CN105449283B - A kind of high-voltage lithium ion batteries electrolyte - Google Patents
A kind of high-voltage lithium ion batteries electrolyte Download PDFInfo
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- CN105449283B CN105449283B CN201510995274.3A CN201510995274A CN105449283B CN 105449283 B CN105449283 B CN 105449283B CN 201510995274 A CN201510995274 A CN 201510995274A CN 105449283 B CN105449283 B CN 105449283B
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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
- H01M10/0569—Liquid materials characterised by the solvents
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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
- 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
- H01M10/0568—Liquid materials characterised by the solutes
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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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
The invention discloses a kind of high-voltage lithium ion batteries electrolyte, including organic solvent, lithium salts and lithium salts cosolvent, organic solvent includes the fluoro-alkyl phenylsulfone compounds of 3 nitro of fluoro alkenyl 4 and fluoro dintrile dialkyl ether compound；The high-voltage lithium ion batteries improve lithium battery energy density with electrolysis liquid energy, and stability is good under high voltages, can significantly improve the service life and security performance of lithium battery.
Description
Technical field
The present invention relates to a kind of high-voltage lithium ion batteries liquid electrolyte, belong to technical field of lithium ion.
Background technology
Lithium ion battery because with self-discharge rate is low, memory-less effect, have extended cycle life, energy density is big, operating voltage
High and advantages of environment protection, having become most has one of secondary cell of application prospect, and is widely used in daily life
Every field in work, including the various portable electric appts such as notebook computer, mobile phone, digital camera.However, with various
The fast lifting of portable equipment performance, people propose higher requirement to the capacity and energy density of lithium ion battery.In addition,
With the development of hybrid vehicle (HEV), plug-in hybrid-power automobile (PHEV) and pure electric automobile (EV) in recent years, make
Larger lifting is also required for meet demand for the energy density of the lithium ion battery of its electrical source of power.
It has been proposed that various raising lithium ion battery energy densities method in, except to existing material and battery
Outside production technology is improved, exploitation high voltage (4.5V) positive electrode is considered as a kind of highly efficient approach.Including
LiCoPO4And LiNi0.5Mn1.5O4The high-voltage anode material that discharge voltage inside may be up to more than 4.5V has been developed
Come, show good performance.But the liquid electrolyte of currently used commercial lithium-ion batteries is typically with hexafluoro phosphorus
Sour lithium (LiPF6) be used as conducting salt, with high viscosity, high-k (including：Ethylene carbonate (EC), propene carbonate (PC)
With low viscosity, low-k (including：Dimethyl carbonate (DMC), diethyl carbonate (DEC) or methyl ethyl carbonate
(EMC) mixture of carbonates) is solvent.This electrolyte is when battery system voltage is higher than 4.5V, routine therein
Carbonic ether component is easily decomposed, so as to cause battery performance to decline；And LiPF6Thermostabilization and chemical stability also compare
Difference.Therefore, it is badly in need of developing a kind of liquid electrolyte suitable for high-voltage lithium ion batteries.
The content of the invention
Easily decomposed under high voltages for lithium-ion electrolyte in the prior art, the defects of causing battery performance to decline, this
The purpose of invention is to be that lithium battery energy density, and the good electrolyte of stability under high voltages can be improved by providing one kind,
The electrolysis liquid energy significantly extends lithium battery service life and improves security performance.
In order to realize above-mentioned technical purpose, the invention provides a kind of high-voltage lithium ion batteries electrolyte, include
Solvent, lithium salts and lithium salts cosolvent, described organic solvent include 3- nitro -4,4 '-fluoro dialkyl group diphenyl sulfone class
Compound and fluoro dintrile dialkyl ether compound；
Described fluoro alkenyl 3- nitro -4- fluoro-alkyl phenylsulfone compounds have the structure of formula 1：
Described fluoro dintrile dialkyl ether compound has the structure of formula 2：
CN-R3-O-R4-CN
Formula 2
Wherein,
R1For C1~C5Fluoro-alkyl；
R2For C2~C5Fluoroolefin base；
R3And R4It is various independently selected from C1~C5Fluoroalkane chain group.
The fluoro alkenyl 3- nitros -4- fluoro-alkyls phenylsulfone compounds and fluoro two used in technical scheme
Nitrile dialkyl ether compound all has wider electrochemical window and compared with high anode stability.Fluoro alkenyl 3- nitro -4- fluorine
Benzene radicals and nitro with electrophilic characteristic are introduced in substituted alkyl phenylsulfone compounds, substantially increase its chemically stable
Property；Same fluoro dintrile dialkyl ether compound mainly introduces the extremely strong itrile group of electron-withdrawing power to increase its chemistry in end group
Stability, so as to ensure that the high-voltage stability of electrolyte.Particularly fluoro alkenyl 3- nitros -4- fluoro-alkyl benzene sulfone derivatives chemical combination
Thing has high viscosity, and fluoro dintrile dialkyl ether compound has low viscosity, and both compounding uses form complementation, Ke Yibao
Card electrolyte has suitable viscosity.
