CN114335723B - Additive, and non-aqueous electrolyte and lithium ion battery containing additive - Google Patents
Additive, and non-aqueous electrolyte and lithium ion battery containing additive Download PDFInfo
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- CN114335723B CN114335723B CN202111618639.2A CN202111618639A CN114335723B CN 114335723 B CN114335723 B CN 114335723B CN 202111618639 A CN202111618639 A CN 202111618639A CN 114335723 B CN114335723 B CN 114335723B
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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
- H01M10/0567—Liquid materials characterised by the additives
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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
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Abstract
The invention discloses an additive, a non-aqueous electrolyte containing the additive and a lithium ion battery, wherein the additive comprises a compound shown in a structural formula 1:
wherein R is 1 ～R 6 Each independently selected from a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, and a C6-C10 aryl group. The additive can inhibit the oxidative decomposition of the non-aqueous electrolyte, can improve the high-temperature storage performance and the high-temperature cycle performance of the lithium ion battery under a high-voltage (especially 4.5V) system, and can also improve the low-temperature discharge performance of the lithium ion battery.
Description
Technical Field
The invention belongs to the technical field of lithium ion batteries, and particularly relates to an additive, a non-aqueous electrolyte containing the additive and a lithium ion battery.
Background
The lithium ion battery has the advantages of high specific energy, no memory effect, long cycle life and the like, and is widely applied to the fields of 3C digital products, electric tools, aerospace, energy storage, power automobiles and the like. The ternary cathode material is good in safety and low in price, and therefore becomes a preferred material of the cathode active material of the lithium ion battery.
In order to meet the demand of large-scale mobile electric equipment, the development of lithium ion batteries with large specific capacity is imminent. The most common approach is to boost the voltage of li-ion batteries, but all high voltage positive electrode materials face a common problem: the decomposition problem of the electrolyte under high voltage, especially under higher voltage of 4.5V, the conventional electrolyte is faster in oxidative decomposition on the surface of the battery anode, and particularly under high temperature condition, the oxidative decomposition of the electrolyte is further accelerated, and meanwhile, the deterioration reaction of the anode material is promoted. More specifically, japanese patent JP2004071458A discloses an electrolyte containing a cyclic siloxane compound, which can improve the high-temperature storage characteristics and high-temperature cycle performance of a lithium ion battery, but is suitable for a voltage system of about 4.1V.
Therefore, it is necessary to develop an electrolyte capable of withstanding a high voltage of 4.5V to solve the problems of the prior art.
Disclosure of Invention
The invention aims to provide an additive which can inhibit the oxidative decomposition of a non-aqueous electrolyte, can improve the high-temperature storage performance and the high-temperature cycle performance of a lithium ion battery under a high-voltage (especially at 4.5V) system, and can improve the low-temperature discharge performance of the lithium ion battery.
Another object of the present invention is to provide a nonaqueous electrolyte solution, which can improve the high-temperature storage performance and the high-temperature cycle performance of a lithium ion battery in a 4.5V high-voltage system, and can also improve the low-temperature discharge performance of the lithium ion battery.
It is another object of the present invention to provide a lithium ion battery having better high temperature storage performance, high temperature cycle performance and low temperature discharge performance under a high voltage (especially at 4.5V) system.
To achieve the above object, the present invention provides an additive comprising a compound represented by structural formula 1:
wherein R is 1 ～R 6 Each independently selected from a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, and a C6-C10 aryl group.
Compared with the prior art, the additive comprisesThe compound represented by formula 1, i.e. comprising trisilicene compound having a specific structure, has an aromatic structure of planar silicon, wherein carbon is due to SP 2 Hybridization results in the formation of strongly acting pi bonds, while silicon is SP-bound 3 The additive can form a stable dimer interface film at an electrode/electrolyte interface by virtue of a sigma-pi conjugated structure between-Si ═ C < - >, so that the anode/electrolyte interface can be optimized, the surface activity of the electrode is reduced, the oxidative decomposition of the electrolyte is inhibited, the electrolyte can be kept stable under continuous high voltage, and the high-temperature storage performance and the high-temperature cycle performance of the lithium ion battery under a high-voltage (especially 4.5V) system are improved. Meanwhile, the dimer interface film has good capability of conducting lithium ions and shows lower internal resistance, so that the lithium ion battery has good low-temperature discharge performance.
