JP6542209B2 - リチウムイオン電池用電解質における電解質添加剤としての反応性リチウムアルコキシボレートの使用 - Google Patents
リチウムイオン電池用電解質における電解質添加剤としての反応性リチウムアルコキシボレートの使用 Download PDFInfo
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- JP6542209B2 JP6542209B2 JP2016526553A JP2016526553A JP6542209B2 JP 6542209 B2 JP6542209 B2 JP 6542209B2 JP 2016526553 A JP2016526553 A JP 2016526553A JP 2016526553 A JP2016526553 A JP 2016526553A JP 6542209 B2 JP6542209 B2 JP 6542209B2
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- Prior art keywords
- lithium
- cyclic
- alkyl
- electrolyte composition
- formula
- 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.)
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- 239000003792 electrolyte Substances 0.000 title claims description 70
- 229910001416 lithium ion Inorganic materials 0.000 title claims description 56
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims description 55
- 229910052744 lithium Inorganic materials 0.000 title claims description 32
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims description 28
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000002000 Electrolyte additive Substances 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 title 1
- -1 lithium phenyltrimethylborate Chemical compound 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 68
- 125000004122 cyclic group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052710 silicon Chemical group 0.000 claims description 18
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 17
- 239000006183 anode active material Substances 0.000 claims description 17
- 239000011572 manganese Substances 0.000 claims description 17
- 239000010703 silicon Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 239000006182 cathode active material Substances 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910000314 transition metal oxide Inorganic materials 0.000 claims description 11
- 229910052718 tin Inorganic materials 0.000 claims description 10
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 10
- 229910011281 LiCoPO 4 Inorganic materials 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 125000002015 acyclic group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 229910010707 LiFePO 4 Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 229910052596 spinel Inorganic materials 0.000 claims description 6
- 239000011029 spinel Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 150000000185 1,3-diols Chemical class 0.000 claims description 4
