Electrochromic material, method for preparing the same and component comprising the same

Patent metadata

Field	Value
Publication number	US-9481825-B2
Application number	US-201414424214-A
Country	US
Kind code	B2
Filing date	Apr 30, 2014
Priority date	Sep 29, 2013
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

The present invention relates to a polythiophene electrochromic material, which is a copolymer of [3,4-bis(2-ethylhexyloxy)thiophene]-thiophene-[3,4-dimethoxy thiophene] represented by Formula I:

wherein, 0<n≦0.5m, 0<q<m. The copolymer film has changeable colors reversibly varying between red and transparent, cycle life of more than 10,000. It has many advantages, such as low driving voltage, being transparent in the oxidation state with high transmittance, short response time, and being suitable for spray coating operation and the like, thus it has broad application prospect in the devices of electrochromic windows, electrochromic displays and the like.

First claim

The invention claimed is:

1. A polythiophene electrochromic material, which is a copolymer of [3,4-bis(2-ethylhexyloxy)thiophene]thiophene-[3,4-dimethoxy thiophene] represented by Formula I:

wherein, 0<n≦0.5m, 0<q<m.

2. The polythiophene electrochromic material according to claim 1 , wherein 0.4m<n≦0.5m, 0.4m<q<0.5m.

3. The polythiophene electrochromic material according to claim 1 , wherein the copolymer has a number average molecular weight in the range of 3.0×10 4 g/mol to 5.5×10 4 g/mol.

4. A method for preparing a polythiophene electrochromic material, wherein the polythiophene electrochromic material is a copolymer of [3,4-bis(2-ethylhexyloxy)thiophene]-thiophene-[3,4-dimethoxy thiophene] represented by Formula I:

wherein, 0<n≦0.5m, 0<q<m; and
the method comprising:
Step 1: 3,4-dimethoxy thiophene reacting with 2-ethyl hexanol under the catalysis of the transetherification catalyst, to obtain 3,4-bis(2-ethylhexyloxy)thiophene; and
Step 2: 3,4-bis(2-ethylhexyloxy)thiophene, thiophene and 3,4-dimethoxy thiophene being subjected to an oxidation polymerization reaction under the oxidation of an oxidant, to obtain the copolymer of [3,4-bis(2-ethylhexyloxy)thiophene]thiophene-[3,4-dimethoxy thiophene] represented by Formula I.

5. The method according to claim 4 , wherein, in the Step 1, the catalyst for transetherification reaction is p-toluenesulfonic acid, and the reaction solvent is toluene.

6. The method according to claim 4 , wherein the feeding molar ratio of 3,4-dimethoxy thiophene and 2-ethylhexanol is 1:4 to 1:6, and the feeding molar ratio of the catalyst and 3,4-dimethoxy thiophene is 1:10 to 1:15.

7. The method according to claim 4 , wherein, in the Step 1, the reaction time is 24 to 48 hours, and the reaction temperature is 110° C. to 130° C.

8. The method according to claim 4 , wherein, in the Step 2, the oxidant is anhydrous ferric chloride, and the reaction solvent is selected from ethyl acetate, chloroform or nitromethane.

9. The method according to claim 4 , wherein, in the Step 2, the molar amounts of 3,4-bis(2-ethylhexyloxy)thiophene, thiophene and 3,4-dimethoxy thiophene are represented respectively by m, n and q which satisfies the following relationship: 0<n≦0.5m, 0<q<m, and the amount of the oxidant of anhydrous ferric chloride is 5 to 6 times of the total amount of the three monomers of 3,4-bis(2-ethylhexyloxy)thiophene, thiophene and 3,4-dimethoxy thiophene.

10. The method according to claim 4 , wherein, in the Step 2, the reaction time is 24 to 72 hours, and the reaction temperature is 10° C. to 35° C.

11. A component, comprising a polythiophene electrochromic material which is a copolymer of [3,4-bis(2-ethylhexyloxy)thiophene]-thiophene-[3,4-dimethoxy thiophene] represented by Formula I:

wherein, 0<n≦0.5m, 0<q<m.

12. The component according to claim 11 , wherein the component is an electrochromic film.

13. The component according to claim 12 , wherein the electrochromic film is prepared by a method comprising:
preparing the dichloromethane solution the electrochromic material, and
spraying the of the electrochromic material onto the surface of an ITO glass or a FTO glass with a spray coating apparatus.

Assignees

• Boe Technology Group Co Ltd
• Univ Science & Tech China

Inventors

• Xu Chunye
• Chen Xiaoming

Classifications

• C08F228/06

  by a heterocyclic ring containing sulfur · CPC title

• C08G2261/43

  Chemical oxidative coupling reactions, e.g. with FeCl3 · CPC title

• C08G2261/1424

  containing ether groups, including alkoxy · CPC title

• C08G2261/54

  electrochromatic · CPC title

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title