Preferably, R in the compound shown in the structural formula 1 of the invention 1 、R 3 、R 5 Same as R 2 、R 4 、R 6 The same is true. Further, R 2 、R 4 、R 6 Preferably both are hydrogen atoms.
Preferably, the compound represented by the structural formula 1 of the present invention is at least one selected from the group consisting of compounds 1 to 5:
in order to achieve the above object, the present invention also provides a nonaqueous electrolytic solution comprising a lithium salt, a nonaqueous organic solvent, and further comprising the above-mentioned additive.
Compared with the prior art, the non-aqueous electrolyte comprises the compound shown in the structural formula 1, so that the non-aqueous electrolyte can keep stable under continuous high voltage, the high-temperature storage performance and the high-temperature cycle performance of the lithium ion battery under a high-voltage (especially 4.5V) system are further improved, and the low-temperature discharge performance of the lithium ion battery can be improved.
Preferably, the mass percentage of the additive of the present invention in the nonaqueous electrolyte solution is 0.1 to 5%, specifically but not limited to 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%. Further, the mass percentage of the additive in the nonaqueous electrolyte is preferably 1 to 2%.
Preferably, the mass percentage of the lithium salt in the nonaqueous electrolyte solution is 6.5-15.5%.
Preferably, the lithium salt of the present invention is selected from lithium hexafluorophosphate (LiPF) 6 ) At least one of lithium perchlorate, lithium tetrafluoroborate, lithium trifluoromethanesulfonate, lithium bistrifluoromethylsulfonimide, lithium bisoxalato borate (LiBOB), lithium difluorophosphate, lithium difluorooxalato borate, lithium difluorodioxaoxalato phosphate and lithium difluorosulfonimide.
Preferably, the nonaqueous organic solvent of the present invention is at least one of a chain carbonate, a cyclic carbonate and a carboxylic ester. The non-aqueous organic solvent is more preferably at least one selected from the group consisting of Ethylene Carbonate (EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), Ethyl Methyl Carbonate (EMC), Propylene Carbonate (PC), butyl acetate (n-Ba), γ -butyrolactone (γ -Bt), propyl propionate (n-PP), Ethyl Propionate (EP) and ethyl butyrate (Eb). Preferably, the mass percentage of the nonaqueous organic solvent in the nonaqueous electrolyte solution is 60-80%.
In order to achieve the above object, the present invention further provides a lithium ion battery, which includes a positive electrode material, a negative electrode material, and the above mentioned non-aqueous electrolyte, wherein the positive electrode material is nickel cobalt manganese oxide or nickel cobalt aluminum oxide, and the maximum charging voltage is 4.5V.
Compared with the prior art, the electrolyte of the lithium ion battery comprises the compound shown in the structural formula 1, and the compound serving as an additive can optimize an anode/electrolyte interface, reduce the surface activity of an electrode so as to inhibit the oxidative decomposition of the electrolyte, so that the electrolyte is kept stable under continuous high voltage, the high-temperature storage performance and the high-temperature cycle performance of the lithium ion battery under a 4.5V high-voltage system are further improved, and the low-temperature discharge performance of the lithium ion battery can be improved.
Preferably, the chemical formula of the nickel-cobalt-manganese oxide of the invention is LiNi x Co y Mn z M (1-x-y-z) O 2 The chemical formula of the nickel-cobalt-aluminum oxide is LiNi x Co y Al z N (1-x-y-z) O 2 Wherein M, N are each independently selected from at least one of Mg, Cu, Zn, Al, Sn, B, Ga, Cr, Sr, V and Ti, 0<x<1，0<y<1，0<z<1，x+y+z≤1。
Preferably, the negative electrode material of the present invention is selected from at least one of artificial graphite, natural graphite, lithium titanate, a silicon-carbon composite material, and silica.
