CN105206873A - Phosphazene perfluoroalkanesulfonylimide lithium electrolyte and battery using electrolyte - Google Patents
Phosphazene perfluoroalkanesulfonylimide lithium electrolyte and battery using electrolyte Download PDFInfo
- Publication number
- CN105206873A CN105206873A CN201510454869.8A CN201510454869A CN105206873A CN 105206873 A CN105206873 A CN 105206873A CN 201510454869 A CN201510454869 A CN 201510454869A CN 105206873 A CN105206873 A CN 105206873A
- Authority
- CN
- China
- Prior art keywords
- lithium
- hcf
- carbonate
- phosphonitrile
- oroalkane sulfonyl
- 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
Links
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 40
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000003792 electrolyte Substances 0.000 title claims abstract description 30
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 title abstract 4
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 15
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 15
- 230000000996 additive effect Effects 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000011356 non-aqueous organic solvent Substances 0.000 claims abstract description 5
- 150000001335 aliphatic alkanes Chemical group 0.000 claims abstract description 3
- 150000002466 imines Chemical class 0.000 claims description 28
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims description 23
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 14
- 229910001416 lithium ion Inorganic materials 0.000 claims description 14
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 10
- 229910013870 LiPF 6 Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000007774 positive electrode material Substances 0.000 claims description 8
- 239000010439 graphite Substances 0.000 claims description 7
- 229910002804 graphite Inorganic materials 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910000733 Li alloy Inorganic materials 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 6
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical group O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 5
- 239000006258 conductive agent Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 4
- 229910013063 LiBF 4 Inorganic materials 0.000 claims description 4
- 239000011149 active material Substances 0.000 claims description 4
- 239000004917 carbon fiber Substances 0.000 claims description 4
- 229910052729 chemical element Inorganic materials 0.000 claims description 4
- 239000011258 core-shell material Substances 0.000 claims description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- 239000001989 lithium alloy Substances 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 239000011135 tin Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- 229910013684 LiClO 4 Inorganic materials 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 2
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 claims description 2
- SJHAYVFVKRXMKG-UHFFFAOYSA-N 4-methyl-1,3,2-dioxathiolane 2-oxide Chemical compound CC1COS(=O)O1 SJHAYVFVKRXMKG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000838 Al alloy Inorganic materials 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910015015 LiAsF 6 Inorganic materials 0.000 claims description 2
- 229910013075 LiBF Inorganic materials 0.000 claims description 2
- 229910013528 LiN(SO2 CF3)2 Inorganic materials 0.000 claims description 2
- 229910013872 LiPF Inorganic materials 0.000 claims description 2
- 229910012424 LiSO 3 Inorganic materials 0.000 claims description 2
- 101150058243 Lipf gene Proteins 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 239000010426 asphalt Substances 0.000 claims description 2
- 239000007767 bonding agent Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000571 coke Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- 238000005087 graphitization Methods 0.000 claims description 2
- 229910021385 hard carbon Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000002642 lithium compounds Chemical class 0.000 claims description 2
- 229910001947 lithium oxide Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 239000002931 mesocarbon microbead Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 239000006259 organic additive Substances 0.000 claims description 2
- 229920000447 polyanionic polymer Polymers 0.000 claims description 2
- BKIWAQYWKUFSRE-UHFFFAOYSA-N prop-1-ene;sulfuric acid Chemical group CC=C.OS(O)(=O)=O BKIWAQYWKUFSRE-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910021384 soft carbon Inorganic materials 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- -1 carbonate ester Chemical class 0.000 abstract description 12
- 239000007772 electrode material Substances 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 3
- 229910010707 LiFePO 4 Inorganic materials 0.000 description 3
- 229910012743 LiNi0.5Co0.3Mn0.2 Inorganic materials 0.000 description 3
- 239000005030 aluminium foil Substances 0.000 description 3
- 150000001450 anions Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 3
- 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 3
- 238000011160 research Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910013188 LiBOB Inorganic materials 0.000 description 2
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 2
- 229910015645 LiMn Inorganic materials 0.000 description 2
- 238000004146 energy storage Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000005677 organic carbonates Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910012820 LiCoO Inorganic materials 0.000 description 1
- 229910013716 LiNi Inorganic materials 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 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
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- WDGKXRCNMKPDSD-UHFFFAOYSA-N lithium;trifluoromethanesulfonic acid Chemical compound [Li].OS(=O)(=O)C(F)(F)F WDGKXRCNMKPDSD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 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
- H01M10/0568—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
- H01M10/052—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
- H01M10/05—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
- H01M10/0561—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of inorganic materials only
- H01M10/0563—Liquid materials, e.g. for Li-SOCl2 cells
-
- 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
-
- 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
- H01M2300/0088—Composites
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Secondary Cells (AREA)
Abstract
The invention provides a phosphazene perfluoroalkanesulfonylimide lithium electrolyte which includes a conductive lithium salt, a nonaqueous organic solvent and an additive, wherein the conductive lithium salt includes phosphazene perfluoroalkanesulfonylimide lithium with the structural formula being shown in the description. In the formula, M+ is Li, R1-5 = -OR7 or -M[NSO2-R6], R6 is fluorinated alkyl containing 1-8 carbon atoms, R7 is an alkanes group containing 1-10 carbon atoms. Phosphazene perfluoroalkanesulfonylimide lithium provided by the invention is good in thermal stability and hydrolysis resistance, has high electrical conductivity and oxidation potential in the traditional carbonate ester solution, and is good in compatibility with the extensively used electrode materials.
