IP Library › Granted Patent US 12,431,537
Granted Patent B2
US 12,431,537 · App. 19/172,319 · Granted Sep 30, 2025

Electrolyte including electrolyte solvent, fluoroether, and bis(fluorosulfonyl) salt, and lithium metal electrochemical cells including the same

Inventors: Junhua Song (Sudbury, MA); Junzheng Chen (Concord, MA); Dhanya Puthusseri (Millis, MA); Frank Yongzhen Fan (Arlington, MA)
Assignee: 24M Technologies, Inc.
H01M10/0568H01M4/382H01M4/5825H01M4/625H01M10/052H01M10/0562H01M10/0567H01M2004/027H01M2004/028H01M2300/0034H01M2300/0037H01M2300/0068
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Quick Facts
Patent No.
US 12,431,537
App. No.
19/172,319
Filed
Apr 7, 2025
Granted
Sep 30, 2025
Kind
B2
Art Unit
1725
USPC
429/322
Abstract

Systems, devices, and methods described herein relate to electrolyte formulations and the incorporation thereof into batteries. In some aspects, an electrolyte composition can comprise between about 10 wt % and about 42 wt % of an electrolyte solvent, between about 13 wt % and about 59 wt % of a fluoroether. In some embodiments, the electrolyte solvent can make up between about 26 wt % and about 39 wt % of the composition. In some embodiments, the fluoroether can make up between about 18 wt % and about 36 wt % of the composition. In some embodiments, the composition can include between about 0.5 wt % and about 1.5 wt % of a first additive. In some embodiments, the composition can include between about 0.5 wt % and about 5 wt % of a second additive.

Claims (84)

1. A method of forming an electrolyte, comprising:

forming a first electrolyte solution, the first electrolyte solution including about 26 wt % to about 70 wt % of a first salt including bis(fluorosulfonyl)imide ions and about 30 wt % to about 74 wt % of a first electrolyte solvent;

forming a second electrolyte solution, the second electrolyte solution including about 2 wt % to about 42 wt % of a second salt and about 38 wt % to about 98 wt % of a second electrolyte solvent different from the first electrolyte solvent;

combining the first electrolyte solution and the second electrolyte solution to form an electrolyte mixture such that the electrolyte mixture includes about 10 wt % to about 90 wt % of the first electrolyte solution and about 10 wt % to about 90 wt % of the second electrolyte solution; and

incorporating the electrolyte mixture into an electrochemical cell such that the electrolyte mixture forms the electrolyte of the electrochemical cell.

2. The method of claim 1 , wherein the electrolyte mixture includes about 20 wt % to about 30 wt % of the first electrolyte solution and about 70 wt % to about 80 wt % of the second electrolyte solution.

3. The method of claim 1 , wherein the first electrolyte solution comprises an electrolyte additive, the electrolyte additive including at least one of tris-(trimethylsilyl) phosphate (TMSP), trimethoxy (3,3,3-trifluoropropyl)silane (TTS), pentafluorophenyltriethoxysilane (TPS), boric acid tris(trimethylsilyl) ester (TMSB), tris-(pentafluorophenyl)silane (TPFPS), 1,10-sulfonyldiimidazole (SDM), trioxane, lithium difluorophosphate, lithium difluoro oxalato borate, lithium nitrate, (pentafluorophenyl)diphenylphosphine (PFPDPP), cetyltrimethylammonium bromide (CTAB), sodium dodecyl sulfate (SDS), polyethylene-glycol (PEG-8000), benzotriazole (BTA), thiourea (CH 4 N 2 S), sodium dodecyl benzene sulfonate (SDBS), LiTFSI, PVA, PEG, or CMC.

4. The method of claim 1 , wherein the electrolyte mixture comprises:

about 10 wt % to about 42 wt % of a product solvent, the product solvent including a mixture of the first electrolyte solvent and the second electrolyte solvent;

about 13 wt % to about 43 wt % of a fluoroether (FE); and

about 22 wt % to about 43 wt % of the first salt, wherein the FE includes a compound having the following structure:

where n1 and n2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

5. The method of claim 1 , wherein the second salt includes LiBF4 in a range of about 4 wt % to 19 wt % of the second electrolyte solution.

6. The method of claim 1 , wherein bis(fluorosulfonyl) imide ions included in the first salt, or the second salt includes at least one of LiFSI or NaFSI.