Detailed Description
The purpose, technical scheme and beneficial effects of the invention are further illustrated by the following specific examples, but the invention is not limited by the following examples. The examples, in which specific conditions are not specified, may be conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used are not indicated by the manufacturer, and are all conventional products available on the market. Specifically, the compounds 1, 2, 3, 4 and 5 used in the examples can be prepared by the following synthetic routes.
And (3) carrying out gas phase dehydrogenation reaction on metal ions (Fe, Co and Ni) and trisilicon cyclohexane, and carrying out recrystallization or column chromatography purification to obtain the compound 1. More specifically, reference may be made to the prior art (Gasphaseneaktion von M) + und[CpM] + (M＝Fe,Co,Ni)mit1,3,5-Trisilacyclohexan:erste Hinweise auf die Bildung von 1,3,5-Trisilabenzol，Asgrir Bjarnason、Ingvar Arnason，Angewandte Chemie，1992)。
Reacting the compound 1 with chloromethane under an alkaline condition, and performing recrystallization or column chromatography purification to obtain a compound 2.
Reacting the compound 1 with chloroethane under an alkaline condition, and performing recrystallization or column chromatography purification to obtain a compound 3.
Reacting the compound 1 with 2-chloropropane under an alkaline condition, and purifying by recrystallization or column chromatography to obtain a compound 4.
Reacting the compound 1 with chloroethylene under an alkaline condition, and performing recrystallization or column chromatography purification to obtain a compound 5.
Example 1
(1) Preparation of non-aqueous electrolyte
In a glove box (O) filled with argon 2 ＜1ppm，H 2 O < 1ppm), Ethylene Carbonate (EC), Ethyl Methyl Carbonate (EMC), and diethyl carbonate (DEC) were mixed at a weight ratio of EC: EMC: DEC ═ 1:1:1 to prepare 86.5g of a nonaqueous organic solvent, and then 1g of compound 1 was added, and after dissolving and sufficiently stirring, 12.5g of lithium hexafluorophosphate was added, and the mixture was uniformly mixed, thereby obtaining an electrolyte solution.
(2) Preparation of the Positive electrode
LiNi prepared from nickel cobalt lithium manganate ternary material 0.5 Co 0.2 Mn 0.3 O 2 Uniformly mixing PVDF (polyvinylidene fluoride) as an adhesive and SuperP (super P) as a conductive agent according to the mass ratio of 95:1:4 to prepare a lithium ion battery anode slurry with a certain viscosity, coating the mixed slurry on two sides of an aluminum foil, drying and rolling to obtain an anode sheet.
(3) Preparation of the negative electrode
Preparing artificial graphite, a conductive agent SuperP, a thickening agent CMC and a bonding agent SBR (styrene butadiene rubber emulsion) into slurry according to the mass ratio of 95:1.5:1.0:2.5, uniformly mixing, coating the mixed slurry on two sides of a copper foil, drying and rolling to obtain the negative plate.
(4) Preparation of lithium ion batteries
And preparing the positive electrode, the diaphragm and the negative electrode into a square battery cell in a lamination mode, packaging by adopting a polymer, filling the prepared non-aqueous electrolyte of the lithium ion battery, and preparing the lithium ion battery with the capacity of 1000mAh through the working procedures of formation, capacity grading and the like.
The formulations of the nonaqueous electrolytic solutions of examples 2 to 8 and comparative example 1 are shown in table 1, and the procedure for preparing the nonaqueous electrolytic solution and the lithium ion battery is the same as that of example 1.
TABLE 1 formulation of nonaqueous electrolyte
The lithium ion batteries prepared in examples 1 to 8 and comparative example 1 were subjected to a low-temperature discharge performance test, a high-temperature storage performance test, and a high-temperature cycle performance test, respectively, under the following specific test conditions, and the performance test results are shown in table 2.
