CN118040044A - Electrolyte additive, electrolyte and lithium ion battery - Google Patents
Electrolyte additive, electrolyte and lithium ion battery Download PDFInfo
- Publication number
- CN118040044A CN118040044A CN202311469606.5A CN202311469606A CN118040044A CN 118040044 A CN118040044 A CN 118040044A CN 202311469606 A CN202311469606 A CN 202311469606A CN 118040044 A CN118040044 A CN 118040044A
- Authority
- CN
- China
- Prior art keywords
- electrolyte
- carbonate
- organic solvent
- additive
- lithium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003792 electrolyte Substances 0.000 title claims abstract description 56
- 239000002000 Electrolyte additive Substances 0.000 title claims abstract description 33
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 33
- -1 oxygen ions Chemical class 0.000 claims abstract description 32
- 239000000654 additive Substances 0.000 claims abstract description 26
- 230000000996 additive effect Effects 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims description 23
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 19
- 239000013538 functional additive Substances 0.000 claims description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910003002 lithium salt Inorganic materials 0.000 claims description 9
- 159000000002 lithium salts Chemical class 0.000 claims description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 150000003457 sulfones Chemical class 0.000 claims description 6
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 claims description 3
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 claims description 3
- GWAOOGWHPITOEY-UHFFFAOYSA-N 1,5,2,4-dioxadithiane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCO1 GWAOOGWHPITOEY-UHFFFAOYSA-N 0.000 claims description 3
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 claims description 3
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 claims description 3
- HJGJHDZQLWWMRT-UHFFFAOYSA-N 2,2,2-trifluoroethyl hydrogen carbonate Chemical compound OC(=O)OCC(F)(F)F HJGJHDZQLWWMRT-UHFFFAOYSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 claims description 3
- SJHAYVFVKRXMKG-UHFFFAOYSA-N 4-methyl-1,3,2-dioxathiolane 2-oxide Chemical compound CC1COS(=O)O1 SJHAYVFVKRXMKG-UHFFFAOYSA-N 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 claims description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 3
- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 3
- 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 3
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 3
- GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 claims description 3
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 claims description 3
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 claims description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- NYYFATUWNIPJTH-UHFFFAOYSA-N 1-(2-fluoroethoxy)propane Chemical compound CCCOCCF NYYFATUWNIPJTH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- UHHPUKUEMKPCII-UHFFFAOYSA-N ethyl fluoromethyl carbonate Chemical compound CCOC(=O)OCF UHHPUKUEMKPCII-UHFFFAOYSA-N 0.000 claims description 2
- GBPVMEKUJUKTBA-UHFFFAOYSA-N methyl 2,2,2-trifluoroethyl carbonate Chemical compound COC(=O)OCC(F)(F)F GBPVMEKUJUKTBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 abstract description 5
- 150000002500 ions Chemical class 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 238000004090 dissolution Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 238000011946 reduction process Methods 0.000 abstract description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007773 negative electrode material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910013716 LiNi Inorganic materials 0.000 description 2
- 125000004946 alkenylalkyl group Chemical group 0.000 description 2
- 125000005038 alkynylalkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BWUZCLFBFFQLLM-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-yl hydrogen carbonate Chemical compound FC(F)(F)C(C)OC(O)=O BWUZCLFBFFQLLM-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- DSMUTQTWFHVVGQ-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1F DSMUTQTWFHVVGQ-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 1
- 229910011279 LiCoPO4 Inorganic materials 0.000 description 1
- 229910010707 LiFePO 4 Inorganic materials 0.000 description 1
- 229910013191 LiMO2 Inorganic materials 0.000 description 1
- 229910015645 LiMn Inorganic materials 0.000 description 1
- 229910016168 LiMn1-xFexPO4 Inorganic materials 0.000 description 1
- 229910002099 LiNi0.5Mn1.5O4 Inorganic materials 0.000 description 1
- 229910018434 Mn0.5O2 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910021385 hard carbon Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000473 manganese(VI) oxide Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005543 nano-size silicon particle Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound 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
-
- 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
-
- 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
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
Abstract
The invention provides an electrolyte additive, electrolyte and a lithium ion battery, and relates to the technical field of lithium ion batteries. The electrolyte additive provided by the invention has a five-membered ring structure with N and S heteroatoms, and after the electrolyte additive is added into the electrolyte of a lithium ion battery, the additive can be subjected to ring-opening polymerization in the preferential oxidation/reduction process of the surface of a positive electrode/negative electrode to form a polymer which can stabilize the structure of the positive electrode/negative electrode and has high ion conductivity and high electrochemical stability, so that the dissolution and migration of metal ions and active oxygen ions in the positive electrode are effectively inhibited, and the direct contact between the positive electrode/negative electrode with high activity and the electrolyte is inhibited, thereby achieving the purposes of improving the structural stability of the positive electrode/negative electrode, inhibiting interface side reactions and improving the electrochemical performance of the battery.
