JP6555467B2 - 電解液 - Google Patents
電解液 Download PDFInfo
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- JP6555467B2 JP6555467B2 JP2015047042A JP2015047042A JP6555467B2 JP 6555467 B2 JP6555467 B2 JP 6555467B2 JP 2015047042 A JP2015047042 A JP 2015047042A JP 2015047042 A JP2015047042 A JP 2015047042A JP 6555467 B2 JP6555467 B2 JP 6555467B2
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- substituent
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- secondary battery
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- 239000003792 electrolyte Substances 0.000 title claims description 31
- 239000008151 electrolyte solution Substances 0.000 claims description 165
- 125000001424 substituent group Chemical group 0.000 claims description 120
- 229910052751 metal Inorganic materials 0.000 claims description 92
- 239000002184 metal Substances 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 83
- 239000000126 substance Substances 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- -1 C = O Inorganic materials 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052782 aluminium Inorganic materials 0.000 claims description 27
- 239000007774 positive electrode material Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 150000001768 cations Chemical class 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 150000005678 chain carbonates Chemical class 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052596 spinel Inorganic materials 0.000 claims description 7
- 239000011029 spinel Substances 0.000 claims description 7
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 82
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 63
- 229910001416 lithium ion Inorganic materials 0.000 description 63
- 239000003960 organic solvent Substances 0.000 description 52
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 41
- 238000004090 dissolution Methods 0.000 description 33
- 229910002804 graphite Inorganic materials 0.000 description 32
- 239000010439 graphite Substances 0.000 description 31
- 239000007773 negative electrode material Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 22
- 238000003756 stirring Methods 0.000 description 19
- 239000011230 binding agent Substances 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 18
- 238000007599 discharging Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 239000011888 foil Substances 0.000 description 16
- 238000003860 storage Methods 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000003575 carbonaceous material Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
- 239000000919 ceramic Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000003990 capacitor Substances 0.000 description 10
- GBPVMEKUJUKTBA-UHFFFAOYSA-N methyl 2,2,2-trifluoroethyl carbonate Chemical compound COC(=O)OCC(F)(F)F GBPVMEKUJUKTBA-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 239000011149 active material Substances 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 9
- 239000000956 alloy Substances 0.000 description 9
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000011135 tin Substances 0.000 description 9
- 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 8
