IP Library Granted Patent US 10,158,092
Granted Patent B2
US 10,158,092 · App. 15/791,167 · Granted Dec 18, 2018

Organic electronic component with dopant, use of a dopant and method for the production of the dopant

Inventors: Guenter Schmid (Hemhofen, DE); Jan Hauke Wemken (Nuremberg, DE); Renate Kellermann (Erlangen, DE); Andreas Kanitz (Hoechstadt, DE); Benedict Hendrik Sandmann (Hunderdorf, DE)
Assignee: OSRAM OLED GmbH
H01L51/0091C07F1/005C09K11/06H01L51/002H01L51/506H05B33/14C09K2211/188Y02E10/549
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Quick Facts
Patent No.
US 10,158,092
App. No.
15/791,167
Granted
Dec 18, 2018
Kind
B2
Abstract

An organic electronic component includes a substrate and a first electrode arranged on the substrate, and at least one organic functional layer arranged on the first electrode. The organic functional layer includes a matrix material into which a p-dopant has been introduced and a second electrode arranged on the organic functional layer. The p-dopant includes a copper complex having at least two ligands. Each ligand has a benzene unit with six carbon atoms. With respect to each ligand, an iminium group is linked directly as a substituent to one of the six carbon atoms of the benzene unit, and an oxygen is bound as a substituent to an adjacent carbon atom of the benzene unit, with the oxygen and the benzene unit together forming an aryloxy group. The ligands are coordinated to the copper cation, so that the copper complex has a trans-structure. The organic functional layer is hole-conducting.

Claims (22)

1. An organic electronic component, comprising:

a substrate;

a first electrode arranged on the substrate;

at least one organic functional layer arranged on the first electrode, the at least one organic functional layer comprising a matrix material into which a p-dopant has been introduced; and

a second electrode arranged on the at least one organic functional layer,

wherein the p-dopant comprises a copper complex having a copper cation and at least two ligands,

wherein each ligand has a benzene unit comprising six carbon atoms,

wherein, with respect to each ligand, an oxygen is bound as a substituent to one of the six carbon atoms of the benzene unit, with the oxygen and the benzene unit together forming an aryloxy group, and an adjacent carbon atom of the six carbon atoms of the benzene unit is substituted with a substituent that, together with the benzene unit, forms an iminium group,

wherein the at least two ligands are coordinated to the copper cation, so that the copper complex has a trans-structure, and

wherein the at least one organic functional layer is hole-conducting.

2. The component according to claim 1 , wherein the aryloxy group and the iminium group of one of the at least two ligands are a salicylaldiminate group.

3. The component according to claim 1 , wherein the copper cation is in an II oxidation state.

4. The component according to claim 1 , wherein the matrix material is a hole transport material comprising organic small molecules, polymers or mixtures thereof.

5. The component according to claim 4 , wherein the hole transport material is N,N′-di-[(1-naphthyl)-N,N′-diphenyl]-1,1′-biphenyl)-4,4′-diamine.

6. The component according to claim 1 , wherein each molecule of the p-dopant is coordinated by at least one molecule of the matrix material.

7. The component according to claim 1 , wherein the p-dopant is present in the matrix material in a concentration of 0.1 to 50% by volume relative to the volume of the matrix material.

8. The component according to claim 1 , wherein the component is a field-effect transistor, a solar cell, a photodetector, an optoelectronic component, a light-emitting diode or a display.

9. The component according to claim 1 , wherein the at least one organic functional layer is a hole transport layer or a hole-conducting layer of a charge-generating layer sequence.

10. A method for producing a p-dopant for an organic electronic component, the method comprising:

synthesizing at least two ligands and, simultaneously, complexing a copper cation with the at least two ligands;

wherein each ligand of the at least two ligands has a benzene unit comprising six carbon atoms, wherein, with respect to each ligand, an oxygen is bound as a substituent to one of the six carbon atoms of the benzene unit, with the oxygen and benzene unit together forming an aryloxy group, and an adjacent carbon atom of the six carbon atoms of the benzene unit is substituted with a substituent that, together with the benzene unit, forms an iminium group, and

wherein the at least two ligands are coordinated to the copper cation, so that the copper complex has a trans-structure.

Assignments (1)
MERGER Recorded Feb 17, 2026
From: OSRAM OLED GMBH
To: AMS-OSRAM INTERNATIONAL GMBH
Reel/Frame 074881/0104 →
Priority Claims (1)
DE 10 2011 084 639 · Oct 17, 2011 · national
Continuity (2)
Continuation 14352292
Related Publication 20180108849A1 · Apr 19, 2018