7. The method of claim 6 , wherein the LiFSI or NaFSI is in a range of about 2 wt % to about 42 wt % of the first electrolyte solution.

8. The method of claim 1 , wherein:

the first electrolyte solvent includes at least one of 1,2-dimethoxyethane, bis-(2-fluoro-ethyl)-ether, 1,2-diethoxyethane, bis(2-methoxyethyl) ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, diethyl ether, dipropyl ether, 1,2-dipropoxyethane, dibutoxyethane, 1,2-diethoxypropane, dimethyl carbonate, 1,3-dioxolane, 1,4-dioxolane, ethyl methyl carbonate, diethyl carbonate, dimethyl sulfoxide, ethyl vinyl sulfone, tetramethylene sulfone, ethyl methyl sulfone, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, 4-vinyl-1,3-dioxolan-2-one, dimethyl sulfone, methyl butyrate, ethyl propionate, trimethyl phosphate, triethyl phosphate, gamma-butyrolactone, 4-methylene-1,3-dioxolan-2-one, methylene ethylene carbonate, 4,5-dimethylene-1,3-dioxolan-2-one, allyl ether, triallyl amine, triallyl cyanurate, triallyl isocyanurate, water, carbonate, fluorobutane, or tetrahydropyran; and

the second electrolyte solvent includes a fluoroether (FE).

9. The method of claim 8 , wherein the fluoroether includes a compound having the following structure:

where n 1 and n 2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

10. The method of claim 8 , wherein at least one of the first salt or the second salt includes at least one of lithium bis(fluorosulfonyl) imide (F 2 LiNO 4 S 2 ), lithium bis(trifluoromethylsulfonyl) imide (LiC 2 F 6 NO 4 S 2 ), lithium bis(oxalato)borate, lithium hexafluorophosphate (LiPF 6 ), lithium hexafluoroarsenate (LiAsF 6 ), lithium bis(trifluoromethane) sulfonimide (LiN(SO 2 CF 3 ) 2 ), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), lithium perchlorate (LiClO 4 ), lithium difluoro oxalato borate (LiBF 2 (C 2 O 4 )), lithium iodide (LiI), lithium bromide (LiBr), lithium chloride (LiCl), lithium hydroxide (LiOH), lithium nitrate (LiNO 3 ), lithium 2-trifluoromethyl-4,5-dicyanoimidazole (LiTDI), lithium sulfate (LiSO 4 ), lithium difluorophosphate (LiPO 2 F 2 ), or lithium tetrafluoroborate (LiBF 4 ).

11. The method of claim 1 , further comprising:

forming a third electrolyte solution, the third electrolyte solution including a third salt and a third electrolyte solvent; and

combining the third electrolyte solution with the first electrolyte solution and the second electrolyte solution to form the electrolyte mixture.

12. The method of claim 11 , wherein the third salt includes at least one of lithium bis(fluorosulfonyl) imide (F 2 LiNO 4 S 2 ), lithium bis(trifluoromethylsulfonyl) imide (LiC 2 F 6 NO 4 S 2 ), lithium bis(oxalato)borate, lithium hexafluorophosphate (LiPF 6 ), lithium hexafluoroarsenate (LiAsF 6 ), lithium bis(trifluoromethane) sulfonimide (LiN(SO 2 CF 3 ) 2), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), lithium perchlorate (LiClO 4 ), lithium difluoro oxalato borate (LiBF 2 (C 2 O 4 )), lithium iodide (LiI), lithium bromide (LiBr), lithium chloride (LiCl), lithium hydroxide (LiOH), lithium nitrate (LiNO 3 ), lithium 2-trifluoromethyl-4,5-dicyanoimidazole (LiTDI), lithium sulfate (LiSO 4 ), lithium difluorophosphate (LiPO 2 F 2 ), lithium tetrafluoroborate (LiBF 4 ).

