CN110299562A - A kind of new lithium salts additive and its non-aqueous electrolyte for lithium ion cell - Google Patents
A kind of new lithium salts additive and its non-aqueous electrolyte for lithium ion cell Download PDFInfo
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- CN110299562A CN110299562A CN201910644562.2A CN201910644562A CN110299562A CN 110299562 A CN110299562 A CN 110299562A CN 201910644562 A CN201910644562 A CN 201910644562A CN 110299562 A CN110299562 A CN 110299562A
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- Prior art keywords
- lithium
- bicyclic
- lithium salts
- electrolytic solution
- carbonate
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- 239000000654 additive Substances 0.000 title claims abstract description 25
- 229910003002 lithium salt Inorganic materials 0.000 title claims abstract description 24
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 22
- 230000000996 additive effect Effects 0.000 title claims abstract description 17
- 159000000002 lithium salts Chemical class 0.000 title claims abstract description 17
- 239000011255 nonaqueous electrolyte Substances 0.000 title description 4
- 239000003792 electrolyte Substances 0.000 claims abstract description 21
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 18
- -1 lithium salt compound Chemical class 0.000 claims abstract description 15
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000008151 electrolyte solution Substances 0.000 claims description 12
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 4
- GWAOOGWHPITOEY-UHFFFAOYSA-N 1,5,2,4-dioxadithiane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCO1 GWAOOGWHPITOEY-UHFFFAOYSA-N 0.000 claims description 4
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- DGTVXEHQMSJRPE-UHFFFAOYSA-M difluorophosphinate Chemical compound [O-]P(F)(F)=O DGTVXEHQMSJRPE-UHFFFAOYSA-M 0.000 claims description 4
- LKSCJMIATJONBS-UHFFFAOYSA-K trilithium oxalic acid phosphate Chemical class P(=O)([O-])([O-])[O-].[Li+].C(C(=O)O)(=O)O.[Li+].[Li+] LKSCJMIATJONBS-UHFFFAOYSA-K 0.000 claims description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- PAQZWJGSJMLPMG-UHFFFAOYSA-N propylphosphonic anhydride Substances CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- WYWLPUYJUPVXSK-UHFFFAOYSA-N boron;oxalic acid Chemical compound [B].OC(=O)C(O)=O WYWLPUYJUPVXSK-UHFFFAOYSA-N 0.000 claims 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 abstract 1
- 210000000170 cell membrane Anatomy 0.000 abstract 1
- 238000005868 electrolysis reaction Methods 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000007784 solid electrolyte Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- 229910012265 LiPO2F2 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QRMHDYCPNIVCBO-UHFFFAOYSA-N [SH2]=N.[F] Chemical compound [SH2]=N.[F] QRMHDYCPNIVCBO-UHFFFAOYSA-N 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- UFLFSNVZQRNKOX-UHFFFAOYSA-N carbonic acid;ethenyl acetate Chemical compound OC(O)=O.CC(=O)OC=C UFLFSNVZQRNKOX-UHFFFAOYSA-N 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- DGTVXEHQMSJRPE-UHFFFAOYSA-N difluorophosphinic acid Chemical class OP(F)(F)=O DGTVXEHQMSJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
Abstract
The present invention provides a kind of lithium-ion battery electrolytes, and the lithium-ion battery electrolytes are made of organic solvent, lithium salts, new additive agent and other conventional additives.The new additive agent is bicyclic phosphorimide lithium salts or bicyclic thiophosphorimide lithium salt compound shown in structural formula 1.In the present invention, when 1 compound represented of structural formula is as electrolysis additive, reduction potential is higher, therefore can participate in the generation of solid electrolyte film prior to conventional additives and in negative terminal surface, improves the ingredient of interfacial film；Such additive, so as to participate in the generation of anolyte plasma membrane, improves the interface stability of positive electrode since with cyclic phosphate structure, phosphorus oxygen key is easy to happen fracture under high voltages simultaneously.Therefore the introducing of such additive can effectively improve the high-temperature behavior, cryogenic property and cycle performance of lithium ion battery.
