CN114583275A - Electrolyte containing unsaturated bond compound and battery containing electrolyte - Google Patents

Electrolyte containing unsaturated bond compound and battery containing electrolyte Download PDF

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Publication number
CN114583275A
CN114583275A CN202210218944.0A CN202210218944A CN114583275A CN 114583275 A CN114583275 A CN 114583275A CN 202210218944 A CN202210218944 A CN 202210218944A CN 114583275 A CN114583275 A CN 114583275A
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electrolyte
carbonate
propionate
halogenated
fluorinated
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孙春胜
申海鹏
吕亮
郭营军
李新丽
顿温新
赖定坤
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Xianghe Kunlun New Energy Materials 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
    • H01M10/056—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
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/64—Liquid electrolytes characterised by additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • 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
    • H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
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  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Secondary Cells (AREA)

Abstract

The invention discloses an electrolyte containing an unsaturated bond compound and a battery containing the electrolyte. The electrolyte comprises an electrolyte, an organic solvent and a compound shown in a formula I, and when the electrolyte is used in a battery, the rate charging and rate discharging performance, the cycle performance, the high-temperature storage performance and the low-temperature discharging performance of the obtained battery are improved, the 3C charging rate at normal temperature in the battery is more than 85.3%, the 1C discharging rate at 20 ℃ is more than 85.6%, the capacity retention rate of 3C charging/1C discharging cycles after 800 times of normal-temperature cycle is more than 85.6%, the capacity retention rate of 800 times of 3C charging/1C discharging cycles after 45 ℃ high-temperature cycle is more than 77.9%, and the comprehensive performance is excellent.

Description

Electrolyte containing unsaturated bond compound and battery containing electrolyte
Technical Field
The invention belongs to the technical field of batteries, and particularly relates to an electrolyte containing an unsaturated bond compound and a battery containing the electrolyte.
Background
The battery electrolyte has a crucial influence on the service life, storage life, capacity exertion, high and low temperature, safety performance and the like of the battery. Currently, commercial electrolytes are predominantly dissolved with lithium hexafluorophosphate (LiPF)6) The binary or ternary mixed solvent system of the cyclic carbonate and the chain carbonate has the characteristics of good solubility, high ionic conductivity, capability of forming a stable solid electrolyte interface film (SEI film) on the surface of a graphite cathode and the like, and is considered as the optimal choice of the electrolyte solvent system. However, organic carbonate solvents have the defects of high volatility, flammability, insufficient oxidation resistance and the like, resulting in the reduction of the safety of the battery.
A small amount of non-energy-storage substances are added into the electrolyte, so that certain properties of the battery, such as the conductivity of the electrolyte, the anode and cathode matching performance, the capacity of the battery, the cycle efficiency, the cycle life, the reversible capacity, the safety performance and the like, can be effectively improved. According to the action mechanism, the additives can be classified into SEI film-forming additives, conductive additives, flame-retardant additives, overcharge protection additives, additives for improving the low-temperature performance of the electrolyte, additives for improving the thermal stability of the electrolyte, additives for controlling the acid and water contents in the electrolyte, and the like.
CN110911750A discloses a high voltage lithium ion battery electrolyte, an additive and a preparation method of the additive, wherein the disclosed additive is thiourea derivative salt, and the disclosed preparation method of the additive comprises the following steps: (1) firstly, placing a solvent, a catalyst and thiourea in a reaction container, gradually dropwise adding organic acid, and carrying out polycondensation reaction in an ice-water bath to obtain a thiourea lipid compound; (2) separating the by-product by a water separator and high-temperature reduced pressure distillation to obtain a crude product of the thiourea ester compound; (3) and extracting the product by using a solvent, recrystallizing, purifying and drying to obtain the thiourea lipid compound. The thiourea ester compound can be used as an additive of high-voltage lithium ion battery electrolyte, can capture oxygen free radicals generated by a positive electrode material under high voltage, and can also form an SEI film.
