CN107004899A - 作为锂离子电池的电解液组分的环状膦酰胺 - Google Patents
作为锂离子电池的电解液组分的环状膦酰胺 Download PDFInfo
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- CN107004899A CN107004899A CN201680003856.1A CN201680003856A CN107004899A CN 107004899 A CN107004899 A CN 107004899A CN 201680003856 A CN201680003856 A CN 201680003856A CN 107004899 A CN107004899 A CN 107004899A
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- 239000003792 electrolyte Substances 0.000 title claims abstract description 35
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 17
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 10
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical class O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims abstract description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 230000004888 barrier function Effects 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- 229910001290 LiPF6 Inorganic materials 0.000 claims description 4
- 150000005677 organic carbonates Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910013098 LiBF2 Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 claims description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- -1 cyclic phosphines Acid amides Chemical class 0.000 description 15
- 239000000654 additive Substances 0.000 description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 6
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000004087 circulation Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920001410 Microfiber Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910021437 lithium-transition metal oxide Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000003658 microfiber Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000319 transition metal phosphate Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-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
- 125000006091 1,3-dioxolane group Chemical class 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910003321 CoFe Inorganic materials 0.000 description 1
- 229910002441 CoNi Inorganic materials 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910004259 Li(NiMn)O2 Inorganic materials 0.000 description 1
- 229910032387 LiCoO2 Inorganic materials 0.000 description 1
- 229910011279 LiCoPO4 Inorganic materials 0.000 description 1
- 229910002993 LiMnO2 Inorganic materials 0.000 description 1
- 229910003005 LiNiO2 Inorganic materials 0.000 description 1
- 229910013084 LiNiPO4 Inorganic materials 0.000 description 1
