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WO2015037382A1 - Solution électrolytique et batterie secondaire - Google Patents

Solution électrolytique et batterie secondaire Download PDF

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Publication number
WO2015037382A1
WO2015037382A1 PCT/JP2014/071281 JP2014071281W WO2015037382A1 WO 2015037382 A1 WO2015037382 A1 WO 2015037382A1 JP 2014071281 W JP2014071281 W JP 2014071281W WO 2015037382 A1 WO2015037382 A1 WO 2015037382A1
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group
substituted
carbon atoms
unsubstituted
electrolytic solution
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Japanese (ja)
Inventor
信也 須藤
伊紀子 島貫
川崎　大輔
石川　仁志
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NEC Corp
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NEC 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
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to an electrolytic solution and a secondary battery including the electrolytic solution.
  • One method for improving the performance of the secondary battery is to suppress the decomposition reaction of the electrolyte by forming a protective film on the electrode surface.
  • a method of forming a film on the electrode surface by adding an additive to the electrolytic solution has been proposed.
  • Patent Document 1 discloses a lithium ion secondary battery having an electrolytic solution containing a chain disulfonic acid ester compound and a cyclic monosulfonic acid ester compound or a chain disulfonic acid ester compound.
  • Patent Document 2 discloses at least one compound selected from a cyclic carbonate compound having an unsaturated bond and an acid anhydride, a sulfur-containing organic compound, a fluorine-containing aromatic compound having 9 or less carbon atoms, and an aliphatic hydrocarbon compound. And a secondary battery having an electrolytic solution containing at least one compound selected from fluorine-containing aliphatic hydrocarbon compounds.
  • Patent Document 3 has an electrolyte containing an aprotic solvent and a chain disulfonic acid ester compound, and has a negative electrode containing an oxide that absorbs and releases alkali metal or alkaline earth metal as a negative electrode active material.
  • a secondary battery is described.
  • Patent Document 4 discloses a secondary battery having a positive electrode including a lithium-containing composite oxide having an electrolytic solution containing an aprotic solvent and a chain disulfonic acid ester compound and having a charge / discharge region at 4.3 V or higher. Is described.
  • Patent Document 5 contains a monofluorophosphate and / or a difluorophosphate, and further includes a compound represented by a predetermined formula, a nitrile compound, an isocyanate compound, a phosphazene compound, a disulfonic acid ester compound, a sulfide compound, and a disulfide.
  • a nonaqueous electrolytic solution containing at least one compound selected from the group consisting of a compound, an acid anhydride, a lactone compound having a substituent at the ⁇ -position, and a compound having a carbon-carbon triple bond is described.
  • Patent Document 6 or 7 describes an electrolytic solution containing a sulfonic acid ester compound represented by a predetermined formula.
  • Patent Document 8 describes a secondary battery having an electrolytic solution containing a chain disulfonic acid ester compound.
  • Patent Document 9 describes a secondary battery having an electrolytic solution containing a chain disulfonic acid ester compound represented by the formula (II).
  • Patent Document 10 discloses a cyclic sulfonic acid ester compound having two sulfonyl groups.
  • Non-Patent Documents 1 to 3 disclose a method for producing a chain disulfonic acid ester compound.
  • An object of the present invention is to provide an electrolytic solution that has an excellent capacity retention rate and can suppress gas generation.
  • One of the embodiments is An electrolytic solution containing a supporting salt, a nonaqueous solvent that dissolves the supporting salt, a chain disulfone compound represented by the following formula (1), and an acid anhydride.
  • R 1 and R 2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 5 carbon atoms, —SO 2 X 1 (X 1 Is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), -SY 1 (Y 1 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), -COZ (Z is A hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), or a halogen atom, R 3 and R 4 each independently represents a hydrogen atom, a substituted or unsubstit
  • One of the embodiments is a secondary battery having the above electrolytic solution.
  • Electrolytic Solution The electrolytic solution of the present embodiment includes a supporting salt, a nonaqueous solvent that dissolves the supporting salt, a chain disulfone compound represented by the formula (1), and an acid anhydride.
  • the capacity retention rate of the secondary battery can be improved, but it has been found that gas generation accompanying charging / discharging increases and the volume increase of the battery increases. .
  • an acid anhydride to an electrolytic solution containing a chain disulfone compound, even when the chain disulfone compound is included, gas generation can be suppressed while maintaining the effect of improving the capacity retention rate. I understood.
  • the following reason can be considered as a mechanism of the synergistic effect which suppresses gas generation by adding an acid anhydride to the electrolyte solution containing a chain
  • the chain disulfone compound represented by the formula (1) is decomposed by an electrochemical oxidation-reduction reaction during the charge / discharge reaction to form a film on the surface of the negative electrode, and decomposes the electrolytic solution and the supporting salt.
  • the chain disulfone compound alone can be suppressed, gas generation accompanying charge / discharge increases.
  • an acid anhydride is further added to the electrolyte solution in addition to the chain disulfone compound, the acid anhydride will be decomposed before the chain disulfonic acid at the first charge, and excessive decomposition of the chain disulfone compound will occur. Is suppressed.