Description
Technical field
The present invention relates to lithium secondary battery field, more specifically, the present invention relates to the lithium secondary battery that a kind of electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium uses this electrolyte.
Background technology
Containing oroalkane sulfonyl imines and alkali metal salt thereof, particularly lithium salts, it is important fluoride ion compound, in the clean energy resource devices such as lithium ion battery, ultracapacitor and the aluminium electrolytic capacitor fields such as high-performance nonaqueous electrolyte material and efficient catalyst, all there is important commercial application and be worth.
At present, focus mostly in the fluorine-containing sulfimide of unitary (Coord.Chem.Revs., 1997,158,413.) about the research containing oroalkane sulfonyl imines, namely contain a sulfimide (-SO in anion structure
2nSO
2-) unit, as two (oroalkane sulfonyl) imines (H [(R
fsO
2)
2n], R
f=C
mf
2m+1, m=1-8) and alkali metal salt (M [(R
fsO
2)
2n], M=Li, Na, K, Rb, Cs), wherein that representative is two (trimethyl fluoride sulfonyl) imine lithium (Li [(CF
3sO
2)
2n], be called for short LiTFSI).Due to CF in molecule
3strong electron attraction, and sulfimide moiety (-SO
2-N-SO
2-) conjugation delocalization, make [(CF
3sO
2)
2n]
-(TFSI
-) negative electrical charge high degree of dispersion in anion, and become the organic anion of weak coordination, so make HTFSI have extremely strong acidity and oxidation-reduction resistance energy, its alkali metal salt, ionic liquid have good chemistry and electrochemical stability.
On the other hand, nonaqueous electrolytic solution is one of critical material of the energy storage devices such as high specific energy lithium ion battery, its combination property, and as chemistry and electrochemical stability, fail safe etc., directly affect the use of lithium ion battery.At present, business-like lithium-ion battery electrolytes primarily of organic carbonate as dimethyl carbonate (CH
3oCOOCH
3, DMC), diethyl carbonate (C
2h
5oCOOC
2h
5, DEC), vinyl carbonate (EC) etc., and electrolyte conducting salt (mainly LiPF
6) composition.In this system, the inflammable and effumability of organic carbonate is major security risk (as burning, blast, leaks) (J.Electrochem.Soc., 2001,148,1100 of current lithium ion battery; Chem.Rev., 2004,104,4303).Meanwhile, traditional electrolyte matter conducting salt LiPF
6due to its chemical instability (comprising thermally labile and easily hydrolysis), make to use LiPF
6(secondary) lithium ion battery when working under high temperature (>55 DEG C), cycle performance and useful life greatly reduce (Electrochem.Communs, 2005,7,669).And in other common lithium salts, as lithium perchlorate (LiClO
4), LiBF4 (LiBF
4), trifluoromethyl sulfonic acid lithium (Li [CF
3sO
3]), two (trimethyl fluoride sulfonyl) imine lithium (LiTFSI), di-oxalate lithium borate (LiBOB) etc., owing to there is the performance deficiency of different aspect respectively, as LiClO
4there is potential explosivity, LiBF
4conductivity is too low, Li [SO
3cF
3] and LiTFSI positive current collector material aluminium foil is corrosive, LiBOB solubility in carbonic ester is low, makes these lithium salts fail to obtain in lithium ion battery to widely use.Therefore, research and development chemical stability (as thermal stability, water stability etc.) are high, and chemical property is (as high conductivity, wide electrochemical window, does not have corrosivity etc. to aluminium foil) excellent novel conductive lithium salts electrolyte replaces traditional lithium salts LiPF
6it is the important research direction of exploitation large-sized power battery and large-scale energy storage electronic device.
