IP Library Granted Patent US 12671114
Granted Patent B2
US 12671114 · App. 16/892,757 · Granted Jun 30, 2026

Silicon-based energy storage devices with LiPO

Inventors: Liwen Ji (San Diego, CA); Benjamin Yong Park (Mission Viejo, CA)
Assignee: Enevate Corporation
H01M10/0568H01G11/06H01G11/50H01G11/52H01G11/60H01G11/62H01G11/64H01G11/84H01M4/134H01M4/362H01M4/386H01M4/62H01M10/0525H01M10/0567H01M10/0569H01M2300/0025
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Quick Facts
Patent No.
US 12671114
App. No.
16/892,757
Granted
Jun 30, 2026
Kind
B2
Abstract

Electrolytes and electrolyte additives for energy storage devices comprising lithium difluorophosphate (LiPO 2 F 2 ) and an electrolyte additive are disclosed. The energy storage device comprises a first electrode and a second electrode, wherein at least one of the first electrode and the second electrode is a Si-based electrode, a separator between the first electrode and the second electrode, an electrolyte, a lithium-containing salt comprising LiPO 2 F 2 , and at least one electrolyte additive compound.

Claims (28)

1 . An energy storage device comprising:

a first electrode and a second electrode, wherein one or both of the first electrode and the second electrode is a Si-based electrode;

a separator between the first electrode and the second electrode;

an electrolyte;

a lithium-containing salt comprising lithium difluorophosphate (LiPO 2 F 2 ); and

at least one electrolyte additive;

where said at least one electrolyte additive is selected from the group consisting of allyl cyclohexyl carbonate; N-(allyloxycarbonyloxy)succinimide; 2,2,3,3,3-pentafluoropropyl 2,2,2-trifluoroethyl carbonate; ethyl propargyl carbonate; 3-trimethylsiloxy-1-propyne; glycidyl propargyl ether; 1-fluoroethyl propagyl carbonate; 1-(prop-2-yn-1-yl)-2,5-dihydro-1H-pyrrole-2,5-dione; 2,2-difluoroethyl propargyl carbonate; 2,2,3,3,3-pentafluoropropyl propargyl carbonate; vinylboronic acid MIDA ester; isopropenylboronic acid MIDA ester; cyclopropylboronic acid MIDA ester; 2-cyclobutyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-cyclopentyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-cyclohexyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-ethynyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-butyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; isopropenylboronic anhydride pyridine complex; trivinylboroxin; thiophene-2-boronic acid pinacol ester; 4-methylthiophene-3-boronic acid pinacol ester; 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine; 3-cyano-1-propylboronic acid pinacol ester; allylboronic acid pinacol ester; 2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; cyclopropylboronic acid pinacol ester; cyclohexylboronic acid pinacol ester; pyridine-3-boronic acid 1,3-propanediol ester; 2,5-difluoropyridine-4-boronic acid, pinacol ester; 2,6-difluoropyridine-3,5-diboronic acid, pinacol ester; tris(2H-hexafluoroisopropyl) borate; boric acid tris-(2-oxo-[1,3]dioxolan4-ylmethyl) ester; tris(prop-2-enyl) borate; triallyl phosphite; diallyl hydrogen phosphate; dimethyl vinyl phosphate; bis(ethenyl) phosphate; tris(ethenyl) phosphate; bis(ethenyl) ethyl phosphate; tris(2,3-epoxypropyl) isocyanurate; 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; tris[2-(acryloyloxy)ethyl]isocyanurate; vinyltrisopropenoxysilane; vinyl tris(trimethylsiloxy)silane; 1,5-diethenyl-3-[(ethenyldimethylsilyl)oxy]-1,1,3,5,5-pentamethylpentanetrisiloxane; and 4-(tert-butyldimethylsilyloxy)-1-butyne.

2 . The energy storage device of claim 1 , wherein the second electrode is a Si-dominant electrode.

3 . The energy storage device of claim 1 , wherein the second electrode comprises a self-supporting composite material film.