  • an acid anhydride contributes also in formation of a film
  • the above theory is estimation and does not restrict
  • the chain disulfone compound in the present embodiment is represented by the following formula (1).
  • R 1 and R 2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 5 carbon atoms, —SO 2 X 1 (X 1 Is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), -SY 1 (Y 1 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), -COZ (Z is A hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), or a halogen atom, R 3 and R 4 each independently represents a hydrogen atom, a substituted or unsubstit
  • fluoroalkyl group and “fluoroalkoxy group” each represent a group in which at least one hydrogen atom bonded to a carbon atom of a corresponding alkyl group or alkoxy group is substituted with a fluorine atom.
  • Fluoroalkyl group and “fluoroalkoxy group” are concepts including “perfluoroalkyl group” and “perfluoroalkoxy group”, respectively.
  • the “perfluoroalkyl group” and “perfluoroalkoxy group” represent groups in which all of the hydrogen atoms bonded to the carbon atoms of the corresponding alkyl group and alkoxy group are substituted with fluorine atoms, respectively.
  • n is preferably 1 or 2, and more preferably 1.
  • R 1 and R 2 are independent for each carbon atom to which they are bonded.
  • substituent for R 1 and R 2 include halogen atoms such as a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom, a hydroxy group, an amino group, an alkyl group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms. Examples thereof include an alkoxy group, a fluoroalkyl group having 1 to 4 carbon atoms, and a fluoroalkoxy group having 1 to 4 carbon atoms.
  • R 1 and R 2 may each independently have one substituent and may have a plurality of substituents.
  • R 3 and R 4 examples include a halogen atom such as a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom, a hydroxy group, an amino group, an alkyl group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms.
  • R 3 and R 4 may each independently have one substituent and may have a plurality of substituents.
  • the alkyl group, alkoxy group, fluoroalkyl group, and fluoroalkoxy group may be linear or branched.
  • the alkyl group, alkoxy group, fluoroalkyl group, and fluoroalkoxy group may be linear or branched.
  • substituent in the “fluoroalkyl group” or “fluoroalkoxy group” is a substituent other than a fluorine atom.
  • chain disulfone compound one kind may be used alone, or two or more kinds may be used in combination.
  • n is preferably 1, and is preferably a compound represented by the following formula (2).
  • R 1 ⁇ R 4 are the same as R 1 ⁇ R 4 described for the above equation (1).
  • the chain disulfone compound represented by the formula (1) or (2) is an acyclic compound and can be produced without a cyclization reaction at the time of synthesis.
  • Non-Patent Documents 1 to 3 Can be synthesized. It can also be obtained as a by-product of the synthesis of the cyclic disulfonic acid ester disclosed in Patent Document 10.
  • the chain disulfone compound represented by the formula (1) is easy to synthesize, there is a possibility that an inexpensive electrolytic solution can be provided.
  • R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted fluoroalkyl group having 1 to 5 carbon atoms. preferable.
  • R 1 and R 2 are more preferably each independently a hydrogen atom or a methyl group.
  • R 1 and R 2 are each particularly preferably a hydrogen atom.
  • n is 1, if R 1 and R 2 are hydrogen atoms, a methylene moiety sandwiched between two sulfonyl groups is activated, and reductive decomposition and film formation on the negative electrode are likely to occur.
  • R 3 and R 4 in formula (1) or (2) are each independently substituted or unsubstituted carbon from the viewpoints of stability of the compound, ease of synthesis of the compound, solubility in a solvent, price, and the like.
  • R 3 and R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted carbon group having 1 to 5 carbon atoms. More preferably, it is a 5 fluoroalkyl group, a substituted or unsubstituted fluoroalkoxy group having 1 to 5 carbon atoms, or a substituted or unsubstituted phenoxy group.
  • R 3 and R 4 are more preferably each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms. Further, it is particularly preferable that one or both of R 3 and R 4 is a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms.
  • the substituted or unsubstituted alkyl group having 1 to 5 carbon atoms is preferably a methyl group or an ethyl group
  • the substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms is preferably a methoxy group or An ethoxy group is preferred.
  • the compound represented by the formula (1) particularly the compound represented by the formula (2) has a small LUMO because it has two sulfonyl groups, and solvent molecules and monosulfonic acids generally used in electrolytes. It has a smaller LUMO value than the ester. Therefore, the compound is easily reduced.
  • the following compound No. The LUMO of 1 is ⁇ 0.86 eV, which is a small value, according to semiempirical molecular orbital calculation.
  • the compound No. 1 is preceded by a solvent (LUMO: about 1.2 eV) composed of cyclic carbonates and chain carbonates. 1 reduction film is formed on the negative electrode.
  • membrane formed in the negative electrode plays the role which suppresses decomposition
  • the compound represented by the formula (2) has a form in which an electron-withdrawing sulfonyl group is bonded to a carbon atom via a methylene group, and reduction on the negative electrode by activation of the carbon atom of the methylene group. It is considered that decomposition and film formation are likely to occur.
  • chain disulfone compound represented by the formula (1) Specific examples of the chain disulfone compound represented by the formula (1) are shown below, but the present invention is not particularly limited thereto.
  • a chain disulfone compound may be used individually by 1 type, or may use 2 or more types together.
