WO2023043190A1 - 리튬 이차전지용 비수 전해액 및 이를 포함하는 리튬 이차전지 - Google Patents
리튬 이차전지용 비수 전해액 및 이를 포함하는 리튬 이차전지 Download PDFInfo
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- WO2023043190A1 WO2023043190A1 PCT/KR2022/013726 KR2022013726W WO2023043190A1 WO 2023043190 A1 WO2023043190 A1 WO 2023043190A1 KR 2022013726 W KR2022013726 W KR 2022013726W WO 2023043190 A1 WO2023043190 A1 WO 2023043190A1
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- Prior art keywords
- formula
- secondary battery
- lithium secondary
- aqueous electrolyte
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- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 95
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- 239000011255 nonaqueous electrolyte Substances 0.000 title claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 17
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 17
- -1 propargyl 1H-imidazole-1-carboxylate Chemical compound 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
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- 229910000077 silane Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000006234 thermal black Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- ZNBGTBKGFZMWKR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-5-(1,1,2,2-tetrafluoroethoxy)pentane Chemical compound FC(F)C(F)(F)OCC(F)(F)C(F)(F)C(F)(F)C(F)F ZNBGTBKGFZMWKR-UHFFFAOYSA-N 0.000 description 1
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 1
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- DRVMZMGCPWFDBI-UHFFFAOYSA-N 2,2,2-trifluoroethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC(F)(F)F DRVMZMGCPWFDBI-UHFFFAOYSA-N 0.000 description 1
- COUNGVKBYIDUNU-UHFFFAOYSA-N 2,2,2-trifluoroethyl dihydrogen phosphite Chemical compound OP(O)OCC(F)(F)F COUNGVKBYIDUNU-UHFFFAOYSA-N 0.000 description 1
- AFWWWFSKAZUBBF-UHFFFAOYSA-N 2,2-difluoropropanoic acid methyl 2,2-difluoroacetate Chemical compound CC(C(=O)O)(F)F.FC(C(=O)OC)F AFWWWFSKAZUBBF-UHFFFAOYSA-N 0.000 description 1
- IFDLFCDWOFLKEB-UHFFFAOYSA-N 2-methylbutylbenzene Chemical compound CCC(C)CC1=CC=CC=C1 IFDLFCDWOFLKEB-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- LSUWCXHZPFTZSF-UHFFFAOYSA-N 4-ethyl-5-methyl-1,3-dioxolan-2-one Chemical compound CCC1OC(=O)OC1C LSUWCXHZPFTZSF-UHFFFAOYSA-N 0.000 description 1
- AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 1
- AUXJVUDWWLIGRU-UHFFFAOYSA-N 4-propyl-1,3-dioxolan-2-one Chemical compound CCCC1COC(=O)O1 AUXJVUDWWLIGRU-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 1
- NKUCLZQUSAKGSB-UHFFFAOYSA-N C(C)C(C(=O)O)(F)F.FC(C(=O)OCC)F Chemical compound C(C)C(C(=O)O)(F)F.FC(C(=O)OCC)F NKUCLZQUSAKGSB-UHFFFAOYSA-N 0.000 description 1
- 229910000925 Cd alloy Inorganic materials 0.000 description 1
- 101500011076 Diploptera punctata Allatostatin-8 Proteins 0.000 description 1
- 239000002000 Electrolyte additive Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- XDRUGIUTLFHQSR-UHFFFAOYSA-N FC(CCC(=O)O)F.C(C)(=O)OCC(F)F Chemical compound FC(CCC(=O)O)F.C(C)(=O)OCC(F)F XDRUGIUTLFHQSR-UHFFFAOYSA-N 0.000 description 1
- 229910005793 GeO 2 Inorganic materials 0.000 description 1
- 229910004406 Li(Ni0.6Mn0.2CO0.2)O2 Inorganic materials 0.000 description 1
- 229910004427 Li(Ni0.7Mn0.15Co0.15)O2 Inorganic materials 0.000 description 1
- 229910002999 Li(Ni0.8Co0.1Mn0.1)O2 Inorganic materials 0.000 description 1
- 229910004437 Li(Ni0.8Mn0.1Co0.1)O2 Inorganic materials 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 1
- 229910011281 LiCoPO 4 Inorganic materials 0.000 description 1
- 229910010941 LiFSI Inorganic materials 0.000 description 1
- 229910010707 LiFePO 4 Inorganic materials 0.000 description 1
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 description 1
- 229910014689 LiMnO Inorganic materials 0.000 description 1
- 229910013131 LiN Inorganic materials 0.000 description 1
- 229910013290 LiNiO 2 Inorganic materials 0.000 description 1
- 229910012424 LiSO 3 Inorganic materials 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 229910008326 Si-Y Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910006773 Si—Y Inorganic materials 0.000 description 1
- 229910020997 Sn-Y Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910008859 Sn—Y Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- RLTFLELMPUMVEH-UHFFFAOYSA-N [Li+].[O--].[O--].[O--].[V+5] Chemical compound [Li+].[O--].[O--].[O--].[V+5] RLTFLELMPUMVEH-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000006183 anode active material Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021475 bohrium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000011329 calcined coke Substances 0.000 description 1
- 239000006257 cathode slurry Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZIISGGOPQWHYDA-UHFFFAOYSA-N difluorooxyborinic acid Chemical compound B(O)(OF)OF ZIISGGOPQWHYDA-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 229910021479 dubnium Inorganic materials 0.000 description 1
- TUQRJUNPNIYMDR-UHFFFAOYSA-N ethane-1,2-disulfonyl fluoride Chemical compound FS(=O)(=O)CCS(F)(=O)=O TUQRJUNPNIYMDR-UHFFFAOYSA-N 0.000 description 1
- ZURBXAODXJUMNV-UHFFFAOYSA-N ethyl 2,2,2-trifluoroacetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)C(F)(F)F ZURBXAODXJUMNV-UHFFFAOYSA-N 0.000 description 1
- DBOFMRQAMAZKQY-UHFFFAOYSA-N ethyl 2,2,3,3,3-pentafluoropropanoate Chemical compound CCOC(=O)C(F)(F)C(F)(F)F DBOFMRQAMAZKQY-UHFFFAOYSA-N 0.000 description 1
- PSRZMXNNQTWAGB-UHFFFAOYSA-N ethyl 4,4,4-trifluorobutanoate Chemical compound CCOC(=O)CCC(F)(F)F PSRZMXNNQTWAGB-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QKBJDEGZZJWPJA-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound [CH2]COC(=O)OCCC QKBJDEGZZJWPJA-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N germanium monoxide Inorganic materials [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000007770 graphite material Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910021385 hard carbon Inorganic materials 0.000 description 1
- 229910021473 hassium Inorganic materials 0.000 description 1
- LNLFLMCWDHZINJ-UHFFFAOYSA-N hexane-1,3,6-tricarbonitrile Chemical compound N#CCCCC(C#N)CCC#N LNLFLMCWDHZINJ-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 1
- DEUISMFZZMAAOJ-UHFFFAOYSA-N lithium dihydrogen borate oxalic acid Chemical compound B([O-])(O)O.C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.[Li+] DEUISMFZZMAAOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000686 lithium vanadium oxide Inorganic materials 0.000 description 1
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000006051 mesophase pitch carbide Substances 0.000 description 1
- GBPVMEKUJUKTBA-UHFFFAOYSA-N methyl 2,2,2-trifluoroethyl carbonate Chemical compound COC(=O)OCC(F)(F)F GBPVMEKUJUKTBA-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- 229920001384 propylene homopolymer Polymers 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910021481 rutherfordium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 229910021477 seaborgium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- RBYFNZOIUUXJQD-UHFFFAOYSA-J tetralithium oxalate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O RBYFNZOIUUXJQD-UHFFFAOYSA-J 0.000 description 1
- ZMQDTYVODWKHNT-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphate Chemical compound FC(F)(F)COP(=O)(OCC(F)(F)F)OCC(F)(F)F ZMQDTYVODWKHNT-UHFFFAOYSA-N 0.000 description 1
- CBIQXUBDNNXYJM-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphite Chemical compound FC(F)(F)COP(OCC(F)(F)F)OCC(F)(F)F CBIQXUBDNNXYJM-UHFFFAOYSA-N 0.000 description 1
- QJMMCGKXBZVAEI-UHFFFAOYSA-N tris(trimethylsilyl) phosphate Chemical compound C[Si](C)(C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C QJMMCGKXBZVAEI-UHFFFAOYSA-N 0.000 description 1
- VMZOBROUFBEGAR-UHFFFAOYSA-N tris(trimethylsilyl) phosphite Chemical compound C[Si](C)(C)OP(O[Si](C)(C)C)O[Si](C)(C)C VMZOBROUFBEGAR-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- 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
-
- 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
-
- 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
- H01M10/0569—Liquid materials characterised by the solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
- H01M4/50—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese
- H01M4/505—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
- H01M4/52—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron
- H01M4/525—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M2004/026—Electrodes composed of, or comprising, active material characterised by the polarity
- H01M2004/028—Positive electrodes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
- H01M2300/0037—Mixture of solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to a non-aqueous electrolyte solution for a lithium secondary battery and a lithium secondary battery including the same.
- Lithium secondary batteries are applicable to various fields such as mobile devices, electronic products, electric vehicles, etc. as they can be miniaturized and have high energy density and operating voltage.
- a lithium secondary battery forms an electrode assembly by interposing a separator between a positive electrode including a positive electrode active material made of a transition metal oxide containing lithium and a negative electrode including a negative electrode active material capable of storing lithium ions, and the electrode It is manufactured by inserting the assembly into a battery case, injecting a non-aqueous electrolyte that serves as a medium for delivering lithium ions, and then sealing it.
- propylene carbonate As the organic solvent of the non-aqueous electrolyte, propylene carbonate has been mainly used, but recently ethylene carbonate has been widely used to solve the problem that propylene carbonate can cause an irreversible decomposition reaction with graphite materials.
- ethylene carbonate has a high melting point, which limits its use temperature, and has another problem that can lead to significant degradation in battery performance at low temperatures. Therefore, it is required to develop an electrolyte solution for a lithium secondary battery capable of stably driving in various environments by supplementing these problems.
- An object of the present invention is to provide a non-aqueous electrolyte for a lithium secondary battery and a lithium secondary battery including the same, which reduce gas generation at high temperatures by including a phosphonium salt additive and contribute to improving rapid charging performance and low-temperature output characteristics.
- the present invention is a lithium salt; organic solvent; And it provides a non-aqueous electrolyte solution for a lithium secondary battery comprising a compound represented by Formula 1 below.
- R1 to R3 are each independently a fluorine-substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a fluorine-substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms; a fluorine-substituted or unsubstituted alkynyl group having 2 to 6 carbon atoms; or -R'OSi(R4) 3 ;
- R' is a direct bond; An alkylene group having 1 to 6 carbon atoms unsubstituted or substituted with fluorine; An alkenylene group having 2 to 6 carbon atoms unsubstituted or substituted with fluorine; Or an alkynylene group having 2 to 6 carbon atoms unsubstituted or substituted with fluorine,
- R4 is an alkyl group having 1 to 6 carbon atoms
- L1 is -(CO) m O(CH 2 ) n -
- n 0 or 1
- n is an integer from 0 to 5;
- a - is (CF 3 SO 2 ) 2 N - , (FSO 2 ) 2 N - , PF 6 - , PO 2 F 2 - , BF 4 - , ClO 4 - , (C 2 O 4 )BF 2 - , HSO 4 - , CF 3 SO 3 - , (C 2 F 5 SO 2 ) 2 N - , C(CF 2 SO 2 ) 3 - , AsF 6 - , SbF 6 - , AlCl 4 - , NbF 6 - or CF 3 CO 2 - is.
- the present invention provides a positive electrode including a positive electrode active material; a negative electrode including a negative electrode active material; a separator interposed between the anode and cathode; And it provides a lithium secondary battery comprising the non-aqueous electrolyte for the lithium secondary battery.
- the present invention can provide a non-aqueous electrolyte solution for a lithium secondary battery that contributes to strengthening a film on an electrode as bulk properties are improved through interaction with a solvent by including a phosphonium salt additive.
- the non-aqueous electrolyte for a lithium secondary battery by including the non-aqueous electrolyte for a lithium secondary battery, it is possible to provide a lithium secondary battery with excellent capacity retention rate and low-temperature output during rapid charging and low gas generation during high-temperature storage.
- a non-aqueous electrolyte for a lithium secondary battery has a problem in that output characteristics are lowered in a low temperature environment due to the limitation of operating temperature and the amount of gas generated when stored at a high temperature increases.
- the phosphonium salt additive contributes to improving the bulk properties of the electrolyte through interaction with the electrolyte solvent, and can improve temperature sensitivity by reducing side reactions with the solvent through film modification at the anode. Accordingly, it was confirmed that the performance in a low-temperature environment and the amount of gas generated during high-temperature storage can be reduced.
- the phosphonium salt additive contains a reducible alkyne functional group at the terminal, it can act on not only the positive electrode but also the negative electrode, and has a lower resistance than the resistance of the electrode film formed by the conventional electrolyte solution and additives for lithium secondary batteries. Since a film can be formed, it has been found that battery performance such as lifespan during rapid charging can be improved as the movement of Li + becomes smooth.
- the present invention is a lithium salt; organic solvent; And it provides a non-aqueous electrolyte solution for a lithium secondary battery containing the compound represented by Formula 1.
- the non-aqueous electrolyte for a lithium secondary battery of the present invention includes a compound represented by Formula 1 below.
- R1 to R3 are each independently a fluorine-substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a fluorine-substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms; a fluorine-substituted or unsubstituted alkynyl group having 2 to 6 carbon atoms; or -R'OSi(R4) 3 ;
- R' is a direct bond; An alkylene group having 1 to 6 carbon atoms unsubstituted or substituted with fluorine; An alkenylene group having 2 to 6 carbon atoms unsubstituted or substituted with fluorine; Or an alkynylene group having 2 to 6 carbon atoms unsubstituted or substituted with fluorine,
- R4 is an alkyl group having 1 to 6 carbon atoms
- L1 is -(CO) m O(CH 2 ) n -
- n 0 or 1
- n is an integer from 0 to 5;
- a - is (CF 3 SO 2 ) 2 N - , (FSO 2 ) 2 N - , PF 6 - , PO 2 F 2 - , BF 4 - , ClO 4 - , (C 2 O 4 )BF 2 - , HSO 4 - , CF 3 SO 3 - , (C 2 F 5 SO 2 ) 2 N - , C(CF 2 SO 2 ) 3 - , AsF 6 - , SbF 6 - , AlCl 4 - , NbF 6 - or CF 3 CO 2 - is.
- the L1 may be -O(CH 2 ) n - or -COO(CH 2 ) n -.
- the compound represented by Chemical Formula 1 may be represented by Chemical Formula 1-1 or Chemical Formula 1-2.
- R1 to R3, n and A - are as defined in Formula 1 above.
- R1 to R3 are each independently -R'OSi(CH 3 ) 3 , and R' is a direct bond or an alkylene group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms. Of may be an alkylene group, more preferably a methylene group.
- each of R1 to R3 may be an ethylene group.
- the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 1A to 1D.
- a - may be (CF 3 SO 2 ) 2 N - or (FSO 2 ) 2 N - .
- thermal stability is excellent and it may have low resistance.
- the content of the compound represented by Formula 1 is 0.05% to 5% by weight, preferably 0.1% to 3% by weight, more preferably 0.1% to 3% by weight based on the total weight of the non-aqueous electrolyte. 0.5% to 2% by weight.
- the content of the compound represented by Formula 1 is less than 0.05% by weight, the effect of improving fast charging performance and film improvement is insignificant, and when it exceeds 5% by weight, resistance due to decomposition of the compound represented by Formula 1 increases and degradation of oxidative stability may occur. Therefore, the content of the compound represented by Formula 1 preferably satisfies the above range.
- the non-aqueous electrolyte of the present invention is used to prevent electrode collapse caused by decomposition of the electrolyte in a high voltage environment, or to further improve low-temperature high-rate discharge characteristics, high-temperature stability, overcharge prevention, and high-temperature battery expansion suppression effect, etc.
- the following additives may optionally be further included.
- the additives include carbonate-based compounds, sultone-based compounds, sulfate-based compounds, phosphate-based or phosphite-based compounds, nitrile-based compounds, amine-based compounds, silane-based compounds, benzene-based compounds, lithium salt-based compounds, imidazole-based compounds, and ether-based compounds. It may be any one or more selected from the group consisting of compounds.
- the carbonate-based compound may be at least one selected from the group consisting of ethylene carbonate (EC), vinylene carbonate (VC), vinyl ethylene carbonate (VEC), fluoroethylene carbonate (FEC), and methyl prop-2-ynyl carbonate And, specifically, it may be vinylene carbonate.
- the sultone-based compound is a material capable of forming a stable SEI film by a reduction reaction on the surface of an anode, and includes 1,3-propane sultone (PS), 1,4-butane sultone, ethensultone, 1,3-propene sultone ( PRS), 1,4-butene sultone, and 1-methyl-1,3-propene sultone.
- PS 1,3-propane sultone
- PRS 1,3-propene sultone
- 1-methyl-1,3-propene sultone 1,3-propane sultone
- the sulfate-based compound is a material capable of forming a stable SEI film that is electrically decomposed on the surface of the anode and does not crack even when stored at high temperature, and includes ethylene sulfate (Esa), trimethylene sulfate (TMS) and methyltrimethylene. It may be any one or more selected from the group consisting of sulfate (Methyl trimethylene sulfate; MTMS).
- the phosphate or phosphite-based compound is lithium difluoro (bisoxalato) phosphate, lithium difluorophosphate, tris (trimethyl silyl) phosphate, tris (trimethyl silyl) phosphite, tris (2,2,2- trifluoroethyl)phosphate And it may be at least one selected from the group consisting of tris (trifluoroethyl) phosphite.
- the nitrile-based compound is succinonitrile (SN), adiponitrile (ADN), acetonitrile, propionitrile, butyronitrile, valeronitrile, caprylonitrile, heptanenitrile, cyclopentane carbonitrile, cyclohexane carbonitrile , 2-fluorobenzonitrile, 4-fluorobenzonitrile, difluorobenzonitrile, trifluorobenzonitrile, phenylacetonitrile, 2-fluorophenylacetonitrile, 4-fluorophenylacetonitrile, ethylene glycol bis (propionitrile) ether (ASA3), 1,3,6-hexane tricarbonitrile (HTCN), 1,4-dicyano 2-butene (DCB) and 1,2,3-tris(2-cyano It may be at least one selected from the group consisting of ethyl) propane (TCEP).
- TCEP ethyl) propane
- the amine-based compound may be triethanolamine, ethylenediamine, or a mixture thereof, and the silane-based compound may be tetravinylsilane.
- the benzene-based compound may be at least one selected from the group consisting of fluorobenzene (FB), difluorobenzene, trifluorobenzene, tetrafluorobenzene, and hexafluorobenzene.
- FB fluorobenzene
- difluorobenzene difluorobenzene
- trifluorobenzene trifluorobenzene
- tetrafluorobenzene hexafluorobenzene
- the lithium salt-based compound is a compound different from the lithium salt included in the electrolyte, and includes lithium difluorophosphate (LiDFP; LiPO 2 F 2 ), lithium bisoxalate borate (LiBOB; LiB (C 2 O 4 ) 2 ), lithium group consisting of tetrafluoroborate (LiBF 4 ), lithium difluoro(oxalato)borate (LiODFB), lithium tetraphenylborate and lithium difluoro(bisoxalato)phosphate (LiDFOP) It may be any one or more compounds selected from.
- LiDFP lithium difluorophosphate
- LiPO 2 F 2 lithium bisoxalate borate
- LiBOB LiB (C 2 O 4 ) 2
- LiODFB lithium difluoro(oxalato)borate
- LiDFOP lithium difluoro(bisoxalato)
- the imidazole-based compound may be propargyl 1H-imidazole-1-carboxylate.
- the ether-based compound is 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (1,1,2,2-Tetrafluoroethyl-2,2,2trifluoroethylether), bis (tri Fluoromethyl) -1,3-dioxolane (Bis (trifluoromethyl) -1,3-dioxolane) and 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether (1,1,2,2-Tetrafluoroethyl-2,2,3,3-tetrafluoropropylether) may be any one or more selected from the group consisting of.
- the non-aqueous electrolyte solution includes vinylene carbonate (VC), 1,3-propanesultone (PS), vinylethylene carbonate (VEC), fluoroethylene carbonate (FEC), lithium difluoro oxalato borate , ethylene sulfate (ESa), propargyl 1H-imidazole-1-carboxylate, methyl prop-2-ynyl carbonate, ethylene glycol bis(propionitrile) ether, fluorobenzene, difluorobenzene, hexafluoro Lowbenzene, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, bis(trifluoromethyl)-1,3-dioxolane and 1,1,2,2 -Tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether may further include any one or more additives selected from the group consisting of,
- the content of the additive may be 0.1 wt% to 10 wt%, preferably 0.3 wt% to 5 wt%, based on the total weight of the non-aqueous electrolyte.
- the content of the additive is within the above range, there is an effect of suppressing side reactions through film formation on the positive electrode and the negative electrode.
- the non-aqueous electrolyte solution of the present invention contains an organic solvent.
- the organic solvent various organic solvents commonly used in lithium electrolytes may be used without limitation.
- the organic solvent may be a cyclic carbonate-based solvent, a linear carbonate-based solvent, a linear ester-based solvent, a cyclic ester-based solvent, a nitrile-based solvent, a fluorine-based solvent, or a mixture thereof.
- the organic solvent may be a mixture of a cyclic carbonate-based solvent and a linear carbonate-based solvent, and in this case, an electrolyte solution having high ionic conductivity may be prepared.
- the cyclic carbonate-based solvent is a high-viscosity organic solvent and has an advantage of being able to dissociate the lithium salt in the electrolyte well due to its high dielectric constant, and is ethylene carbonate (EC), propylene carbonate (PC), 1,2-butylene carbonate, 2, It may be at least one selected from the group consisting of 3-butylene carbonate, 1,2-pentylene carbonate, 2,3-pentylene carbonate and vinylene carbonate, and preferably, it may be ethylene carbonate (EC).
- EC ethylene carbonate
- PC propylene carbonate
- 1,2-butylene carbonate 2 It may be at least one selected from the group consisting of 3-butylene carbonate, 1,2-pentylene carbonate, 2,3-pentylene carbonate and vinylene carbonate, and preferably, it may be ethylene carbonate (EC).
- the linear carbonate-based solvent is an organic solvent having a low viscosity and low dielectric constant, and includes dimethyl carbonate (DMC), diethyl carbonate (DEC), dipropyl carbonate, ethylmethyl carbonate (EMC), methyl It may be at least one selected from the group consisting of propyl carbonate and ethylpropyl carbonate, preferably dimethyl carbonate (DMC).
- DMC dimethyl carbonate
- DEC diethyl carbonate
- EMC ethylmethyl carbonate
- DMC dimethyl carbonate
- the linear ester solvent may be at least one selected from the group consisting of methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate (EP), propyl propionate (PP) and butyl propionate, , preferably ethyl propionate, propyl propionate or a mixture thereof.
- the cyclic ester-based solvent may be at least one selected from the group consisting of ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -valerolactone, and ⁇ -caprolactone.
- the nitrile solvent is succinonitrile, acetonitrile, propionitrile, butyronitrile, valeronitrile, caprylonitrile, heptanenitrile, cyclopentane carbonitrile, cyclohexane carbonitrile, 2-fluorobenzonitrile, 4- It may be at least one selected from the group consisting of fluorobenzonitrile, difluorobenzonitrile, trifluorobenzonitrile, phenylacetonitrile, 2-fluorophenylacetonitrile and 4-fluorophenylacetonitrile, preferably It may be succinonitrile.
- the fluorine-based solvent is 1,1,2,2-tetrafluoroethyl 2,2,3,3-tetrafluoropropyl ether (1,1,2,2-Tetrafluoroethyl 2,2,3,3-Tetrafluoropropyl Ether) , 2,2-bis (trifluoromethyl) -1,3-dioxolane (2,2-Bis (trifluoromethyl) -1,3-dioxolane), 1,1,2,2-tetrafluoroethyl 2 ,2,2-Tetrafluoroethyl 2,2,2-trifluoroethyl ether, Trifluoroethyl phosphate, Trifluoroethyl phosphite , Ethyl 4,4,4-trifluorobutyrate, 1,2-ethanedisulfonyl difluoride, ethyl trifluoroacetate trifluoroacetate), ethyl pentafluoropropanoate
- the remainder of the total weight of the non-aqueous electrolyte may be an organic solvent unless otherwise specified.
- the non-aqueous electrolyte of the present invention contains a lithium salt.
- the lithium salt those commonly used in electrolytes for lithium secondary batteries may be used without limitation.
- the lithium salt includes Li + as a cation and F - , Cl - , Br - , I - , and NO as an anion.
