JP6989805B2 - 電解液、電気化学デバイス、リチウムイオン二次電池、及び、モジュール - Google Patents
電解液、電気化学デバイス、リチウムイオン二次電池、及び、モジュール Download PDFInfo
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- JP6989805B2 JP6989805B2 JP2020074679A JP2020074679A JP6989805B2 JP 6989805 B2 JP6989805 B2 JP 6989805B2 JP 2020074679 A JP2020074679 A JP 2020074679A JP 2020074679 A JP2020074679 A JP 2020074679A JP 6989805 B2 JP6989805 B2 JP 6989805B2
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims description 73
- 229910001416 lithium ion Inorganic materials 0.000 title claims description 38
- 239000003792 electrolyte Substances 0.000 title description 27
- 150000001875 compounds Chemical class 0.000 claims description 175
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 239000008151 electrolyte solution Substances 0.000 claims description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 239000002904 solvent Substances 0.000 claims description 58
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 description 106
- 229910052731 fluorine Inorganic materials 0.000 description 93
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
- 239000000243 solution Substances 0.000 description 80
- 229910052751 metal Inorganic materials 0.000 description 78
- -1 perfluoroalkyl iodide Chemical compound 0.000 description 77
- 239000002184 metal Substances 0.000 description 73
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 72
- 150000005676 cyclic carbonates Chemical class 0.000 description 69
- 238000000034 method Methods 0.000 description 65
- 239000010410 layer Substances 0.000 description 64
- 239000011737 fluorine Substances 0.000 description 60
- 235000002639 sodium chloride Nutrition 0.000 description 60
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 59
- 150000003839 salts Chemical class 0.000 description 51
- 239000007774 positive electrode material Substances 0.000 description 49
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 239000000203 mixture Substances 0.000 description 46
- 229920006395 saturated elastomer Polymers 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 125000001153 fluoro group Chemical group F* 0.000 description 38
- 239000003960 organic solvent Substances 0.000 description 36
- 239000000126 substance Substances 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 31
- 239000007773 negative electrode material Substances 0.000 description 29
- 239000002585 base Substances 0.000 description 28
- 239000007788 liquid Substances 0.000 description 28
- 239000011230 binding agent Substances 0.000 description 27
- 229910052744 lithium Inorganic materials 0.000 description 26
