Compounds for electrochemical and/or optoelectronic devices having peri-fused ring system

Patent metadata

Field	Value
Publication number	US-9324505-B2
Application number	US-201114349792-A
Country	US
Kind code	B2
Filing date	Oct 18, 2011
Priority date	Oct 18, 2011
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The invention relates to substituted ullazine and analogs of ullazine as sensitizers for dye-sensitized solar cells (DSSCs) and other photoelectrochemical and/or optoelectronic devices. The sensitizers may comprise donor substituents and/or acceptor substituents, besides an anchoring group suitable for attaching the sensitizer on a semiconductor surface. DSSCs based on this type of sensitizers exhibit high power conversion efficiencies.

First claim

The invention claimed is:

1. A photoelectrochemical and/or an optoelectronic device comprising a compound being a substituted 16 π-electron ring system, wherein said ring system comprises four peri-fused rings, at least one nitrogen heteroatom and at least one substituent comprising an anchoring group suitable to anchor said compound on the surface of a semiconductor.

2. The device of claim 1 , wherein, in said compound, two of said four rings have each a bond and/or two atoms in common with each of two other rings of said four rings, said two other rings having each a bond and/or two atoms in common with each of the other three rings of said four rings.

3. The device of claim 1 , wherein said ring system comprises at least one donor substituent that comprises an electron donating (a donor) group, such that said donor substituent is capable of transferring an electron to said ring system.

4. The device of claim 1 , wherein said ring system comprises at least one acceptor substituent that comprises an electron accepting group, such that said acceptor substituent can take up an electron from said ring system.

5. The device of claim 1 which is selected from a photovoltaic cell, a light emitting device, an electrochromic device, a photo-electrochromic device, an electrochemical sensor, a biosensor, and an electrochemical display.

6. The device of claim 1 , which is a dye-sensitized solar cells (DSSCs).

7. The device of claim 1 comprising a counter electrode, a charge transfer material and a semiconductor material, wherein the substituted 16 π-electron ring system is adsorbed onto the surface of the semiconductor material and wherein said charge transfer material is in contact with the counter electrode and the surface of the semiconductor material.

8. The device of claim 1 , wherein said compound comprises a structure according to any one of formulae (I) to (VIII) below:

wherein
the atoms X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , in as far as present, are either all carbon atoms or one may independently be nitrogen and the other being carbons;
if any one X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , in as far as present, is nitrogen, the respective substituent (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , respectively) is absent;
Y is selected, independently, from O, S, Se, SiR 10 R 11 and NR 10 ;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , in as far as present, are selected independently from H, and C1 to C40 hydrocarbons comprising 0 to 20 heteroatoms, and from C0 to C40 hydrocarbons comprising 1 to 20 heteroatoms; with the proviso that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 comprises the anchoring group; and,
R 10 are R 11 are independently selected from H and C1 to C40 hydrocarbons comprising 0 to 20 heteroatoms.

9. The device of claim 8 , wherein the compound of formula (I), (II), (IV), (VII) or (VIII) is respectively selected from compounds of formulae (IX) to (XI), (XII) to (XIV), (XV), (XVI), and (XVII) below:

wherein any one of R 1 to R 10 , in as far as present, are selected independently from H, and Cl to C40 hydrocarbons comprising 0 to 20 heteroatoms, and from C0 to C40 hydrocarbons comprising 1 to 20 heteroatoms; with the proviso that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 comprises the anchoring group; and, Y is selected, independently, from O, S, Se, SiR 11 R 12 and NR 11 , R 11 are R 12 are independently selected from H and C1 to C40 hydrocarbons comprising 0 to 20 heteroatoms.

10. The device of claim 8 , wherein one or more of said substituents R 1 to R 9 , in as far as present, is independently selected from substituents of formula (XVIII) below:

wherein U is, independently of n, selected from =(ethynylene) and from an ethylene moiety of formula (XIX) below (substituted and unsubstituted vinylene):

wherein n is selected from 0, and from integers 1 to 10, preferably 0, 1, 2 and 3;
wherein the dotted line in formula (XVIII) and (XIX) represents a single bond to one of the peripheral atoms of the 16 π-electron ring system, or to a linker moiety connecting said substituent of formula (XVIII) to said ring system in a π-conjugated manner;
R 1 is selected from a moiety of formula (XX), (XXI) and (XXII) below:

and further from —OR 8 , —SR 8 , —SeR 8 , —NR 8 R 9 , wherein R 8 and R 9 are independently selected from H and from C1 to C40 hydrocarbons comprising 0 to 20 heteroatoms;
wherein the dotted line in the structure of formulae (XX) to (XXII) represents a single bond by which substituent R 1 is connected to the respective carbon of moiety U, or, if n is 0, to one of the peripheral atoms of the 16 π-electron ring system, or to a π-conducting linker moiety connecting said substituent of formula (XVIII) to said ring system;
wherein Z is selected from O, S, Se, NR 8 , SiR 8 R 9 ;
wherein R 3 , R 4 , R 5 , R 6 , R 7 , in as far as present, are independently selected from H, R 8 , R 9 , —OR 8 , —SR 8 , —SeR 8 , —NR 8 R 9 , wherein any one of R 3 to R 7 may be connected to another one of substituents R 3 to R 7 so as to form a ring or ring system fused to said moiety of formula (XX), (XXI) or (XXII), respectively, and, if any one of R 3 , R 4 , R 5 , R 6 , and R 7 , is selected from —OR 8 , —SR 8 , —SeR 8 , —NR 8 R 9 , said R 8 and/or R 9 may, if it is not H, independently be connected with any other one of R 3 to R 7 so as to form a ring or ring system fused to said moiety of formulae (XX), (XXI) or (XXII), respectively, and wherein, if any one of R 3 , R 4 , R 5 , R 6 , and R 7 , is selected from —NR 8 R 9 , said R 8 and R 9 may be connected to each other so that the respective substituent of R 3 to R 7 is an N-containing heteroring or ring system bound to said moiety of formulae (XX), (XXI) or (XXII), respectively;
wherein R 2 and R 10 are independently selected from H and substituents as defined for R 1 .

11. The device of claim 8 , wherein one or more of said substituents R 1 to R 9 , in as far as present, comprises a substituent or moiety selected from —CN, —CF 3 , —F, —Cl, —Br, —I, —NO 2 , an amide moiety, —COOH, —COOR 29 , —C(O)R 29 , —C(O))H, and from the moieties of formulae (XXX) to (XXXVIII) below:

wherein said amide moiety may in particular be selected from moieties of formulae (XL) to (XLIV) below:

wherein the dotted line in the structures of formulae (XXX) to (XXXVIII) and (XL) to (XLIV) represents a single bond connecting said structure to one of the peripheral atoms of the 16 π-electron ring system, or to a π-conducting linker moiet

Assignees

• Delcamp Jared
• Graetzel Michael
• Nazeeruddin Mohammad Khaja
• Ecole Polytech

Inventors

• Delcamp Jared
• Graetzel Michael
• Nazeeruddin Mohammad Khaja

Classifications

• Y02P70/521

  Cross-Sectional Technologies · mapped topic

• Y02E10/542

  Dye sensitized solar cells · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0064

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic