WO2016027788A1 - 電解質組成物、二次電池、及び二次電池の使用方法 - Google Patents

電解質組成物、二次電池、及び二次電池の使用方法 Download PDF

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WO2016027788A1
WO2016027788A1 PCT/JP2015/073058 JP2015073058W WO2016027788A1 WO 2016027788 A1 WO2016027788 A1 WO 2016027788A1 JP 2015073058 W JP2015073058 W JP 2015073058W WO 2016027788 A1 WO2016027788 A1 WO 2016027788A1
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group
carbon atoms
component
ether bond
electrolyte composition
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French (fr)
Japanese (ja)
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征太郎 山口
宮田　壮
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リンテック株式会社
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Priority to CN201580045115.5A priority Critical patent/CN106575791A/zh
Priority to KR1020177006892A priority patent/KR20170044136A/ko
Priority to JP2016544204A priority patent/JPWO2016027788A1/ja
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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
    • H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
    • 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
    • H01M10/056—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
    • H01M10/056—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
    • H01M10/44—Methods for charging or discharging
    • 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 an electrolyte composition having ionic conductivity and excellent electrochemical stability, a secondary battery having excellent cycle characteristics and high capacity, and a method of using the secondary battery. About.
  • Patent Document 1 discloses a positive electrode active material for a secondary battery containing two specific types of oxides, which contributes to improving the cycle characteristics of a 5V class secondary battery and the reliability of high-temperature operation.
  • the conductive polymer or the like constituting the electrolyte may be decomposed under a high voltage, and the battery performance may be deteriorated, ruptured, or ignited. was there.
  • an electrolyte composition that has ionic conductivity and excellent electrochemical stability (in the present invention, it means that it is difficult to undergo oxidative decomposition even at a high potential).
  • the discharge capacity may gradually decrease. For this reason, in order not to reduce the discharge capacity even after repeated charge and discharge, it is necessary to lower the upper limit of the cut-off voltage at the time of charge, and it has not been possible to use as a high capacity battery.
  • Patent Documents 2 and 3 describe a proton conductor composed of a zwitterionic salt and a proton donor, and a fuel cell having a proton conducting layer composed of this proton conductor. .
  • JP2011-138787A Japanese Patent Laying-Open No. 2005-228588 (US2006 / 0263661A1)
  • WO2006 / 025482 pamphlet US2007 / 0231647, A1
  • the present invention has been made in view of the above circumstances, has an ionic conductivity and is excellent in electrochemical stability, and is excellent in cycle characteristics (the discharge capacity is reduced even after repeated charge and discharge). It is an object to provide a secondary battery having a high capacity and a method of using the secondary battery.
  • the following electrolyte compositions (1) to (6), a secondary battery (7), and a method of using the secondary battery (8) are provided.
  • (A) component (A-1) at least one polymer compound selected from the group consisting of a polyalkylene oxide, a polyalkylene carbonate, and a vinyl polymer having a repeating unit derived from an alkylene polyol (meth) acrylate, or (A-2) ) At least one organic solvent (B) component selected from the group consisting of carbonate solvents, ester solvents, lactone solvents, ether solvents, nitrile solvents, and sulfur-containing solvents: Group 1 of the periodic table or Group 2 metal salt (C) component: Formula (I)
  • X + may include one or more nitrogen atoms or phosphorus atoms, and represents a cationic group having 1 bond, Y is bonded to the nitrogen atom or phosphorus atom of X +, Represents an alkylene group having 2 to 5 carbon atoms.
  • component (A) is at least one selected from the group consisting of polyethylene oxide, ethylene carbonate, and diethyl carbonate.
  • component (B) is a lithium salt.
  • the electrolyte composition according to (1), wherein the cationic group represented by X + in the component (C) is a group represented by any of the following formulas (II) to (VI).
  • R 1 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon number with or without an ether bond.
  • An alkyl group, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, an alkenyl group having 2 to 10 carbon atoms with or without an ether bond, or a substituted or unsubstituted aryl having 6 to 20 carbon atoms R 2 and R 3 may be bonded to each other to form a ring, and * represents a bond.
  • R 4 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon having or without an ether bond.
  • a alkenyl group having 2 to 10 carbon atoms, R 5 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond, and * represents a bond.
  • R 6 to R 10 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond. * Represents a bond
  • R 11 to R 15 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond. * Represents a bond
  • R 16 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon number with or without an ether bond.
  • An alkyl group, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, an alkenyl group having 2 to 10 carbon atoms with or without an ether bond, or a substituted or unsubstituted aryl having 6 to 20 carbon atoms Represents a group. * Represents a bond.)
