CN114122520A - Electrolyte and lithium secondary battery - Google Patents

Electrolyte and lithium secondary battery Download PDF

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Publication number
CN114122520A
CN114122520A CN202111434665.XA CN202111434665A CN114122520A CN 114122520 A CN114122520 A CN 114122520A CN 202111434665 A CN202111434665 A CN 202111434665A CN 114122520 A CN114122520 A CN 114122520A
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lithium
electrolyte
substituted
unsubstituted
additive
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丁友停
谢添
周立
玉朝琛
李帅龙
高远鹏
马美朋
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Guangzhou Tinci Materials Technology Co Ltd
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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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Secondary Cells (AREA)

Abstract

The invention relates to the technical field of lithium ion batteries, and provides an electrolyte, which comprises lithium salt, a solvent and an additive, wherein the additive is shown as the following formula 1:

Description

Electrolyte and lithium secondary battery
Technical Field
The invention relates to the technical field of lithium ion batteries, in particular to an electrolyte and a lithium secondary battery.
Background
Thiophene and pyrazine containing additives have been widely used in electrolytes as a means of improving one or more properties of lithium ion batteries.
CN201911055186.X discloses a bifunctional electrolyte additive and a lithium ion battery electrolyte containing the additive, wherein the bifunctional electrolyte additive is a phosphate or phosphite compound substituted by a five-membered or six-membered N-containing heterocyclic group, and the five-membered or six-membered N-containing heterocyclic group is one of furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine and pyridazine groups. When the battery electrolyte containing the electrolyte additive is used, on one hand, a five-membered or six-membered N-containing heterocyclic group is introduced into an SEI film, so that the ion mobility is improved, and the film forming impedance of the SEI film is reduced; on the other hand, the chemical bonds in the P-O bond and the N-containing heterocyclic group are relatively stable, so that the stability of the formed film is higher under the high-temperature condition, and the high-temperature cycle performance of the lithium ion battery, particularly the high-nickel ternary material battery, is improved.
CN201710732609.1 discloses a fluoroalkyl succinimide lithium ion battery electrolyte additive which promotes graphite carbon cathode film formation and has a structural formula shown in formula I. Wherein R1 is hydrogen, a benzene ring, a five-membered or six-membered heterocyclic group selected from furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine and pyridazine, R2 and R3 are F atoms or fluoroalkyl groups of which 1-3 hydrogen atoms in methyl, ethyl and propyl groups are substituted by F. The SEI film formed by the fluorinated alkyl sulfimide additive has better performance than that formed by VC, better improves the cycling stability of a graphite carbon cathode, improves the safety performance of a lithium ion battery, and shows good practicability and economic value.
Based on this, the present disclosure is focused on further improving the electrochemical performance of the lithium ion battery electrolyte.
The technical problem to be solved by the scheme is as follows: how to improve the high-temperature performance of the lithium ion battery electrolyte.
Disclosure of Invention
An object of the present invention is to provide an electrolyte solution that can significantly reduce the capacity retention rate and the capacity recovery rate in a high-temperature state and can reduce the expansion rate.
Meanwhile, the invention also provides a lithium secondary battery.
In order to achieve the above objects, the present invention provides an electrolyte comprising a lithium salt, a solvent and an additive, the additive being represented by formula 1 below:
Figure BDA0003381211600000021
wherein R is halogen, thiocyanate, isocyanate, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 amino, substituted or unsubstituted C1-C12 alkenyl, substituted or unsubstituted C1-C12 alkynyl, substituted or unsubstituted C1-C12 aryl, substituted or unsubstituted C1-C12 heterocyclic group; the substitution refers to at least one of halogen, thiocyanate and isocyanate substitution.
