Multicolored electrochromic polymer compositions and methods of making and using the same

• US 9,975,989 B2
• Filed: 01/06/2017
• Issued: 05/22/2018
• Est. Priority Date: 05/04/2016
• Status: Active Grant

• Current Assignee: Lannray Advanced Materials Company Limited
• Original Assignee: Furcifer, Inc.
• Inventors: Mei, Jianguo, Zhou, Yan
• Primary Examiner(s): Fang, Shane
• Application Number:
  US15/399,839
• Publication Number:
  US 20170321002A1
• Time in Patent Office: 501 Days
• CPC Class Codes: C08G 2261/124 alternating
• CPC Class Codes: C08G 2261/1424 containing ether groups, including alkoxy
• CPC Class Codes: C08G 2261/18 conjugated
• CPC Class Codes: C08G 2261/19 partially conjugated
• CPC Class Codes: C08G 2261/228 Polymers, i.e. more than 10 repeat units
• CPC Class Codes: C08G 2261/312 Non-condensed aromatic systems, e.g. benzene
• CPC Class Codes: C08G 2261/3246 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: C08G 2261/3247 containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur
• CPC Class Codes: C08G 2261/3327 alkene-based
• CPC Class Codes: C08G 2261/364 containing hetero atoms
• CPC Class Codes: C08G 2261/419 Acyclic diene metathesis [ADMET]
• CPC Class Codes: C08G 2261/54 electrochromatic
• CPC Class Codes: C08G 61/123 derived from five-membered heterocyclic compounds
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C09K 2211/1475 containing nitrogen and oxygen as heteroatoms
• CPC Class Codes: C09K 2211/1483 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: C09K 2211/1491 containing other combinations of heteroatoms
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials

Abstract

This disclosure relates generally to electrochromic polymers that include a plurality of π-conjugated chromophores in spaced relation with one another, and a plurality of conjugation-break spacers (CBSs), where at least one CBS separates adjacent chromophores. The chromophores may be colored in the neutral state, and multicolored to transmissive in different oxidization states.

Claims

1. An electrochromic polymer, comprising:

a plurality of π

-conjugated chromophores in spaced relation with one another, wherein each π

-conjugated chromophore is colored in a neutral state, and is colored or transmissive in an oxidized state; and

a plurality of conjugation-break spacers (CBSs), wherein at least one CBS separates adjacent π

-conjugated chromophores,

wherein at least one of the plurality of π

-conjugated chromophores comprises at least one optionally substituted 3,4-propylenedioxythiophene moiety, at least one optionally substituted benzene moiety, or at least one optionally substituted benzo[c][1,2,5]thiadiazole moiety, or combinations thereof.

2. The electrochromic polymer of claim 1, wherein at least one CBS comprises:

3. The electrochromic polymer of claim 1, wherein at least two of the CBSs have the same structure as one another.

4. The electrochromic polymer of claim 1, wherein at least two of the CBSs have a different structure from one another.

5. The electrochromic polymer of claim 1, wherein the at least one of the plurality of π

-conjugated chromophores comprises a structure of Formula (I);

6. The electrochromic polymer of claim 1, wherein the at least one of the plurality of π

-conjugated chromophores comprises a structure of Formula (II);

7. The electrochromic polymer of claim 1, wherein the at least one of the plurality of π

-conjugated chromophores comprises a structure of Formula (III);

8. The electrochromic polymer of claim 1, wherein at least two of the π

-conjugated chromophores have different structures from one another.

9. The electrochromic polymer of claim 1, wherein at least two of the π

-conjugated chromophores exhibit different colors relative to one another in the neutral states thereof.

10. The electrochromic polymer of claim 1, wherein the at least one of the plurality of π

-conjugated chromophores comprises the at least one optionally substituted 3,4-propylenedioxythiophene moiety, and the at least one optionally substituted benzene moiety or the at least one optionally substituted benzo[c][1,2,5]thiadiazole moiety.

11. The electrochromic polymer of claim 1, wherein the at least one of the plurality of π

-conjugated chromophores comprises the at least one optionally substituted 3,4-propylenedioxythiophene moiety, and at least another one of the plurality of π

-conjugated chromophores comprises the at least one optionally substituted benzene moiety or the at least one optionally substituted benzo[c][1,2,5]thiadiazole moiety.