The preparation method of the fluoro alkenyl 3- nitro -4- fluoro-alkyl phenylsulfone compounds of the present invention is as follows：
(1) by alkenyl benzene sulfone and monobromo alkyl (Br-R1) in molar ratio 1:1 ratio be mixed and stirred for uniformly, by Fu-
Gram alkylated reaction synthesis alkenyl 4- alkylbenzene sulfones；
(2) by the mixture of (1) products therefrom and the concentrated sulfuric acid and concentrated nitric acid, 4~5h of heat obtains alkenyl altogether at 20~40 DEG C
3- nitro -4- alkylbenzene sulfones.
Alkenyl benzene sulfone that the present invention uses, monobromo alkyl etc. is conventional commercial medicaments.
The preparation method of the fluoro dintrile dialkyl ether compound of the present invention is as follows：
(1) suitable alcohols (R is chosen3OH and R4OH 3~4h) is reacted at 100~140 DEG C can obtain R3-O-R4；
(2) (1) products therefrom is reacted into 2~3h with chlorine molecule under illumination condition and obtains ClR3-O-R4Cl；
(3) alcoholic solution of (2) products therefrom and nitrilation sodium flow back 5~6h at 60~80 DEG C, removing solvent can obtain
To CN-R3-O-R4-CN；
(4) conventional fluoro-reaction is passed through, you can obtain fluoro dintrile dialkyl ether.
The R of use3OH and R4OH is conventional commercially available medicament.
Preferable scheme, organic solvent are made up of following mass percent component：Fluoro alkenyl 3- nitro -4- fluoro-alkyls
Phenylsulfone compounds 25~45%, fluoro dintrile dialkyl ether compound 25~45%, carbonats compound 10~40%.
Preferable scheme, carbonats compound are dimethyl carbonate, diethyl carbonate, fluoro diethyl carbonate, methyl
At least one of ethyl carbonate ester, methyl acetate, methyl formate.
Preferable scheme, the concentration of lithium salts in organic solvent are 1.0~2.0mol/L.
Preferable scheme, lithium salts cosolvent quality are the 1~10% of organic solvent quality.
Preferable scheme, lithium salts LiF, Li2O、Li2O2At least one of.The present invention can pass through LiF, Li2O、
Li2O2Deng replacement routine lithium salts such as lithium hexafluoro phosphate, relatively conventional electrolyte greatly reduces cost.Meanwhile these lithium salts with
Lithium ion anode has good compatibility, can in the anti-film forming of positive electrode surface, further enhance electrolyte high voltage (4.5V~
Stability and good circulating effect under 5.0V).
Preferable scheme, lithium salts cosolvent are pentafluorophenyl group oxalic acid borate, three isopropylidene acetone base borines, three (five fluorine
Phenyl) borine, at least one of three (containing fluoroalkyl) borates；Wherein, it is C containing fluoroalkyl1~C5Fluoro-alkyl.This hair
Lithium salts uses used by bright lithium salts cosolvent mainly coordinates, and can effectively lift the solubility of lithium salts, obtain electrolyte
High conductivity and high-lithium ion transport number, so as to effectively reduce electrode polarization and improve battery coulombic efficiency.
Preferable scheme, electrolyte include dioxalic acid lithium borate and/or difluorine oxalic acid boracic acid lithium cathode film formation additive.This
The introducing of cathode film formation additive in inventive technique scheme, significantly improves the compatibility of electrolyte and negative pole, and ensures
Electrolyte does not react with cathode contact.
Preferable scheme, cathode film formation additive quality are the 1~8% of organic solvent quality.
Compared with the prior art, the advantageous effects that technical solution of the present invention is brought：
1st, the organic solvent that electrolyte of the invention uses includes fluoro alkenyl 3- nitro -4- fluoro-alkyl benzene sulfone derivatives chemical combination
Thing and fluoro dintrile dialkyl ether compound, both there is wider electrochemical window and high anode stability, and can fit
When the viscosity of regulation electrolyte, the stability of electrolyte under high voltages is strengthened, extends service life and the raising of battery
Security performance.
2nd, electrolyte of the invention is good to high-voltage anode material matching, and then the energy for improving lithium ion battery is close
Degree.
