CN104885286B - 含n杂环阴离子的盐作为电解质中的组分 - Google Patents
含n杂环阴离子的盐作为电解质中的组分 Download PDFInfo
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- CN104885286B CN104885286B CN201380067011.5A CN201380067011A CN104885286B CN 104885286 B CN104885286 B CN 104885286B CN 201380067011 A CN201380067011 A CN 201380067011A CN 104885286 B CN104885286 B CN 104885286B
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- electrolyte
- carbonic acid
- salt
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- 239000003792 electrolyte Substances 0.000 title claims abstract description 37
- 150000003839 salts Chemical class 0.000 title abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 title abstract description 16
- 150000001450 anions Chemical class 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- -1 pyridine ketone Chemical class 0.000 claims description 31
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 150000001768 cations Chemical group 0.000 claims description 9
- 229910001416 lithium ion Inorganic materials 0.000 claims description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 6
- 229910003002 lithium salt Inorganic materials 0.000 claims description 6
- 159000000002 lithium salts Chemical class 0.000 claims description 6
- 229910001415 sodium ion Inorganic materials 0.000 claims description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical class FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002887 superconductor Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000003990 capacitor Substances 0.000 claims 2
- 230000005611 electricity Effects 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007784 solid electrolyte Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910001290 LiPF6 Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000005518 electrochemistry Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 3
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical class COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 229910012265 LiPO2F2 Inorganic materials 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-O 1H-indol-1-ium Chemical compound C1=CC=C2[NH2+]C=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-O 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- CIMQAYVRIDNNIP-UHFFFAOYSA-N FC(C(=O)O)(F)F.COC(OCC)=O Chemical compound FC(C(=O)O)(F)F.COC(OCC)=O CIMQAYVRIDNNIP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910013098 LiBF2 Inorganic materials 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910000552 LiCF3SO3 Inorganic materials 0.000 description 1
