WO2019181704A1 - Agent de suppression d'emballement thermique - Google Patents

Agent de suppression d'emballement thermique Download PDF

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WO2019181704A1
WO2019181704A1 PCT/JP2019/010401 JP2019010401W WO2019181704A1 WO 2019181704 A1 WO2019181704 A1 WO 2019181704A1 JP 2019010401 W JP2019010401 W JP 2019010401W WO 2019181704 A1 WO2019181704 A1 WO 2019181704A1
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trimethylsilyl
thermal runaway
aqueous electrolyte
positive electrode
group
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Japanese (ja)
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健二 撹上
洋平 青山
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Adeka Corp
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Adeka Corp
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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
    • H01M10/052—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
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/50—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese
    • H01M4/505—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/52—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron
    • H01M4/525—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • 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
    • H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
    • 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
    • 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 inhibitor of thermal runaway due to an internal short circuit of a nonaqueous electrolyte secondary battery, and a method of suppressing thermal runaway due to an internal short circuit using the inhibitor.
  • Non-aqueous electrolyte secondary batteries such as lithium ion secondary batteries are small and light, have high energy density, high capacity, and can be repeatedly charged and discharged, so portable PCs, handy video cameras, information terminals, etc. It is widely used as a power source for portable electronic devices. From the viewpoint of environmental problems, electric vehicles using non-aqueous electrolyte secondary batteries and hybrid vehicles using electric power as part of power have been put into practical use.
  • Non-aqueous electrolyte secondary batteries are composed of members such as electrodes, separators, and electrolytes.
  • a flammable organic solvent is used as the main solvent for the electrolyte, and if a large amount of energy is released due to an internal short circuit, etc., thermal runaway occurs, and there is a risk of ignition or rupture.
  • Countermeasures are being considered.
  • a method using a porous film mainly composed of polyolefin as a separator see, for example, Patent Documents 1 and 2), in addition to the separator, a porous heat-resistant layer is provided between the positive electrode and the negative electrode.
  • a method of providing for example, refer to Patent Document 3
  • a method of coating the surface of an electrode active material with a metal oxide for example, refer to Patent Document 4
  • a method of using lithium-containing nickel oxide as a positive electrode active material for example, Patent Document 5
  • a method using an olivine type lithium phosphate compound as a positive electrode active material for example, refer to Patent Document 6
  • a method using a spinel lithium titanate compound as a negative electrode active material for example, Patent Document 7
  • a method using a nonflammable fluorine-based solvent as the main solvent of the electrolyte see, for example, Patent Documents 8 and 9
  • a solid-state battery that does not use an organic solvent as the electrolyte are known.
  • the battery becomes larger by the amount of the porous heat-resistant layer, and the electrode activity is increased.
  • the content of the electrode active material contained in the electrode mixture layer of the electrode is relatively reduced, and the capacity of the battery is reduced. The advantage of the non-aqueous electrolyte secondary battery is lost.
  • a method using a lithium-containing nickel oxide or an olivine-type lithium phosphate compound as a positive electrode active material nor a method using a spinel lithium titanate compound as a negative electrode active material can provide a high charge / discharge capacity.
  • the fluorinated solvent is very expensive and needs to be used in a large amount.
  • the method using a solid electrolyte since a solid electrolyte material having no fluidity is used, the internal resistance is increased, and the performance is deteriorated as compared with an electrolyte using an organic solvent.
  • a non-aqueous electrolyte in which a lithium salt containing a fluorine atom such as lithium hexafluorophosphate is dissolved in a carbonate organic solvent such as propylene carbonate or diethyl carbonate as an electrolyte is used.
  • Carboxylic acid silyl ester compounds see, for example, Patent Documents 11 to 13
  • sulfuric acid silyl ester compounds for example, see Patent Documents 4 to 5
  • sulfonic acid silyl ester compounds for example, see Patent Documents 14 and 16
  • silyl compounds such as phosphoric acid silyl ester compounds (for example, see Patent Documents 15, 17, and 18), boric acid silyl ester compounds (for example, see Patent Documents 15 and 19), etc.
  • Nonaqueous electrolytes to which an ester compound is further added have been studied.
  • An object of the present invention is to provide a non-aqueous electrolyte secondary battery that is less likely to cause thermal runaway and has no risk of ignition or rupture even if an internal short circuit occurs without increasing the size or significantly increasing the cost. is there.
  • the present inventors have obtained a non-aqueous electrolyte secondary battery having a non-aqueous electrolyte using an organic solvent as a solvent, by blending a silyl ester compound into the non-aqueous electrolyte, The inventors have found that thermal runaway is unlikely to occur and that ignition or rupture due to an internal short circuit can be prevented, and the present invention has been completed. That is, the present invention is an inhibitor of thermal runaway due to an internal short circuit for a positive electrode including a positive electrode active material, a negative electrode including a negative electrode active material, and a nonaqueous electrolyte secondary battery having a nonaqueous electrolyte, comprising a silyl ester compound. .
