Electrochromic compounds with improved color stability in their radical states
An electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes, the electrochromic represented by Formula (I):
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.