4 . The energy storage device of claim 3 , wherein the composite material film comprises:

greater than 0% and less than 90% by weight of silicon particles, and

greater than 0% and less than 90% by weight of one or more types of carbon phases, wherein at least one of the one or more types of carbon phases is a substantially continuous phase that holds the composite material film together such that the silicon particles are distributed throughout the composite material film.

5 . The energy storage device of claim 1 , wherein the electrolyte further comprises fluoroethylene carbonate (FEC).

6 . The energy storage device of claim 5 , wherein the electrolyte is substantially free of non-fluorine containing cyclic carbonate.

7 . A method of forming an energy storage device, the method comprising: forming an energy storage device comprising a cathode, an electrolyte, and a Si-based anode, wherein said electrolyte contains a lithium-containing salt comprising

lithium difluorophosphate (LiPO 2 F 2 ); and

at least one electrolyte additive; wherein said one or both of said cathode and said anode is formed using, at least, the following steps:

an electrode material is mixed to create a slurry;

said slurry is coated on metal foil; and

the coated metal foil is dried; and

where said at least one electrolyte additive is selected from the group consisting of allyl cyclohexyl carbonate; N-(allyloxycarbonyloxy)succinimide; 2,2,3,3,3-pentafluoropropyl 2,2,2-trifluoroethyl carbonate; ethyl propargyl carbonate; 3-trimethylsiloxy-1-propyne; glycidyl propargyl ether; 1-fluoroethyl propagyl carbonate; 1-(prop-2-yn-1-yl)-2,5-dihydro-1H-pyrrole-2,5-dione; 2,2-difluoroethyl propargyl carbonate; 2,2,3,3,3-pentafluoropropyl propargyl carbonate; vinylboronic acid MIDA ester; isopropenylboronic acid MIDA ester; cyclopropylboronic acid MIDA ester; 2-cyclobutyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-cyclopentyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-cyclohexyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-ethynyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 2-butyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; isopropenylboronic anhydride pyridine complex; trivinylboroxin; thiophene-2-boronic acid pinacol ester; 4-methylthiophene-3-boronic acid pinacol ester; 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine; 3-cyano-1-propylboronic acid pinacol ester; allylboronic acid pinacol ester; 2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; cyclopropylboronic acid pinacol ester; cyclohexylboronic acid pinacol ester; pyridine-3-boronic acid 1,3-propanediol ester; 2,5-difluoropyridine-4-boronic acid, pinacol ester; 2,6-difluoropyridine-3,5-diboronic acid, pinacol ester; tris(2H-hexafluoroisopropyl) borate; boric acid tris-(2-oxo-[1,3]dioxolan4-ylmethyl) ester; tris(prop-2-enyl) borate; triallyl phosphite; diallyl hydrogen phosphate; dimethyl vinyl phosphate; bis(ethenyl) phosphate; tris(ethenyl) phosphate; bis(ethenyl) ethyl phosphate; tris(2,3-epoxypropyl) isocyanurate; 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; tris[2-(acryloyloxy)ethyl]isocyanurate; vinyltrisopropenoxysilane; vinyl tris(trimethylsiloxy) silane; 1,5-diethenyl-3-[(ethenyldimethylsilyl)oxy]-1,1,3,5,5-pentamethylpentanetrisiloxane; and 4-(tert-butyldimethylsilyloxy)-1-butyne.

8 . The method of claim 7 , wherein the Si-based anode is a Si-dominant anode.

9 . The method of claim 7 , wherein the Si-based anode comprises a self-supporting composite material film.

10 . The method of claim 9 , wherein the composite material film comprises:

greater than 0% and less than 90% by weight of silicon particles, and

greater than 0% and less than 90% by weight of one or more types of carbon phases, wherein at least one of the one or more types of carbon phases is a substantially continuous phase that holds the composite material film together such that the silicon particles are distributed throughout the composite material film.

11 . The method of claim 7 , wherein the electrolyte further comprises fluoroethylene carbonate (FEC).

12 . The method of claim 11 , wherein the electrolyte is substantially free of non-fluorine containing cyclic carbonate.