Lithium salts of cyano-substituted imidazole for lithium ion batteries

Patent metadata

Field	Value
Publication number	US-12018000-B2
Application number	US-201816494435-A
Country	US
Kind code	B2
Filing date	Mar 27, 2018
Priority date	Mar 27, 2017
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

Here are described compounds for use as electrode additives or as salts in electrolyte compositions, and their methods of preparation. Also described are electrochemical cells comprising the compounds as electrode additives or as salts in electrolyte compositions.

First claim

The invention claimed is:

1. A compound as defined in Formula I:

wherein,
R 1 and R 2 are independently selected from H, F, CN, NO 2 , and optionally substituted alkyl;
R 3 is selected from —NHSO 2 R 4 , —NHSO 2 OR 4 , —SO 2 NHSO 2 R 4 , —SO 2 NHSO 2 OR 4 and an optionally substituted non-aromatic heterocycle having 5 or 6 cycle atoms linked through a nitrogen atom of the non-aromatic heterocycle;
R 4 is selected from fluorine, optionally substituted C 1-6 alkyl, and optionally substituted C 6 aryl; and
(M n+ ) 1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2;
or a tautomer thereof.

2. The compound of claim 1 , wherein M is Li, Na, or K, and n is 1.

3. The compound of claim 1 , wherein M is Li and n is 1.

4. The compound of claim 1 , wherein said compound is selected from:

or a tautomer thereof.

5. The compound of claim 1 , wherein at least one of R 1 and R 2 is CN.

6. The compound of claim 5 , wherein both of R 1 and R 2 are CN.

7. The compound of claim 1 , wherein R 3 is NHSO 2 R 4 , NHSO 2 OR 4 or a non-aromatic heterocycle having 5 or 6 cycle atoms linked through the nitrogen atom of the non-aromatic heterocycle.

8. The compound of claim 7 , wherein R 4 is a C 1-6 alkyl substituted with at least one of fluorine and alkoxy or a C 6 aryl substituted with at least one fluorine atom.

9. Electrode material comprising a compound as defined in claim 1 as an additive and at least one electrochemically active material.

10. An electrochemical cell comprising an electrolyte, an electrode and a counter-electrode, wherein at least one of the electrode or counter-electrode comprises an electrode material as defined in claim 9 .

11. An electrolyte composition comprising a compound as defined in claim 1 .

12. The electrolyte composition of claim 11 , further comprising a compatible organic or aqueous solvent.

13. The electrolyte composition of claim 11 , further comprising a compatible solvating polymer.

14. The electrolyte composition of claim 11 , wherein said compound is selected from:

or a tautomer thereof.

15. An electrochemical cell comprising an electrolyte, an electrode and a counter-electrode, wherein the electrolyte comprises an electrolyte composition as defined in claim 11 .

16. The electrochemical cell of claim 15 , wherein said electrochemical cell is a battery, an electrochromic device, or a capacitor.

17. The electrochemical cell of claim 16 , wherein said electrochemical cell is a lithium or lithium-ion battery.

18. A compound as defined in Formula I:

wherein,
R 1 and R 2 are independently selected from H, F, CN, NO 2 , and optionally substituted alkyl;
R 3 is selected from —NHSO 2 R 4 , —NHSO 2 OR 4 , —SO 2 NHSO 2 R 4 , —SO 2 NHSO 2 OR 4 and an optionally substituted non-aromatic heterocycle having 5 or 6 cycle atoms linked through a nitrogen atom;
R 4 is selected from fluorine, optionally substituted C 1-6 alkyl, and optionally substituted C 6 aryl; and
(M n+ ) 1/n is a metal cation, wherein M is lithium and n is 1;
or a tautomer thereof.

19. A compound as defined in Formula I:

wherein,
R 1 and R 2 are independently selected from H, F, CN, NO 2 , and optionally substituted alkyl, wherein at least one of R 1 and R 2 is CN;
R 3 is selected from —NHSO 2 R 4 , —NHSO 2 OR 4 , —SO 2 NHSO 2 R 4 , —SO 2 NHSO 2 OR 4 and an optionally substituted non-aromatic heterocycle having 5 or 6 cycle atoms linked through a nitrogen atom;
R 4 is selected from fluorine, optionally substituted C 1-6 alkyl, and optionally substituted C 6 aryl; and
(M n+ ) 1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2;
or a tautomer thereof.

20. A compound as defined in Formula I:

wherein,
R 1 and R 2 are CN;
R 3 is selected from —NHSO 2 R 4 , —NHSO 2 OR 4 , —SO 2 NHSO 2 R 4 , —SO 2 NHSO 2 OR 4 and an optionally substituted non-aromatic heterocycle having 5 or 6 cycle atoms linked through a nitrogen atom;
R 4 is selected from fluorine, optionally substituted C 1-6 alkyl, and optionally substituted C 6 aryl; and
(M n+ ) 1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2;
or a tautomer thereof.

21. An electrolyte composition or electrode material comprising a compound as defined in Formula I:

wherein,
R 1 and R 2 are independently selected from H, F, CN, NO 2 , and optionally substituted alkyl;
R 3 is selected from —NHSO 2 R 4 , —NHSO 2 OR 4 , —SO 2 NHSO 2 R 4 , —SO 2 NHSO 2 OR 4 and an optionally substituted non-aromatic heterocycle having 5 or 6 cycle atoms linked through a nitrogen atom;
R 4 is selected from fluorine, optionally substituted C 1-6 alkyl, and optionally substituted C 6 aryl; and
(M n+ ) 1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2;
or a tautomer thereof.

22. An electrochemical cell comprising an electrolyte, an electrode and a counter-electrode, wherein the electrolyte comprises the electrolyte composition as defined in claim 21 or at least one of the electrode or counter-electrode comprises the electrode material as defined in claim 21 .

Assignees

• Hydro Quebec
• Murata Manufacturing Co

Inventors

• Mallet Charlotte
• Rochon Sylviane
• Lafleur-Lambert Antoine
• Uesaka Shinichi
• Zaghib Karim

Classifications

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• H01M10/0569

  characterised by the solvents · CPC title

• H01M10/0567 Primary

  characterised by the additives · CPC title

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M4/62

  Selection of inactive substances as ingredients for active masses, e.g. binders, fillers · CPC title