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Novel materials for organic electroluminescent devices

A group and general formula technology, applied in the field of organic electroluminescent devices, can solve problems that have not been raised

Active Publication Date: 2012-05-23
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No use of these compounds in organic electronic devices has been proposed

Method used

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  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0179] Embodiment 1: the synthesis of 8-bromobenzo [a] anthracene

[0180]

[0181] 200ml of hypophosphorous acid (50%) was added to a suspension of 75g (200.2mmol) 8-bromobenzo[a]anthracene-7,12-dione in 900ml of glacial acetic acid, and 400ml of hydroiodic acid (57%) was added dropwise . The reaction mixture was heated to reflux for 16 hours. After cooling, the precipitated solid was filtered off with suction and washed with 500 ml each of water, ethanol / water (1:1, v / v) and ethanol. The crude product was washed by boiling in ethanol and then recrystallized from toluene / glacial acetic acid (1:1, v / v, about 15 ml / g). Drying yielded 35.8 g (115.4 mmol) of 57.6% product with a purity of 99%.

Embodiment 2

[0182] Embodiment 2: Synthesis of benzo [a] anthracene-8-boronic acid

[0183]

[0184] 52ml (130mmol) of n-butyllithium (2.5M in n-hexane) was added dropwise under vigorous stirring at -78°C to a suspension of 30.7g (100mmol) of 8-bromobenzanthracene in 1000ml of tetrahydrofuran. The mixture was stirred for another 2h. 16.7 ml (150 mmol) trimethyl borate was added in one portion to the red solution under vigorous stirring, the mixture was stirred at -78 °C for an additional 30 minutes, then allowed to warm to room temperature over 3 h, and added 300ml of water, and the mixture was stirred for 30 minutes. The organic phase was separated off 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. Boronic acid yield: 23.7 g (87 mmol), 87%, about 90% pure (NMR), with varying amounts of boric anhydride and boric acid. Boronic acid can be used in this form without ...

Embodiment 5

[0187] Example 5: Synthesis of 9-(naphthalene-2-yl)-10-(benzo[a]anthracene-8-yl)anthracene

[0188]

[0189] Add 913mg (3mmol) of tri-o-tolylphosphine, then 112mg (0.5mmol) of palladium(II) acetate into well-stirred 19.2g (50mmol) of 9-bromo-10-(2-naphthyl)anthracene, 15.0g (55mmol ) benzo[a]anthracene-8-boronic acid, 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 heated to reflux for 16 hours. After cooling, the precipitated solid was 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, which was removed from chlorobenzene ( about 10ml / g), recrystallized three times, then sublimed twice (p=5×10 -5 mbar, T=340°C). Yield: 14.8 g (27.5 mmol), 55.0%, purity 99.9% (HPLC).

[0190] The following compounds according to the invention (Examples 6 to 11) were obtained analogou...

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Abstract

The present invention relates to substituted benz[a]anthracene derivatives, to the preparation thereof and to the use thereof in organic electroluminescent devices, as well as to electroluminescent devices, especially blue-emitting devices, in which said compounds are used as matrix material or doping agent in the emitting layer and / or as hole transport material and / or as electron transport material.

Description

technical field [0001] The present invention relates to substituted benz[a]anthracene derivatives, their preparation and their use in electronic devices, the invention also relates to electronic devices, in particular blue-emitting organic electroluminescent devices, in which these compounds are used as emitting layers host material or dopant in and / or as hole transport material and / or as electron transport material. 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 necessary before these devices can be used in high-quality and long-lived displays. Thus, in particular, the insufficient lifetime and insufficient efficiency of current blue-emitting org...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/28C07C15/62C07C211/54C07C211/61H05B33/14H01L51/00H10K99/00
CPCC09K2211/1011H01L51/5012C09B57/008H01L51/0067H01L51/5048C07C15/28C07C2103/40C07C211/61C09B3/78C09B57/00C07C15/62H05B33/14C09K11/06C09B1/00H01L51/0054C09B6/00C07C211/60Y02E10/549H01L51/0058C07C2603/40H10K85/622H10K85/626H10K85/654H10K50/14H10K50/11
Inventor 埃米尔·侯赛因·帕勒姆阿尔内·比辛霍尔格·海尔菲利普·施特塞尔迈克尔·赫尔巴赫
Owner MERCK PATENT GMBH
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