JP5417630B2 - 固体電解質用組成物およびそれを用いた太陽電池 - Google Patents
固体電解質用組成物およびそれを用いた太陽電池 Download PDFInfo
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- JP5417630B2 JP5417630B2 JP2011521936A JP2011521936A JP5417630B2 JP 5417630 B2 JP5417630 B2 JP 5417630B2 JP 2011521936 A JP2011521936 A JP 2011521936A JP 2011521936 A JP2011521936 A JP 2011521936A JP 5417630 B2 JP5417630 B2 JP 5417630B2
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- 239000000203 mixture Substances 0.000 title claims description 155
- 239000007784 solid electrolyte Substances 0.000 title claims description 46
- 239000000178 monomer Substances 0.000 claims description 400
- 229920000642 polymer Polymers 0.000 claims description 182
- 150000001875 compounds Chemical class 0.000 claims description 135
- 239000002904 solvent Substances 0.000 claims description 123
- 229920000547 conjugated polymer Polymers 0.000 claims description 109
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000003792 electrolyte Substances 0.000 claims description 46
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 38
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 24
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 21
- 230000000379 polymerizing effect Effects 0.000 claims description 20
- 238000012546 transfer Methods 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 239000003575 carbonaceous material Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000002041 carbon nanotube Substances 0.000 claims description 10
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 10
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 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 claims description 6
- 239000006229 carbon black Substances 0.000 claims description 6
- 229910003472 fullerene Inorganic materials 0.000 claims description 6
- 229910002804 graphite Inorganic materials 0.000 claims description 5
- 239000010439 graphite Substances 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 134
- -1 iodine anions Chemical class 0.000 description 79
- 239000000243 solution Substances 0.000 description 77
- 238000006116 polymerization reaction Methods 0.000 description 56
- 150000002500 ions Chemical class 0.000 description 45
- 150000008040 ionic compounds Chemical class 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000975 dye Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- 229910044991 metal oxide Inorganic materials 0.000 description 30
- 150000004706 metal oxides Chemical class 0.000 description 30
- 239000003505 polymerization initiator Substances 0.000 description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 229920001940 conductive polymer Polymers 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920000767 polyaniline Polymers 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 125000002091 cationic group Chemical group 0.000 description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 12