Description
[technical field]
The invention belongs to technical field of lithium ion, and in particular to a kind of non-aqueous electrolyte for lithium ion cell and lithium ion
Battery.
[background technique]
In recent years, lithium ion battery is widely used in fields such as 3C number, power vehicle, energy storage devices.In science and technology
Fast-developing today, requirement of the people to lithium ion battery are constantly promoted, for example, the longer service life, higher energy density,
Superior high temperature performance and security performance.Battery material is one of the key technology for promoting performance of lithium ion battery.Its
In, four big main materials one of of the electrolyte as battery, to the cycle performance of battery, high-temperature behavior, cryogenic property and safety
Energy etc. influences great.The exploitation of various lithium-ion battery electrolytes functional form additives has become the research heat of new energy field
Point.
In recent years, the Chinese patent that application publication number is CN106129456B discloses that " a kind of electrolyte is added with function
Agent, long circulating lithium-ion battery electrolytes and lithium ion battery ", the electrolyte functional additive which points out is by carbonic acid Asia
Vinyl acetate, di-oxalate lithium borate and double fluorine sulfimide lithiums (LiFSI), sulfuric acid vinyl ester are compounded with butyl sulfonic acid lactone,
The stability for improving negative terminal surface SEI film reduces the internal resistance of SEI film, prevent in cyclic process SEI film destroyed and
Reacting for electrolyte and cathode is caused, to improve the cycle life of battery.Application publication number is the China of CN104659414B
Patent discloses " lithium secondary battery and nonaqueous electrolytic solution used in it ", and the patent describe difluorophosphates and cyclic annular silicon
Siloxane compound is applied in combination, and has excellent low temperature performance and cycle performance.But these additives itself are usually deposited
It is being difficult to the problems such as taking into account short high temperature performance, high-temperature cycle life and poor safety performance, for example di-oxalate lithium borate exists
The phenomenon that high temperature produces the phenomenon that gas, LiFSI the phenomenon that there are corrosive aluminum foils, difluorophosphate analyse lithium there are low temperature etc..Therefore, anxious
A kind of new additive agent that can take into account high/low temperature and cycle performance need to be developed.
[summary of the invention]
In order to solve above-mentioned relevant issues, the present invention, which provides, a kind of can significantly improve battery high-temperature storage, low temperature discharge
With the lithium-ion battery electrolytes of cycle performance.
The electrolyte contains organic solvent, lithium salts, new additive agent and other additives, and the new additive agent is knot
Bicyclic phosphorimide lithium salts or double thiophosphorimide lithium salt compounds shown in structure formula 1:
R in the new additive agent structure1For oxygen atom or sulphur atom, R2-R9Independently of one another for selected from fluorine atom, alkane
The one or more of saturation or unsaturated alkyl that oxygroup, alkenyloxy group, alkynyloxy group, aryl, itrile group or carbon atom are 1 to 10.
Preferably, 1 compound represented of structural formula is including but not limited to the one or more of following compound:
Bicyclic phosphorimide lithium salt compound 1 is the preparation method is as follows: in methylene chloride by the dissolution of cyclic phosphorochloridate compound
And triethylamine is added, it is then constantly passed through ammonia into solution, there is white depositions generation after completion of the reaction, filters and recrystallizes
After obtain bicyclic phosphorimide compound；Then bicyclic phosphorimide is continued to be dissolved in acetonitrile, then be added lithium carbonate into
Row acid-base reaction obtains bicyclic phosphorimide lithium salt compound 1.Its synthetic route is as follows:
The reaction route of bicyclic phosphorimide lithium salt compound 2 to compound 6 is similar with the synthetic route of compound 1, right
The monocycle phosphoric anhydride compound reaction substrate answered is as follows:
Be fluorinated thiophosphorimide lithium salt compound 7 to compound 9 the preparation method is as follows: first using fluorine gas raw material with
Thio cyclic phosphorochloridate reaction preparation fluorination-thio cyclic phosphorochloridate, then proceedes to prepare sulfur fluoride using the synthetic route of compound 1
For ring phosphorimide lithium compound.Wherein, the synthetic route of compound 7 is as follows:
The organic solvent is including but not limited to ethylene carbonate (EC), methyl ethyl carbonate (EMC), diethyl carbonate
(DEC), one of propene carbonate (PC), propyl propionate (PP), ethyl propionate (EP), fluorinated ethylene carbonate (FEC) or
Multiple combinations.