  • the content of the chain disulfone compound represented by the formula (1) in the electrolytic solution is not particularly limited, but is preferably 0.005 to 10% by mass. When the content of the chain disulfone compound is 0.005% by mass or more, a film forming effect can be sufficiently obtained. Moreover, when content of a chain
  • the content of the chain disulfone compound in the electrolytic solution is more preferably 0.01% by mass or more, further preferably 0.1% by mass or more, and particularly preferably 0.5% by mass or more. preferable.
  • the content of the chain disulfone compound in the electrolytic solution is more preferably 8% by mass or less, further preferably 5% by mass or less, and particularly preferably 3% by mass or less.
  • the acid anhydride in this embodiment is a compound having at least one acid anhydride structure in one molecule, and the type of acid anhydride is not limited.
  • the acid anhydride may be a compound having a plurality of acid anhydride structures in one molecule.
  • Examples of the acid anhydride in the present embodiment include an anhydride of carboxylic acid, an anhydride of sulfonic acid, and an anhydride of carboxylic acid and sulfonic acid.
  • carboxylic acid anhydrides include acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, crotonic anhydride, trifluoroacetic anhydride, pentafluoropropionic anhydride, glutaric anhydride, maleic anhydride, citraconic anhydride , Glutaconic anhydride, itaconic anhydride, diglycolic anhydride, cyclohexanedicarboxylic anhydride, cyclopentanetetracarboxylic dianhydride, 4-cyclohexene-1,2-dicarboxylic anhydride, 3,4,5,6- Tetrahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, phenylsuccinic anhydride, 2-phenylglutaric anhydride, phthalic anhydride, pyromellitic anhydride, fluorosuccinic anhydride, tetra
  • sulfonic acid anhydride examples include methanesulfonic acid anhydride, ethanesulfonic acid anhydride, propanesulfonic acid anhydride, butanesulfonic acid anhydride, pentanesulfonic acid anhydride, hexanesulfonic acid anhydride, vinylsulfonic acid anhydride.
  • Benzenesulfonic acid anhydride trifluoromethanesulfonic acid anhydride, 2,2,2-trifluoroethanesulfonic acid anhydride, Pentafluoroethanesulfonic anhydride, 1,2-ethanedisulfonic anhydride, 1,3-propanedisulfonic anhydride, 1,4-butanedisulfonic anhydride, 1,2-benzenedisulfonic anhydride, tetrafluoro -1,2-ethanedisulfonic anhydride, hexafluoro-1,3-propanedisulfonic anhydride, octafluoro-1,4-butanedisulfonic anhydride, 3-fluoro-1,2-benzenedisulfonic anhydride 4-fluoro-1,2-benzenedisulfonic anhydride 3,4,5,6-tetrafluoro-1,2-benzenedisulfonic anhydride and the like. These may be used alone or
  • carboxylic acid and sulfonic acid anhydrides include acetic acid methanesulfonic acid anhydride, ethane sulfonic acid anhydride, acetic acid propane sulfonic acid anhydride, propionic acid methanesulfonic acid anhydride, propionic acid ethanesulfonic acid anhydride , Propionic acid propanesulfonic acid anhydride, trifluoroacetic acid methanesulfonic acid anhydride, trifluoroacetic acid ethanesulfonic acid anhydride, trifluoroacetic acid propanesulfonic acid anhydride, acetic acid trifluoromethanesulfonic acid anhydride, acetic acid 2,2,2 -Trifluoroethanesulfonic anhydride, pentafluoroethanesulfonic acid anhydride, trifluoromethanesulfonic anhydride, trifluoroacetic acid 2,2,2-trifluor
  • R 11 represents a substituted or unsubstituted alkylene group having 2 to 5 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 5 carbon atoms, a substituted or unsubstituted carbon group having 5 to 12 carbon atoms, and A cycloalkanediyl group, a substituted or unsubstituted benzenediyl group, or a divalent group having 2 to 6 carbon atoms to which an alkylene group is bonded via an ether bond).
  • R 103 represents a single bond, a double bond, a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 3 carbon atoms, an oxygen atom, or A divalent group having 2 to 4 carbon atoms to which an alkylene group is bonded via an ether bond).
  • the alkylene group and alkenylene group of R 11 and R 103 may be linear or branched.
  • the number of carbon atoms of the alkylene group represented by R 11 is preferably 1, 2, 3 or 4.
  • the carbon number of the alkenylene group of R 11 is preferably 2, 3 or 4.
  • the number of carbon atoms of the cycloalkanediyl group represented by R 11 is preferably 5, 6, 7, 8, 9, or 10.
  • R 11 is preferably a substituted or unsubstituted alkylene group having 2 to 5 carbon atoms or a substituted or unsubstituted alkenylene group having 2 to 5 carbon atoms.
  • the substituent of R 11 or R 103 is, for example, an alkyl group having 1 to 5 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group), carbon C2-C6 alkenyl group (for example, vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group), C1-C5 alkoxy group (for example, methoxy group, ethoxy group, n-propoxy group) , Iso-propoxy group, n-butoxy group, tert-butoxy group), amino group (including dimethylamino group and methylamino group), carboxy group, hydroxy group, vinyl group, cyano group, or halogen atom (for example, chlorine Atom, bromine atom).
