# US 10,374,259 B2 · Hydrofluoroether compound, nonaqueous electrolyte solution and lithium ion secondary battery

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- Number: US 10,374,259 B2
- Document ID: US10374259B2
- Status: Granted
- Kind: B2
- Application number: 15/560,807
- Filed: 2016-03-02
- Published: 2018-04-26
- Granted: 2019-08-06
- Earliest claimed: 2015-03-25
- Assignees: NEC Corporation
- Applicants: NEC Corporation
- Inventors: Katsumi Maeda
- Web page: https://patentgrep.com/patent/US10374259B2

## CPC

- H01M 10/0569: characterised by the solvents
- C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C07C 43/126: {having more than one ether bond}
- H01M 4/131: Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx
- H01M 4/133: Electrodes based on carbonaceous material, e.g. graphite-intercalation compounds or CFx
- H01M 4/38: of elements or alloys
- H01M 4/48: of inorganic oxides or hydroxides
- 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 10/052: Li-accumulators
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/0567: characterised by the additives
- H01M 10/4235: {Safety or regulating additives or arrangements in electrodes, separators or electrolyte (H01M10/4242 takes precedence)}
- H01M 2300/0034: Fluorinated solvents
- H01M 2300/004: Three solvents
- Y02E 60/10: Energy storage using batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A nonaqueous electrolyte solution including a hydrofluoroether compound represented by the following formula (1): [Formula 1] CF3CF2CF2OCHFCF2OR1 (1) wherein R1 represents a difluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 1,1,1,3,3,3-hexafluoroisopropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a 2,2,3,3,4,4-hexafluorobutyl group, or a 2,2,3,3,4,4,5,5-octafluoropentyl group.

## Claims

### Claim 1

A nonaqueous electrolyte solution for a lithium ion secondary battery, comprising:
an electrolytic salt; and
a hydrofluoroether compound represented by the following formula (1):
[Formula 1]
CF3CF2CF2OCHFCF2OR1 (1)
wherein R1 represents a difluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 1,1,1,3,3,3-hexafluoroisopropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a 2,2,3,3,4,4-hexafluorobutyl group, or a 2,2,3,3,4,4,5,5-octafluoropentyl group.

### Claim 2 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, further comprising at least one of a chain carbonate and a cyclic carbonate.

### Claim 3 (depends on 2)

The nonaqueous electrolyte solution according to claim 2, wherein the chain carbonate is at least one compound selected from the group consisting of dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, dipropyl carbonate, dibutyl carbonate, methyl propyl carbonate, methyl isopropyl carbonate, methyl butyl carbonate, fluoromethyl methyl carbonate, 2-fluoroethyl methyl carbonate, ethyl-(2-fluoroethyl) carbonate, ethyl-(2,2-difluoroethyl) carbonate, bis(2-fluoroethyl) carbonate and ethyl-(2,2,2-trifluoroethyl) carbonate; and
the cyclic carbonate is at least one compound selected from the group consisting of ethylene carbonate, propylene carbonate, fluoroethylene carbonate, butyl ene carbonate, vinylene carbonate and vinyl ethylene carbonate.

### Claim 4 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, comprising a cyclic carbonate.

### Claim 5 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, further comprising at least one of a fluorine-containing ether represented by the following formula (2) and a fluorine-containing phosphate ester represented by the following formula (3):
[Formula 2]
R2—O—R3 (2)
wherein R2 and R3 are each independently an alkyl group or a fluorine-containing alkyl group, and at least one of R2 and R3 is a fluorine-containing alkyl group, and
wherein R4, R5 and R6 are each independently an alkyl group or a fluorine-containing alkyl group, and at least one of R4, R5 and R6 is a fluorine-containing alkyl group.

### Claim 6 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, wherein a content of the hydrofluoroether compound represented by the formula (1) is 1% by volume to 60% by volume with respect to the whole of nonaqueous solvents in the nonaqueous electrolyte solution.

### Claim 7 (depends on 1)

A lithium ion secondary battery, comprising a positive electrode containing a positive electrode active substance material capable of occluding and releasing lithium ions, a negative electrode containing a negative electrode active substance material capable of occluding and releasing lithium ions, and a nonaqueous electrolyte solution, wherein the nonaqueous electrolyte solution is the nonaqueous electrolyte solution according to claim 1.

### Claim 8 (depends on 7)

The lithium ion secondary battery according to claim 7, wherein the positive electrode active substance material comprises a lithium metal composite oxide.

### Claim 9 (depends on 7)

The lithium ion secondary battery according to claim 7, wherein the negative electrode active substance material comprises at least one of elemental silicon, silicon oxides and a carbonaceous material.

### Claim 10 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, wherein the electrolytic salt comprises a lithium salt.

### Claim 11 (depends on 1)

The nonaqueous electrolyte solution according to claim 1, wherein the electrolytic salt comprises at least one selected from the group consisting of LiPF6, LiBF4, LiN(SO2F)2, LiN(SO2CF3)2 and LiN(SO2C2F5)2.

### Claim 12

A hydrofluoroether compound, represented by the following formula (1):
[Formula 4]
CF3CF2CF2OCHFCF2OR1 (1)
wherein R1 represents a difluoromethyl group, a 2,2-difluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 1,1,1,3,3,3-hexafluoroisopropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a 2,2,3,3,4,4-hexafluorobutyl group, or a 2,2,3,3,4,4,5,5-octafluoropentyl group.