WO2013026854A1 - Schwefelhaltige additive für elektrochemische oder optoelektronische vorrichtungen - Google Patents
Schwefelhaltige additive für elektrochemische oder optoelektronische vorrichtungen Download PDFInfo
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- WO2013026854A1 WO2013026854A1 PCT/EP2012/066292 EP2012066292W WO2013026854A1 WO 2013026854 A1 WO2013026854 A1 WO 2013026854A1 EP 2012066292 W EP2012066292 W EP 2012066292W WO 2013026854 A1 WO2013026854 A1 WO 2013026854A1
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- Prior art keywords
- formula
- group
- butyl
- compound
- atoms
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- 239000000654 additive Substances 0.000 title claims abstract description 33
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000011593 sulfur Substances 0.000 title abstract description 5
- 230000005693 optoelectronics Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 239000003792 electrolyte Substances 0.000 claims abstract description 51
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 22
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003990 capacitor Substances 0.000 claims abstract description 12
- -1 alkali metal cation Chemical class 0.000 claims description 56
- 150000001450 anions Chemical class 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052700 potassium Inorganic materials 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 238000005649 metathesis reaction Methods 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 150000000185 1,3-diols Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical group 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 3
- 238000007171 acid catalysis Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 21
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 13
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 229910013870 LiPF 6 Inorganic materials 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 8
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000010439 graphite Substances 0.000 description 7
- 229910002804 graphite Inorganic materials 0.000 description 7
- QYTIAYSDBISYFX-UHFFFAOYSA-N methyl 2-(1-methylpyrrolidin-1-ium-1-yl)ethyl sulfate Chemical compound COS(=O)(=O)OCC[N+]1(C)CCCC1 QYTIAYSDBISYFX-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000035882 stress Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- FSDWUVOPHHTLKC-UHFFFAOYSA-N methyl 3-(1-methylpyrrolidin-1-ium-1-yl)propane-1-sulfonate Chemical compound COS(=O)(=O)CCC[N+]1(C)CCCC1 FSDWUVOPHHTLKC-UHFFFAOYSA-N 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000007784 solid electrolyte Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- KNWFFBQITJOATQ-UHFFFAOYSA-M 2-(1-methylpyrrolidin-1-ium-1-yl)ethanol;chloride Chemical compound [Cl-].OCC[N+]1(C)CCCC1 KNWFFBQITJOATQ-UHFFFAOYSA-M 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000003466 welding Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- GKDCWKGUOZVDFX-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluoro-2,3-bis(trifluoromethyl)butane-2,3-diol Chemical compound FC(F)(F)C(C(F)(F)F)(O)C(O)(C(F)(F)F)C(F)(F)F GKDCWKGUOZVDFX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GOHWWNYKWGRGCD-UHFFFAOYSA-M 1-(3-bromopropyl)-1-methylpyrrolidin-1-ium;bromide Chemical compound [Br-].BrCCC[N+]1(C)CCCC1 GOHWWNYKWGRGCD-UHFFFAOYSA-M 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
- XYBHJMKHOZSMHV-UHFFFAOYSA-N 2-(1-methylpyrrolidin-1-ium-1-yl)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCC[N+]1(C)CCCC1 XYBHJMKHOZSMHV-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- CMQUGOHGJUTDGZ-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)C(F)(F)F CMQUGOHGJUTDGZ-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910001290 LiPF6 Inorganic materials 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 230000029936 alkylation Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000005980 hexynyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000011244 liquid electrolyte Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- MLCJBJOWCHRLKP-UHFFFAOYSA-M methyl 2-(1-methylpyrrolidin-1-ium-1-yl)ethyl sulfate;chloride Chemical compound [Cl-].COS(=O)(=O)OCC[N+]1(C)CCCC1 MLCJBJOWCHRLKP-UHFFFAOYSA-M 0.000 description 2
- 150000005684 open-chain carbonates Chemical class 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- KJEUKJPMTJCVLO-UHFFFAOYSA-M 1-(bromomethyl)-1-methylpyrrolidin-1-ium;bromide Chemical compound [Br-].BrC[N+]1(C)CCCC1 KJEUKJPMTJCVLO-UHFFFAOYSA-M 0.000 description 1
- BPSFARXYWOJZAL-UHFFFAOYSA-M 2-(1-methylpyrrolidin-1-ium-1-yl)ethyl methanesulfonate;chloride Chemical compound [Cl-].CS(=O)(=O)OCC[N+]1(C)CCCC1 BPSFARXYWOJZAL-UHFFFAOYSA-M 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- DTSDUBQXWJFKTP-UHFFFAOYSA-N 4-(3-butylimidazol-1-ium-1-yl)butane-1-sulfonate Chemical compound CCCCN1C=C[N+](CCCCS([O-])(=O)=O)=C1 DTSDUBQXWJFKTP-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- GOEJTGBGHBQFPD-UHFFFAOYSA-N 6-hydroxycyclohex-2-ene-1-carboxylic acid Chemical compound OC1CCC=CC1C(O)=O GOEJTGBGHBQFPD-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
- 229910013131 LiN Inorganic materials 0.000 description 1
- 229910013210 LiNiMnCoO Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000006859 Swern oxidation reaction Methods 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical class [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 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
- 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 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000004821 distillation Methods 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
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011245 gel electrolyte Substances 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000002955 isolation Methods 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
- 229910021450 lithium metal oxide Inorganic materials 0.000 description 1
- 229910001386 lithium phosphate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- SGKVRNQHRQYNGH-UHFFFAOYSA-M methyl sulfate trimethyl(2-phenoxysulfonylethyl)azanium Chemical compound COS([O-])(=O)=O.C[N+](C)(C)CCS(=O)(=O)Oc1ccccc1 SGKVRNQHRQYNGH-UHFFFAOYSA-M 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
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- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 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
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 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
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- STTPRIBCABBCBE-UHFFFAOYSA-N pentanedioic acid propanedioic acid Chemical compound C(CC(=O)O)(=O)O.C(=O)(O)CCCC(=O)O STTPRIBCABBCBE-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002153 silicon-carbon composite material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 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
- 229960003080 taurine Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- 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]
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- 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
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- 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
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- 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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- 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
- Y02E60/13—Energy storage using capacitors
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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- the invention relates to sulfur-containing compounds of the formula I, their preparation and their use as additives in electrochemical or optoelectronic devices, in particular in electrolytes for lithium batteries, lithium-ion batteries, double-layer capacitors, lithium-ion batteries.
