CN110892568B - 改性三嗪功能性化合物 - Google Patents
改性三嗪功能性化合物 Download PDFInfo
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- CN110892568B CN110892568B CN201880046948.7A CN201880046948A CN110892568B CN 110892568 B CN110892568 B CN 110892568B CN 201880046948 A CN201880046948 A CN 201880046948A CN 110892568 B CN110892568 B CN 110892568B
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- Prior art keywords
- equal
- electrolyte
- alkyl
- lithium
- containing compound
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- 150000001875 compounds Chemical class 0.000 title claims description 24
- 150000003918 triazines Chemical class 0.000 title description 2
- 239000003792 electrolyte Substances 0.000 claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 17
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011574 phosphorus Substances 0.000 claims abstract description 11
- -1 alkali metal salt Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 33
- 239000000654 additive Substances 0.000 claims description 24
- 230000000996 additive effect Effects 0.000 claims description 18
- 239000002608 ionic liquid Substances 0.000 claims description 17
- 229910052744 lithium Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910001416 lithium ion Inorganic materials 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 8
- 238000004146 energy storage Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 150000003462 sulfoxides Chemical class 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 239000003990 capacitor Substances 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052609 olivine Inorganic materials 0.000 claims description 5
- 239000010450 olivine Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 229910001415 sodium ion Inorganic materials 0.000 claims description 4
- 229910052596 spinel Inorganic materials 0.000 claims description 4
- 239000011029 spinel Substances 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 150000005684 open-chain carbonates Chemical class 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 239000002210 silicon-based material Substances 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 229910012851 LiCoO 2 Inorganic materials 0.000 claims description 2