  • the content ratio of the component (A) and the component (B) is 100: 0.1 to 100: 10,000 in mass ratio of [(A) component: (B) component] ( The electrolyte composition as described in 1).
  • the ratio of the content of the component (A) to the component (C) is 100: 0.01 to 100: 100 in mass ratio of (component (A): component (C)) (1)
  • the method for using the secondary battery according to (7), wherein the upper limit of the cut-off voltage during charging is 4.4 to 5.5V.
  • an electrolyte composition having ionic conductivity and excellent electrochemical stability, a secondary battery having excellent cycle characteristics and a high capacity, and a method of using the secondary battery are provided. Provided.
  • FIG. It is a graph showing the result of the constant current charging / discharging test 1 performed using the electrolyte composition (14) of Example 12 and the electrolyte composition (12) of Comparative Example 2, respectively.
  • Electrolyte composition contains the following (A) component, (B) component, and (C) component.
  • A) component (A-1) at least one polymer compound selected from the group consisting of a polyalkylene oxide, a polyalkylene carbonate, and a vinyl polymer having a repeating unit derived from an alkylene polyol (meth) acrylate, or (A-2) )
  • At least one organic solvent (B) selected from the group consisting of carbonate solvents, ester solvents, ether solvents, lactone solvents, nitrile solvents, and sulfur-containing solvents: Group 1 of the periodic table or Group 2 metal salt
  • C) component zwitterionic compound represented by formula (I)
  • the component (A) constituting the electrolyte composition of the present invention is selected from the group consisting of (A-1) a polyalkylene oxide, a polyalkylene carbonate, and a vinyl polymer having a repeating unit derived from an alkylene polyol (meth) acrylate. At least one polymer compound selected, or (A-2) at least one selected from the group consisting of carbonate solvents, ester solvents, lactone solvents, ether solvents, nitrile solvents, and sulfur-containing solvents. It is a seed organic solvent.
  • the component (A) is used as an ion conductive medium.
  • the polymer compound of component (A-1) is at least one selected from the group consisting of polyalkylene oxides, polyalkylene carbonates, and vinyl polymers having repeating units derived from alkylene polyol (meth) acrylates.
  • Examples of the polyalkylene oxide of the component (A-1) include compounds represented by the following formula (VII).
  • R a represents an alkylene group having 2 to 10 carbon atoms.
  • R b and R c each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • P represents an arbitrary natural number.
  • p is 2 or more, a plurality of R a may be the same or different from each other, and when the compound represented by the formula (VII) is a copolymer, it is a block copolymer. It may be a random copolymer.
  • the alkylene group for R a has 2 to 10 carbon atoms, preferably 2 to 5 carbon atoms, more preferably 2 or 3.
  • Examples of the alkylene group for Ra include an ethylene group, a triethylene group, a propylene group, and a tetraethylene group.
  • Examples of the alkyl group for R b and R c include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a t-butyl group.
  • Examples of the compound represented by the formula (VII) include polyethylene oxide, polypropylene oxide, ethylene oxide-propylene oxide copolymer, and the like, polyalkylene oxides having both hydrogen terminals at the molecular ends; polyethylene oxide monomethyl ether, polypropylene oxide monomethyl ether, ethylene oxide -Polyalkylene oxide monoalkyl ethers such as monomethyl ether of propylene oxide copolymer; Polyalkylene oxide dialkyl ethers such as polyethylene oxide dimethyl ether, polypropylene oxide dimethyl ether, and dimethyl ether of ethylene oxide-propylene oxide copolymer; It is done.
  • EO represents an oxyethylene group (—CH 2 CH 2 —O—)
  • PO represents an oxypropylene group [—CH (CH 3 ) —CH 2 —O—]
  • q and r are q Integers satisfying ⁇ 0, r ⁇ 0, and q + r ⁇ 2.
  • — (EO) q — and — (PO) r — indicate the presence or absence and the amount of each repeating unit, and do not represent the order. Therefore, the compound represented by the formula (VIII) includes a homopolymer consisting only of EO repeating units, a homopolymer consisting only of PO repeating units, and a random copolymer consisting of EO repeating units and PO repeating units. And a block copolymer composed of a repeating unit of EO and a repeating unit of PO.
  • Polyalkylene oxide can be synthesized using a known production method such as polymerization reaction of alkylene oxide using an organoaluminum catalyst. Commercially available products can be used as the component (A-1) as they are.
  • Examples of the polyalkylene carbonate as the component (A-1) include compounds represented by the following formula (IX).
  • R d represents an alkylene group having 2 to 10 carbon atoms.
  • R e and R f each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • S represents an arbitrary natural number.