- 238000012719 thermal polymerization Methods 0.000 description 12
- 239000002841 Lewis acid Substances 0.000 description 11
- 150000007517 lewis acids Chemical class 0.000 description 11
- 230000002776 aggregation Effects 0.000 description 10
- 238000004220 aggregation Methods 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 238000012662 bulk polymerization Methods 0.000 description 9
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000005456 alcohol based solvent Substances 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- 239000005453 ketone based solvent Substances 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910010413 TiO 2 Inorganic materials 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 7
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 7
- 229910001887 tin oxide Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 6
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 6
- 239000003759 ester based solvent Substances 0.000 description 6
- 229940116333 ethyl lactate Drugs 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 229940057867 methyl lactate Drugs 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 229920000123 polythiophene Polymers 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229910000510 noble metal Inorganic materials 0.000 description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(O)COCCO ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 0.000 description 4
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 4
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 4
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 4
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 4
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000006104 solid solution Substances 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- UPPUJFRSINZXTE-UHFFFAOYSA-N (2,2,3,3,4-pentamethylpiperidin-1-yl) 2-methylprop-2-enoate Chemical compound CC1CCN(OC(=O)C(C)=C)C(C)(C)C1(C)C UPPUJFRSINZXTE-UHFFFAOYSA-N 0.000 description 3
- OWWXMYJVBWPIJA-UHFFFAOYSA-N 1-ethenyl-9-ethylcarbazole Chemical compound C1=CC(C=C)=C2N(CC)C3=CC=CC=C3C2=C1 OWWXMYJVBWPIJA-UHFFFAOYSA-N 0.000 description 3
- YWYRVWBEIODDTJ-UHFFFAOYSA-N 1-ethenyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(C=C)=CC=C2 YWYRVWBEIODDTJ-UHFFFAOYSA-N 0.000 description 3
- IVCMUVGRRDWTDK-UHFFFAOYSA-M 1-methyl-3-propylimidazol-1-ium;iodide Chemical compound [I-].CCCN1C=C[N+](C)=C1 IVCMUVGRRDWTDK-UHFFFAOYSA-M 0.000 description 3
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 3