- 229910010586 LiFeO 2 Inorganic materials 0.000 claims description 2
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 claims description 2
- 229910015726 LiMn0.3Co0.3Ni0.3O2 Inorganic materials 0.000 claims description 2
- 229910016087 LiMn0.5Ni0.5O2 Inorganic materials 0.000 claims description 2
- 229910013716 LiNi Inorganic materials 0.000 claims description 2
- 229910013290 LiNiO 2 Inorganic materials 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 239000002033 PVDF binder Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229910000676 Si alloy Inorganic materials 0.000 claims description 2
- 229910001128 Sn alloy Inorganic materials 0.000 claims description 2
- JDZCKJOXGCMJGS-UHFFFAOYSA-N [Li].[S] Chemical compound [Li].[S] JDZCKJOXGCMJGS-UHFFFAOYSA-N 0.000 claims description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910003481 amorphous carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 238000010894 electron beam technology Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 229910021450 lithium metal oxide Inorganic materials 0.000 claims description 2
- HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical compound [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920001748 polybutylene Polymers 0.000 claims description 2
- 229920005597 polymer membrane Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims 2
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 2
- 150000002892 organic cations Chemical class 0.000 claims 2
- OPUHLOIVOZBBNY-UHFFFAOYSA-M lithium carbonic acid fluoride Chemical compound C(O)(O)=O.[Li+].[F-] OPUHLOIVOZBBNY-UHFFFAOYSA-M 0.000 claims 1
- 150000008301 phosphite esters Chemical class 0.000 claims 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003063 flame retardant Substances 0.000 abstract description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 2
- IOTNLSAKNNGZGC-UHFFFAOYSA-N 3-ethenyloxolan-2-one Chemical compound C=CC1CCOC1=O IOTNLSAKNNGZGC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- QFKRIEXRNYKNFD-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethyl hydrogen carbonate Chemical compound OC(=O)OC(F)(F)C(F)(F)F QFKRIEXRNYKNFD-UHFFFAOYSA-N 0.000 description 1
