Green electrochromic materials

• US 7,808,691 B2
• Filed: 10/22/2007
• Issued: 10/05/2010
• Est. Priority Date: 06/25/2002
• Status: Active Grant

• Current Assignee: University of Washington
• Original Assignee: University of Washington
• Inventors: Taya, Minoru, Xu, Chunye, Liu, Lu
• Primary Examiner(s): Stultz; Jessica T
• Application Number:
  US11/876,513
• Publication Number:
  US 20090067030A1
• Time in Patent Office: 1,079 Days
• Field of Search: 359/265
• 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. An electrochromic device comprising:

(a) a transparent electrode;

(b) an electrochromic organic material that in a first state is not green and in a second state exhibits a green color, the electrochromic organic material exhibiting a single absorbance band, wherein the green electrochromic organic material exhibiting a single absorbance band comprises an electrochromic polymer based on a fluorinated derivative of 2,5-(2,3-dihydro- thieno[3,4][1,4]-dioxin-5-yl)-3,4-dihydroxy-thiophene, the fluorinated derivative corresponding to 2,5-(2,3-dihydro-thieno[3,4][1,4]-dioxin-5-yl)-3,4-di(R-oxy)-thiophene, with R corresponding to a fluorinated functional group; and

(c) an electrolyte.