- a key component for electrochemical or optoelectronic devices is the electrolyte. This crucially influences the service life, safety and performance of, for example, a lithium-ion cell.
- additives for electrochemical cells in particular for lithium and lithium-ion batteries, as well as double-layer capacitors.
- Virtually every commercially used electrolyte today contains at least one additive. Additives aim to improve the chemical and electrochemical properties of the electrolyte. Even small amounts of additives can significantly improve the properties of the electrolyte.
- additives see, for example, Chem. Rev. 104, 4303-4417).
- Additives are used, for example, to increase the thermal stability or conductivity of the electrolyte, to trap contaminants in the electrolyte (e.g., water or HF), to improve the cycle life, resilience and life of an electrochemical cell, or to increase the safety of the battery.
- contaminants in the electrolyte e.g., water or HF
- organic compounds such as vinylene carbonate, propane sultone or vinyl acetate (to improve cycle stability), biphenyl (overload protection), organic amines (trapping HF) or various sulphones (improvement of thermal stability) are usually used for this purpose.
- SEI Solid Electrolyte Interface
- the lithium ions are not present as "naked" cations, but they are surrounded by solvent molecules.This so-called solvate shell increases the small lithium ion many times.
- solvated lithium ions penetrate into the outer structures of the graphite anode. Since all solvents are under When these extremely reducing conditions are electrochemically unstable, they decompose to form organic lithium salts.
- the lithium salts which are difficult to dissolve in the electrolyte, deposit on the electrode and in the outer structures of the graphite, where they form the layer designated as SEI (see, for example, Chem. Rev. 104, 4303-4417).
- This lithium-ion-permeable but at the same time electronically insulating layer prevents direct contact between the electrode and the solvent. Further decomposition of the solvent is thus prevented.
- the SEI acts desolvat entered, i. The lithium ion strips off the solvent molecules as it passes through and migrates into the electrode as a naked cation. Without this effect, there would be a significant widening of the graphite layers during loading and a contraction when unloading the cell. This "breathing" without an appropriate SEI with increasing charge / discharge cycles would lead to "cracking" of the electrode and thus to a rapid end of life of the battery.
- the structure and properties of the SEI can be significantly influenced by additives. The aim is to achieve an improvement in the cycle stability without generating a deterioration of the internal resistance.
- a first subject of the invention are therefore compounds of the formula (I)
- R are each independently of one another a straight-chain or branched alkyl group having 1 to 20 C atoms which may be non-fluorinated, partially fluorinated or fully fluorinated, a straight-chain or branched alkenyl group having 2 to 20 C atoms and one or more double compounds, a straight-chain or branched alkynyl group having 2 to 20 C atoms and one or more triple bonds or an aryl group having 6 to 12 C atoms, which are characterized by F, Cl and / or a straight-chain or branched, partially fluorinated or completely fluorinated alkyl group with 1 to 8 carbon atoms can be substituted one or more times, means
- K is a cation selected from the group
- R each independently of one another methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl, where at least one, not directly connected to N or P, Ch group of said radicals R is replaced by O,
- R ' is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl,
- A is an anion selected from the group
- n 1, 2, 3, 4, 5, 6, 7 or 8, it being possible for some CF 2 groups in the abovementioned anions to be replaced by O, S (O) 2, NR or CH,
- z is 1, 2, 3 or 4,
- y is 1, 2, 3, 4, 5 or 6,
- R 1 and R 2 are each independently of one another F, Cl, Br, I, a straight-chain or branched perfluoroalkyl group having 1 to 20 C atoms, a straight-chain or branched alkoxy group having 1 to 20 C atoms, which are not fluorinated, partially fluorinated or is completely fluorinated, or - represents 0-C (0) -alkyl, where alkyl is a straight-chain or branched alkyl group having 1 to 20 C atoms, which may be non-fluorinated, partially fluorinated or perfluorinated,
- each independently is a bidentate radical derived from a 1, 2 or 1, 3-diol, from a 1, 2 or 1, 3-dicarboxylic acid or a 1, 2 or 1, 3-hydroxycarboxylic acid, in each two adjacent OH groups of the corresponding compound with the central atom X each enter into a bond and thereby formally split off two H atoms and wherein the electroneutrality of the corresponding salt of the formula (I) is to be observed.
- the compounds of the formula (I) according to the invention form at passivities between about 2.5 V and 0.9 V versus Li / Li + a passivating covering layer on the negative electrode, the so-called SEI, as described above.
