CN111129596B - High-voltage additive and high-voltage electrolyte for lithium battery - Google Patents
High-voltage additive and high-voltage electrolyte for lithium battery Download PDFInfo
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- CN111129596B CN111129596B CN201911369254.XA CN201911369254A CN111129596B CN 111129596 B CN111129596 B CN 111129596B CN 201911369254 A CN201911369254 A CN 201911369254A CN 111129596 B CN111129596 B CN 111129596B
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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
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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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- 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
Abstract
The inventionA high voltage additive and a high voltage electrolyte for a lithium battery are provided, the high voltage additive is a compound containing a cyclic enamine and thiophosphonate structure, and the structural formula I is as follows:
wherein R is1，R2Respectively one of alkyl with 1-8 carbon atoms, halogenated alkyl, alkenyl with 2-8 carbon atoms, halogenated alkenyl, alkynyl with 2-8 carbon atoms, halogenated alkynyl, aryl with 6-8 carbon atoms or halogenated aryl. The high-voltage additive disclosed by the invention can form a stable and compact CEI film on the positive electrode, stabilize transition metal ions on the surface of a positive electrode material, inhibit oxygen precipitation of the positive electrode material and reduce oxidative decomposition of electrolyte; and the film can be formed on the negative electrode, so that the stability of the SEI film of the negative electrode is improved, and the performance of the lithium battery under the high-voltage condition is improved.
Description
Technical Field
The invention belongs to the technical field of lithium batteries, and particularly relates to a high-voltage additive and a high-voltage electrolyte for a lithium battery.
Background
Since the commercialization in the 90 s of the 20 th century, lithium batteries have been widely used because of their advantages of high energy density, high charge and discharge efficiency, low self-discharge, long service life, and environmental friendliness. The method is applied to the fields of consumer electronics, aerospace, military, electric tools, electric automobiles and the like. With the development of technology, no matter in the consumer field or the power battery field, people have higher and higher requirements on the cruising ability of lithium ion batteries, and the development of high energy density (mass energy density and volume energy density) lithium batteries becomes a key point. The development of a high-energy density lithium battery can be started from two aspects, namely, the development of a new high-gram-capacity anode and cathode material; and secondly, the charging and discharging voltage of the lithium battery is improved. The charging and discharging voltage of the lithium battery is improved, the mass energy density and the volume energy density of the lithium battery can be improved, the cost of the lithium battery can be reduced, and the lithium battery becomes a hotspot of research of people.
However, in the study of high voltage lithium batteries, it was found that the deterioration of the battery performance was significant as the voltage of the lithium battery was increased. The main reason is that when the voltage of the lithium battery rises, the anode material can react with the electrolyte in the battery, and the performance of the lithium battery is affected. Therefore, it is critical to develop an electrolyte compatible with high voltage lithium batteries.
Disclosure of Invention
In view of the above, the present invention is directed to a high voltage additive and a high voltage electrolyte for a lithium battery, which can improve the stability of a CEI film on the surface of a positive electrode material of the battery and improve the cycle performance and storage performance of the lithium battery.
In order to achieve the purpose, the technical scheme of the invention is realized as follows:
a high voltage additive, said high voltage additive being a compound containing cyclic enamine and thiophosphonate structures, having the following structural formula I:
wherein R is1，R2Respectively one of alkyl with 1-8 carbon atoms, halogenated alkyl, alkenyl with 2-8 carbon atoms, halogenated alkenyl, alkynyl with 2-8 carbon atoms, halogenated alkynyl, aryl with 6-8 carbon atoms or halogenated aryl.
Furthermore, the halogenation in the halogenated alkyl, halogenated alkenyl and halogenated aryl is partial substitution or full substitution.
Further, the halogen is one or more of fluorine, chlorine and bromine.
The invention also provides a high-voltage electrolyte for the lithium battery, which comprises the following components: the electrolyte comprises a lithium salt electrolyte, an organic solvent, a high-voltage additive and an auxiliary additive, wherein the addition amount of the high-voltage additive is 0.01-5 wt% of the total mass of the electrolyte.
Further, the lithium salt electrolyte is one or more of lithium hexafluorophosphate, lithium hexafluoroarsenate, lithium perchlorate, lithium tetrafluoroborate, lithium bis (oxalato) borate, lithium difluoro (oxalato) borate, lithium methylsulfonate, lithium trifluoromethylsulfonate, lithium bis (pentafluoroethylsulfonimide), lithium bis (trifluoromethylsulfonimide) and lithium bis (fluorosulfonimide).
Further, the addition amount of the lithium salt electrolyte is 1 wt% -20 wt% of the total mass of the electrolyte.
Further, the organic solvent is any one or a mixture of several of ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, propyl methyl carbonate, 1, 4-butyrolactone, methyl formate, ethyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, ethyl butyrate and halogenated derivatives thereof.
Furthermore, the adding amount of the organic solvent is 70 wt% -90 wt% of the total mass of the electrolyte.
