WO2024166499A1 - 二次電池 - Google Patents

二次電池 Download PDF

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Publication number
WO2024166499A1
WO2024166499A1 PCT/JP2023/042550 JP2023042550W WO2024166499A1 WO 2024166499 A1 WO2024166499 A1 WO 2024166499A1 JP 2023042550 W JP2023042550 W JP 2023042550W WO 2024166499 A1 WO2024166499 A1 WO 2024166499A1
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Prior art keywords
battery
evaluation test
electrolyte
positive electrode
negative electrode
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English (en)
French (fr)
Japanese (ja)
Inventor
晶暉 山上
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Murata Manufacturing Co Ltd
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Murata Manufacturing Co Ltd
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Priority to CN202380082621.6A priority Critical patent/CN120283320A/zh
Priority to JP2024576129A priority patent/JP7798210B2/ja
Publication of WO2024166499A1 publication Critical patent/WO2024166499A1/ja
Priority to US19/224,119 priority patent/US20250293304A1/en
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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
    • 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
    • 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
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • H01M2300/0034—Fluorinated solvents
    • 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 a secondary battery.
  • LiFSI lithium bis(fluorosulfonyl)imide
  • Patent Document 1 describes the addition of asymmetric borate esters, asymmetric phosphate esters, etc. to the electrolyte in order to suppress corrosion of the current collector, etc., by LiFSI.
  • the present invention was made in consideration of the above problems, and aims to provide a secondary battery that can be stably charged and discharged while suppressing corrosion of the current collector, etc., caused by lithium bis(fluorosulfonyl)imide.
  • a secondary battery according to one embodiment of the present invention is a secondary battery having a positive electrode, a negative electrode, a separator, and an electrolyte solution, the electrolyte solution containing an acetamide derivative represented by formula (1) and lithium bis(fluorosulfonyl)imide.
  • R1 and R2 each independently represent an alkyl group or alkoxy group having 1 to 5 carbon atoms, which may have a substituent, or a trimethylsilyl group, and R1 and R2 may be bonded to each other to form a condensed ring.
  • the present invention provides a secondary battery that can be stably charged and discharged while suppressing corrosion of the current collector, etc., caused by lithium bis(fluorosulfonyl)imide.
  • FIG. 1 is a cross-sectional view showing an example of a secondary battery according to this embodiment.
  • FIG. 2 is an enlarged view of region A in FIG.
  • FIG. 3 is a cutaway view showing another example of the secondary battery according to the present embodiment.
  • FIG. 4 is a schematic cross-sectional view taken along line VI-VI in FIG.
  • Fig. 1 is a cross-sectional view showing an example of a secondary battery according to the present embodiment.
  • the secondary battery 1 shown in Fig. 1 is a cylindrical lithium-ion secondary battery.
  • the secondary battery 1 includes a casing 10 and an electrode assembly 200.
  • the casing 10 is a case that houses the electrode body 200 and an electrolyte (not shown).
  • the casing 10 includes a battery can 11, a lid 12, a thermosensitive resistor element 13, a safety valve mechanism 14, a gasket 15, a positive electrode lead 16, a negative electrode lead 17, a center pin 19, and an insulating plate 18.
  • the battery can 11 is a cylindrical member that includes an end face that serves as the negative electrode of the secondary battery 1.
  • the battery can 11 is a cylinder with one end face that is closed and the other end face that is open.
  • the battery can 11 is a conductor, and is made of, for example, iron (Fe) whose surface is plated with nickel (Ni).
  • the lid 12 is a disk-shaped member that includes a protrusion that serves as the positive electrode of the secondary battery 1.
  • the lid 12 is provided on the open end surface of the battery can 11.
  • the lid 12 is made of a conductor, for example, made of the same material as the battery can 11.
  • the direction in which the cylindrical portion of the battery can 11 extends may be described as the length direction of the secondary battery 1.
  • the positive pole of the secondary battery 1 refers to the protrusion of the lid 12, and the negative pole of the secondary battery 1 refers to the closed end surface of the battery can 11.
  • the thermal resistance element 13 is an element whose resistance increases with an increase in temperature.
  • the thermal resistance element 13 is provided on the negative pole side of the lid body 12. When the secondary battery 1 becomes hot due to a short circuit or the like, the resistance of the thermal resistance element 13 increases and limits the current.
  • the safety valve mechanism 14 is a mechanism whose shape changes according to the gas pressure inside the casing 10.
  • the safety valve mechanism 14 is provided on the negative pole side of the thermosensitive resistor 13.
  • the safety valve mechanism 14 is electrically connected to the lid 12 via the thermosensitive resistor 13.
  • the safety valve mechanism 14 has a protrusion on the negative pole side, and when the gas pressure inside the casing 10 is normal, it contacts and is electrically connected to the positive electrode lead 16 via the protrusion.