- 239000003575 carbonaceous material Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000000746 purification Methods 0.000 description 24
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 23
- 230000007423 decrease Effects 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 239000003990 capacitor Substances 0.000 description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- 150000005678 chain carbonates Chemical class 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 17
- 229910052782 aluminium Inorganic materials 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 238000007254 oxidation reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 239000002131 composite material Substances 0.000 description 16
- 239000002274 desiccant Substances 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 16
- 238000010791 quenching Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000010949 copper Substances 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 229910013872 LiPF Inorganic materials 0.000 description 14
- 101150058243 Lipf gene Proteins 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 229910052802 copper Inorganic materials 0.000 description 14
- 150000002170 ethers Chemical class 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 13
- 239000004020 conductor Substances 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000002562 thickening agent Substances 0.000 description 12
- 239000010936 titanium Substances 0.000 description 12
- 229910052725 zinc Inorganic materials 0.000 description 12
- 239000011701 zinc Substances 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 239000000956 alloy Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000006229 carbon black Substances 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 238000000859 sublimation Methods 0.000 description 11
- 230000008022 sublimation Effects 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
- 239000011149 active material Substances 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 10
- 230000002140 halogenating effect Effects 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 239000011135 tin Substances 0.000 description 10
- 229910052718 tin Inorganic materials 0.000 description 10
- 229910052719 titanium Inorganic materials 0.000 description 10
- 229910052723 transition metal Inorganic materials 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 229910003002 lithium salt Inorganic materials 0.000 description 9
- 229910052759 nickel Inorganic materials 0.000 description 9