Further, the auxiliary additive is one or more of vinylene carbonate, vinyl ethylene carbonate, vinyl acetate, ethylene sulfite, propylene sulfite, vinyl sulfate, 1, 3-propane sultone, propenyl-1, 3-propane sultone, 1, 4-butane sultone, methyl methane disulfonate, hexamethyl disilazane, magnesium imine trifluoromethanesulfonate, tris (pentafluorophenyl) boron, tris (trimethylsilane) phosphate, tris (trimethylsilane) phosphite, nitriles, sulfones and acid anhydride.
Furthermore, the addition amount of the auxiliary additive is 1 wt% -10 wt% of the total mass of the electrolyte.
Compared with the prior art, the high-voltage additive and the high-voltage electrolyte for the lithium battery have the following advantages:
the high-voltage additive is a compound containing a cyclic enamine and thiophosphonate structure, and the additive can form a stable and compact CEI film on the positive electrode, stabilize transition metal ions on the surface of the positive electrode material, inhibit oxygen precipitation of the positive electrode material and reduce oxidative decomposition of the electrolyte; and a film can be formed on the negative electrode, so that the stability of the SEI film of the negative electrode is improved, and the performance of the lithium battery under a high-voltage condition is improved.
Detailed Description
Unless defined otherwise, technical terms used in the following examples have the same meanings as commonly understood by one of ordinary skill in the art to which the present invention belongs. The test reagents used in the following examples, unless otherwise specified, are all conventional biochemical reagents; the experimental methods are conventional methods unless otherwise specified.
The present invention will be described in detail with reference to examples.
A high voltage additive having the formula:
example 1: preparation of lithium batteries
(1) Selecting lithium cobaltate suitable for high voltage as a positive electrode material, and preparing the positive electrode material LiCoO2Mixing CNTs and PVDF uniformly according to the ratio of 98:1:1, coating the mixture on an aluminum foil current collector, drying the aluminum foil current collector through an oven, rolling the aluminum foil current collector on a roller press, and compacting the aluminum foil current collector to obtain the aluminum foil current collector with the compaction density of 4.1g/cm3And obtaining the required positive plate.
(2) Selecting artificial graphite as a negative electrode material, and mixing graphite, CMC, a conductive agent and a binder according to a ratio of 95: 1.2: 1.8: 2 to obtain a negative pole piece, wherein the compacted density of the pole piece is 1.7g/cm3。
(3) Selecting a PE film coated with ceramic as an isolating film (9+3) um, and manufacturing the pole piece into a small soft package battery of 1Ah by a lamination method for testing high-voltage electrolyte.
Example 2: lithium battery performance test
The charging and discharging voltage window of the lithium battery is 2.8-4.5V; the cycle test of the battery is that the room temperature is 25 ℃ and the high temperature is 45 ℃, and the cyclic charge-discharge current is 0.5C; the high-temperature storage performance test is that the temperature is 60 ℃, the 100 percent SOC is stored for 7 days, and the charge and discharge current is 0.5C.
Example 3:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 1% of high-voltage additive A to prepare electrolyte I.
Example 4:
in an argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 1% of high-voltage additive B to prepare electrolyte II.
Example 5:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 1% of high-voltage additive C to prepare electrolyte III.
Example 6:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being less than or equal to 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate of 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2And PS, and then adding 1% of high-voltage additive D to prepare electrolyte IV.
Example 7:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2And a PS (polystyrene) resin,then, 1% of high voltage additive E is added to prepare electrolyte V.
Example 8:
in an argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 1% of high-voltage additive F to prepare electrolyte VI.
Example 9:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 0.5% of high-voltage additive F to prepare the electrolyte VII.
Example 10:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then adding 1% of high-voltage additive G to prepare electrolyte VIII.
Example 11:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, mixing organic solvents EC, FEC and DEC according to the mass ratio of EC/FEC/DEC being 25/5/70, then adding lithium hexafluorophosphate for dissolution to prepare electrolyte with the concentration of lithium hexafluorophosphate being 1M, and then respectively accounting for 1 percent by mass,0.7 percent and 1 percent of auxiliary additives of VC and LiPO are added2F2PS, and then 0.5% of high voltage additive G is added to prepare electrolyte IX.
Example 12:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then 0.5% of high-voltage additive H is added to prepare electrolyte X.
Example 13:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being equal to or less than 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate being 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS and 0.1% of high-voltage additive B are added to prepare electrolyte XI.
Comparative example 1:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC being less than or equal to 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC being 25/5/70, then lithium hexafluorophosphate is added for dissolution, electrolyte with the concentration of lithium hexafluorophosphate of 1M is prepared, and then auxiliary additives VC and LiPO are added according to the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2And PS, comparative electrolyte 1 was prepared.
Comparative example 2:
in argon atmosphere, the environmental index is H2O≤0.5ppm，O2In a glove box with the mass ratio of EC/FEC/DEC of less than or equal to 2.0ppm, organic solvents EC, FEC and DEC are mixed according to the mass ratio of EC/FEC/DEC 25/5/70, and then lithium hexafluorophosphate is added for dissolution to prepare electrolyte with the concentration of lithium hexafluorophosphate of 1MThen adding auxiliary additives VC and LiPO in the mass fractions of 1 percent, 0.7 percent and 1 percent respectively2F2PS, and then 7% of high-voltage additive D is added to prepare electrolyte XII.