  • s is 2 or more, a plurality of R d may be the same or different from each other, and when 2 or more R d is included, the compound represented by the formula (IX) It may be a polymer or a random copolymer.
  • the carbon number of the alkylene group for R d is 2 to 10, preferably 2 to 5, and more preferably 2 or 3.
  • Examples of the alkylene group for Rd include an ethylene group, a triethylene group, a propylene group, and a tetraethylene group.
  • Examples of the alkyl group for R e and R f include a methyl group, an ethyl group, and an n-propyl group.
  • Examples of the compound represented by the formula (IX) include polyethylene carbonate and polypropylene carbonate.
  • Polyalkylene carbonate can be synthesized using a known production method such as a method of reacting carbon dioxide and epoxide in the presence of a zinc-based catalyst.
  • a known production method such as a method of reacting carbon dioxide and epoxide in the presence of a zinc-based catalyst.
  • Commercially available products can be used as the component (A-1) as they are.
  • the vinyl polymer having a repeating unit derived from the alkylene polyol (meth) acrylate as the component (A-1) is represented by the following formula (X)
  • R g represents a hydrogen atom or a methyl group
  • R h represents an alkylene group having 2 to 10 carbon atoms
  • R i represents an alkyl group having 1 to 10 carbon atoms
  • t represents an arbitrary integer
  • the plurality of R h may be the same as or different from each other, and when two or more R h are included, the chain represented by (OR h ) t may be a block copolymer chain. It may be a random copolymer chain.) (Hereinafter sometimes referred to as monomer ( ⁇ )). ] And a polymer obtained by polymerizing].
  • the alkylene group of R h has 2 to 10, preferably 2 to 5, more preferably 2 or 3, carbon atoms.
  • Examples of the alkylene group for R h include an ethylene group, a triethylene group, a propylene group, and a tetraethylene group.
  • Examples of the alkyl group for Ri include a methyl group, an ethyl group, and an n-propyl group.
  • Monomers ( ⁇ ) include 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, 2-ethoxypropyl (meth) acrylate, diethylene glycol monomethyl ether (meta ) Acrylate, diethylene glycol monoethyl ether (meth) acrylate, methoxypolyethylene glycol (meth) acrylate (the number of repeating units is 2 to 100), ethoxy polyethylene glycol (meth) acrylate (the number of repeating units is 2 to 100), and the like.
  • a monomer ((alpha)) can be used individually by 1 type or in combination of 2 or more types.
  • the vinyl polymer as the component (A-1) is a monomer other than the monomer ( ⁇ ) that can be copolymerized with the monomer ( ⁇ ) [hereinafter sometimes referred to as monomer ( ⁇ ). ] And a monomer ( ⁇ ).
  • Examples of the monomer ( ⁇ ) include (meth) acrylate monomers other than the monomer ( ⁇ ), ⁇ -olefin monomers, and other vinyl monomers.
  • Examples of the (meth) acrylic acid ester monomers other than the monomer ( ⁇ ) include alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, and n-propyl (meth) acrylate.
  • Examples of the ⁇ -olefin monomer include ethylene, propylene, and isobutylene.
  • Examples of other vinyl monomers include styrene, ⁇ -methylstyrene, vinyl toluene, vinyl formate, vinyl acetate, acrylonitrile, acrylamide and the like.
  • the vinyl polymer used as the component (A-1) preferably has a content of repeating units derived from the monomer ( ⁇ ) of 20 to 100% by mass, preferably 25 to 50% by mass, based on all repeating units. Those are more preferred.
  • the vinyl polymer used as the component (A-1) can be produced by a known polymerization method such as a method of polymerizing a monomer using a radical polymerization initiator in the presence or absence of a solvent. Can do. Commercially available products can be used as the component (A-1) as they are.
  • the mass average molecular weight of the component (A-1) is not particularly limited, but is usually 500 to 6,000,000, preferably 600 to 1,500,000, more preferably 700 to 50,000, particularly preferably 800 to 10,000.
  • the weight average molecular weight of the component (A-1) is a standard polystyrene equivalent value measured by gel permeation chromatography (GPC) method using N, N-dimethylformamide, tetrahydrofuran, chloroform or the like as a solvent.
  • the organic solvent of component (A-2) is at least one selected from the group consisting of carbonate solvents, ester solvents, lactone solvents, ether solvents, nitrile solvents, and sulfur-containing solvents.
  • Component carbonate solvents include dimethyl carbonate, diethyl carbonate, dipropyl carbonate, methyl propyl carbonate, ethyl propyl carbonate, methyl ethyl carbonate, ethyl methyl carbonate, ethylene carbonate, propylene carbonate, butylene carbonate, vinylene. And carbonate.