- a surprising and prominent feature of these compounds of formula (I) is that they are used as additives in electrolytes, generally do not lead to an increase in the internal resistance of the electrochemical cell such. Vinylene carbonate or propane sultone.
- the compounds of the formula (I) are salts, they are generally non-volatile and have no measurable vapor pressure. This is a further advantage over the previously used organic additives, for example propane sultone.
- the quaternary ammonium salts of the described taurine esters are water-soluble microcidal compounds, in particular for Al genbehimung.
- the counterion of these quaternary ammonium salts is methylsulfate, for example in the compound TAS, also known under the trade name Sepacid®, ie the tetramethylammonium salt of the taurine phenyl ester or else synonymously to it phenyloxysulphonylethyl-trimethylammonium methylsulfate.
- WO 2005/055286 describes zwitterionic compounds of the formula
- R 2 O- N -CH 2 -R 3 -N- (CO) -R 3 or N-SO 2 - wherein Ri + denotes a heterocyclic cation, an ammonium cation, a guanidinium cation or a phosphonium cation,
- a a spacer and R3 is H, alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl or aryl, for use in a solar cell as a component of charge transport layers. Representatively, the following compounds are described:
- WO 2006/017898 describes zwitterionic additives for electrochemical devices of the general structure cation-spacer anion.
- Representative compounds for these zwitterions i. for compounds bearing both a positive charge and a negative charge in a molecule, the compounds are N-methyl-N- (n-butanesulfonate) pyrrolidinium
- a straight-chain or branched alkyl group having 1 to 20 C atoms is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, and also pentyl, 1-, 2- or 3-methylbutyl, 1, 1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl, which may be also partially fluorinated or completely fluorinated (synonymous perfluorinated) may be.
- perfluorinated indicates that all H atoms in the specified alkyl group are substituted by F atoms
- partially fluorinated indicates that at least one H atom in the specified alkyl group is substituted by an F atom
- Examples of partially fluorinated or perfluorinated alkyl groups are difluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
- a straight-chain or branched alkenyl group having 2 to 20 C atoms, in which several double bonds may also be present, is for example allyl, 2- or 3-butenyl, isobutyl, sec-butenyl, furthermore 4-pentenyl, iso-pentenyl , Hexenyl, heptenyl, octenyl, -C9H17, -C10H19 to -C20H39; preferably allyl, 2- or 3-butenyl, iso-butenyl, sec-butenyl, furthermore preferably 4-pentenyl, iso-pentenyl or hexenyl.
- a straight-chain or branched alkynyl group having 2 to 20 C atoms, in which a plurality of triple bonds may also be present is, for example, ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl , Heptynyl, octynyl, -C9H15, -C10H17 to -C20H37, preferably ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, 4-pentynyl, 3-pentynyl or hexynyl.
- a straight-chain or branched alkoxy group having 1 to 20 C atoms is, for example, methoxy, ethoxy, isopropoxy, propoxy, butoxy, sec-butoxy or tert-butoxy, and also pentoxy, 1, 2 or 3 Methylbutoxy, 1, 1-, 1, 2- or 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy or Eicosyloxy, which may not be fluorinated, partially fluorinated or fully fluorinated.
- partially fluorinated indicates that at least one H atom in the indicated alkoxy group is substituted by an F atom.
- fully fluorinated indicates that all H atoms in the indicated alkoxy group are replaced by F atoms. Atoms are substituted.
- An aryl group having 6 to 12 C atoms is, for example, phenyl, naphthyl or phenanthryl, which may be monosubstituted or polysubstituted by F, Cl and / or a straight-chain or branched, partially fluorinated or fully fluorinated alkyl group having 1 to 8 C atoms, preferably phenyl which may be monosubstituted or polysubstituted by F, Cl and / or a straight-chain or branched, partially fluorinated or completely fluorinated alkyl group having 1 to 8 C atoms, for example o-, m- or p-methylphenyl, o-, m- or p-ethylphenyl, o-, m- or p-propylphenyl, o-, m- or p- (iso-propyl) phenyl, o-, m- or p- (tert-butyl
- the aryl group having 6 to 12 C atoms particularly preferably denotes phenyl which may be mono- or polysubstituted by F and / or a straight-chain or branched, partially fluorinated or perfluorinated alkyl group having 1 to 8 C atoms.
- Suitable 1,2- or 1,3-diols for producing the bidentate radical as described above are both aliphatic and aromatic, for example 1,2-dihydroxybenzene (catechol, pyrocatechol), propane-1,2-diol, butane 1, 2-diol, propane-1, 3-diol, butane-1, 3-diol, cyclohexyl Trans 1, 2-diol or naphthalene-2,3-diol, which may optionally be monosubstituted or polysubstituted with F and / or at least one straight-chain or branched, non-fluorinated, partially fluorinated or perfluorinated alkyl group having 1 to 4 carbon atoms ,
- An example of such substituted 1, 2 or 1, 3-diols is 1, 1, 2,2-tetra (trifluoromethyl) -1, 2-ethanediol.
- Suitable 1, 2 or 1, 3-dicarboxylic acids for producing the bidentate radical are both aliphatic and aromatic, for example oxalic acid, malonic acid (propane-1,3-dicarboxylic acid), phthalic acid or isophthalic acid, optionally with F and / or at least one straight-chain or branched, non-fluorinated, partially fluorinated or perfluorinated alkyl group having 1 to 4 C atoms may be monosubstituted or polysubstituted.
