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EP-4738519-A1 - NONAQUEOUS ELECTROLYTE SOLUTION AND NONAQUEOUS ELECTROLYTE BATTERY

EP4738519A1EP 4738519 A1EP4738519 A1EP 4738519A1EP-4738519-A1

Abstract

A nonaqueous electrolyte solution containing (I) a compound represented by the general formula (1) described in the specification, (II) at least one compound selected from the group consisting of the compounds (2) to (5) described in the specification, (III) a solute, and (IV) a nonaqueous organic solvent, and a nonaqueous electrolyte solution battery containing the nonaqueous electrolyte solution.

Inventors

  • ESAKI, Ryota
  • TERADA, RYOSUKE
  • 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) a compound represented by the following general formula (1); (II) at least one compound selected from the group consisting of the following compounds (2) to (5); (III) a solute; and (IV) a nonaqueous organic solvent: wherein in the general formula (1), R 1 represents an alkylene group having 1 to 6 carbon atoms, an oxygen atom may be included in a carbon atom-carbon atom bond in the alkylene group, and any hydrogen atom of the alkylene group may be substituted with a halogen atom, a compound (2): at least one compound selected from the group consisting of a compound represented by the following general formula (2-A), a compound represented by the following general formula (2-B), and a compound represented by the following general formula (2-C), wherein in the general formula (2-A), R 21 and R 22 each independently represent a fluorine atom or an organic group selected from the group consisting of an 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, any hydrogen atom of the organic group may be substituted with a fluorine atom, and an oxygen atom may be included in a carbon atom-carbon atom bond in the organic group, M 1 m+ is a proton, a metal cation, or an onium cation, and m represents a valence of the corresponding cation, wherein the compound represented by the general formula (2-A) contains at least one P-F bond, in the general formula (2-B), X 21 represents a fluorine atom or an organic group selected from the group consisting of an 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, an 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, any hydrogen atom of the organic group may be substituted with a fluorine atom, an oxygen atom may be included in a carbon atom-carbon atom bond in the organic group, and the organic group contains at least one fluorine atom, M 1 m+ is a proton, a metal cation, or an onium cation, and m represents a valence of the corresponding cation, in the general formula (2-C), X 22 to X 25 each independently represent a fluorine atom or an organic group selected from the group consisting of an 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, an 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, any hydrogen atom of the organic group may be substituted with a fluorine atom, an oxygen atom may be included in a carbon atom-carbon atom bond in the organic group, and the organic group contains at least one fluorine atom, M 1 m+ is a proton, a metal cation, or an onium cation, and m represents a valence of the corresponding cation, wherein the compound represented by the general formula (2-C) contains at least one B-F bond, a compound (3): a compound represented by the following general formula (3), wherein in the general formula (3), each R 31 represents a group having a carbon-carbon unsaturated bond, the plurality of R 31 's may be the same as or different from each other, each R 32 represents a fluorine atom or an alkyl group having 1 to 10 carbon atoms, the alkyl group may have at least one of a fluorine atom or an oxygen atom, when there are a plurality of R 32 's, the plurality of R 32 's may be the same as or different from each other, and v represents an integer of 2 to 4, a compound (4): a compound represented by the following general formula (4), wherein in the general formula (4), R 41 and R 42 each independently represent a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an aryl group having 6 to 10 carbon atoms, any hydrogen atom of the alkenyl group and the aryl group may be substituted with a halogen atom, and n4 is 0 or 1, a compound (5): a compound represented by the following general formula (5), wherein in the general formula (5), R 50 to R 53 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 n51 represents an integer of 1 to 3.
  2. The nonaqueous electrolyte solution according to claim 1, wherein a content of the (I) with respect to the total amount of the nonaqueous electrolyte solution is 0.01% by mass or more and 10% by mass or less.
  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 or more and 10% by mass or less.
  4. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the compound represented by the general formula (1) is at least one compound selected from the group consisting of 1,2-ethanedisulfonic anhydride and 1,3-propanedisulfonic anhydride.
  5. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the compound (2) is at least one compound selected from the group consisting of lithium difluorophosphate, lithium fluorosulfonate, lithium trifluoromethanesulfonate, and lithium tetrafluoroborate.
  6. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the compound (3) is at least one compound selected from the group consisting of trivinylmethylsilane, trivinylfluorosilane, and tetravinylsilane.
  7. The nonaqueous electrolyte solution according to claim 1 or 2, wherein the compound (4) 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.