Description
Technical Field
The invention relates to the technical field of lithium ion batteries, in particular to an electrolyte additive, an electrolyte, a preparation method and a lithium ion battery.
Background
The lithium ion battery has the advantages of high energy density, high working potential, environmental friendliness and the like, is widely applied to the fields of portable electronic equipment, electric automobiles and the like, and has great application potential in the fields of electric airplanes, military and the like. However, with the continuous development of electronic products in the intelligent, light and thin and ultra-long standby directions, and the continuous climbing requirements of large-scale equipment such as electric automobiles, electric airplanes and the like, such as long endurance and long service life, higher requirements are put forward on the cycle stability, energy density and safety of batteries.
However, the cycling stability, energy density, and safety of lithium ion batteries are primarily determined by the interfacial stability between the electrolyte and the electrodes. On the one hand, the anode commonly used at present is made of metal oxide materials, and in a deep lithium removal state, oxidized high-valence metal ions can catalyze the decomposition of electrolyte, so that metal ions are dissolved out and the structure collapses, and the process is aggravated along with the increase of the voltage of the battery and the participation of oxygen in the electrode in charge compensation. In addition, dissolved metal ions and active oxygen can migrate to the negative electrode and be reduced on the surface of the negative electrode of the battery, so that the original solid electrolyte membrane (SEI) on the surface of the negative electrode is destroyed, the interface side reaction on the negative electrode side is aggravated, and even the thermal runaway risks such as combustion, explosion and the like can be induced when serious. Therefore, improving the interface stability between the positive/negative electrode and the electrolyte is critical to the overall improvement of the battery performance.
Disclosure of Invention
The invention aims to provide an electrolyte additive, an electrolyte, a preparation method and a lithium ion battery, wherein by introducing N, S elements of the additive into a molecular structure main body frame, an interface film with high ion conductivity and high electrochemical stability can be formed on the surfaces of a positive electrode and a negative electrode, so that the interface stability between the positive electrode/the negative electrode and the electrolyte is improved, and the long-cycle performance, the energy density and the safety performance of the lithium ion battery are improved.
In a first aspect, the invention provides an electrolyte additive, which has a structure as shown in formula I:
wherein R 1 and R 2 are independently of each other substituted or unsubstituted alkyl or aryl.
In a second aspect, the invention also provides an electrolyte comprising the electrolyte additive provided above.
Optionally, the electrolyte further comprises an organic solvent and lithium salt dissolved in the organic solvent.
Optionally, the concentration of the electrolyte additive in the electrolyte is 0.1-10wt.%.
Optionally, the concentration of the lithium salt in the electrolyte is 0.2-5mol/L
Alternatively, the lithium salt includes at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (trifluoromethylsulfonate) imide, lithium bis (fluorosulfonyl) imide, lithium difluorooxalato borate, lithium bisoxalato borate, and lithium perchlorate.
Optionally, the organic solvent comprises at least one of a carbonate non-aqueous organic solvent, an ether non-aqueous organic solvent, a sulfone non-aqueous organic solvent, a nitrile non-aqueous organic solvent and a carboxylate non-aqueous organic solvent;
The carbonate nonaqueous organic solvent comprises at least one of ethylene carbonate, propylene carbonate, methyl ethyl carbonate, dimethyl carbonate, diethyl carbonate, methyl propyl carbonate, fluoroethylene carbonate, fluoromethyl ethyl carbonate, fluoropropylene carbonate, bifluoroethylene carbonate, methyl trifluoroethyl carbonate and tri (trifluoroethyl) carbonate;
The ether non-aqueous organic solvent comprises at least one of ethylene glycol dimethyl ether, pentane oxide, methyl perfluoro butyl ether, ethyl perfluoro butyl ether and fluoro ethyl propyl ether;
The sulfone nonaqueous organic solvent comprises at least one of sulfolane, dimethyl sulfoxide, n-sulfolane, dimethyl sulfone, phenyl sulfone and methyl ethyl sulfone;
The nitrile nonaqueous organic solvent comprises at least one of acetonitrile, succinonitrile, adiponitrile, octadinitrile and hexanetrinitrile;
the carboxylic acid ester nonaqueous solvent comprises at least one of ethyl acetate, methyl acetate, ethyl formate, ethyl difluoroacetate, methyl 2, 3-tetrafluoropropionate and methyl 2, 2-difluoro-2 (fluorosulfonyl) acetate.
