JP2022045347A - 含フッ素カルボン酸塩化合物 - Google Patents
含フッ素カルボン酸塩化合物 Download PDFInfo
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- JP2022045347A JP2022045347A JP2021144392A JP2021144392A JP2022045347A JP 2022045347 A JP2022045347 A JP 2022045347A JP 2021144392 A JP2021144392 A JP 2021144392A JP 2021144392 A JP2021144392 A JP 2021144392A JP 2022045347 A JP2022045347 A JP 2022045347A
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- Prior art keywords
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- carbonate
- methyl
- fluorinated
- mass
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- -1 carboxylate compound Chemical class 0.000 title abstract description 271
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 148
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract description 78
- 239000011737 fluorine Substances 0.000 title abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 101
- 238000004519 manufacturing process Methods 0.000 claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000000654 additive Substances 0.000 claims abstract description 29
- 230000000996 additive effect Effects 0.000 claims abstract description 20
- 125000000962 organic group Chemical group 0.000 claims abstract description 18
- 239000008151 electrolyte solution Substances 0.000 claims description 124
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 87
- 229910052744 lithium Inorganic materials 0.000 claims description 80
- 229910052751 metal Inorganic materials 0.000 claims description 59
- 229910001416 lithium ion Inorganic materials 0.000 claims description 57
- 239000002184 metal Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 38
- 239000003792 electrolyte Substances 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 31
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 46
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 173
- 125000004432 carbon atom Chemical group C* 0.000 description 106
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 94
- 150000005676 cyclic carbonates Chemical class 0.000 description 87
- 239000007774 positive electrode material Substances 0.000 description 70
- 239000002904 solvent Substances 0.000 description 70
- 239000010410 layer Substances 0.000 description 65
- 235000002639 sodium chloride Nutrition 0.000 description 60
- 150000003839 salts Chemical class 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 52
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 51
- 150000008065 acid anhydrides Chemical class 0.000 description 46
- 125000005843 halogen group Chemical group 0.000 description 44
- 229910052799 carbon Inorganic materials 0.000 description 42
- 125000001183 hydrocarbyl group Chemical group 0.000 description 41
- 150000001733 carboxylic acid esters Chemical class 0.000 description 40
- 229920006395 saturated elastomer Polymers 0.000 description 40
- 150000005678 chain carbonates Chemical class 0.000 description 39
- 125000002947 alkylene group Chemical group 0.000 description 37
- 239000011230 binding agent Substances 0.000 description 37
- 230000000694 effects Effects 0.000 description 36
- 239000007773 negative electrode material Substances 0.000 description 33
- 230000007423 decrease Effects 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 30
- 239000000126 substance Substances 0.000 description 30
- 239000000463 material Substances 0.000 description 29
- 150000001450 anions Chemical class 0.000 description 28
- 239000003990 capacitor Substances 0.000 description 28
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 27
- 239000003575 carbonaceous material Substances 0.000 description 26
- 229910052782 aluminium Inorganic materials 0.000 description 25
- 125000004093 cyano group Chemical group *C#N 0.000 description 25
- 239000002131 composite material Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [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
