CN114552016B - Electrolyte additive, lithium ion battery electrolyte and lithium ion battery - Google Patents
Electrolyte additive, lithium ion battery electrolyte and lithium ion battery Download PDFInfo
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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
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- 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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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Abstract
The invention discloses an electrolyte additive, a lithium ion battery electrolyte and lithium ionThe sub-battery, wherein the electrolyte additive comprises a compound A represented by formula 1 or formula 2,
wherein R is 1 ～R 12 Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 unsaturated group, and substituted or unsubstituted amino. The compound A is reduced at the interface of the electrode/electrolyte to form an interface film with moderate thickness, so that the thermal stability of an N-C structure on the compound A can be improved, and the high-temperature performance of the high-voltage lithium ion battery can be improved; meanwhile, an interface film formed by the compound A has a good lithium ion conduction pore channel, the lithium ion conduction pore channel is not easy to shrink at low temperature, and the lithium ion transmission pore channel is not easy to collapse and close in the circulation process, so that the compound A can also improve the low-temperature performance and the circulation performance of the high-voltage lithium ion battery.
Description
Technical Field
The invention belongs to the technical field of lithium ion batteries, and particularly relates to an electrolyte additive, a lithium ion battery electrolyte 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. In lithium ion batteries, high-voltage ternary positive electrode materials are widely applied to portable electronic equipment such as mobile phones and notebook computers and large energy storage devices due to the advantages of high energy density, environmental friendliness, long cycle life and the like, and the rapid development of electronic information technology puts higher requirements on the high-voltage and high-energy density of the lithium ion batteries.
At present, the energy density of the lithium ion battery is usually improved by increasing the charge cut-off voltage, but the nickel-cobalt-manganese ternary cathode material also has some problems at high voltage: when the voltage reaches 4.45V, the conventional electrolyte can generate oxidative decomposition side reaction on the surface of the anode material, particularly under the high-temperature condition, the oxidative decomposition of the electrolyte can be accelerated, the side reaction of the electrolyte is intensified, the deterioration reaction of the nickel-cobalt-manganese ternary anode material is promoted, and meanwhile, the nickel-cobalt-manganese ternary anode material is easy to generate H2-H3 irreversible phase change under high voltage and high temperature, so that the precipitation of oxygen is caused, the interface of the electrolyte and an electrode is unstable, and the battery faces the problems of poor high-temperature storage and serious cycle gas generation. Particularly, at low temperatures, the impedance inside the lithium ion battery increases, and the low-temperature discharge performance of the lithium ion battery is significantly insufficient. Therefore, how to ensure the high-low temperature characteristics and the cycle characteristics of the lithium ion battery while increasing the off-state voltage has been the focus of research.
Therefore, an electrolyte additive, an electrolyte for a lithium ion battery and a lithium ion battery are needed to solve the problems of the prior art.
Disclosure of Invention
The invention aims to provide an electrolyte additive which can improve the high-low temperature performance and the cycle performance of a high-voltage lithium ion battery.
It is still another object of the present invention to provide a lithium ion battery electrolyte that can improve high and low temperature performance and cycle performance of a high voltage lithium ion battery.
Another object of the present invention is to provide a lithium ion battery, which has better high and low temperature performance and cycle performance under a high voltage system.
In order to achieve the above objects, the present invention provides an electrolyte additive comprising a compound a represented by formula 1 or formula 2,
wherein R is 1 ～R 12 Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 unsaturated group, and substituted or unsubstituted amino.
Compared with the prior art, the electrolyte additive comprises a compound A shown in a structural formula 1 or a structural formula 2, the compound A is reduced at an electrode/electrolyte interface to form an interface film with moderate thickness, and the interface film has moderate thickness, so that the thermal stability of an N-C structure on the compound A can be improved, the interface film has good thermal stability, the direct contact between the electrolyte and the electrode is isolated at high temperature, the decomposition of the electrolyte is inhibited, and the high-temperature performance of the high-voltage lithium ion battery can be improved by the compound A; meanwhile, an interface film formed by the compound A has good lithium ion conducting pore channels, the lithium ion conducting pore channels are not easy to shrink at low temperature, and the lithium ion transmitting pore channels are not easy to collapse and close in the circulating process, so that the compound A can also improve the low-temperature performance and the circulating performance of the high-voltage lithium ion battery.
Preferably, R of the present invention 3 ～R 6 And R 10 ～R 12 Are all H, R 1 、R 2 、R 7～ R 9 Each independently selected from halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 unsaturated group, and substituted or unsubstituted amino.
Preferably, compound a of the present invention is selected from any one of compounds 1 to 6:
in order to achieve the above object, the present invention provides a lithium ion battery electrolyte comprising a lithium salt and an organic solvent, and further comprising the above-mentioned electrolyte additive.
