CN113113668B - Electrolyte additive, non-aqueous electrolyte containing electrolyte additive and lithium ion battery - Google Patents
Electrolyte additive, non-aqueous electrolyte containing electrolyte additive and lithium ion battery Download PDFInfo
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- CN113113668B CN113113668B CN202110386330.9A CN202110386330A CN113113668B CN 113113668 B CN113113668 B CN 113113668B CN 202110386330 A CN202110386330 A CN 202110386330A CN 113113668 B CN113113668 B CN 113113668B
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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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- 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
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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
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
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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 invention provides an electrolyte additive, a non-aqueous electrolyte containing the electrolyte additive and a lithium ion battery, wherein the electrolyte additive comprises a compound with a structural formula 1 or a structural formula 2,
wherein R is1、R2Each independently selected from C1To C12Alkyl of (C)1To C12Haloalkyl, isocyanic acid substituted C1To C12Alkyl of (C)2To C12Alkenyl of, C2To C12Haloalkenyl of (A), C6To C26Aryl or C of6To C26Halogenated aryl of, R3Is C1To C12The alkyl group of (1). The electrolyte additive provided by the invention has the connected barbituric acid group and anhydride group, can form a nitrogen-containing carbonate interface film at the interface of an electrode/electrolyte, has good thermal stability, can inhibit the oxidative decomposition of the electrolyte, has higher performance of conducting lithium ions, and can obviously improve the conduction rate of the lithium ions, so that the high-temperature storage and cycle performance of a battery can be effectively improved on the basis of the anhydride group, the barbituric acid group and the nitrogen-containing carbonate interface film.
Description
Technical Field
The invention relates to the field of secondary batteries, in particular to an electrolyte additive, a non-aqueous electrolyte containing the electrolyte additive and a lithium ion battery.
Background
At present, the anode materials of commercial lithium ion batteries mainly comprise lithium manganate, lithium cobaltate, ternary materials and lithium iron phosphate, the charge cut-off voltage of the lithium ion batteries is generally not more than 4.2V, and along with the technological progress and the continuous development of the market, the improvement of the energy density of the lithium ion batteries is increasingly important and urgent. In addition to the existing materials and the manufacturing process improvement of the battery, the high voltage (4.35V-5V) cathode material is one of the more popular research directions, and the high energy density of the battery is realized by increasing the charging depth of the cathode active material.
The high voltage materials found so far are mainly: 1)4.35-4.5V LCO, the working voltage of the LCO is improved by doping modified elements Mg, Al, Ti and Zr or adopting a coating means, but the cobalt resource is limited and the price is relatively high, so the LCO is mainly used in small-sized mobile terminals in the 3C field; 2)5V nickel manganese spinel (LNMS) which has good cycle performance and rate capability even if a conventional electrolyte is used after being modified by doping, but has poor safety, low capacity (130mAh/g) and compaction (3.1 g/cm)3) Low, no obvious advantage compared with other high-voltage materials; 3)4.7V lithium-rich high manganese layered solid solution (OLO), high OLO capacity (300mAh/g) and high voltage, and the first effect reaches 90% after modification, but the tap density is low (2.0 g/cm)3) No voltage platform, poor cycle performance, severe voltage hysteresis, and poor safety performance, resulting in limited application; 4)4.35-4.6V ternary material, the capacity of the symmetrical (442, 333) high-voltage ternary material is high, the cycle performance is good, the upper limit voltage can be increased to 4.6V after modification, the resources of the ternary material are rich, and the higher voltage LCO has obvious advantages in price.
However, with the increase of the upper limit voltage, the ternary material has the problems of poor high-temperature storage and serious cycle gas generation. On the one hand, the new developed coating or doping technology is not perfect, and on the other hand, the matching problem of the electrolyte is solved, and the conventional electrolyte can be oxidized and decomposed on the surface of the battery anode under the high voltage of 4.4V, and particularly under the high temperature condition, the oxidative decomposition of the electrolyte can be accelerated, and meanwhile, the deterioration reaction of the anode material is promoted. Therefore, it is necessary to develop an electrolyte capable of withstanding a high voltage of 4.4V, and further to achieve excellent performance of the electrical performance of the lithium ion battery.
