# US 10,374,258 B2 · Cyclobutenedione derivative, nonaqueous electrolytic solution, and lithium ion secondary battery

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- Number: US 10,374,258 B2
- Document ID: US10374258B2
- Status: Granted
- Kind: B2
- Application number: 15/500,459
- Filed: 2015-07-01
- Published: 2017-07-27
- Granted: 2019-08-06
- Earliest claimed: 2014-07-31
- Assignees: NEC Corporation
- Applicants: NEC Corporation
- Inventors: Katsumi Maeda; Shizuka Sato; Mika Horie
- Web page: https://patentgrep.com/patent/US10374258B2

## CPC

- H01M 10/0567: characterised by the additives
- C07C 49/647: having unsaturation outside the ring
- C07C 49/683: having unsaturation outside the aromatic rings
- C07C 49/697: containing six-membered aromatic rings
- C07C 49/753: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07D 307/46: Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D 333/22: Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- C07F 7/0803: {Compounds with Si-C or Si-Si linkages}
- H01M 4/386: {Silicon or alloys based on silicon}
- H01M 4/483: {for non-aqueous cells (H01M4/485 takes precedence)}
- H01M 4/505: of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
- H01M 4/525: of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
- H01M 4/587: for inserting or intercalating light metals
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- C07C 2601/04: with a four-membered ring
- H01M 2300/0025: Organic electrolyte
- H01M 2300/0037: Mixture of solvents
- Y02E 60/10: Energy storage using batteries
- Y02T 10/70: Energy storage systems for electromobility, e.g. batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

A nonaqueous electrolytic solution comprising a cyclobutenedione derivative represented by the following general formula (1): wherein R1 represents an organic group having a carbon-carbon double bond or a carbon-carbon triple bond in its structure, and R2 represents an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, a thioalkyl group having 1-6 carbon atoms, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

## Claims

### Claim 1

A nonaqueous electrolytic solution comprising:
a nonaqueous solvent, an electrolyte salt, and a cyclobutenedione derivative represented by the following general formula (1):
wherein in the general formula (1), R1 is a group selected from the group consisting of a vinyl group, an allyl group, a 1-propenyl group, an isopropenyl group, an ethynyl group, a phenylethynyl group, and a trimethylsilylethynyl group, and
wherein in the general formula (1), R2 is a group selected from the group consisting of a phenyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, an isopropoxy group, a 4-fluorophenyl group, a 2,4-difluorophenyl group, a pentafluorophenyl group, a tolyl group, a 4-methylthiophenyl group, a 2-thienyl group, a 2-furanyl group, an alkylthio group having 1-3 carbon atoms, and a phenylthio group.

### Claim 2 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, wherein a content of the cyclobutenedione derivative is in a range of 0.01 to 10% by mass based on a total mass of the nonaqueous electrolytic solution.

### Claim 3 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, further comprising at least one additive compound selected from the group consisting of vinylene carbonate, fluoroethylene carbonate, 1,3-propanesultone, maleic anhydride, and 1,5,2,4-dioxadithiane-2,2,4,4-tetraoxide, wherein
a content of the additive compound is in a range of 0.01 to 10% by mass based on a total mass of the nonaqueous electrolytic solution.

### Claim 4 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, comprising a lithium salt as the electrolyte salt.

### Claim 5 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, comprising a carbonate as the nonaqueous solvent.

### Claim 6 (depends on 1)

The nonaqueous electrolytic solution according to claim 1,
wherein in the general formula (1), R1 is a group selected from the group consisting of the vinyl group, the allyl group, the ethynyl group and the trimethylsilylethynyl group, and
wherein in the general formula (1), R2 is a group selected from the group consisting of the phenyl group, the methyl group, the methoxy group, the isopropoxy group, the 4-fluorophenyl group, the 2,4-difluorophenyl group, the pentafluorophenyl group and the 2-thienyl group.

### Claim 7 (depends on 1)

The nonaqueous electrolytic solution according to claim 1,
wherein in the general formula (1), R1 is a group selected from the group consisting of the vinyl group, the allyl group and the ethynyl group, and
wherein in the general formula (1), R2 is a group selected from the group consisting of the phenyl group, the methyl group, the methoxy group, the isopropoxy group, the 4-fluorophenyl group, the 2,4-difluorophenyl group and the pentafluorophenyl group.

### Claim 8 (depends on 1)

A lithium ion secondary battery comprising: a positive electrode comprising a positive electrode active material capable of intercalating and deintercalating a lithium ion; a negative electrode comprising a negative electrode active material capable of intercalating and deintercalating a lithium ion; and the nonaqueous electrolytic solution according to claim 1.

### Claim 9 (depends on 8)

The lithium ion secondary battery according to claim 8, wherein the negative electrode active material comprises at least one selected from the group consisting of elementary silicon, a silicon oxide, and a carbonaceous material.