CN110880619B - Electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using same - Google Patents
Electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using same Download PDFInfo
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- CN110880619B CN110880619B CN201911249839.8A CN201911249839A CN110880619B CN 110880619 B CN110880619 B CN 110880619B CN 201911249839 A CN201911249839 A CN 201911249839A CN 110880619 B CN110880619 B CN 110880619B
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- nonaqueous electrolyte
- electrolyte battery
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- 239000011255 nonaqueous electrolyte Substances 0.000 title claims abstract description 103
- 239000003792 electrolyte Substances 0.000 title claims abstract description 82
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- 239000002904 solvent Substances 0.000 claims abstract description 26
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 229910000077 silane Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052744 lithium Inorganic materials 0.000 claims description 22
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 21
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 229910052723 transition metal Inorganic materials 0.000 claims description 19
- 150000003624 transition metals Chemical class 0.000 claims description 19
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 9
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
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- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 5
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- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 4
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- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 3
- RDOGTTNFVLSBKG-UHFFFAOYSA-N 1,2-difluoro-3-methoxybenzene Chemical compound COC1=CC=CC(F)=C1F RDOGTTNFVLSBKG-UHFFFAOYSA-N 0.000 claims description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 2
- QYIOFABFKUOIBV-UHFFFAOYSA-N 4,5-dimethyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1C QYIOFABFKUOIBV-UHFFFAOYSA-N 0.000 claims description 2
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 claims description 2
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- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
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- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 claims description 2
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 claims description 2
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- VCCATSJUUVERFU-UHFFFAOYSA-N sodium bis(fluorosulfonyl)azanide Chemical compound FS(=O)(=O)N([Na])S(F)(=O)=O VCCATSJUUVERFU-UHFFFAOYSA-N 0.000 claims description 2
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- YLKTWKVVQDCJFL-UHFFFAOYSA-N sodium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Na+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F YLKTWKVVQDCJFL-UHFFFAOYSA-N 0.000 claims description 2
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- 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 13
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- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- 229910010710 LiFePO Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 229910012513 LiSbF 6 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011331 needle coke Substances 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 239000010450 olivine Substances 0.000 description 1
- 229910052609 olivine Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000006253 pitch coke Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- 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
- H01M10/052—Li-accumulators
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- 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
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- 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
- H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
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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
- H01M10/0568—Liquid materials characterised by the solutes
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- 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
- H01M10/0569—Liquid materials characterised by the solvents
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- H01M2220/00—Batteries for particular applications
- H01M2220/20—Batteries in motive systems, e.g. vehicle, ship, plane
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2220/00—Batteries for particular applications
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- H01M2300/0017—Non-aqueous electrolytes
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- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
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Abstract
The present invention relates to an electrolyte for a nonaqueous electrolyte battery and a nonaqueous electrolyte battery using the same. The present invention provides: an electrolyte for a nonaqueous electrolyte battery which has a high average discharge voltage of 30 ℃ or less, has excellent low-temperature output characteristics, and can exhibit excellent cycle characteristics and storage characteristics at a high temperature of 50 ℃ or more; and a nonaqueous electrolyte battery using the same. The electrolyte for a nonaqueous electrolyte battery of the present invention comprises: a nonaqueous solvent, a solute, at least 1 silane compound represented by the following general formula (1) as a compound 1, and a fluorine-containing compound represented by, for example, the following general formula (3) as a compound 2: si (R) 1 ) a (R 2 ) 4‑a (1)
Description
The present application is a divisional application of application number 201680010967.5, entitled "electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using the same", which is filed on day 2016, month 2 and 18.
Technical Field
The present invention relates to: an electrolyte for a nonaqueous electrolyte battery containing a specific silane compound and a salt having a fluorophosphoryl structure and/or a fluorosulfonyl structure, and a nonaqueous electrolyte battery using the same.
Background
In recent years, attention has been paid to a power storage system for applications requiring high energy density for information-related devices or communication devices, i.e., small-sized devices such as personal computers, video cameras, digital still cameras, and cellular phones, and a power storage system for applications requiring power for large-sized devices such as electric vehicles, hybrid vehicles, fuel cell vehicle auxiliary power supplies, and electric power storage. A nonaqueous electrolyte battery such as a lithium ion battery, a lithium ion capacitor, and a sodium ion battery is being actively developed as one of its candidates.
Although many of these nonaqueous electrolyte batteries have been put to practical use, the respective characteristics are not satisfactory for various purposes. In particular, in the case of in-vehicle applications such as electric vehicles, high input/output characteristics are required even in cold weather, and thus improvement of low-temperature characteristics is important. In addition to the low-temperature characteristics, characteristics such as a small decrease in capacity even when repeatedly charged and discharged under a high-temperature environment (high-temperature cycle characteristics) and a small self-discharge even when left in a fully charged state for a long period of time under a high-temperature environment (high-temperature storage characteristics) are also demanded.
Up to now, as means for improving the high-temperature characteristics and battery characteristics (cycle characteristics) at the time of repeated charge and discharge of a nonaqueous electrolyte battery, optimization of various battery components represented by active materials of a positive electrode and a negative electrode has been studied. The nonaqueous electrolyte related art is also incorporated therein, and various additives have been proposed to suppress degradation due to decomposition of the electrolyte on the surfaces of active positive and negative electrodes. For example, patent document 1 proposes a method of improving battery characteristics by adding vinylene carbonate to an electrolyte. However, although the battery characteristics at high temperatures are improved, the increase in internal resistance is remarkable, and the low-temperature characteristics are problematic. Further, studies have been made on adding a silicon compound to an electrolyte solution, and for example, patent documents 2 to 6 propose the following methods: by adding a silicon compound such as a silicone compound or a fluorosilane compound to a nonaqueous electrolyte solution, the cycle characteristics of the nonaqueous electrolyte battery are improved, and the increase in internal resistance is suppressed, thereby improving the high-temperature storage characteristics and the low-temperature characteristics, and the following method is proposed in patent document 7: by adding the fluorosilane compound and the difluorophosphoric acid compound, the low-temperature characteristics of the nonaqueous electrolyte battery are improved. In addition, the addition of a salt having a phosphoryl group or a sulfonyl group to an electrolyte solution has been studied, and for example, the following methods have been proposed: a method of improving high-temperature cycle characteristics and high-temperature storage characteristics by combining a specific sulfonimide salt, a phosphorylimide salt, and an oxalate complex (patent document 8); a method of improving cycle characteristics and output characteristics by combining a specific fluorophosphate with a sulfonimide salt (patent document 9).
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2000-123867
Patent document 2: japanese patent laid-open No. 8-078053
Patent document 3: japanese patent laid-open No. 2002-033127
Patent document 4: japanese patent laid-open No. 2004-039510
Patent document 5: japanese patent laid-open No. 2004-087459
Patent document 6: japanese patent laid-open No. 2008-181831
Patent document 7: japanese patent laid-open No. 2007-149556
Patent document 8: japanese patent application laid-open No. 2013-051122
Patent document 9: japanese patent laid-open publication No. 2013-030465
Patent document 10: japanese patent laid-open No. 10-139784
Patent document 11: japanese patent application laid-open No. 2008-222484
Non-patent literature
Non-patent document 1: tetrahedron,42 (11), 2821-2829 (1986)
Non-patent document 2: journal of the American Chemical Society,72, 4956-4958, (1950)
Non-patent document 3: faraday Discussion,145, 281-299, (2010)
Disclosure of Invention
Problems to be solved by the invention
There is still room for improvement in low-temperature output characteristics, high-temperature cycle characteristics, and high-temperature storage characteristics obtained from the battery disclosed in the prior art document. In particular, there are the following problems: at low temperatures, the internal resistance of the battery increases, which results in a large voltage drop during discharge, and it is difficult to obtain a sufficient discharge voltage. Further, when the silane compound has si—f bond or si—o bond, there is a problem that the internal resistance of the battery increases greatly and the output characteristics decrease greatly. The present invention provides: an electrolyte for a nonaqueous electrolyte battery which has a high average discharge voltage of 30 ℃ or less, has excellent low-temperature output characteristics, and can exhibit excellent cycle characteristics and storage characteristics at a high temperature of 50 ℃ or more; and a nonaqueous electrolyte battery using the same.
Solution for solving the problem
The present inventors have conducted intensive studies to solve the above problems, and as a result, found that: the nonaqueous electrolyte for nonaqueous electrolyte battery containing a nonaqueous solvent and a solute comprises:
a specific silane compound, and,
at least 1 kind selected from the group consisting of fluorine-containing compounds of specific structures (fluorophosphates of specific structures, fluorophosphoryl structures and/or imide salts of fluorosulfonyl structures), whereby when the electrolyte is used in a nonaqueous electrolyte battery, excellent low-temperature characteristics, high-temperature cycle characteristics and high-temperature storage characteristics can be exhibited, and the present invention has been completed.