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- KFDQGLPGKXUTMZ-UHFFFAOYSA-N [Mn].[Co].[Ni] Chemical compound [Mn].[Co].[Ni] KFDQGLPGKXUTMZ-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
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/04—Hybrid capacitors
- H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/64—Liquid electrolytes characterised by 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
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Abstract
本发明涉及电解液，其包含100重量份非质子溶剂、1至50重量份含锂的导电性盐、4至50重量份碳酸亚乙烯酯，及通式1的环状膦酰胺其中R1、R2、R3各自是未经取代或被氟、氯或甲硅烷基取代的、具有1至20个碳原子的烃基，其中基团R1、R2、R3中的两个或三个可以彼此连接，及n具有0、1、2、3、4或5的值；本发明还涉及包含正极、负极、隔膜和电解液的锂离子电池。
Description
技术领域
本发明涉及电解液，其包含非质子溶剂、含锂的导电性盐、碳酸亚乙烯酯及环状膦酰胺，本发明还涉及锂离子电池。
背景技术
锂离子电池属于最有前景的移动应用系统。应用领域由高级电子设备延伸至电驱动的汽车的电池。
已经广泛地描述了用于锂离子电池的基于环状/脂族碳酸酯的电解液原液，其作为主要组分形成大多数电解液基础组合物的基础。碳酸亚乙烯酯(VC)应当作为形成薄膜的添加剂支持“固体电解质界面”(SEI)的形成，典型地通常以2至10重量％的量添加。US 7,476,469针对由薄的非晶/微晶硅层组成的负极材料也描述了具有更高的VC比例的原液。
WO 15078789描述了甲硅烷基化的环状膦酰胺及其在锂离子电池中作为电解液混合物的添加剂的用途。
由于含Si的负极材料在循环期间严重的体积膨胀，含有含Si的负极材料的锂离子电池的循环稳定性仍然不足。在初始循环中由于单种电解液成分发生电化学分解而形成的SEI层无法经受住强烈的机械负载。持续地重新形成SEI层，导致单种电解液成分发生贫化/消耗，由此导致电池容量随着循环次数的增加而持续地减小。
发明内容
本发明涉及电解液，其包含
100重量份非质子溶剂，
1至50重量份含锂的导电性盐，
4至50重量份碳酸亚乙烯酯，及
通式1的环状膦酰胺
其中
R1、R2、R3各自是未经取代或被氟、氯或甲硅烷基取代的、具有1至20个碳原子的烃基，其中基团R1、R2、R3中的两个或三个可以彼此连接，及
n具有0、1、2、3、4或5的值。
出人意料地发现，通过在富含VC的电解液原液中使用通式1的膦酰胺作为添加剂，可以显著地改善锂离子电池在循环期间的容量保持率。持续的容量保持率甚至优于所选的参考电解液混合物，其是从由文献公开的用于含Si负极的电解液组合物出发的[Kawashima,A.et al.,Journal of The Electrochemical Society 2011,158,A798-A801；Aurbach,D.et al.,Langmuir 2012,28,965-976]。参考电解液混合物由碳酸甲乙酯(EMC)和氟代碳酸亚乙酯(FEC)以及小比例的VC组成。
基团R1、R2、R3的例子是烷基，如甲基、乙基、正丙基、异丙基、1–正丁基、2–正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基；己基，如正己基；庚基，如正庚基；辛基，如正辛基、异辛基及2,2,4–三甲基戊基；壬基，如正壬基；癸基，如正癸基；十二烷基，如正十二烷基；十八烷基，如正十八烷基；环烷基，如环戊基、环己基、环庚基及甲基环己基；烯基，如乙烯基、1–丙烯基及2–丙烯基；芳基，如苯基、萘基、蒽基及菲基；烷芳基，如邻–、间–及对甲苯基；二甲苯基及乙基苯基；及芳烷基，如苯甲基、α–和β–苯基乙基。
经取代的基团R1、R2和R3的例子是三氟甲基、3,3,3–三氟正丙基、2,2,2,2′,2′,2′–六氟异丙基、5,5,5,4,4,3,3–七氟戊基和七氟异丙基；及卤代芳基，如邻–、间–及对氯苯基；及在烷基中具有1至6个碳原子的三甲基甲硅烷基烷基，尤其是三甲基甲硅烷基甲基。
优选的烃基R1具有1至10个碳原子。特别优选为具有1至6个碳原子的烷基及具有2至6个碳原子的烯基。R1、R2和R3各自特别优选为甲基、乙基、正丙基、异丙基及乙烯基。
若基团R1、R2和R3中的两个或三个彼此连接，则它们可以形成单环或双环的烃环。
n优选具有0或1的值。
特别优选为N,N′–双(三甲基甲硅烷基甲基)–N,N′–三亚甲基甲基膦酰二胺。
WO 15078789公开了通式1的环状膦酰胺的制备方法。
所述电解液优选包含0.1至10重量份、更优选0.5至5重量份、特别优选1至3重量份的通式1的环状膦酰胺。
所述非质子溶剂优选选自：有机碳酸酯，如碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸亚乙酯、碳酸亚乙烯酯、碳酸亚丙酯、碳酸亚丁酯；环状和线性的酯，如乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酸丙酯、丁酸乙酯、异丁酸乙酯；环状和线性的醚，如2–甲基四氢呋喃、1,2–二乙氧基甲烷、THF、二噁烷、1,3–二氧戊环、二异丙基醚、二乙二醇二甲醚；酮，如环戊酮、二异丙基酮、甲基异丁基酮；内酯，如γ–丁内酯；环丁砜、二甲基亚砜、甲酰胺、二甲基甲酰胺、3–甲基–1,3–噁唑烷–2–酮及这些溶剂的混合物。