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 229910052718 tin Inorganic materials 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000002800 charge carrier Substances 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910003002 lithium salt Inorganic materials 0.000 description 7
- 159000000002 lithium salts Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910013870 LiPF 6 Inorganic materials 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000001237 Raman spectrum Methods 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000004676 glycans Chemical class 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 229920001282 polysaccharide Polymers 0.000 description 5
- 239000005017 polysaccharide Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 5
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 238000001845 vibrational spectrum Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- 229910000838 Al alloy Inorganic materials 0.000 description 4
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 4
- 239000002033 PVDF binder Substances 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000004584 polyacrylic acid Substances 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920008712 Copo Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910002099 LiNi0.5Mn1.5O4 Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000005275 alloying Methods 0.000 description 3
- 229910021383 artificial graphite Inorganic materials 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
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- 150000005676 cyclic carbonates Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 239000002241 glass-ceramic Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
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- 239000010931 gold Substances 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
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- 229910052750 molybdenum Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910021382 natural graphite Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
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- 238000010248 power generation Methods 0.000 description 3
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- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 150000003624 transition metals Chemical class 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
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- 229910018461 Al—Mn Inorganic materials 0.000 description 2
- 229920000856 Amylose Polymers 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910020646 Co-Sn Inorganic materials 0.000 description 2
- 229910020709 Co—Sn Inorganic materials 0.000 description 2
- 229910017755 Cu-Sn Inorganic materials 0.000 description 2
- 229910017927 Cu—Sn Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 229910011281 LiCoPO 4 Inorganic materials 0.000 description 2
- 229910010707 LiFePO 4 Inorganic materials 0.000 description 2
- 229910013275 LiMPO Inorganic materials 0.000 description 2
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
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- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000002460 vibrational spectroscopy Methods 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910009161 xLi2S-(1-x)P2S5 Inorganic materials 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
下記一般式(1−1)で表される鎖状カーボネート、下記一般式(1−2)で表されるエステル、又は、下記一般式(1−3)で表されるリン酸エステルが、