That is, the present invention provides an electrolyte for a nonaqueous electrolyte battery (hereinafter, sometimes simply referred to as "nonaqueous electrolyte" or "electrolyte") characterized by,
at least comprises: a nonaqueous solvent, a solute, at least 1 silane compound represented by the following general formula (1) as a 1 st compound, and at least 1 selected from the group consisting of fluorine-containing compounds represented by the following general formulas (2) to (9) as a 2 nd compound.
Si(R 1 ) a (R 2 ) 4-a (1)
[ in the general formula (1), R 1 Each independently of the other represents a group having a carbon-carbon unsaturated bond. R is R 2 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms. These groups optionally have fluorine atoms and/or oxygen atoms. a is 2 to 4. In the general formulae (2) to (4) and (6) to (8), R 3 ～R 6 Each independently of the other is an organic group selected from a fluorine atom, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and a fluorine atom, an oxygen atom and an unsaturated bond may be present in the organic group. In the general formulae (4), (5), (8) and (9), X 1 And X 2 Each independently of the other is a fluorine atom, an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and a fluorogen may be present in the organic group Son, oxygen atom, unsaturated bond. The general formulae (2) to (9) include at least one P-F bond and/or at least one S-F bond. M is M 1 、M 2 Each, independently of the others, is a proton, a metal cation or an onium cation.]
In the electrolyte for a nonaqueous electrolyte battery of the present invention, it is important that the 1 st compound and the 2 nd compound are contained together. This is because when these compounds are contained together, the electrolyte is used in a nonaqueous electrolyte battery, the average discharge voltage is high at-30 ℃ or lower, and the electrolyte exhibits excellent low-temperature output characteristics and excellent cycle characteristics and storage characteristics at high temperatures of 50 ℃ or higher.
The amount of the compound 1 to be added is preferably in the range of 0.001 to 10.0 mass% relative to the total amount of the electrolyte for a nonaqueous electrolyte battery.
The amount of the compound 2 to be added is preferably in the range of 0.001 to 10.0 mass% relative to the total amount of the electrolyte for a nonaqueous electrolyte battery.
In addition, R of the above general formula (1) 1 The radicals indicated are preferably each, independently of one another, a radical selected from the group consisting of vinyl, allyl, 1-propenyl, 2-propenyl, ethynyl and 2-propynyl.
In addition, R of the above general formula (1) 2 The radicals indicated are preferably each, independently of one another, selected from the group consisting of methyl ethyl, propyl, 2-trifluoroethyl 2, 3-tetrafluoropropyl group 1, 1-trifluoroisopropyl and 1, 3-hexafluoroisopropyl.
R of the general formulae (2) to (4) and (6) to (8) 3 ～R 6 The organic group is preferably a fluorine atom, a linear or branched alkoxy group having a fluorine atom and having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms.
In addition, it is more preferable that, the alkoxy group is selected from the group consisting of 2, 2-trifluoroethoxy, 2, 3-tetrafluoropropoxy 1, 1-trifluoroisopropoxy and 1, 3-hexafluoroisopropoxy, the alkenyloxy group is selected from the group consisting of 1-propenyloxy group, 2-propenyloxy group and 3-butenyloxy group, and the alkynyloxy group is selected from the group consisting of 2-propynyloxy group and 1, 1-dimethyl-2-propynyloxy group.
In addition, X of the above general formulae (4), (5), (8) and (9) 1 And X 2 Preferably a fluorine atom, an organic group selected from the group consisting of a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms and an alkynyloxy group having 2 to 10 carbon atoms.
Further, it is preferable that the alkoxy group is selected from the group consisting of methoxy, ethoxy and propoxy, the alkenyloxy group is selected from the group consisting of 1-propenyloxy, 2-propenyloxy and 3-butenyloxy, and the alkynyloxy group is selected from the group consisting of 2-propynyloxy and 1, 1-dimethyl-2-propynyloxy.
M in the general formulae (2) to (9) 1 And M 2 Preferably at least one cation selected from the group consisting of lithium ion, sodium ion, potassium ion, tetraalkylammonium ion and tetraalkylphosphonium ion.
The solute is preferably selected from lithium hexafluorophosphate (LiPF) 6 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium bis (trifluoromethanesulfonyl) imide (LiN (CF) 3 SO 2 ) 2 ) Lithium bis (fluorosulfonyl) imide (LiN (FSO) 2 ) 2 ) Lithium bis (difluorophosphoryl) imide (LiN (POF) 2 ) 2 ) Sodium hexafluorophosphate (NaPF) 6 ) Sodium tetrafluoroborate (NaBF) 4 ) Sodium bis (trifluoromethanesulfonyl) imide (NaN (CF) 3 SO2) 2 ) Sodium bis (fluorosulfonyl) imide (NaN (FSO) 2 ) 2 ) And sodium bis (difluorophosphoryl) imide (NaN (POF) 2 ) 2 ) At least one solute from the group consisting of.
The nonaqueous solvent is preferably at least one nonaqueous solvent selected from the group consisting of cyclic carbonates, chain carbonates, cyclic esters, chain esters, cyclic ethers, chain ethers, sulfone compounds, sulfoxide compounds, and ionic liquids.
The present invention also provides a nonaqueous electrolyte battery (hereinafter, sometimes simply referred to as a "nonaqueous battery" or "battery") including at least: a positive electrode, a negative electrode, a separator, and the above-mentioned electrolyte for nonaqueous electrolyte battery.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, there may be provided: when used in a nonaqueous electrolyte battery, the electrolyte for a nonaqueous electrolyte battery has a high average discharge voltage of-30 ℃ or lower, excellent low-temperature output characteristics, and excellent cycle characteristics and storage characteristics at a high temperature of 50 ℃ or higher; and a nonaqueous electrolyte battery using the same.
Detailed Description
The present invention will be described in detail below, and the technical features described below are examples of embodiments of the present invention, and the present invention is not limited to these specific matters. Various modifications may be made within the scope of the gist thereof.
The electrolyte for a nonaqueous electrolyte battery of the present invention is characterized by comprising: at least comprises: a nonaqueous solvent, a solute, at least 1 silane compound represented by the above general formula (1) as a 1 st compound, and at least 1 selected from the group consisting of fluorine-containing compounds represented by the above general formulae (2) to (9) as a 2 nd compound.
The above-mentioned compound 1 has an effect of decomposing on both the positive electrode and the negative electrode to form a stable coating film and suppressing deterioration of the battery, but if the compound 1 is used alone, and the compound 1 and the compound 2 are not used in combination, there is a problem as follows: the film formed on the electrode strongly blocks the movement of lithium ions accompanying charge and discharge, and the low-temperature characteristics of the resulting nonaqueous electrolyte battery are significantly lowered. In addition, the high temperature cycle characteristics and the high temperature storage characteristics at a high temperature of 50 ℃ or higher are also insufficient.
A part of the compound 2 is decomposed also in the positive electrode and the negative electrode, and a coating film having good ion conductivity is formed on the surfaces of the positive electrode and the negative electrode. The coating film suppresses direct contact between the nonaqueous solvent and the solute and the electrode active material, prevents decomposition of the nonaqueous solvent and the solute, and suppresses deterioration of battery performance. However, when the compound 2 is used alone and the compound 1 and the compound 2 are not used in combination, the formed coating film component is small, and the high-temperature cycle characteristics and the high-temperature storage characteristics and the low-temperature characteristics at a high temperature of 50 ℃ or higher of the obtained nonaqueous electrolyte battery are insufficient.
In the electrolyte for a nonaqueous electrolyte battery of the present invention, the object of the present invention can be achieved by using the 1 st compound and the 2 nd compound in combination, whereby the high-temperature cycle characteristics, the high-temperature storage characteristics, and the low-temperature characteristics at a high temperature of 50 ℃ or higher are improved as compared with the case where the 1 st compound group is added alone. The details of the mechanism are not clear, but it is considered that the 1 st compound and the 2 nd compound coexist, whereby the 2 nd compound and the 1 st compound are positively decomposed on the positive electrode and the negative electrode together, and the ion conductivity is higher, and a coating film with more excellent durability is formed. This is thought to inhibit the decomposition of the solvent and solute at high temperature and inhibit the increase in resistance at low temperature. In particular, it is considered that a film having high lithium conductivity, that is, a film having low resistance (a film having good output characteristics) is formed by introducing a large amount of fluorophosphoryl structure and/or fluorosulfonyl structure into the film and shifting the charge of the formed film. Further, it is considered that the more sites containing unsaturated bonds are contained in the 1 st and 2 nd compounds, the more easily decomposition occurs on the positive electrode and the negative electrode, and the more easily a coating film excellent in durability is formed, and therefore the above effect becomes more excellent. Further, it is considered that by including a site (for example, a fluorine atom or a fluorine-containing alkoxy group) having high electron withdrawing property in the compound 2, the shift of charge becomes larger, and a film having a smaller resistance (a film having better output characteristics) is formed.
For the above reasons, it is assumed that: when the compound 1 and the compound 2 are used in combination, the average discharge voltage (output characteristic) at-30 ℃ or lower and the cycle characteristic and storage characteristic at a high temperature of 50 ℃ or higher are improved as compared with the case of using the compounds alone.
