Electrochromic monomers and polymers for a switchable window

• US 7,505,191 B2
• Filed: 07/06/2007
• Issued: 03/17/2009
• Est. Priority Date: 06/25/2001
• Status: Expired due to Term

• Current Assignee: University of Washington
• Original Assignee: University of Washington
• Inventors: Legenski, Susan E., Taya, Minoru, Xu, Chunye, Liu, Lu
• Primary Examiner(s): Stultz; Jessica T
• Application Number:
  US11/774,438
• Publication Number:
  US 20070268550A1
• Time in Patent Office: 620 Days
• Field of Search: 359/273
• US Class Current: 359/273
• 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 2261/44 Electrochemical polymerisation, i.e. oxidative or reductive coupling
• CPC Class Codes: C08G 2261/54 electrochromatic
• 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 2211/1408 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

Syntheses of a new blue EC monomer (ProDOT-MePro), and a new red EC monomer (ProDOP-Et2) are described. Two additional new types of EC monomers based on 3,4-alkylenedioxythiophene include fluorinated EC monomers and an EC monomer including silicon. EC polymer devices having more than one different color EC polymer to enable additional colors to be provided using subtractive color mixing are also described, as well as EC polymer devices incorporating a logo, image, or text, are generally obscured when the device is colored, but become visible when the device is not colored. Also described are EC polymer devices that include a cathodic EC polymer layer, a gel electrolyte, a counter electrode, and a reference electrode. Working prototypes of such devices exhibit significant increases in the speed of transition of the EC device from a colored state to a transparent state.

Claims

1. An electrochromic monomer having a formula selected from the group consisting essentially of:

(a) 3-methyl-3′

-propyl-3,4-dihydro-2H-thieno(3,4-b)(1,4)dioxepine;

(b) 3,3-diethyl-3,4-dihydro-2H,7H-(1,4)dioxepino(2,3-c)pyrrole;

(c) 3,4-bis-R-thiophene, wherein R comprises one of;

(i) 2,2,2-trifluoro-ethoxy;

(ii) 2-fluoro-ethoxy;

(iii) 2,3,4,5,6, pentafluorobenzoxy; and

(iii) 2,2-difluoro-1-3-propoxy; and

(d) 6,6-dimethyl-6,7-dihydro-5H-4,8-dioxa-2-thia-6-sila-azulene.

2. An electrochromic polymer having a formula selected from the group consisting essentially of:

(a) poly[3-methyl-3′

-propyl-3,4-dihydro-2H-thieno(3,4-b)(1,4)dioxepine], such an electrochromic polymer exhibiting a blue color in at least one state; and

(b) poly[3,3-diethyl-3,4-dihydro-2H,7H-(1,4)dioxepino(2,3-c)pyrrole], such an electrochromic polymer exhibiting a red color in at least one state.

3. An electrochromic monomer having the formula 3-methyl-3′

-propyl-3,4-dihydro-2H-thieno(3,4-b)(1,4)dioxepine.

4. A blue electrochromic polymer having the formula poly[3-methyl-3′

-propyl-3,4-dihydro-2H-thieno(3,4-b)(1,4)dioxepine].

5. An electrochromic monomer having the formula 3,3-diethyl-3,4-dihydro-2H,7H-(1,4)dioxepino(2,3-c)pyrrole.

6. A red electrochromic polymer having the formula poly[3,3-diethyl-3,4-dihydro-2H,7H-(1,4)dioxepino(2,3-c)pyrrole].

7. An electrochromic monomer having the formula 3,4-bis-R-thiophene, wherein R comprises one of:

(a) 2,2,2-trifluoro-ethoxy;

(b) 2-fluoro-ethoxy;

(c) 2,3,4,5,6, pentafluorobenzoxy; and

(d) 2,2-difluoro-1-3-propoxy.

8. An electrochromic monomer having the formula 6,6-dimethy-6,7-dihydro-5H-4,8-dioxa-2-thia-6-sila-azulene.