# US 2014/0154587 A1 · Non-aqueous electrolyte and electricity storage device using same

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- Number: US 2014/0154587 A1
- Document ID: US20140154587A1
- Status: Published application
- Kind: A1
- Application number: 14/237,492
- Filed: 2012-08-07
- Published: 2014-06-05
- Earliest claimed: 2011-08-12
- Assignees: Ube Industries, Ltd.
- Inventors: Koji Abe; Kei Shimamoto
- Web page: https://patentgrep.com/patent/US20140154587A1

## CPC

- H01M 10/0567: characterised by the additives
- C07C 69/65: of unsaturated acids
- C07C 309/65: of a saturated carbon skeleton
- C07D 327/00: Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- H01M 4/13: Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
- H01M 4/131: Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx
- H01M 4/386: {Silicon or alloys based on silicon}
- H01M 4/387: {Tin or alloys based on tin}
- H01M 4/485: of mixed oxides or hydroxides for inserting or intercalating light metals, e.g. LiTi2O4 or LiTi2OxFy (H01M4/505, H01M4/525 take precedence)
- H01M 4/505: of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
- H01M 4/52: of nickel, cobalt or iron
- H01M 4/5825: {Oxygenated metallic salts or polyanionic structures, e.g. borates, phosphates, silicates, olivines}
- H01M 4/583: Carbonaceous material, e.g. graphite-intercalation compounds or CFx
- 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 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- 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
- 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)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

The present invention provides a nonaqueous electrolytic solution capable of improving electrochemical characteristics in a broad temperature range, such as low-temperature cycle properties and low-temperature discharge properties after high-temperature storage, and provides an energy storage device using the nonaqueous electrolytic solution. The invention includes (1) a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises from 0.001 to 10% by mass of a compound represented by the following general formula (I), and (2) an energy storage device comprising a positive electrode, a negative electrode, and a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, wherein the nonaqueous electrolytic solution is the nonaqueous electrolytic solution of (1). (In the formula, Y represents a group —C(═O)— or a group —S(═O)2—; R3 and R4 each independently represent an aryl group having from 6 to 10 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, or R3 and R4 bonding to each other represent a cycloalkanediyl group or a benzenediyl group, having from 5 to 12 carbon atoms. R represents —C(R1)(R2)— or -L-; R1 and R2 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms; and L represents a divalent linking group having from 1 to 6 carbon atoms and optionally substituted with a halogen atom.)

## Claims

### Claim 1

A nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises from 0.001 to 10% by mass of a compound of formula (I):
wherein
Y is a group —C(═O)— or a group —S(═O)2—;
R3 and R4 are each independently an aryl group having from 6 to 10 carbon atoms in which a hydrogen atom is substituted with a halogen atom, or R3 and R4 bonding to each other are a cycloalkanediyl group having from 5 to 12 carbon atoms or a benzenediyl group, and the cycloalkanediyl group and the benzenediyl group may have a substituent;
R is —C(R1)(R2)— or -L-;
R1 and R2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms; and
L is a divalent linking group having from 1 to 6 carbon atoms and optionally substituted with a halogen atom.

### Claim 2

A nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises from 0.001 to 10% by mass of a compound of formula (II):
wherein
Y is a group —C(═O)— or a group —S(═O)2—;
R1 and R2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms; and
A is a cycloalkanediyl group having from 5 to 12 carbon atoms or a benzenediyl group, which may have a substituent.

### Claim 3

A nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises from 0.001 to 10% by mass of a compound of formula (III):
wherein
Y is a group —C(═O)— or a group —S(═O)2—;
R21 and R22 are each independently a halogenoalkyl group having from 1 to 4 carbon atoms;
X21 and X22 are each independently a halogen atom;
L is a divalent linking group having from 1 to 6 carbon atoms and optionally substituted with a halogen atom; and
m, n, p and q are each independently an integer of from 0 to 5, satisfying 1≦m+n≦5 and 1≦p+q≦5.

### Claim 4 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, wherein the nonaqueous solvent comprises a cyclic carbonate and a linear ester.

### Claim 5 (depends on 4)

The nonaqueous electrolytic solution according to claim 4, wherein the cyclic carbonate is at least one selected from the group consisting of ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 2,3-butylene carbonate, 4-fluoro-1,3-dioxolan-2-one, trans or cis-4,5-difluoro-1,3-dioxolan-2-one, vinylene carbonate, and vinylethylene carbonate.

### Claim 6 (depends on 4)

The nonaqueous electrolytic solution according to claim 4, wherein the linear ester is an asymmetric linear carbonate selected from the group consisting of methyl ethyl carbonate, methyl propyl carbonate, methyl isopropyl carbonate, methyl butyl carbonate and ethyl propyl carbonate, a symmetric linear carbonate selected from the group consisting of dimethyl carbonate, diethyl carbonate, dipropyl carbonate and dibutyl carbonate, a linear carboxylate, or any combination thereof.

### Claim 7 (depends on 6)

The nonaqueous electrolytic solution according to claim 6, wherein the linear ester is a methyl group-comprising linear ester selected from the group consisting of methyl ethyl carbonate, methyl propyl carbonate, methyl isopropyl carbonate, methyl butyl carbonate, dimethyl carbonate, methyl propionate, methyl acetate and ethyl acetate.

### Claim 8 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, wherein the electrolyte salt comprises at least one selected from the group consisting of LiPF6, LiPO2F2, Li2PO3F, LiBF4, LiN(SO2CF3)2, LiN(SO2C2F5)2, LiN(SO2F)2, lithium difluorobis[oxalate-O,O′]phosphate and lithium tetrafluoro[oxalate-O,O′]phosphate.

### Claim 9 (depends on 1)

The nonaqueous electrolytic solution according to claim 1, wherein a concentration of the electrolyte salt is from 0.3 to 2.5 M relative to the nonaqueous solvent therein.

### Claim 10 (depends on 1)

An energy storage device comprising a positive electrode, a negative electrode, and a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, wherein the nonaqueous electrolytic solution is the nonaqueous electrolytic solution of claim 1.

### Claim 11 (depends on 10)

The energy storage device according to claim 10, wherein the positive electrode active material is a composite metal oxide with lithium that comprises at least one selected from the group consisting of cobalt, manganese and nickel, or a lithium-comprising olivine-type phosphate that comprises at least one selected from the group consisting of iron, cobalt, nickel and manganese.

### Claim 12 (depends on 10)

The energy storage device according to claim 10, wherein the negative electrode active material comprises at least one selected from the group consisting of lithium metal, lithium alloy, and carbon material capable of absorbing and releasing lithium, tin, tin compounds, silicon, silicon compounds, and lithium titanate compounds.

### Claim 13

A cycloalkanedisulfonate compound of formula (II-1):
wherein
R33 and R34 are each independently a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms; and
R5 to R14 are each independently a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms, an aryl group having from 6 to 12 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms, wherein R5 to R14 may bond to each other to form a ring structure, and a hydrogen atom thereof may be substituted with a halogen atom; and n is an integer of from 0 to 3.

### Claim 14

An alkanedisulfonate compound of formula (III-1):
wherein
R23 and R24 are each independently a fluoroalkyl group having from 1 to 4 carbon atoms;
L is a divalent linking group having from 1 to 6 carbon atoms and optionally substituted with a halogen atom; and
m, n, p and q are each independently an integer of from 0 to 5, satisfying 1≦m+n≦5 and 1≦p+q≦5.