  • the protrusion of the safety valve mechanism 14 reverses to the positive pole side and moves away from the positive electrode lead 16. This electrically disconnects the positive electrode lead 16 from the lid 12.
  • the gasket 15 is an annular member that secures the lid 12, the thermal resistor element 13, and the safety valve mechanism 14 to the battery can 11.
  • the gasket 15 is provided on the open end face of the battery can 11.
  • the gasket 15 tightly attaches the battery can 11 and the lid 12 to make the inside of the casing 10 airtight.
  • the gasket 15 is an insulator.
  • the positive electrode lead 16 is a terminal connected to the positive electrode 210 of the electrode body 200 described below.
  • the positive electrode lead 16 is electrically connected to the lid body 12 via the safety valve mechanism 14 and the thermosensitive resistor element 13.
  • the positive electrode lead 16 is a conductor, and is made of, for example, aluminum.
  • the negative electrode lead 17 is a terminal that is connected to the negative electrode 220 of the electrode body 200, which will be described later.
  • the negative electrode lead 17 is electrically connected to the battery can 11.
  • the negative electrode lead 17 is a conductor, and is made of, for example, nickel.
  • the insulating plate 18 is an insulating plate-shaped member. One insulating plate 18 is provided to cover each of the positive electrode side of the secondary battery 1 and the negative electrode side of the secondary battery 1 of the electrode body 200 described below.
  • the center pin 19 is provided on the central axis of the electrode body 200.
  • the center pin 19 is a linear member having a length in the longitudinal direction of the secondary battery 1.
  • the material of the center pin 19 is not particularly limited, and is, for example, a metal.
  • the electrode body 200 includes a positive electrode 210, a negative electrode 220, and a separator 230.
  • the electrode body 200 has a structure in which the positive electrode 210 and the negative electrode 220 are stacked with the separator 230 interposed therebetween.
  • the electrode body 200 is provided inside the battery can 11 and has a structure in which it is wound around the center pin 19.
  • the positive electrode 210, the negative electrode 220, and the separator 230 are stacked in the radial direction of the secondary battery 1 with the center pin 19 at the center.
  • the positive electrode 210 and the negative electrode 220 included in the electrode body 200 are layered members for the charge/discharge reaction of the secondary battery according to this embodiment.
  • the positive electrode 210 includes a positive electrode collector layer 211 and a positive electrode active material layer 212.
  • the positive electrode collector layer 211 is laminated between the positive electrode active material layers 212.
  • the positive electrode collector layer 211 is a conductive layer, and may be made of, for example, aluminum foil.
  • the positive electrode active material layer 212 is a layer containing a positive electrode active material.
  • the positive electrode active material layer 212 contains a positive electrode active material, a binder, and a conductive additive.
  • the positive electrode active material layer 212 is not limited to the materials listed above, and may further contain, for example, a dispersant.
  • the positive electrode active material is preferably a lithium-containing compound such as a lithium-containing composite oxide or a lithium-containing phosphate compound.
  • the lithium-containing composite oxide is an oxide containing lithium and one or more elements other than lithium as constituent elements.
  • the lithium-containing composite oxide has, for example, a layered rock salt type or a spinel type crystal structure.
  • lithium -containing composite oxides include LiNiO2 , LiCoO2 , LiCo0.98Al0.01Mg0.01O2 , LiNi0.5Co0.2Mn0.3O2 , LiNi0.8Co0.15Al0.05O2 , LiNi0.33Co0.33Mn0.33O2 , Li1.2Mn0.52Co0.175Ni0.1O2 , Li1.15 ( Mn0.65Ni0.22Co0.13 ) O2 , LiMn2O4 , and the like .
  • the lithium-containing phosphate compound is a phosphate compound that contains lithium and one or more elements other than lithium as constituent elements.
  • the lithium-containing phosphate compound has, for example, an olivine type crystal structure.
  • Specific examples of the lithium-containing phosphate compound include LiFePO4 , LiMnPO4 , LiFe0.5Mn0.5PO4 , LiFe0.3Mn0.7PO4 , etc.
  • the binder contained in the positive electrode active material layer 212 may be any material, and may include, for example, one or more of synthetic rubber and polymer compounds.
  • synthetic rubber include styrene butadiene rubber, fluorine-based rubber, and ethylene propylene diene.
  • polymer compounds include polyvinylidene fluoride and polyimide.
  • the conductive assistant contained in the positive electrode active material layer 212 may be any material, and may include, for example, carbon. Examples of carbon include graphite, carbon black, acetylene black, and ketjen black. However, the conductive assistant is not limited to these materials, and may be a metal material, a conductive polymer, or the like, as long as it is a material that is conductive.
  • the negative electrode 220 includes a negative electrode collector layer 221 and a negative electrode active material layer 222.
  • the negative electrode collector layer 221 is laminated between the negative electrode active material layers 222.
  • the negative electrode collector layer 221 is a conductor, and may be made of, for example, copper foil.