- Suitable 1, 2 or 1, 3-hydroxycarboxylic acids for producing the bidentate radical as described above are both aliphatic and aromatic, for example salicylic acid, tetrahydrosalicylic acid, malic acid, 2-hydroxyacetic acid, optionally with F and / or at least one straight chain or branched, non-fluorinated, partially fluorinated or perfluorinated alkyl group having 1 to 4 carbon atoms may be monosubstituted or polysubstituted.
- An example of such substituted 1, 2 or 1, 3-hydroxycarboxylic acids is 2,2-bis (trifluoromethyl) -2-hydroxy-acetic acid.
- variable u is 0, 1, 2, 3, 4, 5, 6 or 7, preferably u is 1, 2 or 3.
- the - (Ch alkylene chain is unsubstituted and u has one of the above indicated or preferred meanings.
- variable v means 0, 1, 2, 3 or 4, preferably v stands for 0.
- -S0 3 - represents ⁇
- R preferably in each case independently of one another represents a straight-chain or branched alkyl group having 1 to 20 C atoms, which may not be fluorinated, partially fluorinated or fully fluorinated, a straight-chain or branched alkenyl group having 2 to 4 C atoms.
- Atoms and one or more double bonds or a straight-chain or branched alkynyl group having 2 to 4 C atoms and one or more triple bonds for example methyl, ethyl, trifluoromethyl, pentafluoroethyl, n-propyl, n-butyl, n-hexyl, n-octyl, Ethenyl, ethynyl, allyl or prop-1-yn-yl.
- R " is, independently of one another, a straight-chain or branched alkyl group having 1 to 8 C atoms, which may be non-fluorinated, partially fluorinated or fully fluorinated.
- variable Y in the formulas for the cations K means CH 2 , O, S or NR ', where R' is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl, more preferably Y is CH 2 .
- the substituent R in the formulas for the cations K preferably denotes methyl, ethyl, n-propyl or n-butyl, particularly preferably methyl.
- K is preferably the cation, where Y and R are the pyrrolidines
- variable m in the formulas of the anions A is preferably 1, 2, 3, 4, 5, 6, 7 or 8, particularly preferably 2, 3 or 4, very particularly preferably 2 or 4.
- variable y in the formulas of the anions A means 1, 2, 3, 4, 5 or 6, preferably 3, 4 or 5, more preferably 3 or 5, most preferably 3.
- variable z in the formulas of the anions A as described above means 1, 2, 3 or 4, preferably 1, 2 or 3, most preferably 3.
- variable X in the formulas of the anions A as described above means B or Al, preferred B.
- A is preferably an anion selected from the group
- n 1, 2, 3, 4, 5, 6, 7 or 8
- z 1, 2 or 3
- y is 3, 4, 5 or 6
- R 1 and R 2 are each independently of one another F, a straight-chain or branched perfluoroalkyl group having 1 to 4 C atoms, a straight-chain or branched alkoxy group having 1 to 4 C atoms or -O-C (O) -alkyl, where Alkyl is a straight-chain or branched alkyl group having 1 to 20 C atoms, which may not be fluorinated, partially fluorinated or perfluorinated,
- each independently is a bidentate radical derived from a 1, 2 or 1, 3-diol, from a 1, 2 or 1, 3-dicarboxylic acid or a 1, 2 or 1, 3-hydroxycarboxylic acid, in each two adjacent OH groups of the corresponding compound with the central atom X each enter into a bond and thereby formally split off two H atoms.
- A is more preferably an anion selected from the group
- n 2, 3 or 4
- y 3, 4 or 5
- each independently is a bidentate radical derived from a 1, 2 or 1, 3-diol, from a 1, 2 or 1, 3-dicarboxylic acid or a 1, 2 or 1, 3-hydroxycarboxylic acid, in each two adjacent OH groups of the corresponding compound with the central atom X each enter into a bond and thereby formally split off two H atoms.
- Preferred anions of the formula [F z B (C m F 2m + i) 4-z] " are the anions [FsB (CF 3)] " or [FsB (C 2 F 5 )] -.
- Preferred anions of the formula [F y P (C m F 2m + i) 6-y] " are the anions [PFe] " , [F 3 P (C 2 F 5 ) 3] " ,
- Preferred anions of the formula [(C m F 2m + i) 2 P (0) O] " are the anions [(C 2 F 5 ) 2 P (O) O] " ,
- Preferred anions of the formula [0-C (0) CmF 2m + i] - are the anions [0-C (0) CF 3 ] -, [0-C (0) C 2 F 5 ] - or [0-C ( 0) C 4 F 9 ] -, more preferably [0-C (0) CF 3 ] -.
- Preferred anions of the formula [O-S (O) 2C m F 2m + i] " are the anions [O-S (O) 2CF 3 ] - or [O-S (O) 2C 2 F 5 ] -, particularly preferably 0-S (0) 2 CF 3 ] -.