13. The method of claim 11 , wherein the third electrolyte solution includes at least one of 1,2-dimethoxyethane, bis(2-methoxyethyl) ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, diethyl ether, dipropyl ether, 1,2-dipropoxyethane, dibutoxyethane, 1,2-diethoxypropane, bis-(2-fluoro-ethyl)-ether, 1,2-diethoxyethane, dimethyl carbonate, 1,3-dioxolane, 1,4-dioxolane, ethyl methyl carbonate, diethyl carbonate, tetrahydropyran, dimethyl sulfoxide, ethyl vinyl sulfone, tetramethylene sulfone, ethyl methyl sulfone, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, 4-vinyl-1,3-dioxolan-2-one, dimethyl sulfone, methyl butyrate, ethyl propionate, trimethyl phosphate, triethyl phosphate, gamma-butyrolactone, 4-methylene-1,3-dioxolan-2-one, methylene ethylene carbonate, 4,5-dimethylene-1,3-dioxolan-2-one, allyl ether, triallyl amine, triallyl cyanurate, triallyl isocyanurate, water, carbonate, fluorobutane, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, bis(2,2,2-trifluoroethyl) ether, 1,1,2,2,-tetrafluoroethyl-2,2,2-trifluoroethyl ether, tris(2,2,2-trifluoroethyl)orthoformate, pentafluoroethyl 2,2,2-trifluoroethyl ether, 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, methoxynonafluorobutane, ethoxynonafluorobutane, 2,2,2-trifluoroethyl nonafluorobutanesulfonate, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, bis(2,2,2-trifluoroethyl) ether, 1,1,2,2,-tetrafluoroethyl-2,2,2-trifluoroethyl ether, tris(2,2,2-trifluoroethyl)orthoformate, pentafluoroethyl 2,2,2-trifluoroethyl ether, 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, or 3,3,4,4,5,5-hexafluorotetrahydropyran.

14. A method of forming an electrolyte, comprising:

forming a first electrolyte solution, the first electrolyte solution including about 26 wt % to about 70 wt % of a first salt and about 30 wt % to about 74 wt % of a first electrolyte solvent;

forming a second electrolyte solution, the second electrolyte solution including about 2 wt % to about 42 wt % of a second salt and about 38 wt % to about 98 wt % of a second electrolyte solvent different from the first electrolyte solvent, the second electrolyte solvent including a fluoroether; and

combining the first electrolyte solution and the second electrolyte solution to form an electrolyte mixture such that the electrolyte mixture includes about 10 wt % to about 90 wt % of the first electrolyte solution and about 10 wt % to about 90 wt % of the second electrolyte solution, the electrolyte mixture configured to be incorporated into an electrochemical cell to form the electrolyte of the electrochemical cell.

15. The method of claim 14 , wherein the fluoroether includes bis(2-fluoroethyl) ether (BFE).

16. The method of claim 14 , wherein the first salt includes bis(fluorosulfonyl)imide ions.

17. The method of claim 14 , wherein the first salt includes at least one of lithium bis(fluorosulfonyl)imide (F 2 LiNO 4 S 2 ), lithium bis(trifluoromethylsulfonyl) imide (LiC 2 F 6 NO 4 S 2 ), lithium bis(oxalato)borate, lithium hexafluorophosphate (LiPF 6 ), lithium hexafluoroarsenate (LiAsF 6 ), lithium bis(trifluoromethane) sulfonimide (LiN(SO 2 CF 3 ) 2 ), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), lithium perchlorate (LiClO 4 ), lithium difluoro oxalato borate (LiBF 2 (C 2 O 4 )), lithium iodide (LiI), lithium bromide (LiBr), lithium chloride (LiCl), lithium hydroxide (LiOH), lithium nitrate (LiNO 3 ), lithium 2-trifluoromethyl-4,5-dicyanoimidazole (LiTDI), lithium tetrafluoroborate (LiBF 4 ), lithium sulfate (LiSO 4 ), or lithium difluorophosphate (LiPO 2 F 2 ).

18. The method of claim 14 , wherein the electrolyte mixture includes about 20 wt % to about 30 wt % of the first electrolyte solution and about 70 wt % to about 80 wt % of the second electrolyte solution.

19. The method of claim 14 , wherein the electrolyte mixture includes about 70 wt % to about 80 wt % of the first electrolyte solution and about 20 wt % to about 30 wt % of the second electrolyte solution.

20. The method of claim 14 , wherein the electrolyte mixture includes about 40 wt % to about 60 wt % of the first electrolyte solution and about 40 wt % to about 60 wt % of the second electrolyte solution.