  • Examples of the ester solvent include n-methyl acetate, n-ethyl acetate, n-propyl acetate and the like.
  • Examples of the lactone solvent of the component (A-2) include ⁇ -butyrolactone, valerolactone, mevalonolactone, caprolactone and the like.
  • ether solvents include cyclic ethers such as tetrahydrofuran and 2-methyltetrahydrofuran; chain ethers such as dibutyl ether, 1,2-dimethoxyethane, 1,2-dibutoxyethane, and 1,4-dioxane; It is done.
  • nitrile solvents include acetonitrile and propionitrile.
  • sulfur-containing solvent include sulfolane and dimethyl sulfoxide.
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • the component (A) at least one selected from the group consisting of polyethylene oxide, ethylene carbonate, and diethyl carbonate is preferable because an electrolyte composition that is more excellent in electrochemical stability can be obtained.
  • the oxidation potential of the component (A) is preferably 3.5 V or more, more preferably 4.0 to 6.5 V.
  • the oxidation potential of the component (A) is within the above range, an electrolyte composition that is more excellent in electrochemical stability can be obtained.
  • the oxidation potential means a potential at which the current increases beyond the electrochemically stable range when the potential is high.
  • the component (B) constituting the electrolyte composition of the present invention is a metal salt of Group 1 or Group 2 of the Periodic Table. In the electrolyte composition of the present invention, the component (B) is used as an ion source.
  • metal ions constituting the metal salt examples include alkali metal ions such as lithium ions, sodium ions and potassium ions; magnesium ions; alkaline earth metal ions such as calcium ions and strontium ions.
  • the anion constituting the metal salt (CH 2 FSO 2) 2 N - [bis (trifluoromethanesulfonyl) amine anion], (CF 3 SO 2) 2 N - [bis (trifluoromethanesulfonyl) amine anion ], (C 2 F 5 SO 2 ) 2 N - [bis (pentafluoroethanesulfonyl) amine anion], (FSO 2) 2 N - [bis (fluorosulfonyl) amine anion], (CF 3 SO 2) 3 C - [Tris (trifluoromethanesulfonyl) methide ion], trifluoromethanesulfonate ion, hexafluorophosphate ion, tetrafluoroborate ion, tetracyanoborate ion, perchlorate ion, hexafluoroarsenate ion and the like.
  • the metal salt is preferably a lithium salt, sodium salt, potassium salt, magnesium salt or calcium salt, and more preferably a lithium salt.
  • the lithium salt include lithium bis (fluoromethanesulfonyl) amide (LiN (SO 2 CH 2 F) 2 ), lithium bis (trifluoromethanesulfonyl) amide (LiN (SO 2 CF 3 ) 2 ), lithium bis (pentafluoroethane).
  • the content ratio of the component (A) and the component (B) is a mass ratio of [(A) component: (B) component], preferably 100: 0.1 to 100 : 10,000, more preferably 100: 1 to 100: 1000.
  • the content ratio of the component (A) and the component (B) is within the above range, an electrolyte composition having sufficient ionic conductivity can be easily obtained.
  • the component (C) constituting the electrolyte composition of the present invention is a zwitterionic compound represented by the following formula (I).
  • the electrolyte composition of this invention is excellent in electrochemical stability.
  • the secondary battery using the electrolyte composition containing the component (C) has excellent cycle characteristics even when the upper limit of the cutoff voltage during charging is increased to 4.4 V or higher.
  • X + represents a cationic group containing one or more nitrogen atoms or phosphorus atoms and having one bond
  • Y is bonded to the nitrogen atom or phosphorus atom of X + Represents an alkylene group having 2 to 5 carbon atoms.
  • the number of carbon atoms of the cationic group represented by X + is preferably 1 to 40, more preferably 3 to 30, further preferably 6 to 20, and particularly preferably 9 to 15.
  • Examples of the cationic group represented by X + include groups represented by any of the following formulas (II) to (VI).
  • R 1 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon number with or without an ether bond.
  • An alkyl group, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, an alkenyl group having 2 to 10 carbon atoms with or without an ether bond, or a substituted or unsubstituted aryl having 6 to 20 carbon atoms R 2 and R 3 may be bonded to each other to form a ring, and * represents a bond.
  • R 4 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon having or without an ether bond.
  • a alkenyl group having 2 to 10 carbon atoms, R 5 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond, and * represents a bond.
  • R 6 to R 10 represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond. * Represents a bond.
  • R 11 to R 15 represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms with or without an ether bond. * Represents a bond.