- 238000007254 oxidation reaction Methods 0.000 description 21
- 238000003860 storage Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 20
- 230000003647 oxidation Effects 0.000 description 20
- 239000010936 titanium Substances 0.000 description 20
- 239000004020 conductor Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 239000010408 film Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000002562 thickening agent Substances 0.000 description 18
- 229910052719 titanium Inorganic materials 0.000 description 18
- 239000000956 alloy Substances 0.000 description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 17
- 150000008064 anhydrides Chemical class 0.000 description 17
- 239000010949 copper Substances 0.000 description 17
- 150000002170 ethers Chemical group 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 229910003002 lithium salt Inorganic materials 0.000 description 17
- 159000000002 lithium salts Chemical class 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 229910052723 transition metal Inorganic materials 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 229910052802 copper Inorganic materials 0.000 description 16
- 125000000524 functional group Chemical group 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229910019142 PO4 Inorganic materials 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 229910045601 alloy Inorganic materials 0.000 description 15
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
- 230000001771 impaired effect Effects 0.000 description 15
- 239000010452 phosphate Substances 0.000 description 15
- 235000021317 phosphate Nutrition 0.000 description 15
- 150000003624 transition metals Chemical class 0.000 description 15
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 14
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
- 229910052759 nickel Inorganic materials 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- 229910013872 LiPF Inorganic materials 0.000 description 13
- 101150058243 Lipf gene Proteins 0.000 description 13
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 239000000470 constituent Substances 0.000 description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 239000011572 manganese Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000002245 particle Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 0 CC(CC1)CC1C(C1)C(C23)C1C2*3*(C1)C1=C(C)C Chemical compound CC(CC1)CC1C(C1)C(C23)C1C2*3*(C1)C1=C(C)C 0.000 description 12
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 229910052796 boron Inorganic materials 0.000 description 12
- 125000001033 ether group Chemical group 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 229910052710 silicon Inorganic materials 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 12
- 229910052718 tin Inorganic materials 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 229910013075 LiBF Inorganic materials 0.000 description 11
- 239000011149 active material Substances 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 125000000732 arylene group Chemical group 0.000 description 11
- 239000006229 carbon black Substances 0.000 description 11
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 229910052804 chromium Inorganic materials 0.000 description 10
- 239000011651 chromium Substances 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 239000002905 metal composite material Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical group O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 9
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- 229910052720 vanadium Inorganic materials 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 8
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 8
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- 239000011593 sulfur Chemical group 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