Disclosure of Invention
The invention aims to provide an electrolyte additive, a non-aqueous electrolyte containing the electrolyte additive and a lithium ion battery, wherein the electrolyte can improve the high-temperature storage and cycle performance of the battery, and is particularly suitable for the lithium ion battery under a high-voltage system.
In order to accomplish the above object, the present invention provides, in a first aspect, an electrolyte additive comprising a compound having structural formula 1 or structural formula 2,
wherein R is1、R2Each independently selected from C1To C12Alkyl of (C)1To C12Haloalkyl, isocyanic acid substituted C1To C12Alkyl of (C)2To C12Alkenyl of, C2To C12Halogenated alkenyl group of (1), C6To C26Aryl or C of6To C26Halogenated aryl of, R3Is C1To C12Alkyl group of (1).
Compared with the prior art, the electrolyte additive provided by the invention has the connected barbituric acid group and anhydride group, and can form a nitrogen-containing carbonate interface film at the electrode/electrolyte interface compared with the combination of barbituric acid and anhydride, the interface film has good thermal stability, can inhibit the oxidative decomposition of the electrolyte, has higher performance of conducting lithium ions, and can remarkably improve the conduction rate of the lithium ions, so that the high-temperature storage and cycle performance of a battery can be effectively improved on the basis of the anhydride group, the barbituric acid group and the nitrogen-containing carbonate interface film.
Further, R1、R2Each independently selected from C1To C6Alkyl of (C)1To C6Haloalkyl, isocyanic acid substituted C2To C7Alkyl, phenyl or halophenyl of (a).
Further, the compound having structural formula 1 or structural formula 2 is selected from at least one of compound A to compound H,
the invention provides a nonaqueous electrolyte, which comprises a lithium salt, a nonaqueous organic solvent and the electrolyte additive, wherein the weight percentage of the compound with the structural formula 1 or the structural formula 2 in the nonaqueous electrolyte is 0.1-5%.
Further, the lithium salt is selected from lithium hexafluorophosphate (LiPF)6) Lithium perchlorate (LiClO)4) Lithium difluorophosphate (LiPO)2F2) Lithium bis (oxalato) borate (C)4BLiO8) Lithium difluorooxalato borate (C)2BF2LiO4) Lithium difluorooxalato phosphate (LiDFBP), lithium tetrafluoroborate (LiBF)4) Lithium tetrafluoro-oxalato-phosphate (LiOTFP), lithium bis (trifluoromethylsulfonyl) imide (LiN (CF)3SO2)2) Lithium bis (fluorosulfonylimide) (LiFSI), and lithium trifluoromethanesulfonate (LiCF)3SO3) At least one of them, and the concentration is 0.5-1.5M.
Further, the non-aqueous organic solvent is at least one selected from the group consisting of chain carbonates, cyclic carbonates, and carboxylic esters. Still further, the non-aqueous organic solvent may be at least one 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).
The nonaqueous electrolyte further comprises 0.1-5 wt% of an auxiliary agent in the nonaqueous electrolyte, wherein the auxiliary agent is at least one selected from Vinylene Carbonate (VC), Vinyl Ethylene Carbonate (VEC), fluoroethylene carbonate (FEC), Ethylene Sulfite (ES), 1, 3-Propane Sultone (PS) and vinyl sulfate (DTD).
The third aspect of the invention also provides a lithium ion battery, which comprises a positive electrode material, a negative electrode material and an electrolyte, wherein the electrolyte is the aforementioned non-aqueous electrolyte, and the positive electrode material comprises nickel-cobalt-manganese oxide. Further, the nickel cobalt manganese is oxidizedThe chemical formula of the compound is LiNixCoyMn(1-x-y)MzO2Wherein x is more than or equal to 0.6<0.9，x+y＜1，0≤z<0.08, M is at least one of Al, Mg, Zr and Ti.