- the lithium salt is LiPF 6 , LiClO 4 , LiBF 4 , LiN(FSO 2 ) 2 (LiFSI), LiTFSI, lithium bis(pentafluoroethanesulfonyl)imide (LiBETI) , LiSO 3 CF 3 , LiPO 2 F 2 , Lithium bis(oxalate)borate (LiBOB), Lithium difluoro(oxalate)borate (LiODFB), lithium Lithium difluoro(bisoxalato) phosphate (LiDFOP), lithium tetrafluoro(oxalate) phosphate (LiTFOP), and lithium fluoromalonato (difluoro ) may be at least one selected from the group consisting of lithium fluoromalonato (difluoro) borate (LiFMDFB), preferably LiPF 6 .
- LiFMDFB lithium fluoromalonato
- the concentration of the lithium salt in the non-aqueous organic solution containing the lithium salt and an organic solvent may be 0.5 to 4.0M, specifically 0.5M to 3.0M, and more specifically 0.8M to 2.0M. there is.
- concentration of the lithium salt satisfies the above range, it is possible to obtain an electrolyte solution having appropriate impregnability by preventing excessive increase in viscosity and surface tension while sufficiently securing effects of improving low-temperature output and cycle characteristics.
- the lithium secondary battery according to the present invention includes a positive electrode including a positive electrode active material, a negative electrode including a negative electrode active material, a separator interposed between the positive electrode and the negative electrode, and a non-aqueous electrolyte solution, wherein the non-aqueous electrolyte solution is the non-aqueous electrolyte according to the present invention.
- a positive electrode including a positive electrode active material a negative electrode including a negative electrode active material
- a separator interposed between the positive electrode and the negative electrode and a non-aqueous electrolyte solution
- the non-aqueous electrolyte solution is the non-aqueous electrolyte according to the present invention.
- the positive electrode according to the present invention includes a positive electrode active material, and may be prepared by coating a positive electrode slurry including a positive electrode active material, a binder, a conductive material, and a solvent on a positive electrode current collector, followed by drying and rolling.
- the positive current collector is not particularly limited as long as it has conductivity without causing chemical change in the battery, and is, for example, stainless steel; aluminum; nickel; titanium; calcined carbon; Alternatively, aluminum or stainless steel surface treated with carbon, nickel, titanium, silver, or the like may be used.
- the cathode active material is a compound capable of reversible intercalation and deintercalation of lithium, LCO (LiCoO 2 ); LNO (LiNiO 2 ); LMO (LiMnO 2 ); LiMn 2 O 4 , LiCoPO 4 ; LFP (LiFePO 4 ); and lithium composite transition metal oxides including nickel (Ni), cobalt (Co), and manganese (Mn).
- LCO LiCoO 2
- LNO LiNiO 2
- LMO LiMnO 2
- LiMn 2 O 4 LiCoPO 4
- LFP LiFePO 4
- lithium composite transition metal oxides including nickel (Ni), cobalt (Co), and manganese (Mn).
- the cathode active material is a lithium composite transition metal having a nickel content of 60 mol% or more, preferably 70 mol% or more, more preferably 80 mol% or more based on the total metals except lithium. may be an oxide.
- the positive electrode active material may include a lithium composite transition metal oxide represented by Formula 2 below.
- M is W, Cu, Fe, V, Cr, Ti, Zr, Zn, Al, In, Ta, Y, La, Sr, Ga, Sc, Gd, Sm, Ca, Ce, Nb, Mg, B and Mo At least one selected from the group consisting of
- the 1+x indicates a molar ratio of lithium in the lithium composite transition metal oxide, and may be -0.1 ⁇ x ⁇ 0.2 or 0 ⁇ x ⁇ 0.2. When the molar ratio of lithium satisfies the above range, the crystal structure of the lithium composite transition metal oxide may be stably formed.
- the a represents the molar ratio of nickel among all metals except lithium in the lithium composite transition metal oxide, and may be 0.60 ⁇ a ⁇ 1, 0.70 ⁇ a ⁇ 1, or 0.80 ⁇ a ⁇ 1. When the molar ratio of nickel satisfies the above range, high energy density is exhibited and high capacity can be realized.
- the b represents the molar ratio of cobalt in all metals except lithium in the lithium composite transition metal oxide, and may be 0 ⁇ b ⁇ 0.30, 0 ⁇ b ⁇ 0.20, or 0 ⁇ b ⁇ 0.10. When the molar ratio of cobalt satisfies the above range, good resistance characteristics and output characteristics may be implemented.
- the c represents the molar ratio of manganese among all metals except lithium in the lithium nickel cobalt-based composite oxide, and may be 0 ⁇ c ⁇ 0.30, 0 ⁇ c ⁇ 0.20, or 0 ⁇ c ⁇ 0.10.
- the positive electrode active material exhibits excellent structural stability.
- the lithium nickel cobalt-based composite oxide is W, Cu, Fe, V, Cr, Ti, Zr, Zn, Al, In, Ta, Y, La, Sr, Ga, Sc, Gd , Sm, Ca, Ce, Nb, Mg, may include one or more doping elements selected from the group consisting of B and Mo, preferably Al as the doping element.
- d representing the molar ratio of the doping element among all metals except lithium in the lithium composite transition metal oxide may be 0 ⁇ d ⁇ 0.08, 0 ⁇ d ⁇ 0.05, or 0 ⁇ d ⁇ 0.03.
- the lithium composite transition metal oxide may be Li(Ni 0.6 Mn 0.2 Co 0.2 )O 2 , Li(Ni 0.7 Mn 0.15 Co 0.15 )O 2 , Li(Ni 0.8 Mn 0.1 Co 0.1 )O 2 and Li(Ni 0.9 Mn 0.03 Co 0.06 Al 0.01 ) O 2 It may be any one or more selected from the group consisting of.
- the cathode active material may be included in an amount of 80 wt% to 99 wt%, specifically 90 wt% to 99 wt%, based on the total weight of the solid content in the cathode slurry. In this case, when the content of the cathode active material is 80% by weight or less, the energy density may be lowered and the capacity may be lowered.
- the binder is a component that assists in the binding of the active material and the conductive material and the current collector, and may be typically added in an amount of 1% to 30% by weight based on the total weight of solids in the positive electrode slurry.
- binders include polyvinylidene fluoride, polyvinyl alcohol, carboxymethylcellulose (CMC), starch, hydroxypropylcellulose, regenerated cellulose, polyvinylpyrrolidone, polytetrafluoroethylene , polyethylene, polypropylene, ethylene-propylene-diene monomer, sulfonated ethylene-propylene-diene monomer, styrene-butadiene rubber, fluororubber, or various copolymers thereof.