- Preferred anions of the formula [N (C (O) C m F 2m + i) 2] " are the anions [N (C (O) C 2 F 5 ) 2] " or
- Preferred anions of the formula [N (S (O) 2C m F 2m + i) 2] " are the anions [N (S (O) 2 CF 3 ) 2] " ,
- Preferred anions of the formula [N (C (O) C m F 2m + i) (C (O) F)] - are the anions
- Preferred anions of the formula [N (S (O) 2C m F 2m + i) (S (O) 2 F)] - are the anions
- Preferred anions of the formula [C (C (O) C m F 2m + i) 3 ] " are the anions [C (C (O) CF 3 ) 3 ] -,
- Preferred anions of the formula [C (S (O) 2C m F 2m + i) 3 ] " are the anions [C (S (O) 2 CF 3 ) 3 ] -,
- Preferred anions of the formula the anions are bis (catecholato) borate, where both bidentate radicals are based on 1, 2-dihydroxybenzene, bis (oxalato) borate, where both bidentate radicals are based on oxalic acid, bis (malonato) borate, where both bidentate radicals are based on malonic acid , Malonato oxalato borate, wherein a bidentate moiety is based on malonic acid and a bidentate moiety on oxalic acid, naphtholato oxalatoborate, wherein a bidentate moiety is based on naphthalene-2,3-diol and a bidentate moiety is based on oxalic acid, bis (naphtholato) borate, both being bidentate Residues based on naphthalene-2,3-diol or bis (salicylato) borate
- the anions are difluoro-oxalato-borate, di-trifluoroacetato-oxalato-borate, difluoro-di- (trifluoromethyl) -glycano-borate, the bidentate radical being based on 2,2-bis (trifluoromethyl) -2-hydroxy-acetic acid, difluoro perfluoropinacolato borate, the bidentate radical being based on 1, 1, 2,2-tetra (trifluoromethyl) -1,2-ethanediol, trifluoromethylmethoxy-oxalato-borate, pentafluoroethyl-methoxy-oxalato-borate, trifluoromethylmethoxy catecholato borate, pentafluoroethyl methoxy catecholato borate, trifluoromethyl methoxy malonato borate, pentafluoroethyl methoxy malonato borate, pen
- the process steps can be carried out in the air, preferably in a dry atmosphere, for example under dry air, nitrogen or argon.
- Another object of the invention is therefore a process for the preparation of compounds of formula I, as described above or described as preferred, wherein SO3 of the partial
- K-1 is selected from the group R3N, R3P,
- R each independently of one another methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl, where at least one, not directly connected to N or P, CH 2 - group of said radicals R can be replaced by O,
- Y is CH 2 , O, S or NR 'and
- R ' is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl,
- Hal (CH 2 ) - (CH 2 ) u-OH (IN), where u is 1, 2, 3, 4, 5, 6 or 7, where at least one non-oxygen-bonded CH 2 group of the - ( CH 2 ) U- alkylene chain with u 3, 4, 5, 6 or 7 may be replaced by O or may contain at least one double bond, and Hal is Cl, Br or I, and the resulting intermediate of the formula (IV) [K- (CH 2 ) - (CH 2 ) u -OH] + [Hal] - (IV), where K, u and Hai have one of the meanings given above,
- v and R have the abovementioned meaning and L denotes a leaving group selected from a straight-chain or branched alkoxy group having 1 to 3 C atoms, Cl or F means, preferably Cl or F,
- the compound of the formula (IIIa) can be prepared by methods known from the literature, for example as described in NJ Putochin, Chem. Berichte, 55, 1922, pages 2749-2753.
- the reaction of the compounds of the formula II with compounds of the formula III, as described above, generally takes place at reaction temperatures between 10.degree. C. and 200.degree. C., preferably between 20.degree. C. and 100.degree. As a rule, no solvent is used.
- the reaction takes place under acid catalysis, for example in the presence of sulfuric acid, toluenesulfonic acid, methane- or ethanesulfonic acid, Nafion®, Amberlite® or Amberlyst® in acidic form Shape.
- the reaction takes place in the presence of a base, for example inorganic bases such as KOH, NaOH, Na 2 CO 3, NaHCO 3 or organic bases such as triethylamine, diisopropylethylamine or pyridine ,
- a base for example inorganic bases such as KOH, NaOH, Na 2 CO 3, NaHCO 3 or organic bases such as triethylamine, diisopropylethylamine or pyridine ,
- This substitution reaction preferably takes place in the presence of an organic solvent.
- the addition of the compound of formula V takes place at temperatures between -10 ° C and room temperature. To complete the reaction, heating to reflux may be recommended in some cases.
- the usual time of heating is in the Order of hours, with distillation, to remove the formed alcohol (methanol).
- the metathesis reaction is preferably carried out in water, temperatures of 10 ° -100 ° C, preferably 15 ° -60 ° C, particularly preferably room temperature, are suitable. Alternatively, however, the reaction can also be carried out in organic solvents at temperatures between 10 ° and 100 ° C. Suitable solvents are acetonitrile, acetone, 1, 4-dioxane, dichloromethane, dimethoxyethane or an alcohol, for example methanol, ethanol or isopropanol.
- Another object of the invention is a process for the preparation of compounds of formula (I), as described above or described as preferred, wherein SO3 of the partial structure
- ⁇ and u means 2, 3, 4 or 5, characterized in that a
- K-1 is selected from the group R3N, R3P, RR
- R each independently of one another methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl, where at least one, not directly connected to N or P CH 2 group of said radicals R is replaced by O,
- Y is CH 2 , O, S or NR 'and
- R ' is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl,
- the - (CH 2) -cycloalkylene chain of compound VIII can also contain at least one double bond (AL Flohic et al., Synlett, No. 5 (2003), pp. 667-670), but according to general knowledge not at the carbon atoms, which form a direct bond with the heteroatoms S and O.