Low-temperature discharge performance test of lithium ion battery
Under the condition of normal temperature (25 ℃), the lithium ion battery is charged and discharged once at 0.5C/0.5C (the discharge capacity is recorded as C) 0 ) Charging the battery to 4.5V under the condition of constant current and constant voltage of 0.5C, placing the lithium ion battery in a low-temperature box at-20 ℃ for 4h, and discharging at-20 ℃ at 0.5C (the discharge capacity is marked as C) 1 ) Calculating the low-temperature discharge rate of the lithium ion battery by using the following formula:
low temperature discharge rate ═ C 1 /C 0 *100％
High-temperature storage performance test of lithium ion battery
Under the condition of normal temperature (25 ℃), the lithium ion battery is charged by 0.3C/0.3C onceElectric and discharge (cell discharge capacity recorded as C) 0 ) The upper limit voltage is 4.5V; placing the battery in a 60 ℃ oven for 7 days, taking out the battery, placing the battery in an environment at 25 ℃, discharging at 0.3 ℃ and recording the discharge capacity as C 1 (ii) a Then, the lithium ion battery was charged and discharged once at 0.3C/0.3C (the battery discharge capacity was recorded as C) 2 ) Calculating the capacity retention rate and the capacity recovery rate of the lithium ion battery by using the following formulas:
capacity retention rate ═ C 1 /C 0 *100％
Capacity recovery rate ═ C 2 /C 0 *100％
High-temperature cycle performance test of lithium ion battery
And (3) placing the lithium ion battery in a constant temperature box at 45 ℃, and standing for 30 minutes to keep the temperature of the lithium ion battery constant. Charging with 1C constant current to 4.5V, charging with 4.5V constant voltage to 0.05C, discharging with 1C constant current to 3.0V, and recording the first-turn discharge capacity of the battery as C 0 . This is one charge-discharge cycle. Then, 1C/1C charging and discharging were carried out at 45 ℃ for 300 weeks, and the discharge capacity was recorded as C 1 。
Capacity retention rate ═ C 1 /C 0 *100％
Table 2 lithium ion battery performance test results
As can be seen from the results in Table 2, the lithium ion batteries of examples 1 to 8 all have better high temperature storage performance, high temperature cycle performance and low temperature discharge performance than comparative example 1, because the electrolytes of the lithium ion batteries of examples 1 to 8 include the compound shown in formula 1, i.e., the trisilicon benzene compound having a specific structure, which has an aromatic structure of planar silicon, and carbon is SP 2 Hybridization results in the formation of strongly acting pi bonds, while silicon is SP-bound 3 The covalent sigma bond is formed by hybridization, so that the sigma-pi conjugated structure between-Si ═ C-can make the additive form a stable electrolyte/electrode interfaceThe dimer interface film can optimize the positive electrode/electrolyte interface, reduce the surface activity of the electrode so as to inhibit the oxidative decomposition of the electrolyte, ensure that the electrolyte is kept stable under continuous high voltage, and further improve the high-temperature storage performance and the high-temperature cycle performance of the lithium ion battery under a high-voltage (especially 4.5V) system. Meanwhile, the dimer interface film has good capability of conducting lithium ions and shows lower internal resistance, so that the lithium ion battery has good low-temperature discharge performance.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (9)
1. A nonaqueous electrolytic solution comprising a lithium salt, a nonaqueous organic solvent, and an additive, wherein the additive comprises a compound represented by formula 1:
structural formula 1
Wherein R is 1 ~R 6 Each independently selected from a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, and a C6-C10 aryl group.
2. The nonaqueous electrolytic solution of claim 1, wherein R is R 1 、R 3 、R 5 Same as R 2 、R 4 、R 6 The same is true.
3. The nonaqueous electrolytic solution of claim 1, wherein the compound represented by the structural formula 1 is at least one selected from the group consisting of compounds 1 to 5:
4. the nonaqueous electrolyte solution of claim 1, wherein the additive is present in the nonaqueous electrolyte solution in an amount of 0.1 to 5% by mass.
5. The nonaqueous electrolyte solution of claim 1, wherein the lithium salt is present in the nonaqueous electrolyte solution in an amount of 6.5 to 15.5% by mass.