In the electrolyte, the additive formula 1 is 0.1-2% by mass of the total mass of the electrolyte.
In the above electrolyte, the additive further includes at least one of lithium bis-fluorosulfonylimide, vinylene carbonate, lithium difluoro-oxalato borate, lithium difluoro-oxalato phosphate, lithium difluoro-phosphates, fluoroethylene carbonate, fluorobenzene, ethylene trifluoroethoxycarbonate, methylene methanedisulfonate, lithium bis (trifluoromethanesulfonyl) imide, lithium bis-oxalato borate, vinyl sulfate, lithium tetrafluoroborate, difluoroethylene carbonate, 1, 3-propanesultone, succinic anhydride, ethylene sulfite, tris (trimethylsilyl) borate, tris (trimethylsilyl) phosphate, hexamethylene dinitrate, 2-propyn-1-yl 1H-imidazole-1-carboxylate.
In the electrolyte, the dosage of each of the lithium bis (fluorosulfonyl) imide, vinylene carbonate, lithium difluoro (oxalato) borate and lithium difluoro (oxalato) phosphate is not more than 3% of the total amount of the electrolyte.
In the electrolyte, the dosage of each of the lithium bis (fluorosulfonyl) imide, vinylene carbonate, lithium difluoro (oxalato) borate and lithium difluoro (oxalato) phosphate is not more than 2% of the total amount of the electrolyte.
In the electrolyte, the additive is fluorine substituted lithium salt, vinylene carbonate and additive formula 1, and the respective dosages are 0% -1%, 2% and 0.1% -2%.
In the electrolyte, the lithium salt accounts for 7-20% of the total mass of the electrolyte.
In the above electrolyte, the solvent is one or more selected from the group consisting of chain and cyclic carbonates, carboxylates, ethers, and heterocyclic compounds.
Meanwhile, the invention also discloses a lithium secondary battery, which comprises a positive electrode, a negative electrode and the lithium secondary battery electrolyte, wherein: the positive electrode material is selected from transition metal oxide of lithium, wherein the transition metal oxide of lithium is LiCoO2、LiMn2O4、LiMnO2、Li2MnO4、LiFePO4、Li1+aMn1-xMxO2、LiCo1-xMxO2、LiFe1-xMxPO4、Li2Mn1-xO4Wherein M is one or more selected from Ni, Co, Mn, Al, Cr, Mg, Zr, Mo, V, Ti, B and F, and a is more than or equal to 0<0.2，0≤x<1。
Advantageous effects
Compared with the prior art, compared with the single additive containing thiophene and pyrazine substituent groups, the lithium ion battery provided by the invention has the advantages that the high-temperature storage and cycle performance is obviously improved, and the expansion rate is obviously inhibited.
Detailed Description
The invention will now be further described with reference to the following examples, which are not to be construed as limiting the invention in any way, and any limited number of modifications which can be made within the scope of the claims of the invention are still within the scope of the claims of the invention.
In order to explain the technical contents of the present invention in detail, the following description is further made in conjunction with the embodiments.
Example 1
The preparation method of the lithium iron phosphate lithium ion soft package battery comprises the following steps:
and determining the coating surface density according to the capacity design of the battery and the capacities of the anode and cathode materials. The positive active material is a high-energy density lithium iron phosphate material purchased from Germany nanometer; the negative active material is artificial graphite purchased from Shenzhen fenofibrate; the diaphragm is a PE coated ceramic diaphragm which is purchased from a star source material and has the thickness of 20 mu m; adopting carbon-coated aluminum foil;
the preparation steps of the anode are as follows: according to LFP: SP: CNT: PVDF 95.8: 1: 0.7: 2.5, mixing lithium iron cobaltate phosphate, conductive carbon black, a carbon nano tube and a binder polyvinylidene fluoride in a mass ratio, dispersing the mixture in N-methyl-2-pyrrolidone to obtain anode slurry, uniformly coating the anode slurry on two surfaces of a carbon-coated aluminum foil, drying, rolling and vacuum drying, and welding an aluminum outgoing line by using an ultrasonic welding machine to obtain an anode sheet with the thickness of 100-180 mu m;
the preparation steps of the negative electrode are as follows: mixing graphite, conductive carbon black, binder styrene butadiene rubber and carboxymethyl cellulose according to a mass ratio of 95:1.5:2:1.5, dispersing in deionized water to obtain negative electrode slurry, coating the negative electrode slurry on two sides of a copper foil, drying, rolling and vacuum drying, and welding a nickel outgoing line by using an ultrasonic welding machine to obtain a negative electrode sheet with the thickness of 90-150 mu m;
