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Compound containing imidazopyridine group and application thereof in organic electroluminescence

A technology of pyridine groups and electroluminescent devices, applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of shortened device life, small molecular weight, no bright spots, etc., and achieve high glass transition temperature and good thermal stability , The effect of improving the service life

Inactive Publication Date: 2015-05-27
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The material has a higher triplet energy level, which can be well matched with phosphorescent dyes, but due to the material's small molecular weight (molecular weight 484), the glass transition temperature is low (Tg is about 1100C or below), 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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  • Compound containing imidazopyridine group and application thereof in organic electroluminescence
  • Compound containing imidazopyridine group and application thereof in organic electroluminescence
  • Compound containing imidazopyridine group and application thereof in organic electroluminescence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of compounds of the following formula

[0034]

[0035] first step,

[0036]

[0037] In a 50ml flask, add 0.892g (5mmol) of 2-amino-5-bromopyridine, 1.7g of 2-bromo-2-phenylacetophenone (6mmol), 0.491g (6mmol) of sodium bicarbonate, isopropyl 15ml of alcohol, reflux and stir for 12hrs, distill off isopropanol, add 30ml of isopropanol and 60ml of dichloromethane, collect the organic phase, separate the product by column chromatography, rinse with petroleum ether and ethyl acetate, 3:1 ratio. Obtained 1.17g, 67% yield, mp=198-1990C.

[0038] second step,

[0039]

[0040] In a 500ml three-neck flask equipped with magnetic stirring and protected by Ar gas, add 14.9g of 2,3-diphenyl-6-bromoimidazo[1,2,a]pyridine (molecular weight 348, 0.0428mol) and 120ml of THF, cool to -78°C, add 25ml of 2M nBuLi (0.05mol) dropwise, keep the temperature at -78°C, stir for 10min, then add 30ml of B(OiPr) dropwise at -78°C 3 (0.153mol), stirred to room temperature an...

Embodiment 2

[0046] Synthesis of compound 1

[0047] The synthetic process is divided into two steps, and the first step is the same as the first step in Example 1, except that 2-bromo-2-phenyl-1-(p-bromophenyl)ethanone is used to replace 2-bromo-2-phenylbenzene Ethanone is used as a raw material, and other raw materials and processes are unchanged to obtain a dibromo intermediate; the synthesis of the second step is the same as the third step of Example 1, except that 2,3-diphenylimidazo[1,2 , a] Pyridine-6-boronic acid is replaced by N-phenylcarbazole-3-boronic acid, and 3,5-bis(carbazol-9-yl)bromobenzene is replaced by 2-(p-bromophenyl)-3-benzene Base-6-bromoimidazo[1,2,a]pyridine, and other raw materials and processes remain unchanged, to obtain compound 1.

[0048] Product MS (m / e): 752, elemental analysis (C 55 h 36 N 4 ): theoretical value C: 87.74%, H: 4.82%, N: 7.44%; measured value C: 87.75%, H: 4.84%, N: 7.41%.

Embodiment 3

[0050] Synthesis of Compound 2

[0051] The synthesis process is divided into two steps, the first step is the same as the first step in Example 1, just replace 2-bromo-2-phenylacetophenone with 2-bromo-2-(p-bromophenyl)acetophenone as raw material , other raw materials and processes remain unchanged to obtain a dibromo intermediate; the synthesis of the second step is the same as the third step of Example 1, except that the 2,3-diphenylimidazo[1,2,a]pyridine -6-boronic acid for N-phenylcarbazole-3-boronic acid and 3,5-bis(carbazol-9-yl)bromobenzene for 2-phenyl-3-(p-bromophenyl)-6- Bromoimidazo[1,2,a]pyridine, the other raw materials and processes remain unchanged to obtain compound 2.

[0052] Product MS (m / e): 752, elemental analysis (C 55 h 36 N 4 ): theoretical value C: 87.74%, H: 4.82%, N: 7.44%; measured value C: 87.72%, H: 4.86%, N: 7.42%.

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Abstract

The invention provides a novel organic compound having a structure as shown in a formula (I). In the compound, Ar is one of single bond, substituted or unsubstituted aromatic or hetero aromatic group of C6-C30, and substituted or unsubstituted condensed aromatic or condensed hetero aromatic group of C4-C30, and the number of substituent groups on Ar is 2-4; R1 and R2 are respectively and independently selected from H, substituted or unsubstituted aliphatic alkyl of C1-C12, substituted or unsubstituted aliphatic naphthenic base of C1-C12, and substituted or unsubstituted aryl or heterocyclic aryl of C6-C30; Ar1 is selected from substituted or unsubstituted aliphatic alkyl of C1-C12 or substituted or unsubstituted aryl of C6-C30; and n and m are respectively 1 or 2. The compound is stable in property and simple in preparation process, and can be used as a phosphorescence host material in an organic electroluminescence device to obtain relatively high luminescence efficiency and relatively low turn-on voltage.

Description

technical field [0001] The invention relates to a novel organic compound and its application in the technical field of organic electroluminescence display. 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 phosphorescent light-emitting layer in the device is formed by co-evaporation of tw...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1044H10K85/6572H10K50/11
Inventor 李银奎李艳蕊范洪涛
Owner BEIJING ETERNAL MATERIAL TECH
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