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- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940006186 sodium polystyrene sulfonate Drugs 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08J5/20—Manufacture of shaped structures of ion-exchange resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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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
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
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Description
上記モノマー(a)中、上記スルホン酸基またはスルホン酸塩基を有するモノマー(a−1)が4mol%以下の量で含まれていることを特徴とする[2]または[3]に記載の固体電解質用組成物。
[7]上記キレート能を有するモノマー(a−2)が、ピリジル基またはフェナントロリン構造を有するモノマーであるか、あるいは、下記式(IV)で表される基または下記式(V)で表される基を有するモノマーであることを特徴とする[2]〜[6]のいずれかに記載の固体電解質用組成物。
[8]上記高分子化合物(A)が、上記キレート能を有するモノマー(a−2)とスルホン酸基またはスルホン酸塩基を有するモノマー(a−1)とを重合して得られる高分子化合物であり、
上記電荷移動性材料が、π共役系高分子(β)であり、
上記固体電解質用組成物が、上記高分子化合物(A)および酸化剤の存在下で、電解性基質溶媒中、モノマーを重合して上記π共役系高分子(β)を生成させるとともに、上記高分子化合物(A)を上記π共役系高分子(β)にドープさせて得られることを特徴とする[2]に記載の固体電解質用組成物。
[11]上記キレート能を有するモノマー(a−2)が、ピリジル基またはフェナントロリン構造を有するモノマーであるか、あるいは、下記式(IV)で表される基または下記式(V)で表される基を有するモノマーであることを特徴とする[7]〜[10]のいずれかに記載の固体電解質用組成物。
[12][1]〜[11]のいずれかに記載の固体電解質用組成物を用いた太陽電池用電荷輸送材。
態様1の固体電解質用組成物は、高分子化合物(A)と、炭素材料とを含む。なお、本明細書において「態様1の固体電解質用組成物」を単に「態様1の組成物」ともいう。高分子化合物(A)は、キレート能を有するモノマー(a−2)を含むモノマー(a)を重合して得られる。このような態様1の組成物を溶剤に配合すると、通常組成物が均一に分散した溶液を形成する。さらに該組成物をイオン性化合物ととともに溶剤に配合した場合は、イオン対との相互作用が比較的弱いため、凝集し難い。すなわち、態様1の固体電解質用組成物から得られる溶液は、高い安定性を有する。
態様2の固体電解質用組成物は、高分子化合物(A)と、π共役系高分子(β)とを含む。なお、本明細書において「態様2の固体電解質用組成物」を単に「態様2の組成物」ともいう。高分子化合物(A)は、キレート能を有するモノマー(a−2)を含むモノマー(a)を重合して得られる。このような態様2の組成物を溶剤に配合すると、通常組成物が均一に溶解または分散した溶液を形成する。さらに該組成物をイオン性化合物とともに溶剤に配合した場合は、イオン対との相互作用が比較的弱いため、凝集し難い。すなわち、態様2の固体電解質用組成物から得られる溶液は、高い安定性を有する。
態様3の組成物は、高分子化合物(A)とπ共役系高分子(β)とを含む。いいかえると、態様3の組成物は、高分子化合物(A)をπ共役系高分子(β)にドープさせて得られる組成物である。なお、本明細書において、「高分子化合物(A)をπ共役系高分子(β)にドープさせて得られる組成物」を、単に「高分子化合物(A)がドープされたπ共役系高分子(β)」または「ドープ済みπ共役系高分子(β)」ともいう。
態様1の組成物において、さらにπ共役系高分子(β)を配合してもよい。この場合、π共役系高分子(β)は、高分子化合物(A)100重量部に対し、0.1〜600重量部程度加えることが好ましい。
下記条件でのGPCにより測定した。
カラム:GF−1G7B+GF−510HQ(Asahipak:登録商標、
昭和電工(株)製)
基準物質:ポリスチレンおよびポリスチレンスルホン酸ナトリウム
サンプル濃度:1.0mg/ml
溶離液:50ミリモル塩化リチウム水溶液/CH3CN=60/40wt
流量:0.6ml/min
カラム温度:30℃
検出器:UV254nm
〔製造例1−1〕
撹拌機、窒素ガス導入管、環流冷却器、投入口および温度計を備えた容量1000cm3の四つ口フラスコに、2−ソジウムスルホエチルメタクリレート(MS−2N)を24.3g(25モル%)、アセトアセトキシエチルメタクリレート(AAEM)を25.7g(15モル%)、ベンジルメタクリレート(BzMA)を42.8g(30モル%)、2−エチルヘキシルメタクリレート(2EHMA)を48.2g(30モル%)、イオン交換水を150g、イソプロピルアルコール(IPA)を300g投入した。フラスコ内に窒素ガスを導入しながら、フラスコ内の混合物を70℃まで昇温した。次いで、アゾビスイソブチロニトリルを0.7gフラスコ内に投入し、70℃を保ち、18時間重合反応を行って高分子化合物(A)を含むポリマー溶液(A−1)を得た。
モノマーを表1−1に示すモノマーに代え、重合条件を表1−2に示す条件に代えた以外は製造例1−1と同様にして、高分子化合物(AP−2)〜(AP−14)を得た。また、高分子化合物(AP−2)〜(AP−14)のMwを表1−1に示す。なお、表1−1、1−2には製造例1−1についても示した。
NaSS:スチレンスルホン酸ナトリウム
AAEM:アセトアセトキシエチルメタクリレート
PME-100:メトキシジエチレングリコールメタクリレート
BzMA:ベンジルメタクリレート
2EHMA:2−エチルヘキシルメタクリレート
CHMA:シクロヘキシルメタクリレート
HEMA:2−ヒドロキシエチルメタクリレート
なお、表1−2、開始剤の欄におけるカッコ内の数値は、開始剤の量を表す。
撹拌機、窒素ガス導入管、環流冷却器、投入口および温度計を備えた容量1000cm3の四つ口フラスコに、製造例1で得られた高分子化合物(AP−1)を27.8g、イオン交換水を500g、35%塩酸水溶液を6g投入し、60℃に加熱して3時間撹拌を行った後、25℃まで冷却した。フラスコ内の溶液は、均一透明なものであった。
