WO2019200656A1 - Électrolyte de batterie secondaire au lithium et batterie secondaire au lithium associée - Google Patents

Électrolyte de batterie secondaire au lithium et batterie secondaire au lithium associée Download PDF

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WO2019200656A1
WO2019200656A1 PCT/CN2018/087900 CN2018087900W WO2019200656A1 WO 2019200656 A1 WO2019200656 A1 WO 2019200656A1 CN 2018087900 W CN2018087900 W CN 2018087900W WO 2019200656 A1 WO2019200656 A1 WO 2019200656A1
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Prior art keywords
secondary battery
lithium secondary
lithium
electrolyte
battery electrolyte
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PCT/CN2018/087900
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English (en)
Chinese (zh)
Inventor
范伟贞
余乐
谢添
赵经纬
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广州天赐高新材料股份有限公司
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Publication of WO2019200656A1 publication Critical patent/WO2019200656A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—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
    • H01M10/0568—Liquid materials characterised by the solutes
    • 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
    • H01M10/0569—Liquid materials characterised by the solvents
    • 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
    • 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

Definitions

  • the present invention relates to the field of lithium secondary battery technology, and in particular to a lithium secondary battery electrolyte and a lithium secondary battery containing the same.
  • solvents with higher boiling points such as diethyl carbonate and ethyl methyl carbonate are generally selected as the main solvent of the electrolyte, but the melting point of these solvents is higher, and the conductivity of the electrolyte at low temperatures. The drop is very fast and the battery impedance increases rapidly. It is difficult to meet the low-temperature discharge performance of the battery.
  • a carboxylate having a lower melting point such as ethyl acetate or ethyl propionate is generally selected as the main solvent of the electrolytic solution, but the boiling point of these solvents is relatively low, which is disadvantageous for improving the high-temperature performance of the battery.
  • additives in order to improve high temperature performance, additives such as vinylene carbonate and ethylene carbonate are generally used, but such additives may cause a large battery impedance, especially at low temperatures, the battery impedance is increased significantly, resulting in a battery. The low temperature performance is degraded. Therefore, it is a difficult task to improve the high and low temperature performance of the battery through the electrolyte.
  • Patent application CN201410505635.7 discloses a lithium ion battery and an electrolyte thereof, the electrolyte of the lithium ion battery comprising: a non-aqueous organic solvent; a lithium salt dissolved in a non-aqueous organic solvent; and an additive.
  • the additives include fluoroethylene carbonate (FEC), 1,3-propane sultone (PS), and cyano group-containing titanates.
  • FEC fluoroethylene carbonate
  • PS 1,3-propane sultone
  • cyano group-containing titanates include fluoroethylene carbonate (FEC), 1,3-propane sultone (PS), and cyano group-containing titanates.
  • the lithium ion battery includes the electrolyte of the foregoing lithium ion battery, which has excellent storage performance and cycle performance under high temperature and high pressure.
  • Patent application CN201310034975.1 discloses an electrolyte for a negative electrode lithium titanate battery, a lithium ion battery and a preparation method thereof.
  • the electrolyte uses lithium hexafluorophosphate as an electrolyte, and ethylene carbonate, ethyl methyl carbonate, diethyl carbonate and propylene carbonate.
  • the ester is a solvent, and one or more of fluoroethylene carbonate, lithium bis(oxalate) borate, 1,3-propane sultone or vinylene carbonate is a film-forming additive.
  • the above-mentioned scheme has a problem in that it has a good capacity recovery rate at normal temperature and high temperature, and does not describe battery performance under low temperature conditions.
  • a lithium secondary battery electrolyte comprising an organic solvent, a conductive lithium salt, a phenyl or pyridyl-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the phenyl or pyridyl substituted bis(trifluoromethanesulfonyl)amine compound is selected from the group consisting of N,N-bis(trifluoromethanesulfonyl)aniline, N,N-bis(trifluoromethyl) At least one of sulfamoyl)-2-pyridinamine.