  • FIG. 1 is a longitudinal sectional view schematically showing an example of the structure of a coin-type battery of a nonaqueous electrolyte secondary battery.
  • FIG. 2 is a schematic diagram showing a basic configuration of a cylindrical battery of a nonaqueous electrolyte secondary battery.
  • FIG. 3 is a perspective view showing the internal structure of the cylindrical battery of the nonaqueous electrolyte secondary battery as a cross section.
  • the thermal runaway inhibitor of the present invention is characterized by comprising a silyl ester compound.
  • silyl ester compounds include carboxylic acid silyl ester compounds, sulfuric acid silyl ester compounds, sulfonic acid silyl ester compounds, phosphoric acid silyl ester compounds, phosphorous acid silyl ester compounds, boric acid silyl ester compounds, and the like.
  • Examples of the carboxylic acid silyl ester compound include a carboxylic acid silyl ester compound represented by the following general formula (1).
  • R 1 to R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms
  • X 1 represents an a-valent hydrocarbon group having 1 to 10 carbon atoms, or a hydrocarbon group
  • R 1 to R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms.
  • the hydrocarbon group having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and neopentyl.
  • R 1 to R 3 are preferably a methyl group, an ethyl group, or a phenyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • R 1 to R 3 may all be the same group or a combination of 2 to 3 groups, but in the case of a combination of 2 to 3 groups, one type is preferably a methyl group.
  • X 1 represents an a-valent hydrocarbon group having 1 to 10 carbon atoms, or an a-valent group having 1 to 10 carbon atoms in which a methylene group in the hydrocarbon group is substituted with an oxygen atom or a sulfur atom, Represents a number from 1 to 4. If the carbon number of X 1 is too large, the solubility in the non-aqueous electrolyte may decrease, or the effect of suppressing thermal runaway may be reduced. Therefore, the carbon number of X 1 is preferably 1 to 10, 1 to 6 are more preferable.
  • a is preferably a number of 2 to 3 from the viewpoint of the solubility of the carboxylic acid silyl ester compound in the non-aqueous electrolyte and the stability of the carboxylic acid silyl ester compound.
  • the carboxylic acid silyl ester compound represented by the general formula (1) can be obtained by silyl esterifying a carboxylic acid represented by the following general formula (1a) or an acid anhydride thereof by a known method.
  • the compound in which a is 1 includes trimethylsilyl acetate, trimethylsilyl propanoate, trimethylsilyl butanoate, trimethylsilyl pentanoate, trimethylsilyl hexanoate, trimethylsilyl heptanoate, octanoic acid Trimethylsilyl, trimethylsilyl nonanoate, trimethylsilyl decanoate, trimethylsilyl 2-methylpropanoate, trimethylsilyl 2-methylbutanoate, trimethylsilyl 3-methylbutanoate, trimethylsilyl tert-butanoate, trimethylsilyl 2-methylpentanoate, trimethylsilyl 2-ethylbutanoate, isohexanoic acid Trimethylsilyl, trimethylsilyl 2-ethylhexanoate, trimethylsilyl isooctanoate, 3,5,5-trimethyl
  • the compound in which a is 2 includes ethanedioic acid bis (trimethylsilyl), propanedioic acid bis (trimethylsilyl), butanedioic acid bis (trimethylsilyl), pentane.
  • the compound in which a is 3 includes propanetricarboxylic acid tris (trimethylsilyl), 3-carboxymuconic acid tris (trimethylsilyl), aconitic acid tris (trimethylsilyl), 3-Butene-1,2,3-tricarboxylic acid tris (trimethylsilyl), pentane-1,3,5-tricarboxylic acid tris (trimethylsilyl), hexane-1,3,6-tricarboxylic acid tris (trimethylsilyl), cyclohexanetricarboxylic acid Examples include tris (trimethylsilyl), trimellitic acid tris (trimethylsilyl), trimesic acid tris (trimethylsilyl), butanetetracarboxylic acid tris (trimethylsilyl), and the like.
  • compounds having a of 4 include cyclobutanetetracarboxylic acid tetrakis (trimethylsilyl), cyclopentanetetracarboxylic acid tetrakis (trimethylsilyl), tetrahydrofuran tetracarboxylic acid tetrakis ( Trimethylsilyl), pyromellitic acid tetrakis (trimethylsilyl), naphthalenetetracarboxylic acid tetrakis (trimethylsilyl) and the like.
  • Examples of the sulfuric acid silyl ester compound and the sulfonic acid silyl ester compound include compounds represented by the following general formula (3).
  • R 11 to R 14 each independently represents a hydrocarbon group having 1 to 6 carbon atoms, and c represents a number of 0 or 1).
  • R 11 to R 14 each represent a hydrocarbon group having 1 to 6 carbon atoms.
