WO2018086378A1 - Électrolyte et batterie secondaire - Google Patents

Électrolyte et batterie secondaire Download PDF

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Publication number
WO2018086378A1
WO2018086378A1 PCT/CN2017/093746 CN2017093746W WO2018086378A1 WO 2018086378 A1 WO2018086378 A1 WO 2018086378A1 CN 2017093746 W CN2017093746 W CN 2017093746W WO 2018086378 A1 WO2018086378 A1 WO 2018086378A1
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Prior art keywords
substituted
carbon atoms
group
unsubstituted
secondary battery
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PCT/CN2017/093746
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English (en)
Chinese (zh)
Inventor
冯俊敏
陈培培
张昌明
周艳
付成华
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宁德时代新能源科技股份有限公司
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Publication of WO2018086378A1 publication Critical patent/WO2018086378A1/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
    • H01M2220/00—Batteries for particular applications
    • H01M2220/30—Batteries in portable systems, e.g. mobile phone, laptop
    • 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 battery technologies, and in particular, to an electrolyte and a secondary battery.
  • a layer of SEI film solid electrolyte interface film
  • This layer of SEI film controls the passage of ions in and out, which is an important factor controlling the reaction kinetics of the electrode.
  • a dense and stable SEI film can ensure the cycle performance of a lithium ion secondary battery, otherwise the SEI film is gradually destroyed as the number of times of charge and discharge increases, so that the organic solvent and the electrode
  • the sheet is subjected to barrier-free contact and chemical and electrochemical reactions occur, so that the organic solvent is consumed indefinitely, resulting in a sudden decrease in the cycle life of the lithium ion secondary battery.
  • the generated SEI film is too thick, and the large impedance causes the lithium ions to fail to migrate, which greatly reduces the capacity retention rate after the lithium ion secondary battery is cycled.
  • the stability of the interface film formed by the positive and negative electrodes during high-temperature storage largely determines the high-temperature storage performance of the lithium ion secondary battery, and has a great influence on the safety performance of the hot-box of the lithium ion secondary battery.
  • an object of the present invention is to provide an electrolyte and a secondary battery, which can effectively improve the normal temperature of a secondary battery when the electrolyte is applied to a secondary battery.
  • the present invention provides an electrolyte comprising: an electrolyte salt, an organic solvent, and an additive.
  • the additive includes one or more of the compounds represented by Formula 1; wherein R 1 is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, and the substituted or unsubstituted carbon atom is 1 An alkoxy group of ⁇ 12, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and R 2 is selected from the group consisting of a substituted or unsubstituted alkylene group having 0 to 6 carbon atoms.
  • R 3 is selected from H, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, and a substituted or unsubstituted carbon atom;
  • the acyloxy group having 1 to 12, the substituted or unsubstituted aryl group having 6 to 10 carbon atoms, the substituted or unsubstituted aryl group having 5 to 10 carbon atoms, and the substituted or unsubstituted carbon atom are One of 1 to 6 nitrile groups;
  • R 4 is selected from H, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted acyloxy group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6
  • the invention provides a secondary battery comprising an electrolyte according to an aspect of the invention.
  • the electrolytic solution of the present invention When the electrolytic solution of the present invention is applied to a secondary battery, the normal temperature and low temperature cycle performance, high temperature storage performance, and hot box safety performance of the secondary battery can be effectively improved.
  • the electrolytic solution according to the first aspect of the invention includes: an electrolyte salt, an organic solvent, and an additive.
  • the additive includes one or more of the compounds represented by Formula 1.
  • R 1 is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, and a substituted or unsubstituted carbon atom.
  • R 2 is selected from one of substituted or unsubstituted alkylene groups having 0 to 6 carbon atoms; and
  • R 3 is selected from H, substituted or unsubstituted carbon atoms.
  • the aryl group having 6 to 10, the substituted or unsubstituted aryl group having 5 to 10 carbon atoms, and the substituted or unsubstituted nitrile group having 1 to 6 carbon atoms; and R 4 are selected from the group consisting of aryl groups having 6 to 10 carbon atoms; H, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted acyloxy group having 1 to 12 carbon atoms a substituted, unsubstituted or substituted aryl group having 6 to 10 carbon atoms
