Organic dye with improved efficiency and uses thereof in photovoltaic cells

Patent metadata

Field	Value
Publication number	US-10655016-B2
Application number	US-201716099623-A
Country	US
Kind code	B2
Filing date	May 3, 2017
Priority date	May 9, 2016
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

An organic dye corresponding to one of the following structures (I) or (II): eD-pi-conjugated chromophore-L-A (I), or A-L-pi-conjugated chromophore-eD (II), where eD represents an electron donor segment, L represents a covalent bond or a spacer segment and in particular a pi-conjugated spacer segment, A represents an electron acceptor segment capable of forming a covalent bond with a semiconductor, in which the pi-conjugated chromophore comprises at least one unit of formula (III):

in which the radicals R1 and R2, which are identical or different, represent an optionally substituted aryl group; the radicals R3 to R8, which are identical or different, represent a hydrogen, an optionally substituted alkyl group or an optionally substituted aryl group; and X1 and X2, which are identical or different, are chosen from S, Se and O.

First claim

What is claimed is:

1. Organic dye corresponding to one of the following structures (I) or (II):
eD-pi-conjugated chromophore-L-A  (I)

A-L-pi-conjugated chromophore-eD  (II)

where:
eD represents an electron-donor segment,
L represents a covalent bond or a spacer segment and in particular a pi-conjugated spacer segment,
A represents an electron-attractor segment capable of forming a covalent bond with a semiconductor,

wherein the pi-conjugated chromophore comprises at least one unit of formula

where:
the radicals R 1 and R 2 , the same or different, are an optionally substituted aryl group;
the radicals R 3 to R 8 , the same or different, are a hydrogen, an optionally substituted alkyl group or optionally substituted aryl group; and
X 1 and X 2 , the same or different are selected from among S, Se and O.

2. The organic dye according to claim 1 , wherein said pair (X 1 ,X 2 ) represents (S,S), (O,O) or (Se,Se) and in particular (S,S).

3. The organic dye according to claim 1 , wherein in said unit (III), said radicals R 4 to R 6 are the same and/or the radicals R 7 and R 8 are the same, said radicals R 4 to R 6 preferably all representing a hydrogen and/or the radicals R 7 and R 8 preferably all representing a hydrogen.

4. The organic dye according to claim 1 , wherein in said unit (III), said radical R 3 represents a hydrogen.

5. The organic dye according to claim 1 , wherein in said unit (III), said radicals R 1 and R 2 are the same and represent an optionally substituted aryl group and in particular an aryl group substituted by an optionally substituted alkyl group.

6. The organic dye according to claim 1 , wherein said unit (III) is of formula (IV):

where the radicals R′ 1 and R′ 2 are the same and represent —C 6 H 4 —C 6 H 13 .

7. The organic dye according to claim 1 , wherein said electron-donor segment (eD) is an amino group of (Z 1 )(Z 2 )N-type with Z 1 and Z 2 , the same or different, representing an optionally substituted alkyl group or optionally substituted aryl group.

8. The organic dye according to claim 1 , wherein said electron-acceptor segment (A) is a carboxylic acid group, cyanoacrylic acid group, phosphonic group, dithiocarboic group or a group corresponding to any one of the following formulas:

9. The organic dye according to claim 1 , wherein said spacer L is a pi-conjugated function such as an optionally substituted alkenylene or alkynylene chain and/or an optionally substituted arylene chain.

10. The organic dye according to claim 1 , wherein said organic dye is selected from among the following compounds:

11. Use of an organic dye such as defined in claim 1 as photosensitizer in a photovoltaic device.

12. Photovoltaic device having a nanostructured semiconductor metal oxide layer sensitized by at least one organic dye such as defined in claim 1 .

13. The photovoltaic device according to claim 12 , wherein said photovoltaic device further comprises two electrodes, designated anode and counter-electrode in the invention, and separated from each other by an electrolyte and optionally polymer separators.

14. The photovoltaic device according to claim 12 , wherein the semiconductor metal oxide is a binary, tertiary or quaternary metal oxide.

15. The photovoltaic device according to claim 12 , wherein said electrolyte is a liquid, an ionic liquid, a gel or a solid.

Assignees

• Commissariat Energie Atomique

Inventors

• Demadrille Renaud
• Kervella Yann
• Joly Damien
• Godfroy Maxime

Classifications

• C09B23/105

  two >CH- groups · CPC title

• H01G9/2031

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

• C09B23/102 Primary

  two heterocyclic rings linked carbon-to-carbon (C09B7/00 takes precedence) · CPC title

• H01G9/2036

  comprising mixed oxides, e.g. ZnO covered TiO2 particles · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title