  • the hydrocarbon group having 1 to 6 carbon atoms include groups exemplified as R 1 to R 3 in the general formula (1).
  • R 11 is preferably a methyl group or a phenyl group, and more preferably a methyl group, because industrial raw materials are easily available.
  • R 12 to R 14 are preferably a methyl group, an ethyl group, or a phenyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • c represents a number of 0 or 1
  • the compound represented by the general formula (3) is a sulfated silyl ester compound, and when c is a number of 1, sulfonic acid It is a silyl ester compound.
  • c in formula (3) is a number of 0, that is, when the compound represented by formula (3) is a sulfated silyl ester compound, preferred compounds include bis (trimethylsilyl) sulfate and bis (dimethylphenylsulfate). Silyl), bis (methyldiphenylsilyl) sulfate, bis (triphenylsilyl) sulfate and the like.
  • c in the general formula (3) is a number of 1, that is, when the compound represented by the general formula (3) is a sulfonic acid silyl ester compound, preferred compounds include trimethylsilyl methanesulfonate and dimethylphenyl methanesulfonate. Examples thereof include silyl, trimethylsilyl benzenesulfonate, and trimethylsilyl toluenesulfonate.
  • Examples of the phosphoric acid silyl ester compound include alkyl acid phosphoric acid ester silyl ester compounds in which a part of the silyl ester group is substituted with an alkyl ester group.
  • the phosphorous acid silyl ester compound includes a part of the silyl ester group.
  • a phosphoric acid silyl ester compound and a phosphorous acid silyl ester compound the compound represented by following General formula (4) is mentioned, for example.
  • R 15 to R 18 each independently represents a hydrocarbon group having 1 to 6 carbon atoms, d represents 0 or a number of 1 to 2, and e represents a number of 0 or 1).
  • R 15 to R 18 each independently represents a hydrocarbon group having 1 to 6 carbon atoms.
  • the hydrocarbon group having 1 to 6 carbon atoms include groups exemplified as R 1 to R 3 in the general formula (1).
  • R 15 is preferably a methyl group, an ethyl group, or a butyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • R 16 to R 18 are preferably a methyl group, an ethyl group, or a phenyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • D represents 0 or a number from 1 to 2
  • e represents a number from 0 or 1.
  • d is a number from 1 to 2
  • a mixture of a compound having a number of 1 and a compound having a number of 2 can be used.
  • the compound represented by the general formula (4) is a phosphoric acid silyl ester compound, and when e is 1 and d is 1 or 2 Is a silyl ester compound of an alkyl acidic phosphate.
  • the compound represented by the general formula (4) is a phosphite silyl ester compound, wherein e is a number of 0 and d is a number of 1 to 2.
  • it is an alkyl acidic phosphite silyl ester compound.
  • the silyl ester compound of an alkyl acidic phosphate ester and the silyl ester compound of an alkyl acidic phosphite ester are easier to manufacture and storage stability than the silyl phosphate compound and the phosphite silyl ester compound, respectively. There is an advantage that it is excellent.
  • Examples of phosphoric acid silyl ester compounds include tris (trimethylsilyl) phosphate, methylbis (trimethylsilyl) phosphate, dimethyl (trimethylsilyl) phosphate, ethylbis (trimethylsilyl) phosphate, phosphorus Examples thereof include diethyl acid (trimethylsilyl), butylbisphosphate (trimethylsilyl), and dibutyl phosphate (trimethylsilyl).
  • Phosphite silyl ester compounds include tris (trimethylsilyl) phosphite, methylbis (trimethylsilyl) phosphite, dimethyl phosphite (trimethylsilyl), phosphorous acid Examples thereof include ethyl bis (trimethylsilyl), diethyl phosphite (trimethylsilyl), butyl bisphosphite (trimethylsilyl), and dibutyl phosphite (trimethylsilyl).
  • boric acid silyl ester compound examples include compounds represented by the following general formula (5).
  • R 19 to R 21 each independently represents a hydrocarbon group having 1 to 6 carbon atoms.
  • R 19 to R 21 each independently represents a hydrocarbon group having 1 to 6 carbon atoms.
  • the hydrocarbon group having 1 to 6 carbon atoms include groups exemplified as R 1 to R 3 in the general formula (1).
  • R 19 to R 21 are preferably a methyl group, an ethyl group, or a phenyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • the boric acid silyl ester compound include tris borate (trimethylsilyl).
  • a carboxylic acid silyl ester compound represented by the general formula (1) since the effect of suppressing thermal runaway is high, it is preferable to use a carboxylic acid silyl ester compound represented by the general formula (1).
  • a in the general formula (1) is preferably 2, and X 1 is a divalent hydrocarbon group having 1 to 10 carbon atoms, or a methylene group in the hydrocarbon group is an oxygen atom or a sulfur atom. It is preferably a substituted divalent group having 1 to 10 carbon atoms.