3rd, electrolyte of the invention further uses LiF, Li2O、Li2O2Deng electric conducting lithium salt, and lithium salts cosolvent is coordinated to make
With the solubility for improving lithium salts, electrolyte is set to obtain high conductivity and high-lithium ion transport number, so as to effectively reduce electrode polarization
With improvement battery coulombic efficiency；Lithium salts has good compatibility with positive pole, has the filming performance that can be reacted in positive electrode surface, enters
One step strengthens stability and good circulating effect of the electrolyte under 4.5V-5.0V high voltage.
4th, electrolyte raw material of the invention is easy to get, and compound method is simple, meets industrial applications.
Embodiment
Following examples are intended to further illustrate present invention, rather than the model of limitation the claims in the present invention protection
Enclose.
Embodiment 1
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CHFCHF-, R2For-CH=CHCF2-) the 30% of solvent gross mass is accounted for, fluoro two
Nitrile dialkyl ether (wherein R3For-CF2CHF-, R4For-CH2CHFCF2-) the 30% of solvent gross mass is accounted for, dimethyl carbonate accounts for molten
The 40% of agent gross mass, molar concentrations of the lithium salts LiF in nonaqueous solvents are 1.0mol/L, the isopropylidene acetone of lithium salts cosolvent three
The quality of base borine is the 5% of solvent quality, and cathode film formation additive dioxalic acid lithium borate quality is the 5% of solvent quality.
Embodiment 2
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CH2CHFCHF-, R2For-CH=CHCHF-) the 25% of solvent gross mass is accounted for, fluorine
For dintrile dialkyl ether (wherein R3For-CF2CF2-, R4For-CH2CH2CF2-) the 35% of solvent gross mass is accounted for, diethyl carbonate
Account for the 40% of solvent gross mass, molar concentrations of the lithium salts LiF in nonaqueous solvents is 1.0mol/L, the isopropylidene of lithium salts cosolvent three
The quality of acetonyl borine is the 3% of solvent quality, and cathode film formation additive dioxalic acid lithium borate quality is solvent quality
7%.
Embodiment 3
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CHFCF2-, R2For-CH=CHCF2CHF- the 35% of solvent gross mass, fluorine) are accounted for
For dintrile dialkyl ether (wherein R3For-CHFCHFCH2-, R4For-CF2CHFCHF- the 25% of solvent gross mass, methyl second) are accounted for
Base carbonic ester accounts for the 40% of solvent gross mass, lithium salts Li2Molar concentrations of the O in nonaqueous solvents is 1.8mol/L, lithium salts hydrotropy
The quality of agent three (pentafluorophenyl group) borine is the 8% of solvent quality, and cathode film formation additive dioxalic acid lithium borate quality is solvent
The 2% of quality.
Embodiment 4
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CF2CF2-, R2For-CH=CHCF2-) the 45% of solvent gross mass is accounted for, fluoro two
Nitrile dialkyl ether (wherein R3For-CHFCF2-, R4For-CH2CHFCHFCH2-) the 35% of solvent gross mass is accounted for, methyl acetate accounts for
The 20% of solvent gross mass, lithium salts Li2Molar concentrations of the O in nonaqueous solvents is 1.6mol/L, (the phenyl-pentafluoride of lithium salts cosolvent three
Base) borine quality be solvent quality 7%, cathode film formation additive difluorine oxalic acid boracic acid lithium quality be solvent quality 8%.
Embodiment 5
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CHFCF2CH2-, R2For-CH=CHCF2CF2-) the 45% of solvent gross mass is accounted for,
Fluoro dintrile dialkyl ether (wherein R3For-CF2CF2CF2-, R4For-CH2CHFCHF- the 25% of solvent gross mass, fluoro) are accounted for
Diethyl carbonate accounts for the 30% of solvent gross mass, lithium salts Li2O2Molar concentration in nonaqueous solvents is 1.5mol/L, and lithium salts helps
The quality of solvent pentafluorophenyl group oxalic acid borate is the 6% of solvent quality, cathode film formation additive difluorine oxalic acid boracic acid lithium quality
For the 4% of solvent quality.
Embodiment 6
High-voltage lithium-ion battery electrolyte is prepared in glove box, the argon that purity is 99.999% is full of in glove box
Gas, for glove box reclaimed water sub-control system in≤1ppm, temperature is room temperature.In high-voltage lithium-ion battery electrolyte, fluoro alkenyl 3- nitre
Base -4- fluoro-alkyl benzene sulfone derivativeses (wherein R1For-CF2CHFCH2-, R2For-CH=CHCF2-) the 35% of solvent gross mass is accounted for, fluoro
Dintrile dialkyl ether (wherein R3For-CHFCHF-, R4For-CHFCHF-) the 20% of solvent gross mass is accounted for, methyl formate accounts for solvent
The 45% of gross mass, lithium salts Li2O2Molar concentration in nonaqueous solvents is 1.0mol/L, and lithium salts cosolvent three (contains fluoroalkyl)
(wherein alkyl is-CH to borate2-) quality be solvent quality 2%, cathode film formation additive difluorine oxalic acid boracic acid lithium quality
For the 3% of solvent quality.