The electrolyte for a nonaqueous electrolyte battery of the present invention comprises: compound 1, compound 2, a nonaqueous organic solvent, and a solute. In addition, other additives generally known may be used in combination as required. Hereinafter, each constituent element of the electrolyte for a nonaqueous electrolyte battery of the present invention will be described in detail.
(with respect to the first Compound)
In the above general formula (1), R is 1 Examples of the group having a carbon-carbon unsaturated bond include alkenyl groups having 2 to 8 carbon atoms such as vinyl, allyl, 1-propenyl, 2-propenyl, isopropenyl, 2-butenyl, 1, 3-butadienyl and the like, and alkenyloxy groups derived from these groups; alkynyl groups having 2 to 8 carbon atoms such as ethynyl, 2-propynyl and 1, 1-dimethyl-2-propynyl, and alkynyloxy groups derived from these groups; aryl groups having 6 to 12 carbon atoms such as phenyl, tolyl, xylyl, and the like, and aryloxy groups derived from these groups. In addition, the above groups may have fluorine atoms and/or oxygen atoms. Among them, a group containing a carbon-carbon unsaturated bond having 6 or less carbon atoms is preferable. When the carbon number is more than 6, the resistance tends to be large when a coating film is formed on the electrode. Specifically, a group selected from the group consisting of vinyl, allyl, 1-propenyl, 2-propenyl, ethynyl, and 2-propynyl is preferable.
In addition, the number of the groups having carbon-carbon unsaturated bonds shown in a is preferably 2 to 4, and more preferably 3 to 4, in order to form a film on the electrode and further to achieve the object of the present invention.
In the general formula (1), R is 2 Examples of the alkyl group include alkyl groups having 1 to 12 carbon atoms such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and pentyl. The above group may have a fluorine atom and/or an oxygen atom (in the case of having an oxygen atom, the structure other than an alkoxy group is meant to be understood to be a structure in which an atom bonded to a silicon atom of the general formula (1) is not an oxygen atom). Wherein, the liquid crystal display device comprises a liquid crystal display device, in particular from the group consisting of methyl, ethyl, propyl, 2-trifluoroethyl, 2, 3-tetrafluoropropyl when a group selected from the group consisting of 1, 1-trifluoroisopropyl and 1, 3-hexafluoroisopropyl, a nonaqueous electrolyte battery having more excellent high-temperature cycle characteristics and high-temperature storage characteristics can be obtained without increasing the internal resistance of the battery, and is therefore preferable.
The lower limit of the suitable addition amount of the 1 st compound is 0.001 mass% or more, more preferably 0.01 mass% or more, still more preferably 0.1 mass% or more, and the upper limit is 10.0 mass% or less, more preferably 5.0 mass% or less, still more preferably 2.0 mass% or less, relative to the total amount of the electrolyte for a nonaqueous electrolyte battery. If the content is less than 0.001 mass%, the effect of improving the high-temperature storage characteristics of the nonaqueous electrolyte battery may not be sufficiently obtained. On the other hand, when the content exceeds 10.0 mass%, the internal resistance of the battery increases significantly, and the low-temperature output characteristics deteriorate. 1 st compound may be added, or a plurality of compounds may be added. In the present invention, the "total amount of the electrolyte for a nonaqueous electrolyte battery" refers to the total amount of the nonaqueous solvent, the solute, the 1 st compound and the 2 nd compound.
More specifically, examples of the silane compounds represented by the general formula (1) include the following compounds nos. 1 to 13. However, the silane compound used in the present invention is not limited by any of the following examples.
The silane compound represented by the general formula (1) can be produced by, for example, the method described in patent document 10 and non-patent document 1, as follows: a silicon compound having a silanol group or a hydrolyzable group is reacted with an organometallic reagent having a carbon-carbon unsaturated bond, and the silanol group or the hydrolyzable group in the silicon compound is substituted with a carbon-carbon unsaturated bond group to produce a silicon compound having a carbon-carbon unsaturated bond.
(with respect to the second Compound)
In the general formulae (2) to (9), it is important to include at least one P-F bond and/or S-F bond in order to achieve the object of the present invention. When the P-F bond or the S-F bond is not contained, the low temperature characteristics cannot be improved. The larger the number of P-F bonds and S-F bonds, the more excellent low-temperature characteristics can be obtained, and thus, it is preferable.
In the general formulae (2) to (9), M is 1 And M 2 Examples of the cations include protons, metal cations, and onium cations.The type of the electrolyte for a nonaqueous electrolyte battery and the nonaqueous electrolyte battery of the present invention is not particularly limited as long as the performance thereof is not impaired, and various substances may be selected from the above. Specific examples thereof include lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, barium, silver, copper, iron, and other metal cations, tetraalkylammonium, tetraalkylphosphonium, imidazolium derivatives, and other onium cations, and lithium ions, sodium ions, potassium ions, tetramethylammonium ions, tetraethylammonium ions, tetrabutylphosphonium ions, and the like are preferable from the viewpoint of exerting an effect of contributing to ion conduction in the nonaqueous electrolyte battery.
R as the above general formulae (2) to (4) and (6) to (8) 3 ～R 6 The alkoxy group as shown in the figure, examples thereof include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, pentyloxy, trifluoromethoxy, 2-difluoroethoxy, 2-trifluoroethoxy, 2, 3-tetrafluoropropoxy, 1-trifluoroisopropoxy and 1, 3-hexafluoroisopropoxy, examples of the alkenyloxy group include alkenyloxy groups having 2 to 10 carbon atoms such as ethyleneoxy group, 1-propyleneoxy group, 2-propyleneoxy group, isopropyleneoxy group, 2-butyleneoxy group, 3-butyleneoxy group and 1, 3-butyleneoxy group, fluorine-containing alkenyloxy group, examples of the alkynyloxy group include alkynyloxy groups and fluorinated alkynyloxy groups having 2 to 10 carbon atoms such as an ethynyloxy group, a 2-propynyloxy group and a 1, 1-dimethyl-2-propynyloxy group, examples of the cycloalkoxy group include cycloalkoxy groups and fluorinated cycloalkoxy groups having 3 to 10 carbon atoms such as a cyclopentyloxy group and a cyclohexyloxy group, examples of the cycloalkenyloxy group include cycloalkenyloxy groups and fluorinated cycloalkenyloxy groups having 3 to 10 carbon atoms such as a cyclopentyloxy group and a cyclohexene oxy group, examples of the aryloxy group include aryloxy groups and fluorinated aryloxy groups having 6 to 10 carbon atoms such as a phenoxy group, a tolyloxy group and a dimethylphenoxy group.
R of the above general formulae (2) to (4) and (6) to (8) 3 ～R 6 In the case of a fluorine atom or an alkoxy group having a fluorine atom, the ionic conductivity in a solution or a composition is preferably increased due to an increase in the degree of dissociation of ions by the strong electron withdrawing property. Furthermore, the above-mentioned throughR of formulae (2) to (4) and (6) to (8) 3 ～R 6 In the case of fluorine atoms, the effect of increasing mobility due to the decrease in anion size is more preferable because the ionic conductivity in the solution and in the composition becomes extremely high. It is considered that the higher the number of P-F bonds in the above general formulae (2) to (9), the more improved the low-temperature characteristics. In addition, R is as described above 3 ～R 6 Preferably an organic group selected from the group consisting of alkenyloxy and alkynyloxy. Unlike the alkenyloxy group and alkynyloxy group described above, when the hydrocarbon group is a hydrocarbon group containing no oxygen atoms, the electron withdrawing property is small, the ion dissociation degree is lowered, and the ion conductivity in the solution and in the composition is lowered, which is not preferable. In addition, in the case where the alkenyloxy group and the alkynyloxy group are groups having an unsaturated bond, decomposition occurs positively on the positive electrode and the negative electrode, and a coating film having more excellent durability can be formed, which is preferable. In addition, when the number of carbons is large, the anion size tends to be large, and the ionic conductivity in the solution and in the composition tends to be low, so that R is as described above 3 ～R 6 The carbon number of (2) is preferably 6 or less. When the carbon number is 6 or less, the ionic conductivity tends to be high, and particularly, when the ionic conductivity is a group selected from the group consisting of 1-propenyloxy, 2-propenyloxy, 3-butenyloxy, 2-propynyloxy and 1, 1-dimethyl-2-propynyloxy, the ionic size is preferably small.