- the conductive material is a material that imparts conductivity to the battery without causing chemical change, and may be added in an amount of 0.5% to 20% by weight based on the total weight of the solid content in the positive electrode slurry.
- the conductive material examples include carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black and thermal black; graphite powders such as natural graphite, artificial graphite, carbon nanotubes and graphite; conductive fibers such as carbon fibers and metal fibers; conductive powders such as fluorocarbon powder, aluminum powder, and nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; And it may be any one or more selected from the group consisting of conductive materials such as polyphenylene derivatives.
- carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black and thermal black
- graphite powders such as natural graphite, artificial graphite, carbon nanotubes and graphite
- conductive fibers such as carbon fibers and metal fibers
- conductive powders such as fluorocarbon powder, aluminum powder, and nickel powder
- conductive whiskers such as zinc oxide and potassium titanate
- the solvent of the positive electrode slurry may include an organic solvent such as NMP (N-methyl-2-pyrrolidone), and may be used in an amount that provides a desired viscosity when the positive electrode active material, binder, and conductive material are included.
- NMP N-methyl-2-pyrrolidone
- the solids concentration in the positive electrode slurry including the positive electrode active material, the binder, and the conductive material may be 40% to 90% by weight, preferably 50% to 80% by weight.
- the negative electrode according to the present invention includes a negative electrode active material, and may be prepared by coating a negative electrode slurry including a negative electrode active material, a binder, a conductive material, and a solvent on a negative electrode current collector, followed by drying and rolling.
- the negative electrode according to the present invention includes a negative electrode active material, and may be prepared by coating a negative electrode slurry including a negative electrode active material, a binder, a conductive material, and a solvent on a negative electrode current collector, followed by drying and rolling.
- the anode current collector generally has a thickness of 3 ⁇ m to 500 ⁇ m.
- the negative electrode current collector is not particularly limited as long as it does not cause chemical change in the battery and has high conductivity, and examples include copper; stainless steel; aluminum; nickel; titanium; calcined carbon; What surface-treated the surface of copper or stainless steel with carbon, nickel, titanium, silver, etc.; Alternatively, an aluminum-cadmium alloy or the like may be used.
- fine irregularities may be formed on the surface to enhance the bonding strength of the negative electrode active material, and may be used in various forms such as films, sheets, foils, nets, porous bodies, foams, and nonwoven fabrics.
- the anode active material may include a carbon material capable of reversibly intercalating/deintercalating lithium ions; metals or alloys of these metals with lithium; metal composite oxides; materials capable of doping and undoping lithium; lithium metal; And it may include any one or more selected from the group consisting of transition metal oxides.
- any carbon-based negative electrode active material commonly used in lithium ion secondary batteries may be used without particular limitation, and typical examples thereof include crystalline carbon, Amorphous carbon or a combination thereof may be used.
- the crystalline carbon include graphite such as amorphous, plate-like, flake-like, spherical or fibrous natural graphite or artificial graphite, and examples of the amorphous carbon include soft carbon (low-temperature calcined carbon). , hard carbon, mesophase pitch carbide, calcined coke, and the like.
- Examples of the above metals or alloys of these metals and lithium include Cu, Ni, Na, K, Rb, Cs, Fr, Be, Mg, Ca, Sr, Si, Sb, Pb, In, Zn, Ba, Ra, Ge, Al And a metal selected from the group consisting of Sn or an alloy of these metals and lithium may be used.
- metal composite oxide examples include PbO, PbO 2 , Pb 2 O 3 , Pb 3 O 4 , Sb 2 O 3 , Sb 2 O 4 , Sb 2 O 5 , GeO, GeO 2 , Bi 2 O 3 , Bi 2 O 4 , Bi 2 O 5 , Li x Fe 2 O 3 (0 ⁇ x ⁇ 1), Li x WO 2 (0 ⁇ x ⁇ 1) and Sn x Me 1-x Me' y O z (Me: Mn, Fe, Pb, Ge; Me': Al, B, P, Si, Groups 1, 2, and 3 elements of the periodic table, halogen; 0 ⁇ x ⁇ 1;1 ⁇ y ⁇ 3; 1 ⁇ z ⁇ 8) Any one or more selected from may be used.
- Materials capable of doping and undoping the lithium include Si, SiO x (0 ⁇ x ⁇ 2), Si—Y alloy (wherein Y is an alkali metal, an alkaline earth metal, a group 13 element, a group 14 element, a transition metal, It is an element selected from the group consisting of rare earth elements and combinations thereof, but not Si), Sn, SnO 2 , Sn—Y (Y is an alkali metal, an alkaline earth metal, a group 13 element, a group 14 element, a transition metal, and a rare earth element). It is an element selected from the group consisting of elements and combinations thereof, but not Sn), and the like, and at least one of these and SiO 2 may be mixed and used.
- the element Y is Mg, Ca, Sr, Ba, Ra, Sc, Y, Ti, Zr, Hf, Rf, V, Nb, Ta, Db (dubnium), Cr, Mo, W, Sg, Tc, Re, Bh , Fe, Pb, Ru, Os, Hs, Rh, Ir, Pd, Pt, Cu, Ag, Au, Zn, Cd, B, Al, Ga, Sn, In, Ge, P, As, Sb, Bi, S , Se, Te, Po, and combinations thereof.
- transition metal oxide examples include lithium-containing titanium composite oxide (LTO), vanadium oxide, and lithium vanadium oxide.
- the negative electrode active material may be included in an amount of 80% to 99% by weight based on the total weight of solids in the negative electrode slurry.
- the binder is a component that assists in bonding between the conductive material, the active material, and the current collector, and may be typically added in an amount of 1% to 30% by weight based on the total weight of solids in the negative electrode slurry.
- binders include polyvinylidene fluoride, polyvinyl alcohol, carboxymethylcellulose (CMC), starch, hydroxypropylcellulose, regenerated cellulose, polyvinylpyrrolidone, polytetrafluoroethylene , polyethylene, polypropylene, ethylene-propylene-diene monomer, sulfonated ethylene-propylene-diene monomer, styrene-butadiene rubber, fluororubber, or various copolymers thereof.
- the conductive material is a component for further improving the conductivity of the negative electrode active material, and may be added in an amount of 0.5% to 20% by weight based on the total weight of the solid content in the negative electrode slurry.
