Sulfur-containing compounds and polymers and the use thereof in electrochemical cells

Patent metadata

Field	Value
Publication number	US-12431499-B2
Application number	US-202217895307-A
Country	US
Kind code	B2
Filing date	Aug 25, 2022
Priority date	Oct 2, 2017
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

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.

First claim

The invention claimed is:

1. A compound Compound-of Formula II:

wherein:
A is an unsaturated group allowing the delocalization of electrons selected from substituted or unsubstituted aryl and heteroaryl groups, and their fused or unfused polycyclic equivalents;
R is an organic linking group selected from unsubstituted linear or branched C 2-6 alkylene, substituted or unsubstituted linear or branched C 2-6 alkyleneoxy, substituted or unsubstituted linear or branched C 2-6 alkyleneglycol, substituted or unsubstituted linear or branched C 2-6 alkyleneoxyC 2-6 alkylene, substituted or unsubstituted linear or branched poly (C 2-6 alkyleneglycol), substituted or unsubstituted C 6-12 arylene, substituted or unsubstituted C 3-12 cycloalkylene, substituted or unsubstituted C 5-12 heteroarylene, and substituted or unsubstituted C 3-12 heterocycloalkylene; and
m represents the number of sulfur atoms inserted into the disulfide bond of the compound and cannot be zero.

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

3. The compound according to claim 1 , wherein R is selected from the groups benzene, ethylene, propylene, poly (ethylene glycol), poly (propylene glycol), and copolymers of ethylene glycol and propylene glycol.

4. The compound according to claim 1 , wherein m is 0<m≤8.

5. The compound according to claim 1 , wherein m is 1≤m≤6.

6. The compound according to claim 1 , wherein m is 1≤m≤4.

7. The compound according to claim 1 , the compound being of Formula II (a):

wherein R and m are as defined in claim 1 .

8. The compound according to claim 1 , the compound being of Formula II (b):

wherein m is as defined in claim 1 .

9. An electrode material comprising a compound as defined in claim 1 , and optionally elemental sulfur and/or a conductive material, a binder, or a combination of both.

10. The electrode material according to claim 9 , wherein the conductive material is selected from carbon black, graphite, graphene, carbon fibers, and carbon nanotubes, or a combination of at least two thereof.

11. The electrode material according to claim 9 , wherein the binder is a polymeric binder of polyether type, a fluorinated polymer, or a water-soluble binder.

12. The electrode material according to claim 11 , 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), a mixture of the two, for an EO/PO co-polymer), and optionally comprises crosslinkable units;
the fluorinated polymer binder is PVDF (polyvinylidene fluoride) or PTFE (polytetrafluoroethylene); or
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).

13. A positive electrode comprising an electrode material as defined in claim 9 applied on a current collector.

14. An electrochemical cell comprising a cathode, an electrolyte and an anode, wherein the cathode comprises an electrode material as defined in claim 9 .

15. A lithium battery comprising an electrochemical cell as defined in claim 14 .

16. An electrolyte comprising a compound as defined in claim 1 , and optionally elemental sulfur.

17. The electrolyte according to claim 16 , the electrolyte being a liquid electrolyte comprising a salt in a solvent or a gel electrolyte comprising a salt in a solvent and optionally a solvating polymer or a solid polymer electrolyte (SPE) comprising a salt in a solvating polymer.

18. The electrolyte according to claim 17 , wherein the solvent of the liquid or gel electrolyte is 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.

19. The electrolyte according to claim 17 , wherein the salt of the liquid, gel or solid polymer electrolyte is a lithium salt selected from lithium hexafluorophosphate (LiPF 6 ), 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 (LiBF 4 ), lithium bis (oxalato)borate (LiBOB), lithium nitrate (LiNO 3 ), lithium chloride (LiCl), lithium bromide (LiBr), lithium fluoride (LiF), lithium perchlorate (LiClO 4 ), lithium hexafluoroarsenate (LiAsF 6 ), lithium trifluoromethanesulfonate (LiSO 3 CF 3 ) (LiTf), lithium tris(pentafluoroethyl)trifluorophosphate Li[PF 3 (CF 2 CF 3 ) 3 ] (LiFAP), lithium tetrakis (trifluoroacetoxy)borate Li[B(OCOCF 3 ) 4 ] (LiTFAB), lithium bis(1,2-benzenediolato (2-)-O,O′)borate Li[B(C 6 O 2 ) 2 ] (LBBB) and combinations thereof.

20. The electrolyte according to claim 16 , the compound being an additive.

21. The electrolyte according to claim 16 , the electrolyte further comprising an electrolyte binder.

22. An electrochemical cell comprising a cathode, an anode and an electrolyte as defined in claim 16 .

23. A lithium battery comprising an electrochemical cell as defined in claim 22 .

Assignees

• Hydro Quebec

Inventors

• Lévesque-Bélanger Rachel
• Paolella Andrea
• Daigle Jean-Christophe
• Commarieu Basile
• Armand Michel
• Zaghib Karim

Classifications

• H01M2300/0085

  Immobilising or gelification of electrolyte · CPC title

• H01M2300/0082

  Organic polymers · CPC title

• H01M2300/0025

  Organic electrolyte · CPC title

• H01M10/0569

  characterised by the solvents · CPC title

• H01M10/0568

  characterised by the solutes · CPC title