Preferably, other additives are also contained in the nonaqueous electrolytic solution, other described additives are vinylene carbonate
(VC), 1,3- propane sultone (PS), fluorinated ethylene carbonate (FEC), vinylethylene carbonate (VEC), sulfurous acid Asia second
Ester (ES), methane-disulfonic acid methylene ester (MMDS), adiponitrile, succinonitrile, succinic anhydride, 1- propylphosphonic anhydride, phthalic acid
Acid anhydride, pyridine, quinoline etc..
Preferably, the lithium salts be lithium hexafluoro phosphate, di-oxalate lithium borate, difluorophosphate, the double oxalic acid lithium phosphate of difluoro,
Tetrafluoro oxalic acid lithium phosphate, LiBF4, difluoro lithium sulfimide etc..The preferred concentration of electrolyte lithium salt is 0.5-
1.4mol/L。
The additive of the structural formula 1 accounts for the 0.5%-10% of nonaqueous electrolytic solution gross mass.The new additive agent has
Lower oxidizing potential and higher reduction potential can be respectively formed on positive electrode active materials and negative electrode active material surface
Fine and close solid-state interface film, both interfacial films thermodynamic stability all with higher and ion conductivity, even if in height
Under temperature, high voltage etc. and its aggravating circumstances, the not oxidized decomposition of electrolyte can be protected, guarantees the performance of battery performance.
Meanwhile 1 compound of structural formula is as organolithium salt form additive, with lower interface impedance, it is ensured that lithium ion exists
It is quickly embedded in and deviates from positive and negative anodes, so that battery has excellent cryogenic property.
[specific embodiment]
Below by specific embodiment, the present invention will be described in detail.
Embodiment 1
(1) preparation of electrolyte:
Under argon atmosphere, electrolyte is prepared in the vacuum glove box of moisture content < 1ppm, organic solvent selects carbonic acid
Vinyl acetate/methyl ethyl carbonate/diethyl carbonate=2/5/3 (mass ratio), LiPF6Lithium salt be 1.0mol/L, PS's contains
Amount is the 2% of electrolyte total weight, and the content of difluorophosphate is the 1% of electrolyte total weight, and the bimolecular of weight 1% is added
Phosphoamide lithium salts is named as compound 1, is uniformly mixed, obtains lithium-ion electrolyte of the present invention.
(2) preparation of anode pole piece: by Li [Ni0.5Mn0.2Co0.3]O2: PVDF:SP=95:1:4 is with 1- methyl -2- pyrroles
Alkanone is uniformly mixed, and after the slurry being blended is coated on the two sides of aluminium foil, obtains anode pole piece after drying, roll-in.
(3) preparation of cathode pole piece: by graphite: SP:CMC:SBR=95:1.5:1.0:2.5 is dissolved in aqueous solution, mixing
Uniformly, after being coated on the two sides of copper foil with the slurry being blended, cathode pole piece is obtained after drying, roll-in.
(4) preparation of lithium ion battery: by anode pole piece, cathode pole piece and diaphragm prepared by above-mentioned steps (1)-(3)
Square electric cell is made in a manner of lamination, using polymer packaging, the electrolyte of filling above-mentioned preparation, through works such as chemical conversion, partial volumes
The lithium ion battery that capacity is 2300mAh is made after sequence.
(5) performance of lithium ion battery is tested:
Low temperature discharge test: the battery for first completing partial volume is primary with 1C charge and discharge under normal temperature state, then will with 1C
After battery is fully charged, carries out shelving 4h under the conditions of low temperature is 20 DEG C minus, be discharged with 0.2C.
High temperature storage test: the battery for first completing partial volume is primary with 1C charge and discharge under normal temperature state, then will with 1C
After battery is fully charged, high temperature storage 7d is carried out under the conditions of 70 DEG C, is taken out battery and is carried out 1C electric discharge.