  • R 1 to R 3 in the general formula (1) are methyl groups, a is 2, and X 1 is a divalent hydrocarbon group having 1 to 6 carbon atoms, or methylene in the hydrocarbon group A compound in which the group is a divalent group having 1 to 6 carbon atoms substituted with a sulfur atom is preferred.
  • a silyl ester compound is blended in the non-aqueous electrolyte as a thermal runaway inhibitor.
  • the content of the silyl ester compound in the nonaqueous electrolyte is preferably 0.01% by mass to 10% by mass, more preferably 0.05% by mass to 7% by mass, and most preferably 0.1% by mass to 5% by mass. .
  • the content of the silyl ester compound in the non-aqueous electrolyte is too small, a sufficient effect of suppressing thermal runaway cannot be obtained, and when it is too large, the effect of increasing the amount corresponding to the blending amount cannot be obtained.
  • silyl ester compound in the nonaqueous electrolyte suppresses thermal runaway due to an internal short circuit in the nonaqueous electrolyte secondary battery
  • siloxane compounds adhere to the positive and negative electrode surfaces of the nonaqueous electrolyte secondary battery. Therefore, it is presumed that the silyl ester compound is decomposed by the charge / discharge process to produce a siloxane compound on the electrode surface, which insulates the short-circuit current.
  • nonaqueous electrolyte of the nonaqueous electrolyte secondary battery to which the present invention can be applied examples include a liquid electrolyte obtained by dissolving an electrolyte in an organic solvent, and a polymer gel electrolyte obtained by dissolving the electrolyte in an organic solvent and gelling with a polymer.
  • a pure polymer electrolyte in which an organic solvent is not contained and an electrolyte is dispersed in a polymer can be used.
  • the thermal runaway inhibitor of the present invention is a nonaqueous electrolyte having a liquid electrolyte. It is preferable to apply to a non-aqueous electrolyte of a secondary battery.
  • the electrolyte used for the liquid electrolyte and the polymer gel electrolyte a conventionally known electrolyte is used.
  • an electrolyte in the case where the nonaqueous electrolyte secondary battery is a lithium secondary battery will be described.
  • an electrolyte in which lithium atoms are replaced with sodium atoms is used.
  • the electrolyte used for the liquid electrolyte and the polymer gel electrolyte include LiPF 6 , LiBF 4 , LiAsF 6 , LiCF 3 SO 3 , LiCF 3 CO 2 , LiN (CF 3 SO 2 ) 2 , LiN (C 2 F 5 SO 2 ).
  • Examples of the electrolyte used for the pure polymer electrolyte include LiN (CF 3 SO 2 ) 2 , LiN (C 2 F 5 SO 2 ) 2 , LiN (SO 2 F) 2 , LiC (CF 3 SO 2 ) 3 , LiB. (CF 3 SO 3 ) 4 and LiB (C 2 O 4 ) 2 may be mentioned.
  • organic solvent used for the preparation of the liquid non-aqueous electrolyte used in the present invention those usually used for non-aqueous electrolytes can be used alone or in combination of two or more. Specific examples include saturated cyclic carbonate compounds, saturated cyclic ester compounds, sulfoxide compounds, sulfone compounds, amide compounds, saturated chain carbonate compounds, chain ether compounds, cyclic ether compounds, and saturated chain ester compounds. .
  • saturated cyclic carbonate compounds saturated cyclic ester compounds, sulfoxide compounds, sulfone compounds, and amide compounds are preferable because they have a high relative dielectric constant, and therefore play a role in increasing the dielectric constant of nonaqueous electrolytes.
  • a carbonate compound is preferred.
  • the saturated cyclic carbonate compound include ethylene carbonate, 1,2-propylene carbonate, 1,3-propylene carbonate, 1,2-butylene carbonate, 1,3-butylene carbonate, 1,1-dimethylethylene carbonate, and the like. It is done.
  • saturated cyclic ester compound examples include ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -hexanolactone, and ⁇ -octanolactone.
  • sulfoxide compound examples include dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diphenyl sulfoxide, thiophene, and the like.
  • sulfone compound examples include dimethyl sulfone, diethyl sulfone, dipropyl sulfone, diphenyl sulfone, sulfolane (also referred to as tetramethylene sulfone), 3-methyl sulfolane, 3,4-dimethyl sulfolane, 3,4-diphenmethyl sulfolane. , Sulfolane, 3-methylsulfolene, 3-ethylsulfolene, 3-bromomethylsulfolene and the like, and sulfolane and tetramethylsulfolane are preferable.
  • the amide compound examples include N-methylpyrrolidone, dimethylformamide, dimethylacetamide and the like.