CN103094616A discloses an electrolyte additive, a high-voltage electrolyte containing the electrolyte additive and a lithium ion battery, wherein the electrolyte additive is maleic anhydride C4H2O3Or one of the derivatives thereof, the disclosed high-voltage electrolyte can form a stable interfacial film on the surfaces of a positive electrode and a negative electrode, inhibit the reaction activity of the surfaces of the electrodes, reduce the oxidative decomposition of the electrolyte and effectively inhibit the flatulence, thereby improving the safety performance, the cycle performance under normal pressure and high voltage and the service life of the lithium ion battery.
However, the demand of high energy density and the demand of large capacity and high voltage electrode materials for batteries are increasing, and therefore, it is important to develop a compound and an electrolyte thereof that can improve the rate charging performance, the cycle performance, the high temperature storage performance and the low temperature discharge performance of the battery.
Disclosure of Invention
The invention aims to provide an electrolyte containing an unsaturated bond compound and a battery containing the electrolyte.
An electrolyte containing an unsaturated bond compound, the electrolyte comprising an electrolyte, an organic solvent and a compound represented by formula I;
Figure BDA0003535957000000021
wherein Rn is any one of C1-C10 saturated alkyl, C6-C20 aromatic alkyl, C3-C10 alkoxy or C2-C10 unsaturated alkyl.
And Rn is any one of-CH 2-, ethyl alkyl, propyl alkyl, isopropyl alkyl, allyl and fluoro groups of the groups.
The electrolyte is XClO4、XPF6、XBF4、XTFSI、XFSI、XBOB、XODFB，XCF3SO3Or XAsF6Any one or a combination of at least two of them; wherein, X is any one of Li, Na or K.
The organic solvent is any one of carbonate, carboxylate, fluorocarboxylate, propionate, fluoroether or aromatic hydrocarbon or the combination of at least two of the carbonate, the carboxylate, the fluorocarboxylate, the propionate and the fluoroether.
The carbonate is halogenated carbonate and/or non-halogenated carbonate;
the halogenated carbonate is any one or a combination of at least two of fluoroethylene carbonate, difluoroethylene carbonate, difluoropropylene carbonate, ethyl trifluoroacetate, trifluoroethyl methyl carbonate, trifluoromethyl ethylene carbonate, 4-trifluoromethyl ethylene carbonate, chloroethylene carbonate, bis (2,2, 2-trifluoroethyl) carbonate, methyl trifluoropropionate, 3,3, 3-trifluoro ethyl acetate, 2-trifluoromethyl methyl benzoate, 4,4, 4-trifluoro ethyl butyrate or 1,1,1,3,3, 3-hexafluoroisopropyl acrylate;
the non-halogenated carbonate comprises any one of ethylene carbonate, propylene carbonate, diethyl carbonate, dimethyl carbonate or ethyl methyl carbonate or the combination of at least two of the ethylene carbonate, the propylene carbonate, the diethyl carbonate, the dimethyl carbonate or the ethyl methyl carbonate.
The carboxylic ester is halogenated carboxylic ester and/or non-halogenated carboxylic ester;
the halogenated carboxylic ester is one or the combination of at least two of fluorinated propyl butyrate, fluorinated propyl acetate, fluorinated isopropyl acetate, fluorinated butyl propionate, fluorinated isopropyl propionate, fluorinated ethyl butyrate, fluorinated methyl propionate, fluorinated ethyl propionate and fluorinated propyl propionate;
the non-halogenated carboxylic acid ester is any one or combination of at least two of propyl butyrate, propyl acetate, isopropyl acetate, butyl propionate, isopropyl propionate, ethyl butyrate, methyl propionate, ethyl propionate and propyl propionate.
The fluorine ether is a fluorine ether having 7 or less carbon atoms.
