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Materials for organic electroluminescence devices

A conditional and group technology, applied in the direction of organic dyes, electrical solid devices, electrical components, etc., can solve the problems of strong oxidation sensitivity, damage to material preparation, purification and storage, etc.

Active Publication Date: 2012-12-12
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A disadvantage of these materials is that they are often very sensitive to oxidation, which impairs the preparation, purification and storage of said materials, as well as the long-term stability of solutions comprising said materials

Method used

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  • Materials for organic electroluminescence devices
  • Materials for organic electroluminescence devices
  • Materials for organic electroluminescence devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167]

[0168] 37.4 g (145 mmol) of 11,12-dihydroindolo[2,3-a]carbazole were added to 23 ml (159.5 mmol) of methyl 2-iodobenzoate in 150 ml of di-n-butyl ether , and degas the solution. Then 10g (158mmol) of copper powder, 1.38g (7mmol) of copper iodide (I) and 22g (159.6mmol) of K 2 CO 3 This was added to the mixture, and the mixture was stirred at 144° C. for 4 days under protective gas. Use MgSO 4 The organic phase was dried and the solvent was removed under vacuum. The residue was recrystallized from acetone and finally sublimed in high vacuum. Yield: 20.9 g (58.4 mmol), 40% of theory, 99.9% pure according to HPLC.

Embodiment 2

[0170]

[0171] By the same procedure as in Example 1, by making 37.4g (145mmol) 11,12-dihydroindolo[2,3-a]carbazole and 54g (159.5mmol) 3-iodobiphenyl-2- Carboxylic acid methyl ester reaction synthesis of the compound. Convert the residue from CH 2 Cl 2 / isopropanol for recrystallization, and finally sublimation in high vacuum. Yield: 24.5 g (56 mmol), 39% of theory, 99.9% pure according to HPLC.

Embodiment 3

[0173]

[0174] By the same procedure as in Example 1, by making 37.4g (145mmol) of 11,12-dihydroindolo[2,3-a]carbazole and 42g (159.5mmol) of 3-iodothiophene-2-carboxyl Acid methyl ester reaction synthesizes said compound. Convert the residue from CH 2 Cl 2 / isopropanol for recrystallization, and finally sublimation in high vacuum. Yield: 22.6 g (62 mmol), 43% of theory, 99.9% pure according to HPLC.

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Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescence devices.

Description

technical field [0001] The present invention relates to materials for use in electronic devices, in particular in 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) in which organic semiconductors are utilized as functional materials are described. 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, it is possible to achieve up to a four-fold increase in energy and power efficiency using organometallic compounds as phosphorescent emitters. However, there is still a need for improvements in OLEDs in general, and in particular OLEDs exhibiting triplet emission (phosphorescence), eg improvements in efficiency, operating voltage and lifetime. This applies in particular to ligh...

Claims

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Application Information

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IPC IPC(8): C07D471/16C07D471/22C07D487/06C07D487/16C07D487/20C07D487/22C07D495/22C07D513/16C07D513/22C07F7/10C07F9/6584H01L51/50
CPCC07D495/22C07F7/0814C07D471/16C07D487/16H01L51/0072C09B57/007C09B57/10C09B57/00C07D487/06C07D471/22H01L51/5012H01L51/5016C07D487/22C07D513/16C07D513/22C07D487/20C07F9/65848Y02E10/549H10K85/6572H10K50/11H10K2101/10H10K50/18H10K50/181H10K85/657H10K50/15H10K50/16
Inventor 埃米尔·侯赛因·帕勒姆克里斯托夫·普夫卢姆特雷莎·穆希卡-费尔瑙德
Owner MERCK PATENT GMBH
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