Copper(I) complexes, in particular for optoelectronic components

Patent metadata

Field	Value
Publication number	US-9490431-B2
Application number	US-201214117190-A
Country	US
Kind code	B2
Filing date	May 14, 2012
Priority date	May 13, 2011
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

The invention relates to copper(I) complexes of the formula A,

in which
X*═Cl, Br, I, CN and/or SCN (i.e. independently of one another); N*∩E=a bidentate ligand where
E=phosphanyl/arsenyl group of the R 2 E form (where R=alkyl, aryl, alkoxyl, phenoxyl, or amide); N*=imine function, which is part of a N-heteroaromatic 5- or 6-membered ring, which is chosen from the group consisting of oxazole, imidazole, thiazole, isoxazole, isothiazole, pyrazole, 1,2,3-triazole, 1,2,3-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazole and 1,2,5-thiadiazole, pyridine, pyrimidine, triazine, pyrazine and pyridazine; and “∩”=at least one carbon atom, which is likewise part of the aromatic group, wherein the carbon atom is directly adjacent to both the imine nitrogen atom and to the phosphorous or arsenic atom.

First claim

The invention claimed is:

1. A copper(I) complex of formula A

wherein:
X*=at least one of Cl, Br, I, CN and SCN
N*∩E=a bidentate ligand, wherein
E=phosphanyl/arsenyl group of the R 2 E form, wherein R=one of alkyl, aryl, alkoxyl, phenoxyl, and amide;
N*=an imine function, which is part of a N-heteroaromatic 5-membered ring, which is selected from the group consisting of oxazole, imidazole, thiazole, isoxazole, isothiazole, pyrazole, 1,2,3-triazole, 1,2,3-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazole and 1,2,5-thiadiazole, or an imine function, which is part of a N-heteroaromatic 6-membered ring, which is chosen from the group consisting of pyridine, pyrimidine, triazine, pyrazine and pyridazine; and
∩=at least one carbon atom, which is part of the aromatic group, wherein the at least one carbon atom is directly adjacent to both the imine nitrogen atom and to the phosphorous or arsenic atom.

2. The copper(I) complex according to claim 1 , wherein N*∩E includes at least one substituent for increasing the solubility of the copper(I) complex in an organic solvent.

3. A copper(I) complex according to claim 2 , wherein the substituent for increasing solubility is selected from the group consisting of:
branched, unbranched or cyclic long-chained alkyl chains with a length of C1 to C30;
branched, unbranched or cyclic long-chained alkoxy chains with a length of C1 to C30;
branched, unbranched or cyclic long-chained perfluoro alkyl chains with a length of C1 to C30; and
short-chained polyethers with a chain length of 3-50 repeating units.

4. The copper(I) complex according to claim 1 , wherein N*∩E is selected from the group consisting of:

wherein
X=O or NR 2
Y=O, NR 2 or S
E*=As or P
R1-R5 are each independently from each other hydrogen, a halogen or substituents which are bound via oxygen (—OR), nitrogen (—NR 2 ) or silicon atoms (—SiR 3 ), as well as alkyl-, aryl-, heteroaryl-, alkenyl-, alkinyl-groups and respectively substituted alkyl-, aryl-, heteroaryl- and alkenyl-groups.

5. A method for preparing the copper(I) complex of claim 1 , comprising:
performing a reaction of N*∩E with Cu(I)X*.

6. The method according to claim 5 , wherein the reaction is performed in dichloromethane.

7. The method according to claim 6 , further comprising adding diethyl ether or pentane to obtain the copper(I) complex in the form of a solid.

8. The method according to claim 5 , further comprising substituting at least one ligand N*∩E with at least one substituent selected from the group consisting of:
long-chained branched, unbranched or cyclic alkyl chains with a length of C1 to C30;
long-chained branched, unbranched or cyclic alkoxy chains with a length of C1 to C30;
branched, unbranched or cyclic perfluoro alkyl chains with a length of C1 to C30; and
short-chained polyethers.

9. The method according to claim 5 , further comprising preparing the bidentate ligand having the formula B,

pursuant to one of:
a)

10. An optoelectronic component comprising at least one of an emitter and an absorber having the copper(I) complex of claim 1 .

11. The optoelectronic component according to claim 10 , wherein the optoelectronic component is selected from the group consisting of:
an organic light emitting diode (OLED);
a light emitting electrochemical cell;
an OLED-sensor;
an organic solar cell;
an organic field-effect transistor;
an organic laser; and
a down conversion element.

12. An optoelectronic component comprising the copper(I) complex of claim 1 .

13. The optoelectronic component according to claim 12 , wherein the optoelectronic component is selected from the group consisting of an organic light emitting component, an organic diode, an organic solar cell, an organic transistor, an organic light emitting diode, a light emitting electrochemical cell, an organic field-effect transistor and an organic laser.

14. A method for manufacturing an optoelectronic component, comprising applying the copper(I) complex of claim 1 onto a carrier.

15. The method according to claim 14 , wherein the application of the copper(I) complex is performed by a wet-chemical process, by using a colloidal suspension means or by sublimation.

16. The cooper(I) complex according to claim 1 , wherein the bidentate ligand has the formula B,

Assignees

• Baumann Thomas
• Grab Tobias
• Zink Daniel
• Cynora Gmbh

Inventors

• Baumann Thomas
• Grab Tobias
• Zink Daniel

Classifications

• H01L51/0008

  Electricity · mapped topic

• C07F9/65318

  having the two nitrogen atoms in positions 1 and 3 · CPC title

• C07F9/65126

  Chemistry & Metallurgy · mapped topic

• C07F9/65066

  Chemistry & Metallurgy · mapped topic

• H01L51/5016

  Electricity · mapped topic