- 229910015015 LiAsF 6 Inorganic materials 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 150000005215 alkyl ethers Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 4
- 150000001924 cycloalkanes Chemical class 0.000 claims description 4
- YNQRWVCLAIUHHI-UHFFFAOYSA-L dilithium;oxalate Chemical compound [Li+].[Li+].[O-]C(=O)C([O-])=O YNQRWVCLAIUHHI-UHFFFAOYSA-L 0.000 claims description 4
- 239000010450 olivine Substances 0.000 claims description 4
- 229910052609 olivine Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 150000008053 sultones Chemical class 0.000 claims description 4
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 3
- 229910010238 LiAlCl 4 Inorganic materials 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000002895 organic esters Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 229910000319 transition metal phosphate Inorganic materials 0.000 claims description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-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
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- YNTQEBRPIHZREE-UHFFFAOYSA-N B(OC)(OC)OC.COCCO.[Li] Chemical compound B(OC)(OC)OC.COCCO.[Li] YNTQEBRPIHZREE-UHFFFAOYSA-N 0.000 claims description 2
- GRRMYECKOTXRPF-UHFFFAOYSA-N B(OC)(OC)OC.COCCOCCO.[Li] Chemical compound B(OC)(OC)OC.COCCOCCO.[Li] GRRMYECKOTXRPF-UHFFFAOYSA-N 0.000 claims description 2
- ACWZNJOXJZOMHY-UHFFFAOYSA-N B(OC)(OC)OC.OCC1OC(OC1)=O.[Li] Chemical compound B(OC)(OC)OC.OCC1OC(OC1)=O.[Li] ACWZNJOXJZOMHY-UHFFFAOYSA-N 0.000 claims description 2
- 229910013684 LiClO 4 Inorganic materials 0.000 claims description 2
- 229910012513 LiSbF 6 Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Chemical group 0.000 claims description 2
- 239000011574 phosphorus Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 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 claims 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 19
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 15
- 239000011135 tin Substances 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 9
- 239000000956 alloy Substances 0.000 description 9
- 239000011888 foil Substances 0.000 description 9
- 229910003002 lithium salt Inorganic materials 0.000 description 9
- 159000000002 lithium salts Chemical class 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- 229910013870 LiPF 6 Inorganic materials 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 229910002804 graphite Inorganic materials 0.000 description 7
