# US 12,224,439 B2 · Boron-containing chemicals as cathode additives, Si anode additives, electrolyte additives or separator modifiers for Li-ion batteries

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- Number: US 12,224,439 B2
- Document ID: US12224439B2
- Status: Granted
- Kind: B2
- Application number: 17/508,514
- Filed: 2021-10-22
- Published: 2022-04-28
- Granted: 2025-02-11
- Earliest claimed: 2020-10-28
- Assignees: Enevate Corporation
- Applicants: Enevate Corporation
- Inventors: Liwen Ji; Benjamin Park; Hong Zhao
- Web page: https://patentgrep.com/patent/US12224439B2

## CPC

- H01M 4/5825: {Oxygenated metallic salts or polyanionic structures, e.g. borates, phosphates, silicates, olivines}
- H01M 4/0404: {by coating on electrode collectors}
- H01M 4/386: {Silicon or alloys based on silicon}
- H01M 4/525: of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
- H01M 10/04: Construction or manufacture in general (H01M10/058, H01M10/12, H01M10/28, H01M10/38 take precedence)
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/056: characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M 2004/027: {Negative electrodes}
- H01M 2004/028: {Positive electrodes}
- H01M 2220/20: Batteries in motive systems, e.g. vehicle, ship, plane
- Y02E 60/10: Energy storage using batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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

### Claim 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).

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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 (LiNi1-xMxO2, Mn=Co, Mn, and Al), Li-rich, xLi2MnO3·(1-x)LiNiaCobMncO2, Li-rich layered oxides (LiNi1+xM1-xO2, Mn=Co, Mn, and Ni), or high-voltage spinel oxides (LiNi0.5Mn1.5O4).

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 2)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

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

### Claim 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).

### Claim 10 (depends on 9)

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

### Claim 11 (depends on 9)

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

### Claim 12 (depends on 9)

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

### Claim 13 (depends on 9)

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

### Claim 14 (depends on 13)

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.

### Claim 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).

### Claim 16 (depends on 15)

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

### Claim 17 (depends on 15)

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

### Claim 18 (depends on 17)

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.