6. The nonaqueous electrolytic solution of claim 1, wherein the lithium salt is selected from at least one of lithium hexafluorophosphate, lithium perchlorate, lithium tetrafluoroborate, lithium trifluoromethanesulfonate, lithium bistrifluoromethylsulfonimide, lithium bisoxalato borate, lithium difluorophosphate, lithium difluorooxalato borate, lithium difluorodioxaoxalato phosphate, and lithium difluorosulfonimide.
7. The nonaqueous electrolytic solution of claim 1, wherein the nonaqueous organic solvent is at least one of a chain carbonate, a cyclic carbonate and a carboxylic ester.
8. A lithium ion battery comprising a positive electrode material and a negative electrode material, wherein the battery further comprises the nonaqueous electrolyte according to any one of claims 1 to 7, the positive electrode material is nickel-cobalt-manganese oxide or nickel-cobalt-aluminum oxide, and the maximum charging voltage is 4.5V.
9. The lithium ion battery of claim 8, wherein the nickel cobalt manganese oxide has a chemical formula of LiNi x Co y Mn z M (1-x-y-z) O 2 The chemical formula of the nickel-cobalt-aluminum oxide is LiNi x Co y Al z N (1-x-y-z) O 2 Wherein M, N are each independently selected from at least one of Mg, Cu, Zn, Al, Sn, B, Ga, Cr, Sr, V and Ti, 0<x<1，0<y<1，0<z<1，x+y+z≤1。
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| CN202111618639.2A CN114335723B (en) | 2021-12-27 | 2021-12-27 | Additive, and non-aqueous electrolyte and lithium ion battery containing additive |
| PCT/CN2022/095092 WO2023123842A1 (en) | 2021-12-27 | 2022-05-26 | Additive, non-aqueous electrolyte solution containing said additive, and lithium-ion battery |
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| WO2006109686A1 (en) * | 2005-04-08 | 2006-10-19 | Taiyo Nippon Sanso Corporation | Material for insulating film and process for producing the same |
| JP2007173222A (en) * | 2005-11-25 | 2007-07-05 | Mitsubishi Chemicals Corp | Lithium ion secondary battery |
| CN112072180A (en) * | 2020-09-27 | 2020-12-11 | 珠海冠宇电池股份有限公司 | Electrolyte and lithium ion battery comprising same |
| CN112467204A (en) * | 2019-09-09 | 2021-03-09 | 珠海冠宇电池股份有限公司 | Lithium ion battery containing lithium ion battery electrolyte |
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| KR101287102B1 (en) * | 2011-01-27 | 2013-07-17 | 삼성에스디아이 주식회사 | Electrolyte for rechargeable lithium battery and rechargeable lithium battery including the same |
| CN105609874A (en) * | 2015-12-21 | 2016-05-25 | 东莞新能源科技有限公司 | Electrolyte solution and lithium ion battery comprising same |
| JP7084607B2 (en) * | 2018-03-22 | 2022-06-15 | 富山薬品工業株式会社 | Non-aqueous electrolyte for power storage devices |
| CN110391457B (en) * | 2018-04-23 | 2021-11-02 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery |
| CN114335723B (en) * | 2021-12-27 | 2022-09-06 | 珠海市赛纬电子材料股份有限公司 | Additive, and non-aqueous electrolyte and lithium ion battery containing additive |
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|---|---|---|---|---|
| WO2006109686A1 (en) * | 2005-04-08 | 2006-10-19 | Taiyo Nippon Sanso Corporation | Material for insulating film and process for producing the same |
| JP2007173222A (en) * | 2005-11-25 | 2007-07-05 | Mitsubishi Chemicals Corp | Lithium ion secondary battery |
| CN112467204A (en) * | 2019-09-09 | 2021-03-09 | 珠海冠宇电池股份有限公司 | Lithium ion battery containing lithium ion battery electrolyte |
| CN112072180A (en) * | 2020-09-27 | 2020-12-11 | 珠海冠宇电池股份有限公司 | Electrolyte and lithium ion battery comprising same |
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