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Materials for Organic Electroluminescent Devices

A compound, general formula technology, applied in the field of organic semiconductors, can solve the problems of high technical complexity and instability of OLED manufacturing

Active Publication Date: 2011-12-14
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds are generally unstable under thermal load and cannot be evaporated without decomposition, which requires high technical complexity for OLED production and thus represents an industrial disadvantage

Method used

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  • Materials for Organic Electroluminescent Devices
  • Materials for Organic Electroluminescent Devices
  • Materials for Organic Electroluminescent Devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] Embodiment 1: Synthesis of 2,11-bis(naphthalene-1-yl)benzo[c]phenanthrene

[0159] a) Synthesis of two p-bromobenzylidene acetone

[0160]

[0161] 296g (1600mmol) p-bromobenzaldehyde was added dropwise to the solution of 52.8g (800mmol) potassium hydroxide (85%) and 58.9ml (800mmol) acetone in 1.6L water and 2L ethanol, and the mixture was Stir overnight at room temperature. The precipitated solid was filtered off with suction, washed with 3 L of water and dried under vacuum. Yield: 284 g (826 mmol), 91%.

[0162] b) Synthesis of 1,5-bis(p-bromobenzyl)pentan-3-one

[0163]

[0164] 217g (555mmol) of di-p-bromobenzylideneacetone was suspended in 20ml of glacial acetic acid in a solution of 1L of ethyl acetate, 14g of Pd / C (5%) was added, and the mixture was placed in a 2.8L autoclave at 4 Bar H 2 Stir under pressure. When the hydrogen absorption was complete (about 30 minutes), the mixture was 2 Stir under pressure for an additional 2 hours. Filter to remo...

Embodiment 2

[0178] Example 2: Synthesis of 9-(phenyl)-10-(benzo[c]phenanthrene-5-yl)anthracene

[0179] a) Synthesis of benzo[c]phenanthrene-5-boronic acid

[0180]

[0181] 52ml (130mmol) of n-butyllithium (2.5M in n-hexane) was added dropwise to a suspension of 30.7g (100mmol) of 5-bromobenzo[c]phenanthrene in 1000ml of THF at -78°C under vigorous stirring solution, and the mixture was stirred for an additional 2 hours. 16.7ml (150mmol) trimethyl borate was added to the red solution in one portion under vigorous stirring, the mixture was stirred at -78°C for another 30 minutes, then warmed to room temperature within 3 hours, added 300 ml of water, and the mixture was stirred for 30 minutes. The organic phase was separated and evaporated to dryness under vacuum. The solid was dissolved in 100 ml of n-hexane, filtered with suction, washed once with 100 ml of hexane and dried under vacuum. Yield: 24.8 g (91 mmol), 91 %, about 90 % pure (NMR) boronic acid with varying amounts of bori...

Embodiment 3

[0185] Example 3: Synthesis of 9-(naphthalene-2-yl)-10-(benzo[c]phenanthrene-5-yl)anthracene

[0186]

[0187] 913 mg (3 mmol) tri-o-tolylphosphine, and then 112 mg (0.5 mmol) palladium(II) acetate were added to vigorously stirred 19.2 g (50 mmol) 9-bromo-10-(2-naphthyl)anthracene, 14.9 g ( 55mmol) benzo [c] phenanthrene-4-boronic acid and 25.5g (120mmol) tripotassium phosphate in 300ml toluene, 100ml di a suspension in a mixture of alkanes and 400 ml of water, and the mixture was then heated at reflux for 16 hours. After the mixture had cooled, the precipitated solids were filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), and three times with 100 ml of ethanol. / g) was recrystallized three times. Yield: 15.3 g (29 mmol), 58.8%, purity 99.9% (HPLC).

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Abstract

The present invention relates to substituted benzo[c]phenanthrene derivatives and to the production and to the use thereof in electronic devices, and to the electronic devices themselves. The present invention relates in particular to benzo[c]phenanthrene derivatives substituted with at least one aromatic unit or at least one diarylamino unit.

Description

technical field [0001] The present invention relates to organic semiconductors, their preparation and their use in organic electronic devices. Background technique [0002] Organic semiconductors are being developed for many different types of electronic applications. The structure of organic electroluminescent devices (OLEDs) in which these organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. However, further improvements are still desired to use these devices in high quality and long-life displays. In particular, therefore, the lifetime and efficiency of blue-emitting organic electroluminescent devices currently still represent a problem, for which improvements are still required. Furthermore, it is necessary that the compounds have high thermal stability and a high glass transition temperature and that they can be sublimated without decomposition. A high glass transition temperature is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09K2211/1433C09K2211/1466C09K11/06C09K2211/1007C09B3/78C09K2211/1416H05B33/14C09B57/00C09B57/008C09B1/00C09K2211/1011C09B3/02Y02E10/549H10K85/622H10K85/626H10K85/633H10K85/6572
Inventor 埃米尔·侯赛因·帕勒姆阿尔内·比辛霍尔格·海尔菲利普·施特塞尔
Owner MERCK PATENT GMBH
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