Organic electronic component having a charge carrier generation layer and the use of a zinc complex as a P-type dopant in charge carrier generation layers

Patent metadata

Field	Value
Publication number	US-10581001-B2
Application number	US-201615763068-A
Country	US
Kind code	B2
Filing date	Sep 27, 2016
Priority date	Sep 28, 2015
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

The invention relates to an organic electronic component ( 100 ) comprising at least one charge generation layer ( 5 ) which has an organically p-doped region ( 5 a ) that contains a zinc complex as a p-dopant, said zinc complex in turn containing at least one ligand L of the following structure: formula (I) wherein R1 and R2 can be oxygen, sulphur, selenium, NH or NR4 independently from one another, wherein R4 is selected from the group containing alkyl or aryl and which can be bonded to R3; and wherein R3 is selected from the group containing alkyl, long-chain alkyl, cycloalkyl, halogen alkyl, at least partially halogenated long-chain alkyl, halogen cycloalkyl, aryl, arylene, halogen aryl, heteroaryl, heteroarylene, heterocyclic alkylene, heterocycloalkyl, halogen heteroaryl, alkenyl, halogen alkenyl, alkynyl, halogen alkynyl, ketoaryl, halogen ketoaryl, ketoheteroaryl, ketoalkyl, halogen ketoalkyl, ketoalkenyl, halogen ketoalkenyl, halogen alkyl aryl, and halogen alkyl heteroaryl, wherein, for suitable groups, one or a number of non-adjacent CH2 groups can be replaced by —O—, —S—, —NH—, —NR ∘∘∘ —, —SiR ∘ R ∘∘ —, —CO—, —COO—, —COR ∘ OR ∘∘ —, —OCO—, —OCO—O—, —SO2-, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1=CY2 or —C≡C— independently from one another, and in such a way that O and/or S atoms are not directly bonded to one another, and are replaced optionally with aryl- or heteroaryl preferably containing between 1 and 30 C atoms (terminal CH3 groups are understood to be CH2 groups in the sense of CH2-H). The invention further relates to the use of a zinc complex as a p-dopant in charge generation layers.

First claim

The invention claimed is:

1. An organic electronic component having
at least one charge carrier generation layer which has an organic p-doped region containing a zinc complex as the p-dopant, wherein the zinc complex comprises a zinc atom and at least one ligand L of the following structure:

wherein R 1 and R 2 are, independently of one another, oxygen wherein R 1 and/or R 2 are coordinated to the zinc atom, and
R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, at least partially halogenated long-chain alkyl, halocycloalkyl, aryl, arylenes, haloaryl, heteroaryl, heteroarylenes, heterocycloalkylenes, heterocycloalkyl, halogen-heteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl, haloalkyl heteroaryl, wherein one or more non-adjacent CH 2 groups can be replaced independently of one another by —O—, —S—, —NH—, —NR ∘∘∘ —, —SiR ∘ R ∘∘ —, —CO—, —COO—, —COR ∘ OR ∘∘ —, —OCO—, —OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1=CY2 or —C≡C— in such a way that O and/or S atoms are not directly connected to one another, likewise optionally substituted with aryl or heteroaryl.

2. The component according to claim 1 , wherein R 3 is selected from the group consisting of haloalkyl, halogen-aryl, at least partially halogenated long-chain alkyl, halogen-cycloalkyl, haloheteroaryl, haloalkylaryl and haloalkyl heteroaryl.

3. The component according to claim 1 , wherein R 3 is a perfluorinated hydrocarbon radical.

4. The component according to claim 1 , wherein R 3 has the following general formula:
*—(CF 2 ) n CF 3

wherein n can assume the values from 0 to 19.

5. The component according to claim 1 , wherein R 3 is selected from the group consisting of:

wherein Y 1 -Y 5 are selected independently of one another from the group consisting of: C—H, C-D, C—F, C—NO 2 , C—CN, C-halogen, C-pseudohalogen, N or C—C n F 2n+1 , where n=1 to 10.