21. The method of claim 14 , wherein the fluoroether includes a compound having the following structure:

where n 1 and n 2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

22. The method of claim 14 , wherein the electrolyte mixture comprises:

about 10 wt % to about 42 wt % of a product solvent, the product solvent including a mixture of the first electrolyte solvent and the second electrolyte solvent;

about 13 wt % to about 43 wt % of the fluoroether (FE); and

about 22 wt % to about 43 wt % of the first salt, wherein the FE includes a compound having the following structure:

where n1 and n2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

23. A method of forming an electrolyte, comprising:

forming a first electrolyte solution, the first electrolyte solution including a first salt including bis(fluorosulfonyl)imide ions and about 30 wt % to about 74 wt % of a first electrolyte solvent;

forming a second electrolyte solution, the second electrolyte solution including a second salt and about 38 wt % to about 98 wt % of a second electrolyte solvent different from the first electrolyte solvent, the second electrolyte solvent including a fluoroether;

combining the first electrolyte solution and the second electrolyte solution to form an electrolyte mixture such that the electrolyte mixture includes about 10 wt % to about 90 wt % of the first electrolyte solution and about 10 wt % to about 90 wt % of the second electrolyte solution, the electrolyte mixture configured to be combined with an anode, a cathode, and a separator to form an electrochemical cell,

wherein the electrolyte mixture comprises:

about 10 wt % to about 42 wt % of a product solvent, the product solvent including a mixture of the first electrolyte solvent and the second electrolyte solvent;

about 13 wt % to about 59 wt % of the fluoroether (FE); and

about 22 wt % to about 43 wt % of the first salt.

24. The method of claim 23 , wherein the fluoroether includes a compound having the following structure:

where n 1 and n 2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

25. The method of claim 23 , wherein the electrolyte mixture includes about 20 wt % to about 30 wt % of the first electrolyte solution and between about 70 wt % and about 80 wt % of the second electrolyte solution.

26. The method of claim 23 , wherein the electrolyte mixture includes about 70 wt % to about 80 wt % of the first electrolyte solution and about 20 wt % to about 30 wt % of the second electrolyte solution.

27. The method of claim 23 , wherein the electrolyte mixture includes about 40 wt % to about 60 wt % of the first electrolyte solution and about 40 wt % to about 60 wt % of the second electrolyte solution.

28. The method of claim 23 , wherein the first electrolyte solvent includes at least one of 1,2-dimethoxyethane, bis-(2-fluoro-ethyl)-ether, 1,2-diethoxyethane, bis(2-methoxyethyl) ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, diethyl ether, dipropyl ether, 1,2-dipropoxyethane, dibutoxyethane, 1,2-diethoxypropane, dimethyl carbonate, 1,3-dioxolane, 1,4-dioxolane, ethyl methyl carbonate, diethyl carbonate, dimethyl sulfoxide, ethyl vinyl sulfone, tetramethylene sulfone, ethyl methyl sulfone, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, 4-vinyl-1,3-dioxolan-2-one, dimethyl sulfone, methyl butyrate, ethyl propionate, trimethyl phosphate, triethyl phosphate, gamma-butyrolactone, 4-methylene-1,3-dioxolan-2-one, methylene ethylene carbonate, 4,5-dimethylene-1,3-dioxolan-2-one, allyl ether, triallyl amine, triallyl cyanurate, triallyl isocyanurate, water, carbonate, fluorobutane, or tetrahydropyran.

29. The method of claim 23 , further comprising:

forming a third electrolyte solution, the third electrolyte solution including a third salt and a third electrolyte solvent; and

combining the third electrolyte solution with the first electrolyte solution and the second electrolyte solution to form the electrolyte mixture.

30. The method of claim 29 , wherein the third salt includes at least one of lithium bis(fluorosulfonyl)imide (F 2 LiNO 4 S 2 ), lithium bis(trifluoromethylsulfonyl) imide (LiC 2 F 6 NO 4 S 2 ), lithium bis(oxalato)borate, lithium hexafluorophosphate (LiPF 6 ), lithium hexafluoroarsenate (LiAsF 6 ), lithium bis(trifluoromethane) sulfonimide (LiN(SO 2 CF 3 ) 2 ), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), lithium perchlorate (LiClO 4 ), lithium difluoro oxalato borate (LiBF 2 (C 2 O 4 )), lithium iodide (LiI), lithium bromide (LiBr), lithium chloride (LiCl), lithium hydroxide (LiOH), lithium nitrate (LiNO 3 ), lithium 2-trifluoromethyl-4,5-dicyanoimidazole (LiTDI), lithium sulfate (LiSO 4 ), lithium difluorophosphate (LiPO 2 F 2 ), lithium tetrafluoroborate (LiBF 4 ).