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- GRCAXSKSTZXYIK-UHFFFAOYSA-N cyclopentanecarbonyl cyclopentanecarboxylate Chemical compound C1CCCC1C(=O)OC(=O)C1CCCC1 GRCAXSKSTZXYIK-UHFFFAOYSA-N 0.000 description 7
- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 description 7
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 7
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- 150000002825 nitriles Chemical class 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
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- 229940014800 succinic anhydride Drugs 0.000 description 6
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 5
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- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical class [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
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- TWEXXDYPTGTORL-UHFFFAOYSA-N prop-2-ynoyl 4-methylbenzoate Chemical compound Cc1ccc(cc1)C(=O)OC(=O)C#C TWEXXDYPTGTORL-UHFFFAOYSA-N 0.000 description 1
- FJXGTHPNFQEMRD-UHFFFAOYSA-N prop-2-ynoyl benzoate Chemical compound O=C(OC(=O)c1ccccc1)C#C FJXGTHPNFQEMRD-UHFFFAOYSA-N 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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- RBYFNZOIUUXJQD-UHFFFAOYSA-J tetralithium oxalate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O RBYFNZOIUUXJQD-UHFFFAOYSA-J 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- LWLOKSXSAUHTJO-IMJSIDKUSA-N trans-2,3-butylene carbonate Chemical compound C[C@@H]1OC(=O)O[C@H]1C LWLOKSXSAUHTJO-IMJSIDKUSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910000319 transition metal phosphate Inorganic materials 0.000 description 1
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 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
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
- 229920000685 trimethylsilyl polyphosphate Polymers 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 229910001456 vanadium ion Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/16—Halogenated acetic acids
- C07C53/18—Halogenated acetic acids containing fluorine
-
- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】式(P1):(B1f)mp(A1)np[B1fはRfCOO;Rfは1個以上のF原子を有する炭化水素;A1はH以外の基;mpは(A1の価数)×npであって1又は2;npはmp/(A1の価数)であって1;A1の価数は1又は2]で表される化合物の製造方法であって、式(S1):(B1f)(R1)[B1fは前記と同意義;R1は有機基]で表される化合物を、式(S2):(A1)ms2(B2)ns2[A1はH以外の基;B2はOH、CO3、又はHCO3;ms2は(B2の価数)×ns2/(A1の価数)であって、1又は2;ns2は(A1の価数)×ms2/(B2の価数)であって、1又は2]で表される化合物、又はその水和物と、反応させる工程Aを含む。
【選択図】なし
Description
含フッ素カルボン酸ハライドと水酸化リチウムを反応させる方法又は含フッ素カルボン酸と水酸化リチウム又は炭酸リチウムを反応させる方法により含フッ素カルボン酸リチウムを合成する方法が公知である(特許文献2)。
式(P1):(B1f)mp(A1)np
[式中、
B1fは、RfCOOであり、
Rfは、1個以上のフッ素原子を有する炭化水素であり、
A1は、H以外の基であり、
mpは、(A1の価数)×np/(B1の価数)の数であって、且つ1又は2であり、
npは、(B1の価数)×mp/(A1の価数)の数であって、且つ1であり、
A1の価数は、1又は2であり、及び
B1fの価数は、1である。]
で表される化合物
の製造方法であって、
式(S1):(B1f)(R1)
[式中、
B1fは、前記と同意義であり、及び
R1は、有機基である。
ただし、R1は、A1とは異なる基である。]
で表される化合物を、
式(S2):(A1)ms2(B2)ns2
[式中、
A1は、前記と同意義であり、
B2は、OH、CO3、又はHCO3であり、
ms2は、(B2の価数)×ns2/(A1の価数)の数であって、且つ1又は2であり、及び
ns2は、(A1の価数)×ms2/(B2の価数)であって、且つ1又は2である。]
で表される化合物、又はその水和物と、
反応させる工程A
を含む製造方法
によって、解決され得る。
式(P1):(B1f)mp(A1)np
[式中、
B1fは、RfCOOであり、
Rfは、1個以上のフッ素原子を有する炭化水素であり、
A1は、H以外の基であり、
mpは、(A1の価数)×np/(B1fの価数)の数であって、且つ1又は2であり、
npは、(B1fの価数)×mp/(A1の価数)の数であって、且つ1であり、
A1の価数は、1又は2であり、及び
B1fの価数は、1である。]
で表される化合物
の製造方法であって、
式(S1):(B1f)(R1)
[式中、
B1fは、前記と同意義であり、及び
R1は、有機基である。
ただし、R1は、A1とは異なる基である。]
で表される化合物を、
式(S2):(A1)ms2(B2)ns2
[式中、
A1は、前記と同意義であり、
B2は、OH、CO3、又はHCO3であり、
ms2は、(B2の価数)×ns2/(A1の価数)の数であって、且つ1又は2であり、及び
ns2は、(A1の価数)×ms2/(B2の価数)であって、且つ1又は2である。]
で表される化合物、又はその水和物と、
反応させる工程A
を含む、製造方法。
A1は、金属原子、又はアンモニウムである、項1に記載の製造方法。
前記工程Aで副生成する、
式(P2):(R1)op(B2)
[式中、
B2及びR1は、前記と同意義であり、及び
opは、(B2の価数)/(R1の価数)の数であって、且つ1又は2である。]
で表される化合物を、除去する工程B
を更に含む、項1又は2に記載の製造方法。
