Electrochromic materials

• US 8,154,787 B2
• Filed: 08/27/2010
• Issued: 04/10/2012
• Est. Priority Date: 06/25/2002
• Status: Active Grant

• Current Assignee: University of Washington
• Original Assignee: University of Washington
• Inventors: Liu, Lu, Xu, Chunye, Taya, Minoru
• Primary Examiner(s): Kopec, Mark
• Assistant Examiner(s): Ahvazi, Bijan
• Application Number:
  US12/870,482
• Publication Number:
  US 20100324306A1
• Time in Patent Office: 592 Days
• Field of Search: 359/240, 359/245, 359/265, 359/266, 359/267, 359/269, 359/273, 359/275, 502/353, 502/209, 528/424, 548/453, 549/23, 549/29, 549/50, 549/59
• US Class Current: 359/265
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08G 2261/1424 containing ether groups, including alkoxy
• CPC Class Codes: C08G 2261/3221 containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
• CPC Class Codes: C08G 2261/3223 containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
• CPC Class Codes: C08G 2261/3241 containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
• CPC Class Codes: C08G 2261/3243 containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
• CPC Class Codes: C08G 2261/44 Electrochemical polymerisation, i.e. oxidative or reductive coupling
• CPC Class Codes: C08G 2261/54 electrochromatic
• CPC Class Codes: C08G 61/122 derived from five- or six-membered heterocyclic compounds, other than imides
• CPC Class Codes: C08G 61/124 with a five-membered ring containing one nitrogen atom in the ring
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1408 Carbocyclic compounds
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/15165 Polymers
• CPC Class Codes: G02F 1/153 Constructional details
• CPC Class Codes: G02F 1/1533 structural features not otherwise provided for
• CPC Class Codes: G02F 1/163 : Operation of electrochromic cells, e.g. electrodeposition cells; Circuit arrangements therefor
• CPC Class Codes: G02F 2001/15145 : the electrochromic layer comprises a mixture of anodic and cathodic compounds

Abstract

Green electrochromic (EC) materials based on thiophene, and a green EC material based on pyrazine are disclosed. A first thiophene derivative (2,3-Di-thiophen-2-yl-thieno[3,4-b]pyrazine), which was previously investigated as a nonlinear optical material, is here disclosed for its use as an EC material and for its incorporation into an EC device. Synthesis of two new thiophene derivatives (2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene and 2,5-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene), and a new pyrazine derivative (2,3-dibenzyl-5,7-di(thien-2-yl) thieno[3,4-b]pyrazine) are also disclosed, since these materials are all able to selectively change state to appear a green color and can be polymerized to achieve a green EC polymer.

Claims

1. A method for making 2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoroethoxy)thiophene, comprising reacting 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)thiophene with a substituted thiophene.

2. The method of claim 1, wherein the substituted thiophene is 2-tributyltin thiophene.

3. The method of claim 1, wherein 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)thiophene is prepared from 3,4-bis-(2,2,2-trifluoroethoxy)thiophene.

4. The method of claim 3, wherein 3,4-bis-(2,2,2-trifluoroethoxy)thiophene is prepared from 3,4-bis-(2,2,2-trifluoroethoxy)thiophene-2,5-dicarboxylic acid.

5. The method of claim 4, wherein 3,4-bis-(2,2,2-trifluoroethoxy)thiophene-2,5-dicarboxylic acid is prepared from 3,4-bis-(2,2,2-trifluoroethoxy)thiophene-2,5-dicarboxylic acid dimethyl ester.

6. The method of claim 5, wherein 3,4-bis-(2,2,2-trifluoroethoxy)thiophene-2,5-dicarboxylic acid dimethyl ester is prepared from 3,4-dihydroxythiophene-2,5-dicarboxylic acid dimethyl ester.

7. The method of claim 1, further comprising purifying 2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoroethoxy)thiophene by chromatography.

8. A method for making 2,5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoroethoxy)thiophene, comprising reacting 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)thiophene with a substituted ethylenedioxyl thiophene.

9. The method of claim 8, wherein the substituted ethylenedioxyl thiophene is 2-tributyltin-3,4-ethylenedioxyl thiophene.