Method for preparing tricarbazole materials from aryl oxindole in one step

A technology of trioxacarbazoles and arylindolinones, which is applied in the direction of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of long synthesis steps, single substituent mode and position, and restrictions on trioxacarbazoles Compound application and other issues

Inactive Publication Date: 2013-12-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In summary, the above-mentioned methods for introducing aryl branched chains all have the disadvantages of relatively long synthesis steps, and relatively single ways and positions of substituents, which greatly limit the application of tricarbazoles in organic electroluminescent materials. application

Method used

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  • Method for preparing tricarbazole materials from aryl oxindole in one step
  • Method for preparing tricarbazole materials from aryl oxindole in one step
  • Method for preparing tricarbazole materials from aryl oxindole in one step

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Example 1: Synthesis of 5,10,15-triethyl-3,8,13-triphenyltricarbazole (1a)

[0028] N-Ethyl-5-phenylindolinone (2.37g, 10.0mmol) was dissolved in 10ml of toluene, added to 10ml of phosphorus oxychloride solution, magnetically stirred, temperature controlled at 100-110°C, and reacted for 16h. Then cool to room temperature, pour into ice water, stir well, and use Na 2 CO 3 Neutralized to neutral, then extracted 3 times with dichloromethane, combined organic layers, dried, evaporated to remove solvent, and obtained white solid powder 5,10,15-triethyl-3,8,13-tri Phenyltricarbazole (1a) 0.85g, yield 39%, melting point 254.3°C, see attached figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

Embodiment 2

[0029] Example 2: Synthesis of 5,10,15-triethyl-3,8,13-tri-tert-butylphenyltricarbazole (1b)

[0030] N-ethyl-5-tert-butylphenylindolinone (2.93g, 10.0mmol) was dissolved in 10ml of toluene, added to 10ml of phosphorus oxychloride solution, magnetically stirred, temperature controlled at 100-110°C, and reacted for 20h. Then cool to room temperature, pour into ice water, stir well, and use Na 2 CO 3 Neutralized to neutral, then extracted 3 times with dichloromethane, combined organic layers, dried, evaporated to remove solvent, and obtained white solid powder 5,10,15-triethyl-3,8,13-tri tert-butylphenyltricarbazole (1b) 1.11g, yield 40.5%, melting point 254.8°C, see attached figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

Embodiment 3

[0031] Example 3: Synthesis of 5,10,15-triethyl-3,8,13-trimethoxyphenyltricarbazole (1c)

[0032] N-ethyl-5-methoxyphenylindolinone (2.67g, 10.0mmol) was dissolved in 10ml of toluene, added to 10ml of phosphorus oxychloride solution, magnetically stirred, temperature controlled at 100-110°C, and reacted for 10h. Then cool to room temperature, pour into ice water, stir well, and use Na 2 CO 3 Neutralized to neutral, then extracted 3 times with dichloromethane, combined organic layers, dried, evaporated to remove solvent, and obtained light yellow solid powder 5,10,15-triethyl-3,8,13- Trimethoxyphenyl tricarbazole (1c) 0.84g, yield 33.7%, melting point 367.8°C, see attached for ultraviolet absorption spectrum figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

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Abstract

The invention provides a method for preparing tricarbazole materials from aryl oxindole in one step. The method utilizes aryl oxindole as a raw material, and directly obtains tricarbazole compounds through one-step synthesis under the condition that phosphorus oxychloride is used as a dehydrating agent. The method solves the problems that methods for synthesizing tricarbazole compounds in the prior art have long steps, and there is only one single way for introducing substituents into tricarbazole compounds. The obtained compound can be hopefully used for organic light emitting diodes.

Description

technical field [0001] The present invention relates to a kind of preparation method of trioxacarbazole material, be specifically related to a kind of using arylindolinone as raw material, directly in POCl 3 It is a method for obtaining tricarbazole materials through condensation under the condition of dehydrating agent. technical background [0002] Tricarbazole can be regarded as a molecule with three-fold symmetry formed by three carbazole units sharing a central benzene ring. Obviously, because the lone pair of electrons on the nitrogen atom participates in the π system, the trioxacarbazole has great conjugation. Therefore, in the construction of organic optoelectronic molecules, tricarbazole can not only serve as an excellent π-conjugated bridge, but also as a central donor due to its electron-rich properties, making it possible to become an excellent light-emitting material, and has the potential to become a The potential of excellent hole transport materials has bro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14C09K11/06
Inventor 朱红军朱天昊姜鹏王昆彦朱晓林陈琛
Owner NANJING UNIV OF TECH
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