Optionally, the electrolyte further comprises a functional additive, the concentration of the functional additive in the electrolyte being 0.1-10wt.%.
Optionally, the functional additive comprises at least one of ethylene carbonate, propylene sulfite, dimethyl sulfite, ethylene sulfate, methylene methane disulfonate, n-propyl phosphoric anhydride, triallyl phosphoric ester, succinic anhydride, and methylsulfonic anhydride.
In a third aspect, the invention also provides a lithium ion battery comprising any of the above-described optional electrolytes.
Drawings
Fig. 1 is a cycle performance chart of lithium ion batteries prepared in example 8 and comparative example 1 of the present invention;
Fig. 2 is a cycle performance chart of the lithium ion batteries prepared in example 8 and comparative example 1 of the present invention;
FIG. 3 is a graph showing cycle performance of lithium ion batteries prepared in examples 10 to 11 and comparative examples 1 to 2 according to the present invention;
fig. 4 is a cycle performance chart of the lithium ion batteries prepared in example 12 and comparative example 1 of the present invention.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. Unless otherwise defined, technical or scientific terms used herein should be given the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. As used herein, the word "comprising" and the like means that elements or items preceding the word are included in the element or item listed after the word and equivalents thereof without precluding other elements or items.
The embodiment of the invention provides an electrolyte additive, which has a structural formula shown in a formula I.
Wherein the R 1 and R 2 groups are, independently of each other, any of substituted alkyl, substituted aryl, unsubstituted alkyl and unsubstituted aryl.
In some embodiments, the unsubstituted alkyl group can be any of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropyl, and cyclobutyl.
In some embodiments, the substituted alkyl group may be any of an alkenyl alkyl group, an alkynyl alkyl group, and a haloalkyl group. In practice, the alkenylalkyl group may be any of allyl, allyl isobutyl, allyl and allyl isopentyl, the alkynylalkyl group may be any of propargyl, propargyl isobutyl, propargyl and propargyl isopentyl, and the haloalkyl group may be any of trifluoromethyl, trifluoroethyl, trifluoropropyl, pentafluoropropyl, trifluorobutyl and pentafluorobutyl.
In some embodiments, the substituted aryl group may be any of p-trifluoromethylphenyl, p-fluorophenyl, p-chlorophenyl, o-trifluoromethylphenyl, and p-fluorobenzyl.
The electrolyte additive provided by the invention has a five-membered ring structure doped with N and S heteroatoms simultaneously. When the electrolyte additive is added to the electrolyte of the lithium ion battery, the additive can be subjected to ring-opening polymerization in the preferential oxidation/reduction process of the surfaces of the positive electrode and the negative electrode to form a high polymer which can stabilize the positive electrode and the negative electrode structure and has high ion conductivity and high electrochemical stability, so that the dissolution and migration of metal ions and active oxygen ions in the positive electrode are effectively inhibited, the direct contact between the positive electrode and the negative electrode with high activity and the electrolyte is inhibited, and the purposes of improving the structural stability of the positive electrode and the negative electrode, inhibiting interface side reactions and improving the electrochemical performance of the battery are achieved.
In addition, the invention also provides an electrolyte which comprises the electrolyte additive provided in any embodiment.
In some embodiments, the concentration of the electrolyte additive in the electrolyte is 0.1-10%, and in this concentration range, the additive can achieve better performance, and when the content of the additive is lower than 0.1wt.%, it is difficult to form a uniform protective film on the surface of the positive/negative electrode due to the excessively low content, so as to isolate the direct contact between the high-reactivity electrode and the electrolyte; similarly, when the content of the additive is more than 10wt.%, the interfacial layer formed by in-situ decomposition of the additive on the positive/negative surfaces may be relatively thick, blocking ion and electron transport, and reducing battery capacity.
In some embodiments, the electrolyte further comprises an organic solvent and a lithium salt dissolved in the organic solvent, and in fact, the electrolyte additive is also dissolved in the organic solvent, together forming a stable solution.