- 239000011164 primary particle Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 150000003624 transition metals Chemical class 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- HFCSXCKLARAMIQ-UHFFFAOYSA-L disodium;sulfate;hydrate Chemical compound O.[Na+].[Na+].[O-]S([O-])(=O)=O HFCSXCKLARAMIQ-UHFFFAOYSA-L 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 159000000002 lithium salts Chemical class 0.000 description 8
- 239000010446 mirabilite Substances 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 8
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 8
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 229910021383 artificial graphite Inorganic materials 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
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- 239000011777 magnesium Substances 0.000 description 7
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- UUCOBUVUSYHNAX-UHFFFAOYSA-N 4-bromo-1,3-dioxol-2-one Chemical compound BrC1=COC(=O)O1 UUCOBUVUSYHNAX-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
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- 239000010439 graphite Substances 0.000 description 6
- 230000001771 impaired effect Effects 0.000 description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
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- 238000001953 recrystallisation Methods 0.000 description 6
- 238000000638 solvent extraction Methods 0.000 description 6
- 125000003003 spiro group Chemical group 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
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- 239000002033 PVDF binder Substances 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 229910052733 gallium Inorganic materials 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910001386 lithium phosphate Inorganic materials 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000002905 metal composite material Substances 0.000 description 5
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 5
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 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
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910000733 Li alloy Inorganic materials 0.000 description 4
- 229910013075 LiBF Inorganic materials 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 4
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 4
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
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- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
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- BXHHZLMBMOBPEH-UHFFFAOYSA-N diethyl-(2-methoxyethyl)-methylazanium Chemical class CC[N+](C)(CC)CCOC BXHHZLMBMOBPEH-UHFFFAOYSA-N 0.000 description 2