  • the sulfonate structure in the compound represented by Formula 1 can form an alkyl sulfonate having good conductivity in electrochemical redox, thereby being used in a secondary battery
  • the surface of the positive and negative electrodes forms a low-impedance, organic-inorganic composite protective film.
  • the double bond structure in the compound represented by Formula 1 contributes to the formation of a denser polymer protective film on the surface of the positive and negative electrodes, so that the secondary battery has good cycle performance.
  • -CN in the compound of Formula 1 can complex with a transition metal ion on the surface of the positive electrode, and the resulting complex adheres to the surface of the positive electrode to form a stable CEI protective film, thereby significantly improving the high temperature storage of the secondary battery. performance. Therefore, by adding the compound represented by Formula 1 to the electrolyte, an interface protective film having a small impedance and a uniform density can be formed on the surface of the positive and negative electrodes, thereby improving the stability of the electrolyte and the dynamic properties of the electrode piece, thereby Secondary battery is high Good performance at low temperatures, specifically, can effectively improve the normal temperature and low temperature cycle performance of the secondary battery, high temperature storage performance and hot box safety performance.
  • R 2 is selected from an alkylene group having 0 carbon atoms, it means that the double bond carbon atom in the formula 1 is directly bonded to the oxygen atom in the sulfonate structure. Specifically, it can be expressed by Formula 2.
  • the alkyl group having 1 to 12 carbon atoms may be a chain alkyl group or a cycloalkyl group, and hydrogen at a ring of the cycloalkyl group may be used. Replaced by an alkyl group.
  • the lower limit of the number of carbon atoms in the alkyl group is preferably 2, 3, 4, and 5.
  • the preferred upper limit is 3, 4, 5, 6, 8, and 10.
  • an alkyl group having 1 to 10 carbon atoms is selected, and more preferably, a chain alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms is selected, and still more preferably, A chain alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 7 carbon atoms is selected.
  • the alkyl group having 1 to 12 carbon atoms may be selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl Base, isopentyl, neopentyl, hexyl, 2-methyl-pentyl, 3-methyl-pentyl, 1,1,2-trimethyl-propyl, 3,3,-dimethyl- One of butyl, heptyl, 2-heptyl, 3-heptyl, 2-methylhexyl, 3-methylhexyl, isoheptyl, octyl, decyl, fluorenyl.
  • the alkoxy group having 1 to 12 carbon atoms is preferably an alkoxy group having 1 to 10 carbon atoms, and more preferably, the number of carbon atoms is selected. It is more preferably an alkoxy group having 1 to 6 carbon atoms, and still more preferably an alkoxy group having 1 to 4 carbon atoms.
  • the alkoxy group having 1 to 12 carbon atoms may be selected from the group consisting of a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a sec-butoxy group, and a t-butoxy group.
  • the acyloxy group having 1 to 12 acyloxy groups is preferably an acyloxy group having 1 to 10 carbon atoms, and more preferably, the number of carbon atoms is selected.
  • the acyloxy group of 1 to 6 is more preferably an acyloxy group having 1 to 4 carbon atoms.
  • the carbonyl group having 1 to 12 acyloxy groups may be selected from the group consisting of formyloxy, acetoxy, n-propionyloxy, isopropionyloxy, n-butyryloxy, and sec-butyryloxy. , tert-butyryloxy, n-pentanoyloxy, isovaleryloxy One of them.
  • the alkylene group having 1 to 6 carbon atoms may be a linear alkylene group or a branched alkylene group.
  • the lower limit of the number of carbon atoms in the alkylene group having 1 to 6 carbon atoms is preferably 2, 3, 4 or 5, and the preferred upper limit is 3, 4, 5 or 6.
  • the alkylene group having 1 to 6 carbon atoms may be selected from the group consisting of methylene, ethylene, propylene, isopropylidene, butylene, isobutylene, sec-butylene, and sub- One of a pentyl group and a hexylene group.
  • the aryl group having 6 to 10 carbon atoms may be a phenyl group, a phenylalkyl group or an alkylphenyl group.
  • the aryl group having a carbon number of 6 to 10 may be selected from one of a phenyl group, a benzyl group, a p-tolyl group, an o-tolyl group, and an m-tolyl group.
  • the aryl group having 5 to 10 carbon atoms may be selected from the group consisting of a furyl group, a thienyl group, a pyrrolyl group, a thiazolyl group, an imidazolyl group, a pyridyl group, and a pyrazine.
  • a furyl group a thienyl group
  • a pyrrolyl group a thiazolyl group
  • an imidazolyl group a pyridyl group
  • a pyrazine a group having 5 to 10 carbon atoms
  • a pyrazine a group having 5 to 10 carbon atoms.
  • the substituent for carrying out the substitution may be selected from one or more of -CN, F, Cl, Br, I.
