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Fluorene Derivatives Containing Aromatic Amino Groups and Their Applications in Electroluminescent Devices

A technology of electroluminescent devices and fluorene derivatives, applied in the field of new organic compounds, can solve the problems of shortened device life, small molecular weight, no bright spots, etc., and achieve increased glass transition temperature, good thermal stability, and improved service life Effect

Active Publication Date: 2017-09-01
BEIJING 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 small molecular weight of the material (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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  • Fluorene Derivatives Containing Aromatic Amino Groups and Their Applications in Electroluminescent Devices
  • Fluorene Derivatives Containing Aromatic Amino Groups and Their Applications in Electroluminescent Devices
  • Fluorene Derivatives Containing Aromatic Amino Groups and Their Applications in Electroluminescent Devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of compound 1

[0056] first step,

[0057]

[0058] In a 500 ml three-necked flask equipped with electric stirring and protected by Ar gas, 16.9 g of diphenylamine (molecular weight 169, 0.10 mol), 44 g of 2-bromo-7-iodo-9,9-dimethylfluorene (molecular weight 398 , 0.11mol), copper powder 15g (molecular weight 64, 0.234mol), potassium carbonate 41.4g (molecular weight 138, 0.3mol), 18-crown-6 with 6.13g (molecular weight 264, 0.023mol), add solvent o-dichlorobenzene 300ml in total. Stir at reflux for 4 hours and monitor the reaction by TLC. After the reaction was complete, it was naturally stirred to room temperature, and the solvent was distilled off. The solid mixture was separated by silica gel column chromatography to obtain 40.3 g of a slightly yellow monobromo intermediate with a molecular weight of 439, a purity of 97.5%, and a yield of 89.4%.

[0059] second step,

[0060]

[0061] 1000 ml three-necked flask equipped with magnetic stirring,...

Embodiment 2

[0063] Synthesis of compound 2

[0064] The synthesis process is divided into two steps. The first step reaction is the same as the first step in Example 1, with 1-naphthylaniline instead of diphenylamine as raw material, and other reagents and processes remain unchanged to obtain the corresponding monobromine intermediate; the second step reaction is the same as in Example 1 No. In the second step, the monobromo intermediate synthesized in the first step is used to replace the monobromo intermediate in Example 1, and the other reagents and processes remain unchanged to obtain compound 2.

[0065] Product MS (m / e): 679, elemental analysis (C 50 h 37 N 3 ): theoretical value C: 88.33%, H: 5.49%, N: 6.18%; measured value C: 88.30%, H: 5.48%, N: 6.22%.

Embodiment 3

[0067] Synthesis of compound 3

[0068] The synthesis process is divided into two steps. The first step reaction is the same as the first step in Example 1 to obtain the corresponding monobromine intermediate; the second step reaction is the same as in the second step of Example 1, replacing the bromine intermediate synthesized in the first step with the bromine intermediate in Example 1 A bromo intermediate, with 2,3-diphenylimidazo[1,2,a]pyridine-7-boronic acid instead of 2,3-diphenylimidazo[1,2,a]pyridine-6-boronic acid, Other reagents and processes remained unchanged to obtain compound 3. Product MS (m / e): 629, elemental analysis (C 46 h 35 N 3 ): theoretical value C: 87.73%, H: 5.60%, N: 6.67%; measured value C: 87.70%, H: 5.61%, N: 6.69%.

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Abstract

The present invention provides a fluorene derivative containing an arylamine group, which has a structure shown in formula (1), wherein: Ar is selected from fluorenylene or indenofluorenylene; R1 and R2 are independently selected from H , C1-12 aliphatic alkyl group, C1-12 aliphatic cycloalkyl group, C6-30 aryl group, C6-30 heterocyclic aryl group, triarylamine group; Ar1 ​​and Ar2 are independently selected from C1-12 aliphatic alkyl group, C1-12 aliphatic cycloalkyl group or C6-30 aryl group; L1 and L2 are independently selected from single bond, C1-20 alkylene group, substituted or unsubstituted C6 -30 arylene and substituted or unsubstituted C6-30 heteroarylene; provided that R1 and R2 are not H at the same time. The compound has stable properties and simple preparation process, and when used as a phosphorescent host material in an electroluminescent device, the device exhibits high luminous efficiency and 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 layer in the device is formed by co-evaporation of two types of mate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1014H10K85/6572
Inventor 李银奎李艳蕊范洪涛
Owner BEIJING ETERNAL MATERIAL TECH