  • saturated chain carbonate compounds, chain ether compounds, cyclic ether compounds and saturated chain ester compounds can reduce the viscosity of the nonaqueous electrolyte and increase the mobility of electrolyte ions. Battery characteristics such as output density can be made excellent. Moreover, since it is low-viscosity, the performance of the nonaqueous electrolyte at low temperature can be enhanced, and therefore saturated chain carbonate compounds are particularly preferable.
  • the saturated chain carbonate compound include dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, ethyl butyl carbonate, methyl-t-butyl carbonate, diisopropyl carbonate, t-butyl propyl carbonate, and the like.
  • Examples of the chain ether compound or the cyclic ether compound include dimethoxyethane, ethoxymethoxyethane, diethoxyethane, tetrahydrofuran, dioxolane, dioxane, 1,2-bis (methoxycarbonyloxy) ethane, 1,2-bis ( Ethoxycarbonyloxy) ethane, 1,2-bis (ethoxycarbonyloxy) propane, ethylene glycol bis (trifluoroethyl) ether, propylene glycol bis (trifluoroethyl) ether, ethylene glycol bis (trifluoromethyl) ether, diethylene glycol bis (Trifluoroethyl) ether and the like can be mentioned, and among these, dioxolane is preferable.
  • saturated chain ester compound monoester compounds and diester compounds having a total number of carbon atoms in the molecule of 2 to 8 are preferable, and specific compounds include, for example, methyl formate, ethyl formate, methyl acetate, acetic acid Ethyl, propyl acetate, isobutyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, methyl isobutyrate, methyl trimethyl acetate, ethyl trimethyl acetate, methyl malonate, ethyl malonate, methyl succinate, ethyl succinate, Examples include methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethylene glycol diacetyl, propylene glycol diacetyl, and the like.
  • Methyl formate, ethyl formate, methyl acetate, ethyl acetate, propyl acetate, isobutyl acetate, butyl acetate, methyl propionate And ethyl propionate are preferred.
  • organic solvent used for preparing the non-aqueous electrolyte for example, acetonitrile, propionitrile, nitromethane, derivatives thereof, and various ionic liquids can be used.
  • Examples of the polymer used in the polymer gel electrolyte include polyethylene oxide, polypropylene oxide, polyvinyl chloride, polyacrylonitrile, polymethyl methacrylate, polyethylene, polyvinylidene fluoride, and polyhexafluoropropylene.
  • Examples of the polymer used in the pure polymer electrolyte include polyethylene oxide, polypropylene oxide, and polystyrene sulfonic acid.
  • the non-aqueous electrolyte preferably further contains a phenylsilane compound represented by the general formula (2) because the stability of the silyl ester compound is improved.
  • R 4 to R 5 each independently represents a hydrocarbon group having 1 to 6 carbon atoms
  • R 6 to R 10 each independently represents a hydrogen atom, a halogen atom, or a carbon number of 1 to 4
  • X 2 represents a b-valent hydrocarbon group, and b represents a number of 1 to 3.
  • R 4 to R 5 each independently represents a hydrocarbon group having 1 to 6 carbon atoms.
  • the hydrocarbon group having 1 to 6 carbon atoms include groups exemplified as R 1 to R 3 in the general formula (1).
  • R 4 to R 5 are preferably a methyl group, an ethyl group, or a phenyl group, and more preferably a methyl group, since the effect of suppressing thermal runaway is increased.
  • R 6 to R 10 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and iodine.
  • the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, A tert-butyl group may be mentioned.
  • R 6 to R 10 are preferably hydrogen atoms because the raw materials are easily industrially available.
  • X 2 represents a b-valent hydrocarbon group, and b represents a number of 1 to 3.
  • b represents a number of 1 to 3.
  • preferred compounds include trimethylphenylsilane, dimethyldiphenylsilane, methyltriphenylsilane, butyldimethylphenylsilane, dimethyloctylphenylsilane, 1,4-bis ( And trimethylsilyl) benzene, 1,2-bis (trimethylsilyl) benzene, 1,4-bis (dimethylphenylsilyl) benzene, 1,1,1-tris (dimethylphenylsilyl) ethane, and the like.
  • Some electrolytes used in non-aqueous electrolytes decompose to generate acidic substances.
  • Such acidic substances can reduce the performance of non-aqueous electrolyte secondary batteries or decompose silyl ester compounds. May end up.
  • the phenylsilane compound represented by the general formula (2) captures such an acidic substance, and suppresses the deterioration of the performance of the nonaqueous electrolyte secondary battery and the decomposition of the silyl ester compound.
  • the amount of the phenylsilane compound represented by the general formula (2) added to the non-aqueous electrolyte is preferably 0.1% by mass to 10% by mass, more preferably 0.5% by mass to 7% by mass, and more preferably 1% by mass to 5% by mass is most preferred.
  • the content in the non-aqueous electrolyte is too small, a sufficient effect cannot be exhibited.
  • the content is too large, the effect of increasing the amount corresponding to the amount added is not seen, and the battery performance may be deteriorated.