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- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
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- DEUISMFZZMAAOJ-UHFFFAOYSA-N lithium dihydrogen borate oxalic acid Chemical compound B([O-])(O)O.C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.[Li+] DEUISMFZZMAAOJ-UHFFFAOYSA-N 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
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- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- NDZWKTKXYOWZML-UHFFFAOYSA-N trilithium;difluoro oxalate;borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-].FOC(=O)C(=O)OF NDZWKTKXYOWZML-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZKEFILOOQGVKNY-UHFFFAOYSA-N triphenylphosphane;dihydrobromide Chemical compound Br.Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZKEFILOOQGVKNY-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/40—Vinylene carbonate; Substituted vinylene carbonates
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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
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/64—Liquid electrolytes characterised by additives
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- H—ELECTRICITY
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- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
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- H01M2300/0025—Organic electrolyte
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
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Description
また、一般式(1)において、フッ素化アルキル基は、直鎖状又は分岐鎖状のいずれであってもよい。
一般式(3-2)におけるXは、ハロゲン原子であり、なかでも、塩素原子、臭素原子、ヨウ素原子が好ましい。
Rf-X
(式中、Rfは炭素数1~8のフッ素化アルキル基である。Xはハロゲン原子を表す。)で示される化合物(5-1)とを反応させて、一般式(5-2):
化合物(5-2)と塩基又は金属とを反応させて、一般式(1):
一般式(5-1)及び一般式(5-2)におけるXは、ハロゲン原子であり、なかでも、塩素原子、臭素原子、ヨウ素原子が好ましく、ヨウ素原子が特に好ましい。
(式中、Rf1及びRf2は、同じか又は異なり、炭素数1~4のアルキル基又は含フッ素アルキル基を表す。ただし、Rf1及びRf2の少なくとも一方は炭素数1~4の含フッ素アルキル基である。)で表されるフッ素化鎖状カーボネートが挙げられる。
上記炭素数は、電解液への相溶性が良好である点で、1~3が好ましい。
上記非フッ素化飽和環状カーボネートとして、上述した化合物の1種を用いてもよいし、2種以上を併用してもよい。
上記フッ素化飽和環状カーボネート(A)を含むと、上記電解液をリチウムイオン二次電池等に適用した場合に、負極に安定な被膜を形成することができ、負極での電解液の副反応を充分に抑制することができる。その結果、極めて安定で優れた充放電特性が得られる。
なお、本明細書中で「エーテル結合」は、-O-で表される結合である。
炭素数が大きくなりすぎると低温特性が低下したり、電解質塩の溶解性が低下したりするおそれがあり、炭素数が少な過ぎると、電解質塩の溶解性の低下、放電効率の低下、更には粘性の増大等がみられることがある。
R1-R2- (a-1)
なお、R1及びR2は、更に、炭素原子、水素原子及びフッ素原子以外の、その他の原子を有していてもよい。
-CH2-、-CHF-、-CF2-、-CHCl-、-CFCl-、-CCl2-
-CH2-、-CHF-、-CF2-、-CHCl-、-CFCl-、-CCl2-
R3-(OR4)n1- (b-1)
(式中、R3はフッ素原子を有していてもよい、好ましくは炭素数1~6のアルキル基;R4はフッ素原子を有していてもよい、好ましくは炭素数1~4のアルキレン基;n1は1~3の整数;ただし、R3及びR4の少なくとも1つはフッ素原子を有している)で示されるものが挙げられる。