Up to the present, about the research of group with imine moiety is containing a sulfimide (-SO containing focusing mostly on
2nSO
2-) in the chemical constitution of unit, there is not been reported for the oroalkane sulfonyl imines containing phosphazenium groups and related compound thereof.
Summary of the invention
In view of the problem existing for background technology, the object of the present invention is to provide a kind of electrolyte of phosphonitrile oroalkane sulfonyl imine lithium, this electrolyte has superior oxidation resistent susceptibility and security performance, makes lithium secondary battery have superior circulation, high-temperature storage and security performance under high voltage condition.
In order to realize technique scheme, the invention provides a kind of electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium, comprise electric conducting lithium salt, non-aqueous organic solvent and additive, electric conducting lithium salt comprises phosphonitrile oroalkane sulfonyl imine lithium, and phosphonitrile oroalkane sulfonyl imine lithium general structure is:
wherein, M+ is Li, R1-5=-OR7 or-M [NSO2-R6]; R6 to be carbon number be 1-8 containing fluoroalkyl, the alkanes group of R7 to be carbon number be 1-10.
Described R1-5 is identical or different structure.
Described R
6for F, CF
3, CF
3cH
2, CF
2hCH
2, CF
3cF
2, CF
2hCF
2cH
2, CF
3cFHCF
2, CF
3cF
2cH
2, CF
3cF
2cF
2, HCF
2cF
2cF
2cH
2, CF
2hCF
2cF
2cF
2, (CH
2f)
2cH, (CF
3)
3c, CF
3cF
2cF
2cF
2, CF
3(CF
2cF
2)
2cF
2, HCF
2cF
2oCH
2cH
2cH
2, CF
3(CF
2cF
2)
3cF
2any one.
R
7for CH
3, CH
3cH
2, CH
3cH
2cH
2, (CH
3)
2cH, CH
3cH
2cH
2cH
2, CF
3, CF
3cH
2, CF
2hCH
2, CF
3cF
2, CF
2hCF
2cH
2, CF
3cFHCF
2, CF
3cF
2cH
2, CF
3cF
2cF
2, HCF
2cF
2cF
2cH
2, CF
2hCF
2cF
2cF
2, (CH
2f)
2cH, (CF
3)
3c, CF
3cF
2cF
2cF
2, CF
3(CF
2cF
2)
2cF
2, HCF
2cF
2oCH
2cH
2cH
2, CF
3(CF
2cF
2)
3cF
2any one.
Described electric conducting lithium salt also comprises LiBF
4, LiPF
6, LiPF
2o
2, LiAsF
6, LiClO
4, LiSO
3cF
3, LiB (C
2o
4)
2, LiBF
2c
2o
4, LiN (SO
2cF
3)
2, LiN (SO
2f)
2one or more.
Non-aqueous organic solvent is one or more in ethylene carbonate, propene carbonate, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, gamma-butyrolacton, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl propionate, propyl propionate, butyl propionate.
Described additive is vinylene carbonate, vinylethylene carbonate, fluorinated ethylene carbonate, difluorinated ethylene carbonate, PS, Isosorbide-5-Nitrae-butyl sultone, sulfuric acid vinyl ester, sulfuric acid propylene, one or more in ethylene sulfite, propylene sulfite.
A kind of lithium secondary battery: comprise positive plate, negative plate, barrier film and the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium of the present invention and become; Positive plate and negative plate comprise active material, conductive agent, collector, the bonding agent that described active material and conductive agent is combined with described collector.
Positive pole comprises reversibly can embed/the positive electrode active materials of deintercalate lithium ions, and positive electrode active materials is preferably the composite metal oxide of lithium, and metal oxide comprises the oxide of nickel, cobalt, manganese element and any ratio combination thereof; Positive electrode active materials also comprise in chemical element further one or several, described chemical element includes Mg, Al, Ti, Sn, V, Ge, Ga, B, Zr, Cr, Fe, Sr and rare earth element.Positive electrode active materials also comprises polyanion lithium compound LiM further
x(PO
4)
y(M is Ni, Co, Mn, Fe, Ti, V, 0≤x≤5,0≤y≤5).