  • the nonaqueous electrolyte may contain an electrode film forming agent.
  • the electrode film forming agent include cyclic carbonate compounds having an unsaturated group such as vinylene carbonate and vinyl ethylene carbonate; chain carbonate compounds having a propynyl group such as dipropargyl carbonate and propargylmethyl carbonate; dimethyl maleate, dibutyl maleate, Unsaturated diester compounds such as dimethyl fumarate, dibutyl fumarate, dimethyl acetylenedicarboxylate; halogenated cyclic carbonate compounds such as chloroethylene carbonate, dichloroethylene carbonate, fluoroethylene carbonate, difluoroethylene carbonate; cyclic sulfites such as ethylene sulfite; Examples thereof include cyclic sulfates such as propane sultone and butane sultone.
  • the electrode film forming agent forms a protective film called SEI (Solid Electrolyte Interface) on the electrode surface, and improves the charge / discharge efficiency, cycle characteristics, and safety of the battery. If the content of the electrode film forming agent is too small, it will not be able to exert a sufficient effect, and if it is too large, it will not be possible to obtain an increase effect commensurate with the content, but may have an adverse effect. Therefore, the content of the electrode film forming agent is preferably 0.005% by mass to 10% by mass, more preferably 0.02% by mass to 5% by mass in the non-aqueous electrolyte, and 0.05% by mass to 3% by mass. % Is most preferred.
  • SEI Solid Electrolyte Interface
  • the non-aqueous electrolyte may further contain other known additives such as an antioxidant, a flame retardant, and an overcharge inhibitor, for example, in order to improve battery life and safety.
  • additives such as an antioxidant, a flame retardant, and an overcharge inhibitor, for example, in order to improve battery life and safety.
  • a positive electrode including a positive electrode active material of a nonaqueous electrolyte secondary battery to which the present invention is applied is an electrode in which an electrode mixture layer including a positive electrode active material is formed on a current collector.
  • a slurry obtained by slurrying a binder and a conductive additive with an organic solvent or water is applied to a current collector and dried to form a sheet.
  • the positive electrode active material of the positive electrode As the positive electrode active material of the positive electrode, a known positive electrode active material can be used.
  • the electrolyte in the case where the nonaqueous electrolyte secondary battery is a lithium secondary battery will be described.
  • a positive electrode active material in which lithium atoms are replaced with sodium atoms is used.
  • Known positive electrode active materials for lithium secondary batteries include, for example, lithium transition metal composite oxides, lithium-containing transition metal phosphate compounds, lithium-containing silicate compounds, lithium-containing transition metal sulfate compounds, sulfur, and sulfur-containing materials. Compounds and the like.
  • the transition metal of the lithium transition metal composite oxide is preferably vanadium, titanium, chromium, manganese, iron, cobalt, nickel, copper or the like.
  • Specific examples of the lithium transition metal composite oxide include lithium cobalt composite oxide such as LiCoO 2 , lithium nickel composite oxide such as LiNiO 2 , and lithium manganese composite oxide such as LiMnO 2 , LiMn 2 O 4 , and Li 2 MnO 3.
  • transition metal atoms that are the main components of these lithium transition metal composite oxides are aluminum, titanium, vanadium, chromium, manganese, iron, cobalt, lithium, nickel, copper, zinc, magnesium, gallium, zirconium, etc. The thing substituted with the other metal etc. are mentioned.
  • transition metal of the lithium-containing transition metal phosphate compound vanadium, titanium, manganese, iron, cobalt, nickel and the like are preferable, and specific examples include LiFePO 4 , LiMn x Fe 1-x PO 4 (0 ⁇ Iron phosphate compounds such as x ⁇ 1), cobalt phosphate compounds such as LiCoPO 4 , and some of the transition metal atoms that are the main components of these lithium transition metal phosphate compounds are aluminum, titanium, vanadium, chromium, manganese , Iron, cobalt, lithium, nickel, copper, zinc, magnesium, gallium, zirconium, niobium and other metal-substituted compounds, and Li 3 V 2 (PO 4 ) 3 vanadium phosphate compounds, etc.
  • lithium-containing silicate compound examples include Li 2 FeSiO 4 .
  • lithium-containing transition metal sulfate compound examples include LiFeSO 4 and LiFeSO 4 F. These can use only 1 type and can also be used in combination of 2 or more type.
  • the thermal runaway inhibitor of the present invention can be suitably used for a nonaqueous electrolyte secondary battery having a large charge / discharge capacity.
  • the inhibitor can be suitably used for nonaqueous electrolyte secondary batteries having these positive electrode active materials.