Rfが、1個以上のフッ素原子を有するC1-6アルキル基である、項1~3のいずれか一項に記載の製造方法。
Rfが、2個以上のフッ素原子を有するC1-3アルキル基である、項1~4のいずれか一項に記載の製造方法。
A1は、アルカリ金属原子である、項1~5のいずれか一項に記載の製造方法。
A1は、Liである、項1~6のいずれか一項に記載の製造方法。
B2は、OHである、項1~7のいずれか一項に記載の製造方法。
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、金属原子である。]
で表される化合物、及び
前記式(P1A)で表される化合物に対して、0~50000質量ppmの水
を含有する、
電気化学デバイス用添加剤。
項9に記載の電気化学デバイス用添加剤を含有する、電解液。
項10に記載の電解液を備える、電気化学デバイス。
項10に記載の電解液を備える、リチウムイオン二次電池。
水分含有量が、50000質量ppm以下である、
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物。
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物、及び
前記式(P1)で表される化合物に対して50000質量ppm以下の水
を含有する組成物。
項1~8のいずれか一項に記載の製造方法で製造された、
項13に記載の化合物。
項1~8のいずれか一項に記載の製造方法で製造された、
項14に記載の組成物。
本明細書中の記号及び略号は、特に限定のない限り、本明細書の文脈に沿い、本開示の発明が属する技術分野において通常用いられる意味に理解できる。
(1)ヒドロカルビル(これは、1個以上の置換基を有していてもよい。)、
(2)ヒドロカルビル(これは、1個以上の置換基を有していてもよい。)に1個以上のヘテロ原子が挿入された基[本明細書中、これを「ヘテロヒドロカルビル」と称する場合がある。)]、
を包含する。
式:RCO2-(当該式中、Rはアルキル基である。)で表される基、及び
式:Ra-CO2-Rb-(当該式中、Raはアルキル基であり、及びRbはアルキレン基である。)で表される基
を包含できる。
環構成原子として、酸素、硫黄、及び窒素からなる群より選択される1個以上(例:1個、2個、又は3個)のヘテロ原子を有する5~6員ヘテロアリール基[例:ピロリル(例:1-ピロリル、2-ピロリル、3-ピロリル)、フリル(例:2-フリル、3-フリル)、チエニル(例:2-チエニル、3-チエニル)、ピラゾリル(例:1-ピラゾリル、3-ピラゾリル、4-ピラゾリル)、イミダゾリル(例:1-イミダゾリル、2-イミダゾリル、4-イミダゾリル)、イソキサゾリル(例:3-イソキサゾリル、4-イソキサゾリル、5-イソキサゾリル)、オキサゾリル(例:2-オキサゾリル、4-オキサゾリル、5-オキサゾリル)、イソチアゾリル(例:3-イソチアゾリル、4-イソチアゾリル、5-イソチアゾリル)、チアゾリル(例:2-チアゾリル、4-チアゾリル、5-チアゾリル)、トリアゾリル(例:1,2,3-トリアゾール-4-イル、1,2,4-トリアゾール-3-イル)、オキサジアゾリル(例:1,2,4-オキサジアゾール-3-イル、1,2,4-オキサジアゾール-5-イル)、チアジアゾリル(例:1,2,4-チアジアゾール-3-イル、1,2,4-チアジアゾール-5-イル)、テトラゾリル、ピリジル(例:2-ピリジル、3-ピリジル、4-ピリジル)、ピリダジニル(例:3-ピリダジニル、4-ピリダジニル)、ピリミジニル(例:2-ピリミジニル、4-ピリミジニル、5-ピリミジニル)、及びピラジニル等を包含できる。]
を包含できる。
工程A
本開示の一態様の製造方法は、
式(P1):(B1f)mp(A1)np
[式中、
B1fは、RfCOOであり、
Rfは、1個以上のフッ素原子を有する炭化水素基であり、
A1は、H以外の基であり、
mpは、(A1の価数)×np/(B1の価数)の数であって、且つ1又は2であり、
npは、(B1の価数)×mp/(A1の価数)の数であって、且つ1であり、
A1の価数は、1又は2であり、及び
B1fの価数は、1である。]
で表される化合物
の製造方法であって、
式(S1):(B1f)(R1)
[式中、
B1fは、前記と同意義であり、
R1は、有機基である。
ただし、R1は、A1とは異なる基である。]
で表される化合物を、
式(S2):(A1)ms2(B2)ns2
[式中、
A1は、前記と同意義であり、
B2は、OH、CO3、又はHCO3であり、
ms2は、(B2の価数)×ns2/(A1の価数)の数であって、且つ1又は2であり、及び
ns2は、(A1の価数)×ms2/(B2の価数)であって、且つ1又は2である。]
で表される化合物、又はその水和物と、
反応させる工程A
を含む製造方法である。
(1)アルコール溶媒[例:メタノール、エタノール、n-プロパノール、イソプロパノール、n-ブタノール、ペンタノール、ヘキサノール、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、ポリプロピレングリコール、トリメチレングリコール、ヘキサントリオール];
(2)非芳香族炭化水素溶媒[例:ペンタン、ヘキサン、ヘプタン、オクタン、シクロヘキサン、デカヒドロナフタレン、n-デカン、イソドデカン、トリデカン];
(3)芳香族炭化水素溶媒[例:ベンゼン、トルエン、キシレン、テトラリン、ベラトロール、エチルベンゼン、ジエチルベンゼン、メチルナフタレン、アニソール、フェネトールニトロベンゼン、o-ニトロトルエン、メシチレン、インデン、ジフェニルスルフィド、アニソール、プロピオフェノン];
(4)ケトン溶媒[例:アセトン、メチルエチルケトン、ジエチルケトン、ヘキサノン、メチルイソブチルケトン、ヘプタノン、ジイソブチルケトン、アセトニルアセトン、メチルヘキサノン、アセトフェノン、シクロヘキサノン、ジアセトンアルコール、プロピオフェノン、イソホロン、];
(5)ハロゲン化炭化水素溶媒[例:ジクロロメタン、クロロホルム、クロロベンゼン];
(6)エーテル溶媒[例:ジエチルエーテル、テトラヒドロフラン(THF)、ジイソプロピルエーテル、メチル-t-ブチルエーテル(MTBE)、ジオキサン、ジメトキシエタン、ジグライム、アニソール、フェネトール、1,1-ジメトキシシクロヘキサン、ジイソアミルエーテル、シクロペンチルメチルエーテル(CPME)];
(7)エステル溶媒[例:酢酸エチル、酢酸イソプロピル、マロン酸ジエチル、3-メトキシ-3-メチルブチルアセテート、γ-ブチロラクトン、エチレンカーボネート、プロピレンカーボネート、炭酸ジメチル、α-アセチル-γ-ブチロラクトン];
(8)ニトリル溶媒[例:アセトニトリル、ベンゾニトリル];
(9)スルホキシド系溶媒[例:ジメチルスルホキシド、スルホラン];及び
(10)アミド溶媒[例:N,N-ジメチルホルムアミド(DMF)、N,N-ジメチルアセトアミド、N-メチルピロリドン(NMP)、1,3-ジメチル-2-イミダゾリジノン(DMI)、N,N-ジメチルアクリルアミド、N,N-ジメチルアセトアセトアミド(DMA)、N,N-ジエチルホルムアミド、N,N-ジエチルアセトアミド]
を包含できる。
式(P2):(R1)op(B2)
[式中、
B2及びR1は、前記と同意義であり、及び
opは、(B2の価数)/(R1の価数)の数であって、且つ1又は2である。]
で表される化合物(P2)を除去する工程Bの前に、所望により、例えば、当該化合物(P2)以外の不要物の除去のため、吸着除去、濾過及び/又はデカンテーションの処理を、行ってもよい。
本開示の一態様の製造方法は、前記工程Aで副生成する、
式(P2):(R1)op(B2)
[式中、
B2及びR1は、前記と同意義であり、及び
opは、(B2の価数)/(R1の価数)の数であって、且つ1又は2である。]
で表される化合物を、除去する工程B
を更に含むことができる。
本開示の一態様の、電気化学デバイス用添加剤は、
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、金属原子である。]
で表される化合物、及び
前記式(P1)で表される化合物に対して、0~50000質量ppmの水
を含有する。
本開示の一態様の化合物は、水分含有量が、50000質量ppm以下である、
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物
である。
本開示の一態様の組成物は、
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物、及び
前記式(P1)で表される化合物に対して50000質量ppm以下の水
を含有する組成物
である。
本開示の一態様の電解液は、本開示の電気化学デバイス用添加剤、化合物、又は組成物を含有する。