- PILOAHJGFSXUAY-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropyl methyl carbonate Chemical compound COC(=O)OC(F)(F)C(F)(F)C(F)(F)F PILOAHJGFSXUAY-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical group N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- ZCYXFITUYVYSJW-UHFFFAOYSA-N 1-ethenylisoquinoline Chemical compound C1=CC=C2C(C=C)=NC=CC2=C1 ZCYXFITUYVYSJW-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 description 1
- NSGMIQOUTRJDRS-UHFFFAOYSA-N 1-methoxy-2-(2-phenylphenyl)benzene Chemical group COC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 NSGMIQOUTRJDRS-UHFFFAOYSA-N 0.000 description 1
- GUBGUXGKVFBTRZ-UHFFFAOYSA-N 1-methoxy-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2OC GUBGUXGKVFBTRZ-UHFFFAOYSA-N 0.000 description 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- DKQPXAWBVGCNHG-UHFFFAOYSA-N 2,2,4,4,6,6-hexafluoro-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound FP1(F)=NP(F)(F)=NP(F)(F)=N1 DKQPXAWBVGCNHG-UHFFFAOYSA-N 0.000 description 1
- UQFHLJKWYIJISA-UHFFFAOYSA-N 2,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C)=N1 UQFHLJKWYIJISA-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- ULNGGKGFBUZKRY-UHFFFAOYSA-N 2-(4-fluorophenyl)-4,6-dimethoxy-1,3,5-triazine Chemical compound FC1=CC=C(C=C1)C1=NC(=NC(=N1)OC)OC ULNGGKGFBUZKRY-UHFFFAOYSA-N 0.000 description 1
- UFNYTHZFYPQOIX-UHFFFAOYSA-N 2-(oxetan-2-yl)ethanamine Chemical compound NCCC1CCO1 UFNYTHZFYPQOIX-UHFFFAOYSA-N 0.000 description 1
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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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
- H01M10/056—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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/04—Hybrid capacitors
- H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/60—Liquid electrolytes characterised by the solvent
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/64—Liquid electrolytes characterised by additives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- 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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- 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
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Abstract