フッ素化アルキル基(a)、エーテル結合を有するフッ素化アルキル基(b)、及び、フッ素化アルコキシ基(c)のフッ素含有率は、各基の構造式に基づいて、{(フッ素原子の個数×19)/各基の式量}×100(%)により算出した値である。
なお、フッ素化飽和環状カーボネート(A)のフッ素含有率は、フッ素化飽和環状カーボネート(A)の構造式に基づいて、{(フッ素原子の個数×19)/フッ素化飽和環状カーボネート(A)の分子量}×100(%)により算出した値である。
上記電解質塩としては、二次電池、電気二重層キャパシタ等の電気化学デバイス用の電解液に使用することができる任意のものを用いることができるが、なかでも、リチウム塩が好ましい。
上記リチウム塩としては、例えば、LiClO4、LiPF6及びLiBF4等の無機リチウム塩;LiSO3CF3、LiN(SO2CF3)2、LiN(SO2C2F5)2、LiN(SO2CF3)(SO2C4F9)、LiC(SO2CF3)3、LiPF4(CF3)2、LiPF4(C2F5)2、LiPF4(SO2CF3)2、LiPF4(SO2C2F5)2、LiBF2(CF3)2、LiBF2(C2F5)2、LiBF2(SO2CF3)2、LiBF2(SO2C2F5)2、リチウムジフルオロ(オキサレート)ボレート、リチウムビス(オキサレート)ボレート、及び、式:LiPFa(CnF2n+1)6-a(式中、aは0~5の整数であり、nは1~6の整数である)で表される塩等の含フッ素有機酸リチウム塩等が挙げられる。これらは、単独又は2種以上を組み合わせて用いることができる。
上記電解質塩の濃度は、0.9モル/リットル以上がより好ましく、1.5モル/リットル以下がより好ましい。
上記アンモニウム塩としては、以下(IIa)~(IIe)が挙げられる。
(IIa)テトラアルキル4級アンモニウム塩
一般式(IIa):
などがあげられる。アルキルエーテル基を導入することにより、粘性の低下が図ることができる。
一般式(IIb-1):
一般式(IIc):
で示されるイミダゾリウム塩が好ましく例示できる。また、このイミダゾリウム塩の水素原子の一部又は全部がフッ素原子及び/又は炭素数1~4の含フッ素アルキル基で置換されているものも、耐酸化性が向上する点から好ましい。
一般式(IId):
で示されるN-アルキルピリジニウム塩が好ましく例示できる。また、このN-アルキルピリジニウム塩の水素原子の一部又は全部がフッ素原子及び/又は炭素数1~4の含フッ素アルキル基で置換されているものも、耐酸化性が向上する点から好ましい。
一般式(IIe):
で示されるN,N-ジアルキルピロリジニウム塩が好ましく例示できる。また、このN,N-ジアルキルピロリジニウム塩の水素原子の一部又は全部がフッ素原子及び/又は炭素数1~4の含フッ素アルキル基で置換されているものも、耐酸化性が向上する点から好ましい。
が好ましい。
更に容量を向上させるために、マグネシウム塩を用いてもよい。マグネシウム塩としては、例えば、Mg(ClO4)2、Mg(OOC2H5)2等が好ましい。
上記濃度の上限は、低温特性の点で、3.0モル/リットル以下であることが好ましく、2.0モル/リットル以下であることがより好ましい。
上記アンモニウム塩が、4フッ化ホウ酸トリエチルメチルアンモニウム(TEMABF4)の場合、その濃度は、低温特性に優れる点で、0.8~1.9モル/リットルであることが好ましい。
また、4フッ化ホウ酸スピロビピロリジニウム(SBPBF4)の場合は、0.7~2.0モル/リットルであることが好ましい。
このような化合物を含有することにより、電極界面の安定性が向上し、電池特性を向上させることができる。
上記ポリエチレンオキシドとしては、例えば、ポリエチレンオキシドモノオール、ポリエチレンオキシドカルボン酸、ポリエチレンオキシドジオール、ポリエチレンオキシドジカルボン酸、ポリエチレンオキシドトリオール、ポリエチレンオキシドトリカルボン酸等が挙げられる。これらは単独で使用してもよいし、2種以上を併用してもよい。
なかでも、電池特性がより良好となる点で、ポリエチレンオキシドモノオールとポリエチレンオキシドジオールの混合物、及び、ポリエチレンオキシドカルボン酸とポリエチレンオキシドジカルボン酸の混合物であることが好ましい。
上記重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)法によるポリスチレン換算により測定することができる。
上記ポリエチレンオキシドの含有量は、5×10-6mol/kg以上であることがより好ましい。
フッ素化不飽和環状カーボネートが有するフッ素原子の数は1以上あれば、特に制限されない。中でもフッ素原子が通常6以下、好ましくは4以下であり、1個又は2個のものが最も好ましい。
フッ素化ビニレンカーボネート誘導体としては、4-フルオロビニレンカーボネート、4-フルオロ-5-メチルビニレンカーボネート、4-フルオロ-5-フェニルビニレンカーボネート、4-アリル-5-フルオロビニレンカーボネート、4-フルオロ-5-ビニルビニレンカーボネート等が挙げられる。
なかでも、高温特性を向上させることができる点で、上記電解液は、1,3-プロパンスルトン、及び/又は、1,4-ブタンスルトンを含有することが好ましい。
フッ素化環状カルボン酸エステルを含有させることにより、イオン伝導度の向上、安全性の向上、高温時の安定性向上といった効果が得られる。
Rf10COORf11 (H)
(式中、Rf10は炭素数1~2のフッ素化アルキル基、Rf11は炭素数1~4のフッ素化アルキル基)で示されるフッ素化鎖状カルボン酸エステルが、難燃性が高く、かつ他溶媒との相溶性や耐酸化性が良好な点から好ましい。
炭素数3~10の鎖状エーテルとしては、ジエチルエーテル、ジ-n-ブチルエーテル、ジメトキシメタン、メトキシエトキシメタン、ジエトキシメタン、ジメトキシエタン、メトキシエトキシエタン、ジエトキシエタン、エチレングリコールジ-n-プロピルエーテル、エチレングリコールジ-n-ブチルエーテル、ジエチレングリコールジメチルエーテル等が挙げられる。
上記フッ素化エーテルとしては、下記一般式(I):
