Use of square planar transition metal complexes as dopant

Patent metadata

Field	Value
Publication number	US-9722190-B2
Application number	US-30182807-A
Country	US
Kind code	B2
Filing date	May 24, 2007
Priority date	May 24, 2006
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

The present invention relates to the use of a square planar transition metal complex as dopant, charge injection layer, electrode material or storage material.

First claim

The invention claimed is:

1. A method for p-doping an organic semiconductive matrix material, the method comprising combining an electrical p-dopant with the organic semiconductive matrix material, wherein the electrical p-dopant is a square planar transition metal complex, wherein the square planar transition metal complex comprises one of the following structures:

wherein:
M is a transition metal selected from groups 8 to 11 of the periodic system of the elements,
X 1 , X 2 , X 3 , and X 4 are independently selected from the group consisting of S, N, and P, wherein N and P are substituted with R 5 , and R 5 is independently selected from the group consisting of, substituted or unsubstituted, linear alkyl, branched alkyl, cycloalkyl, aryl, heteroaryl, condensed aromatic rings, donor groups, and acceptor groups,
R 1 and R 2 are independently selected from the group consisting of, substituted or unsubstituted, aromatic compounds, heteroaromatic compounds, aliphatic hydrocarbons, cycloaliphatic hydrocarbons, and nitrile,
L 1 and L 2 are independently selected from the group consisting of aromatic amine, aromatic phosphine, halogen, pseudohalogen, NCS, SCN, and CN, and
wherein the organic semiconductive matrix material is selected from the group consisting of metal phthalocyanine complexes, metal naphthocyanine complexes, metal porphyrine complexes, substituted or unsubstituted, arylated or heteroarylated amines, benzidine derivatives, imidazole derivatives, thiophene derivatives, thiazole derivatives, and dimeric, oligomeric, or polymeric heteroaromates, wherein the selected organic semiconductive matrix material has an oxidation potential, as determined by cyclovoltammetry, of greater than 0 V vs. Fc/Fc + .

2. The method according to claim 1 , wherein M is selected from the group consisting of nickel, copper, palladium, platinum, iron, cobalt, ruthenium, and osmium.

3. The method according to claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of substituted phenyl, anisyl, tolyl, 2-pyridyl, methyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, and trichloromethyl.

4. An organic semiconductive material comprising at least one organic matrix compound and an electrical p-dopant, wherein the electrical p-dopant is a square planar transition metal complex, wherein the square planar transition metal complex has one of the following structures:

wherein:
M is a transition metal selected from groups 8 to 11 of the periodic system of the elements,
X 1 , X 2 , X 3 , and X 4 are independently selected from the group consisting of S, N, and P, wherein N and P are substituted with R 5 , and R 5 is independently selected from, substituted or unsubstituted, linear alkyl, branched alkyl, cycloalkyl, aryl, heteroaryl, condensed aromatic rings, donor groups, and acceptor groups,
R 1 and R 2 are independently selected from the group consisting of, substituted or unsubstituted, aromatic compounds, heteroaromatic compounds, aliphatic hydrocarbons, cycloaliphatic hydrocarbons, and nitrile,
L 1 and L 2 are independently selected from the group consisting of aromatic amine, aromatic phosphine, halogen, pseudohalogen, NCS, SCN, and CN, and
wherein the organic matrix compound is selected from the group consisting of metal phthalocyanine complexes, metal naphthocyanine complexes, metal porphyrine complexes, substituted or unsubstituted, arylated or heteroarylated amines, benzidine derivatives, imidazole derivatives, thiophene derivatives, thiazole derivatives, and dimeric, oligomeric, or polymeric heteroaromates, wherein the selected organic semiconductive matrix material has an oxidation potential, as determined by cyclovoltammetry, of greater than 0 V vs. Fc/Fc + .

5. The organic semiconductive material according to claim 4 , wherein the molar doping ratio of dopant to matrix molecule or the doping ratio of dopant to monomeric units of a polymeric matrix molecule is between 20:1 and 1:100,000.

6. The method according to claim 3 , wherein the substituted phenyl is trifluoromethylphenyl.

7. The organic semiconductive material according to claim 5 , wherein the molar doping ratio of dopant to matrix molecule or the doping ratio of dopant to monomeric units of a polymeric matrix molecule is between 10:1 and 1:1,000.

8. The organic semiconductive material according to claim 5 , wherein the molar doping ratio of dopant to matrix molecule or the doping ratio of dopant to monomeric units of a polymeric matrix molecule is between 1:1 and 1:100.

Assignees

• Zeika Olaf
• Dathe Rene
• Willmann Steffen
• Werner Ansgar
• Novaled Gmbh

Inventors

• Zeika Olaf
• Dathe Rene
• Willmann Steffen
• Werner Ansgar

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0077

  Electricity · mapped topic

• H01L51/002

  Electricity · mapped topic

• H01L51/0062

  Electricity · mapped topic

• H01L51/0083 Primary

  Electricity · mapped topic