  8. 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 , LiN(CF 3 SO 2 ) 2 , LiN(FSO 2 ) 2 , LiN(POF 2 ) 2 , LiCF 3 SO 3 , LiC 4 F 9 SO 3 , LiAlO 2 , LiAlCl 4 , LiCl, and LiI; or at least one selected from the group consisting of NaPF 6 , NaSbF 6 , NaAsF 6 , NaClO 4 , NaN(CF 3 SO 2 ) 2 , NaN(FSO 2 ) 2 , NaN(POF 2 ) 2 , NaCF 3 SO 3 , NaC 4 F 9 SO 3 , NaAlO 2 , NaAlCl 4 , NaCl, and NaI.
  9. 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.
  10. The nonaqueous electrolyte solution according to claim 9, wherein the cyclic ester is a cyclic carbonate.
  11. The nonaqueous electrolyte solution according to claim 10, wherein the cyclic carbonate is at least one selected from the group consisting of ethylene carbonate, propylene carbonate, and fluoroethylene carbonate.
  12. The nonaqueous electrolyte solution according to claim 9, wherein the chain ester is a chain carbonate.
  13. The nonaqueous electrolyte solution according to claim 12, wherein 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 disclosure relates to a nonaqueous electrolyte solution and a nonaqueous electrolyte solution battery. BACKGROUND ART In recent years, there is a rapidly increasing demand for batteries that have a high capacity, high output, and a high energy density and that can be mounted as an auxiliary power source for electric vehicles, hybrid vehicles, and fuel-cell vehicles in addition to a power storage system for a compact and high energy density application, such as information-related devices and communication devices, that is, personal computers, video cameras, digital cameras, mobile phones, and smartphones. In addition, there is an increasing demand for batteries that can be used for a long period of time even in power storage systems for large and power applications such as power storage. Nonaqueous electrolyte solution batteries such as lithium secondary batteries have been actively developed as candidates for these various power storage systems. A nonaqueous electrolyte solution battery generally includes a positive electrode, a negative electrode, a separator, and a nonaqueous electrolyte solution. Patent Literature 1 proposes to improve the charge-discharge efficiency and the cycle characteristic using a sulfonic anhydride in an electrolyte solution. Patent Literature 2 proposes to improve the cycle characteristic and the low-temperature characteristic using a silicon compound in an electrolyte solution. Patent Literature 3 proposes to improve the storage characteristic using a nonaqueous electrolyte solution containing lithium bis(fluorosulfonyl)imide as a solute. Patent Literature 4 proposes to suppress self-discharge and improve the storage characteristic after charging 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 using a nonaqueous electrolyte solution containing a fluorosulfonic acid salt. Patent Literature 6 proposes to suppress the decomposition on the carbon negative electrode due to the progress of the charge and discharge cycle using a nonaqueous electrolyte solution containing a cyclic sulfate ester. CITATION LIST PATENT LITERATURE Patent Literature 1: JP4379567BPatent Literature 2: JP3497812BPatent Literature 3: JP4847675BPatent Literature 4: JP3439085BPatent Literature 5: JP5353923BPatent Literature 6: JP3760540B SUMMARY OF INVENTION TECHNICAL PROBLEM As described above, Patent Literature 1 proposes to improve the charge-discharge efficiency and the cycle characteristic of a secondary battery using an electrolyte solution containing a sulfonic anhydride. However, the studies by the present disclosers have revealed that the secondary battery described in Patent Literature 1 has a problem of high initial resistance. The present disclosure has been made in view of the above circumstances, and an object thereof is to provide a nonaqueous electrolyte solution capable of lowering the initial resistance of a nonaqueous electrolyte solution battery and a nonaqueous electrolyte solution battery having low initial resistance. SOLUTION TO PROBLEM As a result of intensive studies to solve such a problem, the present disclosers have found that a nonaqueous electrolyte solution battery having low initial resistance can be provided when a specific sulfonic anhydride and a specific compound are contained in a nonaqueous electrolyte solution containing a nonaqueous organic solvent and a solute. Specifically, the above problem can be solved by the following configuration. [1] A nonaqueous electrolyte solution containing: (I) a compound represented by the following general formula (1);(II) at least one compound selected from the group consisting of the following compounds (2) to (5);(III) a solute; and(IV) a nonaqueous organic solvent. In the general formula (1), R1 represents an alkylene group having 1 to 6 carbon atoms. An oxygen atom may be included in a carbon atom-carbon atom bond in the alkylene group. Any hydrogen atom of the alkylene group may be substituted with a halogen atom. A compound (2): at least one compound selected from the group consisting of a compound represented by the following general formula (2-A), a compound represented by the following general formula (2-B), and a compound represented by the following general formula (2-C). In the general formula (2-A), R21 and R22 each independently represent a fluorine atom or an organic group selected from the group consisting of an 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. Any hydrogen atom of the organic group may be substituted with a fluorine atom. An oxygen atom may be included in a carbon