Negative pole comprises the negative active core-shell material that can accept or discharge lithium ion, and described negative active core-shell material comprises lithium metal, lithium alloy, crystalline carbon, agraphitic carbon, carbon fiber, hard carbon, soft carbon; Wherein crystalline carbon comprises native graphite, graphitized coke, graphitization MCMB, graphitized intermediate-phase asphalt-based carbon fiber; Described lithium alloy comprises the alloy of lithium and aluminium, zinc, silicon, tin, gallium, antimony metal.
Compared with prior art, advantage of the present invention is:
(1) phosphonitrile oroalkane sulfonyl imine lithium provided by the invention has good thermal stability and hydrolytic resistance, possess high conductivity and oxidizing potential, and the electrode material of extensive use has good compatibility in conventional carbonate solution.
(2) with two (oroalkane sulfonyl) imines ([(R of bibliographical information
fsO
2)
2n]
-) anion compares, imines anion one end in formula (I) connects phosphazenium groups, phosphazenium groups has conjugated structure, after replacing the fluorine atom of phosphonitrile ring further by strong electron-withdrawing group group fluoro-alkyl, more effectively can reduce the cloud density of imines anion, promote the ionizing power of imines anion, thus the conductivity of raising imine lithium electrolyte, dissociation constant and transport number.Phosphazenium groups has significant flame-retarding characteristic in addition, is widely used at polymeric material field, in imine lithium structure, introduce phosphazenium groups, and make lithium-ion battery electrolytes have good security performance, this technology is most important in electrokinetic cell system.
Specific embodiment
The present invention is illustrated below by exemplary embodiment.Should be appreciated that scope of the present invention should not be limited to the scope of embodiment.Any do not depart from purport of the present invention change or change and can be understood by those skilled in the art.Protection scope of the present invention is determined by the scope of claims.
Embodiment 1
(1) preparation of electrolyte
(H in the glove box of argon atmosphere
2o<1ppm), be that EC (ethylene carbonate): DMC (dimethyl carbonate): EMC (methyl ethyl carbonate)=40: 40: 20 mixes with (five fluorine phosphonitriles) (trimethyl fluoride sulfonyl) imine lithium (1.0M) in mass ratio by organic solvent, add the VC (vinylene carbonate) of total weight 1%, the PS (propane sultone) of 2%, the FEC (fluorinated ethylene carbonate) of 3%, the SN (succinonitrile) of 3%.Above-mentioned each raw material is added successively, stirs, namely obtain lithium secondary cell electrolyte of the present invention (free acid <15ppm, moisture <10ppm).
(2) preparation of anode pole piece
By mass percent be 3% Kynoar (PVDF) be dissolved in 1-Methyl-2-Pyrrolidone solution, by the LiCoO of mass percent 94%
2add above-mentioned solution with the conductive agent carbon black of 3% and mix, after the slurry of mixed system being coated on the two sides of aluminium foil, after oven dry, roll extrusion, obtaining anode pole piece.Other positive electrode LiMn
2o
4, LiFePO
4, LiNi
0.5co
0.3mn
0.2, LiNi
0.3co
0.3mn
0.3prepare in the same way.
(3) preparation of cathode pole piece
It is the SBR binding agent of 4% by mass percent, mass percent is in the water-soluble solution of CMC thickener of 1%, is that the graphite of 95% adds above-mentioned solution, mixes mass percent, after the slurry of mixed system being coated on the two sides of Copper Foil, after oven dry, roll extrusion, obtain cathode pole piece.Other negative material Li
4ti
5o
12prepare by similar method.
(4) making of lithium ion battery
The anode pole piece of above-mentioned preparation, cathode pole piece and barrier film are made square electric cell with winding method, adopts polymer packaging, pour into the electrolyte of above-mentioned preparation, after the technique such as changing into, make the lithium ion battery that capacity is 1600mAh.
