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

• US 10,544,257 B2
• Filed: 04/27/2018
• Issued: 01/28/2020
• 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:
  US15/965,483
• Publication Number:
  US 20180244839A1
• Time in Patent Office: 641 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

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, are provided. The chromophores may be colored in the neutral state, and multicolored to transmissive in different oxidation states.

Claims

1. A method for preparing at least a portion of an electrochromic polymer, the method comprising:

combining three or more monomer units in a solvent, wherein the three or more monomer units comprise complementary reactive functional groups; and

cross-coupling the three or more monomer units to yield a π

-conjugated copolymer sequence;

wherein at least one of the three or more monomer units has a structure of Formula (XIII);

2. The method of claim 1, comprising adding a catalyst to the solvent, wherein the catalyst comprises a palladium compound.

3. The method of claim 1, wherein at least one of the three or more monomer units has a structure of Formula (IX) or (X):

4. The method of claim 1, wherein the π

-conjugated copolymer sequence comprises;

5. The method of claim 1, wherein the π

-conjugated copolymer sequence comprises;

6. The method of claim 1, wherein the π

-conjugated copolymer sequence comprises;

7. The method of claim 1, wherein the π

-conjugated copolymer sequence has at least two π

-conjugated chromophores having different structures from one another.

8. The method of claim 1, wherein the π

-conjugated copolymer sequence has at least two π

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

9. A method for preparing at least a portion of an electrochromic polymer, the method comprising:

combining three or more monomer units in a solvent, wherein the three or more monomer units comprise complementary reactive functional groups; and

cross-coupling the three or more monomer units to yield a π

-conjugated copolymer sequence;

wherein at least one of the three or more monomer units includes a non-conjugated linking segment, wherein the linking segment is;