The aromatic hydrocarbon is halogenated aromatic hydrocarbon and/or non-halogenated aromatic hydrocarbon; the halogenated aromatic hydrocarbon is any one or the combination of at least two of monofluorobenzene, difluorobenzene, 1,3, 5-trifluorobenzene, trifluorotoluene, 2-fluorotoluene or 2, 4-dichlorotrifluorotoluene.
The weight percentage of the electrolyte in the electrolyte is 8-49%; the weight percentage of the organic solvent in the electrolyte is 1-85%; the weight percentage of the component shown in the formula I in the electrolyte is 0.01-50%.
The electrolyte with the components in the range of 0.01-50% by weight in the electrolyte is more beneficial to improving the comprehensive performance of the battery, and when the additive is less than 0.01%, the improvement effect is not obvious, and the performance is not obviously improved when the additive exceeds 20%.
Preferably, the electrolyte further comprises other additives.
The other additives of the present invention refer to additives other than the compound represented by formula I, such as vinylene carbonate, 1, 3-propane sultone, vinyl sulfate, and the like.
A battery comprising the electrolyte of any one of the above; the battery comprises a lithium ion battery, a sodium ion battery, a potassium ion battery or a super capacitor; the negative electrode material of the lithium ion battery comprises any one or the combination of at least two of graphite, soft carbon, hard carbon, a composite material of monocrystalline silicon and graphite, a composite material of silicon oxide and graphite, and lithium titanate or niobium pentoxide.
The invention has the beneficial effects that: the electrolyte disclosed by the invention is added with the component shown in the formula I, so that when the electrolyte is used in a battery, the multiplying power charging performance, the multiplying power discharging performance, the cycle performance, the high-temperature storage performance and the low-temperature discharging performance of the obtained battery are improved, the 3C charging rate at normal temperature in the battery is more than 85.3%, the 1C discharging rate at 20 ℃ is more than 85.6%, the capacity retention rate of the 3C charging/1C discharging cycle at 800 times of normal-temperature cycle is more than 85.6%, the capacity retention rate of the 3C charging/1C discharging cycle at 45 ℃ for 800 times is more than 77.9%, and the comprehensive performance is excellent.
Detailed Description
In order that the invention may be more fully understood, reference will now be made to the following more detailed description. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
In the following examples, compound I was selected from the structure of compound II (propargyl formate) of the following formula, customized to the santai chemical of shijiazhuang (purity 99.5%):
Figure BDA0003535957000000051
the compositions of the electrolytes provided in examples 1 to 10 and comparative examples 1 to 2, which are all in weight ratio, each contained 1% VC and 1% PS, are as shown in table 1:
TABLE 1 (in the tables, all are weight ratios)
Figure BDA0003535957000000052
Figure BDA0003535957000000061
Performance test
The electrolytes described in examples 1 to 10 and comparative examples 1 to 2 were subjected to the following tests:
the electrolytes described in examples 1 to 10 and comparative example 1 were added to a silicon-carbon-containing negative electrode material (fibrate S420), a 1.67Ah lithium ion battery in which the positive electrode material was 4.5V lithium cobaltate;
the electrolyte described in example 8 and comparative example 2 was added to a battery in which the negative electrode material was graphite (cedar P15) and the positive electrode material was 4.5V lithium cobaltate to prepare a 1.67Ah lithium ion battery;
the following tests were performed:
(1) charge rate performance: the 1C current is 1.67A, and the 3C current is 5.01A; the charge and discharge potential range is 2.75V-4.50V. The charging rate of the 3C at the normal temperature is a ratio of a capacity C2 of the 3C constant current charging to a 1C constant current charging capacity C1.
(2) Cycle performance: the range of charging and discharging potential is 2.75V-4.50V, the charging current is 3C (5.01A) to 4.50V, the charging is carried out at 4.50V with constant voltage until the cut-off current is less than or equal to 0.02C (0.0334A), after standing for 5 minutes, 1C (1.67A) is discharged to 2.75V, and the standing is carried out for 5 minutes; thus, the charge and discharge are cycled.
