IP Library Granted Patent US 12,224,439
Granted Patent B2
US 12,224,439 · App. 17/508,514 · Granted Feb 11, 2025

Boron-containing chemicals as cathode additives, Si anode additives, electrolyte additives or separator modifiers for Li-ion batteries

Inventors: Liwen Ji (Irvine, CA); Benjamin Park (Irvine, CA); Hong Zhao (Irvine, CA)
Assignee: Enevate Corporation
H01M4/5825H01M4/386H01M4/525H01M10/0525H01M2004/027H01M2004/028H01M2220/20
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Quick Facts
Patent No.
US 12,224,439
App. No.
17/508,514
Granted
Feb 11, 2025
Kind
B2
Abstract

Electrodes, electrolytes and/or separators for energy storage devices comprising functional boron-containing chemicals 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. Functional boron-containing chemicals may serve as additives to one or more of the electrodes, electrolyte and/or separator.

Claims (40)

1. An energy storage device comprising:

an anode and a cathode, where at least one of the anode or the cathode contains an electrode additive;

a separator between the anode and the cathode; and

an electrolyte composition; wherein said electrode additive comprises at least one boron-containing compound; and

wherein the boron-containing compound comprises one or more of: Cyclopropylboronic acid MIDA ester (CAS 1104637-36-6); 2-cyclobutyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 1104637-37-7); 2-cyclopentyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 117311-84-9); 2-cyclohexyl-6-methyl 1,3,6,2-dioxazaborocane-4,8-dione (CAS: 1104637-39-9); anhydride; 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; Cyclopropylboronic acid pinacol ester; Cyclohexylboronic acid pinacol ester; Pyridine-3-boronic acid 1,3-propanediol ester; 2,5-Difluoropyridine-4-boronic acid, pinacol ester (CAS: 1622217-35-9); or 2,6-Difluoropyridine-3,5-diboronic acid, pinacol ester (CAS: 1218789-90-2).

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

3. The energy storage device of claim 1 , wherein the cathode comprises one or more of: nickel cobalt aluminum oxide (NCA), nickel cobalt manganese oxide (NCM), lithium iron phosphate (LFP), lithium cobalt oxide (LCO), lithium manganese oxide (LMO), Ni-rich layered oxides (LiNi 1-x MxO 2 , Mn=Co, Mn, and Al), Li-rich, xLi 2 MnO 3 ·(1-x)LiNi a CobMn c O 2 , Li-rich layered oxides (LiNi 1+x M 1-x O 2 , Mn=Co, Mn, and Ni), or high-voltage spinel oxides (LiNi 0.5 Mn 1.5 O 4 ).

4. The energy storage device of claim 1 , wherein said electrode additive comprises 5% or less by weight of the active material of the electrode.

5. The energy storage device of claim 4 , wherein said electrode additive comprises 1% or less by weight of the active material of the electrode.

6. The energy storage device of claim 2 , wherein the anode comprises an active material that comprises between about 50% to about 95% silicon by weight.

7. The energy storage device of claim 1 , wherein the energy storage device comprises a lithium ion battery.

8. The energy storage device of claim 1 , wherein the electrolyte comprises a liquid, solid, or gel.

9. An energy storage device comprising:

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; wherein

said electrolyte composition comprises at least one electrolyte additive comprising a boron-containing compound; and

wherein the boron-containing compound comprises one or more of: Cyclopropylboronic acid MIDA ester (CAS 1104637-36-6); 2-cyclobutyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 1104637-37-7); 2-cyclopentyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 117311-84-9); Phenylboronic acid trimeric anhydride; 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; Cyclopropylboronic acid pinacol ester; Cyclohexylboronic acid pinacol ester; Pyridine-3-boronic acid 1,3-propanediol ester; 2,5-Difluoropyridine-4-boronic acid, pinacol estser (CAS: 1622217-35-9); or 2,6-Difluoropyridine-3,5-diboronic acid, pinacol ester (CAS: 1218789-90-2).