  • R 16 is an alkyl group having 1 to 10 carbon atoms with or without an ether bond, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, or a carbon number with or without an ether bond.
  • An alkyl group, a cyanoalkyl group having 2 to 11 carbon atoms with or without an ether bond, an alkenyl group having 2 to 10 carbon atoms with or without an ether bond, or a substituted or unsubstituted aryl having 6 to 20 carbon atoms Represents a group. * Represents a bond.
  • the number of carbon atoms of the alkyl group of 1 to 10 carbon atoms having or not having an ether bond as R 1 to R 18 is preferably 1 to 8, and preferably 1 to 5 More preferred.
  • the alkyl group having no ether bond include a methyl group, an ethyl group, an n-propyl group, and an n-butyl group.
  • the alkyl group having an ether bond include groups represented by the following formulas.
  • R 19 represents an alkyl group having 1 to 8 carbon atoms
  • Z 1 represents an alkylene group having 2 to 9 carbon atoms
  • the total number of carbon atoms of R 19 and Z 1 is 3 to 10
  • R 20 represents an alkyl group having 1 to 6 carbon atoms
  • Z 2 represents an alkylene group having 2 to 7 carbon atoms
  • Z 3 represents an alkylene group having 2 to 7 carbon atoms
  • R 20 (The total number of carbon atoms of Z 2 and Z 3 is 5 to 10. * represents a bond.)
  • the number of carbon atoms of the cyanoalkyl group having 2 to 11 carbon atoms, with or without an ether bond, of R 1 to R 4 and R 16 to R 18 is preferably 2 to 9, and more preferably 2 to 6.
  • Examples of the cyanoalkyl group having no ether bond include a cyanomethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, and a 4-cyanobutyl group.
  • Examples of the cyanoalkyl group having an ether bond include groups represented by the following formulas.
  • R 21 represents a cyanoalkyl group having 2 to 9 carbon atoms
  • Z 4 represents an alkylene group having 2 to 9 carbon atoms
  • the total number of carbon atoms of R 21 and Z 4 is 4 to 11
  • R 22 represents a cyanoalkyl group having 2 to 7 carbon atoms
  • Z 5 represents an alkylene group having 2 to 7 carbon atoms
  • Z 6 represents an alkylene group having 2 to 7 carbon atoms
  • R 22 , Z 5 and Z 6 have a total carbon number of 6 to 11. * represents a bond.
  • the number of carbon atoms of the alkenyl group having 2 to 10 carbon atoms with or without an ether bond of R 1 to R 4 and R 16 to R 18 is preferably 2 to 9, and more preferably 2 to 6.
  • Examples of the alkenyl group having no ether bond include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 1-pentenyl group.
  • Examples of the alkenyl group having an ether bond include groups represented by the following formulas.
  • R 23 represents an alkenyl group having 2 to 8 carbon atoms
  • Z 7 represents an alkylene group having 2 to 8 carbon atoms
  • the total number of carbon atoms of R 23 and Z 7 is 4 to 10
  • R 24 represents an alkenyl group having 2 to 6 carbon atoms
  • Z 8 represents an alkylene group having 2 to 6 carbon atoms
  • Z 9 represents an alkylene group having 2 to 6 carbon atoms
  • R 24 (The total number of carbon atoms of Z 8 and Z 9 is 6 to 10. * represents a bond.)
  • the aryl group of the substituted or unsubstituted aryl group having 6 to 20 carbon atoms of R 1 to R 3 and R 16 to R 18 preferably has 6 to 10 carbon atoms.
  • the unsubstituted aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • the substituent of the substituted aryl group include an alkyl group having 1 to 6 carbon atoms such as a methyl group and an ethyl group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group;
  • Examples of the ring formed by combining R 2 and R 3 include a nitrogen-containing 5-membered ring such as a pyrrolidine ring; a nitrogen-containing 6-membered ring such as a piperazine ring, a piperidine ring, and a morpholine ring;
  • Y represents an alkylene group having 2 to 5 carbon atoms which is bonded to a nitrogen atom or phosphorus atom of X + .
  • alkylene group for Y linear alkylene groups such as ethylene group, trimethylene group, tetramethylene group and pentamethylene group; branched chain such as propane-1,2-diyl group and butane-1,3-diyl group An alkylene group is mentioned.
  • the method for producing the zwitterionic compound used as the component (C) is not particularly limited.
  • the zwitterionic compound (3) in which X + is a group represented by the formula (II) reacts the corresponding amine compound (1) with the sultone compound (2). Can be obtained.
