Copper(I) complexes, in particular for optoelectronic components

Patent metadata

Field	Value
Publication number	US-9917265-B2
Application number	US-201214129707-A
Country	US
Kind code	B2
Filing date	Jun 29, 2012
Priority date	Jun 29, 2011
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

The embodiments of the invention relate to copper(I) complexes of the formula A

where
X* is Cl, Br, I, CN, SCN, alkinyl and/or N 3 (independently of one another),
N*∩E is a bidentate ligand with
E being a phosphanyl/arsenyl group of the form R 2 E (in which R=alkyl, aryl, alkoxyl, phenoxyl, or amide), N* is an imine-function, which is a component of an N-heteroaromatic 5-membered ring that is selected from the group consisting of pyrazole, isoxazole, isothiazole, triazole, oxadiazole, thiadiazole, tetrazole, oxatriazole or thiatriazole, and “∩” is at least one carbon atom, which is likewise a component of the aromatic group, the carbon atom being located directly adjacent both to the imine nitrogen atom as well as to the phosphorus or arsenic atom.

The copper(I) complexes may be used in optoelectronic components, particularly in organic light emitting diodes (OLEDs).

First claim

The invention claimed is:

1. A copper(I) complex of formula A:

wherein:
X* is selected from the group consisting of Cl, Br, I, CN, SCN, akinyl and N 3 ; and
N*∩E is a bidentate ligand wherein
E is a phosphanyl/arsenyl group of the R 2 E form, wherein R is selected from the group consisting of alkyl, aryl, alkoxyl, phenoxyl and amide,
N* is an imine-function which is part of an N-heteroaromatic 5-membered ring selected from the group consisting of pyrazole, isoxazole, isothiazole, triazole, oxadiazole, tetrazole, oxatriazole and thiatriazole,
∩ is at least one carbon atom, which is part of the N-heteroaromatic group, wherein the at least one carbon atom being directly adjacent both to the imine nitrogen atom and to the phosphorus or arsenic atom.

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

3. The copper(I) complex according to claim 2 , wherein the at least one substituent for increasing solubility is selected from the group consisting of branched or unbranched or cyclic long-chained alkyl chains with a length of C1 to C30, branched or unbranched or cyclic long-chained alkoxy chains with a length of C1 to C30, branched or 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 of claim 1 , wherein N*∩E is selected from the group consisting of

wherein:
X is selected from the group consisting of O, S and NR 2 ;
E* is As or P; and
R1-R3 are independently selected from the group consisting of hydrogen, halogen, substituents bound via oxygen (—OR), nitrogen (—NR 2 ), silicon atoms (—SiR 3 ), alkyl- (branched or cyclic), aryl, heteroaryl, alkenyl, akinyl groups, substituted alkyl (branched or cyclic), aryl, heteroaryl and alkenyl groups with substituents selected from the group consisting of halogens or deuterium, alkyl groups (branched or cyclic), and donor and acceptor groups selected from the group consisting of amines, carboxylates and their esters, and CF 3 -groups.

5. The copper(I) complex of claim 4 , wherein R2-R3 lead to annulated ring systems.

6. The copper (I) complex of formula A according to claim 4 , wherein the bidentate ligand has the formula B:

7. The copper(I) complex of claim 1 , wherein the copper(I) complex is used as an emitter or an absorber in an optoelectronic component.

8. The copper(I) complex of claim 7 , wherein the optoelectronic component is selected from the group consisting of organic light emitting components (OLEDs), light emitting electrochemical cells, OLED-sensors, in particular gas and vapor sensors which are not hermetically sealed from the outside, organic solar cells, organic field-effect transistors, organic lasers, and down conversion elements.

9. The copper(I) complex of claim 7 , wherein the concentration of the copper(I) complex as the emitter in the optical light emitting component is between 1% and 80%.

10. An optoelectronic component comprising the copper(I) complex of claim 1 , shaped as a component selected from the group consisting of organic light emitting component, organic diode, organic solar cell, organic transistor, organic light emitting diode, light emitting electrochemical cell, organic field-effect transistor, and organic laser.

11. The copper(I) complex of claim 1 , wherein the copper(I) complex is used in an optoelectronic component for converting UV radiation or blue light to visible light.

12. The copper(I) complex of claim 11 , wherein the copper(I) complex is used in the optoelectronic component for converting UV radiation or blue light to at least one of green, yellow and red light.

Assignees

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

Inventors

• Baumann Thomas
• Grab Tobias
• Zink Daniel

Classifications

• H01L51/5016

  Electricity · mapped topic

• C07F1/005

  without C-Metal linkages · CPC title

• H01L51/009

  Electricity · mapped topic

• Y02P70/521

  Cross-Sectional Technologies · mapped topic

• H01L51/0091 Primary

  Electricity · mapped topic