  • R 11 or R 103 may have one substituent or a plurality of substituents.
  • R 103 is a single bond or a double bond
  • a single bond or a double bond is formed between carbon atoms adjacent to R 103 .
  • R 103 is preferably a single bond, a double bond, a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms, or a substituted or unsubstituted alkenylene group having 2 to 5 carbon atoms.
  • cyclic carboxylic acid anhydride represented by the formula (I) include the following compounds.
  • R 101 and R 102 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted group, A heterocyclic group having 4 to 12 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms.
  • the number of carbon atoms of the alkyl group is preferably 1, 2, 3, 4 or 5, and more preferably 1, 2, 3 or 4.
  • the aryl group preferably has 6, 7, 8, 9, or 10 carbon atoms.
  • the number of carbon atoms of the heterocyclic group is preferably 4, 5, 6, 7, 8, 9 or 10, and more preferably 4, 5, 6, 7 or 8.
  • the number of carbon atoms in the alkenyl group is preferably 2, 3, 4 or 5, and more preferably 2, 3 or 4.
  • the alkyl group or alkenyl group may be linear or branched.
  • R 101 and R 102 examples include an alkyl group having 1 to 5 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group), and a cycloalkyl group having 3 to 6 carbon atoms (for example, Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group), alkenyl group having 2 to 6 carbon atoms (for example, vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group), 1 to 5 carbon atoms Alkoxy groups (for example, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, tert-butoxy group), alkylcarbonyl group having 2 to 6 carbon atoms, aryl having 7 to 11 carbon atoms Carbonyl group, alkoxycarbonyl group, alk
  • An acid anhydride can be used alone or in combination of two or more.
  • R 101 and R 102 are preferably each independently an alkyl group having 1 to 5 carbon atoms.
  • the alkyl group may be linear or branched.
  • the alkyl group preferably has 1, 2, 3 or 4 carbon atoms.
  • chain carboxylic acid anhydride represented by the formula (III) include the following compounds.
  • succinic anhydride and maleic anhydride are preferable.
  • chain carboxylic acid anhydride acetic anhydride, propionic anhydride, and butyric anhydride are preferable.
  • the content of the acid anhydride in the electrolytic solution is not particularly limited, but is preferably 0.005 to 10% by mass. When the content of the acid anhydride is 0.005% by mass, a synergistic effect between the chain disulfone compound and the acid anhydride can be effectively obtained. Moreover, when content of an acid anhydride is 10 mass% or less, it can suppress that the membrane
  • the content of the acid anhydride in the electrolytic solution is more preferably 0.01% by mass or more, further preferably 0.1% by mass or more, and particularly preferably 0.5% by mass or more. . The content of the acid anhydride in the electrolytic solution is more preferably 8% by mass or less, further preferably 5% by mass or less, and particularly preferably 3% by mass or less.
  • the molar ratio B / A between the concentration A of the chain disulfone compound in the electrolyte and the concentration B of the acid anhydride in the electrolyte is preferably in the range of 1/10 to 5/1. More preferably, it is in the range of 1/9 to 4/1.
  • the total content C of the concentration A of the chain disulfone compound in the electrolytic solution and the concentration B of the acid anhydride electrolytic solution is preferably in the range of 1.0 mol / L or less, and is preferably 0.75 mol / L. More preferably, it is in the following range, and further preferably in the range of 0.5 mol / L or less.
  • the electrolyte solution may contain other additives other than the chain disulfone compound and the acid anhydride, if necessary.
  • additives include an overcharge inhibitor and a surfactant.
  • the non-aqueous solvent is not particularly limited, and examples thereof include carbonates such as cyclic carbonates and chain carbonates, aliphatic carboxylic acid esters, ⁇ -lactones, cyclic ethers, and chain ethers. And fluorine derivatives thereof. These can be used individually by 1 type or in combination of 2 or more types.
  • cyclic carbonates examples include propylene carbonate (PC), ethylene carbonate (EC), butylene carbonate (BC), and vinylene carbonate (VC).
  • chain carbonates examples include dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC), and dipropyl carbonate (DPC).
  • DMC dimethyl carbonate
  • DEC diethyl carbonate
  • EMC ethyl methyl carbonate
  • DPC dipropyl carbonate
  • Examples of the aliphatic carboxylic acid esters include methyl formate, methyl acetate, and ethyl propionate.
  • Examples of ⁇ -lactones include ⁇ -butyrolactone.
  • Examples of cyclic ethers include tetrahydrofuran and 2-methyltetrahydrofuran.
  • chain ethers examples include 1,2-diethoxyethane (DEE), ethoxymethoxyethane (EME), and the like.
  • non-aqueous solvents include, for example, dimethyl sulfoxide, 1,3-dioxolane, formamide, acetamide, dimethylformamide, acetonitrile, propylnitrile, nitromethane, ethyl monoglyme, phosphoric acid triester, trimethoxymethane, dioxolane derivatives , Sulfolane, methylsulfolane, 1,3-dimethyl-2-imidazolidinone, 3-methyl-2-oxazolidinone, propylene carbonate derivative, tetrahydrofuran derivative, ethyl ether, N-methylpyrrolidone, fluorinated carboxylic acid ester, methyl-2 , 2,2-trifluoroethyl carbonate, methyl-2,2,3,3,3-pentafluoropropyl carbonate, trifluoromethyl ethylene carbonate, monofluoromethyl ethyl Emissions carbonate, difluoromethyl
  • the non-aqueous solvent preferably contains carbonates.