stacking the prepared positive plate, the diaphragm and the negative plate in sequence, and winding to obtain a bare cell;
the electrolyte is prepared by the following steps: mixing Ethylene Carbonate (EC), Propylene Carbonate (PC) and diethyl carbonate (DEC) according to the mass ratio of 25:4:54.5, and adding 12.5% of lithium hexafluorophosphate, 0.5% of lithium bifluorosulfonyl imide (LiFSI), 2% of Vinylene Carbonate (VC) and 0.1% of additive shown as a formula 1 after mixing, wherein R is methyl.
And placing the bare cell in an aluminum-plastic film outer package, injecting the prepared electrolyte into the dried battery, packaging, standing, forming, shaping and testing the capacity to finish the preparation of the lithium ion battery.
Examples 2 to 6:
the same as example 1 except that the amount of the additive represented by formula 1 was adjusted to 0.2%, 0.3%, 0.5%, 1% and 2% by mass.
Example 7:
the same as example 4, except that the organic solvent was adjusted to Ethylene Carbonate (EC), Propylene Carbonate (PC), and Ethyl Methyl Carbonate (EMC) and mixed in a mass ratio of 25:4: 54.5.
Example 8:
the same as example 4 except that 1% of lithium bis (fluorosulfonyl) imide salt (LIFSI) was replaced with 1% of lithium difluoro (oxalato) borate (LiODFB).
Example 9:
the same as example 4, except that 1% of lithium bis (fluorosulfonyl) imide salt (LIFSI) was replaced with 1% of lithium difluorooxalato phosphate (LiODFP).
Example 10
The same as example 4 except that R are both C6 alkyl groups.
Example 11
The same as example 4 except that R is C12 alkyl.
Example 12
The same as example 4 except that R is methoxy.
Example 13
Substantially the same as example 4 except that R is allyl.
Example 14
Substantially the same as in example 4 except that R is a Cl atom.
Example 15
The same as example 4 except that there was no 0.5% lithium bis (fluorosulfonyl) imide salt (LiFSI).
The preparation method of the lithium iron phosphate lithium ion soft package battery comprises the following steps:
and determining the coating surface density according to the capacity design of the battery and the capacities of the anode and cathode materials. The positive active material is a high-energy density lithium iron phosphate material purchased from Germany nanometer; the negative active material is artificial graphite purchased from Shenzhen fenofibrate; the diaphragm is a PE coated ceramic diaphragm which is purchased from a star source material and has the thickness of 20 mu m; adopting carbon-coated aluminum foil;
the preparation steps of the anode are as follows: according to LFP: SP: CNT: PVDF 95.8: 1: 0.7: 2.5, mixing lithium iron cobaltate phosphate, conductive carbon black, a carbon nano tube and a binder polyvinylidene fluoride in a mass ratio, dispersing the mixture in N-methyl-2-pyrrolidone to obtain anode slurry, uniformly coating the anode slurry on two surfaces of a carbon-coated aluminum foil, drying, rolling and vacuum drying, and welding an aluminum outgoing line by using an ultrasonic welding machine to obtain an anode sheet with the thickness of 100-180 mu m;
the preparation steps of the negative electrode are as follows: mixing graphite, conductive carbon black, binder styrene butadiene rubber and carboxymethyl cellulose according to a mass ratio of 95:1.5:2:1.5, dispersing in deionized water to obtain negative electrode slurry, coating the negative electrode slurry on two sides of a copper foil, drying, rolling and vacuum drying, and welding a nickel outgoing line by using an ultrasonic welding machine to obtain a negative electrode sheet with the thickness of 90-150 mu m;
stacking the prepared positive plate, the diaphragm and the negative plate in sequence, and winding to obtain a bare cell;
the electrolyte is prepared by the following steps: mixing Ethylene Carbonate (EC), Propylene Carbonate (PC) and diethyl carbonate (DEC) according to the mass ratio of 25:4:54.5, and adding 12.5% of lithium hexafluorophosphate, 2% of Vinylene Carbonate (VC) and 0.5% of additive shown in a formula 1 in percentage by mass after mixing, wherein R is methyl.
And placing the bare cell in an aluminum-plastic film outer package, injecting the prepared electrolyte into the dried battery, packaging, standing, forming, shaping and testing the capacity to finish the preparation of the lithium ion battery.
Comparative example 1:
the same as example 4, except that the additive represented by formula 2 was used in the electrolyte instead of the additive represented by formula 1. Among them, a substituent may be a methyl group.
Figure BDA0003381211600000051
Comparative example 2:
the same as example 4, except that an additive represented by formula 3 was used in the electrolyte instead of the additive represented by formula 1, wherein a methyl group may be used as the B substituent.
Figure BDA0003381211600000061
Comparative example 3
The same as example 4, except that the additive represented by formula 1 was replaced with the additive represented by formula 2 and formula 3, wherein the amounts of formula 2 and formula 3 were 0.5%, respectively.
Lithium ion battery performance testing
Cell performance tests were performed on examples 1 to 12 and comparative examples 1 to 3, as follows:
high temperature cycle test at 45 ℃ 1C/1C: charging to 3.65V at 45 deg.C under 1C constant current, charging at constant voltage of 3.65V to 0.05C at cut-off current, and discharging at 1C constant current to obtain discharge capacity C0Repeating the charging and discharging steps for 1000 weeks to obtain the discharge capacity C at 1000 weeks1000Capacity retention rate ═ C1000/C0100%. -20 ℃ low temperature discharge test: charging to 3.65V at 25 deg.C under constant current of 1C and constant voltage of 3.65V to 0.05C at cut-off current, and discharging at constant current of 0.3C to obtain discharge capacity C0. Battery 60 ℃ 30D storage thickness expansion rate, capacity retention and capacity recovery test: charging to 3.65V at 25 deg.C under constant current of 1C and constant voltage of 3.65V to 0.05C at cut-off current, and discharging at constant current of 1C to obtain discharge capacity C0. At 25 ℃, the battery is charged to 3.65V at a constant current of 1C and to a cutoff current of 0 at a constant voltage of 3.65V.05C, recording the cell thickness D0Then the battery is placed in an explosion-proof oven at 60 ℃, stored for 30 days and tested for the thickness D of the battery in the oven1Then, the cell was taken out and cooled to room temperature, and the discharge retention capacity C of 1C discharge to 2.0V was tested2Then, the charging and discharging steps are repeated for 5 weeks, and the 3 rd week discharge capacity C of the battery is recorded3Thickness expansion ratio ═ D1-D0)/D0100%, capacity retention ═ C2/C0100%, capacity recovery rate ═ C3/C0*100％。
After the electrolyte in the above embodiment is made into a lithium ion battery, the high temperature cycle performance and the high temperature storage performance of the lithium ion battery are tested, and the results are shown in table two:
table two: lithium ion battery performance test results
Figure BDA0003381211600000071
And (3) analyzing an experimental result:
1. through the comparative example 1 and the examples 1-6, the additive shown in the formula 1 can obviously improve the high-temperature cycle and high-temperature storage performance of the battery, and the preferable addition amount is 0.5-1% by mass fraction; from the economical point of view, 0.5% is most preferable.
2. By comparing comparative example 1, example 4, example 8 and example 9, it can be seen that the combination of the additive shown in formula 1 and LiODFB or LiODFP can improve the battery performance comprehensively, and the effect of the combination of the additive and LiODFP is better.
3. By comparing comparative example 1, comparative example 2, comparative example 3, example 4 and examples 10 to 14, it can be found that the improvement of the high-temperature performance of the battery by the additive shown in formula 1 is better than that of the fluorinated alkyl sulfonyl imide additive in patent CN201710732609.1, especially the effect of inhibiting high-temperature gas generation is obviously superior, and the additive with the structure shown in formula 1 used in example 13 has the best comprehensive performance.
4. It can be seen from the comparison between example 15 and example 4 that the combination of VC and additive formula 1 is superior to the case where the fluorine-substituted lithium salt, vinylene carbonate and additive formula 1 are present simultaneously.
The examples presented herein are only implementations selected according to a combination of all possible examples. The appended claims should not be limited to the description of the embodiments of the invention. Where numerical ranges are used in the claims, including sub-ranges therein, variations in these ranges are also intended to be covered by the appended claims.

