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EP-4738518-A1 - NONAQUEOUS ELECTROLYTE SOLUTION AND NONAQUEOUS ELECTROLYTE BATTERY USING SAME

EP4738518A1EP 4738518 A1EP4738518 A1EP 4738518A1EP-4738518-A1

Abstract

The present disclosure provides a nonaqueous electrolyte solution containing (I) at least one sulfonic anhydride "1" represented by the general formula (1) described in the specification, (11) at least one compound selected from the group consisting of "2", "3", "4", "5", "6", and "7" described in the specification, (III) a solute, and (IV) a nonaqueous organic solvent and a nonaqueous electrolyte solution battery including at least a positive electrode, a negative electrode, a separator, and the nonaqueous electrolyte solution.

Inventors

  • ESAKI, Ryota
  • YAMAGUCHI, YUKIHIRO
  • TOKOMOTO, Junichi
  • KAWABATA, Wataru
  • TAKAHASHI, MIKIHIRO

Assignees

  • Central Glass Company, Limited

Dates

Publication Date
20260506
Application Date
20240726

Claims (14)

  1. A nonaqueous electrolyte solution, comprising: (I) at least one sulfonic anhydride "1" represented by the following general formula (1); (II) at least one compound selected from the group consisting of "2", "3", "4", "5", "6", and "7" below; (III) a solute; and (IV) a nonaqueous organic solvent: wherein in the general formula (1), R 1 and R 2 each independently represent a linear or branched-chain alkyl group having 1 to 6 carbon atoms, a linear or branched-chain alkenyl group having 2 to 10 carbon atoms, or an aryl group which may be substituted with an alkyl group having 6 to 10 carbon atoms, and any hydrogen atom of the alkyl group, the alkenyl group, and the aryl group represented by R 1 and R 2 may be substituted with a halogen atom; the "2" is at least one compound selected from the group consisting of compounds represented by the following general formula (2-1) and general formula (2-2), wherein in the general formula (2-1), R 3 and R 4 are each independently a fluorine atom or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, a fluorine atom, an oxygen atom, and/or an unsaturated bond may be present in the organic group, and the general formula (2-1) includes at least one P-F bond, in the general formula (2-2), X 1 is a fluorine atom or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, the organic group may contain at least one fluorine atom, and an oxygen atom and/or an unsaturated bond may be present in the organic group, and in the general formula (2-1) and the general formula (2-2), M 1 m+ is a proton, a metal cation, or an onium cation, and m represents a valence of a corresponding cation; the "3" is at least one compound selected from the group consisting of compounds represented by the following general formula (3-1) to general formula (3-3), wherein in the general formula (3-1) to the general formula (3-3), R 5 to R 10 are each independently a fluorine atom or an organic group selected from the group consisting of a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and a fluorine atom, an oxygen atom, and/or an unsaturated bond may be present in the organic group, X 2 to X 4 are each independently a fluorine atom or an organic group selected from the group consisting of a linear or branched alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and a fluorine atom, an oxygen atom, and/or an unsaturated bond may be present in the organic group, the general formulae (3-1) to (3-3) include at least one P-F bond and/or S-F bond, and M 1 m+ is a proton, a metal cation, or an onium cation, and m represents a valence of a corresponding cation; the "4" is at least one compound selected from the group consisting of a compound represented by the following general formula (4-1) and a compound represented by the following general formula (4-2), wherein in the general formula (4-1), W represents a boron atom, a phosphorus atom, or a silicon atom, nl is 0 to 3, n2 is 0 to 4, p is 0 or 1, R 41 represents an alkylene group having 1 to 10 carbon atoms, a halogenated alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a halogenated arylene group having 6 to 20 carbon atoms (wherein the groups may contain a substituent or may contain a heteroatom in the structures thereof, and when n1 is 2 or more, the n1 R 41 's may be bonded to each other), R 42 represents a halogen atom, Y 1 and Y 2 each independently represent an oxygen atom or a sulfur atom, and Y 3 represents a carbon atom or a sulfur atom, q is 1 when Y 3 is a carbon atom, and q is 1 or 2 when Y 3 is a sulfur atom, M a+ represents an alkali metal cation, an alkaline earth metal cation, or an onium cation, a represents a valence of a corresponding cation, and a to d are each 1 or 2 and satisfy a × b = c × d, wherein in the general formula (4-2), R 43 represents an alkylene group having 1 to 10 carbon atoms, a halogenated alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a halogenated arylene group having 6 to 20 carbon atoms (wherein the groups may contain a substituent or may contain a heteroatom in the structures thereof), r is 0 or 1, Y 4 represents a carbon atom or a sulfur atom, s is 1 when Y 