6. An organic electronic component having a zinc complex as a p-type dopant in charge carrier generation layers containing a zinc atom and at least one ligand L of the following structure:

herein R 1 and R 2 are, independently of one another, oxygen, sulfur, selenium, NH or NR 4 , wherein R 1 and/or R 2 are coordinated to the zinc atom, wherein R 4 is selected from the group consisting of alkyl or aryl and can be connected to R 3 ; and R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, at least partially halogenated long-chain alkyl, halocycloalkyl, aryl, arylenes, haloaryl, heteroaryl, heteroarylenes, heterocycloalkylenes, heterocycloalkyl, halogen-heteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl, haloalkyl heteroaryl, wherein one or more non-adjacent CH 2 groups can be replaced independently of one another by —O—, —S—, —NH—, —NR ∘∘∘ —, —SiR ∘ R ∘∘ —, —CO—, —COO—, —COR ∘ OR ∘∘ —, —OCO—, —OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1=CY2 or —C≡C— in such a way that O and/or S atoms are not directly connected to one another, likewise optionally substituted with aryl or heteroaryl.

7. The component according to claim 1 , wherein the organic p-doped region comprises an organic hole-conducting matrix, into which the p-type dopant is introduced.

8. The component according to claim 1 , wherein the proportion of the zinc complex relative to the p-doped region is ≥0.1% by volume to ≤50% by volume.

9. The component according to claim 1 , wherein the charge carrier generation layer additionally has an n-conducting region.

10. The component according to claim 9 , wherein an intermediate region is arranged between the n-conducting region and the organic p-doped region.

11. The component according to claim 10 , wherein the intermediate region is designed as an intermediate layer and has a thickness of 0.5 nm to 10 nm.

12. The component according to claim 1 , wherein the n-conducting region has a common interface with the organic p-doped region.

13. The component according to claim 9 , wherein the n-conducting region is an organic n-doped region.

14. The component according to claim 13 , wherein the organic n-doped region has an organic electron-conducting matrix into which an n-type dopant is introduced.

15. The component according to claim 1 , further comprising
an anode,
a first emitter layer
a second emitter layer
a cathode,

wherein the charge carrier generation layer is arranged between the first and second emitter layers.

16. The component according to claim 15 , comprising at least one further charge carrier generation layer and at least one further emitter layer.

17. The component according to claim 6 , wherein both R 1 and R 2 are oxygen.

18. An organic electronic component according to claim 6 , in the p-doped region of a charge carrier generation layer.

19. An organic electronic component having
at least one charge carrier generation layer which has an organic p-doped region containing a zinc complex as the p-dopant, wherein the zinc complex comprises a zinc atom and at least one ligand L of the following structure:

wherein R 1 and R 2 are, independently of one another, oxygen, sulfur, selenium, NH or NR 4 , wherein R 1 and/or R 2 are coordinated to the zinc atom, wherein R 4 is selected from the group consisting of alkyl or aryl and can be connected to R 3 ; and
R 3 is selected from the group consisting of alkyl, long-chain alkyl, cycloalkyl, haloalkyl, at least partially halogenated long-chain alkyl, halocycloalkyl, aryl, arylenes, haloaryl, heteroaryl, heteroarylenes, heterocycloalkylenes, heterocycloalkyl, halogen-heteroaryl, alkenyl, haloalkenyl, alkinyl, haloalkinyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, haloalkylaryl, haloalkyl heteroaryl, wherein one or more non-adjacent CH 2 groups can be replaced independently of one another by —O—, —S—, —NH—, —NR ∘∘∘ —, —SiR ∘ R ∘∘ —, —CO—, —COO—, —COR ∘ OR ∘∘ —, —OCO—, —OCO—O—, —SO 2 —, —S—CO—, —CO—S—, —O—CS—, —CS—O—, —CY1=CY2 or —C≡C— in such a way that O and/or S atoms are not directly connected to one another, likewise optionally substituted with aryl or heteroaryl.

20. The component according to claim 1 , wherein one or more non-adjacent CH 2 groups are substituted with aryl or heteroaryl, wherein the aryl or heteroaryl contain 1 to 30 C atoms.

Assignees

• Osram Oled Gmbh

Inventors

• Pentlehner Dominik
• Schmid Guenter
• Maltenberger Anna
• Pecqueur Sébastien
• Kessler Florian
• Regensburger Stefan

Classifications

• C07F3/06

  Zinc compounds · CPC title

• H01L51/5076

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic

• H01L51/506

  Electricity · mapped topic

• H01L51/5004

  Electricity · mapped topic