Detailed Description
To better illustrate the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to specific examples. It should be noted that the following implementation of the method is a further explanation of the present invention, and should not be taken as a limitation of the present invention.
Example 1
In a nitrogen-filled glove box (O)2＜2ppm，H2O < 3ppm), 87g of a mixture of Ethylene Carbonate (EC), diethyl carbonate (DEC) and Ethyl Methyl Carbonate (EMC) in a weight ratio of 1:1:1 was added as an organic solvent to 0.5g of Compound A to obtain a mixed solution, and 1M LiPF was slowly added to the mixed solution612.5g, and mixing uniformly to prepare the electrolyte.
The formulations of the electrolytes of examples 2 to 15 and comparative examples 1 to 9 are shown in Table 1, and the procedure for preparing the electrolyte is the same as that of example 1.
TABLE 1 electrolyte Components of the examples
NCM811 (LiNi) with a maximum charging voltage of 4.4V0.8Co0.1Mn0.1O2) The lithium ion battery is prepared by using the electrolytes of examples 1 to 15 and comparative examples 1 to 9 as a cathode material and referring to the following lithium battery preparation method, and the first coulombic efficiency test, the normal-temperature cycle performance, the high-temperature cycle performance and the high-temperature storage test are respectively carried out under the following test conditions, and the test results are shown in table 2.
The preparation method of the lithium battery comprises the following steps:
1. preparation of positive plate
LiNi prepared from nickel cobalt lithium manganate ternary material0.8Co0.1Mn0.1O2Uniformly mixing the conductive agent SuperP, the adhesive PVDF and the Carbon Nano Tubes (CNT) according to the mass ratio of 96:2:1:1 to prepare lithium ion battery anode slurry with certain viscosity, and coating the lithium ion battery anode slurry on an aluminum foil for a current collector, wherein the coating weight is 324g/m2Drying at 85 ℃ and then carrying out cold pressing; and then trimming, cutting into pieces, slitting, drying for 4h at 85 ℃ under a vacuum condition after slitting, and welding tabs to prepare the lithium ion battery positive plate meeting the requirements.
2. Preparation of negative plate
Preparing natural 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 95:1.5:1.5:2, coating the slurry on a current collector copper foil, and drying the current collector copper foil at 85 ℃, wherein the coating weight is 168g/m2(ii) a And (3) cutting edges, cutting pieces, slitting, drying for 4h at 110 ℃ under a vacuum condition after slitting, and welding tabs to prepare the lithium ion battery negative plate meeting the requirements.
3. Preparation of lithium ion battery
The positive plate, the negative plate and the diaphragm prepared by the process are manufactured into a lithium ion battery with the thickness of 4.7mm, the width of 55mm and the length of 60mm by a lamination process, the lithium ion battery is baked for 10 hours at 75 ℃, and the nonaqueous electrolyte of the embodiment 16 and the comparative examples 1-5 is injected. After standing for 24h, the mixture was charged to 4.45V with a constant current of 0.lC (180mA), and then charged at a constant voltage of 4.45V until the current dropped to 0.05C (90 mA); then discharging to 3.0V with 0.2C (180mA), repeating the charging and discharging for 2 times, finally charging the battery to 3.8V with 0.2C (180mA), and finishing the manufacture of the battery.
And (3) testing the high-temperature storage performance: 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 C0), the upper limit voltage is 4.4V, and then the battery is charged to 4.4V under the condition of 0.5C constant current and constant voltage. The lithium ion battery is placed in a high-temperature box at 60 ℃ for 30 days, and after being taken out, 0.5C discharge is carried out under the condition of normal temperature (the discharge capacity is recorded as C1); then, 0.5C/0.5C charging and discharging (discharge capacity is denoted as C2) were performed under normal temperature conditions, and the capacity retention rate and the capacity recovery rate of the lithium ion battery were calculated using the following formulas:
capacity retention rate ═ C1/C0 × 100%
Capacity recovery rate ═ C2/C0 × 100%.