Rf13-O-Rf14 (I)
(式中、Rf13及びRf14は同じか又は異なり、炭素数1~10のアルキル基又は炭素数1~10のフッ素化アルキル基である。ただし、Rf13及びRf14の少なくとも一方は、フッ素化アルキル基である。)で表されるフッ素化エーテル(I)が挙げられる。フッ素化エーテル(I)を含有させることにより、電解液の難燃性が向上するとともに、高温高電圧での安定性、安全性が向上する。
なかでも、Rf13及びRf14が、同じか又は異なり、Rf13が炭素数3~6のフッ素化アルキル基であり、かつ、Rf14が炭素数2~6のフッ素化アルキル基であることが好ましい。
上記フッ素含有率の下限は、45質量%がより好ましく、50質量%が更に好ましく、55質量%が特に好ましい。上限は70質量%がより好ましく、66質量%が更に好ましい。
なお、フッ素化エーテル(I)のフッ素含有率は、フッ素化エーテル(I)の構造式に基づいて、{(フッ素原子の個数×19)/フッ素化エーテル(I)の分子量}×100(%)により算出した値である。
なかでも、高沸点、他の溶媒との相溶性や電解質塩の溶解性が良好な点で有利なことから、HCF2CF2CH2OCF2CFHCF3(沸点106℃)、CF3CF2CH2OCF2CFHCF3(沸点82℃)、HCF2CF2CH2OCF2CF2H(沸点92℃)及びCF3CF2CH2OCF2CF2H(沸点68℃)からなる群より選択される少なくとも1種であることが好ましく、HCF2CF2CH2OCF2CFHCF3(沸点106℃)及びHCF2CF2CH2OCF2CF2H(沸点92℃)からなる群より選択される少なくとも1種であることがより好ましい。
Rf15COO-M+ (J)
(式中、Rf15は炭素数3~10のエーテル結合を含んでいてもよい含フッ素アルキル基;M+はLi+、Na+、K+又はNHR’3 +(R’は同じか又は異なり、いずれもH又は炭素数が1~3のアルキル基)である)で表される含フッ素カルボン酸塩や、下記式(K):
Rf16SO3 -M+ (K)
(式中、Rf16は炭素数3~10のエーテル結合を含んでいてもよい含フッ素アルキル基;M+はLi+、Na+、K+又はNHR’3 +(R’は同じか又は異なり、いずれもHまたは炭素数が1~3のアルキル基)である)で表される含フッ素スルホン酸塩等が好ましい。
上記過充電防止剤の含有量は、過充電等の場合に電池の破裂や発火を防止できる点で、電解液中0.1~5質量%であることが好ましい。
A-(D)-B (1-1)
[式中、Dは式(2-1a):
-(D1)n-(FAE)m-(AE)p-(Y)q- (2-1a)
(式中、D1は、式(2a):
FAEは、式(2b):
AEは、式(2c):
Yは、式(2d-1)~(2d-3):
nは0~200の整数;mは0~200の整数;pは0~10000の整数;qは1~100の整数;ただしn+mは0ではなく、D1、FAE、AE及びYの結合順序は特定されない);
A及びBは同じか又は異なり、水素原子、フッ素原子及び/又は架橋性官能基を含んでいてもよいアルキル基、フッ素原子及び/又は架橋性官能基を含んでいてもよいフェニル基、-COOH基、-OR(Rは水素原子又はフッ素原子及び/又は架橋性官能基を含んでいてもよいアルキル基)、エステル基又はカーボネート基(ただし、Dの末端が酸素原子の場合は-COOH基、-OR、エステル基及びカーボネート基ではない)]で表される側鎖に含フッ素基を有する非晶性含フッ素ポリエーテル化合物である。
上記電気化学デバイスとしては、リチウムイオン二次電池、キャパシタ(電気二重層キャパシタ)、ラジカル電池、太陽電池(特に色素増感型太陽電池)、燃料電池、各種電気化学センサー、エレクトロクロミック素子、電気化学スイッチング素子、アルミニウム電解コンデンサ、タンタル電解コンデンサ等が挙げられ、リチウムイオン二次電池、電気二重層キャパシタが好適である。
以下に、上記電気化学デバイス又は二次電池の例として、リチウムイオン二次電池の場合を説明する。
正極は、正極の材料である正極活物質を含む正極合剤と、集電体とから構成される。
上記リチウム含有遷移金属複合酸化物としては、例えば、
式(L):LiaMn2-bM1 bO4(式中、0.9≦a;0≦b≦1.5;M1はFe、Co、Ni、Cu、Zn、Al、Sn、Cr、V、Ti、Mg、Ca、Sr、B、Ga、In、Si及びGeよりなる群から選ばれる少なくとも1種の金属)で表されるリチウム・マンガンスピネル複合酸化物、
式(M):LiNi1-cM2 cO2(式中、0≦c≦0.5;M2はFe、Co、Mn、Cu、Zn、Al、Sn、Cr、V、Ti、Mg、Ca、Sr、B、Ga、In、Si及びGeよりなる群から選ばれる少なくとも1種の金属)で表されるリチウム・ニッケル複合酸化物、又は、
式(N):LiCo1-dM3 dO2(式中、0≦d≦0.5;M3はFe、Ni、Mn、Cu、Zn、Al、Sn、Cr、V、Ti、Mg、Ca、Sr、B、Ga、In、Si及びGeよりなる群から選ばれる少なくとも1種の金属)で表されるリチウム・コバルト複合酸化物が挙げられる。
なお、タップ密度は、正極活物質粉体5~10gを10mlのガラス製メスシリンダーに入れ、ストローク約20mmで200回タップした時の粉体充填密度(タップ密度)g/cm3として求める。
上記正極活物質の粒子は、二次粒子の平均粒子径が40μm以下で、かつ、平均一次粒子径が1μm以下の微粒子を、0.5~7.0体積%含むものであることが好ましい。平均一次粒子径が1μm以下の微粒子を含有させることにより、電解液との接触面積が大きくなり、電極と電解液との間でのリチウムイオンの拡散をより速くすることができ、その結果、電池の出力性能を向上させることができる。