通常0.001質量%以上、好ましくは0.01質量%以上、より好ましくは0.05質量%以上、更に好ましくは0.1質量%以上、より更に好ましくは0.2質量%以上、及び特に好ましくは0.5質量%以上であることができる。
通常10質量%以下、好ましくは5質量%以下、より好ましくは3質量%以下、更に好ましくは2質量%以下、より更に好ましくは1.8質量%以下、及び特に好ましくは1.5質量%以下であることができる。
で示される化合物が挙げられる。前記フッ素化アルキル基とは、-CF3、-CF2H、-CH2F等が挙げられる。
R1-R2- (a-1)
(式中、R1はフッ素原子を有していてもよい炭素数1以上のアルキル基;R2はフッ素原子を有していてもよい炭素数1~3のアルキレン基;ただし、R1及びR2の少なくとも一方はフッ素原子を有している)
で示されるフッ素化アルキル基が、電解質塩の溶解性が良好な点から好ましく例示できる。
-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。
Rf2OCOOR7 (B)
(式中、Rf2は、炭素数1~7のフッ素化アルキル基であり、R7は、炭素数1~7のフッ素原子を含んでいてもよいアルキル基である。)
で示される化合物を挙げることができる。
R1-R2- (d-1)
(式中、R1はフッ素原子を有していてもよい炭素数1以上のアルキル基;R2はフッ素原子を有していてもよい炭素数1~3のアルキレン基;ただし、R1及びR2の少なくとも一方はフッ素原子を有している)で示されるフッ素化アルキル基が、電解質塩の溶解性が良好な点から好ましく例示できる。
-CH2-、-CHF-、-CF2-、-CHCl-、-CFCl-、-CCl2-。
{(フッ素原子の個数×19)/フッ素化鎖状カーボネートの分子量}×100(質量%)
により算出した値である。
R31COOR32
(式中、R31及びR32は、互いに独立に、炭素数1~4のフッ素原子を含んでいてもよいアルキル基であり、R31及びR32の少なくとも一方はフッ素原子を含む。)
で示されるフッ素化鎖状カルボン酸エステルが、他溶媒との相溶性や耐酸化性が良好な点から好ましい。
一般式(5):
Aa+は金属イオン、水素イオン又はオニウムイオンを示す。
aは1~3の整数、bは1~3の整数、pはb/a、n203は1~4の整数、n201は0~8の整数、n202は0又は1、Z201は遷移金属、周期律表のIII族、IV族又はV族の元素を示す。
X201は、O、S、炭素数1~10のアルキレン基、炭素数1~10のハロゲン化アルキレン基、炭素数6~20のアリーレン基又は炭素数6~20のハロゲン化アリーレン基(アルキレン基、ハロゲン化アルキレン基、アリーレン基、及び、ハロゲン化アリーレン基はその構造中に置換基、ヘテロ原子を持っていてもよく、またn202が1でn203が2~4のときにはn203個のX201はそれぞれが結合していてもよい)。
L201は、ハロゲン原子、シアノ基、炭素数1~10のアルキル基、炭素数1~10のハロゲン化アルキル基、炭素数6~20のアリール基、炭素数6~20のハロゲン化アリール基(アルキレン基、ハロゲン化アルキレン基、アリーレン基、及び、ハロゲン化アリーレン基はその構造中に置換基、ヘテロ原子を持っていてもよく、またn201が2~8のときにはn201個のL201はそれぞれが結合して環を形成してもよい)又は-Z203Y203を示す。
Y201、Y202及びZ203は、それぞれ独立でO、S、NY204、炭化水素基又はフッ素化炭化水素基。Y203及びY204は、それぞれ独立でH、F、炭素数1~10のアルキル基、炭素数1~10のハロゲン化アルキル基、炭素数6~20のアリール基又は炭素数6~20のハロゲン化アリール基(アルキル基、ハロゲン化アルキル基、アリール基及びハロゲン化アリール基はその構造中に置換基、ヘテロ原子を持っていてもよく、Y203又はY204が複数個存在する場合にはそれぞれが結合して環を形成してもよい)を示す。
で示される化合物、又は、一般式:
で示される化合物であることが好ましい。
LiWOF5等のタングステン酸リチウム類;
HCO2Li、CH3CO2Li、CH2FCO2Li、CHF2CO2Li、CF3CO2Li、CF3CH2CO2Li、CF3CF2CO2Li、CF3CF2CF2CO2Li、CF3CF2CF2CF2CO2Li等のカルボン酸リチウム塩類;
FSO3Li、CH3SO3Li、CH2FSO3Li、CHF2SO3Li、CF3SO3Li、CF3CF2SO3Li、CF3CF2CF2SO3Li、CF3CF2CF2CF2SO3Li、リチウムメチルサルフェート、リチウムエチルサルフェート(C2H5OSO3Li)、リチウム2,2,2-トリフルオロエチルサルフェート等のS=O基を有するリチウム塩類;
LiN(FCO)2、LiN(FCO)(FSO2)、LiN(FSO2)2、LiN(FSO2)(CF3SO2)、LiN(CF3SO2)2、LiN(C2F5SO2)2、リチウムビスパーフルオロエタンスルホニルイミド、リチウム環状1,2-パーフルオロエタンジスルホニルイミド、リチウム環状1,3-パーフルオロプロパンジスルホニルイミド、リチウム環状1,2-エタンジスルホニルイミド、リチウム環状1,3-プロパンジスルホニルイミド、リチウム環状1,4-パーフルオロブタンジスルホニルイミド、LiN(CF3SO2)(FSO2)、LiN(CF3SO2)(C3F7SO2)、LiN(CF3SO2)(C4F9SO2)、LiN(POF2)2等のリチウムイミド塩類;
LiC(FSO2)3、LiC(CF3SO2)3、LiC(C2F5SO2)3等のリチウムメチド塩類;
その他、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(例えばLiPF3(C2F5)3、LiPF3(CF3)3、LiPF3(iso-C3F7)3、LiPF5(iso-C3F7)、LiPF4(CF3)2、LiPF4(C2F5)2)、LiPF4(CF3SO2)2、LiPF4(C2F5SO2)2、LiBF3CF3、LiBF3C2F5、LiBF3C3F7、LiBF2(CF3)2、LiBF2(C2F5)2、LiBF2(CF3SO2)2、LiBF2(C2F5SO2)2等の含フッ素有機リチウム塩類、LiSCN、LiB(CN)4、LiB(C6H5)4、Li2(C2O4)、LiP(C2O4)3、Li2B12FbH12-b(bは0~3の整数)等が挙げられる。
一般式(IIa):
で示されるテトラアルキル4級アンモニウム塩が好ましく例示できる。また、このアンモ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。
で示されるテトラアルキル4級アンモニウム塩、一般式(IIa-2):
で示されるアルキルエーテル基含有トリアルキルアンモニウム塩、
等が挙げられる。アルキルエーテル基を導入することにより、粘性の低下を図ることができる。
一般式(IIb-1):
で示されるスピロ環ビピロリジニウム塩、一般式(IIb-2):
で示されるスピロ環ビピロリジニウム塩、又は、一般式(IIb-3):
で示されるスピロ環ビピロリジニウム塩が好ましく挙げられる。また、このスピロ環ビ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。
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。
で示される化合物(2)を更に含むことが好ましい。前記電解液が化合物(2)を含むと、高温で保管した場合でも、容量保持率が一層低下しにくく、ガスの発生量が更に増加しにくい。
で示される化合物(3)、及び、一般式(4):
で示される化合物(4)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い。
で表されるニトリル化合物からなる群より選択される少なくとも1種を含んでもよい。これにより、電気化学デバイスの高温保存特性を向上させることができる。前記ニトリル化合物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。
2-プロピニルメチルカーボネート、2-プロピニルエチルカーボネート、2-プロピニルプロピルカーボネート、2-プロピニルブチルカーボネート、2-プロピニルフェニルカーボネート、2-プロピニルシクロヘキシルカーボネート、ジ-2-プロピニルカーボネート、1-メチル-2-プロピニルメチルカーボネート、1、1-ジメチル-2-プロピニルメチルカーボネート、2-ブチニルメチルカーボネート、3-ブチニルメチルカーボネート、2-ペンチニルメチルカーボネート、3-ペンチニルメチルカーボネート、4-ペンチニルメチルカーボネート等のモノカーボネート;2-ブチン-1,4-ジオールジメチルジカーボネート、2-ブチン-1,4-ジオールジエチルジカーボネート、2-ブチン-1,4-ジオールジプロピルジカーボネート、2-ブチン-1,4-ジオールジブチルジカーボネート、2-ブチン-1,4-ジオールジフェニルジカーボネート、2-ブチン-1,4-ジオールジシクロヘキシルジカーボネート等のジカーボネート;
