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A kind of 5-hydrogen-benzo[b]carbazole and related derivatives and synthesis method thereof

A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult preparation of β-nitro-substituted compounds, inability to supply in large quantities, difficult separation and purification, etc., so as to avoid the influence of reaction purification difficulties, easy purification, and simple operation Effect

Active Publication Date: 2022-03-29
西安欧得光电材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the above-mentioned deficiencies in the prior art, provide a kind of 5-hydrogen-benzo [b] carbazole and related derivatives and synthetic method thereof, overcome 1 in the prior art: required for nitro ring closure It is difficult to prepare the β-nitro-substituted compound of the raw material, which cannot be supplied in large quantities, and the yield is lower than 50%, and the price is expensive; 2: The conversion rate of the product required to generate an isomeric mixture during the synthesis process is lower than 15%; 3: Difficult Realize separation and purification, purification difficulties and other problems

Method used

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  • A kind of 5-hydrogen-benzo[b]carbazole and related derivatives and synthesis method thereof
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  • A kind of 5-hydrogen-benzo[b]carbazole and related derivatives and synthesis method thereof

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specific Embodiment approach

[0019] It should be noted that the structures, proportions, sizes, etc. shown in this specification are only used to cooperate with the contents disclosed in the specification, so as to be understood and read by those who are familiar with this technology, and are not used to limit the conditions that the present invention can be implemented. , any modification of the structure, the change of the proportional relationship or the adjustment of the size, without affecting the effect that the present invention can produce and the purpose that can be achieved, should still fall within the scope that the technical content disclosed in the present invention can cover .

[0020] At the same time, the terms such as "up", "down", "left", "right", "middle" and "one" quoted in this specification are only for the convenience of description and clarity, and are not used to limit this specification. The implementable scope of the invention, and the change or adjustment of the relative relat...

Embodiment 1

[0022] The invention discloses a method for synthesizing 5-hydro-benzo[b]carbazole and related derivatives, comprising the following steps:

[0023] Step 1) utilize sodium hydride to carry out alpha carbon activation on 2-tetralone, wherein the molar ratio of sodium hydride and 2-tetralone is 0.8~1.2:1, and drop bromine into the reaction solution after alpha carbon activation to generate The substitution reaction generates 1-bromo-2 tetralone, wherein the molar ratio of 2-tetralone to bromine is 1:1 to 1:1.5;

[0024] Step 2) Using the 1-bromo-2 tetralone generated in step 1) and phenylhydrazine salt to undergo Fisher indole ring-closure reaction to generate 6-bromo-6,11-dihydro-5-hydrobenzene[b]and Carbazole and related derivatives, wherein the molar ratio of 1-bromo-2 tetralone and phenylhydrazine salt is 1:1 to 1:1.3;

[0025] Step 3) The 6-bromo-6,11-dihydro-5-hydrobenzene[b]carbazole and related derivatives generated in step 2) are subjected to an aromatization reaction ...

Embodiment 2

[0027] The invention discloses a method for synthesizing 5-hydro-benzo[b]carbazole and related derivatives, comprising the following steps:

[0028] Step 1) utilize sodium hydride to carry out alpha carbon activation on 2-tetralone, wherein the molar ratio of sodium hydride and 2-tetralone is 0.8~1.2:1, and drop bromine into the reaction solution after alpha carbon activation to generate The substitution reaction generates 1-bromo-2 tetralone, wherein the molar ratio of 2-tetralone to bromine is 1:1 to 1:1.5;

[0029] Step 2) Using the 1-bromo-2 tetralone generated in step 1) and phenylhydrazine salt to undergo Fisher indole ring-closure reaction to generate 6-bromo-6,11-dihydro-5-hydrobenzene[b]and Carbazole and related derivatives, wherein the molar ratio of 1-bromo-2 tetralone and phenylhydrazine salt is 1:1 to 1:1.3;

[0030] Step 3) The 6-bromo-6,11-dihydro-5-hydrobenzene[b]carbazole and related derivatives generated in step 2) are subjected to an aromatization reaction ...

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Abstract

The invention discloses a 5-hydro-benzo[b]carbazole and related derivatives and a synthesis method thereof. Step 1) 2-tetralone is activated by alpha carbon by using sodium hydride, wherein sodium hydride and 2-naphthalene The molar ratio of fullone is 0.8~1.2:1, and bromine is dripped into the reaction solution to generate substitution reaction to generate 1-bromo-2 tetralone, wherein the molar ratio of 2-tetralone to bromine is 1:1~ 1:1.5; Step 2) Use the 1-bromo-2 tetralone generated in step 1) to undergo Fisher indole ring closure reaction with phenylhydrazine salt to generate 6-bromo-6,11-dihydro-5-hydrobenzene [b] carbazole and related derivatives, wherein the molar ratio of 1-bromo-2 tetralone to phenylhydrazine salt is 1:1~1:1.3; 6-bromo-formed in step 2) in step 3) 6,11-Dihydro-5-hydrobenzo[b]carbazole and related derivatives are aromatized to 5-hydro-benzo[b]carbazole and related derivatives.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a 5-hydro-benzo[b]carbazole and related derivatives and a synthesis method thereof. Background technique [0002] At present, carbazole-containing aromatic ring compounds have been widely developed and applied in the field of OLED new display materials. It is very large, and the properties of its derivatives vary widely. In order to maintain the performance stability of the device more efficiently and lastingly, the synthesis, performance testing and screening of related carbazole derivatives are becoming more and more important and urgent. 5-Hydro-benzo[b]carbazole and related derivatives OLEDs have been designed for a long time, but limited by the existing synthesis methods, the influence of synthesis difficulty and purity has not been successfully solved, so that similar materials cannot be researched and used on a large scale, and related OLED materials are availab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80
Inventor 任莺歌郭随林杨松彬任沛褀
Owner 西安欧得光电材料有限公司
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