31. A method of forming an electrolyte, comprising:

forming a first electrolyte solution, the first electrolyte solution including about 26 wt % to about 70 wt % of a first salt including bis(fluorosulfonyl)imide ions and about 30 wt % to about 74 wt % of a first electrolyte solvent;

forming a second electrolyte solution, the second electrolyte solution including about 2 wt % to about 42 wt % of a second salt and about 38 wt % to about 98 wt % of a second electrolyte solvent different from the first electrolyte solvent; and

combining the first electrolyte solution and the second electrolyte solution to form the electrolyte such that the electrolyte includes about 10 wt % to about 90 wt % of the first electrolyte solution and about 10 wt % to about 90 wt % of the second electrolyte solution, wherein the electrolyte comprises:

about 10 wt % to about 42 wt % of a product solvent, the product solvent including a mixture of the first electrolyte solvent and the second electrolyte solvent;

about 13 wt % to about 43 wt % of a fluoroether (FE); and

about 22 wt % to about 43 wt % of the first salt, wherein the FE includes a compound having the following structure:

where n1 and n2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

32. The method of claim 31 , wherein the electrolyte includes about 20 wt % to about 30 wt % of the first electrolyte solution and about 70 wt % to about 80 wt % of the second electrolyte solution.

33. The method of claim 31 , wherein:

the first electrolyte solvent includes at least one of 1,2-dimethoxyethane, bis-(2-fluoro-ethyl)-ether, 1,2-diethoxyethane, bis(2-methoxyethyl) ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, diethyl ether, dipropyl ether, 1,2-dipropoxyethane, dibutoxyethane, 1,2-diethoxypropane, dimethyl carbonate, 1,3-dioxolane, 1,4-dioxolane, ethyl methyl carbonate, diethyl carbonate, dimethyl sulfoxide, ethyl vinyl sulfone, tetramethylene sulfone, ethyl methyl sulfone, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, 4-vinyl-1,3-dioxolan-2-one, dimethyl sulfone, methyl butyrate, ethyl propionate, trimethyl phosphate, triethyl phosphate, gamma-butyrolactone, 4-methylene-1,3-dioxolan-2-one, methylene ethylene carbonate, 4,5-dimethylene-1,3-dioxolan-2-one, allyl ether, triallyl amine, triallyl cyanurate, triallyl isocyanurate, water, carbonate, fluorobutane, or tetrahydropyran; and

the second electrolyte solvent includes a fluoroether (FE).

34. A method of forming an electrolyte, comprising:

forming a first electrolyte solution, the first electrolyte solution including about 26 wt % to about 70 wt % of a first salt and about 30 wt % to about 74 wt % of a first electrolyte solvent;

forming a second electrolyte solution, the second electrolyte solution including about 2 wt % to about 42 wt % of a second salt and about 38 wt % to about 98 wt % of a second electrolyte solvent different from the first electrolyte solvent, the second electrolyte solvent including a fluoroether; and

combining the first electrolyte solution and the second electrolyte solution to form the electrolyte such that the electrolyte includes about 10 wt % to about 90 wt % of the first electrolyte solution and about 10 wt % to about 90 wt % of the second electrolyte solution, wherein the electrolyte comprises:

about 10 wt % to about 42 wt % of a product solvent, the product solvent including a mixture of the first electrolyte solvent and the second electrolyte solvent;

about 13 wt % to about 43 wt % of the fluoroether (FE); and

about 22 wt % to about 43 wt % of the first salt,

wherein the FE includes a compound having the following structure:

where n1 and n2 each have values between 1 and 5, X=F, Br, Cl, or I, and n=1.

35. The method of claim 34 , wherein the fluoroether includes bis(2-fluoroethyl) ether (BFE).

36. The method of claim 34 , wherein the first salt includes bis(fluorosulfonyl)imide ions.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2025
From: SONG, JUNHUA; CHEN, JUNZHENG; PUTHUSSERI, DHANYA; FAN, FRANK YONGZHEN
To: 24M TECHNOLOGIES, INC.
Reel/Frame 071961/0261 →
Continuity (5)
Continuation 18747106 · Jun 18, 2024
Provisional Application 63633426 · Apr 12, 2024
Provisional Application 63545692 · Oct 25, 2023
Provisional Application 63545402 · Oct 24, 2023
Related Publication 20250260060A1 · Aug 14, 2025
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