特别优选为上述的有机碳酸酯。
所述电解液包含优选5至40重量份、更优选10至20重量份的含锂的导电性盐。
所述含锂的导电性盐优选选自：LiPF6、LiBF4、LiClO4、LiAsF6、(LiB(C2O4)2、LiBF2(C2O4))、LiSO3CxF2x+1、LiN(SO2CxF2x+1)2及LiC(SO2CxF2x+1)3及其混合物，其中x取值为0至8的整数。
例如在DE 100 27 626 A中所述，该电解液还可以包含其他添加剂，如用于降低水含量的有机异氰酸酯、HF清除剂、LiF的增溶剂、有机锂盐和/或络盐。
本发明还涉及锂离子电池，其包含正极、负极、隔膜及上述的电解液。
锂离子电池的负电极(负极)优选包含能够可逆地接收及再次脱出锂离子的材料，例如金属锂、碳如炭黑或石墨、硅、锡、铝或铅，优选为石墨和/或硅。锂离子电池的正电极(正极)优选包含锂过渡金属氧化物或锂过渡金属磷酸盐。优选的过渡金属是Ti、V、Cr、Mn、Co、Fe、Ni、Mo、W。优选的锂过渡金属氧化物是LiCoO2、LiNiO2、LiMnO2、LiMn2O4、Li(CoNi)O2、Li(CoV)O2、Li(CoFe)O2。优选的锂过渡金属磷酸盐是LiCoPO4、Li(NiMn)O2和LiNiPO4。锂离子电池的电极还可以包含其他例如提高导电性的添加剂、粘合剂、分散剂和填料。可以使用其他在EP 785 586A中所述的添加剂。
本发明还涉及上述的电解液在锂离子电池中的用途。
上述式的所有上述符号的定义均彼此独立。在所有的式中，硅原子均为四价。
在以下实施例中，除非各自另有说明，所有的量和百分比数据均是基于重量，所有压力均为0.10MPa(绝对)，所有温度均为20℃。
实施例：
1、包含碳酸甲乙酯(EMC)和氟代碳酸亚乙酯(FEC)的参考电解液混合物(非本发明)
从由文献公开的电解液组合物出发[Kawashima,A.et al.,Journal of TheElectrochemical Society 2011,158,A798-A801；Aurbach,D.et al.,Langmuir 2012,28,965-976]，类似地制备FEC/EMC的体积比为30:70的混合物。将2重量％碳酸亚乙烯酯和1MLiPF6溶解在该混合物中。
2、包含N,N′–双(三甲基甲硅烷基甲基)–N,N′–三亚甲基甲基膦酰二胺(cyPPA)的电解液混合物
制备碳酸亚乙烯酯/碳酸甲乙酯的体积比为12:88的混合物。
将2重量％的cyPPA和1M LiPF6溶解在该混合物中。
所用的电极和电池组装：
将来自实施例1、2和3的电解液混合物与Si/石墨负极和NMC(镍锰钴)组装全电池(CR2032型)。电解液的量恒定地为80μl。将GF D型玻璃微纤维过滤器(Type D GlassMicrofiber Filters，Whatman)用作隔膜。所用的负极由20％硅(平均粒径约为180nm的未聚集的颗粒)、60％石墨(SFG 6)、8％粘合剂(CMC 1380)和12％导电炭黑(Super P)组成。所用的正极是由94％NMC111、2％粘合剂和4％导电材料组成的标准材料。所用的正极与负极的容量比为2.0/2.1mAh/cm2。组装的电池均测量其在首次循环中的放电容量C1及其在100次循环后的容量保持率(保持率C100)及其在300次循环后的容量保持率(保持率C300)。结果列于表1。
装置和测量方法：
在BaSyTeC CTS-实验室电池测试系统(Lab Battery Test System)的试验台上对全电池–钮扣电池实施电化学测试。电池首先在4.2至3.0V的电压窗口中在两个循环中以C/10及各自随后以CV步骤进行化成(4.2V至3V，C/10，cccv(cv步骤至I<0.01CA))。随后在相同的电压窗口中以C/2及各自随后以CV步骤进行300次循环(4.2V至3V，C/2，cccv(cv步骤至I<0.125CA))。
表1：
由表1中的容量保持率可以看出通式1的环状膦酰胺的效果：相对于参考电解液混合物(参见实施例1)，在100次循环后改善了约17％，及在300次循环后改善了约22％。
通过电池在首次循环中近似相等的放电容量C1证明包含电解液混合物1和2的电池中电极的初始状态相同(充电，平衡)。
Claims (10)
1.电解液，其包含
100重量份非质子溶剂，
1至50重量份含锂的导电性盐，
4至50重量份碳酸亚乙烯酯，及
通式1的环状膦酰胺
其中
R1、R2、R3各自是未经取代或被氟、氯或甲硅烷基取代的、具有1至20个碳原子的烃基，其中基团R1、R2、R3中的两个或三个可以彼此连接，及
n具有0、1、2、3、4或5的值。
2.根据权利要求1的电解液，其中R2和R3选自在烷基中具有1至6个碳原子的三甲基甲硅烷基烷基。
3.根据前述权利要求之一的电解液，其中R1是具有1至6个碳原子的烷基。
4.根据前述权利要求之一的电解液，其中n具有1的值。
5.根据前述权利要求之一的电解液，其中所述电解液包含0.1至10重量份通式1的环状膦酰胺。
6.根据前述权利要求之一的电解液，其中所述非质子溶剂选自：有机碳酸酯、环状和线性的酯、环状和线性的醚、酮、内酯、环丁砜、二甲基亚砜、甲酰胺、二甲基甲酰胺、3–甲基–1,3–噁唑烷–2–酮及这些溶剂的混合物。
7.根据前述权利要求之一的电解液，其中所述含锂的导电性盐选自：LiPF6、LiBF4、LiClO4、LiAsF6、LiSO3CxF2x+1、(LiB(C2O4)2、LiBF2(C2O4))、LiN(SO2CxF2x+1)2及LiC(SO2CxF2x+1)3及其混合物，其中x取值为0至8的整数。
8.根据前述权利要求之一的电解液，其包含0.1至10重量％的通式1的环状膦酰胺。
