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A kind of bibenzimidazole derivative, its preparation method and its application

A technology of benzimidazole and derivatives, applied in the field of organic electroluminescence, can solve the problems of low glass transition temperature, shortened device life, small molecular weight, etc., and achieves improved luminous efficiency, lower lighting voltage, and high glass state transition. effect of temperature

Active Publication Date: 2017-10-10
GUAN ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This material has a higher triplet energy level, which can be well matched with phosphorescent dyes. However, due to the low molecular weight of the material (molecular weight 484), the glass transition temperature is low (Tg below about 1100 ° C), and it is easy to use during use. Crystallization, forming an island shape, causing no bright spots, and shortening the life of the device

Method used

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  • A kind of bibenzimidazole derivative, its preparation method and its application
  • A kind of bibenzimidazole derivative, its preparation method and its application
  • A kind of bibenzimidazole derivative, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of intermediate 1-(4-bromophenyl)-1H-benzo[d]imidazole

[0037]

[0038] 500 ml one-necked bottle, equipped with a magnetic stirrer, add 9.5 g of 1H-benzo[d] imidazole (molecular weight 118, 0.08 mol), p-bromoiodobenzene 28.2 g (molecular weight 282, 0.1 mol), CuI dosage 1.5 g (molecular weight 190, 0.0079mol), potassium carbonate 20.7g (molecular weight 138, 0.15mol), DMF 200ml, piperidine-2-carboxylic acid 2.1g (molecular weight 129, 0.016mol). After argon replacement, stir and reflux, monitor the reaction with TLC, the reaction is complete after 3 hours, lower the temperature, add 200ml of water, the product precipitates, filter, wash with water repeatedly, the product is finally purified by column chromatography, and eluted with ethyl acetate / petroleum ether to obtain 15g Compound 1-(4-bromophenyl)-1H-benzo[d]imidazole, molecular weight 272, yield 68.5%.

Embodiment 2

[0040]Synthesis of parent 1,1'-bis(4-bromophenyl)-1H,1'H-2,2'-bibenzo[d]imidazole (reference: Org.Biomol.Chem.,2010,8,326- 330)

[0041]

[0042] Add 1-(4-bromophenyl)-1H-benzo[d]imidazole 13.6g (molecular weight 272, 0.05mol), 200ml xylene, copper acetate 1.8g (molecular weight 181, 0.01mol) in a 500ml three-necked flask, Install the air duct, and air is slowly introduced during the reflux period, pay attention to adding xylene solvent, reflux and stir, monitor the reaction with TLC, the reaction is completed in about 12 hrs, and cool to room temperature. The xylene was distilled off and purified by column chromatography to obtain 11.9 g of a solid product with a molecular weight of 542 and a yield of 87.5%.

Embodiment 3

[0044] Synthesis of parent 5,5'-dibromo-1,1'-diphenyl-1H,1'H-2,2'-bibenzo[d]imidazole

[0045] The synthesis steps are the same as the previous 1 and 2, except that in the first step, 1H-benzo[d]imidazole is changed to 5-bromo-1H-benzo[d]imidazole, p-bromoiodobenzene is changed to iodobenzene, other reagents In the second step, use the monobromide synthesized in the first step here, other reagents and reaction conditions remain unchanged, and obtain the target parent 5,5'-dibromo-1,1'-diphenyl Base-1H,1'H-2,2'-bibenzo[d]imidazole. The reaction pathway is as follows:

[0046]

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Abstract

The invention relates to a bibenzimidazole derivative. The structure of the bibenzimidazole derivative is represented by formula (1). The bibenzimidazole derivative can be used to prepare the phosphorescence host material and / or electron transfer material of electroluminescent devices in order to reduce the driving voltage of the devices, improve the luminescence efficiency of the devices and prolong the service life of the devices.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a bibenzimidazole derivative, a preparation method thereof, and an application thereof in electron transport materials. Background technique [0002] After years of research and development, electroluminescent materials and devices have reached the practical level, and various materials, such as hole materials, electronic materials, light-emitting materials, and display device preparation technologies, have made great progress. With the deepening of research work and the requirements for materials in the process of practical application, the advantages of using phosphorescence as a light-emitting material are becoming more and more obvious. The luminous efficiency of phosphorescent materials is 3 to 4 times higher than that of fluorescent materials. For many display products that require higher brightness, phosphorescent materials are the first choice. The p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D235/20C07D409/14C07D405/14C07D519/00C07D401/14H01L51/54
Inventor 范洪涛李银奎李艳蕊任雪艳
Owner GUAN ETERNAL MATERIAL TECH
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