Porphyrin based sensitizer for dye-sensitized solar cell

Patent metadata

Field	Value
Publication number	US-9812658-B2
Application number	US-201415101975-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Dec 13, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

The present invention relates to compounds of formula (I)

based on a porphyrin core and a π-conjugated linker or acceptor introduced between the porphyrin core and an anchoring group having a high absorption coefficient covering the whole UV-Visible and near-infrared spectral response, and their use as sensitizer or dye and an electrochemical or optoelectronic device including a compound of the invention.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
M is selected from Co, Cu, Fe, Mg, Mn, Ni, Si or Zn or M is two H (hydrogen) substituting two pyrrole moieties constituting the porphyrin core;
A is an acceptor group selected from a moiety according to any one of the formulae (1) to (36) and (103) to (105)

wherein R 1 -R 2 , R 4 -R 13 , R 17 -R 68 and R 137 -R 141 are substituents independently selected from H, C1-C16 alkyl, C1-C16 alkoxy, C1-C16 thioalkyl, C1-C16 alkoxyalkyl, C4-C16 aryl, C1-C16 arylalkyl or C4-C16 heteroaryl, C4-C16 heteroarylalkyl wherein heteroatoms are selected from O, S, or N;
Anc is an anchoring group selected from a moiety according to any one of formulae (37) to (53)

wherein R 69 and R 70 are substituents independently selected from H, C1-C16 alkyl, C1-C16 alkoxy, C1-C16 thioalkyl, C1-C16 alkoxyalkyl, C4-C16 aryl, C1-C16 arylalkyl or C4-C16 heteroaryl, C4-C16 heteroarylalkyl wherein heteroatoms are selected from O, S, or N;
L 1 and L 2 are substituents independently selected from a moiety according to any one of formulae (54) to (65)

wherein R 71 -R 100 are substituents independently selected from H, C1-C16 alkyl, C1-C16 alkoxy, C1-C16 thioalkyl, C1-C16 alkoxyalkyl, C4-C16 aryl, C1-C16 arylalkyl or C4-C16 heteroaryl, C4-C16 heteroarylalkyl wherein heteroatoms are selected from O, S, or N;
Ar 1 and Ar 2 are donor substituents being selected from a moiety according to any one of formulae (66) to (88)

wherein R 101 -R 136 and R 142 are substituents independently selected from H, C1-C16 alkyl, C1-C16 alkoxy, C1-C16 thioalkyl, C1-C16 alkoxyalkyl, C4-C16 aryl, C1-C16 arylalkyl or C4-C16 heteroaryl, C4-C16 heteroarylalkyl wherein heteroatoms are selected from O, S, or N.

2. The compound of formula (I) according to claim 1 , wherein A is selected from a moiety according to any one of the formulae (1)-(12), (14), (15), (25), (27), (30), and (31).

3. The compound of formula (I) according to claim 1 , wherein Anc is selected from a moiety according to any one of the formulae (37) to (47).

4. The compound of formula (I) according to claim 1 , wherein Ar 1 and Ar 2 are selected from a moiety according to any one of the formulae (67), (75) to (81).

5. The compound of formula (I) according to claim 1 , wherein L 1 and L 2 are selected from a moiety according to any one of the formulae (55) to (58).

6. The compound of formula (I) according to claim 1 , wherein Ar 1 and Ar 2 are identical moieties.

7. The compound of formula (I) according to claim 1 , wherein L 1 and L 2 are identical moieties.

8. The compound of formula (I) according to claim 1 , wherein Ar 1 and Ar 2 are moiety (77).

9. The compound of formula (I) according to claim 1 , wherein L 1 and L 2 are moiety (55).

10. A dye or a sensitizing compound of an electrochemical or optoelectronic device comprising a compound of formula (I) according to claim 1 .

11. An electrochemical or optoelectronic device comprising a dye being a compound of formula (I) according to claim 1 .

12. The device according to claim 11 , wherein said device is selected from an electrochemical device, a photo-electrochemical device, an optoelectronic device, a light emitting device, an electrochromic or photo-electrochromic device, an electrochemical sensor, an electrochemical display or a dye sensitized solar cell.

Assignees

• Ecole Polytechnique Fed De Lausanne (Epfl)

Inventors

• Yi Chenyi
• Giordano Fabrizio
• Zakeeruddin Shaik Mohammad
• Graetzel Michael

Classifications

• H01G9/2031

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• C09B47/00 Primary

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

• Y02E10/549

  Organic PV cells · 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