And (3) normal-temperature cycle test: the lithium ion battery was charged and discharged at room temperature (25 ℃) at 1.0C/1.0C once (battery discharge capacity C0) with an upper limit voltage of 4.4V, and then charged and discharged at room temperature at 1.0C/1.0C for 500 weeks (battery discharge capacity C1),
capacity retention rate (C1/C0) × 100%.
High-temperature cycle test: under the condition of over high temperature (45 ℃), the lithium ion battery is charged and discharged at 1.0C/1.0C once (the battery discharge capacity is C0), and the upper limit voltage is 4.4V. Then, charge and discharge were carried out at 1.0C/1.0C for 500 weeks under normal temperature conditions (the cell discharge capacity was C1),
capacity retention rate (C1/C0) × 100%.
TABLE 2 results of cycle and high temperature storage Performance testing
From the results in Table 2, it is understood that the high-temperature cycle performance, the normal-temperature cycle performance, and the high-temperature storage performance of examples 1 to 15 are all at better levels than those of comparative examples 1 to 9. The electrolyte additive has the connected barbituric acid group and anhydride group, can form a nitrogen-containing carbonate interfacial film at an electrode/electrolyte interface, has good thermal stability, can inhibit the oxidative decomposition of the electrolyte, has high performance of conducting lithium ions, and can remarkably improve the conduction rate of the lithium ions, so that the high-temperature storage and cycle performance of the battery can be effectively improved on the basis of the anhydride group, the barbituric acid group and the nitrogen-containing carbonate interfacial film.
Furthermore, it can be seen from comparison of example 10 and examples 12-15 that the recycling property and high temperature property are better when some additives are added to the compound additive having formula 1 or formula 2. And when the compound is matched with VC and FEC for use, the performance is better, probably because the organic interface film formed by the compound at the interface of the electrode/electrolyte and the organic interface film formed by VC and FEC generate synergistic action, the compound has higher thermal stability and better selective permeability to lithium ions.
As can be seen from comparison between example 10 and comparative examples 5 and 7 to 8, the electrolyte additive of the present invention has a barbituric acid group and an acid anhydride group connected to each other, and compared to a combination of barbituric acid and acid anhydride, a nitrogen-containing carbonate interfacial film can be formed at an electrode/electrolyte interface, and the interfacial film has good thermal stability, can inhibit oxidative decomposition of an electrolyte, has a high performance of conducting lithium ions, can significantly increase a conduction rate of lithium ions, and therefore has good cycle performance and storage 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 to 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 electrolyte additive, characterized in that the electrolyte additive contains a compound having a structural formula 1 or a structural formula 2,
wherein R is1、R2Each independently selected from C1To C12Alkyl of (C)1To C12Haloalkyl, isocyanic acid substituted C1To C12Alkyl of (C)2To C12Alkenyl of, C2To C12Haloalkenyl of (A), C6To C26Aryl or C of6To C26Halogenated aryl of, R3Is C1To C12Alkyl group of (1).
2. The nonaqueous electrolytic solution of claim 1, wherein R is R1、R2Each independently selected from C1To C6Alkyl of (C)1To C6Haloalkyl, isocyanic acid substituted C2To C7Alkyl, phenyl or halophenyl of (a).
3. The nonaqueous electrolytic solution of claim 1, wherein the compound of formula 1 or formula 2 is at least one selected from a compound A to a compound H,
4. the nonaqueous electrolyte solution of claim 1, wherein the weight percentage of the compound of formula 1 or formula 2 in the nonaqueous electrolyte solution is 0.1-5%.
5. The nonaqueous electrolytic solution of claim 1, wherein the lithium salt is at least one selected from the group consisting of lithium hexafluorophosphate, lithium perchlorate, lithium difluorophosphate, lithium bis (oxalato) borate, lithium difluoro (oxalato) phosphate, lithium tetrafluoroborate, lithium tetrafluorooxalato phosphate, lithium bis (trifluoromethylsulfonyl) imide, lithium bis (fluorosulfonyl) imide and lithium trifluoromethanesulfonate.