- 229910010941 LiFSI Inorganic materials 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- QNDZXYJUJUGCIH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl] hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1C(F)(F)F QNDZXYJUJUGCIH-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 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
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KVMPQUTWRWVTQP-UHFFFAOYSA-N cyanatoboronic acid Chemical compound OB(O)OC#N KVMPQUTWRWVTQP-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- VDGKFLGYHYBDQC-UHFFFAOYSA-N difluoromethyl methyl carbonate Chemical class COC(=O)OC(F)F VDGKFLGYHYBDQC-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- DPGXGQNEWAAUKM-UHFFFAOYSA-N ethenyl 2,2,2-trifluoroethyl carbonate Chemical class FC(F)(F)COC(=O)OC=C DPGXGQNEWAAUKM-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002608 ionic liquid Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- DEUISMFZZMAAOJ-UHFFFAOYSA-N lithium dihydrogen borate oxalic acid Chemical compound B([O-])(O)O.C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.[Li+] DEUISMFZZMAAOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YSYBYIDPNZPQLJ-UHFFFAOYSA-N methyl trifluoromethyl carbonate Chemical class COC(=O)OC(F)(F)F YSYBYIDPNZPQLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000005324 oxide salts Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- QPUMEZIFDXYGPG-UHFFFAOYSA-N piperazine 1H-pyrrole Chemical compound N1CCNCC1.N1C=CC=C1 QPUMEZIFDXYGPG-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 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
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-O quinoxalin-1-ium Chemical compound [NH+]1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-O 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
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Abstract
含N杂环阴离子的盐作为电解质中的组分。描述了含N杂环阴离子的盐的新颖用途，氟化的含N杂环阴离子的新颖的盐以及用于生产它们的方法。优选的化合物具有带有一个三氟甲基的嘧啶酮或吡唑环状结构和金属平衡离子。
Description