- reaction of the commercially available compounds of the formula II, as described above, with the sultans of the formula VIII takes place without solvent or in an organic solvent, preferably in an organic solvent, for example in toluene, acetonitrile, dioxane, acetone, monoglyme, diglyme or in mixtures of acetonitrile with dialkyl ethers, more preferably in toluene.
- the reaction takes place at temperatures between -10 ° C and room temperature. To complete the reaction, refluxing may be recommended in some cases.
- the alkylation can be carried out without solvents, temperatures of 0 ° -150 ° C., preferably 0 ° -80 ° C., particularly preferably room temperature, being suitable.
- reaction also takes place in the presence of an organic solvent, for example acetonitrile, propionitrile, benzonitrile, dialkyl ethers, dichloromethane, monoglyme, diglyme, more preferably in acetonitrile.
- organic solvent for example acetonitrile, propionitrile, benzonitrile, dialkyl ethers, dichloromethane, monoglyme, diglyme, more preferably in acetonitrile.
- the reaction temperature is between 0 ° C and 150 ° C, preferably between 0 ° C and 80 ° C. Particularly preferred is reacted at room temperature.
- the intermediate of formula IX may be reacted first with an acid [H] + [A] -, wherein A has the meaning given above, and in a further step with a diazo compound of formula N 2 - (CH 2 ) V -R be directly alkylated to compound of formula I, wherein v and R "have the meaning given above.
- Another object of the invention is a process for the preparation of compounds of formula I, as described above or described as preferred, wherein SO3 of the partial structure
- ⁇ corresponds, characterized in that a compound of formula (II) K-1 (Ii), where K-1 is selected a
- R each independently of one another are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl, it being possible for individual CH 2 groups not directly linked to N or P to be replaced by O. .
- Y is CH 2, O, S or NR 'and
- R ' is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl,
- Hal (CH 2 ) - (CH 2 ) u-Hal (XII), where u is 0, 1, 2, 3, 4, 5, 6 or 7, where at least one non-Hai-attached Ch group of - ( CH 2 ) U- alkylene chain with u 2, 3, 4, 5, 6 or 7 may be replaced by O or may contain at least one double bond and Hai denotes Cl, Br or I,
- a compound of formula (II) as described above may first be obtained with Hal- (CH 2) - (CH 2) u S (O) 20 Na of formula (XIIa) (Hal is preferably Br or I and u has one of the abovementioned Meanings) to an intermediate of formula (IX) as described above, and further reacted with an alkylating agent of formula (X) as previously described.
- the reaction conditions of such substitutions are well known to those skilled in the art of organic synthesis.
- a further object is an electrolyte comprising at least one compound of the formula (I) as described above or described as being preferred.
- an electrolyte is any substance that contains free ions and is therefore electrically conductive.
- the most typical electrolyte is an ionic solution, but
- An electrolyte according to the invention or a corresponding electrolyte formulation is therefore an electrically conductive medium, mainly due to the presence of at least one substance which is in dissolved and / or molten state, i. supports electrical conductivity by movement of ion species.
- the compounds of the formula I take over the function of an additive in the electrolyte.
- the compounds of the formula I take on the function of an additive, which in particular has a positive effect on the generation of the SEI.
- the typical concentration is between 0.05 and 10% by weight, preferably between 0.05 and 5%, based on the total weight of the electrolyte.
- the molarity refers to the concentration at 25 ° C.
- Another object of the invention is therefore the use of compounds of formula (I), as described above, as an additive in electrolytes.
- the compounds of the formula (I) according to the invention, as described above, are preferably used in lithium batteries or lithium ion batteries or are preferably used in electrolytes which are suitable for these electrochemical devices. Therefore, in addition to the compounds of the formula (I) as described above or preferably described, the electrolyte according to the invention preferably contains a conductive salt, preferably selected from a lithium salt and / or a tetraalkylammonium salt, the alkyl groups each independently of one another having an alkyl group with 1 to 4 carbon atoms.
- the conductive salt is a lithium secondary salt such as LiPF 6 , LiBF 4 , LiN (SO 2 F) 2 , LiN (SO 2 CF 3 ). 2 , LiN (S0 2 C 2 F 5 ) 2 , LiF 5 P (C 2 F 5 ), LiF 5 P (C 3 F 7 ), LiF 5 P (C 4 F 9 ), LiF 3 P (C 2 F 5 ) 3 , LiF 3 P (C 4 F 9 ) 3 , LiB (C 2 O 4 ) 2 or LiF 2 B (C 2 O 4 ) 2 .
- the conducting salt is a tetraalkylammonium salt from the group
- the electrolytes of the invention preferably contain an aprotic solvent or solvent mixture, and optionally one or more further additives. They may be used in combination with other conductive salts and / or additives, as part of a polymer electrolyte or phase transfer medium.
- the aprotic solvent of the electrolyte preferably consists of organic open-chain or cyclic carbonates, carboxylic acid esters, nitriles, silanes or sulfonic acid esters or a mixture thereof. Nitriles, in particular acetonitrile, are preferably used as solvents in double-layer capacitors.
- Preferred open-chain or cyclic carbonates are diethyl carbonate, dimethyl carbonate, ethyl methyl carbonate, ethylene carbonate or propylene carbonate.
- Preferred carboxylic acid esters are ethyl acetate or methyl propionate.
- Preferred nitriles are adiponitrile, valeronitrile and acetonitrile, particularly preferably acetonitrile.
