# US 12,015,147 B2 · Additives for electrolyte and cathode material in Li-ion batteries comprising metal-based cathode material which produces M2+ metal ions

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- Number: US 12,015,147 B2
- Document ID: US12015147B2
- Status: Granted
- Kind: B2
- Application number: 17/268,120
- Filed: 2019-08-13
- Published: 2021-09-30
- Granted: 2024-06-18
- Earliest claimed: 2018-08-14
- Assignees: Hydro-Quebec; Murata Manufacturing Co., Ltd.
- Applicants: Hydro-QuéBec; Murata Manufacturing Co., Ltd.
- Inventors: Charlotte Mallet; Jean-Christophe Daigle; Sylviane Rochon; Karim Zaghib
- Web page: https://patentgrep.com/patent/US12015147B2

## CPC

- H01M 10/0567: characterised by the additives
- C08F 8/12: Hydrolysis
- C08F 112/22: {Oxygen}
- C08F 212/20: {Fluorine}
- C08F 212/22: {Oxygen}
- C08F 212/24: {Phenols or alcohols}
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/4235: {Safety or regulating additives or arrangements in electrodes, separators or electrolyte (H01M10/4242 takes precedence)}
- C08F 2438/01: Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
- C08F 2800/10: as molar percentages
- C08F 2810/50: wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
- H01M 4/622: {being polymers}
- H01M 2300/0025: Organic electrolyte
- Y02E 60/10: Energy storage using batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Method of improving the performance of a Li-ion battery comprising metal-based cathode material which produces M2+ metal ions. The method comprises using a small organic compound in association with the electrolyte of the battery or using a polymer compound in association with the cathode active material of the battery. The small organic compound and the polymer compound comprise at least one chemical group suitable for forming complexes with the M2+ metal ions thereby preventing dissolution thereof.

## Claims

### Claim 1

A polymer compound having a general formula VI outlined below
wherein:
Q and Q′ are each independently a 5 to 12-member ring or bicycle ring, optionally either ring comprises one or more heteroatom which are the same or different;
L is a linker comprising alkyl groups;
Ri and R′i are each independently selected from H, alkyl, cycloalkyl, alkene, alkyne, aryl and alkylaryl, alkoxy, thioalkoxy, OH, SH, NH2, a halogen atom, a halogeno alkyl, a halogeno alkoxy, a halogeno thioalkoxy, a cyano alkyl, a cyano alkene, a cyano alkyne, CN, NO2, SO2, COOH and acyloxycarbonyl, with the proviso that at least one of Ri comprises a heteroatom and at least one of R′i is different from H;
n and m are each independently an integer from 0 to 11 with the proviso that they are not both 0 at the same time; and
the one or more heteroatom of Q or Q′ is selected from O, S and N.

### Claim 2 (depends on 1)

The polymer according to claim 1, wherein at least two of Ri comprise a heteroatom, and the at least two of Ri are attached to consecutive carbon atoms of the ring; or when Q is a bicycle ring the at least two of Ri are spatially close to each other.

### Claim 3 (depends on 1)

The polymer according to claim 1, wherein the at least one R′i is a halogen atom, optionally F.

### Claim 4 (depends on 1)

The polymer compound according to claim 1 having a general formula VII outlined below
wherein:
at least two of Ri comprise a heteroatom, and the at least two of Ri are attached to consecutive carbon atoms of the ring; or when Q is a bicycle ring the at least two of Ri are spatially close to each other; and
the at least one R′i is a halogen atom, optionally F.

### Claim 5 (depends on 1)

The polymer compound according to claim 1 having a general formula VIII outlined below
wherein:
both R1 and R2 comprise a heteroatom, optionally both R1 and R2 comprise a heteroatom, and are attached to consecutive carbon atoms of the ring; and
R′1-5 are each a halogen atom, optionally F.

### Claim 6 (depends on 1)

The polymer compound according to claim 1 having a general formula IX outlined below
wherein:
R3, R4 and R6-9 are each independently H or a C1-6 alkyl;
R′1-5 are each a halogen atom, optionally F;
L′ is constituted of repeating units of CR6R7 and CR8R9; and
X1 and X2 are each independently a heteroatom, optionally the X1 or X2 heteroatom is O, S or N.

### Claim 7 (depends on 6)

The polymer compound according to claim 6 having a formula P outlined below

### Claim 8 (depends on 6)

The polymer compound according to claim 6 having a formula P′ outlined below

### Claim 9 (depends on 7)

The polymer according to claim 7, which is selected from the group consisting of: polymer of formula P, which comprises 48 mol % of dimethoxystyrene moities (Polymer dimethoxy-1); polymer of formula P, which comprises 70 mol % of dimethoxystyrene moities (Polymer dimethoxy-2); and polymer of formula P, which comprises 100 mol % of dimethoxystyrene moities (Polymer dimethoxy-3).

### Claim 10 (depends on 8)

The polymer according to claim 8, which is: polymer of formula P′, which comprises 50 mol % of dihydroxystyrene moities (Polymer difydroxy-1).

### Claim 11 (depends on 1)

A method of preventing metal ions dissolution in a Li-ion battery comprising metal-based cathode material which produces M2+ metal ions, the method comprising using adding a polymer compound in association with to the cathode material of the battery, wherein the polymer compound is as defined in claim 1.

### Claim 12 (depends on 1)

A cathode material comprising the polymer compound as defined in claim 1.

### Claim 13 (depends on 12)

A battery comprising the cathode material as defined in claim 12.

### Claim 14 (depends on 1)

A method for preparing the polymer compound as defined in claim 1, comprising submitting a dialkyloxystyrene compound and a pentahalogenostyrene compound to a random copolymerization to obtain an alkyoxystyrene polymer; and optionally submitting the alkyoxystyrene polymer to a dealkylation process to obtain a hydroxy polymer compound.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the dialkyloxystyrene compound is dimethoxystyrene, and the pentahalogenostyrene compound is pentafluorostyrene.

### Claim 16 (depends on 7)

A method for preparing the polymer compound of formula P as defined in claim 7, comprising submitting dimethoxystyrene and pentafluorostyrene to a random copolymerization.

### Claim 17 (depends on 8)

A method for preparing the polymer compound of formula P′ as defined in claim 8, comprising submitting a polymer compound of formula P to a demethylation process:

### Claim 18 (depends on 1)

A method for preparing the polymer compound as defined in claim 1, comprising submitting a dialkyloxystyrene compound and a pentahalogenostyrene compound to a polymerization process which is atom transfer radical polymerization (ATRP), atom transfer radical addition polymerization (ATRAP), retarded anionic polymerization (RAP), or cationic polymerization.