  • Examples of the amine compound (1) include trimethylamine, triethylamine, tri (n-butylamine) and the like. These amine compounds can be produced and obtained using the synthesis methods described in the Examples. Moreover, a commercial item can also be used as an amine compound.
  • sultone compound (2) examples include 1,2-ethane sultone, 1,3-propane sultone, 1,4-butane sultone, 2,4-butane sultone, and 1,5-pentane sultone. These are known compounds and can be produced and obtained by known methods. Moreover, a commercial item can also be used as a sultone compound.
  • the amount of the sultone compound (2) used is preferably 0.8 to 1.2 equivalents, more preferably 0, relative to the amine compound (1). .9 to 1.1 equivalents.
  • the reaction of the amine compound (1) and the sultone compound (2) may be performed without a solvent or in the presence of an inert solvent.
  • Inert solvents used include ether solvents such as tetrahydrofuran and diglyme; nitrile solvents such as acetonitrile and propionitrile; ketone solvents such as acetone and methyl ethyl ketone; aromatic hydrocarbon solvents such as toluene and xylene; chloroform and the like And halogenated hydrocarbon solvents.
  • the amount used is not particularly limited, but it is usually preferably 100 parts by mass or less with respect to 1 part by mass of the amine compound (1).
  • the reaction temperature is not particularly limited, but is usually in the range of 0 to 200 ° C, preferably 10 to 100 ° C, more preferably 20 to 60 ° C. Further, the reaction may be carried out under normal pressure conditions, or the reaction may be carried out under pressurized conditions.
  • the reaction time is not particularly limited, but is usually 12 to 332 hours, preferably 24 to 168 hours.
  • the reaction is preferably performed in an inert gas atmosphere from the viewpoint of preventing yield reduction due to oxidation by oxygen and hydrolysis of the sultone compound (2) by moisture in the air. The progress of the reaction can be confirmed by ordinary analytical means such as gas chromatography, high performance liquid chromatography, thin layer chromatography, NMR, IR and the like.
  • the obtained zwitterionic compound can be purified and isolated by a known purification method such as solvent washing, recrystallization, column chromatography and the like.
  • R 4 to R 18 represent the same meaning as described above.
  • the compounds represented by the formulas (XI) to (XIV) can be produced and obtained using the synthesis methods described in the examples. Commercial products can also be used.
  • the content ratio of the component (A) and the component (C) is a mass ratio of [(A) component: (B) component], preferably 100: 0.01 to 100. : 100, more preferably 100: 0.1 to 100: 50.
  • the content ratio of the component (A) and the component (C) is within the above range, an electrolyte composition having sufficient ionic conductivity and excellent electrochemical stability can be easily obtained.
  • the secondary battery containing the electrolyte composition becomes more excellent in cycle characteristics.
  • the electrolyte composition of the present invention is excellent in electrochemical stability.
  • the electrolyte composition of the present invention is excellent in electrochemical stability because, for example, when linear sweep voltammetry is performed under the conditions described in the examples, the oxidation potential of the electrolyte composition of the present invention is (A ) And a higher value than the oxidation potential of the mixture of the component (B).
  • the oxidation potential of the electrolyte composition of the present invention is preferably 4.3 V or more, more preferably 4.6 to 6.5 V.
  • the electrolyte composition of the present invention has ionic conductivity and is excellent in electrochemical stability. Therefore, the electrolyte composition of the present invention is suitably used as an electrolyte material for a secondary battery or the like using a positive electrode active material having a high operating potential.
  • the secondary battery of the present invention has a positive electrode, a negative electrode, and the electrolyte composition of the present invention.
  • the positive electrode usually includes a positive electrode current collector and a positive electrode active material layer.
  • the current collector holds the active material layer and is responsible for transferring electrons to and from the active material.
  • the material constituting the positive electrode current collector is not particularly limited. For example, metal materials and conductive polymers such as aluminum, nickel, iron, stainless steel, titanium, and copper can be used.
  • the positive electrode active material layer is a layer formed on the surface of the positive electrode current collector, and contains a positive electrode active material. Examples of the positive electrode active material include LiMn 2 O 4 , LiCoO 2 , LiNiO 2 , Li (Ni—Mn—Co) O 2, and inorganic active materials such as those obtained by substituting some of these transition metals with other elements. Is mentioned.
  • the positive electrode active material layer may contain an additive in addition to the positive electrode active material.
  • additives include binders such as polyvinylidene fluoride, synthetic rubber binders, and epoxy resins; conductive assistants such as carbon black, graphite, and vapor-grown carbon fibers; electrolyte salts such as component (B) of the present invention; poly And ion conductive polymers such as ethylene oxide (PEO) -based polymers and polypropylene oxide (PPO) -based polymers.
