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Organic electroluminescent device

A technology of electronic devices and groups, applied in electroluminescent light sources, electric solid-state devices, electric light sources, etc., can solve problems such as side reactions and electrochemical instability of light-emitting devices

Active Publication Date: 2014-09-03
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These materials are in some cases electrochemically unstable, which leads to side reactions in organic electroluminescent devices

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0141] Example 1: 2-bromo-N,N-bis(biphenyl)benzylamine

[0142]

[0143] 9.7 g (0.243 mol) of 60% NaH in mineral oil were dissolved in 500 ml of dimethylformamide under protective atmosphere. 60 g (0.106 mol) of N,N-bis(4-biphenyl)amine was dissolved in 500 ml of DMF and added dropwise to the reaction mixture. After 1 hour at room temperature, a solution of 60.6 (242 mmol) 2-bromobenzyl bromide in 500 ml DMF was added dropwise. The reaction mixture was stirred at room temperature for 1 hour. Afterwards, the reaction mixture was poured onto ice and extracted three times with dichloromethane. The combined organic phases were washed with Na 2 SO 4 Dry and evaporate. The residue was extracted with hot toluene and recrystallized from toluene / n-heptane. Yield 80 g (93%).

[0144] The following compounds are similarly obtained:

[0145]

[0146]

Embodiment 2

[0147] Example 2: 5-biphenyl-4-yl-2-phenyl-5,6-dihydrophenanthridine

[0148]

[0149] Dissolve 47g (0.158mol) of 2-bromo-N,N-bisbiphenylbenzylamine in 500ml of dimethylformamide under a protective atmosphere. 17.3 g (0.075 mol) of benzyltrimethylammonium bromide and 31.28 g (0.226 mol) of potassium carbonate were added to the solution. Then add 5.08g (0.022mol) Pd(OAc) under protective gas 2 , and the mixture was stirred at 120 °C for 9 hours. Afterwards, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were washed with Na 2 SO 4 Dry and evaporate. The residue was recrystallized from n-heptane. Yield 51 g (84%).

[0150] The following compounds are similarly obtained:

[0151]

[0152]

Embodiment 3

[0153] Example 3: 5-biphenyl-4-yl-2-phenyl-6(5H)-phenanthridinone

[0154]

[0155] Dissolve 16g (0.039mol) of 5-biphenyl-4-yl-2-phenyl-5,6-dihydrophenanthridine in 300ml of dichloromethane, and add 62.13g (0.393mol) of potassium permanganate in portions to the solution, and the mixture was stirred at room temperature for two days. Afterwards, the residual potassium permanganate was filtered off, the solution was evaporated and purified by chromatography (eluent: heptane / dichloromethane, 5:1). The residue was recrystallized from n-heptane. Yield 14 g (88%).

[0156] The following compounds are similarly obtained:

[0157]

[0158]

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Abstract

The present invention relates to electronic devices, in particular organic electroluminescent devices, containing compounds according to formula (1), the corresponding compounds, and a method for preparing said compounds.

Description

technical field [0001] The present invention relates to electronic devices, in particular organic electroluminescent devices, to materials for use in electronic devices, in particular in organic electroluminescent devices, and to methods of preparing these materials. Background of the invention [0002] The structure of organic electroluminescent devices (OLEDs) in which an organic semiconductor is used as functional material is described, for example, in US4539507, US5151629, EP0676461 and WO98 / 27136. The luminescent materials used here are increasingly organometallic complexes that exhibit phosphorescence rather than fluorescence. For quantum mechanical reasons, up to four times higher quantum and power efficiencies can be achieved using organometallic compounds as phosphorescent emitters. In the case of OLEDs, in particular OLEDs which also exhibit triplet emission (phosphorescence), improvements are generally still required, for example with respect to efficiency, opera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/14C07D471/16C07D471/06H10K99/00
CPCC07D495/22C07D495/06C09K2211/1044C07D405/10H01L51/0061H01L51/0058C07D491/22H01L51/0094C07D491/04C07D401/14C07D401/04C09K2211/1037C09K2211/1088C07D405/04H01L51/0072C07D491/06C09K2211/1007C07D471/06C07D471/22C07D413/10C09K11/06C09K2211/1059C07D417/04H01L51/0067C07D221/20C07D221/10C07D221/18C07D495/04C09K2211/1033C07D471/14C09K2211/1092C07D405/14H01L51/0073H01L51/0074H05B33/10C07D471/04C09K2211/1014H01L51/0071C07D401/10C09K2211/1029C09K2211/1011Y02E10/549H10K85/626H10K85/40H10K85/636H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576
Inventor 埃米尔·侯赛因·帕勒姆克里斯托夫·普夫卢姆安雅·雅提斯奇托马斯·埃伯利菲利普·斯托塞尔
Owner MERCK PATENT GMBH
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