Organic dye for a dye-sensitized solar cell

Patent metadata

Field	Value
Publication number	US-2016264782-A1
Application number	US-201415036277-A
Country	US
Kind code	A1
Filing date	Nov 14, 2014
Priority date	Nov 15, 2013
Publication date	Sep 15, 2016
Grant date	—

Abstract

Organic dye for a dye-sensitized solar cell (DSSC) comprising at least one electron-acceptor unit and at least one π-conjugated unit. Said organic dye is particularly useful in a dye-sensitized photoelectric transformation element which, in its turn, can be used in a dye-sensitized solar cell (DSSC).

First claim

1 . An organic dye having formula (I):

wherein:
T 1 and T 2 , equal to or different from each other, are selected from the group consisting of a thiophenyl group of formula (II), a 2,2′-bithiophenyl group of formula (III), and a 2,2′:5′,2″-terthiophenyl group of formula (IV):

A is selected from: —COOH group, phosphonic groups having formula —PO(OH) 2 or —PO(OH)(R) wherein R represents a C 1 -C 20 alkyl group, linear or branched, or carboxycyanovinylene groups having formula (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), or (XIII):

wherein R 17 , R 18 and R 19 , equal to or different from each other, represent a hydrogen atom, or are selected from C 1 -C 20 , alkyl groups, linear or branched and W represents an oxygen atom or a sulphur atom;
R 1 represents a hydrogen atom; or is selected from: C 1 -C 20 alkyl groups, linear or branched, saturated or unsaturated, optionally containing heteroatoms, C 4 -C 12 cycloalkyl groups optionally substituted, C 6 -C 24 aryl groups optionally substituted, alkoxyl or aryloxyl groups optionally substituted, thioalkoxyl or thioaryloxyl groups optionally substituted, trialkyl- or triaryl-silyl groups optionally substituted, polyethyleneoxylic groups having formula R′—O—[—CH 2 —CH 2 —O—] q — wherein R′ represents a hydrogen atom, or is selected from C 1 -C 20 alkyl groups, linear or branched, and q is an integer ranging from 1 to 20;
R 2 and R 3 , equal to or different from each other, are selected from: C 1 -C 20 alkyl groups, linear or branched, saturated or unsaturated, optionally containing heteroatoms, C 4 -C 12 cycloalkyl groups optionally substituted, C 6 -C 24 aryl groups optionally substituted, polyethyleneoxylic groups having formula R′—O—CH 2 —CH 2 — q — wherein R′ represents a hydrogen atom, or is selected from C 1 -C 20 alkyl groups, linear or branched, and q is an integer ranging from 1 to 20;
or, R 2 and R 3 , can be optionally bound to each other to form, together with the other atoms to which they are bound, a saturated, unsaturated or aromatic, cycle containing from 1 to 12 carbon atoms, optionally substituted with: C 1 -C 20 alkyl groups, linear or branched, saturated or unsaturated, optionally containing heteroatoms, C 6 -C 24 aryl groups optionally substituted, C 4 -C 12 cycloalkyl groups optionally substituted, halogen atoms such as fluorine, chlorine, bromine, iodine, cyano groups, nitro groups; said cycle optionally containing other heteroatoms such as oxygen, sulphur, nitrogen, silicon, phosphorous, selenium, boron;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 , equal to or different from each other, represent a hydrogen atom; or are selected from: C 1 -C 20 alkyl groups, linear or branched, saturated or unsaturated, optionally containing heteroatoms, C 4 -C 30 cycloalkyl groups optionally substituted, C 6 -C 36 aryl groups optionally substituted, trialkyl- or triaryl-silyl groups optionally substituted;
X and Y, equal to or different from each other, represent an heteroatom such as oxygen, sulphur, selenium, tellurium;
n is an integer ranging from 1 to 3;
m and p, equal to or different from each other, are an integer ranging from 0 to 12, with the proviso that m+p is equal to or higher than 1.

2 . The organic dye according to claim 1 , wherein in formula (1):
A is a carboxycyanovinylene group having formula (V):

wherein R 17 represents a hydrogen atom;
T 1 is a thiophenyl group of formula (II):

wherein R 4 and R 5 equal to or different from each other, represent a hydrogen atom; or are selected from C 1 -C 20 , linear or branched, saturated or unsaturated;
T 2 is a 2,2′:5′,2″-terthiophenyl group of formula (IV):

wherein R 11 , R 13 , R 14 and R 16 , equal to or different from each other, represent a hydrogen atom; or are selected from C 1 -C 20 , linear or branched, saturated or unsaturated; R 12 and R 15 , equal to or different from each other, are selected from C 1 -C 20 , linear or branched, saturated or unsaturated;
R 1 is a hydrogen atom; or is selected from C 1 -C 20 alkyl groups, linear or branched, saturated or unsaturated;
R 2 and R 3 are bound to each other to form, together with the other atoms to which they are bound, a saturated cycle containing 4 carbon atoms and two heteroatoms;
X and Y, equal to each other, represent oxygen or sulphur;
n is 1;
m is 0 or 1;
p is 0 or 1; and
m+p is 1 or 2.

3 . A dye-sensitized photoelectric transformation element comprising at least one organic dye having formula (I) according to claim 1 , said dye-sensitized photoelectric transformation element being supported on oxide semiconductor particles.

4 . A dye-sensitized solar cell comprising the dye-sensitized photoelectric transformation element according to claim 3 .

5 . The organic dye according to claim 1 , wherein A is selected from phosphonic groups having formula —PO(OH) 2 or —PO(OH)(R), wherein R represents a C 2 -C 8 , alkyl group.

6 . The organic dye according to claim 1 , wherein A is selected from carboxycyanovinylene groups having formula (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), or (XIII), wherein R 17 , R 18 and R 19 , equal to or different from each other, represent a hydrogen atom, or are selected from C 2 -C 8 , alkyl groups, linear or branched.

7 . The organic dye according to claim 1 , wherein m and p, equal to or different from each other, are an integer ranging from 0 to 5, with the proviso that m+p is equal to or higher than 2.

8 . The organic dye according to claim 2 , wherein R 4 and R 5 equal to or different from each other, represent a hydrogen atom.

9 . The organic dye according to claim 2 , wherein R 11 , R 13 , R 14 and R 16 , equal to or different from each other, represent a hydrogen atom.

10 . The organic dye according to claim 2 , wherein R 12 and R 15 , equal to or different from each other, are a n-hexyl group.

11 . The organic dye according to claim 2 , wherein R 1 is a hydrogen atom or a n-hexyl group.

12 . The organic dye according to claim 2 , wherein R 2 and R 3 are bound to each other to form, together with the other atoms to which they are hound, a saturated cycle containing 4 carbon atoms and two heteroatoms, said heteroatoms being oxygen or sulphur.

Assignees

• Eni Spa
• Cnrs (Centre Nat De La Rech Scientifique)

Inventors

• Biagini Paolo
• Po' Riccardo
• Roncali Jean
• Demeter Dora

Classifications

• H01G9/2027

  comprising an oxide semiconductor electrode · CPC title

• C09B23/102 Primary

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

• Y02E10/542

  Dye sensitized solar cells · CPC title

• Y02E10/549

  Organic PV cells · 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