Granted Patent B2

US 12,421,392 · App. 17/451,628 · Granted Sep 23, 2025

Inventors: Lihui Wang (Berkeley, CA); Ziyang Huo (Moraga, CA); Chengtian Shen (Irvine, CA)

Assignee: Twelve Benefit Corporation

C08L101/02C08G10/00C08G61/02C25B9/23C25B13/08C08G2261/143C08G2261/146C08G2261/312C08G2261/3142C08G2261/45C08G2261/516H01M8/103H01M8/1039H01M2008/1095

Abstract

Claims (42)

1. A composition comprising a first structure and a second structure, wherein:

(i) the first structure comprises:

or a salt thereof, wherein:

 each of R 7′ and R 8′ is, independently, an electron-withdrawing moiety, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, or optionally substituted arylalkylene, wherein at least one of R 7′ or R 8′ comprises the electron-withdrawing moiety or wherein R 7′ and R 8′ can be taken together to form an optionally substituted cyclic group;

each of R 9′ and R 10′ is, independently, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, or optionally substituted arylalkylene, or wherein R 9′ and R 10′ can be taken together to form an optionally substituted cyclic group;

Ar comprises or is an optionally substituted aromatic or optionally substituted arylene;

n is an integer of 1 or more; and

each of ring a 1 , ring b 1 , and/or ring c 1 can be optionally substituted;

wherein one or more of ring a 1 , ring b 1 , ring c 1 , R 7′ , R 8′ , R 9′ , and R 10′ comprises an ionizable moiety or an ionic moiety; and

(ii) the second structure comprises:

or a salt thereof, wherein:

 each of R 9 and R 10 is, independently, an electron-withdrawing moiety, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, optionally substituted aryloxy, or optionally substituted arylalkylene, wherein R 9 and R 10 can be taken together to form an optionally substituted cyclic group;

m is an integer of 1 or more;

q is 0, 1, 2, or more;

each of rings a, b, and c is optionally substituted; and

wherein one or more of rings a, b, and c and R 9 and R 10 optionally comprises an ionizable moiety or an ionic moiety.

2. The composition of claim 1 , wherein the electron-withdrawing moiety of at least one of the first structure and the second structure is an optionally substituted haloalkyl, cyano, phosphate, sulfate, sulfonic acid, sulfonyl, difluoroboranyl, borono, thiocyanato, or piperidinium.

3. The composition of claim 1 , wherein R 7′ is the electron-withdrawing moiety and R 8′ comprises the ionizable moiety or the ionic moiety.

4. The composition of claim 1 , wherein the second structure comprises the ionizable moiety or h ionic moiety.

5. The composition of claim 4 , wherein at least one of rings a, b, and c comprises h ionizable moiety or h ionic moiety.

6. The composition of claim 1 , wherein the ionizable moiety or the ionic moiety of at least one of the first structure and the second structure comprises -L A -X A or -L A -(L A′ -X A ) L2 or -L A -(X A -L A′ -X A′ ) L2 or -L A -X A -L A′ -X A′ or -L A -X A -L A′ -X A′ -L A″ -X A″ wherein:

each L A , L A′ , and L A″ is a linking moiety;

each X A , X A′ , and X A″ comprises, independently, an acidic moiety, a basic moiety, or a multi-ionic moiety; and

L2 is an integer of 1 or more.

7. The composition of claim 6 , wherein each L A , L A′ , and L A″ comprises, independently, an optionally substituted alkylene, optionally substituted alkyleneoxy, optionally substituted heteroalkylene, optionally substituted arylene, and/or optionally substituted aryleneoxy.

8. The composition of claim 6 , wherein each X A , X A′ , and X A″ comprises, independently, sulfo, sulfonate anion, sulfonium cation, carboxy, carboxylate anion, phosphono, phosphonate anion, phosphonium cation, phosphazenium cation, amino, ammonium cation, heterocyclic cation, piperidinium cation, azepanium cation, or a salt form thereof.

9. The composition of claim 1 , wherein the optionally substituted arylene of the first structure, the optionally substituted ring a 1 , ring b 1 , and/or ring c 1 of the first structure, or the optionally substituted ring a, b, and/or c of the second structure is substituted with one or more substituents, and wherein each substituent of the one or more substituents is selected from the group consisting of alkyl, alkoxy, alkoxyalkyl, amino, aminoalkyl, aryl, arylalkylene, aryloyl, aryloxy, arylalkoxy, cyano, hydroxy, hydroxyalkyl, nitro, halo, and haloalkyl.

10. The composition of claim 1 , wherein the composition comprises a polymer or a copolymer.

11. The composition of claim 1 , wherein the composition comprises a film, a membrane, or a cross-linked polymeric matrix.

12. An electrochemical cell comprising:

an anode;

a cathode; and

a polymer electrolyte membrane disposed between the anode and the cathode, wherein the polymer electrolyte membrane comprises a composition of claim 1 .

13. The composition of claim 1 , wherein R 8′ in the first structure comprises the ionizable moiety or the ionic moiety.

14. The composition of claim 1 , wherein the first structure comprises Formula (III), Formula (IV), or a salt thereof.

15. The composition of claim 1 , wherein the ionizable moiety or the ionic moiety of at least one of the first structure and the second structure comprises an ammonium moiety.

16. The composition of claim 1 , wherein ring a, ring b, ring c, R 9 , or R 10 of the second structure comprises the ionizable moiety or the ionic moiety.

17. The composition of claim 1 , wherein at least one of R 9 and R 10 of the second structure is an optionally substituted aliphatic or an optionally substituted heteroaliphatic.

18. The composition of claim 1 , wherein at least one of R 9 and R 10 of the second structure is an optionally substituted alkyl or an optionally substituted heteroalkyl.

19. The composition of claim 1 , wherein the ionizable moiety or the ionic moiety of at least one of the first structure and the second structure comprises, independently, sulfo, sulfonate anion, sulfonium cation, carboxy, carboxylate anion, phosphono, phosphonate anion, phosphonium cation, phosphazenium cation, amino, ammonium cation, heterocyclic cation, piperidinium cation, azepanium cation, or a salt form thereof.

20. The composition of claim 1 , wherein the ionizable moiety or the ionic moiety of at least one of the first structure and the second structure comprises a piperidinium moiety.

21. The composition of claim 1 , wherein the ionizable moiety or the ionic moiety of at least one of the first structure and the second structure comprises an azepanium moiety.

Assignments (4)

Continuity (2)

References Cited (400)