IP Library Granted Patent US 12,148,889
Granted Patent B2
US 12,148,889 · App. 16/960,594 · Granted Nov 19, 2024

Non-aqueous electrolyteincluding lithium bis(fluorosulfonyl)imide, fluorinated acyclic carboxylic acid ester, organic carbonate and electrolyte salt

Inventors: Daniel Hancock (Media, PA); Du-Hyun Won (Cheongju-si, KR); Hyuncheol Lee (Gyeonggi-do, KR); Hyung Kwon Hwang (Seoul, KR); Eun-Ji Moon (Seoul, KR)
Assignee: SYENSQO SA
H01M10/0569H01M10/0525H01M10/0567H01M10/0568H01M2300/0034
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Quick Facts
Patent No.
US 12,148,889
App. No.
16/960,594
Granted
Nov 19, 2024
Kind
B2
Abstract

Disclosed are electrolyte compositions comprising a fluorinated acyclic carboxylic acid ester, lithium bis(fluorosulfonyl)imide (also called LiFSI); and at least one electrolyte salt. The electrolyte compositions are useful in electrochemical cells, such as lithium-ion batteries.

Claims (29)

1. An electrolyte composition comprising:

from 50 to about 80% by weight of a fluorinated solvent,

lithium bis (fluorosulfonyl) imide (LiFSI), in an amount of from 0.3% to about 5.0% by weight, based on the total weight of the electrolyte composition;

at least one linear or cyclic organic carbonate, that is fluorinated or non-fluorinated in an amount of from about 20% to about 40% by weight of the electrolyte composition; and

a main electrolyte different from LiFSI and in a greater amount than LiFSI, at a concentration ranging from 0.5 to 1.2M, and selected from the group consisting of lithium hexafluorophosphate (LiPF 6 ), lithium bis (trifluoromethanesulfonyl) imide, lithium bis (perfluoroethanesulfonyl) imide, lithium (fluorosulfonyl) (nonafluorobutanesulfonyl) imide, lithium tetrafluoroborate, lithium perchlorate, lithium hexafluoroarsenate, lithium trifluoromethanesulfonate, lithium tris (trifluoromethanesulfonyl) methide, Li 2 B 12 F 12-x H x where x is equal to 0 to 8, mixtures of lithium fluoride and anion receptor B (OC 6 F 5 ) 3 and mixtures thereof,

wherein the fluorinated solvent is an acyclic carboxylic acid esters represented by the formula:

R 1 —COO—R 2

wherein

i) R 1 is an alkyl group;

ii) R 2 is a fluoroalkyl group; and

iii) R 1 and R 2 , taken as a pair, comprise at least two carbon atoms but not more than seven carbon atoms.

2. The electrolyte composition according to claim 1 , wherein LiFSI is present in the electrolyte composition in the range of from 0.5% to 2.0% by weight, based on the total weight of the electrolyte composition.

3. The electrolyte according to claim 1 ,

wherein the main electrolyte comprises lithium hexafluorophosphate (LiPF 6 ) or lithium bis (trifluoromethanesulfonyl) imide.

4. The electrolyte composition according to claim 1 , wherein said organic carbonate is selected from the group consisting of fluoroethylene carbonate, trifluoroethylene carbonate; ethylene carbonate; ethyl methyl carbonate; difluoroethylene carbonate, tetrafluoroethylene carbonate; dimethyl carbonate; diethyl carbonate; propylene carbonate; vinylene carbonate; di-tert-butyl carbonate; 2,2,3,3-tetrafluoropropyl methyl carbonate; bis (2,2,3,3-tetrafluoropropyl) carbonate; bis (2,2,2-trifluoroethyl) carbonate; 2,2,2-trifluoroethyl methyl carbonate; bis (2,2-difluoroethyl) carbonate; 2,2-difluoroethyl methyl carbonate; dipropyl carbonate; methyl propyl carbonate; ethyl propyl vinylene carbonate; methyl butyl carbonate; ethyl butyl carbonate; propyl butyl carbonate; dibutyl carbonate; vinyl ethylene carbonate; dimethylvinylene carbonate; 2,3,3-trifluoroallyl methyl carbonate; and isomers and mixtures thereof.

5. The electrolyte composition according to claim 1 , wherein said one or more organic carbonate is present in the electrolyte composition in the range of from about 25% to about 35% by weight of the electrolyte composition.

6. The electrolyte composition according to claim 1 , wherein the electrolyte composition further comprises an additive.

7. The electrolyte composition according to claim 6 , wherein the additive is a lithium boron compound, a cyclic sultone, a cyclic sulfate, a cyclic carboxylic acid anhydride or a combination thereof.

8. The electrolyte composition according to claim 1 , wherein the fluorinated solvent is selected from the group consisting of 2,2-difluoroethyl acetate, 2,2,2-trifluoroethyl acetate, 2,2-difluoroethyl propionate, 3,3-difluoropropyl acetate, 3,3-difluoropropyl propionate, and mixtures thereof.

9. The electrolyte composition according to claim 8 , wherein the fluorinated solvent is selected from the group consisting of 2,2-difluoroethyl acetate, 2,2-difluoroethyl propionate, 2,2,2-trifluoroethyl acetate, and mixtures thereof.

10. The electrolyte composition according to claim 9 , wherein the fluorinated solvent is 2,2-difluoroethyl acetate.

11. An electrochemical cell comprising:

(a) a housing;

(b) an anode and a cathode disposed in the housing and in ionically conductive contact with one another;

(c) electrolyte composition according to claim 1 .

12. An electronic device, transportation device, or telecommunications device, comprising an electrochemical cell according to claim 11 .

13. A method for forming an electrolyte composition according to claim 1 , wherein said method comprises combining the fluorinated solvent; LiFSI, the linear or cyclic organic carbonate, that is fluorinated or non-fluorinated, and the electrolyte salt to form the electrolyte composition.

14. A method for improving cycle performance, and/or storage performance, of a lithium ion battery, wherein said method comprises the step of incorporating LiFSI in an amount of from 0.3% to about 5.0% by weight, based on the total weight of an electrolyte composition in an electrolyte composition comprising from 50% by weight to about 80% by weight of a fluorinated solvent, at least one linear or cyclic organic carbonate in an amount of from about 20% to about 40% by weight, based on the total weight of the electrolyte composition, and a main electrolyte different from LiFSI and in a greater amount than LiFSI, at a concentration ranging from 0.5 to 1.2 M and,

selected from the group consisting of lithium hexafluorophosphate (LiPF 6 ), lithium bis (trifluoromethanesulfonyl) imide, lithium bis (perfluoroethanesulfonyl) imide, lithium (fluorosulfonyl) (nonafluorobutanesulfonyl) imide, lithium tetrafluoroborate, lithium perchlorate, lithium hexafluoroarsenate, lithium trifluoromethanesulfonate, lithium tris (trifluoromethanesulfonyl) methide, Li 2 B 12 F 12-x H x where x is equal to 0 to 8, and mixtures of lithium fluoride and anion receptor B (OC 6 F 5 ) 3 and mixtures thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: SOLVAY SA
To: SYENSQO SA
Reel/Frame 066406/0174 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2021
From: HANCOCK, DANIEL; WON, DU-HYUN; LEE, HYUNCHEOL; HWANG, HYUNG KWON; MOON, EUN-JI
To: SOLVAY SA
Reel/Frame 054915/0080 →
Priority Claims (1)
EP 18158776 · Feb 27, 2018 · regional
Continuity (2)
Provisional Application 62616510 · Jan 12, 2018
Related Publication 20200335825A1 · Oct 22, 2020