Fluorene derivative containing carbazole-9-yl group and application thereof

A technology of fluorene derivatives and groups, applied in the field of new organic compounds, can solve problems such as low glass transition temperature, no bright spots, and shortened device life, and achieve simple preparation process, improved service life, and good thermal stability. Effect

Active Publication Date: 2015-05-27
GUAN ETERNAL MATERIAL TECH
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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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  • Fluorene derivative containing carbazole-9-yl group and application thereof
  • Fluorene derivative containing carbazole-9-yl group and application thereof
  • Fluorene derivative containing carbazole-9-yl group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of compound 1

[0049] first step,

[0050]

[0051] In a 500ml three-neck flask equipped with electric stirring and protected by Ar gas, add 16.7g of carbazole (molecular weight 167, 0.10mol), 44g of 2-bromo-7-iodo-9,9-dimethylfluorene (molecular weight 398 , 0.11mol), cuprous iodide 1.9g (molecular weight 190, 0.01mol), potassium carbonate 28g (molecular weight 138, 0.203mol), 18-crown-6 1.2g (molecular weight 264, 0.00455mol), adding solvent DMPU 250ml. Stir at reflux for 4 hours and monitor the reaction by TLC. After the reaction is complete, naturally stir to lower the temperature to below 80°C, then add 500ml of water and stir, a light yellow solid product is precipitated, filtered out, and dried in the air. It was separated by silica gel column chromatography to obtain 35.7 g of a slightly yellow product with a molecular weight of 437, a purity of 98.0%, and a yield of 80.2%.

[0052] second step,

[0053]

[0054] In a 500 ml three-necked fl...

Embodiment 2

[0066] Synthesis of compound 2

[0067]

[0068] The synthesis process is divided into three steps. The first step is the same as the first step reaction in Example 1, except that the carbazole is replaced with 3-phenylcarbazole as a raw material, and other raw materials and processes are unchanged to obtain a corresponding Bromine intermediate; the second step is the same as the second step in Example 1, except that 2-bromo-7-(carbazol-9 base)-9,9-dimethylfluorene is synthesized by the first step here The bromine intermediate is replaced as a raw material, and other raw materials and processes are unchanged to obtain the corresponding boronic acid derivative; the third step is the same as the fifth step reaction in Example 1, except that the 7-(carbazol-9-yl) -9,9-Dimethylfluorene-2-boronic acid was replaced by the boronic acid derivative synthesized in the second step here as the raw material, and the other raw materials and processes remained unchanged to obtain compound...

Embodiment 3

[0071] Synthesis of compound 3

[0072]

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Abstract

The invention provides a novel fluorene derivative containing a carbazole-3-yl group, which is shown in the structure of formulae (1), (2) or (3). In the structure, one of A and B is N, and the other one is a CH group or a CH group of which H can be substituted; Ar is selected from fluorenylidene or indenofluoreneylidene; R1 and R2 are respectively and independently selected from H, substituted or unsubstituted fatty alkyl of C1-12, fatty naphthenic base of C1-12 or aryl of C6-30, methylthio, methoxyl, ethoxy or trifluoromethyl; R3 and R4 are respectively and independently selected from H, fatty alkyl of C1-12, fatty naphthenic base of C1-12 or aryl of C6-30; L1 and L2 are respectively and independently selected from single bond, alkylidene of C1-12, and substituted or unsubstituted arylidene of C6-30 or hetero-arylidene of C6-30. The compound is stable in property and simple in preparation process, can be used as a phosphorescence host material in organic electroluminescence devices 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D487/04C09K2211/1044H10K85/6572H10K50/11
Inventor 李银奎汤金明范洪涛
Owner GUAN ETERNAL MATERIAL TECH
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