Electrochromic compounds with improved color stability in their radical states

Patent metadata

Field	Value
Publication number	US-10040763-B2
Application number	US-201615040946-A
Country	US
Kind code	B2
Filing date	Feb 10, 2016
Priority date	Feb 11, 2015
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

The invention relates to an electrochromic device and uses thereof, wherein the electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes represented by Formula (I):

First claim

What is claimed is:

1. An electrochromic device comprising:
a non-dimerizing electrochromic compound represented by Formula (I):

wherein:
R 1 and R 2 are individually alkyl, siloxyalkyl, hydroxyalkyl, alkenyl, or aralkyl;
R 4 , R 6 , R 8 , and R 10 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl;
R 3 and R 5 are individually secondary alkyl, tertiary alkyl, or a group of Formula (II):

wherein:
R 11 , R 12 , R 13 , and R 14 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , or alkyl;
R 15 is OH, F, Cl, Br, I, CN, NO 2 , —OC(O)NR 16 R 17 , Et, Pr, iso-propyl, butyl, sec-butyl, tert-butyl, alkoxy, or OC(O)NH(CH 2 ) n COOH;
R 16 is H or alkyl; and
R 17 is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, or —(CH 2 ) n Si(OR 18 ) 3 ;
R 18 is H or alkyl; and
n is 1 to 10;

R 7 and R 9 are H;
R 20 is H or alkyl; and
X is an anion.

2. The electrochromic device of claim 1 , wherein R 11 , R 12 , R 13 , and R 14 are individually H or alkyl.

3. The electrochromic device of claim 1 , wherein R 11 , R 12 , R 13 , and R 14 are H, and R 15 is methoxy, ethoxy, propoxy, ethyl, propyl, iso-propyl, butyl, sec-butyl, or tert-butyl.

4. The electrochromic device of claim 1 , wherein R 17 is alkyl or siloxy alkyl.

5. The electrochromic device of claim 1 , wherein R 1 and R 2 are individually aralkyl, C 1 -C 12 alkyl or C 1 -C 12 hydroxyalkyl.

6. An electrochromic device comprising:
a non-dimerizing electrochromic compound represented by Formula (III):

wherein:
R 1 and R 2 are individually alkyl, siloxyalkyl, hydroxyalkyl, alkenyl, or aralkyl;
R 4 , R 6 , R 8 , and R 10 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl;
R 3 and R 5 are individually secondary alkyl, tertiary alkyl, or a group of Formula (II):

wherein:
R 11 , R 12 , R 13 , and R 14 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , or alkyl;

R 15 is OH, F, Cl, Br, I, CN, NO 2 , —OC(O)NR 16 R 17 , Et, Pr, iso-propyl, butyl, sec-butyl, tert-butyl, alkoxy, or OC(O)NH(CH 2 ) n COOH;
R 16 is H or alkyl; and
R 17 is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, or —(CH 2 ) n Si(OR 18 ) 3 ;
R 18 is H or alkyl; and
n is 1 to 10;

R 7 and R 9 are H;
R 19 is (CH 2 ) n′ or arylene, and n′ is from 1 to 12;
R 20 is H or alkyl; and
X is an anion.

7. The electrochromic device of claim 6 , wherein R 19 is (CH 2 ) 3-8 or 1,4-phenylene.

8. The electrochromic device of claim 1 , wherein R 4 , R 6 , R 8 , and R 10 are individually H, OH, or alkyl.

9. The electrochromic device of claim 1 , wherein X − is F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N(CN) 2 − , N(CF 3 SO 2 ) 2 − , C(CF 3 SO 2 ) 3 − , N(SO 2 C 2 F 5 ) 2 − , − Al(OC(CF 3 ) 3 ) 4 or − BAr 4 , wherein Ar is a aryl or fluorinated aryl group.

10. The electrochromic device of claim 1 further comprising:
an electrochromic medium comprising the non-dimerizing electrochromic compound; and
a chamber defined by a first conductive surface of first substrate, a second conductive surface of a second substrate, and a sealing member joining the first substrate to the second substrate,
wherein the electrochromic medium is disposed within the chamber.

11. The electrochromic device of claim 10 further comprising an anodic component and a solvent.

12. The electrochromic device of claim 1 , wherein R 3 and R 5 are each a group of Formula (II) and R 15 is —OC(O)NR 16 R 17 .

13. The electrochromic device of claim 1 , wherein R 15 is OC(O)NH(CH 2 )—Si(OEt) 3 .

14. The electrochromic device of claim 1 , wherein R 3 and R 5 are each a group of Formula (II) and R 15 is OC(O)NH(CH 2 ) n Si(OEt) 3 .

Assignees

• Gentex Corp

Inventors

• Lin Rongguang
• Baumann Kelvin L
• Giri Punam
• Nemes Joel C
• Kloeppner Leroy J
• Theiste David A

Classifications

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C07F17/02

  of metals of Groups 8, 9 or 10 of the Periodic Table · CPC title

• C07D213/04

  having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom · CPC title

• C08G61/122

  derived from five- or six-membered heterocyclic compounds, other than imides · CPC title

• C07F9/58

  Pyridine rings · CPC title