  • the negative electrode active material layer 222 is a layer containing a negative electrode active material.
  • the negative electrode active material layer 222 is not limited to being composed of only a negative electrode active material, and may contain, for example, a conductive additive and a binder.
  • the negative electrode active material includes materials capable of absorbing and releasing lithium, such as carbon materials, metals, semimetals, silicon alloys or compounds, and tin (Sn) alloys or compounds.
  • Carbon materials that can be used as the negative electrode active material include, for example, graphite, non-graphitizable carbon, and easily graphitizable carbon. More specifically, carbon materials include, for example, pyrolytic carbons, cokes, glassy carbon fiber, organic polymer compound sintered bodies, activated carbon, and carbon blacks. Cokes include pitch coke, needle coke, and petroleum coke.
  • organic polymer compound sintered bodies are made by sintering polymer compounds such as phenol resin and furan resin at an appropriate temperature and carbonizing them.
  • Metals and semimetals that can be used as negative electrode active materials include, for example, tin, lead (Pb), aluminum, indium (In), silicon, zinc (Zn), antimony (Sb), bismuth (Bi), cadmium (Cd), magnesium (Mg), boron (B), gallium (Ga), germanium (Ge), arsenic (As), silver (Ag), zirconium (Zr), yttrium (Y), and hafnium (Hf).
  • silicon, germanium, tin, and lead are preferred. Silicon and tin are more preferred because they have a high ability to absorb and release lithium and can provide a high energy density.
  • Silicon alloys that can be used as the negative electrode active material include, for example, those containing at least one of the group consisting of tin, nickel, copper (Cu), iron (Fe), cobalt (Co), manganese (Mn), zinc, indium, silver, titanium (Ti), germanium, bismuth, antimony, and chromium (Cr) as a second constituent element other than silicon.
  • Silicon compounds that can be used as the negative electrode active material include, for example, those containing oxygen (O) or carbon (C), and may contain the above-mentioned second constituent element in addition to silicon.
  • Tin alloys that can be used as the negative electrode active material include, for example, those that contain at least one of the group consisting of silicon, nickel, copper, iron, cobalt, manganese, zinc, indium, silver, titanium, germanium, bismuth, antimony, and chromium as a second constituent element other than tin.
  • Tin compounds that can be used as the negative electrode active material include, for example, those that contain oxygen or carbon, and may contain the above-mentioned second constituent element in addition to tin.
  • the separator 230 is a film that insulates the positive electrode 210 and the negative electrode 220.
  • the separator 230 is laminated between the positive electrode 210 and the negative electrode 220 so that the positive electrode 210 and the negative electrode 220 do not come into direct contact with each other.
  • the material of the separator 230 is preferably electrically stable, chemically stable with respect to the positive electrode active material, the negative electrode active material, and the electrolyte, and has insulating properties.
  • the separator 230 may be, for example, a polymer nonwoven fabric, a porous film, or a layer made of glass or ceramic fibers. It is more preferable that the material of the separator 230 contains a porous polyolefin film.
  • the separator 230 may be made of multiple layers, or may be a composite of a porous polyolefin film and a heat-resistant film containing polyimide, glass, or ceramic fibers.
  • the electrolyte is an electrolyte that fills the space surrounded by the insulating plate 18 and the battery can 11.
  • the electrolyte contains, for example, an electrolyte salt and a solvent that dissolves the electrolyte salt.
  • the electrolyte salt contains lithium bis(fluorosulfonyl)imide (LiN(SO 2 F 2 ) 2 ). This can improve the charge/discharge characteristics.
  • the electrolyte salt may contain other electrolyte salts used as electrolyte salts for lithium ion batteries.
  • the mass of the other electrolyte salt is preferably 1 ⁇ 3 or less, more preferably 1 ⁇ 4 or less, of the mass of lithium bis(fluorosulfonyl)imide (LiN(SO 2 F 2 ) 2 ).
  • the other electrolyte salt is, for example, a light metal salt such as a lithium salt.
  • lithium salts include lithium hexafluorophosphate (LiPF 6 ), lithium tetrafluoroborate (LiBF 4 ), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), lithium bis(trifluoromethanesulfonyl)imide (LiN(CF 3 SO 2 ) 2 ), lithium tris(trifluoromethanesulfonyl)methide (LiC(CF 3 SO 2 ) 3 ), lithium bis(oxalato)borate (LiB(C 2 O 4 ) 2 ), lithium monofluorophosphate (Li 2 PFO 3 ), and lithium difluorophosphate (LiPF 2 O 2 ).
  • LiPF 6 lithium hexafluorophosphate
  • LiBF 4 lithium tetrafluoroborate
  • LiCF 3 SO 3 lithium trifluoromethanesulfonate
  • LiN(CF 3 SO 2 ) 2 lithium trifluoromethanesulfony
  • the solvent contains an acetamide derivative represented by formula (1), which can suppress corrosion of the positive electrode current collector layer 211 and the like caused by lithium bis(fluorosulfonyl)imide.