本申请要求于2012年12月20日提交的欧洲申请12198765.5的优先权，出于所有的目的将此申请的全部内容通过引用结合在此。
本发明涉及含N杂环阴离子的盐的新颖用途，氟化的含N杂环阴离子的新颖的盐以及用于生产它们的方法。本发明进一步涉及包含含N杂环阴离子的盐的电解质以及包含其的电化学装置，尤其是电池和太阳能电池。
Chai等人(醚官能化的吡唑鎓离子液体作为用于锂电池的新型电解质，电化学学报(Ether-functionalized pyrazolium ionic liquids as new electrolytes forlithium battery,Electrochimica Acta)，66，第67-74页(2012))披露了两种基于吡唑鎓阳离子和双(三氟甲基磺酰基)酰亚胺阴离子(TFSI-)的盐以及它们的物理化学和电化学特性连同它们作为用于锂离子电池的电解质的性能。
国际公开WO 2007/093961 A1披露了在电化学和/或光电装置、尤其太阳能电池中包含四氰基硼酸根和咪唑鎓阳离子的盐作为电解质组分的电解质。
本发明的目的是提供含N杂环阴离子的盐尤其用于电化学装置和/或光电装置用电解质的使用方法。另一个目的是提供氟化的含N杂环阴离子的新颖的盐作为电解质中的组分。这些新颖的盐可展现高的热和/或化学稳定性。此外，本发明的一个目的是提供用于需要在电解质混合物中使用较少单独化合物的电化学装置和/或光电装置的电解质。本发明的使用方法和盐可以提供像改进电解质的粘度或降低电解质的可燃性的优点。另一个优点是在有益薄膜形成下改性电极。此外，本发明的化合物有利地导致隔膜更好的可润湿性。
这些目的以及其他目的通过如说明书以及权利要求书中所概述的本发明得以实现。
因此，本发明涉及具有通式I的化合物
或其任何互变异构体，其中A是包含3个或4个独立地选自C、N、O或S的环状原子的连接基团并且其中Mn⊕是阳离子并且n是1、2、3或4；作为电解质中的组分的使用方法。优选地该电解质被用在锂离子电池、钠离子电池、超导体或有机光电装置中。
如在此使用的“环状的”意思是指一组形成该化合物的环状结构的一部分的原子。例如，具有3个环状原子的基团A产生一种具有通式I的具有五元环结构的化合物。
如在此使用的“阳离子”旨在表示具有正电荷的原子或分子。有利的阳离子的实例是金属离子，硫鎓S+R3(其中R可以独立地选自烷基、烯基或芳基)，磷鎓P+R4(其中R可以独立地选自烷基、烯基或芳基)，铵N+R4(其中R可以独立地选自烷基、烯基或芳基)，以及含N的杂环的，优选咪唑鎓、更优选3-甲基咪唑鎓、或吡唑鎓、更优选氟化的吡唑鎓、又更优选地3-CF3-吡唑鎓，或其任何组合。有利的阳离子的另外的实例包括脲鎓、硫脲鎓、胍鎓、碘鎓和其他杂环的阳离子，如吡啶鎓、喹啉鎓、异喹啉鎓、哌嗪鎓、哌啶鎓、吡咯啉鎓(pyrrolium)、吡嗪鎓(pyrizinium)、吲哚鎓(indolium)、喹喔啉鎓(quinoxalinium)、硫代吗啉鎓、吗啉鎓、以及吲哚鎓阳离子。
已经发现使用金属离子，尤其使用Na+、Li+、或Zn2+是尤其有利的。
术语“烷基”旨在表示饱和的基于烃的基团的任选取代的链，如，具体地，C1-C6烷基。通过举例的方式，可以提及的是甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、异戊基和己基。
术语“烯基”旨在表示碳原子的任选取代的链，其中这些碳原子中的至少两个通过一个双键化学地键合在一起。烯基的实例包括次乙基(乙烯基)、1-丙烯基、2-丙烯基、1-丁烯基。
术语“芳基”旨在是指从芳香核如特别是C6-C10芳香核衍生的任选取代的基团，具体地苯基或萘基。
本发明进一步涉及具有通式I的化合物
或其任何互变异构体，其中A是包含3个或4个独立地选自C、N、O或S的环状原子的连接基团；其中X和Y独立地选自由H、烷基、F和Cl组成的组；并且其中M是金属阳离子并且n是1、2、3或4；以及它们作为电解质中的组分的用途。
在一个优选的方面中，A是–C(O)N＝CH–CH＝并且该化合物是
或其任何互变异构体。
在另一个优选的方面中，A是–N＝CH–CH＝并且该化合物是
或其任何互变异构体。
在另一个优选的方面中，M是Li、Na或Zn。
在另一个优选的方面中，–CFXY是–CF3、–CHF2、或–CClF2，更优选–CF3。
如在此描述的含N杂环阴离子的盐可以被用作电解质中的导电盐和/或溶剂和/或溶剂添加剂。
在另一个实施例中，如在此描述的含N杂环阴离子的盐可以被用作固体电解质，优选地被用作在钠、锂或锌离子电池中、尤其优选的在锂离子电池中的固体电解质。在这个实施例中，它们可以原样或与其他化合物的混合物的形式使用以便形成该固体电解质。使用根据本发明的固体电解质可以使高能电池化学成为可能。附加地，它可以避免与使用液体电解质相关的安全问题。
本发明进一步涉及包含如以上描述的化合物和至少一种其他组分的电解质，优选地该至少一种其他组分是导电盐、溶剂和/或溶剂添加剂。
本发明的化合物可以在该电解质中的0.25至2.5mol/l、优选0.5至1.5mol/l、更优选0.9至1.1mol/l的浓度存在。