  • the compound represented by Formula 1 is selected from one or more of the following compounds;
  • the mass of the compound represented by Formula 1 is from 0.1% to 15% by mass based on the total mass of the electrolytic solution.
  • the upper limit of the compound represented by Formula 1 is 5%, 6%, 7%, 8%, 9%, and 10%
  • the lower limit of the compound represented by Formula 1 is 0.2%, 0.5%, 1%, 2 %, 3%.
  • the mass of the compound represented by Formula 1 is from 1% to 10% by mass based on the total mass of the electrolyte.
  • the mass of the compound represented by Formula 1 is 3% to 7% of the total mass of the electrolytic solution.
  • the mass of the compound represented by Formula 1 is 3% of the total mass of the electrolyte.
  • the organic solvent is selected from the group consisting of dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC), and ethyl methyl carbonate (EMC).
  • DMC dimethyl carbonate
  • DEC diethyl carbonate
  • EMC ethyl methyl carbonate
  • EMC ethyl methyl carbonate
  • the organic solvent may further include different classes of ionic liquids and the like.
  • the organic solvent used in the present invention may be used alone or in combination of two or more kinds in any combination and in any ratio depending on the application.
  • the organic solvent is preferably propylene carbonate (PC), ethylene carbonate (EC), or carbonic acid from the viewpoints of electrochemical stability of its redox and chemical stability associated with heat and reaction of the above solute.
  • PC propylene carbonate
  • EC ethylene carbonate
  • CO acid carbonic acid from the viewpoints of electrochemical stability of its redox and chemical stability associated with heat and reaction of the above solute.
  • DEC ethyl ester
  • DMC dimethyl carbonate
  • EMC ethyl methyl carbonate
  • the concentration of the electrolyte salt is from 0.5 mol/L to 2.5 mol/L, preferably, the concentration of the electrolyte salt is from 0.7 mol/L to 2.0 mol/L. Further preferably, the concentration of the electrolyte salt is from 0.9 mol/L to 1.5 mol/L.
  • concentration of the electrolyte salt is less than 0.5 mol/L, the ionic conductivity of the electrolytic solution is lowered, so that the cycle performance and the electrical conductivity of the secondary battery tend to be lowered.
  • the additive may further include fluoroethylene carbonate and/or adiponitrile.
  • a secondary battery according to a second aspect of the invention which comprises the electrolytic solution of the first aspect of the invention.
  • the secondary battery further includes a positive electrode sheet, a negative electrode sheet, and a separator.
  • the positive electrode sheet includes a positive electrode current collector and a positive electrode active slurry layer on the positive electrode current collector, wherein the positive electrode active slurry layer includes a positive electrode active layer material.
  • the specific type of the positive electrode active material is not particularly limited and can be selected according to requirements.
  • the negative electrode sheet includes a negative electrode current collector and a negative electrode active slurry layer on the negative electrode current collector.
  • the negative active slurry layer includes a negative active material.
  • the specific type of the negative active material is not particularly limited and can be selected according to requirements.
  • the specific kind of the separator is not particularly limited, and may be any separator material used in the existing secondary battery, such as polyethylene, polypropylene, poly Vinylidene fluoride and their multilayer composite films are not limited to these.
  • the secondary battery may be a lithium ion secondary battery, a sodium ion secondary battery, or a zinc ion secondary battery.
  • the electrolyte salt may be a lithium salt
  • the lithium salt may be selected from the group consisting of LiPF 6 , LiBF 4 , LiClO 4 , LiAsF 6 , LiSbF 6 , LiCF 3 SO 3 , LiN ( CF 3 SO 2 ) 2 , LiN(FSO 2 ) 2 , LiN(C 2 F 5 SO 2 ) 2 , LiN(CF 3 SO 2 )(C 4 F 9 SO 2 ), LiC(CF 3 SO 2 ) 3 , LiPF 3 (C 3 F 7 ) 3 , LiB(CF 3 ) 4 , LiBF 3 (C 2 F 5 ), LiPO 2 F 2 , LiPF 4 (C 2 O 4 ), LiPF 2 (C 2 O 4 ) 2 , One or more of LiBF 2 (C 2 O 4 ) and LiB(C 2 O 4 ) 2 .
  • LiPF 6 is added as an essential component.
  • the compound 1 used was prepared as follows:
  • the lithium ion secondary batteries of Examples 1 to 24 and Comparative Examples 1 to 5 were each prepared in the following manner.
  • the positive electrode active material lithium cobaltate (LiCoO 2 ), the binder polyvinylidene fluoride, and the conductive agent acetylene black are mixed at a weight ratio of 94:3:3, and N-methylpyrrolidone (NMP) is added under the action of a vacuum mixer.
  • NMP N-methylpyrrolidone
  • the negative active material artificial graphite, the conductive agent acetylene black, the binder styrene-butadiene rubber (SBR), and the thickener sodium carboxymethyl cellulose (CMC) are mixed at a weight ratio of 95:2:2:1, and deionized.