4 is a carbon atom, and s is 1 or 2 when Y 4 is a sulfur atom, W 2 represents a boron atom or a phosphorus atom, R 44 represents a halogen atom, and n3 is 2 when W 2 is a boron atom, and n3 is 4 when W 2 is a phosphorus atom; the "5" is at least one compound represented by the following general formula (5), [Chem. 6] S i (R 51 ) v (R 52 ) 4-v (5) wherein in the general formula (5), R 51 's each independently represent a group having a carbon-carbon unsaturated bond, when there are a plurality of R 52 's, R 52 's each independently represent a fluorine atom or a linear or branched alkyl group having 1 to 10 carbon atoms, the alkyl group may have at least one of a fluorine atom or an oxygen atom, and v represents an integer of 2 to 4; the "6" is at least one compound represented by the following general formula (6), wherein in the general formula (6), R 61 and R 62 each independently represent a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, a linear or branched-chain alkenyl group having 2 to 5 carbon atoms, or an aryl group which may be substituted with an alkyl group having 6 to 10 carbon atoms, and any hydrogen atom of the alkyl group, the alkenyl group, and the aryl group represented by R 61 and R 62 may be substituted with a halogen atom, and n6 is 0 or 1; and the "7" is at least one compound selected from the group consisting of compounds represented by the following general formula (7-1) and general formula (7-2), wherein in the general formula (7-1), R 70 to R 73 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having 1 to 5 carbon atoms, or a fluoroalkyl group having 1 to 4 carbon atoms, and n71 represents an integer of 1 to 3, and in the general formula (7-2), R 74 to R 79 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a fluoroalkyl group having 1 to 4 carbon atoms, and n72 represents an integer of 0 to 2.
  2. The nonaqueous electrolyte solution according to claim 1, wherein a content of the (I) with respect to a total amount of the nonaqueous electrolyte solution is 0.01% by mass to 10% by mass.
  3. The nonaqueous electrolyte solution according to claim 1 or 2, wherein a content of the (II) with respect to the total amount of the nonaqueous electrolyte solution is 0.01% by mass to 10% by mass.
  4. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the (I) is at least one selected from the group consisting of methanesulfonic anhydride and ethanesulfonic anhydride.
  5. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the "2" is at least one compound selected from the group consisting of lithium difluorophosphate, lithium fluorosulfonate, and lithium trifluoromethanesulfonate.
  6. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the "3" is at least one compound selected from the group consisting of lithium bis(fluorosulfonyl)imide, lithium (fluorosulfonyl)(difluorophosphoryl)imide, lithium bis(trifluoromethanesulfonyl)imide, lithium bis(difluorophosphoryl)imide, lithium bis(pentafluoroethanesulfonyl)imide, and lithium (fluorosulfonyl)(trifluoromethanesulfonyl)imide.
  7. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the "4" is at least one compound selected from the group consisting of lithium tetrafluoroborate, lithium bis(oxalato)borate, lithium difluoro(oxalato)borate, lithium tris(oxalato)phosphate, lithium difluorobis(oxalato)phosphate, lithium tetrafluoro(oxalato)phosphate, lithium difluoro(malonato)borate, lithium tetrafluoro(malonato)phosphate, a tetrafluoro(picolinato)phosphate, and a difluoro(picolinato)borate.
  8. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the "5" is at least one compound selected from the group consisting of trivinylmethylsilane, trivinylfluorosilane, and tetravinylsilane.
  9. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the "6" is at least one compound selected from the group consisting of 1,3,2-dioxathiolane-2,2-dioxide and 1,3,2-dioxathiane-2,2-dioxide.
  10. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the (III) is at least one selected from the group consisting of LiPF 6 , LiSbF 6 , LiAsF 6 , LiClO 4 , LiAlO 2 , LiAlCl a , LiCl, and LiI or at least one selected from the group consisting of NaPF 6 , NaSbF 6 , NaAsF 6 , NaClO 4 , NaAlO 2 , NaAlCl 4 , NaCl, and NaI.
  11. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the (IV) contains at least one selected from the group consisting of a cyclic ester, a chain ester, a cyclic ether, a chain ether, a sulfone compound, a sulfoxide compound, and an ionic liquid.
  12. The nonaqueous electrolyte solution according to claim 11, wherein the cyclic ester is a cyclic carbonate, and the cyclic carbonate is at least one selected from the group consisting of ethylene carbonate, propylene carbonate, and fluoroethylene carbonate.
  13. The nonaqueous electrolyte solution according to claim 11, wherein the chain ester is a chain carbonate, and the chain carbonate is at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate.
  14. A nonaqueous electrolyte solution battery, at least comprising: a positive electrode; a negative electrode; a separator; and the nonaqueous electrolyte solution according to claim 1 or 2.