アルカリ金属、アルカリ土類金属又はアルミニウムをカチオンとし、下記一般式(2)で表される化学構造をアニオンとする金属塩に対し、
モル比1〜3で含まれること特徴とする。
R12COOR13 一般式(1−2)
OP(OR14)(OR15)(OR16) 一般式(1−3)
(R10、R11、R12、R13、R14、R15、R16は、それぞれ独立に、鎖状アルキルであるCnHaFbClcBrdIe、又は、環状アルキルを化学構造に含むCmHfFgClhBriIjのいずれかから選択される。nは1以上の整数、mは3以上の整数、a、b、c、d、e、f、g、h、i、jはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+e、2m−1=f+g+h+i+jを満たす。
ただし、R10若しくはR11はb≧1若しくはg≧1、R12若しくはR13はb≧1若しくはg≧1、R14、R15若しくはR16はb≧1若しくはg≧1を満たす。)
(R21は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
R22は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
また、R21とR22は、互いに結合して環を形成しても良い。
X21は、SO2、C=O、C=S、RaP=O、RbP=S、S=O、Si=Oから選択される。
Ra、Rbは、それぞれ独立に、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、OH、SH、CN、SCN、OCNから選択される。
また、Ra、Rbは、R21又はR22と結合して環を形成しても良い。)
下記一般式(1−1)で表される鎖状カーボネート、下記一般式(1−2)で表されるエステル、又は、下記一般式(1−3)で表されるリン酸エステルが、
アルカリ金属、アルカリ土類金属又はアルミニウムをカチオンとし、下記一般式(2)で表される化学構造をアニオンとする金属塩に対し、
モル比1〜3で含まれること特徴とする。
R12COOR13 一般式(1−2)
OP(OR14)(OR15)(OR16) 一般式(1−3)
(R10、R11、R12、R13、R14、R15、R16は、それぞれ独立に、鎖状アルキルであるCnHaFbClcBrdIe、又は、環状アルキルを化学構造に含むCmHfFgClhBriIjのいずれかから選択される。nは1以上の整数、mは3以上の整数、a、b、c、d、e、f、g、h、i、jはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+e、2m−1=f+g+h+i+jを満たす。
ただし、R10若しくはR11はb≧1若しくはg≧1、R12若しくはR13はb≧1若しくはg≧1、R14、R15若しくはR16はb≧1若しくはg≧1を満たす。)
(R21は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
R22は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
また、R21とR22は、互いに結合して環を形成しても良い。
X21は、SO2、C=O、C=S、RaP=O、RbP=S、S=O、Si=Oから選択される。
Ra、Rbは、それぞれ独立に、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、OH、SH、CN、SCN、OCNから選択される。
また、Ra、Rbは、R21又はR22と結合して環を形成しても良い。)
(R23、R24は、それぞれ独立に、CnHaFbClcBrdIe(CN)f(SCN)g(OCN)hである。
n、a、b、c、d、e、f、g、hはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+e+f+g+hを満たす。
また、R23とR24は、互いに結合して環を形成しても良く、その場合は、2n=a+b+c+d+e+f+g+hを満たす。
X22は、SO2、C=O、C=S、RcP=O、RdP=S、S=O、Si=Oから選択される。
Rc、Rdは、それぞれ独立に、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、OH、SH、CN、SCN、OCNから選択される。
また、Rc、Rdは、R23又はR24と結合して環を形成しても良い。)
(R25、R26は、それぞれ独立に、CnHaFbClcBrdIeである。
n、a、b、c、d、eはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+eを満たす。
また、R25とR26は、互いに結合して環を形成しても良く、その場合は、2n=a+b+c+d+eを満たす。)
また後述の通り、本発明の電解液を具備する二次電池は、電極/電解液界面に、低抵抗かつカチオン含有率の高いSEI皮膜を金属塩由来物で形成することで、電極/電解液界面において可逆的かつ高速な反応を可能にすると考えられる。
ここで、
L:結晶子の大きさ
λ:入射X線波長(1.54Å)
β:ピークの半値幅(ラジアン)
θ:回折角
なお、上記したSiOxにおいては、リチウムイオン二次電池の充放電時にリチウムとSi相のケイ素とによる合金化反応が生じると考えられている。そして、この合金化反応がリチウムイオン二次電池の充放電に寄与すると考えられている。後述するスズを含む負極活物質についても、同様に、スズとリチウムとの合金化反応によって充放電できると考えられている。
一般式(1−1)で表される鎖状カーボネートである2,2,2−トリフルオロエチルメチルカーボネートに金属塩である(FSO2)2NLiを還流条件下で溶解させて、実施例1−1の電解液を製造した。実施例1−1の電解液においては、2,2,2−トリフルオロエチルメチルカーボネートが、(FSO2)2NLiに対し、モル比1.5で含まれる。
一般式(1−1)で表される鎖状カーボネートである2,2,2−トリフルオロエチルメチルカーボネートとフッ素化されていない鎖状カーボネートであるジメチルカーボネートの混合溶媒に金属塩である(FSO2)2NLiを還流条件下で溶解させて、実施例1−2の電解液を製造した。実施例1−2の電解液においては、2,2,2−トリフルオロエチルメチルカーボネートとジメチルカーボネートをあわせたものが、(FSO2)2NLiに対し、モル比1.6で含まれており、2,2,2−トリフルオロエチルメチルカーボネートが(FSO2)2NLiに対しモル比1.3で含まれる。
一般式(1−1)で表される鎖状カーボネートである2,2,2−トリフルオロエチルメチルカーボネートとフッ素化されていない鎖状カーボネートであるエチルメチルカーボネートの混合溶媒に金属塩である(FSO2)2NLiを還流条件下で溶解させて、実施例1−3の電解液を製造した。実施例1−3の電解液においては、2,2,2−トリフルオロエチルメチルカーボネートとエチルメチルカーボネートをあわせたものが、(FSO2)2NLiに対し、モル比1.6で含まれており、2,2,2−トリフルオロエチルメチルカーボネートが(FSO2)2NLiに対しモル比1.3で含まれる。