酢酸2-プロピニル、プロピオン酸2-プロピニル、酪酸2-プロピニル、安息香酸2-プロピニル、シクロヘキシルカルボン酸2-プロピニル、酢酸1、1-ジメチル-2-プロピニル、プロピオン酸1、1-ジメチル-2-プロピニル、酪酸1、1-ジメチル-2-プロピニル、安息香酸1、1-ジメチル-2-プロピニル、シクロヘキシルカルボン酸1、1-ジメチル-2-プロピニル、酢酸2-ブチニル、酢酸3-ブチニル、酢酸2-ペンチニル、酢酸3-ペンチニル、酢酸4-ペンチニル、アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸ビニル、アクリル酸2-プロペニル、アクリル酸2-ブテニル、アクリル酸3-ブテニル、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸プロピル、メタクリル酸ビニル、メタクリル酸2-プロペニル、メタクリル酸2-ブテニル、メタクリル酸3-ブテニル、2-プロピン酸メチル、2-プロピン酸エチル、2-プロピン酸プロピル、2-プロピン酸ビニル、2-プロピン酸2-プロペニル、2-プロピン酸2-ブテニル、2-プロピン酸3-ブテニル、2-ブチン酸メチル、2-ブチン酸エチル、2-ブチン酸プロピル、2-ブチン酸ビニル、2-ブチン酸2-プロペニル、2-ブチン酸2-ブテニル、2-ブチン酸3-ブテニル、3-ブチン酸メチル、3-ブチン酸エチル、3-ブチン酸プロピル、3-ブチン酸ビニル、3-ブチン酸2-プロペニル、3-ブチン酸2-ブテニル、3-ブチン酸3-ブテニル、2-ペンチン酸メチル、2-ペンチン酸エチル、2-ペンチン酸プロピル、2-ペンチン酸ビニル、2-ペンチン酸2-プロペニル、2-ペンチン酸2-ブテニル、2-ペンチン酸3-ブテニル、3-ペンチン酸メチル、3-ペンチン酸エチル、3-ペンチン酸プロピル、3-ペンチン酸ビニル、3-ペンチン酸2-プロペニル、3-ペンチン酸2-ブテニル、3-ペンチン酸3-ブテニル、4-ペンチン酸メチル、4-ペンチン酸エチル、4-ペンチン酸プロピル、4-ペンチン酸ビニル、4-ペンチン酸2-プロペニル、4-ペンチン酸2-ブテニル、4-ペンチン酸3-ブテニル等のモノカルボン酸エステル、フマル酸エステル、トリメチル酢酸メチル、トリメチル酢酸エチル;
2-ブチン-1,4-ジオールジアセテート、2-ブチン-1,4-ジオールジプロピオネート、2-ブチン-1,4-ジオールジブチレート、2-ブチン-1,4-ジオールジベンゾエート、2-ブチン-1,4-ジオールジシクロヘキサンカルボキシレート、ヘキサヒドロベンゾ[1,3,2]ジオキサチオラン-2-オキシド(1,2-シクロヘキサンジオール、2,2-ジオキシド-1,2-オキサチオラン-4-イルアセテート、2,2-ジオキシド-1,2-オキサチオラン-4-イルアセテート等のジカルボン酸エステル;
シュウ酸メチル2-プロピニル、シュウ酸エチル2-プロピニル、シュウ酸プロピル2-プロピニル、シュウ酸2-プロピニルビニル、シュウ酸アリル2-プロピニル、シュウ酸ジ-2-プロピニル、シュウ酸2-ブチニルメチル、シュウ酸2-ブチニルエチル、シュウ酸2-ブチニルプロピル、シュウ酸2-ブチニルビニル、シュウ酸アリル2-ブチニル、シュウ酸ジ-2-ブチニル、シュウ酸3-ブチニルメチル、シュウ酸3-ブチニルエチル、シュウ酸3-ブチニルプロピル、シュウ酸3-ブチニルビニル、シュウ酸アリル3-ブチニル、シュウ酸ジ-3-ブチニル等のシュウ酸ジエステル;
メチル(2-プロピニル)(ビニル)ホスフィンオキシド、ジビニル(2-プロピニル)ホスフィンオキシド、ジ(2-プロピニル)(ビニル)ホスフィンオキシド、ジ(2-プロペニル)2(-プロピニル)ホスフィンオキシド、ジ(2-プロピニル)(2-プロペニル)ホスフィンオキシド、ジ(3-ブテニル)(2-プロピニル)ホスフィンオキシド、及びジ(2-プロピニル)(3-ブテニル)ホスフィンオキシド等のホスフィンオキシド;
メチル(2-プロペニル)ホスフィン酸2-プロピニル、2-ブテニル(メチル)ホスフィン酸2-プロピニル、ジ(2-プロペニル)ホスフィン酸2-プロピニル、ジ(3-ブテニル)ホスフィン酸2-プロピニル、メチル(2-プロペニル)ホスフィン酸1,1-ジメチル-2-プロピニル、2-ブテニル(メチル)ホスフィン酸1,1-ジメチル-2-プロピニル、ジ(2-プロペニル)ホスフィン酸1,1-ジメチル-2-プロピニル、及びジ(3-ブテニル)ホスフィン酸1,1-ジメチル-2-プロピニル、メチル(2-プロピニル)ホスフィン酸2-プロペニル、メチル(2-プロピニル)ホスフィン酸3-ブテニル、ジ(2-プロピニル)ホスフィン酸2-プロペニル、ジ(2-プロピニル)ホスフィン酸3-ブテニル、2-プロピニル(2-プロペニル)ホスフィン酸2-プロペニル、及び2-プロピニル(2-プロペニル)ホスフィン酸3-ブテニル等のホスフィン酸エステル;
2-プロペニルホスホン酸メチル2-プロピニル、2-ブテニルホスホン酸メチル(2-プロピニル)、2-プロペニルホスホン酸(2-プロピニル)(2-プロペニル)、3-ブテニルホスホン酸(3-ブテニル)(2-プロピニル)、2-プロペニルホスホン酸(1,1-ジメチル-2-プロピニル)(メチル)、2-ブテニルホスホン酸(1,1-ジメチル-2-プロピニル)(メチル)、2-プロペニルホスホン酸(1,1-ジメチル-2-プロピニル)(2-プロペニル)、及び3-ブテニルホスホン酸(3-ブテニル)(1,1-ジメチル-2-プロピニル)、メチルホスホン酸(2-プロピニル)(2-プロペニル)、メチルホスホン酸(3-ブテニル)(2-プロピニル)、メチルホスホン酸(1,1-ジメチル-2-プロピニル)(2-プロペニル)、メチルホスホン酸(3-ブテニル)(1,1-ジメチル-2-プロピニル)、エチルホスホン酸(2-プロピニル)(2-プロペニル)、エチルホスホン酸(3-ブテニル)(2-プロピニル)、エチルホスホン酸(1,1-ジメチル-2-プロピニル)(2-プロペニル)、及びエチルホスホン酸(3-ブテニル)(1,1-ジメチル-2-プロピニル)等のホスホン酸エステル;
リン酸(メチル)(2-プロペニル)(2-プロピニル)、リン酸(エチル)(2-プロペニル)(2-プロピニル)、リン酸(2-ブテニル)(メチル)(2-プロピニル)、リン酸(2-ブテニル)(エチル)(2-プロピニル)、リン酸(1,1-ジメチル-2-プロピニル)(メチル)(2-プロペニル)、リン酸(1,1-ジメチル-2-プロピニル)(エチル)(2-プロペニル)、リン酸(2-ブテニル)(1,1-ジメチル-2-プロピニル)(メチル)、及びリン酸(2-ブテニル)(エチル)(1,1-ジメチル-2-プロピニル)等のリン酸エステル。
R61、R62は、一価の炭化水素基であれば、その種類は特に制限されない。例えば、脂肪族炭化水素基であっても芳香族炭化水素基であってもよく、脂肪族炭化水素基と芳香族炭化水素基とが結合したものであってもよい。脂肪族炭化水素基は、飽和炭化水素基であってもよく、不飽和結合(炭素-炭素二重結合又は炭素-炭素三重結合)を含んでいてもよい。また、脂肪族炭化水素基は、鎖状であっても環状であってもよく、鎖状の場合は、直鎖状であっても分岐鎖状であってもよい。更には、鎖状と環状とが結合したものであってもよい。なお、R61及びR62は互いに同一であってもよく、異なっていてもよい。
フルオロベンゼン、ジフルオロベンゼン、ヘキサフルオロベンゼン、ベンゾトリフルオライド、モノフルオロベンゼン、1-フルオロ-2-シクロヘキシルベンゼン、1-フルオロ-4-tert-ブチルベンゼン、1-フルオロ-3-シクロヘキシルベンゼン、1-フルオロ-2-シクロヘキシルベンゼン、フッ素化ビフェニル等の含フッ素芳香族化合物;
エリスリタンカーボネート、スピロ-ビス-ジメチレンカーボネート、メトキシエチル-メチルカーボネート等のカーボネート化合物;
ジオキソラン、ジオキサン、2,5,8,11-テトラオキサドデカン、2,5,8,11,14-ペンタオキサペンタデカン、エトキシメトキシエタン、トリメトキシメタン、グライム、エチルモノグライム等のエーテル系化合物;
ジメチルケトン、ジエチルケトン、3-ペンタノン等のケトン系化合物;
2-アリル無水コハク酸等の酸無水物;
シュウ酸ジメチル、シュウ酸ジエチル、シュウ酸エチルメチル、シュウ酸ジ(2-プロピニル)、シュウ酸メチル2-プロピニル、コハク酸ジメチル、グルタル酸ジ(2-プロピニル)、ギ酸メチル、ギ酸エチル、ギ酸2-プロピニル、2-ブチン-1,4-ジイルジホルメート、メタクリル酸2-プロピニル、マロン酸ジメチル等のエステル化合物;