- the conductive material is not particularly limited as long as it has conductivity without causing chemical change in the battery, and examples thereof include carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black; graphite powders such as natural graphite, artificial graphite, carbon nanotubes and graphite; conductive fibers such as carbon fibers and metal fibers; conductive powders such as fluorocarbon powder, aluminum powder, and nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; And it may be any one or more selected from the group consisting of conductive materials such as polyphenylene derivatives.
- the solvent of the anode slurry is water; Alternatively, it may include an organic solvent such as NMP and alcohol, and may be used in an amount that provides a desired viscosity when the negative electrode active material, binder, and conductive material are included.
- the slurry containing the negative electrode active material, the binder, and the conductive material may have a solid concentration of 30 wt% to 80 wt%, preferably 40 wt% to 70 wt%.
- the lithium secondary battery according to the present invention includes a separator between the positive electrode and the negative electrode.
- the separator separates the negative electrode and the positive electrode and provides a passage for the movement of lithium ions.
- it can be used without particular limitation. It is desirable that it is excellent and has excellent safety.
- a porous polymer film as a separator for example, a porous polymer film made of polyolefin-based polymers such as ethylene homopolymer, propylene homopolymer, ethylene/butene copolymer, ethylene/hexene copolymer, and ethylene/methacrylate copolymer. ;
- a laminated structure of two or more layers thereof may be used.
- conventional porous non-woven fabrics for example, non-woven fabrics made of high-melting glass fibers, polyethylene terephthalate fibers, and the like may be used.
- a coated separator containing a ceramic component or a polymer material may be used to secure heat resistance or mechanical strength, and may be used in a single layer or multilayer structure.
- the lithium secondary battery according to the present invention as described above is a mobile phone, a notebook computer, a portable device such as a digital camera; And it can be usefully used in the electric vehicle field, such as a hybrid electric vehicle (HEV).
- HEV hybrid electric vehicle
- a battery module including the lithium secondary battery as a unit cell and a battery pack including the same are provided.
- the battery module or battery pack may include a power tool; electric vehicles, including electric vehicles (EVs), hybrid electric vehicles, and plug-in hybrid electric vehicles (PHEVs); and a power storage system.
- electric vehicles including electric vehicles (EVs), hybrid electric vehicles, and plug-in hybrid electric vehicles (PHEVs)
- PHEVs plug-in hybrid electric vehicles
- the appearance of the lithium secondary battery of the present invention is not particularly limited, but may be a cylindrical shape using a can, a prismatic shape, a pouch shape, or a coin shape.
- the lithium secondary battery according to the present invention can be used not only as a battery cell used as a power source for a small device, but also can be preferably used as a unit cell in a medium or large battery module including a plurality of battery cells.
- Anion A - is (CF 3 SO 2 ) 2 N - (TFSI - ) 1 wt% of the compound represented by Formula 1A, 2 wt% of vinylene carbonate (VC), 1 wt% of 1,3-propane sultone (PS), and 100 wt% of the non-aqueous electrolyte was prepared by mixing the non-aqueous organic solution in parts.
- Li(Ni 0.8 Co 0.1 Mn 0.1 )O 2 , a conductive material (carbon black), and a binder (polyvinylidene fluoride) as a cathode active material were added to N-methyl-2-pyrrolidone (NMP) at a ratio of 97.5:1:1.5.
- NMP N-methyl-2-pyrrolidone
- a positive electrode slurry (solid content: 60wt%) was prepared by adding in a weight ratio.
- the positive electrode slurry was applied to a 15 ⁇ m-thick aluminum (Al) thin film, which is a positive electrode current collector, and dried, and then a roll press was performed to prepare a positive electrode.
- An anode slurry (graphite blended with artificial graphite and natural graphite at a weight ratio of 8:2), a binder (SBR-CMC), and a conductive material (carbon black) is added to water as a solvent at a weight ratio of 95:3.5:1.5. Solid content: 60wt%) was prepared.
- the negative electrode slurry was applied to a 6 ⁇ m thick copper (Cu) thin film as a negative electrode current collector, dried, and then roll pressed to prepare a negative electrode.
- An electrode assembly was prepared by sequentially stacking the positive electrode, the polyolefin-based porous separator coated with inorganic particles (Al 2 O 3 ), and the negative electrode.
- a lithium secondary battery was manufactured by accommodating the assembled electrode assembly in a pouch-type battery case and injecting the prepared non-aqueous electrolyte.
- a lithium secondary battery was prepared in the same manner as in Example 1, except that the content of the compound represented by Formula 1A in which the anion A - is TFSI - was changed to 5 wt% when preparing the non-aqueous electrolyte.
- a lithium secondary solution was prepared in the same manner as in Example 1, except that the compound represented by Formula 1B in which the anion A - was TFSI - was used instead of the compound represented by Formula 1A in which the anion A - was TFSI -.
- a battery was made.
- a lithium secondary solution was prepared in the same manner as in Example 1, except that the compound represented by Formula 1C in which the anion A - was TFSI - was used instead of the compound represented by Formula 1A in which the anion A - was TFSI -.
- a battery was made.
- a lithium secondary solution was prepared in the same manner as in Example 1, except that a compound represented by Formula 1D in which the anion A - was TFSI - was used instead of the compound represented by Formula 1A in which the anion A - was TFSI - A battery was made.
- a lithium secondary battery was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula 1A in which the anion A - is TFSI - was not added when preparing the non-aqueous electrolyte.
- a lithium secondary battery was prepared in the same manner as in Example 1, except that the compound represented by the following Chemical Formula B-1 was used instead of the compound represented by Chemical Formula 1A in which the anion A is TFSI - .
- a lithium secondary battery was prepared in the same manner as in Example 1, except that the compound represented by the following Chemical Formula B- 2 was used instead of the compound represented by Chemical Formula 1A in which the anion A is TFSI - .
- the end condition was set with the voltage value for each section obtained in each section, and the charge amount when “charged” in the CC mode was recorded. Then, it was discharged again in CC mode at 0.5C to SOC 3%.
- the lithium secondary battery prepared in Examples and Comparative Examples was charged under constant current/constant voltage conditions up to 4.2V at a rate of 0.2C and charged at 0.05C cut off, and discharged at 0.2C 2.5V. It was set as the discharge capacity. Subsequently, constant current/constant voltage condition charging and 0.05C cut off charging were performed up to 4.2V at a rate of 0.2C, and residual capacity was measured after storage at 0°C for 2 weeks. The capacity retention rate (%) after storage at low temperature (0 ° C) compared to the initial discharge capacity (100%) was calculated and shown in Table 2 below.