- 239000010439 graphite Substances 0.000 description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 6
- 229910013063 LiBF 4 Inorganic materials 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 229920001515 polyalkylene glycol Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- 229910018344 Ni0.22Co0.12Mn0.66 Inorganic materials 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000002931 mesocarbon microbead Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- DSMUTQTWFHVVGQ-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1F DSMUTQTWFHVVGQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910000733 Li alloy Inorganic materials 0.000 description 2
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 2
- 229910014689 LiMnO Inorganic materials 0.000 description 2
- 229910013290 LiNiO 2 Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910018353 Ni0.21Co0.08Mn0.71 Inorganic materials 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
(i)少なくとも1種の非プロトン性有機溶剤、
(ii)少なくとも1種の式(I)の化合物とは異なる少なくとも1種の導電性塩、
(iii)少なくとも1種の式(I)の化合物
R1、R2、R3及びR4は、相互に独立して、C1−C10アルキル、C2−C10アルケニル、C2−C10アルキニル、C3−C10シクロアルキル、C6−C14アリール及び C5−C14ヘテロアリールから選択され、且つこれらのアルキル、アルケニル、アルキニル、シクロアルキル、アリール及びヘテロアリールは、F、CN、OR5、
R4はR1、R2及びR3のそれぞれと異なり、
R5は、H、2〜10個のアルキレンオキシド単位を有するオリゴC1−C4アルキレンオキシド、及びC1−C4アルキル、C2−C4アルケニル、C2−C4アルキニル、フェニル、ベンジル及びC(O)OC1−C10アルキルから選択される任意にフッ素化された基から選択され、
R6はH、F及び任意にフッ素化されたC1−C4アルキルから選択される。]、及び
(iv)任意に、少なくとも1種のさらなる添加剤
を含む電解質組成物(A)、によって達成される。
少なくとも1種の式(I)の化合物を含む本発明の電解質組成物は、導電性リチウム塩のみ含む電解質組成物に比較して、55℃でのサイクル試験(cycling)後の放電容量の保持力を改良している。
(a)部分的にハロゲン化されていても良い、環状又は非環状の有機カーボネート、
(b)部分的にハロゲン化されていても良い、ジ−C1−C10アルキルエーテル、
(c)部分的にハロゲン化されていても良い、ジ−C1−C4アルキル−C2−C6アルキレンエーテル及びポリエーテル、
(d)部分的にハロゲン化されていても良い、環状エーテル、
(e)部分的にハロゲン化されていても良い、環状又は非環状のアセタール及びケタール、
(f)部分的にハロゲン化されていても良い、オルトカルボン酸エステル、
(g)部分的にハロゲン化されていても良い、環状又は非環状のカルボン酸エステル、
(h)部分的にハロゲン化されていても良い、環状又は非環状のスルホン、
(i)部分的にハロゲン化されていても良い、環状又は非環状のニトリル及びジニトリル、及び
(j)部分的にハロゲン化されていても良い、イオン液体
から選択されることが好ましい。
好適な有機カーボネート(a)の例としては、一般式(a1)、(a2)又は(a3)に従う環状有機カーボネートを挙げることができる:
Li[F6−xP(CyF2y+1)x](但し、xは0〜6の範囲の整数であり、yは1〜20の範囲の整数である。);
Li[B(R10)4]、Li[B(R10)2(OR11O)]及びLi[B(OR11O)2]
[但し、それぞれのR10は、相互に独立して、F、Cl、Br、I、C1−C4アルキル、C2−C4アルケニル及びC2−C4アルキニルから選択され、且つこれらのアルキル、アルケニル及びアルキニルは、1個以上のOR12(但しR12はC1−C6アルキル、C2−C6アルケニル及びC2−C6アルキニルから選択される)で置換されていても良く、そして
(OR11O)は、1,2−又は1,3−ジオール、1,2−又は1,3−ジカルボン酸、1,2−又は1,3−ヒドロキシカルボン酸から誘導される2価の基であり、且つこの2価の基は、中心B原子と共に両方の酸素を介して5−又は6−員環を形成する];
一般式Li[X(CnF2n+1SO2)m]の塩
[但し、Xが酸素及びイオウから選択される場合m=1、
Xが窒素及びリンから選択される場合m=2、