- the organic solvent is preferably contained in the electrolyte in 5 to 90% by weight, preferably in 40 to 90% by weight, the weight percentage being based on the total electrolyte.
- Further additives may be, for example, from the known additives vinylene carbonate, propane sultone, vinyl acetate, biphenyl, cyclohexylbenzene, organic amines, for example trialkylamines, dialkylphenylamines or N-silylated amines, such as trimethylsilylimidazole as an example of an N-silylated cyclic amine, or different sulphones , For example, diphenyl sulfone, are selected, wherein the alkyl groups in the mentioned amines can each independently be a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
- the additives of the group mentioned are vinylene carbonate, propanesultone, vinyl acetate, biphenyl, cyclohexylbenzene, organic amines, N-silylated amines or sulphones, where the alkyl groups in the amines mentioned each independently of one another may be a straight-chain or branched alkyl group having 1 to 20 carbon atoms, in which electrolytes are contained.
- gel-forming additives for so-called gel electrolytes, which are electrolytes that assume a "quasi-solid" state, have structural properties of solid electrolytes but retain conductive properties such as liquid electrolytes.
- Such gel additives may be selected from inorganic particulate materials, for example, S1O2, ⁇ 2 or Al2O3.
- the electrolytes according to the invention may contain such gel additives in 0.01 to 20% by weight, based on the total electrolyte, preferably in 1 to 10% by weight.
- a solvent in the electrolyte of the invention may further contain a polymer, wherein the polymer is polyvinylidene fluoride, polyvinylidene-hexafluoropropylene, polyvinylidene-hexafluoropropylene-chlorotrifluoroethylene copolymers, Nafion, polyethylene oxide, polymethyl methacrylate, polyacrylonitrile, polypropylene, polystyrene Polybutadien, polyethylene glycol, polyvinylpyrrolidone, polyaniline, polypyrrole, polythiophene.
- These polymers are added to the electrolyte to convert liquid electrolytes into quasi-solid or solid electrolytes, thus improving solvent retention, especially on aging.
- electrolytes according to the invention are prepared by methods known to those skilled in the art of preparing electrolytes, generally by dissolving the conducting salt in the corresponding solvent mixture and adding the additives of the formula I according to the invention, as described above.
- Another object of the invention is an electrochemical or electro-optical device containing at least one compound of formula I, as described above or described as preferred.
- the device may preferably be a lithium battery, a lithium-ion battery, a double-layer capacitor, a lithium-ion capacitor, a solar cell, an electrochromic display, a sensor or a biosensor.
- the solar cell is a dye solar cell.
- a lithium battery is a battery in which a lithium-metal electrode is used as a negative electrode
- a lithium-ion battery uses as a negative electrode materials in which lithium ions can be reversibly incorporated and removed.
- Examples include graphite, silicon or silicon-carbon composites, tin oxides or lithium titanium oxides.
- the anode consists of carbon / graphite, the cathode of a lithium metal oxide or lithium phosphate and the separator made of polypropylene / polyethylene or ceramic film.
- the synthesized compounds are characterized by NMR spectroscopy.
- the NMR samples are measured in 5mm NMR tubes at 25 ° C in a Bruker Avance III spectrometer equipped with a 9.3980T cryomagnet.
- the 1 H and 19 F NMR spectra are measured using a 5 mm combination 1 H / 19 F probe operating at 400.17 and 376.54 MHz.
- the 13 C NMR spectra are obtained using a 5mm broadband inverse probe at 100.62 MHz.
- the reference in the 1 H NMR spectra is tetramethylsilane (TMS) using chemical shifts of CHCI 3 (7.23 ppm) and CH 3 CN (1.96 ppm) solvents.
- TMS tetramethylsilane
- NMR corresponds to the product of the reaction of methylpyrrolidine with 1,3-propane sultone (Example 1). methyl) -1-methylpyrrolidinium bromide
- test cells used are lithium-ion cells consisting of a graphite electrode, a polyolefin-based separator and a LiNiMnCoO 2 electrode (electrode area per 25 cm 2 , pouch-cell structure).
- the anode is placed in the middle of the laminated aluminum foil so that the Abieiter projects approx. 20 mm beyond the foil.
- the cathode is placed on the anode so that the anode forms a uniform frame around the cathode.
- a second laminated aluminum foil is placed in such a way that both foils overlap one above the other.
- a PE foil is placed between the current conductor and the laminated aluminum foil.
- a welding seam is set with the welding tongs (temperature 225 ° C), so that the electrode stack can no longer slip.
- both electrodes are wetted with 1 ml of the electrolyte to be tested and a polyolefin separator, which was previously placed for 5 min in an electrolyte-filled Petri dish, placed between the anode and cathode.
- test cell is evacuated with the vacuum welder and sealed.
- ⁇ Voltage and resistance of the test cell are checked with a commercially available multimeter and lie between -0.200 to 0.200 V or between 0.05 and 1 Ohm. Cells that are outside the values are not used.
- Cycle 1 Charging rate: 0.3C Discharge rate 0.3C
- Cycle 52 Charging rate: 1 C Discharge rate 2C
- Cycle 53 Charging rate: 1 C Discharge rate 4C
- Cycle 54 Charging rate: 1 C Discharge rate 6C ⁇ Cycle 55: Charging rate: 1 C Discharge rate 8C
- Cycle 56 Charging rate: 1 C Discharge rate 10C
- the measuring instrument / cyclizer is a commercially available instrument from BaSyTec.