本发明涉及包含三嗪部分的含磷阻燃材料和含有所述材料的用于电化学电池的电解质。
Description
相关申请的交叉引用
本申请要求于2017年7月17日提交的美国临时专利申请序列号62/533270的申请日期的权益,其特此通过引用以其整体并入。
技术领域
本公开涉及包含三嗪部分的含磷阻燃材料、含有所述材料的电解质和含有所述电解质的电能存储装置。
背景技术
室温离子液体(IL)的合成和电化学分析的最新进展已经确定了此独特类别的材料作为用于下一代锂离子电池的电解质的前景。IL是具有低于100℃的熔点的有机盐并且通常由大体积阳离子和无机阴离子组成。大阳离子尺寸允许对电荷进行移位和筛选,使得晶格能减少并且因此使得熔点或玻璃化转变温度减小。IL具有独特的物理化学特性,诸如可忽略的蒸汽压力、耐燃性、良好室温离子导电率、宽电化学窗口和有利的化学和热稳定性。这些特性对于提供用于锂电池的基于IL的电解质而言是希望的。
然而,仍然存在安全挑战,如锂离子电池在滥用条件下或甚至正常条件下的可燃性。Zhang等人的美国专利号8,697,291教导了含有基于三嗪的添加剂的电解质组合物的用途,但未提及离子液体的用途。因此,需要将具有阻燃能力的新型离子液体并入到锂离子电池中。
发明内容
本公开涉及包含三嗪部分的含磷阻燃材料和用于电化学电池的含有这些阻燃材料的电解质。
根据本公开的一个方面,提供了一种用于电能存储装置的电解质,该电解质包括非质子有机溶剂、碱金属盐、添加剂和含有至少一个三嗪部分的离子液体化合物。
根据本公开的另一个方面,提供了一种在电能存储装置中的电解质,该电解质包括非质子有机溶剂、碱金属盐、添加剂和含有磷的包含三嗪部分的阻燃材料,其中有机溶剂是开链或环状碳酸酯、羧酸酯、腈、醚、砜、亚砜、酮、内酯、二氧戊环、甘醇二甲醚、冠醚、硅氧烷、磷酸酯、磷酸盐、亚磷酸酯、单磷腈或聚磷腈或其混合物。
根据本公开的另一个方面,提供了一种在电能存储装置中的电解质,该电解质包括非质子有机溶剂、碱金属盐、添加剂和包含三嗪部分的含磷阻燃材料,其中碱金属盐的阳离子是锂、钠、铝或镁。
根据本公开的另一个方面,提供了一种在电能存储装置中的电解质,该电解质包括非质子有机溶剂、碱金属盐、添加剂和包含三嗪部分的含磷阻燃材料,其中添加剂包含含硫化合物、含磷化合物、含硼化合物、含硅化合物、含有至少一个不饱和碳-碳键的化合物、羧酸酐或其混合物。
在阅读以下详细描述和所附权利要求后,本公开的这些和其他方面将变得显而易见。
附图说明
附图是比较实例0电解质与包含改性三嗪化合物的电解质(实例1)之间的室温循环寿命比较。
具体实施方式
本公开涉及一种离子液体化合物,其包括至少一种阳离子和至少一种阴离子,其中该至少一种阳离子共价键合至至少一个三嗪部分。
在一个实施方案中,电能存储装置电解质包括:a)非质子有机溶剂体系;b)碱金属盐;c)添加剂;和d)包含三嗪部分的含磷阻燃材料。
在一个实施方案中,改性阻燃材料包含根据下式的三嗪部分:
其中:
R是苯环,其中环上的至少一个氢原子被卤素、烷基、烷氧基、甲硅烷基、酰胺、亚砜基团、全氟化烷基、硅烷、亚砜、偶氮、醚或硫醚基团或其组合取代;
Q是烯基、烷基甲硅氧基、甲硅烷基、硫醚基、亚砜、偶氮、氨基或硅烷基;并且
并且X是:(a)连接子,其包括C1-C8烷基、烯基、炔基、烷氧基、酯、羰基、苯基、硫醚基、亚砜、偶氮基或芳基,其中这些中的任何碳或氢原子任选地被卤化物进一步取代;(b)O、S、N或C;或者(c)附接至连接子的O、S、N或C。
在一个实施方案中,改性阻燃材料以电解质的约0.01重量%至约50重量%的量存在。
在一个实施方案中,电解质包括锂盐。可以使用各种锂盐,包括例如Li[CF3CO2];Li[C2F5CO2];Li[ClO4];Li[BF4];Li[AsF6];Li[PF6];Li[PF2(C2O4)2];Li[PF4C2O4];Li[CF3SO3];Li[N(CP3SO2)2];Li[C(CF3SO2)3];Li[N(SO2C2F5)2];烷基氟磷酸锂;Li[B(C2O4)2];Li[BF2C2O4];Li2[B12Z12-jHj];Li2[B10X10-j'Hj’];或其任何两种或更多种的混合物,其中Z在每次出现时独立地是卤素,j是0至12的整数,并且j’是1至10的整数。
在本发明电解质的一些应用(如用于锂离子电池的制品)中,非质子溶剂与本发明包含三嗪部分的含磷阻燃材料组合以降低电解质的粘度并增加其电导率。最适当的非质子溶剂缺乏可交换质子,包括环状碳酸酯、线性碳酸酯、磷酸酯、低聚醚取代的硅氧烷/硅烷、环状醚、链醚、内酯化合物、链酯、腈化合物、酰胺化合物、砜化合物、硅氧烷、磷酸酯、磷酸盐、亚磷酸酯、单磷腈或聚磷腈等。这些溶剂可以单独使用,或者其中至少两种混合使用。用于形成电解质体系的非质子溶剂或载体的实例包括但不限于碳酸二甲酯、碳酸乙基甲酯、碳酸二乙酯、碳酸甲基丙基酯、碳酸乙基丙基酯、碳酸二丙酯、碳酸双(三氟乙基)酯、碳酸双(五氟丙基)酯、碳酸三氟乙基甲酯、碳酸五氟乙基甲酯、碳酸七氟丙基甲酯、碳酸全氟丁基甲酯、碳酸三氟乙基乙基酯、碳酸五氟乙基乙基酯、碳酸七氟丙基乙基酯,碳酸全氟丁基乙基酯等,氟化低聚物,丙酸甲酯、丙酸乙酯、丙酸丁酯、二甲氧基乙烷、三甘醇二甲醚、碳酸二甲基亚乙烯基酯、四甘醇、二甲醚、聚乙二醇、磷酸三苯酯、磷酸三丁酯、六氟环三磷腈、2-乙氧基-2,4,4,6,6-五氟-1,3,5,2-5,4-5,6-5三氮杂三膦、亚磷酸三苯酯、环丁砜、二甲基亚砜、乙基甲基砜、乙基乙烯基砜、烯丙基甲基砜、二乙烯基砜、氟苯甲基甲基砜和γ-丁内酯。