Compared with the prior art, the lithium ion battery electrolyte comprises the compound A shown in the structural formula 1 or the structural formula 2, so that the lithium ion battery electrolyte is applied to a lithium ion battery, and the lithium ion battery has better high and low temperature performance and cycle performance under the high voltage of 4.45V.
Preferably, the mass of the electrolyte additive accounts for 0.1-5% of the sum of the mass of the lithium salt and the mass of the organic solvent.
Preferably, the lithium salt of the present invention is selected fromLithium hexafluorophosphate (LiPF) 6 ) Lithium perchlorate (LiClO) 4 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium methanesulfonate (LiCH) 3 SO 3 ) Lithium trifluoromethanesulfonate (LiCF) 3 SO 3 ) Lithium bis (oxalato) borate (LiC) 4 BO 8 ) Lithium difluoroborate (LiC) 2 BF 2 O 4 ) Lithium difluorophosphate (LiPO) 2 F 2 ) Lithium difluorobis (oxalato) phosphate (LiDFBP), lithium bis (fluorosulfonylimide) (LiFSI), and lithium bis (trifluoromethylsulfonyl) imide (LiTFSI). Preferably, the concentration of the lithium salt is 0.5 to 1.5M.
Preferably, the organic solvent of the present invention is at least one selected from the group consisting of chain carbonates, carboxylic acid esters, ethers, and heterocyclic compounds. Specifically, the organic solvent of the present invention is selected from 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).
Preferably, the invention also comprises an auxiliary agent, and the auxiliary agent is selected from at least one of Vinylene Carbonate (VC), vinylene Ethylene Carbonate (VEC), fluoroethylene carbonate (FEC), ethylene Sulfite (ES), 1,3 Propane Sultone (PS) and vinyl sulfate (DTD).
In order to achieve the above purpose, the present invention provides a lithium ion battery, which comprises a positive electrode material, a negative electrode material, and the above mentioned lithium ion battery electrolyte, and the maximum charging voltage is 4.45V.
Compared with the prior art, the lithium ion battery comprises the compound A shown in the structural formula 1 or the structural formula 2, the compound A is reduced at an electrode/electrolyte interface to form an interface film with moderate thickness, and the interface film has moderate thickness, so that the thermal stability of an N-C structure on the compound A can be improved, the interface film has good thermal stability, the direct contact between the electrolyte and the electrode is isolated at high temperature, and the decomposition of the electrolyte is inhibited, so that the high-voltage lithium ion battery has better high-temperature performance; meanwhile, an interface film formed by the compound A has a good lithium ion conduction pore channel, the lithium ion conduction pore channel is not easy to shrink at low temperature, and the lithium ion transmission pore channel is not easy to collapse and close in the circulation process, so that the high-voltage lithium ion battery has good low-temperature performance and circulation performance.
Preferably, the positive electrode material of the invention is LiNi x Co y Mn (1-x-y) M z O 2 Wherein 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.
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 silicon monoxide.
Detailed Description
The objects, technical solutions and advantages of the present invention are further illustrated by the following specific examples, which should not be construed as limiting the invention in any way. 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.
Example 1
Preparing an electrolyte:
ethylene Carbonate (EC), diethyl carbonate (DEC) and Ethyl Methyl Carbonate (EMC) were mixed at a mass ratio of EC: DEC: EMC =29.16 to prepare 87.48g of an organic solvent, and after mixing, 1M lithium hexafluorophosphate (LiPF) 6 ) After the lithium salt was completely dissolved, 1g of Vinylene Carbonate (VC) and 5g of additive fluoroethylene carbonate (FEC) and 0.5g of compound 1 were added.
The electrolyte compositions of examples 2 to 10 and comparative examples 1 to 6 are shown in table 1, and the electrolyte preparation methods of examples 2 to 10 and comparative examples 1 to 6 were carried out by referring to the preparation method of example 1.
TABLE 1 electrolyte composition of examples and comparative examples
Compound 7 (CAS: 3989-48-8) Compound 8 (CAS: 55276-43-2)
The electrolytes of examples 1 to 10 and comparative examples 1 to 6 were fabricated into lithium ion batteries with reference to the following lithium battery fabrication method.
The preparation method of the lithium ion battery comprises the following steps:
1. LiNi prepared from nickel cobalt lithium manganate ternary material 0.6 Co 0.2 Mn 0.2 O 2 The conductive agent SuperP, the adhesive PVDF and the Carbon Nano Tubes (CNT) are uniformly mixed according to a mass ratio of 97.5 2 Drying at 85 ℃ and then carrying out cold pressing; then trimming, cutting into pieces and slitting, drying for 4 hours at 85 ℃ under a vacuum condition after slitting, and welding tabs to prepare the lithium ion battery positive plate meeting the requirements;
2. 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 95.4 2 (ii) a Cutting edges, cutting pieces and strips, drying for 4h at 110 ℃ under a vacuum condition after the strips are cut, and welding tabs to prepare the lithium ion battery negative plate meeting the requirements;
3. 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 in vacuum at the temperature of 75 ℃, and electrolyte is injected. After standing for 24 hours, the mixture was charged to 4.45V with a constant current of 0.lC (180 mA), and then charged at a constant voltage of 4.45V until the current dropped to 0.05C (90 mA); then discharging to 3.0V at 0.2C (180 mA), repeating the charging and discharging for 2 times, and finally charging the battery to 3.8V at 0.2C (180 mA) to complete the preparation of the lithium ion battery.
