Preparation method of 2-amino-9, 9-diphenylfluorene

A technology of diphenylfluorene and amino, which is applied in the field of liquid crystal compound synthesis, can solve the problems of unfavorable mass production and high production cost, and achieve the effects of reduced production cost, high product yield and simple process flow

Active Publication Date: 2021-11-02
河北凡克新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses a noble metal catalyst. Although it can be reused, the production cost is expensive, and it needs to be separated when it is used again, which is not conducive to mass production.

Method used

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Examples

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Effect test

preparation example Construction

[0033] The invention provides a preparation method of 2-amino-9,9-diphenylfluorene, which comprises the following steps.

[0034] A) using 9-fluorenone as a raw material, through a bromination reaction, to obtain 2-bromo-9-fluorenone, the structural formula is,

[0035] The specific preparation method of 2-bromo-9-fluorenone is as follows.

[0036] A1) Add 9-fluorenone, acetic acid, water, and concentrated sulfuric acid in sequence in a three-necked flask, and mix well to obtain a reaction solution a1. The structural formula of 9-fluorenone is:

[0037] A2) The temperature of the reaction solution a1 is raised to 50-60 degrees Celsius, after slowly adding liquid bromine dropwise, it is incubated for 5-8 hours, and cooled to room temperature to obtain the reaction solution a2; wherein, the molar ratio of 9-fluorenone to liquid bromine is 1: 1~1.5.

[0038] A3) Suction filtration of the reaction solution a2 to obtain a filter cake. After washing the filter cake, vacuum-dry...

Embodiment 1

[0055] This embodiment is used to prepare the preparation method of 2-amino-9,9-diphenylfluorene, which specifically includes the following steps.

[0056] A) with 9-fluorenone As a raw material, 2-bromo-9-fluorenone is obtained by bromination reaction,

[0057] A1) There is a three-necked flask equipped with a stirring, thermometer, and constant pressure dropping funnel. Add 9-fluorenone (5.4g, 30mmol), 33mL of acetic acid, 11mL of water, and 0.8g of concentrated sulfuric acid into the three-necked flask, mix them, and stir evenly to obtain the reaction solution a1 .

[0058] A2) Reaction solution a1 was warmed up to 51 degrees centigrade, and liquid bromine (4.8 g, 39 mmol) was slowly added dropwise. After addition, the temperature was raised to 58 degrees centigrade, kept for 6 hours, and cooled to room temperature to obtain reaction solution a2.

[0059] A3) The reaction solution a2 is suction filtered, and the filter cake is washed 3 times with acetic acid-water solu...

Embodiment 2

[0075] This embodiment is used to prepare the preparation method of 2-amino-9,9-diphenylfluorene, which specifically includes the following steps.

[0076] A) using 9-fluorenone as a raw material, through a bromination reaction to obtain 2-bromo-9-fluorenone,

[0077] A1) There is a three-necked flask equipped with a stirring, thermometer, and constant pressure dropping funnel, to which 9-fluorenone (6.8g, 38mmol), 35mL of acetic acid, 15mL of water, and 0.96g of concentrated sulfuric acid are added and mixed, and stirred evenly to obtain the reaction solution a1 .

[0078] A2) Reaction solution a1 was warmed up to 51 degrees Celsius, and liquid bromine (5.6 g, 40 mmol) was slowly added dropwise. After the addition, the temperature was raised to 58 degrees Celsius, kept for 8 hours, and cooled to room temperature to obtain reaction solution a2.

[0079] A3) The reaction solution a2 is suction filtered, and the filter cake is washed 3 times with acetic acid-water solution wi...

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PUM

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Abstract

The invention discloses a preparation method of 2-amino-9, 9-diphenylfluorene, which comprises the following steps: taking 9-fluorenone as a raw material, and carrying out bromination reaction to obtain 2-bromo-9-fluorenone; reacting 2-bromine-9-fluorenone with a Grignard reagent of bromobenzene to obtain 2-bromine-9-phenyl-9-hydroxyl-fluorene; carrying out a Friedel-Crafts alkylation reaction on 2-bromine-9-phenyl-9-hydroxyl-fluorene and benzene to obtain 2-bromine-9, 9-diphenyl fluorene; and reacting 2-bromo-9, 9-diphenylfluorene with cuprous oxide, palladium acetate (II) and N-methyl pyrrolidone in liquid ammonia to obtain 2-amino-9, 9-diphenylfluorene. The method is used for preparing the 2-amino-9, 9-diphenylfluorene, the used preparation is easy to obtain, the technological process is simple, the product yield is high, the production cost is reduced, and mass production of the 2-amino-9, 9-diphenylfluorene can be achieved.

Description

technical field [0001] The invention relates to the technical field of liquid crystal compound synthesis, in particular to a preparation method of 2-amino-9,9-diphenylfluorene. Background technique [0002] Organic electroluminescent materials are expected to become a new generation of flat panel display technology due to their wide range of material selection, low energy consumption, high efficiency and luminous brightness, ultra-thin, full curing, fast response, active light emission, and large-area flexible display. Therefore, it has become one of the research hotspots in the fields of organic electronics and optoelectronic information. In organic electroluminescent diodes, in order to realize large-area full-color display, there must be stable red, green and blue primary colors, but at present only red and green have the luminous efficiency and lifespan necessary for commercial development, and realize the blue light emission of materials. High stability and high effici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/697C07C29/40C07C35/52C07C17/263C07C25/22C07C209/10C07C211/61
CPCC07C45/63C07C29/40C07C17/2632C07C209/10C07C2603/18C07C49/697C07C35/52C07C25/22C07C211/61Y02E10/549
Inventor 周维江田秋峰董茹陆敬国段军
Owner 河北凡克新材料有限公司
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