Electrochromic compounds with improved color stability in their radical states

Patent metadata

Field	Value
Publication number	US-10464900-B2
Application number	US-201815997358-A
Country	US
Kind code	B2
Filing date	Jun 4, 2018
Priority date	Feb 11, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

An electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes, the electrochromic 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 alkylcarboxylate, alkylammonium, alkylphosphonate, —(CH 2 ) n Si(OH) 3 , —(CH 2 ) n Si(OMe) 3 , —(CH 2 ) n Si(OEt) 3 ,

 —(CH 2 ) n CH═CH 2 , —(CH 2 ) n OC(O)CH═CH 2 , or —(CH 2 ) n OC(O)C(CH 3 )═CH 2 ;
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 , R 5 , R 7 , and R 9 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl;
R 20 is H or alkyl;
n is 1-12; and
X is an anion;
with the proviso that R 3 and R 5 or R 7 and R 9 are individually secondary alkyl, tertiary alkyl, or aryl.

2. The electrochromic device of claim 1 , wherein R 3 , R 5 , R 7 , and R 9 are individually secondary alkyl, tertiary alkyl, or aryl.

3. The electrochromic device of claim 1 , wherein R 3 and R 5 are individually aryl.

4. The electrochromic device of claim 3 , wherein the aryl is 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 H, OH, F, Cl, Br, I, CN, NO 2 , —OC(O)NR 16 R 17 , alkyl, or alkoxy;
R 16 is H or alkyl;
R 17 is H, alkyl, or siloxy alkyl; and
R 20 is H or alkyl.

5. The electrochromic device of claim 4 , wherein R 11 , R 12 , R 13 , and R 14 are individually H or alkyl.

6. The electrochromic device of claim 4 , wherein R 11 , R 12 , R 13 , and R 14 are H, and R 15 is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, or tert-butyl.

7. The electrochromic device of claim 4 , wherein 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.

8. The electrochromic device of claim 1 , wherein R 3 and R 5 are aryl and R 7 and R 9 are H.

9. The electrochromic device of claim 3 , wherein the aryl is 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 , ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, alkoxy, or OC(O)NH(CH 2 ) n COOH;
R 16 is H or alkyl;
R 17 is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, or —(CH 2 ) n Si(OR 18 ) 3 ;
n is 1 to 10;
R 7 and R 9 are H; and
R 18 is H or alkyl; and
R 20 is H or alkyl.

10. The electrochromic device of claim 9 , wherein R 11 , R 12 , R 13 , and R 14 are individually H or alkyl.

11. The electrochromic device of claim 9 , 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.

12. The electrochromic device of claim 1 , wherein R 1 and R 2 are individually,

—(CH 2 ) n CH═CH 2 , —(CH 2 ) n OC(O)CH═CH 2 , or —(CH 2 ) n OC(O)C(CH 3 )═CH 2 .

13. The electrochromic device of claim 9 , wherein R 1 and R 2 are individually —(CH 2 ) n Si(OH) 3 , —(CH 2 ) n Si(OMe) 3 , —(CH 2 ) n Si(OEt) 3 ,

, —(CH 2 ) n CH═CH 2 , —(CH 2 ) n OC(O)CH═CH 2 , or —(CH 2 ) n OC(O)C(CH 3 )═CH 2 .

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

15. 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.

16. The electrochromic device of claim 1 further comprising:
an electrochromic medium comprising the non-dimerizing electrochromic compound, an anodic component, and a solvent; 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.

17. A compound represented by Formula (I):

wherein:
R 1 and R 2 are individually —(CH 2 ) n Si(OH) 3 , —(CH 2 ) n Si(OMe) 3 , —(CH 2 ) n Si(OEt) 3 ,

 (CH 2 ) n CH═CH 2 , —(CH 2 ) n OC(O)CH═CH 2 , or —(CH 2 ) n OC(O)C(CH 3 )═CH 2 ;
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 , R 5 , R 7 , and R 9 are individually H, OR 20 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl;
R 20 is H or alkyl;
n is 1-12; and
X is an anion;
with the proviso that R 3 and R 5 or R 7 and R 9 are individually secondary alkyl, tertiary alkyl, or aryl.

Assignees

• Gentex Corp

Inventors

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

Classifications

• C08G2261/3221

  containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/6229

  Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols · CPC title

• C08G61/122

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

• C08G18/3293

  containing heterocyclic groups · CPC title