- User Example A Reference / comparison system
- the load capacity (1 C -10 C - the discharge capacity at 1 C is set as 100%) is shown in FIG. 1.
- Table 1 shows the results of the stress test:
- FIG. 2 shows the course of the internal resistance in the uncharged state (3.0 V).
- Table 2 is a summary of the cycle test (the discharge capacity in the 10th cycle is set to 100%)
- Table 3 is a summary of the relative discharge capacity at 10C (the discharge capacity of the 1.1C discharge is set at 100%)
- Example B Electrolyte containing 1- (3- (methoxysulphonyl) propyl) -1-methylpyrrolidinium tris (pentafluoroethyl) trifluorophosphate
- FIG 3 shows the load capacity 1 C to 10 C: the discharge capacity at 1 C is set as 100%.
- Table 5 gives a summary of the cycle test (the discharge capacity in the 10th cycle is set to 100%).
- Table 6 gives a summary of the relative discharge capacity at 10C (the discharge capacity of the 1.1C discharge is set to 100%).
- Example C Electrolyte containing 1-methyl-1 - (2- (methylsulfoxy) ethyl) -pyrrolidinium tris (pentafluoroethyl) trifluorophosphate
- FIG. 5 shows the load capacity 1 C to 10 C: the discharge capacity at 1 C is set as 100%.
- FIG. 6 shows the course of the internal resistance in the uncharged state (3.0 V).
- Table 8 shows the summary of the cycle test (the discharge capacity in the 10th cycle is set to 100%).
- Table 9 gives a summary of the relative discharge capacity at 10C (the discharge capacity of the 1.1C discharge is set to 100%).
- Relative discharge capacity 43 42 39 39 35 36% at 10C the first load of 10C shows a significantly higher removable capacity of 43% compared to the reference (FIG. 5).
- Example D Electrolyte containing 1-methyl-1 - (2- (methylsulfoxy) ethyl) -pyrrolidinium bis (oxalato) borate
- FIG. 7 shows the capacity 1 C to 10 C: The discharge capacity at 1 C is set as 100%.
- FIG. 8 shows the course of the internal resistance in the uncharged state (3.0 V).
- Table 1 shows the summary of the cycle test (the discharge capacity in
- Table 12 shows the summary of the relative discharge capacity at 10C (the discharge capacity of the 1.1C discharge is set at 100%).
- FIG. 1 shows the load capacity 1C to 10C of the reference system 1M LiPF 6 in EC: DMC (1: 1).
- FIG. 2 shows the course of the internal resistance in the uncharged state (3.0 V) of the reference system 1 M LiPF 6 in EC: DMC (1: 1).
- FIG. 3 shows the load capacity 1C to 10C of example B 1M LiPF 6 in EC: DMC (1: 1), 1% 1- (3
- Figure 4 shows the course of the internal resistance in the uncharged state (3.0 V) of Example B.
- FIG. 5 shows the load capacity 1C to 10C of the example C 1M LiPF 6 in EC: DMC (1: 1), 1% 1
- FIG. 6 shows the course of the internal resistance in the uncharged state (3.0 V) of example C.
- FIG. 7 shows the loading capacity 1C to 10C of Example D 1M LiPF 6 in EC: DMC (1: 1), 1% 1-methyl-1- (2- (methylsulfoxy) ethyl) -pyrrolidinium bis (oxalato) borate.
- FIG. 8 shows the course of the internal resistance in the uncharged state (3.0 V) of the example D 1M LiPF 6 in EC: DMC (1: 1), 1% of 1-methyl-1- (2- (methylsulfoxy) ethyl) -pyrrolidinium borate bis (oxalato).
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Abstract
Description
Claims
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CN201280041073.4A CN103764628B (zh) | 2011-08-24 | 2012-08-22 | 用于电化学或光电装置的含硫添加剂 |
EP12762544.0A EP2748145B1 (de) | 2011-08-24 | 2012-08-22 | Schwefelhaltige additive für elektrochemische oder optoelektronische vorrichtungen |
KR1020147007141A KR102072367B1 (ko) | 2011-08-24 | 2012-08-22 | 전기화학 또는 광전자 소자용 황-함유 첨가제 |
JP2014526482A JP5724042B2 (ja) | 2011-08-24 | 2012-08-22 | 電気化学または光電子デバイスのための硫黄含有添加剤 |
US14/239,908 US9748605B2 (en) | 2011-08-24 | 2012-08-22 | Sulfur-containing additives for electrochemical or optoelectronic devices |
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DE102011111059 | 2011-08-24 | ||
DE102011111059.7 | 2011-08-24 |
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US (1) | US9748605B2 (de) |
EP (1) | EP2748145B1 (de) |
JP (1) | JP5724042B2 (de) |
KR (1) | KR102072367B1 (de) |
CN (1) | CN103764628B (de) |
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CN103764628A (zh) | 2014-04-30 |
US9748605B2 (en) | 2017-08-29 |
JP2014529601A (ja) | 2014-11-13 |
JP5724042B2 (ja) | 2015-05-27 |
EP2748145B1 (de) | 2016-10-19 |
TW201313693A (zh) | 2013-04-01 |
CN103764628B (zh) | 2016-09-21 |
US20140193707A1 (en) | 2014-07-10 |
EP2748145A1 (de) | 2014-07-02 |
TWI574950B (zh) | 2017-03-21 |
KR102072367B1 (ko) | 2020-02-03 |
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