IP Library Granted Patent US 11,539,077
Granted Patent B2
US 11,539,077 · App. 17/509,534 · Granted Dec 27, 2022

Electrolyte additives containing one, two, or more triple-bonded moieties for silicon anode-based li-ion batteries

Inventors: Liwen Ji (Irvine, CA); Benjamin Yong Park (Irvine, CA); Heidi Anderson (Irvine, CA); Sung Won Choi (San Diego, CA)
Assignee: Enevate Corporation
H01M10/0567H01M4/0404H01M4/386H01M10/0525C07F1/02H01M2300/0028
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Quick Facts
Patent No.
US 11,539,077
App. No.
17/509,534
Granted
Dec 27, 2022
Kind
B2
Abstract

Electrolyte additives for energy storage devices comprising compounds containing one, two, or more triple-bonded moieties 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, and an electrolyte composition. Compounds containing one, two, or more triple-bonded moieties may serve as additives to the electrolyte composition.

Claims (61)

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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of [(1,1-Dimethyl-2-propynyl)oxy]trimethylsilane; tert-Butyldimethyl(2-propynyloxy)silane;

trimethyl-[3-[2-(3-trimethylsilyloxyprop- 1 -ynyl)phenyl]prop-2-ynoxy]silane; or trimethyl(phenyl(prop-2-yn-1-yloxy)methyl)silane; or derivatives thereof.

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

3. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of 1-prop-2-ynylpyrrolidin-2-one; N-(3-Butynyl)phthalimide; N-Propargylphthalimide; Propargyl 1H-imidazole-1-carboxylate; Dipropargylamine; Tripropargylamine; Propargyl N-phenylcarbamate; Cyclo-(N-(propargyl)glycine)6; cyclo-(N-(propargyl)glycine)8; 2,4,6-tris(propargylamino)-1,3,5-triazine; or Propargyl-DOTA-tris(tBu)ester; or derivatives thereof.

4. The energy storage device of claim 3 , wherein the second electrode is a Si-dominant electrode.

5. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of Propargyl-PEG1-amine; Methyl propargyl ether; Propargyl ether; Phenyl propargyl ether; 1-adamantyl propargyl ether;

1,3,5-Tris(2-propyn-1-yloxy)benzene; 3-(prop-2-ynoxymethoxy)prop-1-yne; (3-(prop-2-ynyloxy)prop-1-ynyl)benzene; 2-((prop-2-yn-1-yloxy)methyl)furan; or 3-(3-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)propoxy)prop-1-yne; or derivatives thereof.

6. The energy storage device of claim 5 , wherein the second electrode is a Si-dominant electrode.

7. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of 3-prop-2-ynylsulfanylprop-1-yne; prop-2-yne -1-thiol; Phenyl propargyl sulfide; 3-(prop-2-ynyldithio)prop-1-yne; 2-prop-2-ynylthiophene; 3-(prop-2-ynyldithio)prop-1-yne; propargyl p-toluenesulfonate; 4-methyl-N-prop-2-ynylbenzenesulfonamide; prop-2-ynyl trifluoromethanesulfonate;

Propargyl benzenesulfonate; Propargyl p-toluenesulfonate; 3-Butynyl p-toluenesulfonate; 2-(prop-2-yn-1-yloxy)ethyl 4-methylbenzenesulfonate; or 4-Propargyl thiomorpholine-1,1-dioxide; or derivatives thereof.

8. The energy storage device of claim 7 , wherein the second electrode is a Si-dominant electrode.

9. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of tris[(prop-2-yn-1-yloxy)methyl]phosphane oxide; or oxo-bis(prop-2-ynoxy)phosphanium; or derivatives thereof.

10. The energy storage device of claim 9 , wherein the second electrode is a Si-dominant electrode.

11. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of Tripropargyl boroxine or derivatives thereof.

12. The energy storage device of claim 11 , wherein the second electrode is a Si-dominant electrode.

13. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple- bonded moieties;

wherein said compound containing one, two, or more triple-bonded moieties comprises one or more of trilithiated but-1-yne; or dilithiated 3-methyl -but-1-yne; or derivatives thereof.

14. The energy storage device of claim 13 , wherein the second electrode is a Si-dominant electrode.

15. 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; and

an electrolyte composition; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a compound containing one, two, or more triple-bonded moieties;

wherein the second electrode comprises a self-supporting composite material film which comprises:

greater than 0% and less than about 95% by weight of silicon particles, and

greater than 0% and less than about 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.

16. The energy storage device of claim 15 , wherein the second electrode is a Si-dominant electrode.

Assignments (2)
SECURITY INTEREST Recorded Mar 10, 2026
From: ENEVATE CORPORATION
To: MCANDREWS, HELD & MALLOY LTD.
Reel/Frame 075093/0935 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2021
From: JI, LIWEN; PARK, BENJAMIN; ANDERSON, HEIDI; CHOI, SUNG WON
To: ENEVATE CORPORATION
Reel/Frame 057943/0472 →
Continuity (2)
Provisional Application 63106753 · Oct 28, 2020
Related Publication 20220131195A1 · Apr 28, 2022