  • the negative electrode usually includes a negative electrode current collector and a negative electrode active material layer.
  • the negative electrode may be composed of only the negative electrode active material layer (that is, the negative electrode active material layer also serves as the negative electrode current collector). Examples of the material constituting the negative electrode current collector include the same materials as those shown for the positive electrode current collector.
  • the negative electrode active material layer is a layer formed on the surface of the negative electrode current collector, and contains a negative electrode active material.
  • the negative electrode active material examples include carbon materials such as graphite, soft carbon, and hard carbon; lithium-transition metal composite oxides such as Li 4 Ti 5 O 12 ; silicon materials such as silicon simple substance, silicon oxide, and silicon alloy; lithium metal A lithium-metal alloy such as lithium-tin or a lithium-silicon alloy; a simple substance such as a tin material, an alloy, a compound; or a composite material using these materials in combination.
  • the negative electrode active material layer may contain an additive in addition to the negative electrode active material. Examples of such additives include the same as those shown as additives in the positive electrode active material layer.
  • the electrolyte composition of the present invention exists between the positive electrode and the negative electrode, and is responsible for ionic conduction.
  • the secondary battery of the present invention may have a separator between the positive electrode and the negative electrode.
  • the separator has a function of electronically insulating the positive electrode and the negative electrode to prevent a short circuit and to allow only the movement of ions.
  • Examples of the material constituting the separator include a porous body formed of an insulating plastic such as polyethylene, polypropylene, and polyimide, and inorganic fine particles such as silica gel.
  • the manufacturing method of the secondary battery of this invention is not specifically limited, It can manufacture according to a well-known method.
  • the secondary battery of the present invention contains a zwitterionic compound [component (C)], even if charging and discharging are repeated by increasing the upper limit of the cutoff voltage during charging, the discharge capacity is unlikely to decrease.
  • component (C) a zwitterionic compound
  • the secondary battery of the present invention is excellent in cycle characteristics even if the upper limit of the cutoff voltage during charging is increased, and is a secondary battery having a higher capacity.
  • Activated carbon was added to a solution obtained by dissolving the obtained crystals in methanol, and the mixture was heated to reflux for 24 hours. After the activated carbon was filtered off, methanol was distilled off from the filtrate using a rotary evaporator to obtain a zwitterionic compound (9) represented by the following formula as colorless crystals. (Yield 13.5 g, Yield 77.9%)
  • Example 1 Polyethylene oxide (manufactured by Aldrich, mass average molecular weight 1,000) 1500 mg, lithium bis (trifluoromethanesulfonyl) amide (manufactured by Kanto Chemical Co.) 1170 mg, and zwitterionic compound (1) 60 mg obtained in Production Example 1 were dehydrated acetonitrile Added to 3 ml and stirred the whole volume for 24 hours. Then, acetonitrile was depressurizingly distilled and the electrolyte composition (1) was obtained by vacuum-drying the obtained residue at 70 degreeC for 48 hours.
  • Example 2 In Example 1, instead of zwitterionic compound (1), electrolyte composition (2) was obtained in the same manner as in Example 1 except that 66 mg of zwitterionic compound (2) obtained in Production Example 2 was used. Got.
  • Example 3 In Example 1, instead of the zwitterionic compound (1), the electrolyte composition (3) was obtained in the same manner as in Example 1 except that 65 mg of the zwitterionic compound (3) obtained in Production Example 3 was used. Got.
  • Example 4 In Example 1, an electrolyte composition (4) was prepared in the same manner as in Example 1 except that 53 mg of the zwitterionic compound (4) obtained in Production Example 4 was used instead of the zwitterionic compound (1). Got.
  • Example 5 In Example 1, instead of zwitterionic compound (1), electrolyte composition (5) was used in the same manner as in Example 1 except that 70 mg of zwitterionic compound (5) obtained in Production Example 5 was used. Got.
  • Example 6 In Example 1, instead of zwitterionic compound (1), electrolyte composition (6) was obtained in the same manner as in Example 1 except that 52 mg of zwitterionic compound (6) obtained in Production Example 6 was used. Got.
  • Example 7 In Example 1, instead of zwitterionic compound (1), electrolyte composition (7) was obtained in the same manner as in Example 1 except that 58 mg of zwitterionic compound (7) obtained in Production Example 7 was used. Got.
  • Example 8 In Example 1, instead of zwitterionic compound (1), electrolyte composition (8) was obtained in the same manner as in Example 1 except that 64 mg of zwitterionic compound (8) obtained in Production Example 8 was used. Got.