  • binder examples include polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), ethylene-propylene-diene copolymer (EPDM), styrene-butadiene rubber (SBR), acrylonitrile butadiene rubber (NBR), and styrene- Isoprene copolymer, polymethyl methacrylate, polyacrylate, polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC), sodium carboxymethyl cellulose (CMCNa), methyl cellulose (MC), starch, polyvinyl pyrrolidone, polyethylene (PE), polypropylene (PP) , Polyethylene oxide (PEO), polyimide (PI), polyamideimide (PAI), polyacrylonitrile (PAN), polyvinyl chloride (PVC) Polyacrylic acid, and polyurethane.
  • the amount of the binder used is usually about 1% by mass to 20% by mass, preferably 2% by mass to 10% by mass with
  • the conductive aid examples include carbon black, ketjen black, acetylene black, channel black, furnace black, lamp black, thermal black, carbon nanotube, vapor grown carbon fiber (VGCF), graphene, fullerene Carbon materials such as needle coke; metal powders such as aluminum powder, nickel powder and titanium powder; conductive metal oxides such as zinc oxide and titanium oxide; La 2 S 3 , Sm 2 S 3 , Ce 2 S 3 and TiS 2 and the like.
  • the average particle size of the conductive auxiliary agent is preferably 0.0001 ⁇ m to 100 ⁇ m, and more preferably 0.01 ⁇ m to 50 ⁇ m.
  • an organic solvent or water that dissolves the binder is used as the solvent to be slurried.
  • the organic solvent include N-methylpyrrolidone, dimethylformamide, dimethylacetamide, methyl ethyl ketone, cyclohexanone, methyl acetate, methyl acrylate, diethyltriamine, NN-dimethylaminopropylamine, ethylene oxide, tetrahydrofuran and the like.
  • the amount of the solvent used is usually about 10% by mass to 400% by mass, preferably 20% by mass to 200% by mass with respect to the positive electrode active material.
  • the positive electrode current collector aluminum, stainless steel, nickel-plated steel or the like is usually used.
  • the shape of the current collector include a foil shape, a plate shape, and a mesh shape, and a foil shape is preferable.
  • the thickness of the foil is usually 1 ⁇ m to 100 ⁇ m.
  • the negative electrode including the negative electrode active material of the nonaqueous electrolyte secondary battery to which the present invention is applied is an electrode in which an electrode mixture layer including a negative electrode active material is formed on a current collector.
  • a slurry obtained by slurrying a binder and a conductive additive with an organic solvent or water is applied to a current collector and dried to form a sheet.
  • the negative electrode active material of the negative electrode As the negative electrode active material of the negative electrode, a known negative electrode active material can be used.
  • the electrolyte in the case where the nonaqueous electrolyte secondary battery is a lithium secondary battery will be described.
  • the lithium atom of the negative electrode active material having a lithium atom among the negative electrode active materials is replaced by a sodium atom.
  • the replaced negative electrode active material is used.
  • Known negative electrode active materials include carbonaceous materials, lithium, lithium alloys, silicon, silicon alloys, silicon oxide, tin, tin alloys, tin oxide, phosphorus, germanium, indium, copper oxide, antimony sulfide, titanium oxide, iron oxide , Manganese oxide, Cobalt oxide, Nickel oxide, Lead oxide, Ruthenium oxide, Tungsten oxide, Zinc oxide, LiVO 2 , Li 2 VO 4 , Li 4 Ti 5 O 12 and other complex oxides, conductive polymer, sulfur modified Examples include polyacrylonitrile.
  • the carbonaceous material is not particularly limited, however, natural graphite, artificial graphite, fullerene, graphene, graphite fiber chop, carbon nanotube, graphite whisker, highly oriented pyrolytic graphite, quiche graphite and other non-graphitizable carbon , Graphitizable carbon, petroleum coke, coal coke, petroleum pitch carbide, coal pitch carbide, phenolic resin, crystalline cellulose resin carbide, etc., and partially carbonized carbon materials, furnace black Acetylene black, pitch-based carbon fiber, polyacrylonitrile-based carbon fiber, and the like.
  • the positive electrode active material is sulfur-modified polyacrylonitrile
  • a negative electrode active material other than sulfur-modified polyacrylonitrile is used as the negative electrode active material.
  • binder examples of the binder, the conductive additive, and the solvent to be slurried are the same as those for the positive electrode.
  • the amount of the binder used is usually about 1% by mass to 30% by mass, preferably about 2% by mass to 15% by mass with respect to the negative electrode active material.
  • the amount of the solvent used is usually about 10% by mass to 400% by mass, preferably 20% by mass to 200% by mass with respect to the negative electrode active material.
  • Copper, nickel, stainless steel, nickel-plated steel, aluminum, etc. are usually used for the negative electrode current collector.
  • Examples of the shape of the current collector include a foil shape, a plate shape, and a mesh shape, and a foil shape is preferable.
  • the thickness of the foil is usually 1 ⁇ m to 100 ⁇ m.
  • a separator is used between the positive electrode and the negative electrode, and a commonly used polymer microporous film can be used without particular limitation.