  • the carbonates include cyclic carbonates or chain carbonates. Since carbonates have a large relative dielectric constant, the ion dissociation property of the electrolytic solution is improved, and further, the viscosity of the electrolytic solution is lowered, so that the ion mobility is improved.
  • carbonates having a carbonate structure are used as the non-aqueous solvent for the electrolytic solution, the carbonates tend to decompose and generate gas containing CO 2 .
  • the problem of blistering appears prominently and tends to lead to performance degradation.
  • the electrolytic solution preferably contains carbonates as a non-aqueous solvent in addition to the chain disulfone compound and the acid anhydride.
  • the content of carbonates in the electrolytic solution is, for example, 30% by mass or more, preferably 50% by mass or more, and more preferably 70% by mass or more.
  • the supporting salt is not particularly limited, for example, LiPF 6, LiAsF 6, LiAlCl 4, LiClO 4, LiBF 4, LiSbF 6, LiCF 3 SO 3, LiC 4 F 9 SO 3, Li (CF 3 And lithium salts such as SO 2 ) 2 and LiN (CF 3 SO 2 ) 2 .
  • a supporting salt can be used individually by 1 type or in combination of 2 or more types.
  • the concentration of the supporting salt in the electrolytic solution is preferably 0.5 to 1.5 mol / l. By setting the concentration of the supporting salt within this range, it becomes easy to adjust the density, viscosity, electrical conductivity, and the like to an appropriate range.
  • the secondary battery of the present embodiment includes a negative electrode having a negative electrode active material.
  • the negative electrode active material can be bound on the negative electrode current collector by a negative electrode binder.
  • a negative electrode active material layer including a negative electrode active material and a negative electrode binder is formed on a negative electrode current collector can be used.
  • a negative electrode active material can be used individually by 1 type or in combination of 2 or more types.
  • Examples of the metal (a) include Al, Si, Pb, Sn, In, Bi, Ag, Ba, Ca, Hg, Pd, Pt, Te, Zn, La, or alloys of two or more thereof. It is done. Two or more of these metals or alloys may be used in combination. These metals or alloys may contain one or more non-metallic elements. Among these, it is preferable to use silicon, tin, or an alloy thereof as the negative electrode active material. By using silicon or tin as the negative electrode active material, a lithium secondary battery excellent in weight energy density and volume energy density can be provided.
  • the metal oxide (b) examples include silicon oxide, aluminum oxide, tin oxide, indium oxide, zinc oxide, lithium oxide, and composites thereof. Among these, it is preferable to use silicon oxide as the negative electrode active material.
  • the metal oxide (b) can contain one or more elements selected from nitrogen, boron and sulfur in a range of, for example, 0.1 to 5% by mass.
  • Examples of the carbon material (c) include graphite, amorphous carbon, diamond-like carbon, carbon nanotube, or a composite thereof.
  • the negative electrode binder is not particularly limited, and examples thereof include polyvinylidene fluoride, vinylidene fluoride-hexafluoropropylene copolymer, vinylidene fluoride-tetrafluoroethylene copolymer, and styrene-butadiene copolymer rubber. , Polytetrafluoroethylene, polypropylene, polyethylene, polyimide, polyamideimide, polyacrylic acid and the like.
  • the negative electrode can be produced, for example, by forming a negative electrode active material layer containing a negative electrode active material and a negative electrode binder on a negative electrode current collector.
  • This negative electrode active material layer can be formed by a general slurry coating method.
  • a negative electrode can be obtained by preparing a slurry containing a negative electrode active material, a negative electrode binder, and a solvent, applying the slurry onto a negative electrode current collector, drying, and pressing as necessary. it can.
  • Examples of the method for applying the negative electrode slurry include a doctor blade method, a die coater method, and a dip coating method.
  • a negative electrode can also be obtained by forming a negative electrode active material layer in advance and then forming a thin film of copper, nickel or an alloy thereof as a current collector by a method such as vapor deposition or sputtering.
  • a water-dispersed polymer can be used as the negative electrode binder.
  • the negative electrode binder can be used in an aqueous dispersion state.
  • the water-dispersed polymer include styrene butadiene polymer, acrylic acid polymer, polytetrafluoroethylene, polyacrylate, and polyurethane. These polymers can be used by dispersing in water. More specifically, examples of the water-dispersed polymer include natural rubber (NR), styrene butadiene rubber (SBR), acrylonitrile / butadiene copolymer rubber (NBR), and methyl methacrylate / butadiene copolymer rubber (MBR).
  • NR natural rubber
  • SBR styrene butadiene rubber
  • NBR acrylonitrile / butadiene copolymer rubber
  • MRR methyl methacrylate / butadiene copolymer rubber
  • Chloroprene rubber (CR), acrylic rubber (ABR), styrene butadiene / styrene copolymer (SBS), butyl rubber (IIR), thiocol, urethane rubber, silicon rubber, or fluorine rubber. These can be used individually by 1 type or in combination of 2 or more types.