  • R1 and R2 each independently represent an alkyl group or alkoxy group having 1 to 5 carbon atoms, which may have a substituent, or a trimethylsilyl group, and R1 and R2 may be bonded to each other to form a condensed ring.
  • the term "optionally having a substituent” means that the group has no substituent or that a hydrogen group is substituted with one or more substituents. Examples of the substituent include a hydrocarbon group and a halogen group such as a fluorine group.
  • Examples of the compound represented by formula (1) include compounds represented by formulas (1-1) to (1-5).
  • the molar ratio of the acetamide derivative to lithium bis(fluorosulfonyl)imide is 2 or more and 4 or less.
  • the molar ratio is 2 or more, corrosion of the positive electrode collector layer 211 and the like by lithium bis(fluorosulfonyl)imide can be effectively suppressed.
  • the viscosity of the electrolyte is reduced, thereby improving the discharge rate characteristics.
  • the solvent may contain other non-aqueous solvents used as electrolyte salts in lithium ion batteries.
  • the mass of the other non-aqueous solvent is preferably 1/3 or less, more preferably 1/4 or less, of the mass of the acetamide derivative represented by formula (1).
  • the other non-aqueous solvents include esters, ethers, and the like. More specifically, the other non-aqueous solvents include carbonate ester compounds, carboxylate ester compounds, lactone compounds, and the like.
  • the carbonate ester compounds are cyclic carbonate esters, chain carbonate esters, and the like. Specific examples of cyclic carbonate esters are ethylene carbonate, propylene carbonate, and the like.
  • chain carbonate esters are dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and the like.
  • the carboxylate ester compounds are chain carboxylate esters, and the like. Specific examples of chain carboxylate esters are methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, propyl propionate, methyl trimethyl acetate, ethyl trimethyl ethyl acetate, methyl butyrate, ethyl butyrate, and the like.
  • the lactone compounds are lactones, and the like. Specific examples of lactones include ⁇ -butyrolactone and ⁇ -valerolactone.
  • ethers include 1,2-dimethoxyethane, tetrahydrofuran, 1,3-dioxolane, and 1,4-dioxane.
  • Ethers may be compounds in which some or all of the hydrogen atoms are replaced with fluorine, such as 1,1,2-tetrafluoroethyl 2,2,2,3,3-tetrafluoropropyl ether.
  • the electrolyte may contain substances other than the electrolyte salt and the solvent, such as additives.
  • the mass of the substances other than the electrolyte salt and the solvent is preferably 0.1% by mass or more and 20% by mass or less relative to the mass of the electrolyte salt and the solvent additive.
  • the electrolyte preferably further contains at least one additive selected from the group consisting of unsaturated cyclic carbonates such as vinylene carbonate, 4-methylene-1,3-dioxolan-2-one (methylene ethylene carbonate), and vinylethylene carbonate, and halogenated cyclic carbonates such as fluoroethylene carbonate (monofluoroethylene carbonate) and difluoroethylene carbonate.
  • unsaturated cyclic carbonates such as vinylene carbonate, 4-methylene-1,3-dioxolan-2-one (methylene ethylene carbonate), and vinylethylene carbonate
  • halogenated cyclic carbonates such as fluoroethylene carbonate (monofluoroethylene carbonate) and difluoroethylene carbonate.
  • the additives are not limited to those listed above, and may be other additives.
  • the other additives are not particularly limited, but may be, for example, sulfonic acid esters, phosphate esters, acid anhydrides, isocyanates, etc.
  • sulfonic acid esters include propane sultone and propene sultone.
  • phosphate esters include trimethyl phosphate and triethyl phosphate.
  • acid anhydrides include succinic anhydride, 1,2-ethane disulfonic anhydride, and 2-sulfobenzoic anhydride.
  • Specific examples of isocyanates include hexamethylene diisocyanate, etc.
  • the electrolyte preferably further contains a hydrofluoroether as an additive.
  • hydrofluoroethers include 1,1,2,2-tetrafluoroethyl 2,2,3,3-tetrafluoropropyl ether. This reduces the viscosity of the electrolyte, improving the ionic conductivity of the electrolyte, thereby further improving the discharge rate characteristics.
  • FIG. 3 is a cutaway view showing a different example of a secondary battery according to this embodiment.
  • the secondary battery 1A shown in FIG. 3 is a laminated lithium-ion secondary battery.
  • the secondary battery 1A includes a battery element 20, an exterior member 31, and an adhesive material 32.
  • FIG. 4 is a schematic diagram of a cross section taken along line VI-VI in FIG. 3.
  • the battery element 20 is provided inside the exterior member 31.
  • the battery element 20 includes an electrode body 200A, a positive electrode lead 21, a negative electrode lead 22, and a protective material 23.