  • Water, the negative electrode slurry was obtained under the action of a vacuum mixer; the negative electrode slurry was uniformly coated on the negative electrode current collector copper foil having a thickness of 8 ⁇ m; the copper foil was air-dried at room temperature, transferred to an oven at 120 ° C for 1 hour, and then cooled.
  • the negative electrode sheet was obtained by pressing and slitting.
  • the specific types and contents of the additives used in the electrolyte are shown in Table 1. In Table 1, the content of the additive is a mass percentage calculated based on the total mass of the electrolyte.
  • PE polyethylene
  • the positive electrode sheet, the separator film and the negative electrode sheet are stacked in order, so that the separator is in a role of isolation between the positive and negative electrode sheets, and then wound to obtain a bare cell; the bare cell is placed in the outer packaging foil, The prepared electrolyte solution is injected into the dried bare cell, and subjected to vacuum encapsulation, standing, formation, shaping, and the like to obtain a lithium ion secondary battery.
  • the lithium ion secondary battery was charged at a constant current of 0.5 C to a voltage of 4.45 V at 0 ° C and 25 ° C, respectively, and further charged at a constant voltage of 4.45 V until the current was 0.05 C, and then discharged at a constant current of 0.5 C to a voltage of 3.0V, this is a charge and discharge cycle process, this discharge capacity is the discharge capacity of the first cycle.
  • the lithium ion secondary battery was subjected to 300 cycles of charge/discharge test in accordance with the above method.
  • the capacity retention ratio (%) of the lithium ion secondary battery after N times of cycle (discharge capacity N times of discharge / discharge capacity of first cycle) ⁇ 100%.
  • the lithium ion secondary battery was charged at a constant current of 1 C to a voltage of 4.45 V at 25 ° C, and then charged at a constant voltage of 4.45 V until the current was 0.05 C. At this time, the volume of the lithium ion secondary battery was tested and recorded as V 0 . Then, the lithium ion secondary battery was placed in an incubator at 60 ° C, and stored for 10 days, 20 days, and 30 days, respectively, and the volume of the lithium ion secondary battery was measured and recorded as V n .
  • the volume expansion ratio of the lithium ion secondary battery after storage for n days at 60 ° C [(V n - V 0 ) / V 0 ] ⁇ 100%, where n is the number of days in which the lithium ion secondary battery is stored.
  • the lithium ion secondary battery was charged at a constant current of 1 C to a voltage of 4.45 V at 25 ° C, further charged at a constant voltage of 4.45 V until the current was 0.05 C, the charging was stopped, and the lithium ion secondary battery was placed in a hot box.
  • the temperature of the hot box was raised from 25 ° C to 130 ° C at a rate of 5 ° C / min. After the temperature reached 130 ° C, the temperature was maintained unchanged, and the timing was started. The state of the lithium ion secondary battery was observed after 1 h. Five lithium ion secondary batteries were tested in each group.
  • the standard for the lithium ion secondary battery to pass the test is: no smoke, no fire, no explosion.
  • Comparative Example 1 did not contain any additives, and the normal temperature cycle performance, low temperature cycle performance, high temperature storage performance, and hot box safety performance of the lithium ion secondary battery were inferior.
  • Example 1 When the compound of Formula 1 was added to the electrolytic solution (Examples 1 to 15), the room temperature cycle performance, low-temperature cycle performance, high-temperature storage property, and hot box safety performance of the lithium ion secondary battery were all improved.
  • Formula 1 is a fluorinated compound
  • the fluorine atom increases the oxidation potential of Formula 1 so that it is not easily oxidized, so the performance of the lithium ion secondary battery is superior to that of other compounds.
  • Example 13 since the structure of Formula 1 contains two benzene rings, the viscosity of the electrolytic solution is slightly large, resulting in a slow migration rate of lithium ions, and thus the performance of the lithium ion secondary battery is slightly inferior to those of other compounds.
  • Comparative Example 4 fluoroethylene carbonate was separately added to the electrolytic solution, compared to Comparative Example 1, The cycle performance of the lithium ion secondary battery is improved, but the high temperature storage performance and the heat box safety performance are still poor.
  • Comparative Example 5 adiponitrile was separately added to the electrolytic solution, and the high-temperature storage performance and the heat box safety performance of the lithium ion secondary battery were improved as compared with Comparative Example 1, but the cycle performance was still poor.
  • Examples 16 to 24 when fluoroethylene carbonate and/or adiponitrile were further added to the electrolytic solution, the overall performance of the lithium ion secondary battery was further improved.

