Sulfonimide salts for battery applications

Patent metadata

Field	Value
Publication number	US-12199239-B2
Application number	US-202318159825-A
Country	US
Kind code	B2
Filing date	Jan 26, 2023
Priority date	Jan 20, 2017
Publication date	Jan 14, 2025
Grant date	Jan 14, 2025

Abstract

A class of sulfonimide salts for solid-state electrolytes can be synthesized based on successive S N Ar reactions of fluorinated phenyl sulfonimides: Fluorinated Aryl Sulfonimide Tags (FAST). The chemical and electrochemical oxidative stability of these FAST salts as well as other properties like solubility, Lewis basicity, and conductivity can be tuned by introducing different numbers and types of nucleophilic functional groups to the FAST salt scaffold.

First claim

What is claimed is:

1. A composition comprising:

wherein R 1 is —CF 3 or a fluorinated phenyl and R 2 is a fluorinated phenyl or R 3 is —CF 3 or a fluorinated phenyl and R 4 is a fluorinated phenyl, wherein at least one of R 3 and R 4 is substituted by an alkoxide or an amine
wherein R 3 is—CF 3 or a fluorinated phenyl and R 4 is a fluorinated phenyl, wherein at least one of R 3 and R 4 is substituted by a nucleophile
wherein the fluorinated phenyl has a formula

wherein each of X 1 , X 3 , and X 5 , independently, is methoxy, ethoxy, propoxy, butoxy, pentoxy, phenoxy, piperidinyl, or cycloocteneamino.

2. The composition of claim 1 , wherein R 1 is —CF 3 .

3. The composition of claim 1 , wherein R 1 is a fluorinated phenyl.

4. The composition of claim 3 , wherein the fluorinated phenyl has at least two fluorine groups.

5. The composition of claim 3 , wherein the fluorinated phenyl has a formula

wherein each of X 1 , X 2 , X 3 , X 4 , and X 5 , independently, is F or CF 3 .

6. The composition of claim 3 , wherein the fluorinated phenyl has a formula

7. The composition of claim 1 , wherein the fluorinated phenyl has a formula

wherein each of X 1 , X 2 , X 3 , X 4 , and X 5 , independently, is F, OR a , or NR c R d , wherein R a is C1-C6 alkyl, benzalkyl, or substituted or unsubstituted phenyl, R b is C1-C6 alkyl, benzalkyl, or phenyl, R c is C1-C6 alkyl, benzalkyl, or phenyl, or R b and R c together form a three to eight membered ring.

8. The composition of claim 1 , wherein the compound has formula (I) or formula (II)
P-Pip x OR y F z   (I)

P-Pip x OPh w F z   (II)

wherein P is a perfluoroarylsulfonimide anion, Pip is a piperidine, OR is an alkoxide, F is a fluorine substituent, OPh is phenoxide, and each of x, y, z and w, independently, is 0, 1, 2 or 3, wherein the sum of x, y, and z or x, z and w is 0, 1, 2 or 3.

9. The composition of claim 8 , wherein OR is methoxy, ethoxy, isopropoxy or neopentoxy.

10. An energy storage device comprising an electrolyte including a composition of claim 1 .

11. The energy storage device of claim 10 , wherein the compound has formula (I) or formula (II)
P-Pip x OR y F z   (I)

P-Pip x OPh w F z   (II)

wherein P is a perfluoroarylsulfonimide anion, Pip is a piperidine, OR is methoxy, ethoxy, isopropoxy or neopentoxy, F is a fluorine substituent, OPh is phenoxide, and each of x, y, z and w, independently, is 0, 1, 2 or 3, wherein the sum of x, y, and z or x, z and w is 0, 1, 2 or 3.

12. The energy storage device of claim 11 , wherein OR is methoxy, ethoxy, isopropoxy or neopentoxy.

Assignees

• Massachusetts Inst Technology
• Samsung Electronics Co Ltd

Inventors

• Johnson Jeremiah Allen
• Shao-Horn Yang
• Anandakathir Robinson
• Chen Mao
• Feng Shuting
• Giordano Livia
• Huang Mingjun
• Zhang Wenxu

Classifications

• C07C311/48

  having nitrogen atoms of sulfonamide groups further bound to another hetero atom · CPC title

• H01M10/052

  Li-accumulators · CPC title

• C07C311/15

  Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings · CPC title

• H01M2300/0082

  Organic polymers · CPC title

• H01M2300/0025

  Organic electrolyte · CPC title