  • the positive electrode lead 21 is a terminal drawn from inside the battery element 20 to the outside of the exterior member 31. That is, the positive electrode lead 21 is a terminal that serves as the positive electrode of the secondary battery 1A.
  • the positive electrode lead 21 is provided near the center of the battery element 20.
  • the negative electrode lead 22 is a terminal drawn from inside the battery element 20 to the outside of the exterior member 31. That is, the negative electrode lead 22 is a terminal that serves as the negative electrode of the secondary battery 1A.
  • the negative electrode lead 22 is provided near the center of the battery element 20.
  • the protective material 23 is a member that protects the outside of the battery element 20.
  • the protective material 23 is provided so as to wrap around the electrode body 200A.
  • the protective material 23 is, for example, an insulating tape.
  • the exterior member 31 is a case in which the battery element 20 is housed.
  • the exterior member 31 includes an insulating layer, a metal layer, and an outermost layer.
  • the exterior member 31 is structured such that the insulating layer, the metal layer, and the outermost layer are laminated in this order from the inside, i.e., from the side where the battery element 20 is provided, and then pasted together by lamination or the like.
  • the insulating layer of the exterior member 31 is made of a resin such as polyethylene, polypropylene, modified polyethylene, modified polypropylene, or a polyolefin resin containing ethylene or propylene as a monomer. This allows the exterior member 31 to reduce the moisture permeability of the secondary battery 1A and improve its airtightness.
  • the metal layer of the exterior member 31 is a metal plate material or foil material such as aluminum, stainless steel, nickel, or iron.
  • the outermost layer may be made of any material, but is preferably made of a material that is highly resistant to tearing, punctures, etc., such as the same resin as the insulating layer, or nylon.
  • the adhesive 32 is a member for making the exterior member 31 airtight.
  • the adhesive 32 is provided between the exterior member 31 and the positive electrode lead 21 and the negative electrode lead 22. It is preferable that the material of the adhesive 32 has adhesion to the positive electrode lead 21 and the negative electrode lead 22.
  • the adhesive 32 is made of a polyolefin resin such as polyethylene, polypropylene, modified polyethylene, or modified polypropylene. As a result, the adhesive 32 can seal the gap between the exterior member 31 and the positive electrode lead 21 and the negative electrode lead 22, making the interior of the exterior member 31 airtight.
  • the electrode body 200A is a laminate for the charge/discharge reaction of the secondary battery according to this embodiment.
  • the electrode body 200A includes a positive electrode 210A having a positive electrode collector layer 211A and a positive electrode active material layer 212A, a negative electrode 220A having a negative electrode collector layer 221A and a negative electrode active material layer 222A, and a separator 230A.
  • the electrode body 200A has a structure wound around the positive electrode lead 21 and the negative electrode lead 22, and is laminated in the following order from the outside, i.e., from the protective material 23 side: the negative electrode collector layer 221A, the negative electrode active material layer 222A, the separator 230A, the positive electrode active material layer 212A, the positive electrode collector layer 211A, the positive electrode active material layer 212A, the separator 230A, and the negative electrode active material layer 222A.
  • no layers other than the negative electrode collector layer 221A, the separator 230A, and the positive electrode collector layer 211A are provided near the positive electrode lead 21 and the negative electrode lead 22. With this structure, the positive electrode collector layer 211A is connected to the positive electrode lead 21, and the negative electrode collector layer 221A is connected to the negative electrode lead 22.
  • the secondary battery according to this embodiment is a secondary battery having a positive electrode, a negative electrode, a separator, and an electrolyte solution, and the electrolyte solution contains an acetamide derivative represented by formula (1) and lithium bis(fluorosulfonyl)imide.
  • R1 and R2 each independently represent an alkyl group or alkoxy group having 1 to 5 carbon atoms, which may have a substituent, or a trimethylsilyl group, and R1 and R2 may be bonded to each other to form a condensed ring.
  • the molar ratio of the acetamide derivative to lithium bis(fluorosulfonyl)imide is 2 or more and 4 or less.
  • the molar ratio 2 or more corrosion of the current collector and the like caused by lithium bis(fluorosulfonyl)imide can be effectively suppressed.
  • the molar ratio 4 or less the viscosity of the electrolyte is reduced, thereby improving the discharge rate characteristics.
  • the electrolyte further contains at least one of an unsaturated cyclic carbonate and a halogenated cyclic carbonate. This creates a coating with lithium ion conductivity at the interface between the electrolyte and the positive and negative electrodes, thereby further improving the discharge rate characteristics.
  • the electrolyte further contains a hydrofluoroether. This reduces the viscosity of the electrolyte, thereby further improving the discharge rate characteristics.
  • lithium bis(fluorosulfonyl)imide is LiFSI
  • EC ethylene carbonate
  • PC propylene carbonate
  • Chemicals A to E are as follows:
  • Example 1-1 a battery for metal corrosion evaluation test was produced by stacking an aluminum foil, a polyethylene porous film, and metallic lithium, and injecting an electrolyte.