In the above general formulae (4), (5), (8) and (9), X is as 1 And X 2 The alkyl group as shown in the figure, examples thereof include alkyl groups having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, trifluoromethyl, 2-difluoroethyl, 2-trifluoroethyl, 2, 3-tetrafluoropropyl and 1, 3-hexafluoroisopropyl, as the alkenyl group, there is used, examples of the "alkenyl group" and "fluoroalkenyl group" having 2 to 10 carbon atoms include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-butenyl group, 3-butenyl group and 1, 3-butadienyl group, examples of the "alkynyl group" and "fluoroalkynyl group" having 2 to 10 carbon atoms include ethynyl group, 2-propynyl group and 1, 1-dimethyl-2-propynyl group, and examples of the "cycloalkyl group" include cycloalkyl group "having 3 to 10 carbon atoms such as cyclopentyl group and cyclohexyl group, and examples of the" fluorocycloalkyl group "and" fluorocycloalkyl group "are given as examples of the" alkynyl group "and" fluorocycloalkyl group "and" cycloalkyl group "may include Examples of the cycloalkenyl group include cycloalkenyl groups having 3 to 10 carbon atoms such as cyclopentenyl and cyclohexenyl, and fluorinated cycloalkenyl groups, and examples of the aryl group include aryl groups having 6 to 10 carbon atoms such as phenyl, tolyl and xylyl. In addition, as the alkoxy group, examples thereof include alkoxy groups having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, pentyloxy, trifluoromethoxy, 2-difluoroethoxy, 2-trifluoroethoxy, 2, 3-tetrafluoropropoxy and 1, 3-hexafluoroisopropoxy, and fluoroalkoxy groups, examples of the alkenyloxy group include alkenyloxy groups having 2 to 10 carbon atoms such as ethyleneoxy group, 1-propyleneoxy group, 2-propyleneoxy group, isopropyleneoxy group, 2-butyleneoxy group, 3-butyleneoxy group and 1, 3-butyleneoxy group, fluorine-containing alkenyloxy group, examples of the alkynyloxy group include alkynyloxy groups and fluorinated alkynyloxy groups having 2 to 10 carbon atoms such as an ethynyloxy group, a 2-propynyloxy group and a 1, 1-dimethyl-2-propynyloxy group, examples of the cycloalkoxy group include cycloalkoxy groups and fluorinated cycloalkoxy groups having 3 to 10 carbon atoms such as a cyclopentyloxy group and a cyclohexyloxy group, examples of the cycloalkenyloxy group include cycloalkenyloxy groups and fluorinated cycloalkenyloxy groups having 3 to 10 carbon atoms such as a cyclopentyloxy group and a cyclohexene oxy group, examples of the aryloxy group include aryloxy groups and fluorinated aryloxy groups having 6 to 10 carbon atoms such as a phenoxy group, a tolyloxy group and a dimethylphenoxy group.
X of the above general formulae (4), (5), (8) and (9) 1 And X 2 In the case of fluorine atoms, the effect of the increase in ion dissociation degree due to the strong electron withdrawing property and the effect of the increase in mobility due to the decrease in anion size are preferably utilized to extremely increase the ion conductivity in the solution and in the composition. In addition, the X 1 And X 2 Preferably an organic group selected from the group consisting of alkoxy, alkenyloxy and alkynyloxy. Unlike the above alkoxy groups, alkenyloxy groups and alkynyloxy groups, when they are hydrocarbon groups not containing oxygen atoms, they are not preferable because they have small electron withdrawing properties and reduced ion dissociation degree and reduced ion conductivity in solution and in the composition. In addition, when the number of carbons is large, the anion size becomes large, and there is a decrease in ionic conductivity in the solution or in the compositionThe carbon number of X is preferably 6 or less. When the carbon number is 6 or less, the ionic conductivity tends to be high, and particularly, when the ionic conductivity is a group selected from the group consisting of methoxy, ethoxy, propoxy, 1-propenoxy, 2-propenoxy, 3-butenyloxy, 2-propynyloxy and 1, 1-dimethyl-2-propynyloxy, the ionic size is preferably small.
R of the above general formulae (2), (6), (7) and (8) 3 ～R 5 And X 1 Since compounds having a structure in which an oxygen atom is contained in each of the hydrocarbon groups (alkoxy group, alkenyloxy group, alkynyloxy group, cycloalkoxy group, cycloalkenyloxy group, aryloxy group), that is, compounds having no P-F bond or S-F bond at all, have extremely low solubility in a nonaqueous electrolyte (for example, less than 0.001 mass%), it is difficult to achieve the object of the present invention by adding the compounds to the nonaqueous electrolyte.
The lower limit of the suitable addition amount of the compound 2 is 0.001 mass% or more, more preferably 0.01 mass% or more, still more preferably 0.1 mass% or more, and the upper limit is 10.0 mass% or less, more preferably 5.0 mass% or less, still more preferably 2.0 mass% or less, relative to the total amount of the electrolyte for a nonaqueous electrolyte battery. If the content is less than 0.001 mass%, the effect of improving the output characteristics of the nonaqueous electrolyte battery at low temperature may not be sufficiently obtained. On the other hand, if the amount exceeds 10.0 mass%, not only the effect of the electrolyte is not obtained, but also the electrolyte is wastefully used, and the viscosity of the electrolyte tends to increase, so that the ionic conductivity tends to decrease, and the resistance increases, which tends to deteriorate the battery performance, which is not preferable. 1 kind of compound 2 may be added, or a plurality of kinds may be added.
More specifically, examples of anions of phosphates represented by the above general formula (2) include the following compound No. 14. However, the phosphate used in the present invention is not limited by any of the following examples.
Compound No.14
Examples of anions of imide salts represented by the general formulae (3) to (9) include, more specifically, the following compounds No.15 to No. 50. However, the imide salt used in the present invention is not limited by any of the following examples.
Compound No.19
Compound No.20
Compound No.21
Compound No.22
Compound No.23
Compound No.24
The salt of the anion of the phosphate represented by the above general formula (2) can be produced by, for example, the methods described in patent document 11, non-patent document 2 and non-patent document 3, as follows: by reacting halides, other than fluorides, liPF 6 A method of reacting with water in a nonaqueous solvent; a method of reacting a pyrophosphate having a corresponding alkoxy group with hydrogen fluoride.
The salt of the imide anion represented by the above general formula (3) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: by reacting the corresponding phosphorus oxychloride (P (=o) R 3 R 4 Cl) and phosphoric acid amide (H) 2 NP(＝O)R 5 R 6 ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (4) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: by reacting the corresponding phosphorus oxychloride (P (=o) R 3 R 4 Cl) and sulfonamide (H) 2 NSO 2 X 1 ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (5) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: the corresponding sulfonyl chloride (X) 1 SO 2 Cl) and the corresponding sulfonamide (H 2 NSO 2 X 2 ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (6) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: by reacting the corresponding phosphorus oxychloride (P (=o) R 3 R 4 Cl) and the corresponding phosphoric acid amide (H 2 NP(＝O)R 5 O - ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (7) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: by reacting the corresponding phosphorus oxychloride (P (=o) R 3 R 4 Cl) and sulfamic acid (H) 2 NSO 3 - ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (8) can be produced by various methods. The production method is not limited, and may be, for example, the following: the corresponding sulfonyl chloride (X) 1 SO 2 Cl) and the corresponding phosphoric acid amide (H 2 NP(＝O)R 3 O - ) In the presence of an organic or inorganic base.
The salt of the imide anion represented by the above general formula (9) can be produced by various methods. The production method is not limited, and may be obtained, for example, as follows: the corresponding sulfonyl chloride (X) 1 SO 2 Cl) and the corresponding sulfamic acid (H 2 NSO 3 - ) In the presence of an organic or inorganic base.
In the above-described production methods of the salts of the general formulae (2) to (9), cation exchange can be suitably performed.
(with respect to nonaqueous solvents)
The type of nonaqueous solvent used in the electrolyte for a nonaqueous electrolyte battery of the present invention is not particularly limited, and any nonaqueous solvent may be used. As specific examples, there may be mentioned: cyclic carbonates such as propylene carbonate, ethylene carbonate, butylene carbonate, and fluoroethylene carbonate, chain carbonates such as diethyl carbonate, dimethyl carbonate, and methylethyl carbonate, cyclic esters such as γ -butyrolactone and γ -valerolactone, chain esters such as methyl acetate, and methyl propionate, cyclic ethers such as tetrahydrofuran, 2-methyltetrahydrofuran, and dioxane, chain ethers such as dimethoxyethane, and diethyl ether, sulfone compounds such as dimethyl sulfoxide, and sulfolane, and sulfoxide compounds. In addition, ionic liquids of different types from nonaqueous solvents, and the like can be cited. The nonaqueous solvent used in the present invention may be used alone or in any combination and ratio depending on the application. Among these, propylene carbonate, ethylene carbonate, fluoroethylene carbonate, diethyl carbonate, dimethyl carbonate, and ethylmethyl carbonate are particularly preferable from the viewpoints of their electrochemical stability to oxidation and reduction and chemical stability involving heat and reaction with solutes.
