IP Library Granted Patent US 12,469,880
Granted Patent B2
US 12,469,880 · App. 17/734,585 · Granted Nov 11, 2025

Electrolyte additives for lithium-sulfur rechargeable battery

Inventor: Gao Liu (Piedmont, CA)
Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
H01M10/0567C07C43/126H01M10/0569H01M10/0525H01M2300/0034
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Quick Facts
Patent No.
US 12,469,880
App. No.
17/734,585
Granted
Nov 11, 2025
Kind
B2
Abstract

The present invention provides for an amphiphilic molecule having a profluorinated alkyl-methyloligoethyleneoxide structure. The present invention also provides for an electrolyte composition comprising an amphiphilic molecule of the present invention, an electrolyte solvent, and a lithium salt.

Claims (35)

1 . An amphiphilic molecule having the following structure:

wherein R is

m is an integer from 2 to 21;

a is an integer from 0 to 20; b is an integer from 0 to 4; and

n is an integer from 1 to 20.

2 . The amphiphilic molecule of claim 1 , wherein m is 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19; b is 0, 1, 2, or 3; and, n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19.

3 . The amphiphilic molecule of claim 1 , wherein the amphiphilic molecule has the following structure:

wherein m is an integer from 2 to 21, a is an integer from 0 to 20, b is an integer from 0 to 4, and n is an integer from 1 to 20.

4 . The amphiphilic molecule of claim 1 , wherein R is

wherein m is an integer from 2 to 21; a is an integer from 1 to 20.

5 . The amphiphilic molecule of claim 1 , wherein the amphiphilic molecule has the following structure:

wherein m is an integer from 2 to 21; a is an integer from 1 to 20.

6 . The amphiphilic molecule of claim 3 , wherein the amphiphilic molecule has the chemical structure of

7 . The amphiphilic molecule of claim 3 , wherein the amphiphilic molecule has the chemical structure of

8 . The amphiphilic molecule of claim 1 , wherein the amphiphilic molecule is capable of self-formation of a micelle.

9 . A micelle comprising the amphiphilic molecule of claim 1 .

10 . The micelle of claim 9 , wherein the micelle is an inverse micelle, prolate micelle, inverse prolate micelle, normal hexagonal phase, inverse hexagonal phase inverse, or oblate micelle bilayered fragment.

11 . An electrolyte composition comprising an amphiphilic molecule of claim 1 , an electrolyte solvent, and a lithium salt.

12 . The electrolyte composition of claim 11 , wherein the electrolyte solvent is a highly fluorinated alkane, alkyl ether or alkyl tertiary amine comprising more F atoms than H atoms.

13 . The electrolyte composition of claim 12 , wherein the alkane has a main chain having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

14 . The electrolyte composition of claim 12 , wherein the alkane has a straight or branched chain.

15 . The electrolyte composition of claim 12 , wherein the alkane has a total of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

16 . The electrolyte composition of claim 11 , wherein the electrolyte solvent has the following chemical structure: R 1 —O—R 2 , or

wherein R 1 is —CH 3 , —C 2 H 5 , or —R 4 ; and R 2 , R 3 , and R 4 are each independently -α-C y H z F 2y+1−z , wherein a is -, —CHF—, —CF 2 —, or —CH 2 —; y is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and z is 0 or 1.

17 . The electrolyte composition of claim 16 , wherein —C y F y+2 is a straight chain alkyl.

18 . The electrolyte composition of claim 16 , wherein —C y F 2y+1 is a branched alkyl, and y is equal to or more than 3.

19 . The electrolyte composition of claim 16 , wherein R 1 and R 2 are identical; R 2 and R 3 are identical; or, R 1 , R 2 , and R 3 are identical.

20 . The electrolyte composition of claim 16 , wherein the electrolyte solvent is methoxyperfluorobutane, profluorinated alkane, bis(2,2,2-trifluoroethyl) ether, 1,1,2,2-tetrafluoroethyl-2′,2′,2′-trifluoroethyl ether, perfluorotributylamine, hydrofluoroether (HFE), or a mixture thereof.

21 . The electrolyte composition of claim 20 , wherein the profluorinated alkane is CF 3 (CF 2 ) x CF 3 , wherein x is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20.

22 . The electrolyte composition of claim 20 , wherein the hydrofluoroether (HFE) is CHF 2 CF 2 —O—CH 2 CF 2 CHF 2 , C 7 F 15 —O—C 2 H 5 , C 4 F 9 —O—C 2 H 5 , n-C 3 F 7 —O—CH 3 ), CF 3 CF 2 —O—CH 3 , CF 3 CHFCF 2 —O—CH 3 , CF 3 —O—CH 3 , CHF 2 —O—CHF 2 , CF 3 CF 2 —O—CH 3 ), or CF 3 —O—CHFCF 3 .

23 . The electrolyte composition of claim 22 , wherein the HFE is CHF 2 CF 2 —O—CH 2 CF 2 CHF 2 .

24 . The electrolyte composition of claim 11 , wherein the lithium salt is lithium bis(trifluoromethanesulfonyl) imide (LiTFSI), lithium bis (oxalato) borate (LiBOB), lithium bis(pentafluoroethanesulfonyl)imide (LiBETI), LiCIO 4 , lithium bis(fluorosulfonyl)imide (LiFSI), LiPF 6 , LiAsF 6 , or a mixture thereof.

25 . The electrolyte composition of claim 11 , wherein the lithium salt has an ionic association strength that is equal to or less than about the ionic association strength of LiBETI, and is equal to or more than about the ionic association strength of LiTFSI.

26 . An electrolyte composition comprising one or more amphiphilic molecules of claim 1 , or a mixture thereof; methoxyperfluorobutane, profluorinated alkane, bis(2,2,2-trifluoroethyl) ether, 1,1,2,2-tetrafluoroethyl-2′,2′,2′-trifluoroethyl ether, perfluorotributylamine, or a mixture thereof; and, LiTFSI, LiBOB, LiBETI, LiCIO 4 , LIFSI, LiPF 6 , LiAsF 6 , or a mixture thereof.

27 . A lithium ion battery comprising the electrolyte composition of claim 11 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Sep 2, 2022
From: UNIVERSITY OF CALIF-LAWRENC BERKELEY LAB
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 060979/0862 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2022
From: LIU, GAO
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 060225/0497 →
Continuity (3)
Continuation PCTUS2020058064 · Oct 29, 2020
Provisional Application 62929678 · Nov 1, 2019
Related Publication 20220336857A1 · Oct 20, 2022
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