After the electrolytes in the above examples and comparative examples were prepared into lithium ion batteries, the lithium ion batteries were subjected to a normal temperature cycle test, a high temperature cycle test, a low temperature test, and a high temperature storage test, respectively, under the following test conditions, and the test results are shown in table 2.
And (3) normal-temperature cycle test:
under the condition of normal temperature (25 ℃), carrying out 1.0C/1.0C charging and discharging (the battery discharge capacity is C0) on the lithium ion battery once, wherein the upper limit voltage is 4.45V, and then carrying out 1.0C/1.0C charging and discharging for 500 weeks (the battery discharge capacity is C1) under the condition of normal temperature;
capacity retention rate = (C1/C0) × 100%
High-temperature cycle test:
under the condition of over high temperature (45 ℃), carrying out 1.0C/1.0C charging and discharging (the battery discharge capacity is C0) on the lithium ion battery once, wherein the upper limit voltage is 4.45V, and then carrying out 1.0C/1.0C charging and discharging for 300 weeks (the battery discharge capacity is C1) under the normal temperature condition;
capacity retention rate = (C1/C0) × 100%
And (3) low-temperature testing:
under the condition of normal temperature (25 ℃), carrying out one-time 0.3C/0.3C charging and discharging (battery discharge capacity is recorded as C0) on the lithium ion battery, wherein the upper limit voltage is 4.45V; placing the battery in an oven at-20 ℃ for 4 hours, discharging at 0.3 ℃ and recording the discharge capacity as C1;
low temperature discharge rate = (C1/C0) × 100%
And (3) high-temperature storage test:
under the condition of normal temperature (25 ℃), carrying out one-time 0.3C/0.3C charging and discharging (battery discharge capacity is recorded as C0) on the lithium ion battery, wherein the upper limit voltage is 4.45V; placing the battery in a 60 ℃ oven for 15 days, taking out the battery, placing the battery in an environment at 25 ℃, discharging at 0.3 ℃ and recording the discharge capacity as C1; then, carrying out one-time charging and discharging of 0.3C/0.3C on the lithium ion battery (the battery discharge capacity is recorded as C2);
capacity retention rate = (C1/C0) × 100%
Capacity recovery rate = (C2/C0) = 100%
Table 2 results of performance test of lithium ion batteries of examples and comparative examples
As can be seen from table 2, the lithium ion batteries of the examples all have better high and low temperature performance, storage performance and cycle performance compared to the comparative examples, because the lithium ion batteries of the examples include the compound a represented by structural formula 1 or structural formula 2, the compound a is reduced at the electrode/electrolyte interface to form an interface film with a moderate thickness, and the thermal stability of the N-C structure on the compound a can be improved due to the moderate thickness of the interface film, so the interface film has good thermal stability, and the direct contact between the electrolyte and the electrode is isolated at high temperature, and the decomposition of the electrolyte is inhibited, so the compound a can improve the high temperature performance of the high voltage lithium ion batteries; meanwhile, an interface film formed by the compound A has good lithium ion conducting pore channels, the lithium ion conducting pore channels are not easy to shrink at low temperature, and the lithium ion transmitting pore channels are not easy to collapse and close in the circulating process, so that the lithium ion battery has better high and low temperature performance, storage performance and circulating performance under a high voltage system.
Comparing examples 1 to 10, it can be seen that the overall performance of the lithium ion battery of example 2 is the best, which may be because the steric hindrance of the side chain of compound 2 is smaller, which is more beneficial to the transmission of lithium ions, and at the same time, compound 2 can also form more LiN3, thereby further improving the high and low temperature performance of the lithium ion battery.
Comparing example 1 with comparative example 3, it can be seen that the performance of the lithium ion battery of example 1 is better than that of comparative example 3 because the thickness of the interfacial film formed by compound 7 is weak, and N — C generates gas at high voltage and high temperature, which cannot improve the high temperature characteristics of the battery, and the pores in the interfacial film formed by compound 7 are easily condensed at low temperature, so that the SEI film has excellent lithium ion transport capability at low temperature, but the pores are condensed, which causes the lithium ion transport to be hindered, which cannot improve the low temperature performance of the lithium ion battery.