(regarding solutes)
The type of solute used in the electrolyte for a nonaqueous electrolyte battery of the present invention is not particularly limited, and any electrolyte salt may be used. Specific examples of the lithium battery and lithium ion battery include LiPF 6 、LiBF 4 、LiClO 4 、LiAsF 6 、LiSbF 6 、LiCF 3 SO 3 、LiN(CF 3 SO 2 ) 2 、LiN(FSO 2 ) 2 、LiN(C 2 F 5 SO 2 ) 2 、LiN(CF 3 SO 2 )(C 4 F 9 SO 2 )、LiC(CF 3 SO 2 ) 3 、LiPF 3 (C 3 F 7 ) 3 、LiB(CF 3 ) 4 、LiBF 3 (C 2 F 5 )、LiN(POF 2 ) 2 In the case of sodium ion batteries, etc., electrolyte salts typified by NaPF are given 6 、NaBF 4 、NaCF 3 SO 3 、NaN(CF 3 SO 2 ) 2 、NaN(FSO 2 ) 2 、NaN(POF 2 ) 2 And the like are typical electrolyte salts. These solutes may be used alone or in any combination and ratio depending on the application. Among them, liPF is preferable in terms of energy density, output characteristics, life and the like when the battery is manufactured 6 、LiBF 4 、LiN(CF 3 SO 2 ) 2 、LiN(FSO 2 ) 2 、LiN(C 2 F 5 SO 2 ) 2 、LiN(POF 2 ) 2 、NaPF 6 、NaBF 4 、NaN(CF 3 SO 2 ) 2 、NaN(FSO 2 ) 2 、NaN(POF 2 )2。
The concentration of these solutes is not particularly limited, and a suitable concentration range is a range in which the lower limit is 0.5mol/L or more, more preferably 0.7mol/L or more, still more preferably 0.9mol/L or more, and the upper limit is 2.5mol/L or less, more preferably 2.0mol/L or less, still more preferably 1.5mol/L or less. When the ionic conductivity is lower than 0.5mol/L, the cycle characteristics and output characteristics of the nonaqueous electrolyte battery may be lowered. On the other hand, if the concentration exceeds 2.5mol/L, the ionic conductivity may be lowered due to an increase in the viscosity of the electrolyte for a nonaqueous electrolyte battery, and the cycle characteristics and output characteristics of the nonaqueous electrolyte battery may be lowered.
If a large amount of the solute is dissolved in a nonaqueous solvent at a time, the solution temperature may be increased by the heat of dissolution of the solute. If the liquid temperature is significantly increased, the decomposition of the electrolyte salt containing fluorine may be promoted to generate hydrogen fluoride. Hydrogen fluoride is a cause of deterioration in battery performance and is therefore not preferable. Therefore, the liquid temperature at the time of dissolving the solute in the nonaqueous solvent is not particularly limited, but is preferably-20 to 80 ℃, more preferably 0 to 60 ℃.
The above description has been made with respect to at least the components to be contained as the basic constituent components of the electrolyte for a nonaqueous electrolyte battery of the present invention, but additives generally used may be added to the electrolyte for a nonaqueous electrolyte battery of the present invention in any ratio as long as the gist of the present invention is not impaired. As specific examples, there may be mentioned: and compounds having an overcharge preventing effect, a negative electrode coating film forming effect, and a positive electrode protecting effect, such as cyclohexylbenzene, biphenyl, t-butylbenzene, vinylene carbonate, vinyl ethylene carbonate, difluoroanisole, fluoroethylene carbonate, propane sultone, succinonitrile, and dimethylvinylene carbonate. In addition, as used in a nonaqueous electrolyte battery called a lithium polymer battery, the nonaqueous electrolyte battery electrolyte may be quasi-solid-state and then used by using a gelling agent or a crosslinked polymer.
Next, the constitution of the nonaqueous electrolyte battery of the present invention will be described. The nonaqueous electrolyte battery of the present invention is characterized in that the above-described electrolyte solution for a nonaqueous electrolyte battery of the present invention is used, and other constituent members are used as usual members for nonaqueous electrolyte batteries. That is, a positive electrode and a negative electrode which can absorb and release cations, a current collector, a separator, a container, and the like are included.
The negative electrode material is not particularly limited, and in the case of a lithium battery and a lithium ion battery, lithium metal, an alloy of lithium metal and other metals, intermetallic compounds, various carbon materials (artificial graphite, natural graphite, and the like), metal oxides, metal nitrides, tin (simple substance), tin compounds, silicon (simple substance), silicon compounds, activated carbon, conductive polymers, and the like can be used.
The carbon material is, for example, easily graphitizable carbon, hard carbon having a (002) plane spacing of 0.37nm or more, graphite having a (002) plane spacing of 0.34nm or less, or the like. More specifically, it includes pyrolytic carbon, cokes, glassy carbon fibers, organic polymer compound fired bodies, activated carbon, carbon black, and the like. Among them, the coke includes pitch coke, needle coke, petroleum coke, and the like. The organic polymer compound fired body is a product obtained by firing a phenol resin, a furan resin, or the like at an appropriate temperature to char. The carbon material is preferable because it has very little crystal structure change associated with the absorption and release of lithium, and therefore can obtain a high energy density and excellent cycle characteristics. The shape of the carbon material may be any of fibrous, spherical, granular, or scaly. Further, amorphous carbon and a graphite material coated with amorphous carbon on the surface are more preferable because the reactivity of the material surface with an electrolyte is reduced.
The positive electrode material is not particularly limited, and in the case of a lithium battery and a lithium ion battery, for example, liCoO is used 2 、LiNiO 2 、LiMnO 2 、LiMn 2 O 4 And lithium-containing transition metal composite oxides; a material obtained by mixing a plurality of transition metals such as Co, mn, ni and the like of the lithium-containing transition metal composite oxide; these lithium-containing transition metalsA part of the transition metal of the composite oxide is replaced with a material of a metal other than the transition metal; liFePO called olivine 4 、LiCoPO 4 、LiMnPO 4 Phosphate compounds of the transition metals; tiO (titanium dioxide) 2 、V 2 O 5 、MoO 3 An iso-oxide; tiS (TiS) 2 Sulfides such as FeS; or conductive polymers such as polyacetylene, polyparaphenylene, polyaniline and polypyrrole; activated carbon; a free radical generating polymer; carbon materials, and the like.
Acetylene black, ketjen black, carbon fiber, graphite, polytetrafluoroethylene, polyvinylidene fluoride, SBR resin, etc. as a binder material are added to the positive electrode material and the negative electrode material as conductive materials, and are molded into a sheet shape, whereby an electrode sheet can be produced.
As a separator for preventing contact between the positive electrode and the negative electrode, nonwoven fabric or porous sheet made of polypropylene, polyethylene, paper, glass fiber or the like is used.
The above elements are assembled into a coin-shaped, cylindrical, square, aluminum laminate-shaped nonaqueous electrolyte battery.
Examples
The present invention will be specifically described below by way of examples, but the present invention is not limited to the examples.
[ preparation of nonaqueous electrolyte ]
As nonaqueous solvents, ethylene carbonate, propylene carbonate, dimethyl carbonate, ethyl methyl carbonate were used in a volume ratio of 2:1:4:3 by mixing a solvent in which LiPF as a solute is caused to act 6 Dissolving to make the concentration of the solution be 1.0 mol/L. Thereafter, the compound No.2 as the 1 st compound was added to a concentration of 0.5 mass%, and the lithium salt of the compound No.15 as the 2 nd compound was added to a concentration of 1.0 mass%, followed by stirring to prepare an electrolyte No.1. The above preparation was performed while maintaining the liquid temperature at 25 ℃. The preparation conditions of the electrolyte No.1 are shown in Table 1.
The electrolyte solutions nos. 2 to 129 were prepared by the same procedure as described above except that the type and concentration of the 1 st compound, the type and concentration of the 2 nd compound, and the counter cation were changed as shown in tables 1 and 2. Anions of the compounds nos. 51 to 53 used as the 1 st compound in the preparation of the electrolytic solutions nos. 117 to 119 and the compounds nos. 54 to 63 used as the 2 nd compound in the preparation of the electrolytic solutions nos. 120 to 129 are shown below.
Examples 1 to 1
As the nonaqueous electrolytic solution, liNi was used as the electrolyte solution No.1 1/3 Mn 1/3 Co 1/3 O 2 As a positive electrode material and graphite as a negative electrode material, a battery was fabricated, and the high-temperature cycle characteristics, high-temperature storage characteristics, and low-temperature output characteristics of the battery were actually evaluated. The test cell was prepared as follows.
In LiNi 1/3 Mn 1/3 Co 1/3 O 2 To 90 mass% of the powder, 5 mass% of polyvinylidene fluoride (PVDF) as a binder and 5 mass% of acetylene black as a conductive material were mixed, and N-methylpyrrolidone was further added to prepare a paste. The paste was coated on an aluminum foil and dried to prepare a positive electrode body for test. Further, PVDF (10 mass%) as a binder was mixed with 90 mass% of graphite powder, and N-methylpyrrolidone was further added thereto to prepare a slurry. The slurry was coated on a copper foil and dried at 150 ℃ for 12 hours to prepare a test anode body. Then, the electrolyte was immersed in a polyethylene separator, and a 100mAh cell with an aluminum laminate case was assembled.
The battery manufactured by the above method was used to conduct a charge/discharge test, and the high-temperature cycle characteristics, the high-temperature storage characteristics, and the low-temperature output characteristics were evaluated by the methods described below. The evaluation results are shown in table 3.
[ test of high-temperature cycle characteristics ]
A charge-discharge test at an ambient temperature of 55 ℃ was performed to evaluate cycle characteristics. Charging was carried out to 4.3V, discharging was carried out to 3.0V, and the current density was 1.9mA/cm 2 The charge-discharge cycle is repeated. Then, the deterioration condition of the battery was evaluated at a discharge capacity maintenance rate after 200 cycles (cycle characteristic evaluation). The discharge capacity maintenance rate was determined by the following equation.