上記結着剤としては、電極製造時に使用する溶媒や電解液に対して安全な材料であれば、任意のものを使用することができ、例えば、ポリフッ化ビニリデン、ポリテトラフルオロエチレン、ポリエチレン、ポリプロピレン、SBR(スチレン・ブタジエンゴム)、イソプレンゴム、ブタジエンゴム、エチレン-アクリル酸共重合体、エチレン-メタクリル酸共重合体、ポリエチレンテレフタレート、ポリメチルメタクリレート、ポリイミド、芳香族ポリアミド、セルロース、ニトロセルロース、NBR(アクリロニトリル-ブタジエンゴム)、フッ素ゴム、エチレン-プロピレンゴム、スチレン・ブタジエン・スチレンブロック共重合体又はその水素添加物、EPDM(エチレン・プロピレン・ジエン三元共重合体)、スチレン・エチレン・ブタジエン・エチレン共重合体、スチレン・イソプレン・スチレンブロック共重合体又はその水素添加物、シンジオタクチック-1,2-ポリブタジエン、ポリ酢酸ビニル、エチレン・酢酸ビニル共重合体、プロピレン・α-オレフィン共重合体、フッ素化ポリフッ化ビニリデン、テトラフルオロエチレン・エチレン共重合体、アルカリ金属イオン(特にリチウムイオン)のイオン伝導性を有する高分子組成物等が挙げられる。なお、これらの物質は、1種を単独で用いてもよく、2種以上を任意の組み合わせ及び比率で併用してもよい。
負極は、負極活物質を含む負極合剤と、集電体とから構成される。
また、SiまたはSnを第1の構成元素とし、それに加えて第2、第3の構成元素を含む複合材料が挙げられる。第2の構成元素は、例えば、コバルト、鉄、マグネシウム、チタン、バナジウム、クロム、マンガン、ニッケル、銅、亜鉛、ガリウム及びジルコニウムのうち少なくとも1種である。第3の構成元素は、例えば、ホウ素、炭素、アルミニウム及びリンのうち少なくとも1種である。
特に、高い電池容量および優れた電池特性が得られることから、上記金属材料として、ケイ素またはスズの単体(微量の不純物を含んでよい)、SiOv(0<v≦2)、SnOw(0≦w≦2)、Si-Co-C複合材料、Si-Ni-C複合材料、Sn-Co-C複合材料、Sn-Ni-C複合材料が好ましい。
LixTiyMzO4 (O)
[一般式(O)中、Mは、Na、K、Co、Al、Fe、Ti、Mg、Cr、Ga、Cu、Zn及びNbからなる群より選ばれる少なくとも1種の元素を表わす。]
で表される化合物であることが好ましい。
上記の一般式(O)で表わされる組成の中でも、
(i)1.2≦x≦1.4、1.5≦y≦1.7、z=0
(ii)0.9≦x≦1.1、1.9≦y≦2.1、z=0
(iii)0.7≦x≦0.9、2.1≦y≦2.3、z=0
の構造が、電池性能のバランスが良好なため特に好ましい。
水系溶媒としては、水、アルコール等が挙げられ、有機系溶媒としてはN-メチルピロリドン(NMP)、ジメチルホルムアミド、ジメチルアセトアミド、メチルエチルケトン、シクロヘキサノン、酢酸メチル、アクリル酸メチル、ジエチルトリアミン、N,N-ジメチルアミノプロピルアミン、テトラヒドロフラン(THF)、トルエン、アセトン、ジエチルエーテル、ジメチルアセトアミド、ヘキサメチルホスファルアミド、ジメチルスルホキシド、ベンゼン、キシレン、キノリン、ピリジン、メチルナフタレン、ヘキサン等が挙げられる。
上記リチウムイオン二次電池は、更に、セパレータを備えることが好ましい。
上記セパレータの材質や形状は、電解液に安定であり、かつ、保液性に優れていれば特に限定されず、公知のものを使用することができる。なかでも、上記電解液に対し安定な材料で形成された、樹脂、ガラス繊維、無機物等が用いられ、保液性に優れた多孔性シート又は不織布状の形態の物等を用いるのが好ましい。
電極群は、上記の正極板と負極板とを上記のセパレータを介してなる積層構造のもの、及び上記の正極板と負極板とを上記のセパレータを介して渦巻き状に捲回した構造のもののいずれでもよい。電極群の体積が電池内容積に占める割合(以下、電極群占有率と称する)は、通常40%以上であり、50%以上が好ましく、また、通常90%以下であり、80%以下が好ましい。
上記電気二重層キャパシタでは、正極及び負極の少なくとも一方は分極性電極であり、分極性電極及び非分極性電極としては特開平9-7896号公報に詳しく記載されている以下の電極が使用できる。
下記式で示されるブロモビニレンカーボネートを、Chem.Ber.103,1970,3949に記載される方法に従い合成した。
1H-NMR(acetone-d6):δ8.45(t,J=2.39 Hz,1H)
13C-NMR(acetone-d6):δ110.13~111.05(m),112.49~114.03(m),116.52(t,J=133.90 Hz),119.38(t,J=133.90 Hz),132.18(t,J=139.89 Hz),136.02(t,J=23.98 Hz),151.23
19F-NMR(acetone-d6):δ-79.43(t,J=10.53 Hz,3F),-113.39(t,J=12.03 Hz,2F),-121.56(dd,J=8.56、2.26 Hz,2F),-124.18~-124.26(m,2F)
下記式で示されるブロモビニレンカーボネートを、Chem.Ber.103,1970,3949に記載される方法に従い合成した。
1H-NMR(acetone-d6):δ8.47(t,J=2.39 Hz,1H)
13C-NMR(acetone-d6):δ105.97~107.27(m),108.52~109.83(m),111.06~112.20(m),114.32(t,J=130.69 Hz),117.18(t,J=130.69 Hz),120.05(t,J=137.09 Hz),129.91(t,J=136.69 Hz),134.29(t,J=25.18 Hz),149.24
19F-NMR(acetone-d6):δ-81.71(t,J=9.02 Hz,3F),-115.71(t,J=12.03 Hz,2F),-122.47(s,2F),-123.17(d,J=6.76 Hz,2F),-123.42(d,J=7.14Hz,2F),-126.76~-126.85(m,2F)
下記式で示されるブロモビニレンカーボネートを、Chem.Ber.103,1970,3949に記載される方法に従い合成した。
1000mL光反応装置に、100W高圧水銀灯を取り付け、下記式で示される4-パーフルオロヘキシル-エチレンカーボネート20.00gと四塩化炭素197.00mLとを導入した。