(3) Low-temperature discharge performance: the 1C (1.67A) discharge capacity at 25 ℃ at ordinary temperature was designated as C1, and the 1C (1.67A) discharge capacity was designated as C2, after full charge at 4.5V and freezing at-20 ℃ for 4 hours. The discharge rate at-20 ℃ was C2/C1.
The test results are summarized in tables 2 to 4.
TABLE 2
Examples of the invention Type of negative electrode 3C charging Rate at Normal temperature% Discharge rate at-20 ℃ 1C%
Example 1 Silicon carbon cathode 81.3 83.0
Example 2 Silicon carbon cathode 82.5 83.6
Example 3 Silicon carbon cathode 83.4 83.9
Example 4 Silicon carbon cathode 84.1 84.5
Example 5 Silicon carbon cathode 84.9 84.8
Example 6 Silicon carbon cathode 85.3 85.6
Example 7 Silicon carbon cathode 84.1 83.9
Example 8 Silicon carbon cathode 85.9 86.2
Example 9 Silicon carbon cathode 84.5 85.0
Example 10 Silicon carbon cathode 83.0 84.8
Comparative example 1 Silicon carbon cathode 76.6 81.0
Example 8 Graphite cathode 83.8 84.2
Comparative example 2 Graphite cathode 76.8 82.1
TABLE 3
Figure BDA0003535957000000071
Figure BDA0003535957000000081
TABLE 4
Figure BDA0003535957000000082
Figure BDA0003535957000000091
As can be seen from the analysis of the data in tables 2 to 4, when the electrolyte disclosed by the invention is used in a battery, the multi-aspect performance of the battery is improved by adding the compound shown in the formula I, the 3C discharge rate at normal temperature in the battery obtained by the invention is more than 85.3%, the 1C discharge rate at-20 ℃ is more than 85.6%, the capacity retention rate of 3C charge/1C discharge cycle at normal temperature is more than 85.6%, the capacity retention rate of 800 times at 45 ℃ high temperature 3C charge/1C discharge cycle is more than 77.9%, and the comprehensive performance is excellent.
As can be seen from the analysis of comparative example 1 and example 3, the performance of comparative example 1 is inferior to that of example 3, and the electrolyte added with the compound shown in formula II is proved to improve the comprehensive performance of the battery.
Analysis of comparative example 2 and example 8 revealed similar results, demonstrating that the electrolyte solution containing the compound represented by formula II is advantageous for the charge-discharge cycle performance and low-temperature discharge performance of a battery using a silicon-containing material or graphite as a negative electrode.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (10)

1. An electrolyte containing an unsaturated bond compound, characterized by comprising an electrolyte, an organic solvent and a compound represented by formula I;
Figure FDA0003535956990000011
wherein Rn is any one of C1-C10 saturated alkyl, C6-C20 aromatic alkyl, C3-C10 alkoxy or C2-C10 unsaturated alkyl.
2. The electrolyte of claim 1, wherein Rn is any one of-CH 2-, ethyl alkyl, propyl alkyl, isopropyl alkyl, allyl, and fluoro groups thereof.
3. The electrolyte of claim 1, wherein the electrolyte is XClO4、XPF6、XBF4、XTFSI、XFSI、XBOB、XODFB，XCF3SO3Or XAsF6Any one or a combination of at least two of; wherein, X is any one of Li, Na or K.
4. The unsaturated bond compound-containing electrolytic solution according to claim 1, wherein the organic solvent is any one of or a combination of at least two of carbonate, carboxylate, fluorocarboxylate, propionate, fluoroether, and aromatic hydrocarbon.