Discharge capacity maintenance rate after 200 cycles >
The discharge capacity maintenance rate (%) = (discharge capacity after 200 cycles/initial discharge capacity) ×100 it is to be noted that the values of the discharge capacity maintenance rates after 200 cycles shown in table 3 are relative values when the discharge capacity maintenance rate after 200 cycles is 100 in comparative example 1-1.
[ test for high-temperature storage Property ]
After the above-mentioned cyclic test, the constant current and constant voltage method was used at an ambient temperature of 25℃and a current density of 0.38mA/cm 2 Charging was performed until the upper charging voltage was 4.3V, and then stored at an ambient temperature of 50 ℃ for 10 days. Thereafter, the current density was 0.38mA/cm 2 The storage characteristics of the cells were evaluated by setting the ratio of the discharge capacity to the initial discharge capacity (the discharge capacity measured before storage at 50 ℃ C. After the above-mentioned cycle test) as the residual capacity ratio, and discharging the cells to a discharge termination voltage of 3.0V. The values of the residual capacity ratios shown in table 3 are relative values obtained when the residual capacity ratio of comparative example 1-1 is 100.
[ test of Low temperature output characteristics ]
After the storage test, the sample was subjected to a constant current and constant voltage method at an ambient temperature of 25℃and a current density of 0.38mA/cm 2 Charging until the upper limit voltage is 4.3V, and then applying constant current method at-30deg.C with current density of 9.5mA/cm 2 The discharge was performed up to a discharge lower limit voltage of 3.0V, and the average discharge voltage at this time was measured. The average discharge voltage values shown in table 2 are relative values when the average discharge voltage of comparative example 1-1 is 100.
Examples 1-2 to 1-65 and comparative examples 1-1 to 1-64
Batteries similar to those in example 1-1 were produced by using the electrolytes nos. 2 to 129 in place of the electrolyte No.1, and the high-temperature cycle characteristics, the high-temperature storage characteristics and the low-temperature output characteristics were evaluated in the same manner. The evaluation results are shown in tables 3 and 4.
TABLE 1
TABLE 2
TABLE 3
* Relative value when the value of comparative example 1-1 was set to 100
TABLE 4
* Relative value when the value of comparative example 1-1 was set to 100
If the above results are compared, it can be confirmed that: by using the 1 st compound and the 2 nd compound in combination, the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are improved as compared with comparative examples 1-2 to 1-14 in which the 1 st compound is used alone. Also, as such, it can be confirmed that: the high temperature cycle characteristics, high temperature storage characteristics and low temperature output characteristics were improved as compared with comparative examples 1-15 to 1-51 in which compound 2 was used alone.
On the other hand, R of the 1 st compound represented by the general formula (1) was as in comparative examples 1 to 52 and 1 to 53 2 In the case of not a straight-chain or branched alkyl group having 1 to 10 carbon atoms (a fluoro group is present in comparative examples 1 to 52, and a methoxy group is present in comparative examples 1 to 53), the low-temperature output characteristics are lowered, and the improvement of the high-temperature cycle characteristics and the high-temperature storage characteristics cannot be confirmed. In addition, as in comparative examples 1 to 54, the number of groups having carbon-carbon unsaturated bonds was 1 or moreIn the following cases, improvement of the high-temperature cycle characteristics, the high-temperature storage characteristics, and the low-temperature output characteristics could not be confirmed.
In addition, in the case where the compound 2 does not contain a P-F bond or an S-F bond as in comparative examples 1-55 to 1-58, improvement in high temperature cycle characteristics, high temperature storage characteristics and low temperature output characteristics could not be confirmed. Further, as in comparative examples 1-59 to 1-64, the compound 2 contained P-F bond and S-F bond, but the substituent bonded to the P atom was not a structure containing a hydrocarbon group (for example, an alkoxy group or the like) with an oxygen atom interposed therebetween, but a structure containing a hydrocarbon group (for example, an alkyl group or the like) without an oxygen atom interposed therebetween, and the low-temperature output characteristics were lowered, and the improvement of the high-temperature cycle characteristics and the high-temperature storage characteristics could not be confirmed.
The following describes the results of evaluation of the 1 st and 2 nd compounds by using the typical combinations and concentrations of electrolytes, changing the types of positive electrodes, negative electrodes, and counter cations of the 2 nd compounds. It was confirmed that the same tendency as described above was exhibited by the electrolyte solution except for the combination and concentration of the 1 st compound and the 2 nd compound described below.
Examples 2-1 to 2-43 and comparative examples 2-1 to 2-20
Batteries were produced and evaluated in the same manner as in example 1-1 except that the electrolytes for nonaqueous electrolyte batteries were changed as shown in table 6 in examples 2-1 to 2-43 and comparative examples 2-1 to 2-20. The negative electrode active material was Li 4 Ti 5 O 12 In examples 2-1 to 2-13 and comparative examples 2-1 to 2-5, the negative electrode body was produced as follows: in Li 4 Ti 5 O 12 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive agent were mixed, and N-methylpyrrolidone was further added thereto, and the obtained paste was coated on a copper foil and dried to prepare a battery having a charge termination voltage of 2.8V and a discharge termination voltage of 1.5V at the time of battery evaluation. In examples 2-14 to 2-30 and comparative examples 2-6 to 2-15 in which the negative electrode active material was graphite (containing silicon), the negative electrode body was produced as follows: 81 mass% of graphite powder 9 mass% of silicon powder was mixed with 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material, and N-methylpyrrolidone was further added thereto, and the obtained paste was coated on a copper foil and dried to prepare a battery having the same charge termination voltage and discharge termination voltage as in example 1-1. In examples 2-31 to 2-43 and comparative examples 2-16 to 2-20 in which the negative electrode active material was hard carbon, the negative electrode body was produced as follows: to 90 mass% of hard carbon powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive agent were mixed, and N-methylpyrrolidone was further added, and the obtained paste was coated on a copper foil and dried to prepare a battery, wherein the charge termination voltage at the time of battery evaluation was set to 4.2V and the discharge termination voltage was set to 2.2V.
In addition, the electrolytes used in examples 2 to 27 were prepared as follows. As nonaqueous solvents, ethylene carbonate, fluoroethylene carbonate, dimethyl carbonate, and methylethyl carbonate were used in a volume ratio of 2.5:0.5:4:3, in which LiPF as a solute is dissolved 6 The concentration was set to 1.0 mol/L. Thereafter, the compound No.2 as the 1 st compound was added to a concentration of 0.5 mass%, and the lithium salt of the compound No.15 as the 2 nd compound was added to a concentration of 1.0 mass%, followed by stirring to prepare an electrolyte solution No.130. The above preparation was performed while maintaining the liquid temperature at 25 ℃. The preparation conditions of electrolyte No.130 are shown in Table 5. In addition, electrolyte nos. 131 to 138 were prepared in the same manner as described above, except that the types of the 1 st compound and the 2 nd compound were changed as shown in table 5.
The evaluation results of the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are shown in table 6. In table 6, the evaluation results (the discharge capacity maintenance rate after 200 cycles, the residual capacity ratio, and the average discharge voltage) of examples 2-1 to 2-26, examples 2-31 to 2-43, comparative examples 2-1 to 2-10, and comparative examples 2-16 to 2-20 were relative values when the evaluation result of the comparative example using the electrolyte of electrolyte No.66 was 100 in each electrode configuration. In table 6, the evaluation results (the discharge capacity maintenance rate after 200 cycles, the residual capacity ratio, and the average discharge voltage) of examples 2-27 to 2-30 and comparative examples 2-11 to 2-15 are relative values when the evaluation result of the comparative example using the electrolyte solution No.134 is 100.
TABLE 5
TABLE 6
* In each corresponding battery configuration, the relative value was set to 100 for the comparative example using electrolyte No.66
(in examples 2-27 to 2-30 and comparative examples 2-11 to 2-15, the relative value was set to 100 in comparative examples 2-11)
Examples 3-1 to 3-52 and comparative examples 3-1 to 3-20
Batteries were produced and evaluated in the same manner as in example 1-1 except that the electrolytes for nonaqueous electrolyte batteries were prepared in examples 3-1 to 3-52 and comparative examples 3-1 to 3-20 by changing the positive electrode body, the negative electrode body and the electrolytes as shown in tables 7 and 8. The positive electrode active material was LiCoO 2 The positive electrode body of (2) is manufactured as follows: in LiCoO 2 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material were mixed, N-methylpyrrolidone was further added, and the resulting paste was applied to an aluminum foil and dried to prepare the aluminum foil. In examples 3-1 to 3-13 in which the negative electrode active material was graphite and comparative examples 3-1 to 3-5, the charge termination voltage at the time of battery evaluation was set to 4.2V and the discharge termination voltage was set to 3.0V in the same manner as in example 1-1. As in example 2-1, the negative electrode active material was Li 4 Ti 5 O 12 In examples 3-14 to 3-26 and comparative examples 3-6 to 3-10, the charge termination voltage at the time of battery evaluation was set to 2.7V and the discharge termination voltage was set to 1.5V. And the actual onesIn the same manner as in examples 2 to 14, in examples 3 to 27 to 3 to 39 and comparative examples 3 to 11 to 3 to 15 in which the negative electrode active material was graphite (containing 9 mass% of silicon), the charge termination voltage at the time of battery evaluation was set to 4.2V and the discharge termination voltage was set to 3.0V. In examples 3-40 to 3-52 and comparative examples 3-16 to 3-20 in which the negative electrode active material was hard carbon, the charge termination voltage at the time of battery evaluation was set to 4.1V and the discharge termination voltage was set to 2.2V in the same manner as in examples 2 to 31. The evaluation results of the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are shown in tables 7 and 8. The evaluation results (the discharge capacity maintenance rate after 200 cycles, the residual capacity ratio, and the average discharge voltage) in tables 7 and 8 are relative values when the evaluation result of the comparative example using the electrolyte of electrolyte No.66 was 100 in each electrode configuration.