In some embodiments, the organic solvent is a non-aqueous organic solvent commonly used in the art in preparing electrolytes. Specifically, the organic solvent may be at least one of carbonate, ether, sulfone, nitrile and carboxylate organic solvents.
More specifically, when the organic solvent is a carbonate-based organic solvent, it may be at least one of ethylene carbonate, propylene carbonate, methylethyl carbonate, dimethyl carbonate, diethyl carbonate, methylpropyl carbonate, fluoroethylene carbonate, methylethyl carbonate, fluoropropylene carbonate, bis-fluoroethylene carbonate, methyltrifluoroethyl carbonate, tris (trifluoroethyl) carbonate.
More specifically, when the organic solvent is an ether-type organic solvent, it may be at least one of ethylene glycol dimethyl ether, pentane oxide, methyl perfluorobutyl ether, ethyl perfluorobutyl ether, and fluoroethylene propyl ether.
More specifically, when the organic solvent is a sulfone-based organic solvent, it may be at least one of sulfolane, dimethyl sulfoxide, n-sulfolane, dimethyl sulfone, phenyl sulfone and methyl ethyl sulfone.
More specifically, when the organic solvent is a nitrile-based organic solvent, it may be at least one of acetonitrile, succinonitrile, adiponitrile, octadinitrile and hexanetrinitrile.
More specifically, when the organic solvent is a carboxylate organic solvent, it may be at least one of ethyl acetate, methyl acetate, ethyl formate, ethyl difluoroacetate, methyl 2, 3-tetrafluoropropionate and methyl 2, 2-difluoro-2 (fluorosulfonyl) acetate.
In some embodiments, the lithium salt dissolved in the organic solvent comprises at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (trifluoromethylsulfonate) imide, lithium bis (fluorosulfonyl) imide, lithium difluorooxalato borate, lithium bisoxalato borate, and lithium perchlorate.
In some embodiments, the concentration of lithium salt in the electrolyte is 0.2-5mol/L.
In some embodiments, functional additives are also included in the electrolyte. Specifically, the functional additive comprises at least one of ethylene carbonate, propylene sulfite, dimethyl sulfite, ethylene sulfate, methylene methane disulfonate, n-propyl phosphoric anhydride, triallyl phosphate, succinic anhydride and methylsulfonic anhydride.
In some embodiments, the concentration of the functional additive in the electrolyte is 0.1-10wt.%.
The embodiment of the invention also provides a lithium ion battery, which comprises the electrolyte in any embodiment.
In some embodiments, in the lithium ion battery, at least one of a layered oxide positive electrode represented by LiCoO 2, ternary LiNi xCoyMn1-x-yO2 (x, y >0, and x+y < 1), liNi xCoyAl1-x-yO2 (x, y >0, and x+y < 1), a lithium-rich xLi 2MnO3·(1-x)LiMO2 (m=ni, co, mn,0< x < 1), and the like, a polyanion positive electrode represented by LiFePO 4、LiMn1-xFexPO4(x<1)、LiCoPO4 and the like, a spinel positive electrode represented by LiMn 2O4、LiNi0.5Mn1.5O4 and the like, and the like; and at least one of lithium metal, graphite, silicon carbon, micro/nano silicon and other negative electrode materials, and other positive/negative electrode materials for batteries, such as Na xMO2 (M is a transition metal atom, 0< x.ltoreq.1) positive electrode, na 3V2(PO4)3 positive electrode, soft/hard carbon negative electrode and the like in a sodium ion battery, which may involve interfacial side reactions are not excluded.
Example 1
The embodiment 1 of the invention provides a preparation method of an electrolyte additive, which comprises the following steps:
95.0397mg (0.5 mmol) of 1- (4-fluorophenyl) -4-methyl-1-yn-3-one as a raw material I, 95.9651mg (0.6 mmol) of potassium ethylxanthate as a raw material II, 289.8858mg (2.0 mmol) of ammonium iodide, 9.0mg (0.5 mmol) of deionized water and 2.0mL of N, N-dimethylformamide are reacted under the air atmosphere condition for 12 hours, and 81.4097mg of electrolyte additive (NS-1 for short) is obtained by column chromatography separation and purification, and the calculated yield is 75%.
Specifically, the structural formula of the electrolyte additive NS-1 provided in the embodiment 1 is as follows:
Examples 2 to 7
Examples 2-7 of the present invention provide a method for preparing an electrolyte additive, which differs from example 1 in that (raw materials and product structures) are shown in table 1 below.