Claims (9)

1. An electrolyte comprising a lithium salt, a solvent and an additive, wherein the additive is represented by formula 1 below:
Figure FDA0003381211590000011
wherein R is halogen, thiocyanate, isocyanate, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 amino, substituted or unsubstituted C1-C12 alkenyl, substituted or unsubstituted C1-C12 alkynyl, substituted or unsubstituted C1-C12 aryl, substituted or unsubstituted C1-C12 heterocyclic group; the substitution refers to at least one of halogen, thiocyanate and isocyanate substitution.
2. The electrolyte according to claim 1, wherein the additive formula 1 is 0.1 to 2 mass% of the total mass of the electrolyte.
3. The electrolyte of claim 1, wherein the additive further comprises at least one of lithium bis-fluorosulfonylimide, vinylene carbonate, lithium difluorooxalato borate, lithium difluorooxalato phosphate, lithium difluorophosphate, fluoroethylene carbonate, fluorobenzene, ethylene trifluoroethoxycarbonate, methylene methanedisulfonate, lithium bis (trifluoromethanesulfonyl) imide, lithium bis-oxalato borate, vinyl sulfate, lithium tetrafluoroborate, difluorovinyl carbonate, 1, 3-propanesultone, succinic anhydride, vinyl sulfite, tris (trimethylsilane) borate, tris (trimethylsilane) phosphate, hexamethylene diisocyanate, 2-propyn-1-yl 1H-imidazole-1-carboxylate.
4. The electrolyte of claim 3, wherein the lithium bis-fluorosulfonylimide, vinylene carbonate, lithium difluorooxalate borate, and lithium difluorooxalate phosphate are each used in an amount of no more than 3% of the total electrolyte.
5. The electrolyte of claim 3, wherein the lithium bis-fluorosulfonylimide, vinylene carbonate, lithium difluorooxalate borate, and lithium difluorooxalate phosphate are each used in an amount of no more than 2% of the total electrolyte.
6. The electrolyte of claim 5, wherein the additive is a fluorine substituted lithium salt, vinylene carbonate, additive formula 1, and the respective amounts are 0% -1%, 2%, and 0.1% -2%.
7. The electrolyte according to claim 1, wherein the lithium salt is 7 to 20 mass% of the total mass of the electrolyte.
8. The electrolyte of claim 1, wherein the solvent is selected from one or more of chain and cyclic carbonates, carboxylates, ethers, and heterocyclic compounds.
9. A lithium secondary battery characterized in that: the lithium secondary battery comprising a positive electrode, a negative electrode and the lithium secondary battery electrolyte according to any one of claims 1 to 8, wherein: the positive electrode material is selected from transition metal oxide of lithium, wherein the transition metal oxide of lithium is LiCoO2、LiMn2O4、LiMnO2、Li2MnO4、LiFePO4、Li1+aMn1-xMxO2、LiCo1-xMxO2、LiFe1-xMxPO4、Li2Mn1-xO4Wherein M is one or more selected from Ni, Co, Mn, Al, Cr, Mg, Zr, Mo, V, Ti, B and F, and a is more than or equal to 0<0.2，0≤x<1。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024113440A1 (en) * 2022-12-02 2024-06-06 东莞市杉杉电池材料有限公司 Secondary battery electrolyte and additive

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024113440A1 (en) * 2022-12-02 2024-06-06 东莞市杉杉电池材料有限公司 Secondary battery electrolyte and additive

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