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Organic electroluminescence devices

A technology of electronic devices and general formulas, applied in the field of materials for organic electroluminescent devices, can solve problems affecting material preparation, unfavorable, strong oxidation sensitivity, etc.

Active Publication Date: 2013-01-09
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These substances have the disadvantage that their oxidation sensitivity is often very high, which can adversely affect the preparation, purification and storage of the material, as well as the long-term stability of the solutions containing the material

Method used

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  • Organic electroluminescence devices
  • Organic electroluminescence devices
  • Organic electroluminescence devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0200] Example 1a: 3-Phenyl-4H-furo[3,4-b]indole

[0201]

[0202] 45 g (123 mmol) 3-phenyl-4-(benzenesulfonyl)-4H-furo[3,4-b]indole and 48 g (856 mmol) potassium hydroxide in 65 ml DMSO and 21 ml water were heated under reflux 1 hour. The mixture was then cooled to room temperature, neutralized with 1M HCl solution and extracted with dichloromethane. The solvent was evaporated under vacuum and the residue was purified by chromatography (heptane / ethyl acetate 10:1). Yield: 22.4 g (96 mmol), 80%.

[0203] The following compounds are similarly obtained:

[0204]

Embodiment 2a

[0205] Example 2a: 2-Bromophenyl-(3-phenylfuro[3,4-b]indol-4-yl)methanone

[0206]

[0207] 2.1 g (52.5 mmol) NaH (60% in mineral oil) were dissolved in 500 ml THF under a protective atmosphere. 11.5 g (50 mmol) of 3-phenyl-4H-furo[3,4-b]indole and 11.5 g (52.5 mmol) of 15-crown-5 dissolved in 200 ml of THF were added. After 1 hour at room temperature, a solution of 12 g (55 mmol) of 2-bromobenzoyl chloride in 250 ml of tetrahydrofuran was added dropwise. The reaction mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was poured onto ice and extracted three times with dichloromethane. Use Na 2 SO 4 The combined organic phases were dried and evaporated. The residue was extracted with hot toluene and recrystallized from toluene / n-heptane. Yield was 12 g (60%).

[0208] The following compounds are similarly obtained:

[0209]

[0210]

Embodiment 2i

[0211] Example 2i: (1-Chlorobenzo[4,5]furo[3,2-b]indol-10-yl)phenyl ketone

[0212]

[0213] 2.1 g (52.5 mmol) NaH (60% in mineral oil) were dissolved in 500 ml THF under a protective atmosphere. 12.6 g (50 mmol) of 3-phenyl-4H-furo[3,4-b]indole and 11.5 g (52.5 mmol) of 15-crown-5 dissolved in 200 ml of THF were added. After 1 hour at room temperature, a solution of 7.7 g (55 mmol) of benzoyl chloride in 250 ml of THF was added dropwise. The reaction mixture was then stirred at room temperature for 18 hours. After this time, the reaction mixture was poured onto ice and extracted three times with dichloromethane. Use Na 2 SO 4 The combined organic phases were dried and evaporated. The residue was extracted with hot toluene and recrystallized from toluene / n-heptane. Yield was 12.5 g (69%).

[0214] The following compounds are similarly obtained:

[0215]

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Abstract

The present invention relates to electronic devices, in particular to organic electroluminescence devices, comprising compounds according to formula (1), and to the corresponding compounds.

Description

technical field [0001] The present invention relates to electronic devices, in particular to organic electroluminescent devices, and to materials for electronic devices, in particular to materials for organic electroluminescent devices. Background technique [0002] For example in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136, structures of organic electroluminescent devices (OLEDs) are described in which organic semiconductors are used as functional materials. The luminescent materials used here are increasingly organometallic complexes that exhibit phosphorescence rather than fluorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). For quantum mechanical reasons, up to four times higher energy and power efficiencies can be achieved using organometallic compounds as phosphorescent emitters. In general, however, improvements are still required in the case of OLEDs, especially also in the case of OLEDs showing triplet emission (phosphorescence), for example in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D471/14C07D471/16C07D471/22C07D487/04C07D495/14C07D513/04C07D513/14C07D513/16C09K11/06H10K99/00
CPCC07D495/14C09K2211/1011H01L51/5012C09B57/00C09K2211/1007C09K11/06C09B21/00C07D471/04H01L51/5096C07D471/22C09K2211/1044C07D513/16C09K2211/1092C07F5/025H01L51/0071C09K2211/1029C07D513/04C07F7/12C09B17/00C07D513/14C07F7/10C07D471/14C09K2211/1059C09K2211/1088H01L51/0094C07D487/04C07D471/16Y02E10/549H10K85/657H10K85/40H10K50/18H10K50/11C07F13/00H05B33/14
Inventor 埃米尔·侯赛因·帕勒姆克里斯托夫·普夫卢姆菲利普·施特塞尔阿尔内·比辛多米尼克·约斯滕
Owner MERCK PATENT GMBH
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