  • an aqueous dispersion polymer as a negative electrode binder, it is preferable to use an aqueous thickener.
  • the aqueous thickener include methyl cellulose, carboxymethyl cellulose (CMC), carboxymethyl cellulose sodium salt, carboxymethyl cellulose lithium salt, hydroxyethyl cellulose, polyethylene oxide, polyvinyl alcohol (PVA), polyvinyl pyrrolidone, sodium polyacrylate, polyacrylic acid. , Polyethylene glycol, or polyethylene oxide. These can be used individually by 1 type or in combination of 2 or more types.
  • the amount of the negative electrode binder is preferably 5 to 25 parts by mass with respect to 100 parts by mass of the negative electrode active material.
  • the content of the water-based thickener is, for example, 0.1 to 5.0 parts by weight, preferably 0.5 to 3.0 parts by weight with respect to 100 parts by weight of the negative electrode active material.
  • water is preferably used as the dispersion medium
  • a water-soluble solvent such as an alcohol solvent, an amine solvent, a carboxylic acid solvent, or a ketone solvent may be included as the dispersion medium.
  • the negative electrode can be produced, for example, as follows. First, a negative electrode active material, an aqueous thickener, an aqueous dispersion polymer, and water are kneaded to prepare a negative electrode slurry. Next, this aqueous slurry is applied to a negative electrode current collector, dried, and pressed to produce a negative electrode.
  • the amount of water contained in the negative electrode active material layer after producing the negative electrode is preferably 50 to 1000 ppm. Further, the amount of water contained in the negative electrode active material layer is more preferably 500 ppm or less.
  • the amount of water contained in the negative electrode active material layer can be controlled by, for example, a drying process after the negative electrode active material layer is formed.
  • the negative electrode current collector aluminum, nickel, stainless steel, chromium, copper, silver, and alloys thereof are preferable in view of electrochemical stability.
  • the shape include a foil, a flat plate, and a mesh.
  • the negative electrode active material layer may contain a conductive aid such as carbon from the viewpoint of improving conductivity.
  • the negative electrode slurry may contain other components as necessary, and examples of the other components include a surfactant and an antifoaming material.
  • the negative electrode slurry contains a surfactant, the dispersion stability of the negative electrode binder can be improved. Moreover, foaming at the time of apply
  • the secondary battery of this embodiment includes a positive electrode having a positive electrode active material.
  • the positive electrode active material can be bound on the positive electrode current collector by a positive electrode binder.
  • a positive electrode in which a positive electrode active material layer including a positive electrode active material and a positive electrode binder is formed on a positive electrode current collector can be used.
  • the positive electrode active material is not particularly limited, and examples thereof include lithium composite oxide and lithium iron phosphate. Further, at least part of the transition metal of these lithium composite oxides may be replaced with another element. Alternatively, a lithium composite oxide having a plateau at 4.2 V or more at the metal lithium counter electrode potential can be used. Examples of the lithium composite oxide include spinel type lithium manganese composite oxide, olivine type lithium containing composite oxide, and reverse spinel type lithium containing composite oxide.
  • lithium composite oxide examples include lithium manganate having a layered structure such as LiMnO 2 and Li x Mn 2 O 4 (0 ⁇ x ⁇ 2), lithium manganate having a spinel structure, or lithium manganate
  • a part of Mn is replaced with at least one element selected from the group consisting of Li, Mg, Al, Co, B, Ti and Zn
  • lithium cobaltate such as LiCoO 2 or part of Co of lithium cobaltate Is replaced with at least one element selected from the group consisting of Ni, Al, Mn, Mg, Zr, Ti, and Zn
  • lithium nickelate such as LiNiO 2 or a part of Ni in lithium nickelate is Co, Al Replaced with at least one element selected from the group consisting of Mn, Mg, Zr, Ti, Zn
  • LiN i 1/3 Co 1/3 Mn 1/3 O 2 or other specific transition metals such as lithium transition metal oxides, or some of the transition metals of the lithium transition metal oxides may be Co, Al, Mn And those substituted with at
  • lithium composite oxide a compound represented by the following formula is preferably exemplified.
  • x satisfies 0 ⁇ x ⁇ 2
  • a satisfies 0 ⁇ a ⁇ 1.2
  • M is at least one element selected from the group consisting of Ni, Co, Fe, Cr and Cu. .
  • an active material that operates at a potential of 4.5 V or higher with respect to lithium (hereinafter also referred to as a 5 V class active material) can be used from the viewpoint that a high voltage can be obtained.
  • a 5V class active material gas generation due to decomposition of the electrolytic solution or the like is likely to occur, but gas generation can be suppressed by using the electrolytic solution containing the compound of the present embodiment.
  • a lithium manganese composite oxide represented by the following formula (A) can be used as the 5V class active material.
  • M is Co, Ni, Fe, Cr.
  • Y is at least one selected from the group consisting of Li, B, Na, Mg, Al, Ti, Si, K and Ca, and Z is F and Cl. At least one selected from the group consisting of:
  • a spinel compound represented by the following formula (B) is preferably used among such metal complex oxides from the viewpoint of obtaining a sufficient capacity and extending the life.