在某些实施例中，根据本发明的电解质进一步包含至少一种导电盐，优选Li盐，更优选LiPF6、LiPO2F2、LiBF4、LiB(CN)4、LiAsF6、LiClO4、LiBOB(双草酸硼酸锂)、LiFSI(双(氟磺酰基)亚胺锂)、LiTFSI(双(三氟甲基磺酰基)酰亚胺锂(lithium bis(trifluoromethylsulfonyl)imidide))、LiN(CF3SO2)2)、LiBeti(双(全氟乙基磺酰基)酰亚胺锂)、LiODBF(LiBF2C2O4)、LiB(C6H5)、LiCF3SO3、LiC(CF3SO2)3、以及其任何组合，更优选LiPF6、LiPO2F2、或LiTFSI。在另一个优选的实施例中，该电解质进一步包含一种导电盐，更优选LiPF6。经常，该另外的导电盐的浓度是0.5至1.5mol/l、更优选0.9至1.1mol/l。
在某些实施例中，根据本发明的电解质进一步包含至少一种适合的溶剂，优选有机碳酸酯、内酯、甲酰胺、吡咯烷酮、噁唑烷酮、硝基烷、N,N-取代的尿烷、环丁砜、二烷基亚砜、二烷基亚硫酸酯、乙酸酯、腈、乙酰胺、二醇醚、二氧戊环、二烷基氧乙烷、或三氟乙酰胺。
优选地，该适合的溶剂是碳酸二烷基酯、碳酸亚烷基酯、酮或甲酰胺、二甲基甲酰胺、羧酰胺、丙酮、乙腈、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、环状的碳酸亚烷基酯类，例如碳酸亚乙酯、碳酸亚丙酯或碳酸亚乙烯基酯。
在某些实施例中，根据本发明的电解质进一步包含至少一种溶剂添加剂，该溶剂添加剂选自氟取代的碳酸亚乙酯、多氟取代的碳酸二甲酯、氟取代的碳酸乙甲酯、氟取代的碳酸二乙酯、碳酸单氟亚乙酯、碳酸4,4-二氟亚乙酯、碳酸4,5-二氟亚乙酯、碳酸4-氟-4-甲基亚乙酯、碳酸4,5-二氟-4-甲基亚乙酯、碳酸4-氟-5-甲基亚乙酯、碳酸4,4-二氟-5-甲基亚乙酯、碳酸4(氟甲基)-亚乙酯、碳酸4-(二氟甲基)-亚乙酯、碳酸4(三氟甲基)-亚乙酯、碳酸4-(氟甲基)-4-氟亚乙酯、碳酸4-(氟甲基)-5-氟亚乙酯、碳酸4-氟-4,5-二甲基亚乙酯、碳酸4,5-二氟-4,5-二甲基亚乙酯、和碳酸4,4二氟-5,5-二甲基亚乙酯、碳酸氟甲基甲酯、碳酸二氟甲基甲酯、碳酸三氟甲基甲酯、碳酸双(二氟)甲基酯、和碳酸双(三氟)甲基酯；碳酸乙基甲酯衍生物，包括碳酸2-氟乙基甲酯、碳酸乙基氟甲基酯、碳酸2,2-二氟乙基甲酯、碳酸2-氟乙基氟甲基酯、碳酸乙基二氟甲基酯、碳酸2,2,2-三氟乙基甲酯、碳酸2,2-二氟乙基氟甲基酯、碳酸2-氟乙基二氟甲基酯、以及碳酸乙基三氟甲基酯；以及碳酸二乙酯衍生物，包括碳酸乙基(2-氟乙基)酯、碳酸乙基(2,2二氟乙基)酯、碳酸双(2-氟乙基)酯、碳酸乙基(2,2,2三氟乙基)酯、碳酸2,2-二氟乙基2'-氟乙基酯、碳酸双(2,2-二氟乙基)酯、碳酸2,2,2-三氟乙基2'-氟乙基酯、碳酸2,2,2-三氟乙基2',2'-二氟乙基酯、和碳酸双(2,2,2-三氟乙基)酯、碳酸4-氟-4-乙烯基亚乙酯、碳酸4-氟-5-乙烯基亚乙酯、碳酸4,4-二氟-4-乙烯基亚乙酯、碳酸4,5-二氟-4-乙烯基亚乙酯、碳酸4-氟-4,5-二乙烯基亚乙酯、碳酸4,5-二氟-4,5-二乙烯基亚乙酯、碳酸4-氟-4-苯基亚乙酯、碳酸4-氟-5-苯基亚乙酯、碳酸4,4-二氟-5-苯基亚乙酯、碳酸4,5-二氟-4-苯基亚乙酯和碳酸4,5-二氟-4,5-二苯基亚乙酯、碳酸氟甲基苯基酯、碳酸2-氟乙基苯基酯、碳酸2,2-二氟乙基苯基酯和碳酸2,2,2三氟乙基苯基酯、碳酸氟甲基乙烯基酯、碳酸2氟乙基乙烯基酯、碳酸2,2-二氟乙基乙烯基酯和碳酸2,2,2三氟乙基乙烯基酯、碳酸氟甲基烯丙基酯、碳酸2氟乙基烯丙基酯、碳酸2,2-二氟乙基烯丙基酯和碳酸2,2,2三氟乙基烯丙基酯。
最优选的是一种来自由以下项组成的列表的溶剂：碳酸亚乙酯、碳酸二甲酯、碳酸亚丙酯、碳酸二乙酯、1,2-二甲氧基乙烷、-丁内酯或其混合物，尤其优选的是碳酸亚乙酯与碳酸二甲酯的1:2(v/v)混合物。
在某些实施例中，如在此描述的溶剂还可以充当溶剂添加剂或者如在此描述的溶剂添加剂可以充当溶剂。
本发明还进一步涉及包含根据本发明的含N杂环阴离子的盐或电解质的电化学装置和/或光电装置。该电化学装置和光电装置各自可以选自电池和太阳能电池。优选的装置选自下组，该组由以下项组成：锂离子电池、钠离子电池、锌离子电池、超级电容器或混合型超级电容器、或有机光电装置或染料敏化太阳能电池(DSSC)。
本发明的化合物可以有利地从对应的含N杂环通过与一种适合的碱形成盐来制备。用于制备金属盐的适合碱的实例是LiOH、LiH、丁基锂、Li2O、NaOH、NaH、Na2O、ZnO、或Zn(OH)2。在使用氢氧化物或氧化物盐的情况下所形成的水可以有利地通过共沸或非均相共沸蒸馏、优选地使用迪安-斯达克(dean-stark)装置从该混合物中去除。可替代地，本发明的化合物可以通过盐交换制备，例如通过含N-杂环阴离子的锂盐与所需要阳离子的氯化物盐在一种适合的非质子溶剂中的反应，通过过滤并且蒸馏该非质子溶剂去除所形成的氯化锂。
用于制备这些盐的适合的溶剂是非质子有机溶剂，优选烃类、芳香烃类、二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、乙腈或卤代烃类，更优选芳香烃类，尤其甲苯或苯。
若任何通过引用结合在此的专利、专利申请、以及公开物的披露内容与本申请的描述相冲突的程度到了可能导致术语不清楚，则本说明应该优先。
现在将以多个实例对本发明进一步进行说明，而无意对其进行限制。
实例
