CN119812478B - Non-aqueous electrolytes and their lithium-ion batteries - Google Patents
Non-aqueous electrolytes and their lithium-ion batteriesInfo
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- CN119812478B CN119812478B CN202510177021.9A CN202510177021A CN119812478B CN 119812478 B CN119812478 B CN 119812478B CN 202510177021 A CN202510177021 A CN 202510177021A CN 119812478 B CN119812478 B CN 119812478B
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
The invention provides a non-aqueous electrolyte and a lithium ion battery thereof. The nonaqueous electrolyte of the present invention includes a lithium salt, a nonaqueous organic solvent, and an additive including a compound a shown by structural formula I and a compound B shown by structural formula II, wherein R 1 is selected from halogen or alkylphenyl, and R 2、R3、R4、R5、R6 is each independently selected from hydrogen, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted sulfonyl. The nonaqueous electrolyte provided by the invention contains the compound A shown in the structural formula I and the compound B shown in the structural formula II, and the high-temperature storage performance and the high-temperature quick charge cycle performance of the lithium ion battery can be improved through the synergistic effect of the two substances.
Description
Technical Field
The invention relates to the technical field of lithium ion batteries, in particular to a non-aqueous electrolyte and a lithium ion battery thereof.
Background
Lithium ion batteries are widely used in portable electronic devices, electric vehicles, and large energy storage systems by virtue of their high energy density, long cycle life, and broad operating temperature ranges. With the progress of technology, the requirements for the performance of lithium ion batteries are continuously increased, and in particular, the requirements for the rapid charging performance are increasingly stringent. The electrolyte is required to have higher ionic conductivity and rapid desolvation of lithium ions, etc. due to the quick charge performance.
In the charge and discharge process of the lithium cobaltate battery, the lithium ion oxygen cobalt oxide layer of the positive electrode is subjected to deintercalation and intercalation, and reaches the negative electrode through the electrolyte and the diaphragm. In the fast charge process, the battery is under high current density, so that the electrolyte polarization in the battery is aggravated, the internal resistance is increased, and the movement speed of ions in the electrolyte is required to be fast enough. Meanwhile, the lithium battery is often accompanied with the problems of unstable structure, collapse and damage of the structure, dissolution of transition metal ion catalytic electrolyte, and the like of the positive electrode material in the quick charge process.
Therefore, there is a need to develop a nonaqueous electrolyte suitable for lithium cobaltate batteries to solve the shortcomings of the prior art.
Disclosure of Invention
The invention aims to provide a nonaqueous electrolyte and a lithium ion battery thereof, wherein the nonaqueous electrolyte simultaneously comprises a compound A shown in a structural formula I and a compound B shown in a structural formula II, and the high-temperature quick charge cycle performance and the high-temperature storage performance of the lithium ion battery can be improved through the synergistic effect of the two substances.
In order to achieve the above object, in one aspect, the present invention provides a nonaqueous electrolyte comprising a lithium salt, a nonaqueous organic solvent and an additive, the additive comprising a compound a represented by structural formula I:
And, a compound B represented by structural formula II:
Wherein R 1 is selected from halogen or alkylphenyl, R 2、R3、R4、R5、R6 is each independently selected from hydrogen, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted sulfonyl.
Compared with the prior art, the nonaqueous electrolyte comprises lithium salt, a nonaqueous organic solvent and an additive, the compound shown in the structural formula I can neutralize the alkalinity of the surface of positive electrode active material particles on the surface of a positive electrode plate, inhibit the reaction of the solvent in the electrolyte on the surface of the positive electrode plate, and the compound shown in the structural formula I contains selenium and can preferentially lose electrons compared with the oxygen of the positive electrode, so that the generation of the singlet oxygen of the positive electrode is reduced, and the oxidation of the singlet oxygen to the electrolyte is reduced. The compound shown in the structural formula II is a zwitterionic compound, the additive interacts with lithium salt in electrolyte, so that dissociation of the lithium salt and acid radical ions is quickened, the ionic conductivity of the electrolyte is improved, the transmission speed of the lithium ions is quickened, the polarization internal resistance under a quick charge condition is greatly reduced, the quick charge performance is improved, and due to instability of S-N bonds in the structure of the additive, stable S-Li bonds can be generated in situ when a CEI film is formed, the stability of the CEI film is improved, and the electrical performance of a battery under a high-temperature condition is improved. In addition, two nitrogen atoms in the additive structure have a certain degree of complexation effect on metal ions in the positive electrode material, so that the structure of the positive electrode material is more stable. Under the whole condition, the combination of the two additives combines the advantages of the two additives, thereby improving the high-temperature quick charge cycle performance and the high-temperature storage performance of the lithium ion battery.