TABLE 1
Example 8
Embodiment 8 of the present invention provides a method for preparing a lithium ion battery, wherein the electrolyte additive NS-1 prepared in embodiment 1 is added, comprising the following steps:
S1, preparing electrolyte: in a glove box filled with argon, ethylene carbonate and ethylmethyl carbonate were mixed in a volume ratio of 3:7, after stirring and mixing, sequentially adding lithium hexafluorophosphate and an additive NS-1 into the mixed solution; wherein the addition amount of the lithium hexafluorophosphate is such that the concentration of the lithium hexafluorophosphate in the electrolyte is 1.2mol/L, and the addition amount of the additive NS-1 is such that the content of the additive NS-1 in the electrolyte is 1wt.%;
S2, assembling a battery: and taking ternary material LiNi 0.9Co0.5Mn0.5O2 as a positive electrode material, taking metallic lithium as a negative electrode material, respectively dripping electrolyte containing the NS-1 additive on two sides of the PP-based diaphragm, and packaging to obtain the lithium ion battery.
Example 9
The preparation method of the lithium ion battery provided in the embodiment 9 of the invention is different from the embodiment 8 in that the electrolyte additive NS-2 prepared in the embodiment 2 is added, in the step S1 of preparing the electrolyte, lithium hexafluorophosphate and the additive NS-2 are sequentially added to the mixed solution, and the additive NS-2 is added in an amount such that the content of the additive NS-2 in the electrolyte is 10wt.%.
Example 10
The preparation method of the lithium ion battery provided in the embodiment 10 of the present invention is different from the embodiment 8 in that the electrolyte additive NS-5 prepared in the embodiment 5 is added, in the step S1 of preparing the electrolyte, lithium hexafluorophosphate and the additive NS-5 are sequentially added to the mixed solution, and the additive NS-2 is added in an amount such that the content of the additive NS-2 in the electrolyte is 0.5wt.%.
Example 11
The preparation method of the lithium ion battery provided in the embodiment 11 of the invention is different from the preparation method of the embodiment 8 in that the electrolyte additive NS-5 and other functional additives of vinylene carbonate prepared in the embodiment 5 are added, lithium hexafluorophosphate and the additive NS-5 and the functional additives of vinylene carbonate are sequentially added to the mixed solution in the preparation of the electrolyte in the step S1, and the additive NS-2 and the vinylene carbonate are added in amounts such that the contents of the additive NS-2 and the vinylene carbonate in the electrolyte are 0.5wt.%.
Example 12
The preparation method of the lithium ion battery provided in the embodiment 12 of the present invention is different from the embodiment 8 in that the electrolyte additive NS-7 prepared in the embodiment 7 is added, in the step S1 of preparing the electrolyte, lithium hexafluorophosphate and the additive NS-7 are sequentially added to the mixed solution, and the additive NS-2 is added in an amount such that the content of the additive NS-7 in the electrolyte is 0.1wt.%.
Comparative example 1
Comparative example 1 of the present invention provides a method for preparing a lithium ion battery, which is different from example 8 in that the electrolyte additive NS-1 prepared as in example 1 is not added, and in preparing an electrolyte in step S1, only lithium hexafluorophosphate is added to the mixed solution.
Comparative example 2
Comparative example 1 of the present invention provides a method for preparing a lithium ion battery, which is different from example 8 in that the electrolyte additive NS-1 prepared as in example 1 is not added, and in the preparation of the electrolyte in step S1, only lithium hexafluorophosphate and the functional additive ethylene carbonate are added to the mixed solution.
Performance testing
The lithium ion batteries prepared in examples 8 to 12 and comparative examples 1 to 2 were subjected to electrochemical performance test at a rate of 1C (1c=200 mAh/g) and room temperature, with a voltage range of 3.0 to 4.3V, and the test results are shown in fig. 1 to 4.
Performance analysis
As can be seen from fig. 1, the addition of NS-1 in example 8 can significantly improve the discharge capacity and capacity retention rate after cycling of the lithium ion battery, from 71% in comparative example 1 to 89% in example 8, which is mainly beneficial to the interface film with higher ionic conductivity and electrochemical stability formed on the surface of the positive/negative material by NS-1, and can well protect the electrode and inhibit electrolyte decomposition, thereby improving the service life of the lithium ion battery.