TABLE 7
* In each corresponding battery configuration, the relative value was set to 100 for the comparative example of the convenient electrolyte No.66
TABLE 8
* In each corresponding battery configuration, the relative value was set to 100 for the comparative example of the convenient electrolyte No.66
Examples 4-1 to 4-39 and comparative examples 4-1 to 4-15
Batteries were produced and evaluated in the same manner as in example 1-1 except that the electrolytes for nonaqueous electrolyte batteries were changed as shown in table 9 in examples 4-1 to 4-39 and comparative examples 4-1 to 4-15. The positive electrode active material was LiNi 0.8 Co 0.15 Al 0.05 O 2 In examples 4-1 to 4-13 and comparative examples 4-1 to 4-5, positive electrode bodies were produced as follows: in LiNi 0.8 Co 0.15 Al 0.05 O 2 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material were mixed, and N-methylpyrrolidone was further added thereto, and the resulting paste was applied to an aluminum foil and dried to prepare a battery having a charge termination voltage of 4.3V and a discharge termination voltage of 3.0V at the time of battery evaluation. In addition, the positive electrode active material is LiMn 2 O 4 In examples 4-14 to 4-26 and comparative examples 4-6 to 4-10, positive electrode bodies were produced as follows: in LiMn 2 O 4 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material were mixed, and N-methylpyrrolidone was further added thereto, and the resulting paste was applied to an aluminum foil and dried to prepare a battery having a charge termination voltage of 4.2V and a discharge termination voltage of 3.0V at the time of battery evaluation. In addition, the positive electrode active material is LiFePO 4 In examples 4-27 to 4-39 and comparative examples 4-11 to 4-15, positive electrode bodies were produced as follows: in LiFePO coated with amorphous carbon 4 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material were mixed, and N-methylpyrrolidone was further added thereto, and the resulting paste was applied to an aluminum foil and dried to prepare a battery having a charge termination voltage of 4.2V and a discharge termination voltage of 2.5V at the time of battery evaluation. The evaluation results of the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are shown in table 9. The evaluation results (the discharge capacity maintenance rate after 200 cycles, the residual capacity ratio, and the average discharge voltage) in table 9 were relative values when the evaluation result of the comparative example using the electrolyte of electrolyte No.66 was 100 in each electrode configuration.
TABLE 9
* In each corresponding battery configuration, the relative value was set to 100 for the comparative example of the convenient electrolyte No.66
As described above, li is used 4 Ti 5 O 12 Graphite (containing silicon) and hardIn any of the examples in which carbon was used as the negative electrode active material, it was confirmed that the use of the electrolyte for a nonaqueous electrolyte battery of the present invention improved the high-temperature cycle characteristics, the high-temperature storage characteristics and the low-temperature output characteristics as compared with the respective corresponding comparative examples. Therefore, it was revealed that by using the electrolyte for a nonaqueous electrolyte battery of the present invention, a nonaqueous electrolyte battery exhibiting excellent high-temperature cycle characteristics, high-temperature storage characteristics and low-temperature output characteristics can be obtained regardless of the kind of the negative electrode active material.
In addition, liCoO is used as described above 2 、LiNi 0.8 Co 0.15 Al 0.05 O 2 、LiMn 2 O 4 And LiFePO 4 In any of the examples as the positive electrode active material, it was confirmed that the use of the electrolyte for a nonaqueous electrolyte battery of the present invention improved the high-temperature cycle characteristics, the high-temperature storage characteristics and the low-temperature output characteristics as compared with the respective corresponding comparative examples. Therefore, it was revealed that by using the electrolyte for a nonaqueous electrolyte battery of the present invention, a nonaqueous electrolyte battery exhibiting excellent high-temperature cycle characteristics, high-temperature storage characteristics and low-temperature output characteristics can be obtained regardless of the kind of the positive electrode active material.
Examples 5 to 1
As the nonaqueous solvent, a volume ratio of ethylene carbonate to diethyl carbonate of 1:1, in which NaPF as a solute is dissolved 6 The concentration was set to 1.0 mol/L. Thereafter, the compound No.2 as the 1 st compound was added to a concentration of 0.5 mass%, and the sodium salt of the compound No.15 as the 2 nd compound was added to a concentration of 1.0 mass%, followed by stirring to prepare an electrolyte No.139. The preparation conditions of the electrolyte are shown in table 10.
Using the electrolyte, naFe was prepared 0.5 Co 0.5 O 2 A battery was produced in the same manner as in example 1-1 except that the positive electrode material and the hard carbon were used as the negative electrode material, and the high-temperature cycle characteristics, the high-temperature storage characteristics, and the low-temperature output characteristics were evaluated in the same manner as in example 1-1. The positive electrode active material was NaFe 0.5 Co 0.5 O 2 The positive electrode body of (2) is manufactured as follows: in NaFe 0.5 Co 0.5 O 2 To 90 mass% of the powder, 5 mass% of PVDF as a binder and 5 mass% of acetylene black as a conductive material were mixed, and N-methylpyrrolidone was further added thereto, and the resulting paste was applied to an aluminum foil and dried to prepare a battery having a charge termination voltage of 3.8V and a discharge termination voltage of 1.5V at the time of battery evaluation. The evaluation results are shown in table 11.
Examples 5-2 to 5-13 and comparative examples 5-1 to 5-6
In examples 5-2 to 5-13 and comparative examples 5-1 to 5-6, batteries were produced and evaluated in the same manner as in example 5-1 except that the types of the 1 st compound and the 2 nd compound were changed as shown in table 10. The evaluation results of the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are shown in table 11. The evaluation results (the value of the discharge capacity maintenance rate, the value of the residual capacity ratio, and the value of the average discharge voltage after 200 cycles) in table 11 are relative values when the evaluation result of comparative example 5-1 is 100.
TABLE 10
TABLE 11
* Relative value when the result of comparative example 5-l was set to 100
If the above results are compared, it can be confirmed that: in the sodium ion battery, by using the 1 st compound and the 2 nd compound in combination, the high temperature cycle characteristics, the high temperature storage characteristics and the low temperature output characteristics are improved as compared with comparative example 5-2 in which the 1 st compound is used alone. Also, as such, it can be confirmed that: the high temperature cycle characteristics, high temperature storage characteristics and low temperature output characteristics were improved as compared with comparative examples 5-3 in which compound 2 was used alone. In addition, e.g. R of the 1 st Compound represented by the general formula (1) as in comparative examples 5 to 4 2 In the case of not a linear or branched alkyl group having 1 to 10 carbon atoms (having a fluoro group in comparative examples 5 to 4), the low-temperature output characteristics were lowered, and the improvement of the high-temperature cycle characteristics and the high-temperature storage characteristics could not be confirmed.
In addition, as in comparative examples 5 to 5, in the case where the compound 2 does not contain a P-F bond or an S-F bond, improvement in high temperature cycle characteristics, high temperature storage characteristics and low temperature output characteristics could not be confirmed.
In addition, as in comparative examples 5 to 6, the compound 2 contained a p—f bond, but when the substituent bonded to the P atom was not a hydrocarbon group containing an oxygen atom (for example, an alkoxy group or the like) but a hydrocarbon group containing no oxygen atom (for example, an alkyl group or the like), the low-temperature output characteristic was lowered, and improvement in the high-temperature cycle characteristic and the high-temperature storage characteristic could not be confirmed.