Further, R 1 is selected from halogen or methylphenyl, R 2、R3、R4、R5、R6 is each independently selected from hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 sulfonyl.
Further, R 1 is selected from fluorine, chlorine or p-methylphenyl, R 2、R3、R4、R5 is selected from hydrogen or halogen, R 6 is selected from hydrogen, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C1-C6 sulfonyl, and when substituted, the substituent is selected from at least one of halogen or cyano.
Further, the compound B of the present invention is at least one selected from the group consisting of compounds 1 to 11:
specifically, compound 1 can be prepared according to the following synthetic route:
The synthetic routes of compounds 2-9 can refer to compound 1, which is distinguished in that the compound with Cas number 110-86-1 in the synthetic route of compound 1 is replaced by the following compounds:
compound 10 can be prepared according to the following synthetic route:
compound 11 can be prepared according to the following synthetic route:
Further, the mass percentage of the compound A in the nonaqueous electrolyte is 0.05-5%, and the mass percentage of the compound B in the nonaqueous electrolyte is 0.05-5%. As an example, the mass percentage of the compound a in the nonaqueous electrolytic solution may be, but is not limited to, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5.0%. The mass percentage of the compound B in the nonaqueous electrolytic solution may be, but is not limited to, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5.0%.
Further, the mass percentage of the compound A in the nonaqueous electrolyte is 0.1-2%, and the mass percentage of the compound B in the nonaqueous electrolyte is 0.1-4%.
Further, the mass percentage of the compound A in the nonaqueous electrolyte is 0.1-1%, and the mass percentage of the compound B in the nonaqueous electrolyte is 0.1-2%.
Further, the lithium salt of the present invention is at least one selected from the group consisting of lithium hexafluorophosphate (LiPF 6), lithium perchlorate (LiClO 4), lithium tetrafluoroborate (LiBF 4), lithium trifluoromethanesulfonate (LiCF 3SO3), lithium bis (trifluoromethanesulfonyl) imide (LiN (CF 3SO2)2), lithium bis (oxalato) borate (C 4BLiO8), lithium difluorophosphate (LiPO 2F2), lithium fluorosulfonate, lithium difluorooxalato borate (liodbb), lithium lower aliphatic carboxylate, lithium difluorodioxalate phosphate (LiDODFP) and lithium bis (fluorosulfoni), and the like.
Further, the mass percentage of the lithium salt in the nonaqueous electrolyte solution is 5-25%, further, the mass percentage of the lithium salt in the nonaqueous electrolyte solution is 8-20%, more preferably, the mass percentage of the lithium salt in the nonaqueous electrolyte solution is 10-15%, and as an example, the mass percentage of the lithium salt in the nonaqueous electrolyte solution may be, but not limited to, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 20%, 22%, 23%, 24%, 25%.
Further, the nonaqueous organic solvent of the present invention is at least one selected from the group consisting of carboxylic acid esters, carbonic acid esters and ether compounds.
Specifically, the carboxylic acid ester includes, but is not limited to, at least one of gamma-butyrolactone (gamma-Bt), gamma-valerolactone (GVL), delta-valerolactone (DVL), methyl Acetate (MA), ethyl Acetate (EA), ethyl Propionate (EP), butyl acetate (n-Ba), propyl propionate (n-PP), butyl Propionate (PRB).
Specifically, the carbonate includes, but is not limited to, at least one of Ethylene Carbonate (EC), propylene Carbonate (PCA), butylene Carbonate (BC), pentylene carbonate, dimethyl carbonate (DMC), diethyl carbonate (DEC), ethylmethyl carbonate (EMC), methyl n-propyl carbonate, ethyl n-propyl carbonate, propylene Carbonate (PC).