在一些实施方案中,电解质还包括添加剂以保护电极免受降解。因此,本技术的电解质可以包括添加剂,该添加剂在负电极表面上被还原或聚合以在负电极表面上形成钝化膜。同样,电解质可以包括添加剂,该添加剂可以在正电极表面上被氧化或聚合以在正电极表面上形成钝化膜。另外,电解质可以包括充当水、酸和不希望的金属离子的清除剂的添加剂。在一个实施方案中,本技术的电解质还包括三种类型的添加剂的混合物。
在一个实施方案中,添加剂是取代或未取代的直链、支链或环状烃,包括至少一个氧原子和至少一个芳基、烯基或炔基。由此类添加剂形成的钝化膜也可以由取代的芳基化合物或者取代或未取代的杂芳基化合物形成,其中添加剂包括至少一个氧原子。
代表性添加剂包括乙二醛双(二烯丙基缩醛)、四(乙二醇)二乙烯基醚、1,3,5-三烯丙基-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、1,3,5,7-四乙烯基-1,3,5,7-四甲基环四硅氧烷、2,4,6-三烯丙氧基-1,3,5-三嗪、1,3,5-三丙烯酰基六氢-1,3,5-三嗪、糠酸1,2-二乙烯基酯、碳酸1,3-丁二烯酯、1-乙烯基氮杂环丁烷-2-酮、1-乙烯基氮丙啶-2-酮、1-乙烯基哌啶-2-酮、1-乙烯基吡咯烷酮-2-酮、2,4-二乙烯基-1,3-二噁烷、2-氨基-3-乙烯基环己酮、2-氨基-3-乙烯基环丙烷酮、2-氨基-4-乙烯基环丁酮、2-氨基-5-乙烯基环戊酮、2-芳氧基-环丙烷酮、2-乙烯基-[1,2]氧氮杂环丁烷、2-乙烯基氨基环己醇、2-乙烯基氨基环丙烷酮、2-乙烯基氧杂环丁烷、2-乙烯基氧基-环丙烷酮、3-(N-乙烯基氨基)环己酮、糠酸3,5-二乙烯基酯、3-乙烯基氮杂环丁烷-2-酮、3-乙烯基氮丙啶-2-酮、3-乙烯基环丁酮、3-乙烯基环戊酮、3-乙烯基氧杂氮杂环丙烷、3-乙烯基氧杂环丁烷、3-乙烯基吡咯烷-2-酮、2-乙烯基-1,3-二氧戊环、丙烯醛二乙缩醛、丙烯醛二甲缩醛、4,4-二乙烯基-3-二氧戊环-2-酮、4-乙烯基四氢吡喃、5-乙烯基哌啶-3-酮、烯丙基缩水甘油醚、丁二烯一氧化物、丁基乙烯基醚、二氢吡喃-3-酮、碳酸二乙烯基丁基酯、碳酸二乙烯基酯、巴豆酸二乙烯基酯、二乙烯基醚、碳酸二乙烯基乙烯酯、硅酸二乙烯基乙烯酯、硫酸二乙烯基乙烯酯、亚硫酸二乙烯基乙烯酯、二乙烯基甲氧基吡嗪、磷酸二乙烯基甲酯、碳酸二乙烯基丙烯酯、磷酸乙酯、甲氧基-邻-三联苯、磷酸甲酯、氧杂环丁烷-2-基乙烯基胺、环氧乙烷基乙烯基胺、碳酸乙烯基酯、巴豆酸乙烯基酯、乙烯基环戊酮、2-糠酸乙烯基乙酯(vinyl ethyl-2-furoate)、碳酸乙烯基乙烯酯、硅酸乙烯基乙烯酯、硫酸乙烯基乙烯酯、亚硫酸乙烯基乙烯酯、甲基丙烯酸乙烯酯、磷酸乙烯酯、2-糠酸乙烯酯、乙烯基环丙烷酮、乙烯基环氧乙烷、β-乙烯基-γ-丁内酯或者其任何两种或更多种的混合物。在一些实施方案中,添加剂可以是被氟、烷氧基、烯氧基、芳氧基、甲氧基、烯丙氧基或其组合取代的环三磷腈。例如,添加剂可以是(二乙烯基)-(甲氧基)(三氟)环三磷腈、(三乙烯基)(二氟)(甲氧基)环三磷腈、(乙烯基)(甲氧基)(四氟)环三磷腈、(芳氧基)(四氟)(甲氧基)环三磷腈或(二芳氧基)(三氟)(甲氧基)环三磷腈化合物或者两种或更多种此类化合物的混合物。在一些实施方案中,添加剂是碳酸乙烯基亚乙酯、碳酸乙烯基酯或1,2-二苯醚,或者任何两种或更多种此类化合物的混合物。
其他代表性添加剂包括具有苯基、萘基、蒽基、吡咯基、恶唑基、呋喃基、吲哚基、咔唑基、咪唑基、噻吩基、氟化碳酸酯、磺内酯、硫化物、酸酐、硅烷、甲硅烷氧基、磷酸盐或亚磷酸酯基团的化合物。例如,添加剂可以是苯基三氟甲基硫醚、碳酸氟亚乙酯、1,3,2-二氧杂硫杂环戊烷2,2-二氧化物、1-丙烯1,3-磺内酯、1,3-丙磺酸内酯、1,3-二氧戊环-2-酮、4-[(2,2,2-三氟乙氧基)甲基]、1,3-二氧戊环-2-酮、4-[[2,2,2-三氟-1-(三氟甲基)乙氧基]甲基]-、碳酸甲基2,2,2-三氟乙酯、九氟己基三乙氧基硅烷、八甲基三硅氧烷、甲基三(三甲基甲硅烷氧基)硅烷、四(三甲基甲硅烷氧基)硅烷、(十三氟-1,1,2,2-四氢辛基)三乙氧基硅烷、三(1H.1H-七氟丁基)磷酸酯、3,3,3-三氟丙基三(3,3,3-三氟丙基二甲基甲硅烷氧基)硅烷、(3,3,3-三氟丙基)三甲氧基硅烷、三甲基甲硅烷基三氟甲磺酸盐、三(三甲基甲硅烷基)硼酸酯、磷酸三丙酯,双(三甲基甲硅烷基甲基)苄胺、苯基三(三甲基甲硅烷氧基)硅烷、1,3-双(三氟丙基)四甲基二硅氧烷、磷酸三苯酯、磷酸三(三甲基甲硅烷基)酯、磷酸三(1H.1H,5H-八氟戊基)酯、亚磷酸三苯酯、三月桂基三硫代亚磷酸酯、亚磷酸三(2,4-二叔丁基苯基)酯、亚磷酸三对甲苯酯、磷酸三(2,2,3,3,3-五氟丙基)酯、琥珀酸酐、1,5,2,4-二氧杂二噻烷2,2,4,4-四氧化物、三丙基三硫代磷酸酯、芳氧基吡咯、芳氧基硫酸亚乙基酯、芳氧基吡嗪、芳氧基咔唑三乙烯基磷酸酯、芳氧基-2-糠酸乙酯、芳氧基