Claims (25)
1. An electrolyte for a nonaqueous electrolyte battery, comprising at least: a nonaqueous solvent, a solute, at least 1 silane compound represented by the following general formula (1) as a 1 st compound, and at least 1 compound selected from the group consisting of fluorine-containing compounds represented by the following general formulas (2) to (9) as a 2 nd compound,
The concentration of the solute is in the range of 0.5mol/L to 2.5mol/L,
Si(R 1 ) a (R 2 ) 4-a (1)
in the general formula (1), R 1 Each independently of the other represents a group having a carbon-carbon unsaturated bond, R 2 Independently of each other, represent a straight-chain or branched alkyl group having 1 to 10 carbon atomsThese groups optionally have a fluorine atom and/or an oxygen atom, and in the case where these groups have an oxygen atom, they refer to a structure other than an alkoxy group, that is, a structure in which an atom bonded to a silicon atom of the formula (1) is not an oxygen atom, a is 2 to 4, and R in the formulae (2) to (4) and (6) to (8) 3 ～R 6 Each independently of the other is a fluorine atom or an organic group selected from the group consisting of a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, in which the presence or absence of a fluorine atom, an oxygen atom or an unsaturated bond in the organic group is represented by the general formulae (4), (5), (8) and (9), X 1 And X 2 Each independently of the other is a fluorine atom, or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, wherein the organic group contains at least one P-F bond and/or at least one S-F bond, M in the formulae (2) to (9) in the presence or absence of a fluorine atom, an oxygen atom or an unsaturated bond 1 、M 2 Each, independently of the others, is a proton, a metal cation or an onium cation.
2. The electrolyte for a nonaqueous electrolyte battery according to claim 1, wherein the 1 st compound is selected from the group consisting of compound No.2 and compound No.7,
3. the electrolyte for a nonaqueous electrolyte battery according to claim 1, wherein the anion of the 2 nd compound is selected from the group consisting of compounds,
compound No.19
Compound No.20
Compound No.21
Compound No.22
Compound No.23
4. The electrolyte for a nonaqueous electrolyte battery according to claim 1 or 2, wherein the nonaqueous solvent is at least one nonaqueous solvent selected from the group consisting of a cyclic ester, a chain ester, a cyclic ether, a chain ether, a sulfone compound, a sulfoxide compound, and an ionic liquid.
5. The electrolyte for a nonaqueous electrolyte battery according to claim 4, wherein the cyclic ester comprises a cyclic carbonate, and/or the chain ester comprises a chain carbonate.
6. The electrolyte for a nonaqueous electrolyte battery according to claim 1 or 2, further comprising: cyclohexylbenzene, biphenyl, tert-butylbenzene, vinylene carbonate, vinyl ethylene carbonate, difluoroanisole, fluoroethylene carbonate, propane sultone, succinonitrile or dimethylvinylene carbonate.
7. The electrolyte for a nonaqueous electrolyte battery according to claim 1 or 2, wherein M in the general formulae (2) to (9) 1 And M 2 Each independently of the other is at least one cation selected from the group consisting of lithium ion, sodium ion, potassium ion, tetraalkylammonium ion and tetraalkylphosphonium ion.
8. The electrolyte for a nonaqueous electrolyte battery according to claim 1 or 2, wherein the solute is at least one solute selected from the group consisting of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (trifluoromethanesulfonyl) imide, lithium bis (fluorosulfonyl) imide, lithium bis (difluorophosphoryl) imide, sodium hexafluorophosphate, sodium tetrafluoroborate, sodium bis (trifluoromethanesulfonyl) imide, sodium bis (fluorosulfonyl) imide, and sodium bis (difluorophosphoryl) imide.
9. The electrolyte for a nonaqueous electrolyte battery according to claim 4, wherein the nonaqueous solvent is at least one compound selected from the group consisting of propylene carbonate, ethylene carbonate, fluoroethylene carbonate, diethyl carbonate, dimethyl carbonate and ethylmethyl carbonate.
10. A nonaqueous electrolyte battery, characterized by comprising at least: a positive electrode, a negative electrode, a separator, and the electrolyte for a nonaqueous electrolyte battery according to claim 1 or 2.
11. The nonaqueous electrolyte battery according to claim 10, wherein the negative electrode material of the negative electrode is at least one compound selected from the group consisting of lithium metal, an alloy of lithium metal and other metal, an intermetallic compound of lithium metal and other metal, a carbon material, a metal oxide, a metal nitride, a tin simple substance, a tin compound, a silicon simple substance, a silicon compound, and a conductive polymer.
12. The nonaqueous electrolyte battery according to claim 11, wherein the carbon material is artificial graphite or natural graphite.
13. The nonaqueous electrolyte battery according to claim 11, wherein the carbon material is graphitizable carbon, hard carbon which is hard carbon having a (002) plane spacing of 0.37nm or more, or graphite having a (002) plane spacing of 0.34nm or less.
14. The nonaqueous electrolyte battery according to claim 11, wherein the carbon material is pyrolytic carbon, coke, glassy carbon fiber, an organic polymer compound fired body, activated carbon, or carbon black.
15. The nonaqueous electrolyte battery according to claim 11, wherein the carbon material is amorphous carbon or a graphite material coated with amorphous carbon on a surface thereof.
16. The nonaqueous electrolyte battery according to claim 10, wherein the positive electrode material of the positive electrode is selected from the group consisting of lithium-containing transition metal composite oxides, transition metal phosphate compounds, and TiO 2 、V 2 O 5 、MoO 3 、TiS 2 At least one compound selected from the group consisting of FeS, conductive polymers, radical generating polymers, and carbon materials.
17. The nonaqueous electrolyte battery according to claim 16, wherein the lithium-containing transition metal composite oxide is a composite oxide in which a transition metal in the lithium-containing transition metal composite oxide is mixed with a plurality of transition metals or a material in which a part of a transition metal in the lithium-containing transition metal composite oxide is replaced with another metal other than the transition metal.
18. The nonaqueous electrolyte battery according to claim 16 or 17, wherein the lithium-containing transition metal composite oxide is a composite oxide in which transition metals in the lithium-containing transition metal composite oxide are mixed of Co, mn, and Ni.
19. The nonaqueous electrolyte battery according to claim 16 or 17, wherein the lithium-containing transition metal composite oxide is selected from the group consisting of LiCoO 2 、LiNiO 2 、LiMnO 2 、LiMn 2 O 4 And LiNi 1/3 Mn 1/3 Co 1/3 O 2 At least one compound of the group consisting of.
20. The nonaqueous electrolyte battery according to claim 16, wherein the phosphoric acid compound of the transition metal is selected from the group consisting of LiFePO 4 、LiCoPO 4 、LiMnPO 4 At least one compound of the group consisting of.
21. The nonaqueous electrolyte battery according to claim 10, wherein the positive electrode material of the positive electrode is selected from the group consisting of LiNi 1/3 Mn 1/3 Co 1/3 O 2 、LiCoO 2 、LiNi 0.8 Co 0.15 Al 0.05 O 2 、LiMn 2 O 4 、LiFePO 4 And NaFe 0.5 Co 0.5 O 2 A group of groups.
22. The nonaqueous electrolyte battery according to claim 16, wherein the conductive polymer is at least one compound selected from the group consisting of polyacetylene, polyparaphenylene, polyaniline and polypyrrole.
23. The nonaqueous electrolyte battery according to claim 11, wherein the negative electrode material further comprises at least one conductive material selected from the group consisting of acetylene black, ketjen black, carbon fiber, and graphite and comprises at least one binder material selected from the group consisting of polytetrafluoroethylene, polyvinylidene fluoride, and SBR resin.
24. The nonaqueous electrolyte battery according to claim 16 or 17, wherein the positive electrode material further contains at least one conductive material selected from the group consisting of acetylene black, ketjen black, carbon fiber, and graphite and contains at least one binder material selected from the group consisting of polytetrafluoroethylene, polyvinylidene fluoride, and SBR resin.
25. The nonaqueous electrolyte battery according to claim 10, wherein the separator is a nonwoven fabric or a porous sheet made of polypropylene, polyethylene, paper or glass fiber.
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| CN201911249839.8A CN110880619B (en) | 2015-02-19 | 2016-02-18 | Electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using same |
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| JP2015-030411 | 2015-02-19 | ||
| JP2015254114A JP6665396B2 (en) | 2015-02-19 | 2015-12-25 | Electrolyte for non-aqueous electrolyte battery and non-aqueous electrolyte battery using the same |
| JP2015-254114 | 2015-12-25 | ||
| CN201911249839.8A CN110880619B (en) | 2015-02-19 | 2016-02-18 | Electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using same |
| PCT/JP2016/054748 WO2016133169A1 (en) | 2015-02-19 | 2016-02-18 | Electrolyte for nonaqueous-electrolyte cell, and non-aqueous electrolyte cell in which same is used |
| CN201680010967.5A CN107251310B (en) | 2015-02-19 | 2016-02-18 | Electrolyte for nonaqueous electrolyte battery and nonaqueous electrolyte battery using same |
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| US10851124B2 (en) | 2017-04-10 | 2020-12-01 | Central Glass Co., Ltd. | Method for producing phosphoryl imide salt, method for producing nonaqueous electrolyte solution containing said salt, and method for producing nonaqueous secondary battery |
| CN108808087B (en) * | 2018-05-04 | 2022-06-10 | 常德市大度新材料有限公司 | Electrolyte containing lithium phosphoryl imide and battery using electrolyte |
| CN111786020B (en) * | 2020-07-20 | 2022-11-29 | 香河昆仑新能源材料股份有限公司 | Non-aqueous electrolyte containing fluoro phosphoramidate and lithium ion battery |
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