  • the film include polyethylene, polypropylene, polyvinylidene fluoride, polyvinylidene chloride, polyacrylonitrile, polyacrylamide, polytetrafluoroethylene, polysulfone, polyethersulfone, polycarbonate, polyamide, polyimide, polyethylene oxide, polypropylene oxide, and the like.
  • celluloses such as carboxymethyl cellulose and hydroxypropyl cellulose, polymer compounds mainly composed of poly (meth) acrylic acid and various esters thereof, derivatives thereof, films made of copolymers or mixtures thereof, etc. These films may be coated with ceramic materials such as alumina and silica, magnesium oxide, aramid resin, and polyvinylidene fluoride. That. When the nonaqueous solvent electrolyte is a pure polymer electrolyte, the separator may not be included.
  • the nonaqueous electrolyte secondary battery to which the present invention is applied is a single battery, a stacked battery in which a positive electrode and a negative electrode are laminated in multiple layers via a separator, a long sheet separator, a positive electrode and a negative electrode.
  • a rechargeable battery any form such as a rechargeable battery may be used, the charge / discharge capacity of the battery is high, and thermal runaway due to an internal short circuit is likely to occur, so the present invention provides a stacked nonaqueous electrolyte secondary battery or a wound rechargeable battery. It is preferable to apply to a non-aqueous electrolyte secondary battery.
  • LiPF 6 was dissolved in a mixed solvent composed of 50% by volume of ethylene carbonate and 50% by volume of diethyl carbonate to a concentration of 1.0 mol / L to obtain a nonaqueous electrolyte A.
  • non-aqueous electrolytes B to E The non-aqueous electrolytes A to G were obtained by dissolving the additives shown in Table 1 in the non-aqueous electrolyte A so as to have the indicated concentrations.
  • This slurry composition was continuously applied on both surfaces of a roll-shaped aluminum foil (thickness 20 ⁇ m) current collector by a comma coater method, and dried at 90 ° C. for 3 hours.
  • This roll is cut into 50 mm length and 90 mm width, the electrode mixture layer on one side of the horizontal side (short side) is removed 10 mm from the end, the current collector is exposed, and then vacuum dried at 150 ° C. for 2 hours
  • the positive electrode 1 was produced.
  • This slurry composition was continuously applied on both sides of a roll-shaped copper foil (thickness 10 ⁇ m) current collector by a comma coater method, and dried at 90 ° C. for 3 hours.
  • This roll is cut to 55 mm length and 95 mm width, the electrode mixture layer on one side of the horizontal side (short side) is removed 10 mm from the end, the current collector is exposed, and then vacuum dried at 150 ° C. for 2 hours
  • the negative electrode 1 was produced.
  • negative electrode 2 As the electrode active material, in place of 92.0 parts by mass of massive artificial graphite, negative electrode 1 except that 87.0 parts by mass of massive artificial graphite and 5.0 parts by mass of silicon oxide (average particle diameter: 5 ⁇ m) were used. A negative electrode 2 was produced by the same procedure.
  • a positive electrode and a negative electrode are laminated via a separator (manufactured by Celgard, trade name: Cellguard 2325) so that the battery capacity shown in Table 2 is obtained, and a positive electrode terminal and a negative electrode terminal are provided on the positive electrode and the negative electrode, respectively, to obtain a laminate. It was.
  • the obtained laminate and nonaqueous electrolytes A to G were accommodated in a flexible film, and laminated laminate batteries of Examples 1 to 8 and Comparative Examples 1 to 6 were obtained.
  • a non-aqueous electrolyte that is small and lightweight, has a high capacity, is resistant to thermal runaway even when an internal short circuit occurs, and has no risk of ignition or rupture, without increasing the size or significantly increasing the cost.
  • a secondary battery can be provided.

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Abstract

La présente invention aborde le problème de la fourniture d'une batterie secondaire à électrolyte non aqueux qui n'a pas d'emballement thermique si un court-circuit interne se produit et aucun risque d'incendie ou d'explosion, sans augmenter la taille ni augmenter considérablement le coût. Cet agent pour supprimer un emballement thermique provoqué par des courts-circuits internes est destiné à une batterie secondaire à électrolyte non aqueux ayant : une électrode positive comprenant une substance active d'électrode positive comprenant un composé d'ester de silyle ; une électrode négative comprenant une substance active d'électrode négative, et un électrolyte non aqueux. Dans ce procédé de suppression d'emballement thermique provoqué par des courts-circuits internes dans des batteries secondaires à électrolyte non aqueux, 0,01 % à 10 % en masse de l'agent pour supprimer un emballement thermique provoqué par des courts-circuits internes, destinés à être utilisés dans des batteries secondaires à électrolyte non aqueux, est mélangé à l'électrolyte non aqueux.
PCT/JP2019/010401 2018-03-23 2019-03-13 Agent de suppression d'emballement thermique Ceased WO2019181704A1 (fr)

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