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Method for purifying halogenated dibenzothiophene compound

A technology of dihalogenated dibenzothiophene and dibenzothiophene, which is applied in the field of purification of halogenated dibenzothiophene compounds, and can solve the problems of high residues of by-products and raw materials, low yield of target products, and reduced production efficiency, etc. problems, to achieve the effects of low product loss, low production cost, and improved production efficiency

Pending Publication Date: 2022-07-29
JIANGSU NATA OPTO ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the reaction process of synthesizing halogenated dibenzothiophenes, there are many by-products and raw materials remaining, and the yield of the target product is low. To obtain high-purity halogenated dibenzothiophenes, the conventional purification method is column Chromatography, but some halogenated dibenzothiophene compounds with specific structures need several times of column chromatography to obtain high-purity products, and this process will produce a large amount of solid waste and a large amount of solvent loss in the scale-up production , leading to an increase in production costs and a decrease in production efficiency

Method used

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  • Method for purifying halogenated dibenzothiophene compound
  • Method for purifying halogenated dibenzothiophene compound
  • Method for purifying halogenated dibenzothiophene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0035] A method for purifying halogenated dibenzothiophenes, comprising the following steps:

[0036] S1: Synthetic

[0037] 13.5g of 2,8-dibromodibenzothiophene, 400ml of ethylene glycol dimethyl ether, 27.2g of potassium carbonate, 105g of water, 2.8g of tetrakis(triphenylphosphine) palladium, 6.1g of 1- Naphthalene boric acid, replaced by N2 (nitrogen) for 5 times, the oil bath was heated to reflux, kept for 24 hours, the reaction solution was allowed to stand and cooled to room temperature, and suction filtered to obtain about 14 g of solid, the filtrate was rotary-evaporated at a temperature of 60 °C, and rotary-evaporated When there is a little liquid at the bottom of the pear-shaped bottle, suction filtration (accelerating solid-liquid separation) to obtain a yellow solid—the crude halogenated dibenzothiophene compound.

[0038] The crude halogenated dibenzothiophenes were analyzed by liquid chromatograph, and obtained as follows: figure 1 The high performance liquid ...

Embodiment 2

[0055] A method for purifying halogenated dibenzothiophenes, comprising the following steps:

[0056] S1: Synthetic

[0057] Add 12.4g 2,8-dibromodibenzothiophene, 350mL ethylene glycol dimethyl ether, 23.2g potassium carbonate, 95g water, 2.4g tetrakis(triphenylphosphine) palladium, 5.2g 4-tris into the 500mL reaction flask Aniline boric acid, replaced by N2 for 5 times, the oil bath was heated to reflux, kept for 20h, the reaction solution was allowed to stand and cooled to room temperature, and suction filtered to obtain about 15.6g of solid, the filtrate was rotary-evaporated at a temperature of 60 °C, and rotary-evaporated to pear There is a little liquid at the bottom of the shaped bottle, which is filtered with suction to obtain a yellow solid - a crude halogenated dibenzothiophene compound.

[0058] S2: Washing

[0059]Add the yellow solid into a 500ml single-necked bottle, add 400ml of petroleum ether and acetonitrile (petroleum ether:acetonitrile=1:10), heat up to ...

Embodiment 3

[0064] A method for purifying halogenated dibenzothiophenes, comprising the following steps:

[0065] S1: Synthetic

[0066] Into a 500mL reaction flask, add 15.3g 2-bromo-8-iodo-dibenzothiophene, 500mL ethylene glycol dimethyl ether, 23.2g potassium carbonate, 95g water, 2.4g tetrakis(triphenylphosphine) palladium, 4.6g4 - Biphenylboronic acid, replaced by N2 for 5 times, the oil bath was heated to reflux, kept for 20h, the reaction solution was allowed to stand and cooled to room temperature, suction filtered to obtain about 15.1g of solid, the filtrate was rotary-evaporated at a temperature of 60°C, and rotary-evaporated There is a little liquid at the bottom of the pear-shaped bottle, and suction filtration to obtain a yellow solid - a crude halogenated dibenzothiophene compound.

[0067] S2: Washing

[0068] The yellow solid was put into a 500ml single-neck bottle, 350ml of methanol was added, the temperature was raised to 60°C, stirred for 20min, suction filtered, and ...

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Abstract

The invention provides a method for purifying halogenated dibenzothiophene compounds, which comprises the following steps of: performing Suzuki reaction on dihalogenated dibenzothiophene and corresponding raw materials to obtain a halogenated dibenzothiophene compound crude product, adding a specific solvent into the halogenated dibenzothiophene compound crude product at a specific temperature, stirring and washing for multiple times, and filtering while the halogenated dibenzothiophene compound crude product is hot; adding a specific solvent, dissolving the crude product at reflux temperature, filtering while hot, cooling and crystallizing; and drying in vacuum to obtain a product with the content of 95% or above. The method is suitable for industrial production, less solid waste is generated, and the solvent can be recycled; the production time is shortened, the production efficiency is improved, and the production cost is low; in the purification process, the product loss is low, and the yield is improved.

Description

technical field [0001] The invention relates to a method for purifying halogenated dibenzothiophene compounds, and the purified product can be used as an OLED material intermediate. Background technique [0002] Halogenated dibenzothiophenes can be used as OLED (Organic Electroluminescence Display, organic electroluminescent semiconductor) intermediates to synthesize OLED materials with excellent performance. However, in the process of synthesizing halogenated dibenzothiophenes, there are many residual by-products and raw materials, and the yield of the target product is low. To obtain high-purity halogenated dibenzothiophenes, the conventional purification method is column Chromatography, but some halogenated dibenzothiophenes with specific structures require several column chromatography to obtain high-purity products, and this process will generate a large amount of solid waste and a large amount of solvent loss during scale-up production. , resulting in increased produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76
CPCC07D333/76
Inventor 丁宗苍陶鑫郭超成春文李帅朱宇
Owner JIANGSU NATA OPTO ELECTRONICS MATERIAL