  • a battery for battery evaluation test was produced by stacking a positive electrode, a polyethylene porous film as a separator, and a negative electrode, and injecting an electrolyte.
  • the battery for battery evaluation test was designed to have a design capacity of 5 mAh.
  • Example 1-1 Chemical A was used as the solvent for the electrolyte, and LiFSI was used as the electrolyte salt.
  • the electrolyte for Example 1-1 was prepared by mixing Chemical A and LiFSI in a molar ratio of 3:1.
  • the positive electrode of the battery for the battery evaluation test was prepared by the following method. First, 91% by mass of lithium nickel oxide (LiNiO 2 ) as a positive electrode active material, 3% by mass of polyvinylidene fluoride as a binder, and 6% by mass of acetylene black as a conductive assistant were mixed together to prepare a positive electrode mixture. Then, the positive electrode mixture was put into N-methyl-2-pyrrolidone, an organic solvent, as a solvent, and stirred to prepare a paste-like positive electrode mixture slurry. Then, using a coating device, the positive electrode mixture slurry was applied to both sides of a strip-shaped aluminum foil having a thickness of 12 ⁇ m, which is a positive electrode current collector. Finally, the positive electrode mixture slurry was dried to form a positive electrode active material layer. Then, the positive electrode active material layer was compression-molded using a roll press machine to prepare a positive electrode.
  • LiNiO 2 lithium nickel oxide
  • the negative electrode of the battery for the battery evaluation test was prepared by the following method. First, 93% by mass of graphite was mixed as the negative electrode active material with 7% by mass of polyvinylidene fluoride as the binder to prepare a negative electrode mixture. Next, the negative electrode mixture was added to the organic solvent N-methyl-2-pyrrolidone as the solvent and stirred to prepare a paste-like negative electrode mixture slurry. Next, the negative electrode mixture slurry was applied to both sides of a strip of copper foil with a thickness of 15 ⁇ m as a negative electrode current collector using a coating device. The negative electrode mixture slurry was then dried to form a negative electrode active material layer. Finally, the negative electrode active material layer was compression molded using a roll press machine to prepare a negative electrode.
  • ⁇ Metal corrosion evaluation test> The prepared metal corrosion evaluation test battery was used as the working electrode, and the voltage was increased from the open circuit potential to 4.2 V at a rate of 1 mV per second, and after reaching 4.2 V, constant potential electrolysis was performed for 5 hours at 4.2 V to evaluate the occurrence of corrosion of the aluminum foil. Specifically, it was determined that corrosion of the aluminum foil had occurred when discoloration of the aluminum foil or leakage of the electrolyte occurred.
  • the initial charge/discharge test was conducted on three battery evaluation test batteries.
  • the battery evaluation test battery if the capacity measured in the initial charge/discharge was 50% or more of the theoretical capacity calculated from the mass of the active material, the battery evaluation test battery was determined to be capable of charging/discharging, and if the capacity measured in the initial charge/discharge was less than 50% of the theoretical capacity calculated from the mass of the active material, the battery evaluation test battery was determined to be incapable of charging/discharging.
  • Example 1-2 a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, except that Chemical B was used instead of Chemical A as the solvent for the electrolyte solution, and a battery evaluation test battery was prepared and an initial charge/discharge test was performed.
  • Example 1-3 In Example 1-3, except that Chemical C was used instead of Chemical A as the solvent for the electrolyte, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, and a battery evaluation test battery was prepared and an initial charge/discharge test was performed.
  • Example 1-4 a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, except that Chemical D was used instead of Chemical A as the solvent for the electrolyte solution, and a battery evaluation test battery was prepared and an initial charge/discharge test was performed.
  • Example 1-5 In Example 1-5, except that Chemical E was used instead of Chemical A as the solvent for the electrolyte, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, and a battery evaluation test battery was prepared and an initial charge/discharge test was performed.
  • Comparative Example 1-1 a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, except that ECPC was used instead of Chemical A as the solvent for the electrolyte. A battery for battery evaluation test was prepared and an initial charge/discharge test was performed.
  • Examples 1-1 to 1-5 an electrolyte solution containing one of Chemicals A to E was used, which suppressed corrosion of the aluminum foil by LiFSI, and all three batteries that underwent the battery evaluation test were able to be charged and discharged. As a result, the secondary batteries according to Examples 1-1 to 1-5 were able to be stably charged and discharged.
  • Comparative Example 1-1 an electrolyte containing ECPC was used, which suppressed corrosion of the aluminum foil by LiFSI, but all three batteries in the battery evaluation test were unable to be charged or discharged. This is thought to be because in Comparative Example 1-1, the electrolyte was highly viscous, which prevented the electrolyte from sufficiently impregnating the separator, etc., or because the ionic conductivity of the electrolyte was reduced.