2-氧-6-(三氟甲基)嘧啶酮的锂盐的合成
将一种2-氧-6-(三氟甲基)嘧啶-2-酮的样品(根据WO 2010/037688制备的)溶解于甲苯中并且添加1当量干燥的氢氧化锂(以固体形式)。使用迪安-斯达克装置加热所产生的混合物。在不再从该混合物中去除水之后，在60℃和100毫巴的压力下蒸馏出该甲苯。获得了保持在氩气下的固体。
电解质的制备
电解质组合物是通过在氮气氛下将该2-氧-6-(三氟甲基)嘧啶酮的锂盐以1mol/l的浓度添加到一种碳酸亚乙酯与碳酸二甲酯的1:2(v/v)混合物中制备的。
吡唑电解质的直接制备
在氮气下将3-三氟甲基-1H-吡唑(2mol/l)溶解于100ml的1,2-二甲氧基乙烷中。将氢化锂(1当量)添加到该溶液中。在氢气释放停止之后，将100ml碳酸亚乙酯添加到该溶液中。
Claims (17)
1.具有下式的化合物
或下式的化合物
或其任何互变异构体；
其中X和Y独立选自H、烷基、F和Cl；并且
其中是阳离子并且n是1、2、3或4；
作为电解质中的组分的用途。
2.如权利要求1所述的用途，其中M是金属。
3.如权利要求2所述的用途，其中M是Li、Na或Zn½。
4.如权利要求1至3中任一项所述的用途，其中所述化合物为2-氧代-6-(三氟甲基)嘧啶酮的锂盐，或3-三氟甲基-1H-吡唑的锂盐。
5.如权利要求1至3中任一项所述的用途，其中该电解质被用在锂离子电池、钠离子电池、超级电容器、或有机光电装置中。
6.如权利要求1至3中任一项所述的用途，其中该电解质被用在混合型超级电容器中。
7.如权利要求5所述的用途，其中该电解质被用在锂离子电池、钠离子电池、超导体或有机光电装置中。
8.具有下式的化合物
或下式的化合物
或其任何互变异构体，
其中X和Y独立选自H、烷基、F和Cl；并且
其中是金属阳离子并且n是1、2、3或4。
9.如权利要求8所述的化合物，其中所述化合物是
或其任何互变异构体。
10.如权利要求8所述的化合物，其中所述化合物是
或其任何互变异构体。
11.如权利要求8至10中任一项所述的化合物，其中-CFXY是-CF3、-CHF2、或-CClF2。
12.如权利要求11所述的化合物，其中-CFXY是-CF3。
13.如权利要求8至10中任一项所述的化合物，其中M是Li、Na或Zn。
14.如权利要求8至10中任一项所述的化合物，其中所述化合物为2-氧代-6-(三氟甲基)嘧啶酮的锂盐，或3-三氟甲基-1H-吡唑的锂盐。
15.一种电解质，包含如权利要求8至14中任一项所述的化合物和至少一种其他组分。
16.包含如权利要求15所述的电解质的锂离子电池、钠离子电池、锌离子电池、超级电容器或有机光电装置。
17.包含如权利要求15所述的电解质的混合型超级电容器。
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| PCT/EP2013/077534 WO2014096284A1 (en) | 2012-12-20 | 2013-12-19 | Salts of n-containing heterocyclic anions as components in electrolytes |
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| CN108574085A (zh) * | 2018-03-22 | 2018-09-25 | 复旦大学 | 一种低温锌离子电池 |
| DE102018206383A1 (de) * | 2018-04-25 | 2019-10-31 | Bayerische Motoren Werke Aktiengesellschaft | Verfahren zum Betreiben einer Lithiumionenbatterie, Lithiumionenbatterie und Kraftfahrzeug |
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| CN112216871B (zh) * | 2019-07-10 | 2022-04-15 | 比亚迪股份有限公司 | 一种锂离子电池电解液及其制备方法、锂离子电池和电池模组 |
| KR102549395B1 (ko) * | 2019-12-18 | 2023-06-30 | 주식회사 그래피니드테크놀로지 | 이종원소가 도핑된 탄소구조체를 포함하는 이온화합물, 이의 제조방법, 이를 포함하는 전해액 조성물 및 이를 포함하는 전기화학시스템 |
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| EP2936607B1 (en) | 2017-02-22 |
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| JP2016506598A (ja) | 2016-03-03 |
| WO2014096284A1 (en) | 2014-06-26 |
| EP2936607A1 (en) | 2015-10-28 |
| US10038218B2 (en) | 2018-07-31 |
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