公开(公告)号：US10581001B2

公开(公告)日：2020-03-03

申请号：US15763068

申请日：2016-09-27

Applicant: OSRAM OLED GmbH

Inventor： Dominik Pentlehner ,  Guenter Schmid ,  Anna Maltenberger ,  Sébastien Pecqueur ,  Florian Kessler ,  Stefan Regensburger

IPC: H01L51/00 ,  C07F3/06 ,  H01L33/14 ,  H01L51/52 ,  H01L51/50

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 (5a) 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.

公开(公告)号：US09929362B2

公开(公告)日：2018-03-27

申请号：US14406307

申请日：2013-05-14

Applicant: SIEMENS AKTIENGESELLSCHAFT ,  OSRAM OLED GmbH

Inventor： Anna Maltenberger ,  Sébastien Pecqueur ,  Guenter Schmid ,  Jan Hauke Wemken

IPC: H01L51/42 ,  H01L51/00 ,  H01L51/50

CPC classification number: H01L51/009 ,  H01L51/42 ,  H01L51/506 ,  Y02E10/549

Abstract: A bi- or polynuclear metal complex of a metal of groups Vb/VIb/VIIb (IUPAC groups 5-7), has a ligand of the structure (a), wherein R1 and R2, independently of each other, can be oxygen, sulfur, selenium, NH, or NR4, wherein R4 is selected from alkyls and aryls and can be bonded to R3; and R3 is selected from alkyls, long-chain alkyls, alkoxys, long-chain alkoxys, cycloalkyls, haloalkyls, aryls, arylenes, haloaryls, heteroaryls, heteroarylenes, heterocycloalkylenes, heterocycloalkyls, haloheteroaryls, alkenyls, haloalkenyls, alkynyls, haloalkynyls, ketoaryls, haloketoaryls, ketoheteroaryls, ketoalkyls, haloketoalkyls, ketoalkenyls, haloketoalkenyls, where one or more non-adjacent CH2 groups can be replaced, independently, with (1) —O—, —S—, —NH—, —NR∘—, —SiR∘R∘∘—, —CO—, —COO—, —OCO—, —OCO—O—, —SO2-, —S—CO—, —CO—S—, —CY1=CY2, or —C≡O— in such a way that O and/or S atoms are not bonded directly to each other, or (2) aryls or heteroaryls containing 1 to 30 C atoms, as a p-type doping agent for matrix materials of electronic components.

公开(公告)号：US20150162534A1

公开(公告)日：2015-06-11

申请号：US14406307

申请日：2013-05-14

Applicant: SIEMENS AKTIENGESELLSCHAFT ,  OSRAM OLED GMBH

Inventor： Anna Maltenberger ,  Sébastien Pecqueur ,  Guenter Schmid ,  Jan Hauke Wemken

IPC: H01L51/00

CPC classification number: H01L51/009 ,  H01L51/42 ,  H01L51/506 ,  Y02E10/549

Abstract: A bi- or polynuclear metal complex of a metal of groups Vb/VIb/VIIb (IUPAC groups 5-7), has a ligand of the structure (a), wherein R1 and R2, independently of each other, can be oxygen, sulfur, selenium, NH, or NR4, wherein R4 is selected from alkyls and aryls and can be bonded to R3; and R3 is selected from alkyls, long-chain alkyls, alkoxys, long-chain alkoxys, cycloalkyls, haloalkyls, aryls, arylenes, haloaryls, heteroaryls, heteroarylenes, heterocycloalkylenes, heterocycloalkyls, haloheteroaryls, alkenyls, haloalkenyls, alkynyls, haloalkynyls, ketoaryls, haloketoaryls, ketoheteroaryls, ketoalkyls, haloketoalkyls, ketoalkenyls, haloketoalkenyls, where one or more non-adjacent CH2 groups can be replaced, independently, with (1) —O—, —S—, —NH—, —NR°—, —SiR°R°°—, —CO—, —COO—, —OCO—, —OCO—O—, —SO2-, —S—CO—, —CO—S—, —CY1=CY2, or —C≡O— in such a way that O and/or S atoms are not bonded directly to each other, or (2) aryls or heteroaryls containing 1 to 30 C atoms, as a p-type doping agent for matrix materials of electronic components.

Abstract translation: Vb / VIb / VIIb族金属的双或多核金属络合物（IUPAC基团5-7）具有结构（a）的配体，其中R 1和R 2彼此独立地可以是氧，硫 ，硒，NH或NR4，其中R4选自烷基和芳基并且可以键合到R3; 并且R 3选自烷基，长链烷基，烷氧基，长链烷氧基，环烷基，卤代烷基，芳基，亚芳基，卤代芳基，杂芳基，杂芳基，杂环亚烷基，杂环烷基，卤代杂芳基，烯基，卤代烯基，炔基，卤代炔基，酮基芳基，卤代芳基 ，酮基芳基，酮基烷基，卤代烷基，酮链烯基，卤代烯基，其中一个或多个不相邻的CH 2基团可以独立地被（1）-O - ， - S - ， - NH - ， - NRO - ， - SiR R 0 - ， - CO-，-COO-，-OCO-，-OCO-O-，-SO2-，-S-CO-，-CO-S-，-CY1 = CY2或-C≡O- 使O和/或S原子彼此不直接键合，或（2）含有1至30个C原子的芳基或杂芳基作为电子元件基质材料的p型掺杂剂。