- the batteries of Examples 1 to 6 to which the non-aqueous electrolyte solution containing the compound represented by Formula 1 as an additive was applied maintains a high charge capacity during rapid charging and has excellent output characteristics even after storage at a low temperature.
- the thermal stability is excellent with a small amount of gas generated after storage at a high temperature.
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Abstract
Description
충전 시간(sec) | C-rate(C) | |
SOC 3%~61% | 880 | 2.5 |
SOC 62%~78% | 620 | 1 |
포스포늄염 화합물 | 실험예 1 (급속 충전) |
실험예 2 (저온 보관) |
실험예 3 (고온 보관) |
||
구조 | 함량 (wt%) |
용량 유지율(%) | 용량 유지율(%) | 가스 발생량(%) | |
실시예1 | 1A (TFSI-) | 1 | 88 | 79 | 62 |
실시예2 | 1A (FSI-) | 1 | 90 | 82 | 67 |
실시예3 | 1A (TFSI-) | 5 | 84 | 73 | 58 |
실시예4 | 1B (TFSI-) | 1 | 87 | 80 | 60 |
실시예5 | 1C (TFSI-) | 1 | 94 | 82 | 79 |
실시예6 | 1D (TFSI-) | 1 | 94 | 84 | 76 |
비교예1 | 미사용 | - | 67 | 52 | 100 |
비교예2 | B-1 | 1 | 72 | 60 | 85 |
비교예3 | B-2 | 1 | 78 | 67 | 92 |
Claims (11)
- 리튬염; 유기용매; 및 하기 화학식 1로 표시되는 화합물을 포함하는 리튬 이차전지용 비수 전해액:[화학식 1]상기 화학식 1에서,R1 내지 R3는 각각 독립적으로 불소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬기; 불소로 치환 또는 비치환된 탄소수 2 내지 6의 알케닐기; 불소로 치환 또는 비치환된 탄소수 2 내지 6의 알키닐기; 또는 -R'OSi(R4)3이고,상기 R'는 직접결합; 불소로 치환 또는 비치환된 탄소수 1 내지 6의 알킬렌기; 불소로 치환 또는 비치환된 탄소수 2 내지 6의 알케닐렌기; 또는 불소로 치환 또는 비치환된 탄소수 2 내지 6의 알키닐렌기이며,상기 R4는 탄소수 1 내지 6의 알킬기이고,L1은 -(CO)mO(CH2)n-이며,m은 0 또는 1이고,n은 0 내지 5 중 어느 하나의 정수이며,A-는 (CF3SO2)2N-, (FSO2)2N-, PF6 -, PO2F2 -, BF4 -, ClO4 -, (C2O4)BF2 -, HSO4 -, CF3SO3 -, (C2F5SO2)2N-, C(CF2SO2)3 -, AsF6 -, SbF6 -, AlCl4 -, NbF6 - 또는 CF3CO2 -이다.
- 청구항 1에 있어서,상기 R1 내지 R3는 각각 독립적으로 -R'OSi(CH3)3이고,상기 R'는 직접결합 또는 탄소수 1 내지 6의 알킬렌기인 리튬 이차전지용 비수 전해액.
- 청구항 3에 있어서,상기 R'는 메틸렌기인 리튬 이차전지용 비수 전해액.
- 청구항 1에 있어서,상기 R1 내지 R3는 각각 에틸렌기인 리튬 이차전지용 비수 전해액.
- 청구항 1에 있어서,상기 A-는 (CF3SO2)2N- 또는 (FSO2)2N-인 리튬 이차전지용 비수 전해액.
- 청구항 1에 있어서,상기 화학식 1로 표시되는 화합물의 함량은 상기 비수 전해액 전체 중량을 기준으로 0.05 중량% 내지 5 중량%인 리튬 이차전지용 비수 전해액.
- 청구항 1에 있어서,에틸렌 카보네이트, 비닐렌 카보네이트, 1,3-프로판 설톤, 비닐에틸렌 카보네이트, 플루오로에틸렌 카보네이트, 및 리튬 다이플루오로 옥살레이토 보레이트, 에틸렌 설페이트, 프로파질 1H-이미다졸-1-카르복실레이트, 메틸 프로프-2-이닐 카보네이트, 에틸렌글리콜 비스(프로피오니트릴) 에테르, 플루오로벤젠, 디플루오로벤젠, 헥사플루오로벤젠, 1,1,2,2-테트라플루오로에틸-2,2,2-트리플루오로에틸에테르, 비스(트리플루오로메틸)-1,3-디옥솔란 및 1,1,2,2-테트라플루오로에틸-2,2,3,3-테트라플루오로프로필에테르로 이루어진 군에서 선택된 어느 하나 이상의 첨가제를 더 포함하는 리튬 이차전지용 비수 전해액.
- 청구항 1에 있어서,상기 유기용매는 환형 카보네이트계 용매 및 선형 카보네이트계 용매의 혼합물인 리튬 이차전지용 비수 전해액.
- 양극 활물질을 포함하는 양극;음극 활물질을 포함하는 음극;상기 양극 및 음극 사이에 개재되는 분리막; 및청구항 1의 리튬 이차전지용 비수 전해액을 포함하는 리튬 이차전지.
- 청구항 10에 있어서,상기 양극 활물질은 하기 화학식 2로 표시되는 리튬 복합 전이금속 산화물을 포함하는 것인 리튬 이차전지:[화학식 2]Li1+x(NiaCobMncMd)O2상기 화학식 2에서,M은 W, Cu, Fe, V, Cr, Ti, Zr, Zn, Al, In, Ta, Y, La, Sr, Ga, Sc, Gd, Sm, Ca, Ce, Nb, Mg, B 및 Mo로 이루어진 군에서 선택된 어느 하나 이상이고,1+x, a, b, c 및 d는 각각 독립적인 원소들의 원자분율로서,-0.2≤x≤0.2, 0.50≤a<1, 0<b≤0.40, 0<c≤0.40, 0≤d≤0.10, a+b+c+d=1이다.
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EP22870274.2A EP4293783A4 (en) | 2021-09-14 | 2022-09-14 | NON-AQUEOUS ELECTROLYTE FOR LITHIUM SECONDARY BATTERY, AND LITHIUM SECONDARY BATTERY COMPRISING SAME |
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CN117335008A (zh) * | 2023-11-28 | 2024-01-02 | 宁德时代新能源科技股份有限公司 | 电解液、锂二次电池和用电装置 |
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