-邻-三联苯、芳氧基-哒嗪、丁基-芳氧基-醚、二乙烯基二苯醚、(四氢呋喃-2-基)乙烯基胺、二乙烯基甲氧基联吡啶、甲氧基-4-乙烯基联苯、乙烯基甲氧基咔唑、乙烯基甲氧基哌啶、乙烯基甲氧基吡嗪、碳酸乙烯基甲酯-烯丙基苯甲醚、乙烯基哒嗪、1-二乙烯基咪唑、3-乙烯基四氢呋喃、二乙烯基呋喃、二乙烯基甲氧基呋喃、二乙烯基吡嗪、乙烯基甲氧基咪唑、乙烯基甲氧基吡咯、乙烯基四氢呋喃、2,4-二乙烯基异恶唑、3,4二乙烯基-1-甲基吡咯、芳氧基氧杂环丁烷、芳氧基碳酸苯酯、芳氧基哌啶、芳氧基-四氢呋喃、2-芳基-环丙酮、2-二芳氧基-糠酸酯、4-烯丙基苯甲醚、芳氧基-咔唑、芳氧基-2-糠酸酯、芳氧基-巴豆酸酯、芳氧基-环丁烷、芳氧基-环戊酮、芳氧基-环丙烷酮、芳氧基-环磷腈、芳氧基-硅酸乙烯酯、芳氧基-硫酸乙烯酯、芳氧基-亚硫酸乙烯酯、芳氧基-咪唑、芳氧基-甲基丙烯酸酯、芳氧基磷酸酯、芳氧基吡咯、芳氧基喹啉、二芳氧基环三磷腈、碳酸二芳氧基乙烯酯、二芳氧基呋喃、二芳氧基甲基磷酸酯、碳酸二芳氧基丁酯、二芳氧基巴豆酸酯、二芳氧基二苯醚、硅酸二芳氧基乙酯、硅酸二芳氧基乙烯酯、亚硫酸二芳氧基乙烯酯、碳酸二芳氧基乙烯酯、碳酸二芳氧基丙烯酯、碳酸二苯酯、硅酸二苯基二芳氧基酯、硅酸二苯二乙烯酯、二苯醚、硅酸二苯酯、二乙烯基甲氧基二苯醚、碳酸二乙烯基苯酯、甲氧基咔唑或2,4-二甲基-6-羟基嘧啶、乙烯基甲氧基喹啉、哒嗪、乙烯基哒嗪、喹啉、乙烯基喹啉、吡啶、乙烯基吡啶、吲哚,乙烯基吲哚、三乙醇胺、1,3-二甲基丁二烯、丁二烯、碳酸乙烯基乙烯酯、碳酸乙烯基酯、咪唑、乙烯基咪唑、哌啶、乙烯基哌啶、嘧啶、乙烯基嘧啶、吡嗪、乙烯基吡嗪、异喹啉、乙烯基异喹啉、喹喔啉、乙烯基喹喔啉、联苯、1,2-二苯醚、1,2-二苯基乙烷、邻苯基、N-甲基吡咯、萘或者任何两种或更多种此类化合物的混合物。
在一个实施方案中,本技术的电解质包括非质子凝胶聚合物载体/溶剂。合适的凝胶聚合物载体/溶剂包括聚醚、聚氧化乙烯、聚酰亚胺、聚磷腈、聚丙烯腈、聚硅氧烷、聚醚接枝聚硅氧烷、前述物质的衍生物、前述物质的共聚物、前述物质的交联和网络结构、前述物质的共混物等,其中加入合适的离子电解质盐。其他凝胶-聚合物载体/溶剂包括由衍生自聚环氧丙烷、聚硅氧烷、磺化聚酰亚胺、全氟化膜(Nafion树脂)、二乙烯基聚乙二醇、聚乙二醇-双-(丙烯酸甲酯)、聚乙二醇-双(甲基丙烯酸甲酯)、前述物质的衍生物、前述物质的共聚物以及前述物质的交联和网络结构的聚合物基质制备的那些。
含有该盐的电解质溶液的电导率和有机溶剂中的溶解度较高并且适合用作用于电化学装置的电解质溶液。电化学装置的实例是双电层电容器、二次电池、颜料敏化型太阳能电池、电致变色装置和电容器(condensers),并且此列表不是限制性的。特别适合作为的电化学装置是双电层电容器和二次电池,如锂离子电池。
在另一个方面中,提供了一种电化学装置,其包括阴极、阳极和电解质,该电解质包括如本文所述的含有三嗪的改性离子液体。在一个实施方案中,电化学装置是锂二次电池。在一个实施方案中,二次电池是锂电池、锂离子电池、锂-硫电池、锂-空气电池、钠离子电池或镁电池。在一个实施方案中,电化学装置是电化学电池,如电容器。在一个实施方案中,电容器是不对称电容器或超级电容器。在一个实施方案中,电化学电池是原电池。在一个实施方案中,原电池是锂/MnO2电池或Li/聚(单氟化碳)电池。在一个实施方案中,电化学电池是太阳能电池。
合适的阴极包括但不限于锂金属氧化物、尖晶石、橄榄石、碳包覆橄榄石、LiFePO4、LiCoO2、LiNiO2、LiNi1xCoyMetzO2、LiMn0.5Ni0.5O2、LiMn0.3Co0.3Ni0.3O2、LiMn2O4、LiFeO2、Li1+x'NiαMnβCoγMet'δO2-z'Fz'、An'B2(XO4)3(NASICON)、氧化钒、过氧化锂、硫、多硫化物、一氟化碳锂(也称为LiCFx)或其任何两种或更多种的混合物,其中Met是Al、Mg、Ti、B、Ga、Si、Mn或Co;Met'是Mg、Zn、Al、Ga、B、Zr或Ti;A是Li、Ag、Cu、Na、Mn、Fe、Co、Ni、Cu或Zn;B是Ti、V、Cr、Fe或Zr;X是P、S、Si、W或Mo;并且其中0≤x≤0.3、0≤y≤0.5、0≤z≤0.5、0≤x'≤0.4、0≤α≤1、0≤β≤1、0≤γ≤1、0≤δ≤0.4、0≤z'≤0.4且0≤h'≤3。根据一些实施方案,尖晶石是具有式Li1+xMn2-zMet”'yO4-mX'n的尖晶石氧化锰,其中Met”'是Al、Mg、Ti、B、Ga、Si、Ni或Co;X'是S或F;并且其中0≤x≤0.3、0≤y≤0.5、0≤z≤0.5、0≤m≤0.5且0≤n≤0.5。在一个实施方案中,橄榄石具有式Li1+xFe1zMet”yPO4-mX'n,其中Met”是Al、Mg、Ti、B、Ga、Si、Ni、Mn或Co;X'是S或F;并且其中0≤x≤0.3、0 0≤y≤0.5、0≤z≤0.5、0≤m≤0.5且0≤n≤0.5。
合适的阳极包括如锂金属、石墨材料、无定形碳、Li4Ti5O12、锡合金、硅合金、金属间化合物或者任何两种或更多种此类材料的混合物。合适的石墨材料包括天然石墨、人造石墨、石墨化中间相碳微珠(MCMB)和石墨纤维,以及任何无定形碳材料。在一些实施方案中,阳极和阴极通过多孔分隔器彼此分离。