表1−3の条件に代えた以外は、実施例1に示した方法により組成物(E−2)〜(E−7)(態様3の組成物)を調製した。表1−3中には、実施例1についても含めて、組成物のモノマー組成、使用高分子化合物(A)種およびその量、使用塩酸量、使用酸化剤およびその量並びに反応条件(反応温度および反応時間)を示した。
表1−3の条件に代えた以外は、実施例1に示した方法により組成物(EC−4)、(EC−5)、(EC−7)を調製した。
表1−4の条件に代えた以外は、実施例1に示した方法により高分子(β−9)、(β−10)、(βC−3)を調製した。
P−TS:p−トルエンスルホン酸
[実施例9]
実施例9では、製造例9’で得た高分子(β−9)30重量部と製造例7で得た高分子化合物(AP−7)70重量部とを混合し、態様2の組成物を得た(表2−1)。
表2−1に記載した高分子(β)、高分子化合物(A)に代えた他は、実施例9と同様にして、態様2の組成物を得た。
実施例8では、カーボンナノチューブ(CNT)20重量部と製造例7で得た高分子化合物(AP−7)80重量部とを混合し、態様1の組成物を得た(表2−1)。
表2−1に記載した炭素材料、高分子化合物(A)に代えた他は、実施例10と同様にして、態様1の組成物を得た。
参考例8では、アルミ粉末30重量部と製造例7で得た高分子化合物(AP−7)70重量部とを混合し、組成物を得た(表2−1)。
CNT:カーボンナノチューブ
CB:カーボンブラック D149:(三菱製紙社製)
MK-2:(綜研化学社製)
N719:(ソーラロニクス社製)
表2−2は表2−1の続きである。
(溶剤への溶解性)
実施例および参考例で作製した乾燥導電性ポリマーを溶剤(アニリン、アニシジンを用いた場合についてはトルエン、PEDOTを用いた場合についてはプロピレングリコールモノメチルエーテル、その他を用いた場合についてはMEK)中に溶解した時の溶解状態を目視で確認した。より具体的には、配合形態が混合である時は、高分子化合物(A)及びカーボン等を分散した状態を、ドープ済みπ共役系高分子(β)の場合は前記導電性高分子を溶剤に溶解した後、溶解(分散)状態を目視で確認した。
(1)溶剤(MEK)に溶解した高分子化合物(A)に全固形分が5%となる様に、カーボン等(CB、CNT、フラーレン、不溶性導電性ポリマー)を表2−1の配合で混合した溶液を作製した。
上記イオン対添加・混合後の溶液をガラス基板上にポッティングして100℃×10分乾燥した後の目視による均一性の確認を行った。
(1)TiO2スパッタを行ったFTOガラス基板上にソーラロニクス社製T/SPを約5μmdry(面積5mm2)で塗工した後、500℃で30分焼成を行った。
表2−2に、初期および2日後の結果を示す。
Claims (14)
- 高分子化合物(A)と電荷移動性材料とを含み、前記高分子化合物(A)が、キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)および、スルホン酸基またはスルホン酸塩基と、重合性ビニル基とを有するモノマー(a−1)とを含むモノマー(a)を重合して得られる高分子化合物であることを特徴とする固体電解質用組成物。
- 前記電荷移動性材料が、炭素材料および/またはπ共役系高分子(β)であることを特徴とする請求項1に記載の固体電解質用組成物。
- 前記モノマー(a)中、前記キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)が30mol%以上の量で含まれていることを特徴とする請求項2に記載の固体電解質用組成物。
- 前記モノマー(a)中、前記スルホン酸基またはスルホン酸塩基と、重合性ビニル基とを有するモノマー(a−1)が4mol%以下の量で含まれていることを特徴とする請求項2または3に記載の固体電解質用組成物。
- 前記炭素材料が、グラファイト、カーボンブラック、フラーレンおよびカーボンナノチューブから選ばれる少なくとも一種であることを特徴とする請求項2〜4のいずれかに記載の固体電解質用組成物。
- 前記キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)が、ピリジル基またはフェナントロリン構造を有するモノマーであることを特徴とする請求項2〜6のいずれかに記載の固体電解質用組成物。
- 前記高分子化合物(A)が、前記キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)とスルホン酸基またはスルホン酸塩基と、重合性ビニル基とを有するモノマー(a−1)とを重合して得られる高分子化合物であり、
前記電荷移動性材料が、π共役系高分子(β)であり、
前記固体電解質用組成物が、前記高分子化合物(A)および酸化剤の存在下で、電解性基質溶媒中、モノマーを重合して前記π共役系高分子(β)を生成させるとともに、前記高分子化合物(A)を前記π共役系高分子(β)にドープさせて得られることを特徴とする請求項2に記載の固体電解質用組成物。 - 前記高分子化合物(A)が、前記スルホン酸基またはスルホン酸塩基と、重合性ビニル基とを有するモノマー(a−1)10〜50mol%と、前記キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)10〜90mol%と、その他のモノマー(a−3)0〜70mol%とを重合して得られる高分子化合物であり(ここで、モノマー(a−1)〜(a−3)の合計量を100mol%とする。)、
前記その他のモノマー(a−3)が、親水性基と重合性ビニル基とを有するモノマー(a−3−1)、芳香族基または脂環族基と重合性ビニル基とを有するモノマー(a−3−2)およびアルキル基と重合性ビニル基とを有するモノマー(a−3−3)からなる群から選ばれる少なくとも1種であることを特徴とする請求項9に記載の固体電解質用組成物。 - 前記キレート能を有する基と重合性ビニル基とを有するモノマー(a−2)が、ピリジル基またはフェナントロリン構造を有するモノマーであることを特徴とする請求項9〜11のいずれかに記載の固体電解質用組成物。
- 請求項1〜13のいずれかに記載の固体電解質用組成物を用いた太陽電池用電荷輸送材。
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