Poly(arylamine)s and uses thereof

Patent metadata

Field	Value
Publication number	US-11034796-B1
Application number	US-201615231368-A
Country	US
Kind code	B1
Filing date	Aug 8, 2016
Priority date	Aug 6, 2015
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Provided are poly(arylamine)s. The polymers can be redox active. The polymers can be used as electrode materials in, for example, electrochemical energy storage systems. The polymers can be made by electropolymerization on a conducting substrate (e.g., a current collector).

First claim

The invention claimed is:

1. A polymer comprising:

wherein
R 1 is independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons;
R 2 is independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons or an aryl group comprising 6 to 24 carbons;
L 1 is independently, at each occurrence in the polymer, an aryl moiety comprising 6 to 24 carbons, wherein the aryl moiety is completely aromatic or partially aromatic; or a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic;
L 2 is independently, at each occurrence in the polymer, an aliphatic moiety comprising 1 to 24 carbons; a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic; or a heteroalkyl branching moiety comprising one or more alkyl moiety comprising 1 to 24 carbons and one or more heteroatom; and
m is an integer from 1 to 20,000.

2. The polymer of claim 1 , wherein L 1 is:

wherein R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 ,and R 14 are individually at each occurrence in the polymer selected from hydrogen, alkyl groups comprising 1 to 6 carbons, halogen substituents, amines, ethers, and thioethers.

3. The polymer of claim 1 , wherein the alkyl moiety is:

wherein R 36 and R 37 are individually at each occurrence in the polymer selected from hydrogen, and an alkyl group comprising 1 to 6 carbons; and
e is an integer from 1 to 10.

4. The polymer of claim 1 , wherein at each occurrence in the polymer the heteroalkyl branching moiety comprises a secondary nitrogen or a tertiary nitrogen.

5. The polymer of claim 1 , wherein the heteroalkyl branching moiety is:

wherein x is individually at each occurrence in the polymer from 1 to 6;
y is individually at each occurrence in the polymer from 1 to 6; and
R 38 is individually at each occurrence in the polymer selected from an alkyl group, an aryl group, and covalent linkage to different heteroalkyl branching moiety in the polymer.

6. The polymer of claim 5 , wherein the polymer comprises one or more intrachain crosslink and/or one or more interchain crosslink.

7. The polymer of claim 1 , wherein L 1 is:

and

wherein f is an integer from 1 to 6.

8. An electrode comprising a film comprising a polymer having the following structure:

wherein
R 1 is independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons;
R 2 is independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons or an aryl group comprising 6 to 24 carbons;
L 1 is independently, at each occurrence in the polymer, an aryl moiety comprising 6 to 24 carbons, wherein the aryl moiety is completely aromatic or partially aromatic; or a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic;
L 2 is independently, at each occurrence in the polymer, an aliphatic moiety comprising 1 to 24 carbons, a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic; or a heteroalkyl branching moiety comprising one or more alkyl moiety comprising 1 to 24 carbons and one or more heteroatom; and
m is an integer from 1 to 20,000.

9. The electrode of claim 8 , wherein the film is disposed on at least a portion of a substrate.

10. The electrode of claim 9 , wherein the polymer is electropolymerized on the substrate.

11. The electrode of claim 10 , wherein the substrate is a current collector.

12. A device comprising an electrode of claim 8 .

13. The device of claim 12 , wherein the device is an electrochemical energy storage (EES) system.

14. The device of claim 13 , wherein the EES is a battery.

15. The device of claim 13 , wherein the EES is a capacitor or battery-capacitor hybrid.

16. A capacitor or battery-capacitor hybrid comprising an electrode comprising a film comprising a polymer comprising:

wherein
R 1 and R 2 are is independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons or an aryl group comprising 6 to 24 carbons;
L 1 is:

 and
L 2 is:

wherein f is an integer from 1 to 6; and
n is an integer from 1 to 20,000
or
ii)

 (Structure II),
wherein
R 1 and R 2 are independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons or an aryl group comprising 6 to 24 carbons;
L 1 is independently, at each occurrence in the polymer, an aryl moiety comprising 6 to 24 carbons, wherein the aryl moiety is completely aromatic or partially aromatic; or a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic;
L 2 is independently, at each occurrence in the polymer, an aliphatic moiety comprising 1 to 24 carbons; an aryl moiety comprising 6 to 24 carbons, wherein the aryl moiety is completely aromatic or partially aromatic; a heteroaryl moiety comprising 6 to 24 carbons, wherein the heteroaryl moiety is completely aromatic or partially aromatic; or a heteroalkyl branching moiety comprising one or more alkyl moiety comprising 1 to 24 carbons and one or more heteroatom; and
m is an integer from 1 to 20,000.

17. The capacitor or battery-capacitor hybrid of claim 16 , wherein the film is disposed on at least a portion of a substrate.

18. The capacitor or battery-capacitor hybrid of claim 17 , wherein the polymer is electropolymerized on the substrate.

19. The capacitor or battery-capacitor hybrid of claim 18 , wherein the substrate is a current collector.

20. A polymer comprising:

wherein
m is 1 to 20,000;
R 1 and R 2 are independently, at each occurrence in the polymer, an alkyl group comprising 1 to 6 carbons or an aryl group comprising 6 to 24 carbons;
L 1 is:

 and
L 2 is:

Assignees

• Univ Cornell

Inventors

• Truong Thanh-Tam
• Abruna Hector D
• Coates Geoffrey W
• Fors Brett P

Classifications

• H01M4/606

  containing aromatic main chain polymers · CPC title

• H01M4/137

  Electrodes based on electro-active polymers · CPC title

• H01G11/48

  Conductive polymers · CPC title

• H01G11/04

  Hybrid capacitors · CPC title

• C08G73/0633

  with only two nitrogen atoms in the ring · CPC title