  • the phenyl or pyridyl substituted bis(trifluoromethanesulfonyl)amine compound comprises from 0.1% to 5.0% by weight of the total mass of the lithium secondary battery electrolyte.
  • the additive is selected from at least one of lithium difluorodioxalate phosphate, triallyl isocyanurate, and 2-propynyl carbonate.
  • the additive comprises from 0.1% to 5.0% of the total mass of the lithium secondary battery electrolyte.
  • the conductive lithium salt is at least one of lithium hexafluorophosphate or lithium bisfluorosulfonimide, which is from 8.0 to 18.0% of the total mass of the electrolyte of the lithium secondary battery.
  • the organic solvent consists of a cyclic solvent and a linear solvent.
  • the cyclic solvent is selected from at least one of ethylene carbonate, propylene carbonate, ⁇ -butyrolactone, and 1,4 butyl sultone.
  • the linear solvent is selected from the group consisting of dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, ethyl acetate, methyl propyl carbonate, propyl propionate, 1, 1, 2, 2 At least one of tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether and 2,2-difluoroethyl acetate.
  • Another object of the present invention is to provide a lithium secondary battery.
  • a lithium secondary battery comprising the above lithium secondary battery electrolyte (including a positive electrode sheet containing a positive electrode active material, a negative electrode sheet containing a negative electrode active material, and a separator).
  • the positive electrode active material means a lithium-containing metal compound
  • the lithium-containing metal compound is Li 1+a (Ni x Co y M 1-xy )O 2 , Li(Ni p Mn q At least one of Co 2-pq )O 4 and LiM h (PO 4 ) m , wherein 0 ⁇ a ⁇ 0.3, 0 ⁇ x ⁇ 1, 0 ⁇ y ⁇ 1, 0 ⁇ x+y ⁇ 1, 0 ⁇ p ⁇ 2, 0 ⁇ q ⁇ 2, 0 ⁇ p + q ⁇ 2, M is Fe, Ni, Co, Mn, Al or V, 0 ⁇ h ⁇ 5, 0 ⁇ m ⁇ 5; the negative active material is lithium At least one of a metal, a lithium alloy, a carbon material, a silicon-based material, and a tin-based material.
  • the above electrolyte can be used in combination with triallyl isocyanurate or 2-propynyl methyl carbonate by adding a phenyl or pyridyl-substituted bis(trifluoromethanesulfonyl)amine compound to improve the normal temperature cycle of the electrolyte. Performance, high temperature storage performance and low temperature discharge performance.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 76.0% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (ethyl methyl carbonate), and the mass ratio of ethylene carbonate to ethyl methyl carbonate is 1 :1.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 18.0% of the total mass of the lithium secondary battery electrolyte.
  • N,N-bis(trifluoromethanesulfonyl)aniline accounts for 5.0% of the total mass of the electrolyte.
  • the additive is lithium difluorodioxalate phosphate, which accounts for 1.0% of the total mass of the electrolyte.
  • the electrolytic solution of this example was applied to a LiNi 0.8 Co 0.1 Mn 0.1 O 2 /graphite soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 80.5% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (dimethyl carbonate), and the mass ratio of the ethylene carbonate to the dimethyl carbonate is 1 :2.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 15.0% of the total mass of the lithium secondary battery electrolyte.
  • N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine accounts for 0.5% of the total mass of the electrolyte, and the additive is triallyl isocyanurate, 2-propynyl methyl carbonate, It accounts for 1.0% and 3.0% of the total mass of the electrolyte.
  • the electrolytic solution of this example was used for a LiNi 0.8 Co 0.1 Mn 0.1 O 2 /silicon carbon soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 85.0% of the total mass of the electrolyte of the lithium secondary battery, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (diethyl carbonate), and the mass ratio of ethylene carbonate to diethyl carbonate is 1 :3.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 12.0% of the total mass of the lithium secondary battery electrolyte.
  • N,N-bis(trifluoromethanesulfonyl)aniline accounts for 1.0% of the total mass of the electrolyte, and the additive is lithium difluorodioxalate phosphate and triallyl isocyanurate, respectively, which account for the total mass of the electrolyte. 1.0%, 1.0%.
  • the electrolytic solution of this example was used for a LiNi 0.6 Co 0.2 Mn 0.2 O 2 /graphite soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound.
  • the organic solvent accounts for 86.0% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate, propylene carbonate) and a linear solvent (ethyl methyl carbonate, propyl propionate), ethylene carbonate,