Xが炭素及びケイ素から選択される場合m=3であり、
nが1〜20の範囲の整数である。];
LiClO4;LiAsF6;LiCF3SO3;Li2SiF6;LiSbF6;LiAlCl4;Li[N(SO2F)2];リチウムテトラフルオロ(オキサラト)ホスフェート;及びリチウムオキサレート
から選択されることが好ましい。
(i)60〜99.98質量%の少なくとも1種の非プロトン性有機溶剤、
(ii)0.01〜25質量%の、少なくとも1種の式(I)の化合物とは異なる少なくとも1種の導電性塩、
(iii)0.01〜25質量%の式(I)の少なくとも1種の化合物、及び
(iv)0〜10質量%の少なくとも1種のさらなる添加剤、
を含み、これらの質量%は電解質組成物の総質量に基づくものである、電解質組成物であることがさらに好ましい。
(A)上記で詳述された電解質組成物、
(B)カソード活性材料を含む、少なくとも1種のカソード、及び
(C)アノード活性材料を含む、少なくとも1種のアノード
を含むリチウムイオン電池である。
その製造と後処理はグローブボックスにおいてN2下で行った。
コインセルを、Pred Materials (USA)製の2032タイプコインセルの部品を用いて組み立てた。2032タイプコインセルの部品は、SUS304Al−被覆ケース、SUS316Lキャップ、PPガスケット、15.5mmの直径及び1.0mmの厚さのディスクスペーサ、及び15mmの直径及び1.4mmの厚さの波型バネを含む。セルを、Arを満たしたグローブボックス内の各セルにおいて、カソード活性材料LiNi0.5Mn1.5O4 (d = 14.7 mm)及びグラファイトアノード(d = 15.0 mm)、1片のSetela E20MMポリオレフィンセパレータ(d = 19 mm)及び40μL(20μL×2)の電解質を用いて構築した。水含有量は0.1ppm未満である。電池グレードのカーボネート溶剤及びリチウムヘキサフルオロホスフェート(LiPF6)をNovolyteから入手した。比較の電解質組成物は、1.0 M のLiPF6のEC/EMC (3:7体積比)溶液であった。本発明の電解質組成物は、電解質組成物の総質量に対して1質量%の式(I)の化合物の濃度となるように、式(I)の化合物を比較の電解質組成物に加えることにより作製した。
Claims (14)
- (i)少なくとも1種の非プロトン性有機溶剤、
(ii)少なくとも1種の式(I)の化合物とは異なる少なくとも1種の導電性塩、
(iii)少なくとも1種の式(I)の化合物
R1、R2、及びR 3 は、任意にフッ素化されたC 1 −C 6 アルキルであり、
R 4 は、C1−C 6 アルキル、C2−C 6 アルケニル、C2−C 6 アルキニル、C6−C14アリール及びC5−C14ヘテロアリールから選択され、且つこれらのアルキル、アルケニル、アルキニル、アリール及びヘテロアリールは、F、CN、及びOR5
から選択される1個以上の置換基で置換されていても良く、
R4はR1、R2及びR3のそれぞれと異なり、
R5は、2〜10個のアルキレンオキシド単位を有するオリゴC1−C4アルキレンオキシドから選択される。]、及び
(iv)任意に、少なくとも1種のさらなる添加剤
を含む電解質組成物(A)。 - 少なくとも1種の式(I)の化合物が、
R1、R2、及びR3がCH3である式(I)の化合物から選択される、請求項1に記載の電解質組成物。 - 少なくとも1種の式(I)の化合物が、
R1、R2、及びR3がCH3であり、
R4は、C2−C4アルキル、C2−C4アルケニル、C2−C4アルキニル、C3−C6シクロアルキル、C6アリール及び C5−C7ヘテロアリールから選択され、且つこれらのアルキル、アルケニル、アルキニル、シクロアルキル、アリール及びヘテロアリールは、F、CN、OR5、
R5は、H、2〜10個のアルキレンオキシド単位を有するオリゴC2−C3アルキレンオキシド、及びC1−C4アルキル、フェニル、ベンジル及びC(O)OC1−C4アルキルから選択される任意にフッ素化された基から選択され、
R6はH、F及び任意にフッ素化されたC1−C4アルキルから選択される場合の式(I)の化合物から選択される、請求項1または2に記載の電解質組成物。 - 少なくとも1種の式(I)の化合物が、
リチウム3−アリルトリメチルボレート、リチウム3−プロパルギルトリメチルボレート、リチウムフェニルトリメチルボレート、リチウム4−ピリジルトリメチルボレート、リチウム3−ピリジルトリメチルボレート、リチウム2−ピリジルトリメチルボレート、リチウム2,2,2−トリフルオロエチルトリメチルボレート、リチウムグリセロールカーボネートトリメチルボレート、リチウムエチレングリコールメチルエーテルトリメチルボレート、リチウムジエチレングリコールメチルエーテルトリメチルボレート、リチウム4−フルオロフェニルトリメチルボレート、リチウム2−ブチニルトリメチルボレート、リチウム3−プロピオニトリルトリメチルボレート、及びリチウムトリフルオロエチルトリメチルボレートから選択される請求項1〜3のいずれか1項に記載の電解質組成物。 - 少なくとも1種の非プロトン性有機溶剤(i)が、
(a)部分的にハロゲン化されていても良い、環状又は非環状の有機カーボネート、
(b)部分的にハロゲン化されていても良い、ジ−C1−C10アルキルエーテル、
(c)部分的にハロゲン化されていても良い、ジ−C1−C4アルキル−C2−C6アルキレンエーテル及びポリエーテル、
(d)部分的にハロゲン化されていても良い、環状エーテル、
(e)部分的にハロゲン化されていても良い、環状又は非環状のアセタール及びケタール、
(f)部分的にハロゲン化されていても良い、オルトカルボン酸エステル、