9.锂离子电池，其包含正极、负极、隔膜和根据前述权利要求之一的电解液。
10.根据权利要求9的锂离子电池，其包含含硅的负极。
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| PCT/EP2016/071165 WO2017055049A1 (de) | 2015-09-28 | 2016-09-08 | Cyclische phosphonamide als elektrolytbestandteil für lithium-ionen-batterien |
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| CN101461088B (zh) * | 2006-05-31 | 2011-12-21 | 三洋电机株式会社 | 高电压充电型非水电解质二次电池 |
| WO2012115119A1 (ja) * | 2011-02-22 | 2012-08-30 | 三菱化学株式会社 | 非水系電解液、及びそれを用いた電池 |
| US9472829B2 (en) | 2012-06-15 | 2016-10-18 | Tosoh F-Tech, Inc. | Method for stabilizing LiPF6, electrolyte solution for nonaqueous secondary batteries having excellent thermal stability, and nonaqueous secondary battery having excellent thermal stability |
| JP2015026589A (ja) * | 2013-07-29 | 2015-02-05 | 富士フイルム株式会社 | 非水二次電池用電解液および非水二次電池 |
-
2015
- 2015-09-28 DE DE102015218653.9A patent/DE102015218653A1/de not_active Withdrawn
-
2016
- 2016-09-08 EP EP16762817.1A patent/EP3201981B1/de not_active Not-in-force
- 2016-09-08 US US15/527,126 patent/US10128539B2/en not_active Expired - Fee Related
- 2016-09-08 JP JP2017528468A patent/JP2018501611A/ja active Pending
- 2016-09-08 KR KR1020197001238A patent/KR20190007111A/ko active Application Filing
- 2016-09-08 CN CN201680003856.1A patent/CN107004899A/zh not_active Withdrawn
- 2016-09-08 WO PCT/EP2016/071165 patent/WO2017055049A1/de active Application Filing
- 2016-09-08 KR KR1020177014108A patent/KR20170073683A/ko active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1486519A (zh) * | 2001-01-18 | 2004-03-31 | ������������ʽ���� | 二次锂电池 |
| CN1841833A (zh) * | 2005-03-31 | 2006-10-04 | 三洋电机株式会社 | 非水电解液二次电池 |
| JP2014063733A (ja) * | 2012-09-03 | 2014-04-10 | Mitsubishi Chemicals Corp | 非水系電解液及びそれを用いた非水系電解液電池 |
| US20140137400A1 (en) * | 2012-11-16 | 2014-05-22 | Quan An Resource Co., Ltd. | Method of producing silicon material, anode material and method of producing anode electrode of lithium-ion battery |
| WO2015078789A1 (de) * | 2013-11-26 | 2015-06-04 | Wacker Chemie Ag | Silylierte cyclische phosphonamide |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102015218653A1 (de) | 2017-03-30 |
| EP3201981A1 (de) | 2017-08-09 |
| KR20170073683A (ko) | 2017-06-28 |
| KR20190007111A (ko) | 2019-01-21 |
| JP2018501611A (ja) | 2018-01-18 |
| US20170365879A1 (en) | 2017-12-21 |
| EP3201981B1 (de) | 2018-08-08 |
| US10128539B2 (en) | 2018-11-13 |
| WO2017055049A1 (de) | 2017-04-06 |
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