  • the mass ratio of propylene carbonate, ethyl methyl carbonate, and propyl propionate was 1:0.5:1:1.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 12.0% of the total mass of the lithium secondary battery electrolyte.
  • N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine accounts for 1.0% of the total mass of the electrolyte, and the additive is lithium difluorodioxalate phosphate, which accounts for 1.0% of the total mass of the electrolyte.
  • the electrolytic solution of this example was applied to a LiNi 0.6 Co 0.2 Mn 0.2 O 2 /silicon carbon soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 88.0% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (ethyl methyl carbonate, 1,1,2,2-tetrafluoroethyl-2, 2,3,3-tetrafluoropropyl ether) composition, ethylene carbonate, propylene carbonate, ethyl methyl carbonate, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoro
  • the mass ratio of propyl ether was 1:2:0.5.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 8.5% of the total mass of the lithium secondary battery electrolyte.
  • N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine accounts for 1.0% of the total mass of the electrolyte, and the additive is lithium difluorodioxalate phosphate and methyl 2-propynyl carbonate, respectively. 0.5% and 2.0% of the total mass of the liquid.
  • the electrolytic solution of this example was applied to a LiNi 0.5 Co 0.2 Mn 0.3 O 2 /graphite soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 84.5% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (ethyl methyl carbonate), and the mass ratio of ethylene carbonate to ethyl methyl carbonate is 1 :1.
  • the conductive lithium salt is lithium hexafluorophosphate, which accounts for 12.5% of the total mass of the lithium secondary battery electrolyte.
  • the electrolytic solution of this example was applied to a LiNi 0.5 Co 0.2 Mn 0.3 O 2 /silicon carbon soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 82.5% of the total mass of the electrolyte of the lithium secondary battery, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (ethyl methyl carbonate), and the mass ratio of ethylene carbonate and ethyl methyl carbonate is 1 :1.
  • the conductive lithium salt is lithium hexafluorophosphate or lithium bisfluorosulfonimide, which accounts for 10.0% and 4.5% of the total mass of the electrolyte of the lithium secondary battery.
  • N,N-bis(trifluoromethanesulfonyl)aniline accounts for 2.0% of the total mass of the electrolyte, and the additive is triallyl isocyanurate, which accounts for 1.0% of the total mass of the electrolyte.
  • the electrolytic solution of this example was used for a LiNi 0.6 Co 0.2 Mn 0.2 O 2 /graphite soft pack battery.
  • a lithium secondary battery electrolyte is composed of an organic solvent, a conductive lithium salt, a phenyl or pyridyl group-substituted bis(trifluoromethanesulfonyl)amine compound, and an additive.
  • the organic solvent accounts for 85.0% of the total mass of the lithium secondary battery electrolyte, and is composed of a cyclic solvent (ethylene carbonate) and a linear solvent (ethyl methyl carbonate), and the mass ratio of ethylene carbonate and ethyl methyl carbonate is 1 :1.
  • the conductive lithium salt is lithium hexafluorophosphate or lithium bisfluorosulfonimide, which accounts for 8.0% and 3.0% of the total mass of the electrolyte of the lithium secondary battery.
  • N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine accounts for 2.0% of the total mass of the electrolyte
  • the additive is lithium difluorodioxalate phosphate, which accounts for 1.0% of the total mass of the electrolyte.
  • the electrolytic solution of this example was used for a LiNi 0.6 Co 0.2 Mn 0.2 O 2 /graphite soft pack battery.
  • the electrolytic solution of this comparative example was prepared in the same manner as in Example 1, except that N,N-bis(trifluoromethanesulfonyl)aniline was not contained, and this electrolytic solution was applied in the same manner as in Example 1. Test its performance in the battery.
  • the electrolytic solution of this comparative example was prepared in the same manner as in Example 1, except that lithium difluorodioxalate phosphate was not contained, and the electrolytic solution was applied to a battery in the same manner as in Example 1 to test its properties.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 2, except that N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine was not contained, and the electrolytic solution was the same as in Example 2. The same method was applied to the battery to test its performance.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 2, except that the triallyl isocyanurate, 2-propynyl methyl carbonate was not contained, and the electrolytic solution was as in the examples. 