As can be seen from fig. 2, when the amount of NS-2 added in example 9 reaches 10wt.%, the battery capacity is reduced due to the increased content of the electrolyte additive, which makes the interface layer formed on the positive/negative electrode surfaces of the additive thicker, but the capacity retention rate (78%) of the lithium ion battery in example 9 is still higher than that of comparative example 1 (71%) during long cycles, which is advantageous in promoting the cycle performance stability of the battery.
As can be seen from fig. 3, the functional additive ethylene carbonate was not added to comparative example 1 and example 10, and the functional additive ethylene carbonate was added to comparative example 2 and example 11, and the electrochemical properties of the batteries of example 10 and example 11 containing the NS-5 additive were found to be superior to those of comparative example 1 and comparative example 2.
As can be seen from fig. 4, even when the electrolyte additive NS-7 was added in an amount of only 0.1% in example 12, the battery was still lower in decay rate under long cycles than in comparative example 1, which suggests that 0.1wt% of the electrolyte additive was also capable of improving the cycle performance stability and the service life of the lithium ion battery.
While embodiments of the present invention have been described in detail hereinabove, it will be apparent to those skilled in the art that various modifications and variations can be made to these embodiments. It is to be understood that such modifications and variations are within the scope and spirit of the present invention as set forth in the following claims. Moreover, the invention described herein is capable of other embodiments and of being practiced or of being carried out in various ways.
Claims (10)
1. An electrolyte additive is characterized in that the structure of the additive is shown as a formula I:
wherein R 1 and R 2 are independently of each other substituted or unsubstituted alkyl or aryl.
2. An electrolyte comprising the electrolyte additive of claim 1.
3. The electrolyte according to claim 2, further comprising an organic solvent and a lithium salt dissolved in the organic solvent.
4. The electrolyte of claim 2 or 3, wherein the concentration of the electrolyte additive in the electrolyte is 0.1-10wt.%.
5. The electrolyte of claim 3, wherein the concentration of the lithium salt in the electrolyte is 0.2 to 5mol/L.
6. The electrolyte of claim 3 wherein the lithium salt comprises at least one of lithium hexafluorophosphate, lithium tetrafluoroborate, lithium bis (trifluoromethane sulfonate) imide, lithium bis (fluorosulfonyl) imide, lithium difluorooxalato borate, lithium bisoxalato borate, and lithium perchlorate.
7. The electrolyte according to claim 3, wherein the organic solvent comprises at least one of a carbonate-based nonaqueous organic solvent, an ether-based nonaqueous organic solvent, a sulfone-based nonaqueous organic solvent, a nitrile-based nonaqueous organic solvent, and a carboxylate-based nonaqueous organic solvent;
The carbonate nonaqueous organic solvent comprises at least one of ethylene carbonate, propylene carbonate, methyl ethyl carbonate, dimethyl carbonate, diethyl carbonate, methyl propyl carbonate, fluoroethylene carbonate, fluoromethyl ethyl carbonate, fluoropropylene carbonate, bifluoroethylene carbonate, methyl trifluoroethyl carbonate and tri (trifluoroethyl) carbonate;
The ether non-aqueous organic solvent comprises at least one of ethylene glycol dimethyl ether, pentane oxide, methyl perfluoro butyl ether, ethyl perfluoro butyl ether and fluoro ethyl propyl ether;
The sulfone nonaqueous organic solvent comprises at least one of sulfolane, dimethyl sulfoxide, n-sulfolane, dimethyl sulfone, phenyl sulfone and methyl ethyl sulfone;
The nitrile nonaqueous organic solvent comprises at least one of acetonitrile, succinonitrile, adiponitrile, octadinitrile and hexanetrinitrile:
The carboxylic acid ester nonaqueous solvent comprises at least one of ethyl acetate, methyl acetate, ethyl formate, ethyl difluoroacetate, methyl 2, 3-tetrafluoropropionate and methyl 2, 2-difluoro-2 (fluorosulfonyl) acetate.
8. The electrolyte of claim 3, further comprising a functional additive, wherein the functional additive is present in the electrolyte at a concentration of 0.1 to 10wt.%.
9. The electrolyte of claim 8 wherein the functional additive comprises at least one of ethylene carbonate, propylene sulfite, dimethyl sulfite, ethylene sulfate, methylene methane disulfonate, n-propyl phosphoric anhydride, triallyl phosphate, succinic anhydride, and methylsulfonic anhydride.
10. A lithium ion battery comprising the electrolyte according to claims 2 to 9.
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