Specifically, the ether compound includes, but is not limited to, at least one of 1, 3-Dioxolane (DOL), 1, 4-Dioxane (DX), crown ether, tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-CH 3 -THF), 2-trifluoromethyl tetrahydrofuran (2-CF 3 -THF), dimethoxymethane (DMM), diethoxymethane (DEM), ethoxymethoxymethane (DCE), ethylene glycol di-n-propyl ether, ethylene glycol di-n-butyl Ether (EDB), diethylene glycol dimethyl ether (DEGME).
Further, the mass percentage of the nonaqueous solvent in the nonaqueous electrolyte is 65-90%, preferably the mass percentage of the nonaqueous organic solvent in the nonaqueous electrolyte is 75-89%, more preferably the mass percentage of the nonaqueous organic solvent in the nonaqueous electrolyte is 78-88%. As an example, the mass percentage of the nonaqueous organic solvent in the nonaqueous electrolytic solution may be, but is not limited to, 65%, 70%, 75%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 90%.
Further, the nonaqueous electrolytic solution of the present invention further comprises an auxiliary agent selected from at least one of fluoroethylene carbonate (FEC), vinylene Carbonate (VC), 1, 3-Propane Sultone (PS), ethylene sulfate (DTD), 1, 3-Propanediol Cyclic Sulfate (PCS), 1, 4-butanesulfonic acid lactone (1, 4-BS), triallyl phosphate (TAP) and Succinic Anhydride (SA).
Further, the mass percentage of the auxiliary agent in the nonaqueous electrolyte is 0.1-5%, and as an example, the mass percentage of the auxiliary agent in the nonaqueous electrolyte may be, but not limited to, 0.1%, 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5.0%.
The invention also provides a lithium ion battery, which comprises a positive electrode material, a negative electrode material and the non-aqueous electrolyte.
Further, the positive electrode material of the present invention is selected from lithium cobaltate, and has a chemical formula of LiCoO 2.
Further, the negative electrode material of the present invention is at least one selected from the group consisting of artificial graphite, natural graphite, lithium titanate, silicon carbon composite material, and silicon oxide. As an example, the negative electrode material is artificial graphite, but is not limited thereto.
Detailed Description
For a better description of the objects, technical solutions and advantageous effects 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 limiting the present invention.
Example 1
(1) Preparation of nonaqueous electrolyte
In a glove box filled with argon (O 2＜1ppm,H2 O <1 ppm), ethylene Carbonate (EC), ethylmethyl carbonate (EMC) and diethyl carbonate (DEC) are mixed according to the weight ratio of EC: EMC: DEC=1:1:1 to obtain 86.5g of nonaqueous organic solvent, then 0.5g of compound A and 0.5g of compound 1 are added as additives, dissolved and fully stirred, and then 12.5g of lithium hexafluorophosphate is added, and the mixture is uniformly mixed to obtain nonaqueous electrolyte.
(2) Preparation of the positive electrode
LiCoO 2, an adhesive PVDF and a conductive agent SuperP are uniformly mixed according to the mass ratio of 95:1:4 to prepare lithium ion battery anode slurry with certain viscosity, the mixed slurry is coated on two sides of an aluminum foil, and then the anode plate is obtained after drying and rolling.
(3) Preparation of negative electrode
The artificial graphite, the conductive agent SuperP, the thickening agent CMC and the adhesive SBR (styrene butadiene rubber emulsion) are prepared into slurry according to the mass ratio of 95:1.5:1.0:2.5, and the slurry is uniformly mixed, coated on two sides of a copper foil, and then dried and rolled to obtain the negative plate.
(4) Preparation of lithium ion batteries
And (3) preparing the positive electrode, the diaphragm and the negative electrode into a soft-package battery core in a winding mode, packaging by adopting a polymer aluminum plastic film, filling the prepared lithium ion battery nonaqueous electrolyte, and preparing the lithium ion battery with the capacity of 4000mAh through the working procedures of formation, capacity division and the like.
The nonaqueous electrolyte formulations of examples 1 to 20 and comparative examples 1 to 3 are shown in table 1, wherein the procedure for preparing nonaqueous electrolyte and preparing lithium ion battery of examples 2 to 20 and comparative examples 1 to 3 is the same as in example 1.
