Boron containing perylene monoimides, a process for their production, their use as building blocks for the production of perylene monoimide derivatives, monoimide derivatives and their use in dye-sensitized solar cells

Patent metadata

Field	Value
Publication number	US-9624375-B2
Application number	US-201514746113-A
Country	US
Kind code	B2
Filing date	Jun 22, 2015
Priority date	Aug 6, 2012
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

Boron-comprising perylene monoimides and a process for producing the boron-comprising perylene monoimides are provided. The boron-comprising perylene monoimides are useful as building blocks for producing perylene monoimide derivatives and monoimide derivatives. The boron-comprising perylene monoimides are also useful for preparing dye-sensitized solar cells.

First claim

The invention claimed is:

1. A process for the preparation of compounds of general formula III

wherein the variables have the following meaning

R 1 , R 2 independently of each other a moiety of formula IIIa

R 4 , R 5 independently of each other aryl or hetaryl,
m 0 or 1, where in the case of m equal 1 R 2 is bound either to the 8 or 9 position of the perylene skeleton,
R 3 identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino,
n 0, 1, 2, 3 or 4
Y oxygen or NR 12 ,
and

R 12 hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
or
a moiety of formula —Z-A, wherein
A is —COOM, —SO 3 M or —PO 3 M,
M hydrogen, alkali metal cation or [NR′] 4+ ,
R′ hydrogen or alkyl, where the radicals R′ may be identical or different,
Z C 1 -C 6 -alkylene or 1,4-phenylene, where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen,

comprising
reacting a compound of general formula II

wherein the variables have the following meaning

Lg leaving group,
m 0 or 1, where in the case of m equal 1 the one Lg is bound either to the 8 or 9 position of the perylene skeleton and is identical to the Lg bound to the 11 position,
and the remaining variables R 3 , n and Y have the meaning as defined above with a compound or a mixture of compounds of general formula IIIa*

in the presence of a palladium containing catalyst under the conditions of the Buchwald-Hartwig amination reaction.

2. A process according to claim 1 wherein in general formula III the variables have the following meaning
R 1 , R 2 independently of each other a moiety of formula Ia

m 0 or 1, where in the case of m equal 1 R 2 is bound either to the 8 or 9 position of the perylene skeleton,
R 4 , R 5 independently of each other moieties of formulae Ib or Ic

R 6 hydrogen, alkyl, aryl, alkoxy, alkylthio or —NR 7 R 8 , where in case of two or more substituents (p equal or greater than 2) these may be identical or different,
p 0, 1, 2, 3, 4 or 5,
X C(R 9 R 10 ) 2 , NR 11 , oxygen or sulfur,
R 7 to R 11 hydrogen, alkyl, cycloalkyl, aryl or hetaryl.

3. Compounds of general formula III according to claim 1 .

4. A method of sensitizing a solar cell comprising adding the compound of claim 3 to a semiconductor material of a solar cell.

5. A dye-sensitized solar cell comprising compounds of general formula III prepared according to claim 1 .

Assignees

• Basf Se
• Max-Planck-Gesellschaft Zur Foerd Der Wisse E V
• Max-Planck-Gesellschaft Zur Foerderung Der Wss E V

Inventors

• Wonneberger Henrike
• Bruder Ingmar
• Send Robert
• Battagliarin Glauco
• Li Chen
• Muellen Klaus

Classifications

• H10K85/658

  Organoboranes · CPC title

• C07D221/18

  Ring systems of four or more rings · CPC title

• H01G9/2031

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

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0053

  Electricity · mapped topic