Table 1 shows the results of the electrical property tests of examples 3 to 13 and comparative examples 1 and 2.
Table 1 summary of electrical property data for different electrolytes
It can be seen from the data in table 1 that, compared to comparative electrolyte 1, the cycle life and high temperature storage life of the lithium battery are improved to some extent within a suitable addition range after the high voltage additive of the present invention is used. The high-voltage additive has excellent performance and the prepared high-voltage electrolyte has good performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A high voltage additive, characterized by: the high-voltage additive is a compound containing a cyclic enamine and thiophosphonate structure, and the structural formula I is as follows:
wherein R is1，R2Respectively one of alkyl with 1-8 carbon atoms, halogenated alkyl, alkenyl with 2-8 carbon atoms, halogenated alkenyl, alkynyl with 2-8 carbon atoms, halogenated alkynyl, aryl with 6-8 carbon atoms or halogenated aryl.
2. The high voltage additive of claim 1, wherein: the halogenation in the halogenated alkyl, the halogenated alkenyl and the halogenated aryl is partial substitution or complete substitution.
3. A high voltage additive according to any one of claims 1 or 2, wherein: halo is used as one or more of fluoro, chloro, bromo.
4. A high-voltage electrolyte for a lithium battery is characterized in that: comprises the following components: a lithium salt electrolyte, an organic solvent, the high voltage additive according to any one of claims 1 to 3, and an auxiliary additive, wherein the high voltage additive is added in an amount of 0.01 to 5 wt% based on the total mass of the electrolyte.
5. The high-voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the lithium salt electrolyte is one or more of lithium hexafluorophosphate, lithium hexafluoroarsenate, lithium perchlorate, lithium tetrafluoroborate, lithium bis (oxalate) borate, lithium difluoro (oxalate) borate, lithium methylsulfonate, lithium trifluoromethylsulfonate, lithium bis (pentafluoroethylsulfonimide), lithium bis (trifluoromethylsulfonimide) and lithium bis (fluorosulfonimide).
6. The high-voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the addition amount of the lithium salt electrolyte is 1-20 wt% of the total mass of the electrolyte.
7. The high voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the organic solvent is any one or a mixture of more of ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, propyl methyl carbonate, 1, 4-butyrolactone, methyl formate, ethyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, ethyl butyrate and halogenated derivatives thereof.
8. The high-voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the adding amount of the organic solvent is 70-90 wt% of the total mass of the electrolyte.
9. The high voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the auxiliary additive is one or more of vinylene carbonate, vinyl ethylene carbonate, vinyl acetate, ethylene sulfite, propylene sulfite, vinyl sulfate, 1, 3-propane sultone, propenyl-1, 3-propane sultone, 1, 4-butane sultone, methyl disulfonate, hexamethyl disilazane, trifluoromethyl sulfonic acid imine magnesium, tris (penta-fluorinated phenyl) boron, tris (trimethylsilane) phosphate, tris (trimethylsilane) phosphite, nitriles, sulfones and anhydride.
10. The high-voltage electrolyte for a lithium battery as claimed in claim 4, wherein: the addition amount of the auxiliary additive is 1-10 wt% of the total mass of the electrolyte.
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| CN111710909B (en) * | 2020-06-28 | 2022-06-17 | 天目湖先进储能技术研究院有限公司 | Multifunctional additive for lithium battery electrolyte, preparation method and application thereof |
| CN112310478B (en) * | 2020-10-23 | 2022-04-01 | 惠州锂威新能源科技有限公司 | Electrolyte and electrochemical device thereof |
| CN112838270B (en) * | 2021-03-18 | 2022-06-14 | 合肥国轩高科动力能源有限公司 | Electrolyte additive for improving high-temperature flatulence of battery, electrolyte and lithium ion battery containing electrolyte |
| TWI777912B (en) * | 2022-06-02 | 2022-09-11 | 台灣中油股份有限公司 | Lithium-ion battery electrolyte and lithium-ion battery |
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| CN1494723A (en) * | 2001-12-28 | 2004-05-05 | 如碧空株式会社 | Electrolytic capacitor and electrolyte for driving electrolytic capacitor |
| CN1518544A (en) * | 2001-06-15 | 2004-08-04 | 三井化学株式会社 | Piperazine derivative, process for producing the same, polymeric solid electrolyte and secondary battery |
| CN108808091A (en) * | 2018-07-19 | 2018-11-13 | 合肥国轩高科动力能源有限公司 | A kind of lithium ion battery high wellability electrolyte and lithium ion battery |
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| CN1518544A (en) * | 2001-06-15 | 2004-08-04 | 三井化学株式会社 | Piperazine derivative, process for producing the same, polymeric solid electrolyte and secondary battery |
| CN1494723A (en) * | 2001-12-28 | 2004-05-05 | 如碧空株式会社 | Electrolytic capacitor and electrolyte for driving electrolytic capacitor |
| CN108808091A (en) * | 2018-07-19 | 2018-11-13 | 合肥国轩高科动力能源有限公司 | A kind of lithium ion battery high wellability electrolyte and lithium ion battery |
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