  • Example 9 In Example 1, instead of zwitterionic compound (1), electrolyte composition (9) was used in the same manner as in Example 1 except that 62 mg of zwitterionic compound (9) obtained in Production Example 9 was used. Got.
  • Example 10 Organic electrolyte solution (manufactured by Kishida Chemical Co., Ltd., product name: LBG-96553, solvent: mixed solvent in which ethylene carbonate and diethyl carbonate are 1: 1 in volume ratio, electrolyte: LiPF 6 , molar concentration of electrolyte: 1 mol / l)
  • the zwitterionic compound (9) obtained in Production Example 9 was added so as to have a concentration of 2.25% by mass and stirred for 24 hours to obtain an electrolyte composition (10).
  • Example 1 an electrolyte composition (11) was obtained in the same manner as in Example 1 except that the zwitterionic compound (1) was not added.
  • LSV linear sweep voltammetry
  • Measuring device manufactured by ALS, product name 606C Measurement temperature: 40 ° C Scanning potential range: 0-6V
  • Working electrode Platinum plate Counter electrode: Lithium foil scanning speed: 1 mV / s
  • the electrolyte compositions (1) to (10) of Examples 1 to 10 have a smaller current flow even at a higher potential than the electrolyte compositions (11) and (12) of Comparative Examples 1 and 2, and Excellent in mechanical stability.
  • the electrolyte compositions (1) and (10) are characterized by a low potential at which a reduction current flows even on the low potential side and a wide electrochemically stable potential range, that is, a potential window.
  • Example 11 In Example 1, instead of zwitterionic compound (1), electrolyte composition (13) was obtained in the same manner as in Example 1 except that 128 mg of zwitterionic compound (9) obtained in Production Example 9 was used. Got.
  • Example 12 In Example 10, instead of the zwitterionic compound (9), the zwitterionic compound (2) obtained in Production Example 2 was added so as to have a concentration of 5% by mass, and the mixture was stirred for 24 hours. A composition (14) was obtained.
  • a constant current charge / discharge test was performed by the following method.
  • Constant current charge / discharge test 1 31.9 g of lithium cobaltate (Kusaka Rare Metal Laboratory Co., Ltd.) and 2.25 g of acetylene black (Denka Black, Denki Kagaku Co., Ltd.) were mixed while grinding on a mortar, and then PVDF (polyvinylidene fluoride) solution (Kureha) -Battery Materials Japan, KF Polymer # 1120, solid content 12%) 27.5 g, N-methylpyrrolidone (Wako Pure Chemical Industries, Ltd.) 54 g was added and mixed.
  • PVDF polyvinylidene fluoride
  • the obtained mixture was stirred for 30 minutes using a homogenizer to obtain a positive electrode active material dispersion.
  • the obtained positive electrode active material dispersion was applied onto an aluminum foil using an applicator, and the obtained coating film was dried at 80 ° C. for 1 hour. This was pressed at 70 ° C. and 0.02 MPa / cm 2 for 1 hour to prepare an electrode sheet.
  • Constant current charge / discharge test 3 The test was performed in the same manner as the constant current charge / discharge test 1 except that an electrode sheet obtained using Li (Ni—Mn—Co) O 2 instead of lithium cobalt oxide was used as the positive electrode.
  • FIGS. 13 shows the results of the constant current charge / discharge test 1
  • FIGS. 14 and 15 show the results of the constant current charge / discharge test 2
  • FIG. 16 shows the results of the constant current charge / discharge test 3.
  • the horizontal axis represents the number of times of charge / discharge
  • the vertical axis represents the discharge capacity.

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WO2020017318A1 (ja) * 2018-07-17 2020-01-23 宇部興産株式会社 非水電解液及びそれを用いた蓄電デバイス
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JP2018181511A (ja) * 2017-04-07 2018-11-15 トヨタ自動車株式会社 リチウムイオン二次電池
US20190131656A1 (en) * 2017-10-31 2019-05-02 Toyota Jidosha Kabushiki Kaisha Method of producing lithium-ion secondary battery, lithium-ion secondary battery, and method of using zwitterionic compound
JP2019083154A (ja) * 2017-10-31 2019-05-30 トヨタ自動車株式会社 リチウムイオン二次電池の製造方法、リチウムイオン二次電池、およびリチウムイオン二次電池用容量回復剤
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JPWO2020017318A1 (ja) * 2018-07-17 2021-08-12 Ｍｕアイオニックソリューションズ株式会社 非水電解液及びそれを用いた蓄電デバイス
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WO2020017318A1 (ja) * 2018-07-17 2020-01-23 宇部興産株式会社 非水電解液及びそれを用いた蓄電デバイス
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