(g)部分的にハロゲン化されていても良い、環状又は非環状のカルボン酸エステル、
(h)部分的にハロゲン化されていても良い、環状又は非環状のスルホン、
(i)部分的にハロゲン化されていても良い、環状又は非環状のニトリル及びジニトリル、及び
(j)部分的にハロゲン化されていても良い、イオン液体
から選択される請求項1〜4のいずれか1項に記載の電解質組成物。 - 電解質組成物が、少なくとも1種の式(I)の化合物とは異なる少なくとも1種の導電性塩(ii)を含み、該少なくとも1種の導電性塩(ii)は、
Li[F6−xP(CyF2y+1)x](但し、xは0〜6の範囲の整数であり、yは1〜20の範囲の整数である。);
Li[B(R10)4]、Li[B(R10)2(OR11O)]及びLi[B(OR11O)2]
[但し、それぞれのR10は、相互に独立して、F、Cl、Br、I、C1−C4アルキル、C2−C4アルケニル及びC2−C4アルキニルから選択され、且つこれらのアルキル、アルケニル及びアルキニルは、1個以上のOR12(但しR12はC1−C6アルキル、C2−C6アルケニル及びC2−C6アルキニルから選択される)で置換されていても良く、そして
(OR11O)は、1,2−又は1,3−ジオール、1,2−又は1,3−ジカルボン酸、1,2−又は1,3−ヒドロキシカルボン酸から誘導される2価の基であり、且つこの2価の基は、中心B原子と共に両方の酸素を介して5−又は6−員環を形成する];
一般式Li[X(CnF2n+1SO2)m]の塩
[但し、Xが酸素及びイオウから選択される場合m=1、
Xが窒素及びリンから選択される場合m=2、
Xが炭素及びケイ素から選択される場合m=3であり、
nが1〜20の範囲の整数である。];
LiClO4;LiAsF6;LiCF3SO3;Li2SiF6;LiSbF6;LiAlCl4;Li[N(SO2F)2];リチウムテトラフルオロ(オキサラト)ホスフェート;及びリチウムオキサレート
から選択される請求項1〜5のいずれか1項に記載の電解質組成物。 - 電解質組成物が、少なくとも1種のさらなる添加剤(iv)を含み、該少なくとも1種の添加剤(iv)は、ビニレンカーボネート及びその誘導体、ビニルエチレンカーボネート及びその誘導体、メチルエチレンカーボネート及びその誘導体、リチウム(ビスオキサラト)ボレート、リチウムジフルオロ(オキサラト)ボレート、リチウムテトラフルオロ(オキサラト)ホスフェート、リチウムオキサレート、2−ビニルピリジン、4−ビニルピリジン、環状エキソ−メチレンカーボネート、スルトン、環状及び非環状スルホネート、環状及び非環状スルフィット、環状及び非環状スルフィネート、無機酸の有機エステル、1バールで少なくとも36℃の沸点を有する非環状及び環状のアルカン、芳香族化合物、任意にハロゲン化された環状及び非環状のスルホニルイミド、任意にハロゲン化された環状及び非環状のホスフェートエステル、任意にハロゲン化された環状及び非環状のホスフィン、任意にハロゲン化された環状及び非環状のホスフィット、任意にハロゲン化された環状及び非環状のホスファゼン、任意にハロゲン化された環状及び非環状のシリルアミン、任意にハロゲン化された環状及び非環状のハロゲン化エステル、任意にハロゲン化された環状及び非環状のアミド、任意にハロゲン化された環状及び非環状の無水物、任意にハロゲン化されたヘテロ環から選択される請求項1〜6のいずれか1項に記載の電解質組成物。
- 電解質組成物が、
(i)60〜99.98質量%の少なくとも1種の非プロトン性有機溶剤、
(ii)0.01〜25質量%の、少なくとも1種の式(I)の化合物とは異なる少なくとも1種の導電性塩、
(iii)0.01〜25質量%の少なくとも1種の式(I)の化合物、及び
(iv)0〜10質量%の少なくとも1種のさらなる添加剤、
を含み、これらの質量%は電解質組成物の総質量に基づくものである請求項1〜7のいずれか1項に記載の電解質組成物。 - 請求項1〜8のいずれか1項に記載の式(I)の化合物の、リチウムイオン電池の電解質組成物用添加剤としての使用。
- (A)請求項1〜8のいずれか1項に記載の電解質組成物、
(B)カソード活性材料を含む、少なくとも1種のカソード、及び
(C)アノード活性材料を含む、少なくとも1種のアノード
を含むリチウムイオン電池。 - アノード活性材料が、リチウムイオンを可逆的に吸蔵及び放出することができるカーボンを含む請求項10に記載のリチウムイオン電池。
- アノード活性材料が、ケイ素又はスズを含む請求項10に記載のリチウムイオン電池。
- 少なくとも1種のカソード活性材料が、
オリビン構造のリチウム化遷移金属ホスフェート、層構造を有するリチウムイオン挿入遷移金属酸化物、及びスピネル構造のリチウム化遷移金属混合酸化物、から選択されるリチウムイオンを吸蔵及び放出することができる材料を含む請求項10〜12のいずれか1項に記載のリチウムイオン電池。 - 少なくとも1種のカソード活性材料が、
LiFePO4、LiCoPO4、
一般式Li(1+z)[NiaCobMnc](1−z)O2+e(但し、zは0〜0.3であり、a、b及びcは同一でも異なっていても良く、独立して、a+b+c=1の条件で0〜0.8であり、そして−0.1≦e≦0.1である)の層構造を有する遷移金属酸化物、及び
一般式Li1+tM2−tO4−d(但し、dは0〜0.4であり、tは0〜0.4であり、60モル%超えるMがマンガンであり、さらに30モル%以下のMが周期表の第3〜12族の1種以上の金属である)のスピネル構造のリチウム化遷移金属混合酸化物、から選択される請求項10〜13のいずれか1項に記載のリチウムイオン電池。
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