5. The unsaturated bond-containing compound electrolytic solution according to claim 4, wherein the carbonate is a halogenated carbonate and/or a non-halogenated carbonate;
the halogenated carbonate is one or a combination of at least two of fluoroethylene carbonate, difluoroethylene carbonate, difluoropropylene carbonate, ethyl trifluoroacetate, trifluoroethyl methyl carbonate, trifluoromethyl ethylene carbonate, 4-trifluoromethyl ethylene carbonate, chloroethylene carbonate, bis (2,2, 2-trifluoroethyl) carbonate, methyl trifluoropropionate, 3,3, 3-trifluoro ethyl acetate, 2-trifluoromethyl methyl benzoate, 4,4, 4-trifluoro ethyl butyrate or 1,1,1,3,3, 3-hexafluoroisopropyl acrylate;
the non-halogenated carbonate comprises any one or a combination of at least two of ethylene carbonate, propylene carbonate, diethyl carbonate, dimethyl carbonate or ethyl methyl carbonate.
6. The electrolyte of the unsaturated bond-containing compound according to claim 4, wherein the carboxylic acid ester is a halogenated carboxylic acid ester and/or a non-halogenated carboxylic acid ester;
the halogenated carboxylic ester is one or the combination of at least two of fluorinated propyl butyrate, fluorinated propyl acetate, fluorinated isopropyl acetate, fluorinated butyl propionate, fluorinated isopropyl propionate, fluorinated ethyl butyrate, fluorinated methyl propionate, fluorinated ethyl propionate and fluorinated propyl propionate;
the non-halogenated carboxylic acid ester is any one or combination of at least two of propyl butyrate, propyl acetate, isopropyl acetate, butyl propionate, isopropyl propionate, ethyl butyrate, methyl propionate, ethyl propionate and propyl propionate.
7. The unsaturated bond-containing compound electrolytic solution according to claim 4, wherein the fluoroether is a fluoroether having 7 or less carbon atoms.
8. The unsaturated bond compound-containing electrolyte according to claim 4, wherein the aromatic hydrocarbon is a halogenated aromatic hydrocarbon and/or a non-halogenated aromatic hydrocarbon; the halogenated aromatic hydrocarbon is any one or the combination of at least two of monofluorobenzene, difluorobenzene, 1,3, 5-trifluorobenzene, trifluorotoluene, 2-fluorotoluene or 2, 4-dichlorotrifluorotoluene.
9. The electrolyte solution containing an unsaturated bond compound according to claim 1, wherein the weight percentage of the electrolyte in the electrolyte solution is 8 to 49%; the weight percentage of the organic solvent in the electrolyte is 1-85%; the weight percentage of the component shown in the formula I in the electrolyte is 0.01-50%.
10. A battery comprising the electrolyte of any one of claims 1-9; the battery comprises a lithium ion battery, a sodium ion battery, a potassium ion battery or a super capacitor; the negative electrode material of the lithium ion battery comprises any one or the combination of at least two of graphite, soft carbon, hard carbon, a composite material of monocrystalline silicon and graphite, a composite material of silicon oxide and graphite, and lithium titanate or niobium pentoxide.
CN202210218944.0A 2022-03-08 2022-03-08 Electrolyte containing unsaturated bond compound and battery containing electrolyte Pending CN114583275A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1853307A (en) * 2003-07-17 2006-10-25 宇部兴产株式会社 Nonaqueous electrolytic solution for lithium secondary battery and lithium secondary battery using the same
CN1934743A (en) * 2004-03-22 2007-03-21 宇部兴产株式会社 Nonaqueous electrolyte solution and lithium secondary battery using same
CN105324879A (en) * 2013-06-21 2016-02-10 宇部兴产株式会社 Nonaqueous electrolyte solution, electricity storage device using same, and biphenyl group-containing carbonate compound used in same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1853307A (en) * 2003-07-17 2006-10-25 宇部兴产株式会社 Nonaqueous electrolytic solution for lithium secondary battery and lithium secondary battery using the same
CN1934743A (en) * 2004-03-22 2007-03-21 宇部兴产株式会社 Nonaqueous electrolyte solution and lithium secondary battery using same
CN105324879A (en) * 2013-06-21 2016-02-10 宇部兴产株式会社 Nonaqueous electrolyte solution, electricity storage device using same, and biphenyl group-containing carbonate compound used in same

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Application publication date: 20220603