High temperature circulation test: carrying out charge and discharge cycles to battery with 1C/1C at 45 DEG C and test 400 weeks, blanking voltage area
Between be 3.0-4.4V.
Embodiment 2~9 and comparative example 1:
The present embodiment is for illustrating non-aqueous electrolyte for lithium ion cell disclosed by the invention and preparation method thereof, including implementation
Most operating procedure in example 1, the difference is that:
In the preparation step of the nonaqueous electrolytic solution, 1 embodiment 2~9 of table or comparative example 1 is added in the nonaqueous electrolytic solution
The component of shown mass percentage.
Specific test method and embodiment 1 are consistent, and test result is shown in Table 2.
The electrolyte constituent of 1 embodiment and comparative example of table
2 test result of table
The test result of comparative example 1~9 and comparative example 1 in nonaqueous electrolytic solution it is found that add shown in structural formula 1
Bicyclic phosphoamide lithium salt compound or bicyclic phosphorothioate amine lithium salt compound and PS, LiPO2F2In conjunction with lithium can be obviously improved
Low temperature performance, high temperature cyclic performance and the high-temperature storage performance of ion battery.
The foregoing is only a preferred embodiment of the present invention, is not intended to limit the present invention in any form；It is all
The those of ordinary skill of the industry can implement the present invention by the above and swimmingly；But all technologies for being familiar with this profession
Personnel without departing from the scope of the present invention, a little change for being made using disclosed above technology contents,
Modification and the equivalent variations developed, are equivalent embodiment of the invention；Meanwhile all substantial technologicals according to the present invention are to above
The variation, modification and evolution etc. of any equivalent variations made by embodiment still fall within the protection model of technical solution of the present invention
Within enclosing.
Claims (6)
1. a kind of Novel lithium-ion battery electrolyte, it is characterised in that: the electrolyte is by organic solvent, lithium salts, new additive agent
And other additive compositions, which is characterized in that the new additive agent is bicyclic phosphorimide lithium salts or double shown in structural formula 1
Ring thiophosphorimide lithium salt compound.
Wherein R1For oxygen atom or sulphur atom, R2-R9Independently of one another for selected from fluorine atom, alkoxy, alkenyloxy group, alkynyloxy group, virtue
The one or more of saturation or unsaturated alkyl that base, itrile group or carbon atom are 1 to 10.
2. the compound described according to claim 1 is bicyclic phosphorimide lithium salts or double thiophosphorimide lithium salts chemical combination
Object is one or more including but not limited to following compound:
3. nonaqueous electrolytic solution according to claim 1, which is characterized in that bicyclic phosphorimide shown in the structural formula 1
Lithium salts or bicyclic thiophosphorimide lithium salt compound account for the 0.5%-10% of nonaqueous electrolytic solution gross mass.
4. nonaqueous electrolytic solution according to claim 1, it is characterised in that: the organic solvent includes ethylene carbonate
(EC), methyl ethyl carbonate (EMC), diethyl carbonate (DEC), propene carbonate (PC), propyl propionate (PP), ethyl propionate
(EP), one or more combinations of fluorinated ethylene carbonate (FEC) etc..
5. nonaqueous electrolytic solution according to claim 1, which is characterized in that also containing other additions in the nonaqueous electrolytic solution
Agent, other described additives be vinylene carbonate (VC), 1,3- propane sultone (PS), fluorinated ethylene carbonate (FEC),
Vinylethylene carbonate (VEC), glycol sulfite (ES), methane-disulfonic acid methylene ester (MMDS), adiponitrile, succinonitrile, fourth
One or more combinations of dicarboxylic anhydride, 1- propylphosphonic anhydride, phthalic anhydride, pyridine, quinoline etc..
6. nonaqueous electrolytic solution according to claim 1, which is characterized in that the lithium salts is lithium hexafluoro phosphate, double oxalic acid boron
The double oxalic acid lithium phosphates of sour lithium, difluorophosphate, difluoro, tetrafluoro oxalic acid lithium phosphate, LiBF4, difluoro lithium sulfimide etc.
One or more combinations.
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