Table 1 non-aqueous electrolyte formulations table of examples 1 to 20 and comparative examples 1 to 3
The lithium ion batteries prepared in examples 1 to 20 and comparative examples 1 to 3 were subjected to a high temperature storage test and a high temperature fast charge cycle test, respectively, under the following specific test conditions, and the performance test results are shown in table 2.
High temperature storage performance test
The lithium ion battery was charged and discharged once at 0.3C/0.3C (battery discharge capacity recorded as C0) under normal temperature (25 ℃) condition, the upper limit voltage was 4.53V, the battery was put in a 60 ℃ oven to stand for 7d, the battery was taken out, the battery was put in a 25 ℃ environment to be discharged at 0.3C, the discharge capacity recorded as C1, and then the lithium ion battery was charged and discharged once at 0.3C/0.3C (battery discharge capacity recorded as C2), the capacity retention rate and the capacity recovery rate of the lithium ion battery were calculated using the following formulas:
High temperature fast charge cycle performance test
The lithium ion battery is placed in a 45 ℃ incubator and kept stand for 30 minutes, so that the lithium ion battery reaches constant temperature, is charged to a voltage of 4.53V by a constant current of 2C, is charged to a current of 0.05C by a constant voltage of 4.53V, is discharged to a voltage of 3.0V by a constant current of 1C, and the first-circle discharge capacity of the battery is recorded as C0, which is a charge-discharge cycle. Then, charging and discharging were performed at 45℃for 300 weeks at 2C/1C, the discharge capacity was noted as C1, and the capacity retention rate of the lithium ion battery was calculated using the following formula.
Table 2 results of Performance test of examples 1 to 20 and comparative examples 1 to 3
As can be seen from the results of table 2, the lithium ion batteries of examples 1 to 20 have good high temperature storage performance and high temperature fast charge cycle performance at a high voltage of 4.53V, as compared with comparative examples 1 to 3. It is possible that in the battery, the compound B shown in the structural formula II is a zwitterionic compound, the structure of the additive contains a sulfonimide group and a pyridine ring, negative charges are mainly concentrated on a nitrogen atom connected with a sulfur atom, positive charges are concentrated on the nitrogen atom on the pyridine ring, and the sulfonimide group is connected with the pyridine ring through a carbonyl group, so that the additive interacts with lithium salt in the electrolyte, and the dissociation of the lithium salt and acid radical ions is accelerated, thereby improving the ionic conductivity of the electrolyte; in addition, due to the instability of the S-N bond in the additive structure, the stable S-Li bond can be generated in situ when the SEI film is formed, and the stability of the SEI film is improved; in addition, two nitrogen atoms in the additive structure have a certain degree of complexation effect on Li +、Co3+ in the positive electrode material, so that the structure of the lithium cobaltate is more stable. Meanwhile, the compound shown in the structural formula I can be adsorbed on cobalt ions through cyano groups on the surface of the positive electrode to inhibit cobalt dissolution, and meanwhile, when the positive electrode is deeply delithiated, selenium atoms of the compound can provide electrons to reduce the separation of lattice oxygen into singlet oxygen, so that the oxidation of the singlet oxygen to electrolyte can be reduced, and the catalytic decomposition of cobalt dissolution to the electrolyte can be reduced. Meanwhile, the compound A shown in the structural formula I and the compound B shown in the structural formula II can be used for synergistic effect, so that the positive electrode of the battery can be stabilized, the broken dissolution appearance of the surface of the positive electrode can be improved, a stable CEI film can be formed, the conductivity of electrolyte can be improved, lithium ion migration is facilitated, and the high-temperature storage performance and the high-temperature quick charge cycle performance of the battery are improved.