  • Example 2-1 In Example 2-1, except that Compound A and LiFSI were mixed in a molar ratio of 2:1, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 1-1, and a battery evaluation test battery was prepared and an initial charge/discharge test was performed.
  • Example 2-1 in addition to the initial charge/discharge test performed in Example 1-1, a discharge rate characteristic evaluation test was performed.
  • the discharge rate characteristic evaluation test the battery for battery evaluation test, which was determined to be chargeable/dischargeable in the initial charge/discharge test, was subjected to second to sixth charge/discharge cycles as described below to evaluate the discharge rate characteristic.
  • the battery was charged at a constant charge rate under the following conditions: CCCV charging at a constant charge rate, charging at the charge control voltage after the charge control voltage was reached, charging was terminated when the current value decreased to the charge cutoff, CC discharging at a constant discharge rate, and discharging was terminated when the voltage reached the discharge end voltage.
  • the discharge capacity was measured in the second charge/discharge and was taken as the 0.2C discharge capacity.
  • the third to sixth charge/discharge cycles were performed under the same conditions as the second charge/discharge test, except that the charge rates were 0.5C, 1.0C, 2.0C, and 5.0C, respectively.
  • the discharge capacity was measured after the sixth charge/discharge cycle, and this was taken as the 5C discharge capacity.
  • the 5C discharge capacity retention rate was calculated based on the measured 0.2C discharge capacity and 5C discharge capacity.
  • the 5C discharge capacity retention rate is the ratio of the 5C discharge capacity to the 0.2 discharge capacity. In other words, if the 5C discharge capacity retention rate is high, the discharge capacity can be increased even at a high discharge rate, so it can be said that the discharge rate characteristics are improved.
  • Example 2-2 a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-1, except that Compound A and LiFSI were mixed in a molar ratio of 3:1, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed. That is, the electrolyte solution according to Example 2-2 was the same as that of Example 1-1.
  • Example 2-3 In Example 2-3, except that Compound A and LiFSI were mixed in a molar ratio of 4:1, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-1, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Example 2-4 In Example 2-4, except that Compound A and LiFSI were mixed in a molar ratio of 5:1, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-1, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Comparative Example 2-1 ECPC was used instead of Chemical A as the solvent for the electrolyte, and the molar ratio of ECPC to LiFSI was 2:1.
  • a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Comparative Example 2-2 ECPC was used instead of Chemical A as the solvent for the electrolyte, and the molar ratio of ECPC to LiFSI was 3:1, but in the same manner as in Example 2-1, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed. That is, the electrolyte according to Comparative Example 2-2 was the same as that of Comparative Example 1-1.
  • Comparative Example 2-3 ECPC was used instead of Chemical A as the solvent for the electrolyte, and the molar ratio of ECPC to LiFSI was 4:1.
  • a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Comparative Example 2-4 ECPC was used instead of Chemical A as the solvent for the electrolyte, and the molar ratio of ECPC to LiFSI was 5:1.
  • a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Examples 2-1 to 2-4 an electrolyte solution containing Chemical A was used, which suppressed corrosion of the aluminum foil by LiFSI, and all three batteries that underwent the battery evaluation test were able to be charged and discharged. As a result, the secondary batteries according to Examples 2-1 to 2-4 were able to be stably charged and discharged.
  • Comparative Examples 2-1 and 2-2 since ECPC was included, corrosion of the aluminum foil by LiFSI was suppressed, but all three batteries that underwent battery evaluation tests were unable to be charged or discharged. This is thought to be because in Comparative Examples 2-1 and 2-2, the electrolyte became highly viscous, so that the electrolyte did not sufficiently impregnate the separator, etc., or the ionic conductivity of the electrolyte decreased.
  • Comparative Example 2-3 since ECPC was included, corrosion of the aluminum foil by LiFSI was suppressed, but of the three batteries that were subjected to the battery evaluation test, two were unable to be charged or discharged. As a result, the secondary battery of Comparative Example 2-3 was unable to be stably charged or discharged. This is thought to be because in Comparative Example 2-3, the viscosity of the electrolyte was not sufficiently reduced, making it difficult for the electrolyte to impregnate the separator, etc., or because the ionic conductivity of the electrolyte was reduced.
  • Comparative Example 2-4 the concentration of ECPC relative to LiFSI was low, so corrosion of the aluminum foil by LiFSI could not be suppressed, and all three batteries that underwent the battery evaluation test were unable to be charged or discharged.
  • Example 2-3 As shown in Table 2, in Examples 2-1 to 2-3, the molar ratio of Chemical A to LiFSI was 2 or more and 4 or less, and therefore the 5C discharge capacity retention rate was improved compared to Example 2-4, in which the molar ratio was greater than 4. In Example 2-3, an electrolyte solution containing Chemical A was used, and therefore the 5C discharge capacity retention rate was improved compared to Comparative Example 2-3, in which the molar concentration of LiFSI in the electrolyte was the same.