用于锂电池的分隔器通常是微孔聚合物膜。用于形成膜的聚合物的实例包括:尼龙、纤维素、硝化纤维素、聚砜、聚丙烯腈、聚偏二氟乙烯、聚丙烯、聚乙烯、聚丁烯或者任何两种或更多种此类聚合物的共聚物或共混物。在一些情况下,分隔器是电子束处理的微孔聚烯烃分隔器。电子处理可以提高分隔器的变形温度,并且可以相应地提高分隔器的高温性能。另外或可选地,分隔器可以是关闭的分隔器。关闭的分隔器可以具有高于约130℃的触发温度,以允许电化学电池在高达约130℃的温度下运行。
将参考以下具体实例进一步说明本公开。应理解,这些实例是以说明的方式给出,并且不意在限制本公开或之后跟随的权利要求书。
实例1 4-氟苯基-二甲氧基三嗪的合成
向配备磁性搅拌棒的20mL小瓶中将4-氟苯酚溶解于DCM(10mL)中。通过移液管添加三乙胺并且将混合物搅拌10min。
在室温下搅拌的同时,将2-氯-4,6-二甲氧基-1,3,5-三嗪部分溶解于DCM(5mL)中并且添加。未观察到温度增加。将混合物在44℃下加热1h。混合物缓慢变成无色并且变得混浊并且快速形成白色固体ppt(三乙胺-HCl)。使混合物缓慢返回室温并将其搅拌1小时。
添加DI水(2x20mL)并且将有机相提取到DCM(10mL)中,分离,经MgSO4干燥并且通过旋转蒸发汽提溶剂。产率:无色油,2.4g(99%)。
H1NMR:(CDCl3)δ ppm 7.14(m,2H),7.10(t,2H),4.00(s,6H)。
F19NMR:(CDCl3)δ ppm-116.73(s)。存在未反应的氟苯酚。
油在静置时结晶成白色固体并且在试剂醇中形成浆液并且通过真空过滤收集。产率:白色固体,1.1g(50%)。H1NMR:(CDCl3)δppm 7.14(m,2H),7.08(t,2H),4.00(s,6H)。F19NMR:(CDCl3)δ ppm-116.74(s)。
实例2三(4-氟苯基)氰尿酸酯的合成
<u>试剂</u> | <u>MW</u> | <u>当量</u> | <u>摩尔</u> | <u>质量(g)</u> | <u>密度</u> | <u>体积(mL)</u> | <u>浓度</u> | <u>产率(计算值)</u> |
4-氟苯酚 | 112.10 | 1.00 | 0.009 | 1.0 | #DIV/0! | |||
三聚氯氰 | 184.41 | 0.33 | 0.003 | 0.54 | #DIV/0! | |||
DCM | 5.1 | 1.326 | 3.9 | 30% | ||||
三乙胺 | 101.19 | 1.00 | 0.009 | 0.9 | 0.726 | 1.2 | ||
(4氟苯酚)3-氰尿酸酯 | 411.21 | 1.00 | 1.2 | |||||
三乙胺-HCI | 137.65 | 1.00 | 0.009 | 1.2 |
向配备磁性搅拌棒的20mL小瓶中将4-氟苯酚溶解于DCM(10mL)中。通过移液管添加三乙胺并且将混合物搅拌10min。
在室温下搅拌的同时,通过移液管缓慢添加三聚氯氰于DCM(5mL)中的溶液。观察到轻度温升,并且混合物快速变得混浊并且形成白色固体ppt(三乙胺-HCl)。使黄色混合物缓慢返回室温并将其搅拌1h。
添加DI水(20mL)并且将有机相提取到DCM(20mL)中,分离,经MgSO4干燥并且通过旋转蒸发汽提溶剂。产率:黄色固体,1.2g(99%)。
使固体在试剂醇中形成浆液并且通过真空过滤来收集。产率:白色固体,0.4g(33%)。滤液保持黄色并且通过旋转蒸发汽提成油。
H1NMR:(CDCl3)δ ppm 7.08(m,2H),7.04(t,2H)。F19NMR:(CDCl3)δppm-116.23(s)。
实例3:
通过将所有电解质组分混合在小瓶中并搅拌24小时以确保盐完全溶解,在干燥的充满氩气的手套箱中制备电解质制剂。将三嗪改性的离子液体化合物作为添加剂加入到基础电解质制剂中,该制剂包含碳酸乙烯酯“EC”和碳酸乙基甲基酯“EMC”的重量比3:7的混合物,其中溶解有1M六氟磷酸锂“LiPF6”。
所制备的电解质制剂概述于表A中。
表A.电解质制剂。
<u>试剂</u> | <u>MW</u> | <u>当量</u> | <u>摩尔</u> | <u>质量(q)</u> | <u>密度</u> | <u>体积(mL)</u> | <u>浓度</u> | <u>产率(计算值)</u> |
4-氟酚 | 110.10 | 1.00 | 0.009 | 1.0 | #DIV/0! | |||
2-氟-4,6-二甲氧基-1,3,5-三嗪 | 175.57 | 1.00 | 0.009 | 1.59 | #DIV/0! | |||
DCM | 5.2 | 1.326 | 3.9 | 50% | ||||
三乙胺 | 101.19 | 1.00 | 0.009 | 0.9 | 0.726 | 1.3 | ||
4-氟苯基-4,6-二甲氧基-1,3,5-三嗪 | 249.17 | 1.00 | 2.3 | |||||
三乙胺 | 137.65 | 1.00 | 0.009 | 1.3 |
实例4
