# US 2020/0287218 A1 · Sulfur-containing compounds and polymers and the use thereof in electrochemical cells

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- Number: US 2020/0287218 A1
- Document ID: US20200287218A1
- Status: Published application
- Kind: A1
- Application number: 16/644,714
- Filed: 2018-10-02
- Published: 2020-09-10
- Earliest claimed: 2017-10-02
- Assignees: Hydro-Quebec
- Applicants: Hydro-QuéBec
- Inventors: Rachel LÉVESQUE-BÉLANGER; Andrea PAOLELLA; Jean-Christophe DAIGLE; Basile COMMARIEU; Michel ARMAND; Karim ZAGHIB
- Web page: https://patentgrep.com/patent/US20200287218A1

## CPC

- H01M 4/602: {Polymers}
- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C08G 73/1064: {containing sulfur}
- C08G 75/14: Polysulfides
- H01M 4/137: Electrodes based on electro-active polymers
- H01M 4/38: of elements or alloys
- H01M 4/623: {fluorinated polymers}
- H01M 4/625: {Carbon or graphite}
- H01M 10/05: Accumulators with non-aqueous electrolyte (H01M10/39 takes precedence)
- H01M 10/052: Li-accumulators
- H01M 10/0565: Polymeric materials, e.g. gel-type or solid-type
- H01M 10/0567: characterised by the additives
- H01M 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- H01M 2300/0025: Organic electrolyte
- H01M 2300/0082: Organic polymers
- H01M 2300/0085: Immobilising or gelification of 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present technology relates to a sulfur-containing polymer or organic compound for use in a positive electrode material, especially in lithium batteries. More specifically, the use of this sulfur-containing polymer or compound as an active electrode material makes it possible to combine sulfur and an active organic cathode material. The present technology also relates to the use of the sulfur-containing polymer or organic compound as defined herein as a solid polymer electrolyte (SPE) or as an additive for electrolyte, especially in lithium batteries.

## Claims

### Claim 1

Polymer of Formula I:
wherein:
A is selected from unsaturated groups allowing the delocalization of electrons, for example, substituted or unsubstituted aryl and heteroaryl groups, and their fused or unfused polycyclic equivalents;
R is a substituted or unsubstituted organic linking group selected from linear or branched C2-6 alkylene, linear or branched C2-6 alkyleneoxy, linear or branched C2-6alkyleneglycol, linear or branched C2-6 alkyleneoxyC2-6 alkylene, linear or branched poly(C2-6 alkyleneglycol), C6-12arylene, C3-12cycloalkylene, C5-12heteroarylene, and C3-12 heterocycloalkylene;
m represents the average number of sulfur atoms inserted into the disulfide bond of the polymer links and cannot be zero, i.e. m>0, for example, 0<m≤8, or 1≤m≤6, or 1≤m≤4; and
n represents the average number of units in the polymer, for example, n may be in the range of 2 to 500, or of 5 to 300.

### Claim 2 (depends on 1)

Polymer according to claim 1, wherein A is selected from benzene, naphthalene, perylene, and biphenyl groups.

### Claim 3 (depends on 1, 2)

Polymer according to claim 1 or 2, the polymer being of Formula I(a):
wherein R, m and n are as defined in claim 1.

### Claim 4 (depends on 1, 2, 3)

Polymer according to any one of claims 1 to 3, wherein R is selected from the groups benzene, ethylene, propylene, poly(ethylene glycol), poly(propylene glycol), and copolymers of ethylene glycol and propylene glycol.

### Claim 5 (depends on 1, 4)

Polymer according to claim 4, the polymer being of Formula I(b):
wherein m and n are as defined in claim 1.

### Claim 6 (depends on 1, 2, 4)

Compound of Formula II:
wherein A and R are as defined in any one of claims 1, 2 and 4; and m represents the number of sulfur atoms inserted into the disulfide bond of the compound, for example, m>0, for example, 0<m≤8, or 1≤m≤6, or 1≤m≤4.

### Claim 7 (depends on 6)

Compound according to claim 6, the compound being of Formula II(a):
wherein R and m are as defined in claim 6.

### Claim 8 (depends on 6)

Compound according to claim 6, the compound being of Formula II(b):
wherein m is as defined in claim 6.

### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8)

Electrode material comprising a polymer as defined in any one of claims 1 to 5 or a compound as defined in any one of claims 6 to 8.

### Claim 10 (depends on 9)

Electrode material according to claim 9, further comprising elemental sulfur.

### Claim 11 (depends on 9, 10)

Electrode material according to claim 9 or 10, further comprising a conductive material, a binder, or a combination of both.

### Claim 12 (depends on 11)

Electrode material according to claim 11, wherein the conductive material is selected from carbon black, Ketjen™ carbon, Shawinigan carbon, acetylene black, graphite, graphene, carbon fibers (such as carbon nanofibers (for example, VGCF formed in the gas phase)), and carbon nanotubes, or a combination of at least two thereof.

### Claim 13 (depends on 11, 12)

Electrode material according to claim 11 or 12, wherein the binder is a polymeric binder of polyether type, a fluorinated polymer, or a water-soluble binder.

### Claim 14 (depends on 13)

Electrode material according to claim 13, wherein the polymeric binder of polyether type is linear, branched and/or crosslinked and is based on poly(ethylene oxide) (PEO), poly(propylene oxide) (PPO), or a mixture of the two (or an EO/PO co-polymer), and optionally comprises crosslinkable units.