  • A is at least one selected from the group consisting of Li, B, Na, Mg, Al, Ti and Si. is there.).
  • an olivine-type positive electrode active material As an active material that operates at a potential of 4.5 V or higher with respect to lithium, an olivine-type positive electrode active material can be given.
  • the olivine-type 5V active material include LiCoPO 4 and LiNiPO 4 .
  • Si composite oxide As an active material that operates at a potential of 4.5 V or more with respect to lithium, Si composite oxide can be given.
  • Si complex oxide the compound shown by a following formula (C) is mentioned, for example.
  • M is at least one selected from the group consisting of Mn, Fe and Co).
  • the active material that operates at a potential of 4.5 V or more with respect to lithium may have a layered structure.
  • a 5V class active material containing a layered structure the compound shown by following formula (D) is mentioned, for example.
  • M1 is at least one selected from the group consisting of Ni, Co, and Fe.
  • M2 is at least one selected from the group consisting of Li, Mg, and Al. 0.1 ⁇ x ⁇ 0.5, 0.05 ⁇ y ⁇ 0.3).
  • lithium metal composite oxides represented by the following (E) to (G) can be used.
  • M is at least one selected from the group consisting of Co and Ni).
  • M is composed of Li, Co, and Ni. At least one selected from the group).
  • the positive electrode can be manufactured as follows, for example. First, a positive electrode slurry containing a positive electrode active material, a positive electrode binder, and a solvent (and a conductive auxiliary material if necessary) is prepared. This positive electrode slurry is applied onto a positive electrode current collector, dried, and pressurized as necessary to form a positive electrode active material layer on the positive electrode current collector, thereby producing a positive electrode.
  • the positive electrode binder is not particularly limited, and for example, the same as the negative electrode binder can be used. From the viewpoint of versatility and low cost, polyvinylidene fluoride is preferred.
  • the content of the positive electrode binder is preferably in the range of 1 to 25 parts by mass with respect to 100 parts by mass of the positive electrode active material from the viewpoint of the binding force and energy density which are in a trade-off relationship. The range is more preferably in the range of 2 to 10 parts by mass.
  • binders other than polyvinylidene fluoride include, for example, vinylidene fluoride-hexafluoropropylene copolymer, vinylidene fluoride-tetrafluoroethylene copolymer, styrene-butadiene copolymer rubber, polytetrafluoroethylene, Examples include polypropylene, polyethylene, polyimide, or polyamideimide.
  • NMP N-methyl-2-pyrrolidone
  • the positive electrode current collector is not particularly limited, and examples thereof include aluminum, titanium, tantalum, nickel, silver, and alloys thereof.
  • Examples of the shape of the positive electrode current collector include a foil, a flat plate, and a mesh.
  • As the positive electrode current collector an aluminum foil can be suitably used.
  • a conductive auxiliary material may be added for the purpose of reducing the impedance.
  • the conductive auxiliary material include carbonaceous fine particles such as graphite, carbon black, and acetylene black.
  • the separator is not particularly limited.
  • a porous film such as polypropylene or polyethylene or a nonwoven fabric can be used.
  • the ceramic coat separator which formed the coating containing a ceramic in the polymer base material used as a separator can also be used.
  • stacked them can also be used as a separator.
  • Exterior Body is not particularly limited, and for example, a laminate film can be used.
  • a laminated film such as polypropylene or polyethylene coated with aluminum or silica can be used.
  • the distortion of the electrode laminate becomes very large when gas is generated, compared to a secondary battery using a metal can as the exterior body. This is because the laminate film is more easily deformed by the internal pressure of the secondary battery than the metal can. Furthermore, when sealing a secondary battery using a laminate film as an exterior body, the internal pressure of the battery is usually lower than the atmospheric pressure, so there is no extra space inside, and if gas is generated, it is immediately It tends to lead to battery volume change and electrode stack deformation.
  • the secondary battery according to the present embodiment can overcome such problems by using the electrolytic solution of the present embodiment.
  • the structure of the secondary battery according to the present embodiment is not particularly limited by the present invention.
  • an electrode laminate in which a positive electrode and a negative electrode are arranged to face each other and an electrolytic solution are provided.
  • the structure included in the exterior body can be given.
  • FIG. 1 is a schematic configuration diagram illustrating an example of a basic configuration of the secondary battery according to the present embodiment.
  • the positive electrode active material layer 1 is formed on the positive electrode current collector 3.
  • the negative electrode active material layer 2 is formed on the negative electrode current collector 4.
  • the positive electrode and the negative electrode are disposed to face each other with the separator 5 interposed therebetween.
  • the separator 5 is laminated and disposed substantially parallel to the positive electrode active material layer 1 and the negative electrode active material layer 2.
  • a pair of positive and negative electrodes and an electrolytic solution are enclosed in outer casings 6 and 7.
  • a positive electrode tab 9 connected to the positive electrode and a negative electrode tab 8 connected to the negative electrode are provided so as to be exposed from the exterior body.