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Abstract

L'invention concerne un électrolyte et une batterie secondaire. L'électrolyte comprend : un sel d'électrolyte, un solvant organique, et un additif. L'additif comprend un ou plusieurs composés tels qu'exprimés dans la Formule (1). Après application sur une batterie secondaire, l'électrolyte peut améliorer efficacement les performances de cycle de charge de la batterie secondaire dans une température ambiante et une basse température, et améliorer les performances de stockage d'énergie dans une température élevée performance sécurité dans une chambre de test à contrainte thermique.
PCT/CN2017/093746 2016-11-10 2017-07-20 Électrolyte et batterie secondaire WO2018086378A1 (fr)

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CN201610988819.2 2016-11-10
CN201610988819.2A CN108075187B (zh) 2016-11-10 2016-11-10 电解液及二次电池

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WO2018086378A1 true WO2018086378A1 (fr) 2018-05-17

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CN111916824A (zh) * 2020-06-30 2020-11-10 珠海冠宇电池股份有限公司 一种锂离子电池用非水电解液及使用该非水电解液的锂离子电池
CN114097126A (zh) * 2020-03-26 2022-02-25 宁德新能源科技有限公司 改善电池循环性能的方法和电子装置
EP3958369A4 (fr) * 2019-08-30 2022-07-20 LG Energy Solution, Ltd. Solution électrolytique non aqueuse et batterie secondaire au lithium la comprenant

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KR20210026503A (ko) * 2019-08-30 2021-03-10 주식회사 엘지화학 이차전지용 전해액 첨가제, 이를 포함하는 비수 전해액 및 리튬 이차전지
CN113948779B (zh) * 2021-12-21 2022-03-22 浙江金羽新能源科技有限公司 含添加剂的锌离子电池电解液及其制备方法和锌离子电池

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Publication number Priority date Publication date Assignee Title
EP3958369A4 (fr) * 2019-08-30 2022-07-20 LG Energy Solution, Ltd. Solution électrolytique non aqueuse et batterie secondaire au lithium la comprenant
CN114097126A (zh) * 2020-03-26 2022-02-25 宁德新能源科技有限公司 改善电池循环性能的方法和电子装置
CN111916824A (zh) * 2020-06-30 2020-11-10 珠海冠宇电池股份有限公司 一种锂离子电池用非水电解液及使用该非水电解液的锂离子电池
CN111916824B (zh) * 2020-06-30 2021-11-09 珠海冠宇电池股份有限公司 一种锂离子电池用非水电解液及使用该非水电解液的锂离子电池
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