アセトアミド、N-メチルホルムアミド、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド等のアミド系化合物;
硫酸エチレン、硫酸ビニレン、亜硫酸エチレン、フルオロスルホン酸メチル、フルオロスルホン酸エチル、メタンスルホン酸メチル、メタンスルホン酸エチル、ブスルファン、スルホレン、ジフェニルスルホン、N,N-ジメチルメタンスルホンアミド、N,N-ジエチルメタンスルホンアミド、ビニルスルホン酸メチル、ビニルスルホン酸エチル、ビニルスルホン酸アリル、ビニルスルホン酸プロパルギル、アリルスルホン酸メチル、アリルスルホン酸エチル、アリルスルホン酸アリル、アリルスルホン酸プロパルギル、1,2-ビス(ビニルスルホニロキシ)エタン、無水プロパンジスルホン酸、無水スルホ酪酸、無水スルホ安息香酸、無水スルホプロピオン酸、無水エタンジスルホン酸、メチレンメタンジスルホネート、メタンスルホン酸2-プロピニル、ペンテンサルファイト、ペンタフルオロフェニルメタンスルホネート、プロピレンサルフェート、プロピレンサルファイト、プロパンサルトン、ブチレンサルファイト、ブタン-2,3-ジイルジメタンスルホネート、2-ブチン-1,4-ジイルジメタンスルホネート、ビニルスルホン酸2-プロピニル、ビス(2-ビニルスルホニルエチル)エーテル、5-ビニル-ヘキサヒドロ-1,3,2-ベンゾジオキサチオール-2-オキシド、2-(メタンスルホニルオキシ)プロピオン酸2-プロピニル、5,5-ジメチル-1,2-オキサチオラン-4-オン2,2-ジオキシド、3-スルホ-プロピオン酸無水物トリメチレンメタンジスルホネート2-メチルテトラヒドロフラン、トリメチレンメタンジスルホネート、テトラメチレンスルホキシド、ジメチレンメタンジスルホネート、ジフルオロエチルメチルスルホン、ジビニルスルホン、1,2-ビス(ビニルスルホニル)エタン、エチレンビススルホン酸メチル、エチレンビススルホン酸エチル、エチレンサルフェート、チオフェン1-オキシド等の含硫黄化合物;
1-メチル-2-ピロリジノン、1-メチル-2-ピペリドン、3-メチル-2-オキサゾリジノン、1,3-ジメチル-2-イミダゾリジノン及びN-メチルスクシンイミド、ニトロメタン、ニトロエタン、エチレンジアミン等の含窒素化合物;
亜リン酸トリメチル、亜リン酸トリエチル、亜リン酸トリフェニル、リン酸トリメチル、リン酸トリエチル、リン酸トリフェニル、メチルホスホン酸ジメチル、エチルホスホン酸ジエチル、ビニルホスホン酸ジメチル、ビニルホスホン酸ジエチル、ジエチルホスホノ酢酸エチル、ジメチルホスフィン酸メチル、ジエチルホスフィン酸エチル、トリメチルホスフィンオキシド、トリエチルホスフィンオキシド、リン酸ビス(2,2-ジフルオロエチル)2,2,2-トリフルオロエチル、リン酸ビス(2,2,3,3-テトラフルオロプロピル)2,2,2-トリフルオロエチル、リン酸ビス(2,2,2-トリフルオロエチル)メチル、リン酸ビス(2,2,2-トリフルオロエチル)エチル、リン酸ビス(2,2,2-トリフルオロエチル)2,2-ジフルオロエチルリン酸ビス(2,2,2-トリフルオロエチル)2,2,3,3-テトラフルオロプロピル、リン酸トリブチル、リン酸トリス(2,2,2-トリフルオロエチル)、リン酸トリス(1,1,1,3,3,3-ヘキサフルオロプロパン-2-イル)、リン酸トリオクチル、リン酸2-フェニルフェニルジメチル、リン酸2-フェニルフェニルジエチル、リン酸(2,2,2-トリフルオロエチル)(2,2,3,3-テトラフルオロプロピル)メチル、メチル2-(ジメトキシホスホリル)アセテート、メチル2-(ジメチルホスホリル)アセテート、メチル2-(ジエトキシホスホリル)アセテート、メチル2-(ジエチルホスホリル)アセテート、メチレンビスホスホン酸メチル、メチレンビスホスホン酸エチル、エチレンビスホスホン酸メチル、エチレンビスホスホン酸エチル、ブチレンビスホスホン酸メチル、ブチレンビスホスホン酸エチル、酢酸2-プロピニル2-(ジメトキシホスホリル)、酢酸2-プロピニル2-(ジメチルホスホリル)、酢酸2-プロピニル2-(ジエトキシホスホリル)、酢酸2-プロピニル2-(ジエチルホスホリル)、リン酸トリス(トリメチルシリル)、リン酸トリス(トリエチルシリル)、リン酸トリス(トリメトキシシリル)、亜リン酸トリス(トリメチルシリル)、亜リン酸トリス(トリエチルシリル)、亜リン酸トリス(トリメトキシシリル)、ポリリン酸トリメチルシリル等の含燐化合物;
ホウ酸トリス(トリメチルシリル)、ホウ酸トリス(トリメトキシシリル)等の含ホウ素化合物;
ジメトキシアルミノキシトリメトキシシラン、ジエトキシアルミノキシトリエトキシシラン、ジプロポキシアルミノキシトリエトキシシラン、ジブトキシアルミノキシトリメトキシシラン、ジブトキシアルミノキシトリエトキシシラン、チタンテトラキス(トリメチルシロキシド)、チタンテトラキス(トリエチルシロキシド)、テトラメチルシラン等のシラン化合物;
等が挙げられる。これらは1種を単独で用いても、2種以上を併用してもよい。これらの助剤を添加することにより、高温保存後の容量維持特性やサイクル特性を向上させやすい。
で示される含フッ素ラクトンが挙げられる。
で示される含フッ素ラクトン等も挙げられる。
で示される5員環構造が、合成が容易である点、化学的安定性が良好な点から好ましく挙げられ、更には、AとBの組合せにより、後記式(F):
で示される含フッ素ラクトンと、後記式(G):
で示される含フッ素ラクトンがある。
Rf3-O-Rf4 (I)
(式中、Rf3及びRf4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、Rf3及びRf4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しやすいとともに、高温高電圧での安定性、安全性が向上しやすい。
Rf5COO-M+ (30)
(式中、Rf5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、後記式(40):
Rf6SO3 -M+ (40)
(式中、Rf6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スルホン酸塩等が好ましい。
A-(D)-B (101)
[式中、Dは式(201):
-(D1)n-(FAE)m-(AE)p-(Y)q- (201)
(式中、D1は、式(2a):
で示される側鎖に含フッ素エーテル基を有するエーテル単位;
FAEは、式(2b):
で示される側鎖にフッ素化アルキル基を有するエーテル単位;
AEは、式(2c):
で示されるエーテル単位;
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)を示す。]
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。
正極は、正極活物質を含む正極活物質層と、集電体とから構成することができる。
式: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: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: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。
負極は、負極活物質を含む負極活物質層と、集電体とから構成される。
LixTiyMzO4
[式中、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。
(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。
本開示の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。
電極群は、前記の正極板と負極板とを前記のセパレータを介してなる積層構造のもの、及び前記の正極板と負極板とを前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。
前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。
(含フッ素カルボン酸塩化合物)
化合物F:HCF2COOLi
化合物G:CF3COOLi
化合物H:CFH2COOLi
化合物I:CF3CH2COOLi
化合物J:HCF2CF2COOLi。
鎖状カーボネート
(a):ジメチルカーボネート
(b):エチルメチルカーボネート
(c):ジエチルカーボネート
(d):CF3CH2OCOOCH3。
EC:エチレンカーボネート
PC:プロピレンカーボネート
FEC:4-フルオロ-1,3-ジオキソラン-2-オン。