Further, as can be seen from examples 1 to 11, by adjusting substituents with different functions on the pyridine ring, various properties of the lithium ion battery can be affected to different degrees, and more specifically, when the compound a is used in combination with the compound 9, various properties of the lithium ion battery are optimal, probably because the fluorosulfonyl group introduced by the compound 9 is a strong electron-withdrawing group, which can enable charges on the pyridine ring to be more dispersed, and the structure of the compound is more stable. In addition, in the charge and discharge cycle process of the battery, the fluorosulfonyl radical is generated along with the homolytic cleavage of the S-C bond, the activity of the fluorosulfonyl radical is high, oxygen atoms in the electrolyte solvent can be extracted to generate lithium fluorosulfonate, and the lithium fluorosulfonate has a simple molecular structure, high stability and high conductivity, so that the high-temperature performance of the lithium ion battery can be improved.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the present invention can be modified or substituted without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. A non-aqueous electrolyte comprising a lithium salt, a non-aqueous organic solvent and an additive, wherein the additive comprises a compound a of formula I:
And, a compound B represented by structural formula II:
Wherein R 1 is selected from halogen or alkylphenyl, R 2、R3、R4、R5、R6 is each independently selected from hydrogen, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted sulfonyl.
2. The nonaqueous electrolyte according to claim 1, wherein R 1 is selected from halogen or methylphenyl, and R 2、R3、R4、R5、R6 is each independently selected from hydrogen, halogen, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C1 to C10 sulfonyl.
3. The nonaqueous electrolyte according to claim 1, wherein the compound B is at least one selected from the group consisting of compounds 1 to 11:
。
4. The nonaqueous electrolytic solution according to claim 1, wherein the mass percentage of the compound a in the nonaqueous electrolytic solution is 0.05 to 5%, and the mass percentage of the compound B in the nonaqueous electrolytic solution is 0.05 to 5%.
5. The nonaqueous electrolytic solution according to claim 1, wherein the lithium salt is at least one selected from the group consisting of lithium hexafluorophosphate, lithium perchlorate, lithium tetrafluoroborate, lithium trifluoromethylsulfonate, lithium bistrifluoromethylsulfonylimide, lithium bisoxalato borate, lithium difluorophosphate, lithium fluorosulfonate, lithium difluorooxalato borate, lithium lower aliphatic carboxylate, lithium difluorobisoxalato phosphate and lithium bisfluorosulfonyl imide.
6. The nonaqueous electrolyte according to claim 5, wherein the mass percentage of the lithium salt in the nonaqueous electrolyte is 5 to 25%.
7. The nonaqueous electrolytic solution according to claim 1, wherein the nonaqueous organic solvent is at least one selected from the group consisting of carboxylic esters, carbonic esters and ether compounds.
8. The nonaqueous electrolytic solution according to claim 1, further comprising an auxiliary agent selected from at least one of fluoroethylene carbonate, vinylene carbonate, 1, 3-propane sultone, ethylene sulfate, 1, 3-propanediol cyclic sulfate, 1, 4-butane sultone, triallyl phosphate and succinic anhydride.
9. A lithium ion battery comprising a positive electrode material and a negative electrode material, characterized by further comprising the nonaqueous electrolyte according to any one of claims 1 to 8.
10. The lithium ion battery of claim 9, wherein the positive electrode material is selected from lithium cobalt oxide.
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| CN119340477A (en) * | 2023-07-19 | 2025-01-21 | 浙江蓝天环保高科技股份有限公司 | A novel electrolyte additive composition containing lithium salt and its application |
| CN119419357A (en) * | 2024-11-07 | 2025-02-11 | 合肥市赛纬电子材料有限公司 | Non-aqueous electrolyte and lithium ion battery |
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| CN105742707B (en) * | 2016-04-08 | 2018-08-14 | 深圳新宙邦科技股份有限公司 | A kind of electrolyte for lithium ion battery and lithium ion battery |
| FR3142042B1 (en) * | 2022-11-16 | 2025-07-18 | Solvionic | COMPOUND BASED ON (2-CYANOETHYL)PHOSPHONIUM SALT, ELECTROLYTE AND BATTERY COMPRISING IT |
| CN117254114A (en) * | 2023-11-17 | 2023-12-19 | 宁德时代新能源科技股份有限公司 | Battery monomer, preparation method thereof, battery comprising battery monomer and power utilization device |
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| CN119340477A (en) * | 2023-07-19 | 2025-01-21 | 浙江蓝天环保高科技股份有限公司 | A novel electrolyte additive composition containing lithium salt and its application |
| CN119419357A (en) * | 2024-11-07 | 2025-02-11 | 合肥市赛纬电子材料有限公司 | Non-aqueous electrolyte and lithium ion battery |
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