1000mL光反応装置に、100W高圧水銀灯を取り付け、下記式で示される4-パーフルオロブチル-エチレンカーボネート20.00gと四塩化炭素261.37mLを導入した。
200mLガラス製反応容器に還流管を取り付け、LiBr 2.15gとN-メチルピロリドン(NMP)40.00mLを導入し、35℃で1時間撹拌した。反応器内を二酸化炭素で置換し、下記式で示されるエポキシ10.00gを滴下し、35℃で6時間撹拌した。
300mLオートクレーブにビニレンカーボネート10.00g、パーフルオロヘキシルアイオダイド103.65g、t-ブチルペルオキシイソプロピルモノカーボネート1.02gを導入し、120℃で6時間撹拌した。反応熟成後、反応液を濃縮することで、C6F13ECI粗体を白色固体として得た。C6F13ECIは、下記式で示されるカーボネートである。
300mLオートクレーブにビニレンカーボネート10.00g、パーフルオロブチルアイオダイド80.40g、t-ブチルペルオキシイソプロピルモノカーボネート1.02gを導入し、120℃で6時間撹拌した。反応熟成後、反応液を濃縮することで、C4F9ECI粗体を白色固体として得た。C4F9ECIは、下記式で示されるカーボネートである。
実施例1
乾燥アルゴン雰囲気下、エチレンカーボネート及びエチルメチルカーボネートの混合物(容量比3:7)99重量部に、合成例4の4-パーフルオロヘキシル-ビニレンカーボネート0.5重量部とビニレンカーボネート(VC)0.5重量部とを添加し、次いで十分に乾燥したLiPF6を1モル/リットルの割合となるように溶解して電解液とした。
LiNi1/3Mn1/3Co1/3O2とカーボンブラックとポリフッ化ビニリデン(呉羽化学(株)製、商品名KF-7200)を92/3/5(質量%比)で混合した正極活物質をN-メチル-2-ピロリドンに分散してスラリー状とした正極合剤スラリーを準備した。アルミ集電体上に、得られた正極合剤スラリーを均一に塗布し、乾燥して正極合剤層(厚さ50μm)を形成し、その後、ローラプレス機により圧縮成形して、正極積層体を製造した。
コイン型リチウム二次電池について、次の要領で高電圧でのサイクル特性と高温保存特性を調べた。
充電:1C、4.2Vにて充電電流が1/10Cになるまで保持(CC・CV充電)
放電:1C 3.0Vcut(CC放電)
高温保存特性については上記の充放電条件(1.0Cで所定の電圧にて充電電流が1/10Cになるまで充電し1C相当の電流で3.0Vまで放電する)により充放電を行い、放電容量を調べた。その後、再度上記の充電条件で充電をし、85℃の恒温槽の中に3日、保存した。保存後の電池を25℃において、上記の放電条件で放電終止電圧3Vまで放電させて残存容量を測定し、さらに上記の充電条件で充電した後、上記の放電条件での定電流で放電終止電圧3Vで放電を行って回復容量を測定した。保存前の放電容量を100とした場合の回復容量を表1に示す。
また、その時に発生したガス量(mL)についても表1に示す。
合成例4の4-パーフルオロヘキシル-ビニレンカーボネートを合成例5の4-パーフルオロブチル-ビニレンカーボネートに変更した以外は実施例1と同様にして電池を作製し試験を行った。結果を表1に示す。
合成例4の4-パーフルオロヘキシル-ビニレンカーボネートを合成例6の4-トリフルオロメチル-ビニレンカーボネートに変更した以外は実施例1と同様にして電池を作製し試験を行った。結果を表1に示す。
4-パーフルオロヘキシル-ビニレンカーボネートの代わりにVCを更に0.5wt%増やした(VCを合計1.0重量部添加した)以外は実施例1と同様にして電池を作製し試験を行った。結果を表1に示す。
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US20180346437A1 (en) | 2018-12-06 |
CN110204525A (zh) | 2019-09-06 |
EP3667804A1 (en) | 2020-06-17 |
JP2020145199A (ja) | 2020-09-10 |
PL3205649T3 (pl) | 2021-08-30 |
US10464916B2 (en) | 2019-11-05 |
WO2016080484A1 (ja) | 2016-05-26 |
EP3205649A1 (en) | 2017-08-16 |
EP3205649B1 (en) | 2021-02-24 |
JPWO2016080484A1 (ja) | 2017-08-03 |
CN110204525B (zh) | 2022-01-28 |
EP3667804B1 (en) | 2021-04-21 |
PL3750884T3 (pl) | 2022-07-11 |
US10287263B2 (en) | 2019-05-14 |
EP3750884A1 (en) | 2020-12-16 |
HUE054520T2 (hu) | 2021-09-28 |
HUE054899T2 (hu) | 2021-10-28 |
EP3205649A4 (en) | 2019-07-31 |
HUE059073T2 (hu) | 2022-10-28 |
JP2019024016A (ja) | 2019-02-14 |
US20190185445A1 (en) | 2019-06-20 |
JP6940468B2 (ja) | 2021-09-29 |
PL3667804T3 (pl) | 2021-11-02 |
JP6458808B2 (ja) | 2019-01-30 |
CN107108550A (zh) | 2017-08-29 |
EP3750884B1 (en) | 2022-03-30 |
CN107108550B (zh) | 2020-03-03 |
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