  • the shape of the secondary battery according to the present embodiment is not particularly limited, and examples thereof include a laminate outer shape, a cylindrical shape, a square shape, a coin shape, and a button shape.
  • Example 1 ⁇ Negative electrode> Graphite was used as the negative electrode active material.
  • SBR the rubber particle dispersion (solid content 40 mass%) was used, and it measured and used so that the solid content of the binder might become the said mass ratio.
  • ⁇ Positive electrode> As the positive electrode active material, a mixture in which LiMn 2 O 4 and LiNi 0.5 Co 0.2 Mn 0.3 O 2 were mixed at a mass ratio of 25:75 was used. This positive electrode active material, carbon black as a conductive auxiliary material, and polyvinylidene fluoride as a positive electrode binder were weighed at a mass ratio of 90: 5: 5. These were mixed with N-methylpyrrolidone to prepare a positive electrode slurry. The positive electrode slurry was applied to an aluminum foil having a thickness of 20 ⁇ m, dried, and further pressed to produce a positive electrode.
  • Electrode laminate The obtained positive electrode and negative electrode were laminated via a polypropylene porous film as a separator. The ends of the positive electrode current collector not covered with the positive electrode active material and the negative electrode current collector not covered with the negative electrode active material were welded. Furthermore, the positive electrode terminal made from aluminum and the negative electrode terminal made from nickel were each welded to the welding location, and the electrode laminated body which has a planar laminated structure was obtained.
  • the above compound (201) as an acid anhydride is used as a supporting salt so that the content in the electrolytic solution is 0.5% by mass so that the content of 1 in the electrolytic solution is 1.7% by mass.
  • LiPF 6 was added to each of the mixed solvents so that the concentration in the electrolytic solution was 1 mol / L to prepare an electrolytic solution.
  • the electrode laminate was accommodated in an aluminum laminate film as an exterior body, and an electrolyte solution was injected into the exterior body. Thereafter, the outer package was sealed while reducing the pressure to 0.1 atm, and a lithium ion secondary battery was produced.
  • volume increase amount was calculated as a relative value as follows. First, “volume increase rate (%)” was calculated by ⁇ (volume after charge / discharge) / (volume before start of charge / discharge) ⁇ 1 ⁇ ⁇ 100 (unit:%). And the relative value when the volume increase rate in the comparative example 1 was set to 1 was calculated, and it was set as the volume increase amount. (Capacity maintenance rate at 45 ° C) Next, the manufactured secondary battery was subjected to a charge and discharge test in a voltage range of 3.0 V to 4.15 V in a thermostat kept at 45 ° C., and the capacity retention rate (%) was evaluated. As a standard for the current value, Ic was the current that used up the initial discharge amount of the battery in one hour. Charging was performed at a current value Ic up to 4.15 V, followed by constant voltage charging for 2.5 hours in total. The discharge was a constant current discharge to 3.0 V at a current value Ic.
  • Capacity maintenance ratio (%) was calculated by (discharge capacity after 200 cycles) / (discharge capacity after 5 cycles) ⁇ 100 (unit:%).
  • Example 2 A secondary battery was prepared and evaluated in the same manner as in Example 1 except that the compound (301) was used instead of the compound (201) as the acid anhydride. The results are shown in Table 1.
  • Example 3 A secondary battery was prepared and evaluated in the same manner as in Example 1 except that the compound (202) was used instead of the compound (201) as the acid anhydride. The results are shown in Table 1.
  • Example 4 As a chain disulfone compound, Compound No. In place of Compound No. 1 A secondary battery was prepared and evaluated in the same manner as in Example 1 except that 2. The results are shown in Table 1.
  • the secondary battery according to the embodiment of the present invention includes, for example, an electric vehicle, a plug-in hybrid vehicle, a driving device such as an electric motorcycle and an electric assist bicycle, tools such as an electric tool, an electronic device such as a portable terminal and a laptop computer,
  • the present invention can be applied to storage batteries for household power storage systems and solar power generation systems.

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Abstract

La présente invention concerne une solution électrolytique capable de supprimer la génération de gaz. Un mode de réalisation de la présente invention concerne une solution électrolytique contenant un sel de support, un solvant non aqueux qui dissout le sel de support, un composé de disulfone en chaîne représenté par la formule (1), et un anhydride d'acide. Ce mode de réalisation de la présente invention permet de fournir une solution électrolytique présentant un taux de rétention de capacitance excellent, et capable de supprimer la génération de gaz.
PCT/JP2014/071281 2013-09-13 2014-08-12 Solution électrolytique et batterie secondaire Ceased WO2015037382A1 (fr)

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CN106505249A (zh) * 2016-12-15 2017-03-15 东莞市杉杉电池材料有限公司 一种锂离子电池电解液及含该电解液的锂离子电池
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EP3444887A3 (fr) * 2017-08-16 2019-02-27 Samsung Electronics Co., Ltd. Additif à base de disulfonate et batterie secondaire au lithium le comprenant
CN109687021A (zh) * 2018-12-18 2019-04-26 东莞市杉杉电池材料有限公司 一种耐高温锂离子电池非水电解液
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WO2023068807A1 (fr) * 2021-10-19 2023-04-27 주식회사 엘지에너지솔루션 Batterie secondaire au lithium

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