで封止して、電解コンデンサを作製した。
作製したコンデンサについて、120Hzでの静電容量、100kHzでのESRの初期値、150℃、1000時間後のESRを測定した。その結果を表2に示す。
(Example 6) Production of electrolytic capacitor After connecting an anode lead terminal to etched aluminum foil, it was formed in a 10% aqueous solution of ammonium adipate to form a dielectric oxide film on the surface to obtain a capacitor intermediate. .
Next, a separator was sandwiched between the opposing aluminum cathode foil to which the cathode lead terminal was welded and the anode foil, and wound into a cylindrical shape to prepare a capacitor element.
Next, after immersing the capacitor element containing the capacitor intermediate in the conductive polymer solution of Example 1, it was vacuumed and dried with a 120 ° C. hot air dryer to form a solid electrolyte layer on the surface of the capacitor intermediate. It was.
Thereafter, the above capacitor element and an electrolytic solution of 20% ammonium hydrogen adipate-80% ethylene glycol were placed in an aluminum case and sealed with a sealing rubber to produce an electrolytic capacitor.
For the produced capacitor, the electrostatic capacity at 120 Hz, the initial value of ESR at 100 kHz, and the ESR after 1000 hours at 150 ° C. were measured. The results are shown in Table 2.
(実施例7〜10)
導電性高分子溶液を表2に示すように変更したこと以外は実施例6と同様にしてコンデンサを作製し、評価した。その結果を表2に示す。
(Examples 7 to 10)
A capacitor was prepared and evaluated in the same manner as in Example 6 except that the conductive polymer solution was changed as shown in Table 2. The results are shown in Table 2.
(比較例1)
13.8g(0.1mol)の3,4−b−チエノチオフェンの代わりに、14.2g(0.1mol)のエチレンジオキシチオフェンを用いたこと以外は実施例1と同様にして、1.5質量%のポリスチレンスルホン酸ドープポリエチレンジオキシチオフェン溶液を得た。そして、実施例6と同様にして電解コンデンサを作製し、評価した。その結果を表2に示す。
(Comparative Example 1)
1. In the same manner as in Example 1 except that 14.2 g (0.1 mol) of ethylenedioxythiophene was used instead of 13.8 g (0.1 mol) of 3,4-b-thienothiophene. A 5% by mass polystyrenesulfonic acid-doped polyethylene dioxythiophene solution was obtained. Then, an electrolytic capacitor was produced and evaluated in the same manner as in Example 6. The results are shown in Table 2.
実施例1〜5の導電性高分子溶液を塗布して形成した固体電解質層をそれぞれ備えた実施例6〜10の電解コンデンサは、高容量であり、また、耐熱性に優れていた。一方、比較例1の電解コンデンサは耐熱性に劣っていた。 The electrolytic capacitors of Examples 6 to 10 each having a solid electrolyte layer formed by applying the conductive polymer solutions of Examples 1 to 5 had a high capacity and were excellent in heat resistance. On the other hand, the electrolytic capacitor of Comparative Example 1 was inferior in heat resistance.
10 電解コンデンサ
11 陽極
12 誘電体層
13 陰極
13a 固体電解質層
DESCRIPTION OF
Claims (5)
(化学式(1)におけるR1、R3は、それぞれ独立して、水素原子または炭素数1〜12のアルキル基であり、R2は置換されていてもよい炭素数1〜8のアルキレン基である。また、nは10以上の整数である。)
(R 1 and R 3 in chemical formula (1) are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and R 2 is an optionally substituted alkylene group having 1 to 8 carbon atoms. And n is an integer of 10 or more.)
前記導電性高分子溶液が、請求項3に記載の固体電解質を溶媒中に溶解又は分散した液であることを特徴とする電解コンデンサの製造方法。
A conductive polymer solution is applied to a dielectric layer side surface of a capacitor intermediate having an anode made of a porous body of valve metal and an oxide film dielectric layer formed by oxidizing the surface of the anode. An electrolytic capacitor manufacturing method for forming a solid electrolyte layer,
The method for producing an electrolytic capacitor, wherein the conductive polymer solution is a liquid obtained by dissolving or dispersing the solid electrolyte according to claim 3 in a solvent.
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