Performance test：
The electrolyte of the present invention carries out high voltage cycle performance test after assembled battery, and method is as follows：
The assembling of battery：With LiNi0.5Mn1.5O4For positive electrode, negative pole uses graphitized intermediate-phase carbosphere, both positive and negative polarity
Collector is respectively aluminium foil and copper foil, and barrier film uses celgard2400, forms button cell, injects in embodiment 1~6 and prepares
Electrolyte after, be assembled into 2032 button cells in glove box, tested after standing 12 hours.
High voltage cycle performance test：Battery is carried out under conditions of 25 ± 5 DEG C of room temperature, relative humidity 50~80%
3.5~5V cycle performance of battery is tested, and testing procedure is：A.1C constant-current charge is to 5V, then constant-voltage charge to cut-off current
0.01C；Stand 5 minutes；B.1C constant-current discharge stands 5 minutes to 3.5V；C. circulation step a and b, cycle-index are 1000 times.
Embodiment 1~6 prepares electrolyte viscosity, electrical conductivity and battery testing correlated results and sees attached list 1.
It was found from the high voltage cycle performance test data of subordinate list 1, using the high-voltage lithium ion of the embodiment of the present invention 1~6
Capability retention of the battery of battery electrolyte after 1000 circulations is close to 90%.
Above is presently preferred embodiments of the present invention illustrates, but the present invention is not limited to the embodiment, Mou Xiebian
Type or replacement compound are all contained in the application claim limited range.In addition, present invention uses some specific
Term, but these terms are merely for convenience of description, do not form any restrictions to the present invention.
Claims (8)
1. a kind of high-voltage lithium ion batteries electrolyte, including organic solvent, lithium salts and lithium salts cosolvent, it is characterised in that：
Described organic solvent includes fluoro alkenyl 3- nitros -4- fluoro-alkyls phenylsulfone compounds and fluoro dintrile dialkyl ether
Compound；
Described fluoro alkenyl 3- nitro -4- fluoro-alkyl phenylsulfone compounds have the structure of formula 1：
Described fluoro dintrile dialkyl ether compound has the structure of formula 2：
CN-R3-O-R4-CN
Formula 2
Wherein,
R1For C1~C5Fluoro-alkyl；
R2For C2~C5Fluoroolefin base；
R3And R4It is various independently selected from C1~C5Fluoroalkane chain group.
2. high-voltage lithium ion batteries electrolyte according to claim 1, it is characterised in that：Described organic solvent by
Following mass percent component composition：
Fluoro alkenyl 3- nitro -4- fluoro-alkyls phenylsulfone compounds 25~45%,
Fluoro dintrile dialkyl ether compound 25~45%,
Carbonats compound 10~40%.
3. high-voltage lithium ion batteries electrolyte according to claim 2, it is characterised in that：Described carbonates
Compound is in dimethyl carbonate, diethyl carbonate, fluoro diethyl carbonate, methyl ethyl carbonate, methyl acetate, methyl formate
At least one.
4. the high-voltage lithium ion batteries electrolyte according to any one of claims 1 to 3, it is characterised in that：Described
The concentration of lithium salts in organic solvent is 1.0~2.0mol/L；Described lithium salts cosolvent quality for organic solvent quality 1~
10%.
5. high-voltage lithium ion batteries electrolyte according to claim 4, it is characterised in that：Described lithium salts be LiF,
Li2O、Li2O2At least one of.
6. high-voltage lithium ion batteries electrolyte according to claim 4, it is characterised in that：Described lithium salts cosolvent
For in pentafluorophenyl group oxalic acid borate, three isopropylidene acetone base borines, three (pentafluorophenyl group) borines, three (containing fluoroalkyl) borates
At least one；Wherein, it is C containing fluoroalkyl1~C5Fluoro-alkyl.
7. high-voltage lithium ion batteries electrolyte according to claim 1, it is characterised in that：Described electrolyte includes
Dioxalic acid lithium borate and/or difluorine oxalic acid boracic acid lithium cathode film formation additive.
8. high-voltage lithium ion batteries electrolyte according to claim 7, it is characterised in that：Described cathode film formation adds
Add 1~8% that agent quality is organic solvent quality.
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Effective date of registration: 20230407 Address after: No. B-121 (2), Yiling Industrial Concentration Zone, Wuming District, Nanning City, Guangxi Zhuang Autonomous Region, 530104 Patentee after: Nanning Yisida New Energy Technology Co.,Ltd. Address before: Yuelu District City, Hunan province 410083 Changsha Lushan Road No. 932 Patentee before: CENTRAL SOUTH University |
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