10. The energy storage device of claim 9 , wherein the second electrode comprises an active material that comprises between about 50% to about 95% silicon.

11. The energy storage device of claim 9 , wherein the energy storage device comprises a lithium ion battery.

12. The energy storage device of claim 9 , wherein the electrolyte composition comprises a liquid, solid, or gel.

13. The energy storage device of claim 9 , wherein the second electrode comprises a self-supporting composite material film.

14. The energy storage device of claim 13 , wherein the composite material film 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.

15. A method of forming an energy storage device, the method comprising:

forming an energy storage device comprising a cathode, an electrolyte composition, and an anode;

wherein said one or more of said cathode or said anode and/or said electrolyte composition comprise an additive compound;

said additive compound comprising a boron-containing compound;

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

said electrode active material is mixed to create a slurry;

said electrolyte composition is added to said slurry;

said slurry is coated on metal foil; and

the coated metal foil is dried; and

wherein the boron-containing compound comprises one or more of: Cyclopropylboronic acid MIDA ester (CAS 1104637-36-6); 2-cyclobutyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 1104637-37-7); 2-cyclopentyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 117311-84-9); 2-cyclohexyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (CAS: 1104637-39-9); anhydride; 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; Cyclopropylboronic acid pinacol ester; Cyclohexylboronic acid pinacol ester; Pyridine-3-boronic acid 1,3-propanediol ester; 2,5-Difluoropyridine-4-boronic acid, pinacol estser (CAS: 1622217-35-9); or 2,6-Difluoropyridine-3,5-diboronic acid, pinacol ester (CAS: 1218789-90-2).

16. The method of claim 15 , wherein the anode is a Si-dominant electrode.

17. The method of claim 15 , wherein the anode comprises a self-supporting composite material film.

18. The method of claim 17 , wherein the composite material film 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.

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; ZHAO, HONG
To: ENEVATE CORPORATION
Reel/Frame 057943/0257 →
Continuity (2)
Provisional Application 63106731 · Oct 28, 2020
Related Publication 20220131148A1 · Apr 28, 2022
References Cited (17)
US 5891592A · Mao · 1999 [cited by examiner]
US 20120183866A1 · Lee · 2012 [cited by examiner]
US 20170338476A1 · Newbound et al. · 2017 [cited by applicant]
US 20190131655A1 · Haruna · 2019 [cited by examiner]
US 20190181440A1 · Park · 2019 [cited by examiner]
US 20200136185A1 · Ji et al. · 2020 [cited by applicant]
US 20200148710A1 · Zhang et al. · 2020 [cited by applicant]
US 20220216513A1 · Tang · 2022 [cited by examiner]
JP 61214374A · 1986 [cited by applicant]
JP 2009245829 · 2009 [cited by examiner]
JP 2009245829A · 2009 [cited by examiner]
WO WO2017185997A1 · 2017 [cited by examiner]
International Search Report, PCT/US21/56501, dated Jan. 21, 2022, 14 pages. [cited by applicant]
Jang et al., Chemically-Induced Cathode-Electrolyte Interphase Created By Lithium Salt Coating on Nickel-Rich Layered Oxides Cathode, Journal of Power Sources, vol. 410-411, 2019, pp. 15-24. [cited by applicant]
Song et al., Artificial Cathode-Electrolyte Interphases on Nickel-Rich Cathode Materials Modified by Sily Functional Group, Journal of Power Sources, vol. 416, 2019, pp. 1-8. [cited by applicant]
International Preliminary Report on Patentability, PCT/US2021/056504, dated May 11, 2023, 13 pages. [cited by applicant]
“Triphenylboroxin | C18H15B3O3—PubChem,” Web page <https://pubchem.ncbi.nlm.nih.gov/compound/Triphenylboroxin>, 20 pages, retrieved from Internet on Dec. 6, 2022. [cited by applicant]