Comparing examples 1, 6 and 3 to 5, it can be seen that the electrochemical performance of the lithium ion battery of comparative examples 4 to 5 is inferior to that of examples 1 and 6, which means that the concentration of compound 7 is increased by one or two times to keep the concentration of the sulfonimide group the same as that of examples 1 or 6, i.e. the thickness of the interface film formed by compound 7 is increased, but the electrochemical performance of the lithium ion battery is still inferior to that of examples 1 and 6, which may be that the interface film formed by compound 7 has weak high voltage and high temperature resistance, weak electrode/electrolyte protection under extreme conditions, and the pores of the interface film are easily condensed at low temperature, which also means that the compound a of the present application can effectively improve the electrochemical performance of the high voltage lithium ion battery, not only in relation to the thickness of the interface film formed by the compound a, but also in relation to the components of the interface film formed by the compound a, i.e. the compound a plays an important role in improving the electrochemical performance of the high voltage lithium ion battery.
Comparing example 1 with comparative example 6, it can be seen that the electrochemical performance of the lithium ion battery of example 1 is better than that of comparative example 6, because the thickness of the interfacial film formed by compound 8 is relatively thin, and at the same time, the interfacial film containing N — C is unstable at high voltage and high temperature, and easily consumes active lithium, and generates gas, and the lithium ion conducting pore channels of the interfacial film formed by compound 8 are easily shrunk at low temperature, and the lithium ion conducting pore channels are easily collapsed and closed during the circulation process, resulting in the decrease of the electrochemical performance of the lithium ion battery.
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 (8)
1. The lithium ion battery electrolyte comprises lithium salt and an organic solvent, and is characterized by also comprising an electrolyte additive, wherein the electrolyte additive comprises a compound A shown in a structural formula 2, the mass of the electrolyte additive accounts for 0.1-5% of the sum of the mass of the lithium salt and the mass of the organic solvent,
wherein R is 7 ～R 9 Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 unsaturated group, and substituted or unsubstituted amino, R 10 ～R 12 Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 unsaturated group.
2. The lithium ion battery electrolyte of claim 1 wherein R is 10 ～R 12 Are all H, R 7～ R 9 Each independently selected from halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 unsaturated group, and substituted or unsubstituted amino.
3. The lithium ion battery electrolyte of claim 1 wherein the compound a is selected from any one of compounds 3 to 6:
4. the lithium ion battery electrolyte of claim 1 wherein the lithium salt is selected from at least one of lithium hexafluorophosphate, lithium perchlorate, lithium tetrafluoroborate, lithium methylsulfonate, lithium trifluoromethylsulfonate, lithium dioxalate borate, lithium difluorooxalate borate, lithium difluorophosphate, lithium difluorobis-oxalate phosphate, lithium difluorosulfonimide and lithium bistrifluoromethylsulfonyl imide.
5. The lithium ion battery electrolyte of claim 1 wherein the organic solvent is selected from at least one of chain carbonates, carboxylic acid esters, ethers, and heterocyclic compounds.
6. The lithium ion battery electrolyte of claim 1 further comprising an additive selected from at least one of vinylene carbonate, vinylene ethylene carbonate, fluoroethylene carbonate, ethylene sulfite, 1,3 propane sultone, and ethylene sulfate.
7. A lithium ion battery, which comprises a positive electrode material and a negative electrode material, and is characterized by further comprising the lithium ion battery electrolyte as defined in any one of claims 1 to 6, and the maximum charging voltage is 4.45V.
8. The lithium ion battery of claim 7, wherein the positive electrode material is LiNi x Co y Mn (1-x-y) M z O 2 Wherein 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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| PCT/CN2022/097322 WO2023159800A1 (en) | 2022-02-25 | 2022-06-07 | Electrolyte additive, lithium ion battery electrolyte, and lithium ion battery |
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| KR20160024414A (en) * | 2014-08-25 | 2016-03-07 | 삼성에스디아이 주식회사 | Additive for electrolyte of lithium battery, electrolyte including the same and lithium battery using the electrolyte |
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| JP4815660B2 (en) * | 2000-06-16 | 2011-11-16 | 三菱化学株式会社 | Nonaqueous electrolyte and nonaqueous electrolyte secondary battery |
| KR102161266B1 (en) * | 2013-08-30 | 2020-09-29 | 삼성전자주식회사 | Electrolyte solution for seconndary lithium battery and secondary lithium battery using the same |
| JP2019050135A (en) * | 2017-09-11 | 2019-03-28 | コニカミノルタ株式会社 | Nonaqueous electrolyte composition, and, nonaqueous electrolyte secondary battery |
| US12021215B2 (en) * | 2018-10-10 | 2024-06-25 | Zeon Corporation | Conductive paste for electrode mixed material layer, slurry for electrode mixed material layer, electrode for electrochemical device, and electrochemical device |
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