6. The nonaqueous electrolytic solution of claim 1, wherein the nonaqueous organic solvent is at least one selected from the group consisting of a chain carbonate, a cyclic carbonate and a carboxylic ester.
7. The nonaqueous electrolytic solution of claim 1, further comprising an auxiliary agent selected from at least one of vinylene carbonate, vinyl ethylene carbonate, fluoroethylene carbonate, ethylene sulfite, 1, 3-propanesultone, and ethylene sulfate.
8. A lithium ion battery comprising a positive electrode material, a negative electrode material and an electrolyte, wherein the electrolyte is the nonaqueous electrolyte according to any one of claims 1 to 7, and the positive electrode material comprises a nickel-cobalt-manganese oxide.
9. The lithium ion battery of claim 8, wherein the nickel cobalt manganese oxide has a chemical formula of LiNixCoyMn(1-x-y)MzO2Wherein x is more than or equal to 0.6<0.9，x+y＜1，0≤z<0.08, M is at least one of Al, Mg, Zr and Ti.
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| CN202110386330.9A CN113113668B (en) | 2021-04-09 | 2021-04-09 | Electrolyte additive, non-aqueous electrolyte containing electrolyte additive and lithium ion battery |
| PCT/CN2021/140298 WO2022213668A1 (en) | 2021-04-09 | 2021-12-22 | Electrolyte additive and non-aqueous electrolyte and lithium ion battery containing additive |
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| CN113851716B (en) * | 2021-09-24 | 2022-05-17 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and lithium ion battery thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544743A (en) * | 1982-06-29 | 1985-10-01 | Societe Carbochimique | Salts of 1,3,5-oxadiazines-2,4,6-triones, 1,3,5-oxadiazines-2,4,6-triones and the preparation thereof |
| US20130330610A1 (en) * | 2011-02-10 | 2013-12-12 | Mitsubishi Chemical Corporation | Non-aqueous electrolyte for secondary battery and non-aqueous electrolyte secondary battery employing the same |
| CN111477961A (en) * | 2020-05-29 | 2020-07-31 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte of lithium ion battery and lithium ion battery containing non-aqueous electrolyte |
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| JP4565707B2 (en) * | 2000-06-27 | 2010-10-20 | 三井化学株式会社 | Nonaqueous electrolyte and secondary battery using the same |
| JP2013206843A (en) * | 2012-03-29 | 2013-10-07 | Mitsubishi Chemicals Corp | Nonaqueous electrolyte battery |
| WO2016027891A1 (en) * | 2014-08-22 | 2016-02-25 | 三菱化学株式会社 | Nonaqueous electrolyte solution and nonaqueous electrolyte secondary battery using same |
| JP6323476B2 (en) * | 2016-02-26 | 2018-05-16 | 東洋インキＳｃホールディングス株式会社 | Battery packaging material, battery container and battery |
| JP6638502B2 (en) * | 2016-03-22 | 2020-01-29 | 三菱ケミカル株式会社 | Non-aqueous electrolyte and non-aqueous electrolyte secondary battery using the same |
| CN113113668B (en) * | 2021-04-09 | 2022-05-17 | 珠海市赛纬电子材料股份有限公司 | Electrolyte additive, non-aqueous electrolyte containing electrolyte additive and lithium ion battery |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544743A (en) * | 1982-06-29 | 1985-10-01 | Societe Carbochimique | Salts of 1,3,5-oxadiazines-2,4,6-triones, 1,3,5-oxadiazines-2,4,6-triones and the preparation thereof |
| US20130330610A1 (en) * | 2011-02-10 | 2013-12-12 | Mitsubishi Chemical Corporation | Non-aqueous electrolyte for secondary battery and non-aqueous electrolyte secondary battery employing the same |
| CN111477961A (en) * | 2020-05-29 | 2020-07-31 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte of lithium ion battery and lithium ion battery containing non-aqueous electrolyte |
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