Perylene functionalized porphyrin dyes for dye-sensitized solar cells

Patent metadata

Field	Value
Publication number	US-9627633-B2
Application number	US-201414903585-A
Country	US
Kind code	B2
Filing date	Jul 8, 2014
Priority date	Jul 8, 2013
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

The invention relates to dyes for dye-sensitized solar cells, and in particular, to perylene functionalized porphyrin dyes for dye-sensitized solar cells. The invention further relates to a dye molecule comprising perylene functionalized porphyrin moiety.

First claim

The invention claimed is:

1. A dye-sensitized solar cell comprising a dye molecule of Formula (I):

wherein:
M is zinc, cobalt, nickel, iron, or copper;
each of L 1 and L 2 is a linker and is independently selected from the group consisting of a direct bond and an ethynylene group;
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 is independently selected from the group consisting of hydrogen, halogen, C 1-30 alkyl, and C 6 -C 20 aryl;
each of R 9 and R 10 is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted benzyl;
AG is an anchor group for attachment to a substrate; and
Pery is a perylene-based moiety of Formula (II):

wherein:
each of R 11 and R 12 is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted benzyl.

2. The dye-sensitized solar cell of claim 1 , wherein R 11 is a substituted or unsubstituted benzyl and R 12 is a substituted or unsubstituted phenyl.

3. The dye-sensitized solar cell of claim 2 , wherein R 12 is a mono-, di-, tri-, tetra-, or penta-substituted phenyl.

4. The dye-sensitized solar cell of claim 2 , wherein R 12 is a C 1-10 alkyl-substituted phenyl.

5. The dye-sensitized solar cell of claim 4 , wherein R 12 is tert-butylphenyl.

6. The dye-sensitized solar cell of claim 5 , wherein R 12 is para-tert-butylphenyl.

7. The dye-sensitized solar cell of claim 2 , wherein R 11 is a mono-, di-, tri-, tetra-, or penta-substituted benzyl.

8. The dye-sensitized solar cell of claim 7 , wherein R 11 is a C 1-10 alkyl-substituted benzyl.

9. The dye-sensitized solar cell of claim 8 , wherein R 11 is a di-C 1-10 alkyl-substituted benzyl.

10. The dye-sensitized solar cell of claim 9 , wherein R 11 is 3,5-di-tert-butylbenzyl.

11. The dye-sensitized solar cell of claim 1 , wherein R 9 , or R 10 , or both R 9 and R 10 are substituted or unsubstituted phenyl.

12. The dye-sensitized solar cell of claim 11 , wherein each of R 9 and R 10 is independently a mono-, di-, tri-, tetra-, or penta-substituted phenyl.

13. The dye-sensitized solar cell of claim 12 , wherein R 9 , or R 10 , or both R 9 and R 10 are independently C 1-10 alkyl-substituted phenyl.

14. The dye-sensitized solar cell of claim 13 , wherein R 9 , or R 10 , or both R 9 and R 10 are methylphenyl.

15. The dye-sensitized solar cell of claim 14 , wherein R 9 , or R 10 , or both R 9 and R 10 are trimethylphenyl.

16. The dye-sensitized solar cell of claim 15 , wherein R 9 , or R 10 , or both R 9 and R 10 are 2,4,6-trimethylphenyl.

17. The dye-sensitized solar cell of claim 12 , wherein R 9 , or R 10 , or both R 9 and R 10 are independently a C 1-15 alkoxy-substituted phenyl.

18. The dye-sensitized solar cell of claim 17 , wherein R 9 , or R 10 , or both R 9 and R 10 are octyloxyphenyl.

19. The dye-sensitized solar cell of claim 18 , wherein R 9 , or R 10 , or both R 9 and R 10 are 2,6-di-octyloxyphenyl.

20. The dye-sensitized solar cell of claim 17 , wherein R 9 , or R 10 , or both R 9 and R 10 are dodecyloxyphenyl.

21. The dye-sensitized solar cell of claim 20 , wherein R 9 , or R 10 , or both R 9 and R 10 are 2,6-di-dodecyloxyphenyl.

22. The dye-sensitized solar cell of claim 1 , wherein AG comprises a phenolic derivative of benzoic acid.

23. A dye molecule of Formula (I):

wherein:
M is zinc, cobalt, nickel, iron, or copper;
each of L 1 and L 2 is a linker and is independently selected from the group consisting of a direct bond and an ethynylene group;
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 is independently selected from the group consisting of hydrogen, halogen, C 1-30 alkyl, and C 6 -C 20 aryl;
each of R 9 and R 10 is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted benzyl;
AG is an anchor group for attachment to a substrate; and
Pery is a perylene-based moiety of Formula (II):

wherein:
each of R 11 and R 12 is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted benzyl.

Assignees

• Agency Science Tech & Res

Inventors

• Wu Jishan
• Luo Jie
• Jiang Changyun
• Zhang Jie

Classifications

• H01L51/0092 Primary

  Electricity · mapped topic

• C09B47/00

  Porphines; Azaporphines {(non-dyeing compounds C07D487/22)} · CPC title

• C07F3/06

  Zinc compounds · CPC title

• H01G9/2059

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title