### Claim 15 (depends on 13)

Electrode material according to claim 13, wherein the fluorinated polymer binder is PVDF (polyvinylidene fluoride) or PTFE (polytetrafluoroethylene).

### Claim 16 (depends on 13)

Electrode material according to claim 13, wherein the water-soluble binder is SBR (styrene-butadiene rubber), NBR (acrylonitrile-butadiene rubber), HNBR (hydrogenated NBR), CHR (epichlorohydrin rubber), or ACM (acrylate rubber), optionally comprising CMC (carboxymethyl cellulose).

### Claim 17 (depends on 9, 10, 11, 12, 13, 14, 15, 16)

Positive electrode comprising an electrode material according to any one of claims 9 to 16 applied on a current collector.

### Claim 18 (depends on 1, 2, 3, 4, 5, 6, 7, 8)

Electrolyte comprising a polymer as defined in any one of claims 1 to 5 or a compound as defined in any one of claims 6 to 8.

### Claim 19 (depends on 18)

Electrolyte according to claim 18, the electrolyte being a liquid electrolyte comprising a salt in a solvent.

### Claim 20 (depends on 18)

Electrolyte according to claim 18, the electrolyte being a gel electrolyte comprising a salt in a solvent and optionally a solvating polymer.

### Claim 21 (depends on 19, 20)

Electrolyte according to claim 19 or 20, the solvent being a polar aprotic solvent selected from ethylene carbonate (EC), diethyl carbonate (DEC), propylene carbonate (PC), dimethyl carbonate (DMC), ethylmethyl carbonate (EMC), γ-butyrolactone (γ-BL), vinylene carbonate (VC), methyl butyrate (MB), γ-valerolactone (γ-VL), 1,2-dimethoxyethane (DME), 1,2-diethoxyethane (DEE), 2-methyltetrahydrofuran, dimethylsulfoxide, formamide, acetamide, dimethylformamide, dioxolane, acetonitrile, propylnitrile, nitromethane, ethylmonoglyme, trimethoxymethane, dioxolane derivatives, sulfolane, methylsulfolane, propylene carbonate derivatives, tetrahydrofuran, and mixtures thereof.

### Claim 22 (depends on 18)

Electrolyte according to claim 18, the electrolyte being a solid polymer electrolyte (SPE) comprising a salt in a solvating polymer.

### Claim 23 (depends on 18, 19, 20, 21, 22)

Electrolyte according to any one of claims 18 to 22, the polymer or the compound being an additive.

### Claim 24 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 22)

Electrolyte according to claim 22, the solvating polymer being the polymer as defined in any one of claims 1 to 5 or the compound as defined in any one of claims 6 to 8.

### Claim 25 (depends on 18, 19, 20, 21, 22, 23, 24)

Electrolyte according to any one of claims 18 to 24, the electrolyte further comprising elemental sulfur.

### Claim 26 (depends on 19, 20, 21, 22, 23, 24, 25)

Electrolyte according to any one of claims 19 to 25, the salt being a lithium salt.

### Claim 27 (depends on 26)

Electrolyte according to claim 26, the salt being selected from lithium hexafluorophosphate (LiPF6), lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), lithium bis(fluorosulfonyl)imide (LiFSI), lithium 2-trifluoromethyl-4,5-dicyanoimidazolate (LiTDI), lithium 4,5-dicyano-1,2,3-triazolate (LiDCTA), lithium bis(pentafluoroethylsulfonyl)imide (LiBETI), lithium tetrafluoroborate (LiBF4), lithium bis(oxalato)borate (LiBOB), lithium nitrate (LiNO3), lithium chloride (LiCl), lithium bromide (LiBr), lithium fluoride (LiF), lithium perchlorate (LiClO4), lithium hexafluoroarsenate (LiAsF6), lithium trifluoromethanesulfonate (LiSO3CF3) (LiTf), lithium fluoroalkylphosphate Li[PF3(CF2CF3)3] (LiFAP), lithium tetrakis(trifluoroacetoxy)borate Li[B(OCOCF3)4] (LiTFAB), lithium bis(1,2-benzenediolato(2-)-O,O′)borate Li[B(C6O2)2] (LBBB) and a combinations thereof.

### Claim 28 (depends on 18, 19, 20, 21, 22, 23, 24, 25, 26, 27)

Electrolyte according to any one of claims 18 to 27, the electrolyte further comprising an electrolyte binder.

### Claim 29 (depends on 28)

Electrolyte according to claim 28, wherein the electrolyte binder is a polymeric binder of polyether type, a fluorinated polymer, or a water-soluble binder.

### Claim 30 (depends on 29)

Electrolyte according to claim 29, wherein the fluorinated polymer binder is polyvinylidene fluoride (PVDF).

### Claim 31 (depends on 9, 10, 11, 12, 13, 14, 15, 16)

Electrochemical cell comprising a cathode, an electrolyte and an anode, wherein the cathode comprises an electrode material as defined in any one of claims 9 to 16.

### Claim 32 (depends on 17)

Electrochemical cell comprising a negative electrode, an electrolyte and a positive electrode as defined in claim 17.

### Claim 33 (depends on 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)

Electrochemical cell comprising a cathode, an anode and an electrolyte as defined in any one of claims 18 to 30.

### Claim 34 (depends on 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)

Electrochemical cell comprising a negative electrode, an electrolyte and a positive electrode, wherein the positive electrode is as defined in claim 17 and the electrolyte is as defined in any one of claims 18 to 30.

### Claim 35 (depends on 31, 32, 33, 34)

Lithium battery comprising an electrochemical cell as defined in any one of claims 31 to 34.