Description

TECHNICAL FIELD The present invention relates to a nonaqueous electrolyte solution and a nonaqueous electrolyte solution battery using the same. BACKGROUND ART As measures for improving the durability such as cycle characteristics and high-temperature storage characteristics of a nonaqueous electrolyte solution battery, optimization of various constituting elements of the battery including active materials of a positive electrode and a negative electrode has been hitherto studied. Techniques relating to a nonaqueous electrolyte solution have also been studied, and use of a variety of additives to prevent deterioration of a nonaqueous electrolyte solution at surfaces of active positive and negative electrodes due to decomposition of the nonaqueous electrolyte solution has been proposed. For example, Patent Literature 1 proposes to improve the cycle characteristic by using a sulfonic anhydride in an electrolyte solution. Patent Literature 2 proposes to improve the cycle characteristic and the low-temperature characteristic by using a silicon compound in an electrolyte solution. Patent Literature 3 proposes to improve the storage characteristic by using a nonaqueous electrolyte solution containing lithium bis(fluorosulfonyl)imide as a solute. Patent Literature 4 proposes to improve the storage characteristic after charging by using lithium monofluorophosphate or lithium difluorophosphate in an electrolyte solution. Patent Literature 5 proposes to maintain a high input/output characteristic and an impedance characteristic even after a durability test by using a nonaqueous electrolyte solution characterized by containing a fluorosulfonic acid salt. Patent Literature 6 proposes that the decomposition on the carbon negative electrode due to the progress of the charge and discharge cycle can be suppressed by using a nonaqueous electrolyte solution characterized by containing a cyclic sulfate ester. Patent Literature 7 proposes that a battery in which deterioration of the load characteristic and the resistance is significantly suppressed and in which the gas generation amount in the battery is low can be obtained by using a nonaqueous electrolyte solution characterized by containing a cyclic sultone (unsaturated sultone). Patent Literature 8 discloses an electrolyte which contains various oxalato salts and malonato salts and which has high heat resistance and hydrolysis resistance. Moreover, Patent Literature 9 discloses that a nonaqueous electrolyte solution battery having high-temperature durability is obtained by adding a picolinic acid derivative represented by the general formula (3) in the literature to a nonaqueous electrolyte solution. CITATION LIST PATENT LITERATURE Patent Literature 1: JP3760539BPatent Literature 2: JP3497812BPatent Literature 3: JP4847675BPatent Literature 4: JP3439085BPatent Literature 5: JP5353923BPatent Literature 6: JP3760540BPatent Literature 7: JP4190162BPatent Literature 8: JP3722685BPatent Literature 9: WO-A1-2016/002774 SUMMARY OF INVENTION TECHNICAL PROBLEM However, as a result of studies by the present disclosers, it has been found that although the battery characteristics are certainly improved in the batteries disclosed in the related art documents, there is room for improvement regarding the initial resistance. The present disclosure has been made in view of the above circumstances, and an object of the present disclosure is to provide a nonaqueous electrolyte solution and a nonaqueous electrolyte solution battery, each of which can reduce the initial resistance value of a battery. SOLUTION TO PROBLEM As a result of intensive studies to solve such a problem, the present inventors have found that by adding a specific sulfonic anhydride and at least one selected from the group consisting of a phosphate, a sulfonate, an imide salt, a borate, a picolinic acid derivative, a silicon compound, a cyclic sulfate ester, and a cyclic sultone, each having specific structures to a nonaqueous electrolyte solution for a nonaqueous electrolyte solution battery containing a nonaqueous solvent and a solute, an initial resistance value of the battery can be reduced when the electrolyte solution is used in a nonaqueous electrolyte solution battery, and the present invention has been thus completed. That is, the present invention is as follows. [1] A nonaqueous electrolyte solution, containing: (I) at least one sulfonic anhydride "1" represented by the following general formula (1);(II) at least one compound selected from the group consisting of "2", "3", "4", "5", "6", and "7" below;(III) a solute; and(IV) a nonaqueous organic solvent. In the general formula (1), R1 and R2 each independently represent a linear or branched-chain alkyl group having 1 to 6 carbon atoms, a linear or branched-chain alkenyl group having 2 to 10 carbon atoms, or an aryl group which may be substituted with an alkyl group having 6 to 10 carbon atoms. Any hydrogen atom of the alkyl group, the alkenyl group, and the aryl