各実施例及び比較例4のジフロロ酢酸リチウムの水分測定は、ドライルーム(露点-40℃以下)中において、カールフィッシャー法により、行った。前記比較例4としては、購入品(APOLLO SCIENTIFIC社、Lithium difluoroacetate)を用いた。
反応器にジフロロ酢酸エチル(100 g, 0.8065 mol)を添加し、及び室温で撹拌した。水酸化リチウム(17.4 g, 0.7258 mol)を分割添加し、及び反応が終了するまで室温で撹拌した。反応終了後、減圧下、反応混合物から液体媒体を留去し、含フッ素カルボン酸塩化合物として化合物F(ジフロロ酢酸リチウム)(64.9 g, 88%収率)(水分量:2340ppm)を得た。
反応器にジフロロ酢酸エチル(100 g, 0.8065 mol)とエタノール(200 g)を添加し、室温で撹拌した。その温度を70℃以下に維持しながら、水酸化リチウム(17.4 g, 0.7258 mol)を分割添加し、及び反応が終了するまで室温で撹拌した。反応終了後、減圧下、反応混合物から液体媒体を留去し、含フッ素カルボン酸塩化合物として化合物F(ジフロロ酢酸リチウム)(62.3 g, 85%収率)(水分量:1462ppm)を得た。
実施例1に準じて、表1に記載の、様々な水分量を有する化合物F(ジフロロ酢酸リチウム)を得た。水分量は、共沸脱水の実施及び/又は微量の水の添加により、調製した。
ジフロロ酢酸エチルに代えてトリフルオロ酢酸エチルを使用したこと以外は、実施例2と同様の方法により化合物Gを製造した。
ジフロロ酢酸エチルに代えてモノフルオロ酢酸エチルを使用したこと以外は、実施例2と同様の方法により化合物Hを製造した。
ジフロロ酢酸エチルに代えて3-トリフルオロプロピオン酸エチルを使用し、及びエタノールに代えてテトラヒドロフランを使用したこと以外は、実施例2と同様の方法により化合物Iを製造した。
ジフロロ酢酸エチルに代えて2-ジフルオロ-3-ジフルオロプロピオン酸エチルを使用したこと、及びエタノールに代えてアセトニトリルを使用したこと以外は、実施例2と同様の方法により化合物Jを製造した。
実施例1~21及び比較例4のジフロロ酢酸リチウムの水分測定をドライルーム(露点 -40℃以下)にてカールフィッシャー法により、行った。前記比較例4としては、購入品(APOLLO SCIENTIFIC社、Lithium difluoroacetate)を用いた。結果は、表1の「水分量質量」の欄に示した。
以下のようにして実施例1~21の電解液、及び比較例1~4の電解液(このうち、表1に示す通り、比較例1~3(参考例)には、含フッ素カルボン酸塩化合物を添加しなかった。)を調製し、得られた各電解液を用いてリチウムイオン二次電池を作製し、それぞれの抵抗増加率、サイクル容量保持率を評価した。
乾燥アルゴン雰囲気下で、鎖状カーボネートと環状カーボネートとを表1に示す割合で混合し、この溶液に、前記各実施例で得られた含フッ素カルボン酸塩化合物を表1に示す量添加し、更に、乾燥したLiPF6を1.2モル/リットルの濃度となるように添加して、非水電解液を得た。含フッ素カルボン酸塩化合物の配合割合は、電解液に対する質量%で表した。
負極活物質として人造黒鉛粉末、増粘剤としてカルボキシルメチルセルロースナトリウムの水性ディスパージョン(カルボキシメチルセルロースナトリウムの濃度1質量%)、結着剤としてスチレン-ブタジエンゴムの水性ディスパージョン(スチレン-ブタジエンゴムの濃度50質量%)を用い、これらを水溶媒中で混合してスラリー状とした負極合剤スラリーを準備した。負極活物質、増粘剤、結着剤の固形分比は、98.1/0.9/1.0(質量%比)とした。厚さ20μmの銅箔に均一に塗布、乾燥した後、プレス機により圧縮形成して、負極とした。
正極活物質としてLiNi0.6Mn0.2Co0.2O2、導電材としてアセチレンブラック、結着剤としてポリフッ化ビニリデン(PVdF)のN-メチル-2-ピロリドンディパージョンを用い、これらを混合してスラリー状とした正極合剤スラリーを準備した。正極活物質、導電材、結着剤の固形分比は、97/1.5/1.5(質量%比)とした。厚さ20μmのアルミ箔集電体上に、得られた正極合剤スラリーを均一に塗布し、乾燥した後、プレス機により圧縮成形して、正極とした。
上記のとおり製造した負極、正極及びポリエチレン製セパレータを負極、セパレータ、正極の順に積層して、電池要素を作製した。
上記で製造した二次電池を、板で挟み加圧した状態で、45℃において、0.2Cに相当する電流で4.2Vまで定電流-定電圧充電(以下、CC/CV充電と表記する。)(0.1Cカット)した後、0.2Cの定電流で3Vまで放電し、これを1サイクルとして、3サイクル目の放電容量から初期放電容量を求めた。ここで、1Cとは電池の基準容量を1時間で放電する電流値を表わし、例えば、0.2Cとはその1/5の電流値を表わす。再度サイクルを行い、600サイクル後の放電容量をサイクル後の容量とした。初期放電容量に対する600サイクル後の放電容量の割合を求め、これをサイクル容量保持率(%)とした。
(600サイクル後の放電容量)÷(初期放電容量)×100=サイクル容量維持率(%)
(抵抗増加率)
所定の充放電条件(0.2C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)で行う充放電サイクルを1サイクルとし、3サイクル後の抵抗と600サイクル後の抵抗とを測定した。測定温度は25℃とした。下記式に基づき、600サイクル後の抵抗増加率を求めた。
Claims (16)
- 式(P1):(B1f)mp(A1)np
[式中、
B1fは、RfCOOであり、
Rfは、1個以上のフッ素原子を有する炭化水素であり、
A1は、H以外の基であり、
mpは、(A1の価数)×np/(B1fの価数)の数であって、且つ1又は2であり、
npは、(B1fの価数)×mp/(A1の価数)の数であって、且つ1であり、
A1の価数は、1又は2であり、及び
B1fの価数は、1である。]
で表される化合物
の製造方法であって、
式(S1):(B1f)(R1)
[式中、
B1fは、前記と同意義であり、及び
R1は、有機基である。
ただし、R1は、A1とは異なる基である。]
で表される化合物を、
式(S2):(A1)ms2(B2)ns2
[式中、
A1は、前記と同意義であり、
B2は、OH、CO3、又はHCO3であり、
ms2は、(B2の価数)×ns2/(A1の価数)の数であって、且つ1又は2であり、及び
ns2は、(A1の価数)×ms2/(B2の価数)であって、且つ1又は2である。]
で表される化合物、又はその水和物と、
反応させる工程A
を含む、製造方法。 - A1は、金属原子、又はアンモニウムである、請求項1に記載の製造方法。
- 前記工程Aで副生成する、
式(P2):(R1)op(B2)
[式中、
B2及びR1は、前記と同意義であり、及び
opは、(B2の価数)/(R1の価数)の数であって、且つ1又は2である。]
で表される化合物を、除去する工程B
を更に含む、請求項1又は2に記載の製造方法。 - Rfが、1個以上のフッ素原子を有するC1-6アルキル基である、請求項1~3のいずれか一項に記載の製造方法。
- Rfが、2個以上のフッ素原子を有するC1-3アルキル基である、請求項1~4のいずれか一項に記載の製造方法。
- A1は、アルカリ金属原子である、請求項1~5のいずれか一項に記載の製造方法。
- A1は、Liである、請求項1~6のいずれか一項に記載の製造方法。
- B2は、OHである、請求項1~7のいずれか一項に記載の製造方法。
- 式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、金属原子である。]
で表される化合物、及び
前記式(P1A)で表される化合物に対して、0~50000質量ppmの水
を含有する、
電気化学デバイス用添加剤。 - 請求項9に記載の電気化学デバイス用添加剤を含有する、電解液。
- 請求項10に記載の電解液を備える、電気化学デバイス。
- 請求項10に記載の電解液を備える、リチウムイオン二次電池。
- 水分含有量が、50000質量ppm以下である、
式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物。 - 式(P1A):RfCOOAd
[式中、
Rfは、1個以上のフッ素原子を有する有機基であり、及び
Adは、Li原子である。]
で表される化合物、及び
前記式(P1)で表される化合物に対して50000質量ppm以下の水
を含有する組成物。 - 請求項1~8のいずれか一項に記載の製造方法で製造された、
請求項13に記載の化合物。 - 請求項1~8のいずれか一項に記載の製造方法で製造された、
請求項14に記載の組成物。
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