フッ素置換したエチレンカーボネート3体積部並びに低粘度溶媒としてエチルメチルカーボネート及びフッ素化した鎖状化合物の混合液7体積部を混合した混合溶媒に、電解質であるLiPF6を溶解させて、LiPF6の濃度が1.0mol/Lである比較例1−1の電解液を製造した。比較例1−1の電解液においては、上記混合溶媒がLiPF6に対し、概ねモル比10で含まれる。なお、上記フッ素化した鎖状化合物は、一般式(1−1)で表される鎖状カーボネート、一般式(1−2)で表されるエステル、一般式(1−3)で表されるリン酸エステルのいずれにも該当しない、常温で液体の化合物である。
実施例1−1の電解液を用いた実施例Iのリチウムイオン二次電池を以下のとおり製造した。
電解液として実施例1−2の電解液を用いた以外は、実施例Iと同様の方法で、実施例IIのリチウムイオン二次電池を得た。
電解液として実施例1−3の電解液を用いた以外は、実施例Iと同様の方法で、実施例IIIのリチウムイオン二次電池を得た。
電解液として比較例1−1の電解液を用いた以外は、実施例Iと同様の方法で、比較例Iのリチウムイオン二次電池を得た。
実施例I〜III、比較例Iのリチウムイオン二次電池につき、以下の方法で、容量維持率を評価した。
各リチウムイオン二次電池について、室温、3.0V〜4.9V(vs.Li基準)の範囲でCC充放電を繰り返した。初回充放電時の放電容量、各サイクル時の放電容量を測定した。そして、初回充放電時の各リチウムイオン二次電池の容量を100%として、特定のサイクル時の各リチウムイオン二次電池の容量維持率(%)を算出した。結果を表1に示す。また、図1に、実施例Iのリチウムイオン二次電池における、初回充放電時、50サイクル時、及び、100サイクル時の充放電曲線を重ねて示す。図2に、実施例IIのリチウムイオン二次電池における、初回充放電時、10サイクル時、20サイクル時、及び、50サイクル時の充放電曲線を重ねて示す。図3に、実施例IIIのリチウムイオン二次電池における、初回充放電時、10サイクル時、20サイクル時、及び、50サイクル時の充放電曲線を重ねて示す。図4に、比較例Iのリチウムイオン二次電池における、初回充放電時、10サイクル時、及び、20サイクル時の充放電曲線を重ねて示す。
Claims (10)
- 下記一般式(1−1)で表される鎖状カーボネート、又は、下記一般式(1−2)で表されるエステルが、
アルカリ金属、アルカリ土類金属又はアルミニウムをカチオンとし、下記一般式(2)で表される化学構造をアニオンとする金属塩に対し、
モル比1〜3で含まれ、
下記一般式(1−1)で表される鎖状カーボネート、又は、下記一般式(1−2)で表されるエステルが、電解液に含まれる全溶媒に対して、50体積%以上で含まれることを特徴とする電解液を具備し、
反応電位がLi基準で4.5V以上である正極活物質を具備する、二次電池。
R10OCOOR11 一般式(1−1)
R12COOR13 一般式(1−2)
(R10、R11、R12、R13は、それぞれ独立に、鎖状アルキルであるCnHaFbClcBrdIe、又は、環状アルキルを化学構造に含むCmHfFgClhBriIjのいずれかから選択される。nは1以上の整数、mは3以上の整数、a、b、c、d、e、f、g、h、i、jはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+e、2m−1=f+g+h+i+jを満たす。
ただし、R10若しくはR11はb≧1若しくはg≧1、R12若しくはR13はb≧1若しくはg≧1を満たす。)
(R21X21)(R22SO2)N 一般式(2)
(R21は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
R22は、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、CN、SCN、OCNから選択される。
また、R21とR22は、互いに結合して環を形成しても良い。
X21は、SO2、C=O、C=S、RaP=O、RbP=S、S=O、Si=Oから選択される。
Ra、Rbは、それぞれ独立に、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、OH、SH、CN、SCN、OCNから選択される。
また、Ra、Rbは、R21又はR22と結合して環を形成しても良い。) - 前記R10、R11、R12、R13が以下のとおりである請求項1に記載の二次電池。
(R10、R11、R12、R13は、それぞれ独立に、鎖状アルキルであるCnHaFb、又は、環状アルキルを化学構造に含むCmHfFgのいずれかから選択される。nは1以上の整数、mは3以上の整数、a、b、f、gはそれぞれ独立に0以上の整数であり、2n+1=a+b、2m−1=f+gを満たす。
ただし、R10若しくはR11はb≧1若しくはg≧1、R12若しくはR13はb≧1若しくはg≧1を満たす。) - 前記一般式(1−1)又は一般式(1−2)に関するnが1以上6以下の整数であり、mが3以上8以下の整数である請求項1又は2に記載の二次電池。
- 前記金属塩のアニオンの化学構造が下記一般式(2−1)で表される請求項1〜3のいずれか1項に記載の二次電池。
(R23X22)(R24SO2)N 一般式(2−1)
(R23、R24は、それぞれ独立に、CnHaFbClcBrdIe(CN)f(SCN)g(OCN)hである。
n、a、b、c、d、e、f、g、hはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+e+f+g+hを満たす。
また、R23とR24は、互いに結合して環を形成しても良く、その場合は、2n=a+b+c+d+e+f+g+hを満たす。
X22は、SO2、C=O、C=S、RcP=O、RdP=S、S=O、Si=Oから選択される。
Rc、Rdは、それぞれ独立に、水素、ハロゲン、置換基で置換されていても良いアルキル基、置換基で置換されていても良いシクロアルキル基、置換基で置換されていても良い不飽和アルキル基、置換基で置換されていても良い不飽和シクロアルキル基、置換基で置換されていても良い芳香族基、置換基で置換されていても良い複素環基、置換基で置換されていても良いアルコキシ基、置換基で置換されていても良い不飽和アルコキシ基、置換基で置換されていても良いチオアルコキシ基、置換基で置換されていても良い不飽和チオアルコキシ基、OH、SH、CN、SCN、OCNから選択される。
また、Rc、Rdは、R23又はR24と結合して環を形成しても良い。) - 前記金属塩のアニオンの化学構造が下記一般式(2−2)で表される請求項1〜4のいずれか1項に記載の二次電池。
(R25SO2)(R26SO2)N 一般式(2−2)
(R25、R26は、それぞれ独立に、CnHaFbClcBrdIeである。
n、a、b、c、d、eはそれぞれ独立に0以上の整数であり、2n+1=a+b+c+d+eを満たす。
また、R25とR26は、互いに結合して環を形成しても良く、その場合は、2n=a+b+c+d+eを満たす。) - 前記一般式(2−1)に関するnが0〜6の整数であり、前記一般式(2−1)のR23とR24 が結合して環を形成している場合にはnが1〜8の整数である請求項4に記載の二次電池。
- 前記一般式(2−2)に関するnが0〜6の整数であり、前記一般式(2−2)のR25とR26が結合して環を形成している場合にはnが1〜8の整数である請求項5に記載の二次電池。
- 前記電解液の前記モル比が1.2〜2.5の範囲内である請求項1〜7のいずれか1項に記載の二次電池。
- 正極活物質としてスピネル構造の金属酸化物を具備する請求項1〜8のいずれか1項に記載の二次電池。
- アルミニウム製の正極集電体を具備する請求項1〜9のいずれか1項に記載の二次電池。
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