将所制备的电解质制剂用作200mAh 403520 Li离子聚合物袋电池中的电解质,所述袋电池包含锂NMC622阴极活性材料和石墨作为阳极活性材料。将每种电解质都填充在三个电池中。在真空密封和测试之前,在每个电池中加入0.9ml电解质制剂,并使其在电池中浸泡1小时。然后将电池充电至4.4V,并以C/10的速率放电至3.0V以用于形成,并且然后在室温下通过1C放电和充电速率循环。此循环测试的结果概述于附图中。在附图中,已显示电解质1表明在循环寿命期间容量保持率优于比较实例0电解质。
尽管本文已经详细示出和描述了优选实施方案,相关领域技术人员显而易见的是可以在不脱离本公开的精神的情况下进行各种修改、添加、替换等,并且因此,这些修改、添加、替换等被认为在如以下权利要求书中定义的本公开的范围内。
Claims (26)
2.根据权利要求1所述的电解质,其中所述硅烷基为甲硅烷基。
3.如权利要求1所述的电解质,其中所述非质子有机溶剂包括开链或环状碳酸酯、羧酸酯、亚硝酸酯、醚、砜、酮、内酯、二氧戊环、硅氧烷、磷酸酯、亚磷酸酯、单磷腈或聚磷腈、或其混合物。
4.如权利要求1所述的电解质,其中所述碱金属盐的阳离子包括锂离子或钠离子。
5.如权利要求1所述的电解质,其中所述添加剂包括含硫化合物、含磷化合物、含硼化合物、含硅化合物、含氟化合物、含氮化合物、含有至少一个不饱和碳-碳键的化合物、羧酸酐、或其混合物。
6.如权利要求1所述的电解质,其中所述添加剂在所述电解质中的浓度为0.1重量%至5重量%。
7.如权利要求1所述的电解质,其还包含离子液体。
8.如权利要求7所述的电解质,其中所述离子液体包含有机阳离子,所述有机阳离子包含N-烷基-N-烷基-吡咯烷鎓、N-烷基-N-烷基-吡啶鎓、N-烷基-N-烷基-锍、N-烷基-N-烷基-铵或N-烷基-N-烷基-哌啶鎓。
9.如权利要求7所述的电解质,其中所述离子液体包含阴离子,所述阴离子包含四氟硼酸盐、六氟磷酸盐、双(三氟甲基磺酰基)酰亚胺、双(五氟乙基磺酰基)酰亚胺或三氟乙酸盐。
10.如权利要求1所述的电解质,其中所述碱金属盐替换为铝盐或镁盐。
11.一种电能存储装置,其包括:
阴极;
阳极;和
根据权利要求1所述的电解质。
12.如权利要求11所述的装置,其中所述阴极包括锂金属氧化物、尖晶石、橄榄石、碳包覆橄榄石、LiFePO4、LiCoO2、LiNiO2、LiNi1xCoyMetzO2、LiMn0.5Ni0.5O2、LiMn0.3Co0.3Ni0.3O2、LiMn2O4、LiFeO2、Li1+x'NiαMnβCoγMet'δO2-z'Fz'、An'B2(XO4)3、钒氧化物、过氧化锂、硫、多硫化物、一氟化碳锂或其任何两种或更多种的混合物,其中Met是Al、Mg、Ti、B、Ga、Si、Mn或Co;Met'是Mg、Zn、Al、Ga、B、Zr或Ti;A是Li、Ag、Cu、Na、Mn、Fe、Co、Ni、Cu或Zn;B是Ti、V、Cr、Fe或Zr;X是P、S、Si、W或Mo;并且其中0≤x≤0.3、0≤y≤0.5、0≤z≤0.5、0≤x'≤0.4、0≤α≤1、0≤β≤1、0≤γ≤1、0≤δ≤0.4、0≤z'≤0.4且0≤n'≤3。
13.如权利要求11所述的装置,其中所述阳极包括金属间化合物。
14.如权利要求11所述的装置,其中所述阳极包括锂金属、石墨材料、无定形碳、Li4Ti5O12、锡合金、硅合金或其混合物。
15.如权利要求11所述的装置,其中所述装置包括电化学电池、电容器或太阳能电池。
16.如权利要求15所述的装置,其中所述电化学电池包括锂电池、钠离子电池和镁电池。
17.如权利要求15所述的装置,其中所述电化学电池包括锂离子电池、锂-硫电池、锂-空气电池、锂/MnO2电池和Li/聚(单氟化碳)电池。
18.如权利要求11所述的装置,其还包括将所述阳极和所述阴极彼此分离的多孔分隔器。
19.如权利要求18所述的装置,其中所述多孔分隔器包括电子束处理的微孔聚烯烃分隔器或微孔聚合物膜,所述微孔聚合物膜包括尼龙、纤维素、聚砜、聚丙烯腈、聚偏二氟乙烯、聚丙烯、聚乙烯、聚丁烯或者任何两种或更多种上述聚合物的共聚物或共混物。
20.如权利要求11所述的装置,其中所述非质子有机溶剂包括开链或环状碳酸酯、羧酸酯、亚硝酸酯、醚、砜、酮、内酯、二氧戊环、硅氧烷、磷酸酯、亚磷酸酯、单磷腈或聚磷腈、或其混合物。
21.如权利要求11所述的装置,其中所述碱金属盐的阳离子包括锂离子或钠离子。
22.如权利要求11所述的装置,其中所述添加剂包括含硫化合物、含磷化合物、含硼化合物、含硅化合物、含氟化合物、含氮化合物、含有至少一个不饱和碳-碳键的化合物、羧酸酐、或其混合物。
23.如权利要求11所述的装置,其还包含离子液体。
24.如权利要求23所述的装置,其中所述离子液体包含有机阳离子,所述有机阳离子包含N-烷基-N-烷基-吡咯烷鎓、N-烷基-N-烷基-吡啶鎓、N-烷基-N-烷基-锍、N-烷基-N-烷基-铵或N-烷基-N-烷基-哌啶鎓。
25.如权利要求23所述的装置,其中所述离子液体包含阴离子,所述阴离子包含四氟硼酸盐、六氟磷酸盐、双(三氟甲基磺酰基)酰亚胺、双(五氟乙基磺酰基)酰亚胺或三氟乙酸盐。
26.如权利要求11所述的装置,其中所述碱金属盐替换为铝盐或镁盐。
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