(5) battery performance test
Loop test condition: charge and discharge cycles test is carried out to battery with the multiplying power of 1/1C discharge and recharge, graphite/LiCoO
2electrode system: 3.0 ~ 4.35V; Graphite/LiFePO
4electrode system: 2.75 ~ 3.9V; Li
4ti
5o
12/ LiCoO
2electrode system: 1.0 ~ 2.6V; Li
4ti
5o
12/ LiFePO
4electrode system: 1.0 ~ 2.0V; Graphite/LiNi
0.5co
0.3mn
0.2electrode system: 3.0 ~ 4.35V; Graphite/LiMn
2o
4electrode system: 3.1 ~ 4.3V; Li
4ti
5o
12/ LiNi
0.5co
0.3mn
0.2electrode system: 1.0 ~ 2.6V.
High-temperature storage test condition: first will change into complete battery under normal temperature state with 1C discharge and recharge once, then carry out High temperature storage after battery being full of electricity with 1C, after battery cools completely, the battery of taking-up is carried out discharge test with 1C.
Embodiment 2 ~ 16 is except following table parameter, and other parameters and preparation method are with embodiment 1.
Table 1 embodiment 2 ~ 16 and comparative example 1-10
A kind of method preparing phosphonitrile oroalkane sulfonyl imine alkali metal salt disclosed by the invention, easy and simple to handle, products collection efficiency and purity are all very high, are suitable for suitability for industrialized production.Prepared carbonic ester electrolyte all possesses quite high purity, meets the application requirement in field of electronic devices.
As can be seen from the result of embodiment 2 ~ 14 and comparative example 1 ~ 10, when solvent is identical with additive component, use the battery of phosphonitrile oroalkane sulfonyl imine lithium than using LiPF
6cycle performance of battery and storge quality to get well.From embodiment 1,9, the result of embodiment 15,16 and comparative example 1,5 can be found out, phosphonitrile oroalkane sulfonyl imine lithium and LiPF
6compound uses as electric conducting lithium salt, and the cycle performance of respective battery and storge quality are also than being used alone LiPF
6battery more superior.As can be seen from the result of embodiment 12 ~ 14 and comparative example 8 ~ 10, when in electrolyte prescription, additive is less, the chemistry of lithium salts and the impact of electrochemical stability on battery performance more obvious.The difference of the battery performance that embodiment 2 ~ 14 and comparative example 1 ~ 10 embody, main cause is that phosphonitrile oroalkane sulfonyl imine lithium compares LiPF
6there is more stable chemical property, in cell operations, especially at high temperature can keep the stability of self chemistry, can not PF be produced
5deng lewis acid impurity, and affect the useful life of battery.
Claims (10)
1. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium, comprise electric conducting lithium salt, non-aqueous organic solvent and additive, electric conducting lithium salt comprises phosphonitrile oroalkane sulfonyl imine lithium, and phosphonitrile oroalkane sulfonyl imine lithium general structure is:
wherein, M
+li, R
1-5=-OR
7or-M [NSO
2-R
6]; R
6for carbon number be 1-8 containing fluoroalkyl, R
7for the alkanes group that carbon number is 1-10.
2. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, described R
1-5for identical or different structure.
3. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, described R
6for F, CF
3, CF
3cH
2, CF
2hCH
2, CF
3cF
2, CF
2hCF
2cH
2, CF
3cFHCF
2, CF
3cF
2cH
2, CF
3cF
2cF
2, HCF
2cF
2cF
2cH
2, CF
2hCF
2cF
2cF
2, (CH
2f)
2cH, (CF
3)
3c, CF
3cF
2cF
2cF
2, CF
3(CF
2cF
2)
2cF
2, HCF
2cF
2oCH
2cH
2cH
2, CF
3(CF
2cF
2)
3cF
2any one.
4. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, R
7for CH
3, CH
3cH
2, CH
3cH
2cH
2, (CH
3)
2cH, CH
3cH
2cH
2cH
2, CF
3, CF
3cH
2, CF
2hCH
2, CF
3cF
2, CF
2hCF
2cH
2, CF
3cFHCF
2, CF
3cF
2cH
2, CF
3cF
2cF
2, HCF
2cF
2cF
2cH
2, CF
2hCF
2cF
2cF
2, (CH
2f)
2cH, (CF
3)
3c, CF
3cF
2cF
2cF
2, CF
3(CF
2cF
2)
2cF
2, HCF
2cF
2oCH
2cH
2cH
2, CF
3(CF
2cF
2)
3cF
2any one.
5. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, described electric conducting lithium salt also comprises LiBF
4, LiPF
6, LiPF
2o
2, LiAsF
6, LiClO
4, LiSO
3cF
3, LiB (C
2o
4)
2, LiBF
2c
2o
4, LiN (SO
2cF
3)
2, LiN (SO
2f)
2one or more.
6. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, non-aqueous organic solvent is one or more in ethylene carbonate, propene carbonate, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, gamma-butyrolacton, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl propionate, propyl propionate, butyl propionate.
7. the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium according to claim 1, described additive is vinylene carbonate, vinylethylene carbonate, fluorinated ethylene carbonate, difluorinated ethylene carbonate, PS, 1,4-butyl sultone, sulfuric acid vinyl ester, sulfuric acid propylene, one or more in ethylene sulfite, propylene sulfite.
8. a lithium secondary battery: comprise positive plate, negative plate, barrier film and right and the electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium described in any one of 1-7 will be gone to become; Positive plate and negative plate comprise active material, conductive agent, collector, the bonding agent that described active material and conductive agent is combined with described collector.
9. lithium secondary battery according to claim 8, positive pole comprises reversibly can embed/the positive electrode active materials of deintercalate lithium ions, positive electrode active materials is preferably the composite metal oxide of lithium, and metal oxide comprises the oxide of nickel, cobalt, manganese element and any ratio combination thereof; Positive electrode active materials also comprise in chemical element further one or several, described chemical element includes Mg, Al, Ti, Sn, V, Ge, Ga, B, Zr, Cr, Fe, Sr and rare earth element.Positive electrode active materials also comprises polyanion lithium compound LiM further
x(PO
4)
y(M is Ni, Co, Mn, Fe, Ti, V, 0≤x≤5,0≤y≤5).
10. lithium secondary battery according to claim 8, negative pole comprises the negative active core-shell material that can accept or discharge lithium ion, and described negative active core-shell material comprises lithium metal, lithium alloy, crystalline carbon, agraphitic carbon, carbon fiber, hard carbon, soft carbon; Wherein crystalline carbon comprises native graphite, graphitized coke, graphitization MCMB, graphitized intermediate-phase asphalt-based carbon fiber; Described lithium alloy comprises the alloy of lithium and aluminium, zinc, silicon, tin, gallium, antimony metal.
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|---|---|---|---|
| CN201510454869.8A CN105206873B (en) | 2015-07-28 | 2015-07-28 | A kind of electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium and the battery using the electrolyte |
| PCT/CN2015/087310 WO2017015996A1 (en) | 2015-07-28 | 2015-08-18 | Phosphonitrile fluoroalkyl sulfimide alkali metal salt and electrolyte solution containing the metal salt |
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|---|---|---|---|
| CN201510454869.8A CN105206873B (en) | 2015-07-28 | 2015-07-28 | A kind of electrolyte containing phosphonitrile oroalkane sulfonyl imine lithium and the battery using the electrolyte |
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| CN105794837A (en) * | 2016-05-19 | 2016-07-27 | 东莞市瑞德丰生物科技有限公司 | Insecticidal composition containing phosphonitrile fluoroalkyl sulfimide alkali metal salt and diafenthiuron |
| CN105941472A (en) * | 2016-06-16 | 2016-09-21 | 东莞市瑞德丰生物科技有限公司 | Mollusk killing composition containing phosphonitrile fluoroalkyl sulfimide alkali metal salt and niclosamide |
| CN105961427A (en) * | 2016-06-01 | 2016-09-28 | 东莞市瑞德丰生物科技有限公司 | Acaricidal composition containing phosphazene fluoroalkyl sulfimide alkali metal salt and abamectin |
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| CN109467572B (en) * | 2018-11-15 | 2021-04-09 | 合肥国轩高科动力能源有限公司 | A 3,5-diphosphazene p-phenylene diether additive and lithium ion battery electrolyte containing the additive |
| CN111740166A (en) * | 2020-07-06 | 2020-10-02 | 香河昆仑化学制品有限公司 | Electrolyte containing bis (trifluorophosphoalkyl) imide salt and lithium ion battery |
| CN111740166B (en) * | 2020-07-06 | 2023-03-24 | 香河昆仑新能源材料股份有限公司 | Electrolyte containing bis (trifluorophosphoalkyl) imide salt and lithium ion battery |
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