2 The same method was applied to the battery to test its performance.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 3, except that N,N-bis(trifluoromethanesulfonyl)aniline was not contained, and this electrolytic solution was applied in the same manner as in Example 3. Test its performance in the battery.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 3, except that lithium difluorodioxalate phosphate and triallyl isocyanurate were not contained, and the electrolytic solution was the same as in Example 3. The method was applied to a battery to test its performance.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 4, except that N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine was not contained, and the electrolytic solution was the same as in Example 4. The same method was applied to the battery to test its performance.
  • the electrolytic solution of this comparative example was prepared in the same manner as in Example 4, except that lithium difluorodioxalate phosphate was not contained, and the electrolytic solution was applied to a battery in the same manner as in Example 4 to test its properties.
  • the electrolytic solution of the present comparative example was prepared in the same manner as in Example 1 except that N,N-bis(trifluoromethanesulfonyl)aniline was replaced with lithium bis(trifluoromethanesulfonyl)imide.
  • the electrolytic solution was applied to a battery to test its performance in the same manner as in Example 1.
  • the electrolytic solution of this comparative example was prepared in the same manner as in Example 4, except that N,N-bis(trifluoromethylsulfonyl)-2-pyridinamine was replaced with bis(trifluoromethanesulfonyl) Lithium amine, this electrolyte was applied to a battery in the same manner as in Example 4 to test its properties.
  • the lithium secondary batteries prepared in the above Examples 1 to 8 and Comparative Examples 1 to 10 were subjected to normal temperature circulation, high temperature storage, and low temperature discharge test.
  • Charge and discharge test conditions In order to measure the charge and discharge performance of the battery using the electrolyte prepared by the present invention, the following operations were carried out: positive and negative electrode sheets were prepared according to a conventional method, and electrolytes prepared in the respective examples were used to inject liquid in a glove box. Pole piece preparation 053048 type soft pack battery, using the Xinwei (BS-9300R type) battery test system to test the charge and discharge of the prepared 053048 type battery, and compare it with the corresponding comparative electrolyte prepared battery. The battery was placed at a normal temperature of 3.0 to 4.2 V at a rate of 1 C for a charge and discharge cycle and placed at 60 ° C for 15 days after full charge storage, and discharged at -20 ° C for 0.5 C. The capacity retention rate of the battery at a normal temperature of 300 cycles, the discharge capacity retention rate after 60 days of full-time storage at 60 ° C, and the discharge capacity retention rate of -20 ° C and 0.5 C were recorded. The results are shown in Table 1.
  • Examples 1-8 are used in combination with the additives in a different ratio of phenyl or pyridyl-substituted bis(trifluoromethanesulfonyl)amine compounds to Comparative Examples 1-8. Both can significantly improve the cycle performance, high temperature storage performance, and low temperature discharge performance of the battery.
  • the battery performance of (trifluoromethanesulfonyl)amine compounds and additives is poor.

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Abstract

La présente invention concerne un électrolyte de batterie secondaire au lithium et une batterie secondaire au lithium associée, l'électrolyte de batterie secondaire au lithium comprenant un solvant organique, un sel de lithium conducteur, un composé de bis(trifluorométhyl sulfonyl) amine substitué par un phényle ou un pyridyle, et un additif. L'électrolyte susmentionné peut améliorer les performances cycliques à température normale, les performances de stockage à haute température et les performances de décharge à basse température de l'électrolyte au moyen d'une combinaison d'un composé bis(trifluorométhyl sulfonyl) amine substitué par un phényle ou par un pyridyle avec un isocyanurate de triallyle et un carbonate de 2-propynyle méthyle.
PCT/CN2018/087900 2018-04-18 2018-05-22 Électrolyte de batterie secondaire au lithium et batterie secondaire au lithium associée WO2019200656A1 (fr)

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CN201810349345.6A CN108539270B (zh) 2018-04-18 2018-04-18 锂二次电池电解液及其锂二次电池
CN201810349345.6 2018-04-18

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