  • Example 3-1 is an example similar to Example 2-2. That is, in Example 3-1, no additive was mixed into the electrolyte solution according to Example 2-2, and a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-2, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Example 3-2 In Example 3-2, except that 1% by mass of vinylene carbonate (VC) was mixed as an additive into the electrolyte solution of Example 2-2, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-2, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • VC vinylene carbonate
  • Example 3-3 In Example 3-3, except that 1% by mass of fluoroethylene carbonate (FEC) was mixed as an additive into the electrolyte solution of Example 2-2, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-2, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • FEC fluoroethylene carbonate
  • Example 3-4 In Example 3-4, except that 1% by mass of 4-methylene-1,3-dioxolan-2-one (MDO) was mixed as an additive into the electrolyte solution according to Example 2-2, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed in the same manner as in Example 2-2.
  • MDO 4-methylene-1,3-dioxolan-2-one
  • Example 3-4 As shown in Table 3, in Examples 3-2 to 3-4, an electrolyte in which VC, FEC or MDO was added to the electrolyte in Example 2-2 was used, and therefore the 5C discharge capacity retention rate was improved compared to Example 3-1, in which an electrolyte similar to that in Example 2-2 was used. This is thought to be because the addition of an unsaturated cyclic carbonate or halogenated cyclic carbonate to the electrolyte formed a coating with high ion conductivity at the interface between the electrolyte and the positive and negative electrodes, reducing the interface resistance.
  • Example 4-1 is an example similar to Example 2-2. That is, in Example 4-1, no additive was mixed into the electrolyte solution according to Example 2-2, and similarly to Example 2-2, a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed, and a battery evaluation test battery was prepared and an initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • Example 4-2 a metal corrosion evaluation test battery was prepared and a metal corrosion evaluation test was performed in the same manner as in Example 2-2, except that 10 mass% of 1,1,2,2-tetrafluoroethyl 2,2,3,3-tetrafluoropropyl ether (TTE) was mixed as an additive into the electrolyte solution of Example 2-2. An initial charge/discharge test and a discharge rate characteristic evaluation test were performed.
  • TTE 1,1,2,2-tetrafluoroethyl 2,2,3,3-tetrafluoropropyl ether
  • Example 4-1 an electrolyte solution obtained by adding TTE to the electrolyte solution of Example 2-2 was used, and therefore the 5C discharge capacity retention rate was improved compared to Example 4-1, which used an electrolyte solution similar to that of Example 2-2. This is believed to be because the addition of hydrofluoroether to the electrolyte reduced the viscosity of the electrolyte solution and improved the ionic conductivity.
  • the present invention may take the following forms. ⁇ 1> A secondary battery having a positive electrode, a negative electrode, a separator, and an electrolyte, The secondary battery, wherein the electrolyte solution contains an acetamide derivative represented by formula (1) and lithium bis(fluorosulfonyl)imide.
  • R1 and R2 each independently represent an alkyl group or alkoxy group having 1 to 5 carbon atoms, which may have a substituent, or a trimethylsilyl group, and R1 and R2 may be bonded to each other to form a condensed ring.
  • a molar ratio of the acetamide derivative to the lithium bis(fluorosulfonyl)imide is 2 or more and 4 or less.
  • the electrolyte solution further contains at least one of an unsaturated cyclic carbonate and a halogenated cyclic carbonate.
  • the electrolyte further contains hydrofluoroether.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002533875A (ja) * 1998-12-19 2002-10-08 ゾルファイ フルーオル ウント デリヴァーテ ゲゼルシャフト ミット ベシュレンクテル ハフツング リチウム電池用電解質系、その使用、およびリチウム電池の安全性を高める方法
JP2003031260A (ja) * 2001-07-13 2003-01-31 Daikin Ind Ltd 電解液および／または電極表面被膜形成剤。
WO2010110290A1 (ja) * 2009-03-26 2010-09-30 ダイキン工業株式会社 リチウム二次電池用非水電解液
CN109638355A (zh) * 2018-12-14 2019-04-16 河南华瑞高新材料有限公司 一种锂离子电池高温电解液

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002533875A (ja) * 1998-12-19 2002-10-08 ゾルファイ フルーオル ウント デリヴァーテ ゲゼルシャフト ミット ベシュレンクテル ハフツング リチウム電池用電解質系、その使用、およびリチウム電池の安全性を高める方法
JP2003031260A (ja) * 2001-07-13 2003-01-31 Daikin Ind Ltd 電解液および／または電極表面被膜形成剤。
WO2010110290A1 (ja) * 2009-03-26 2010-09-30 ダイキン工業株式会社 リチウム二次電池用非水電解液
CN109638355A (zh) * 2018-12-14 2019-04-16 河南华瑞高新材料有限公司 一种锂离子电池高温电解液

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