A kind of bipyrene and its preparation method and use

A technology of bipyrene and hydroxypyrene, which is applied in the field of synthesis of photoresist materials, can solve the problems of harsh reaction conditions, low reaction yield, and restrictions on the wide application of bipyrene phenolic compounds, and achieves mild reaction conditions and excellent preparation methods. simple effect

Active Publication Date: 2016-08-17
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Similar compounds are generally prepared from brominated aromatic rings and hydroxyaromatic ring boronic acids, but these synthetic methods are difficult to prepare raw materials, harsh reaction conditions, low reaction yields and many other shortcomings, which limit the wide application of bipyrene phenolic compounds. application

Method used

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  • A kind of bipyrene and its preparation method and use
  • A kind of bipyrene and its preparation method and use
  • A kind of bipyrene and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1 bipyrenol

[0030] In a 250mL three-necked flask, add 4.36g 1-hydroxypyrene (20mmol), 11.24g 1-bromopyrene (40mmol) and 4.48g potassium tert-butoxide (40mmol), then add 50mL o-xylene, mechanically stir, and add to the reaction The nitrogen gas was continuously passed through the vessel for 10 minutes to obtain a mixed solution. Raise the temperature to 40-60°C, blow nitrogen and stir for 10 minutes to remove the oxygen in the reaction flask, add 4.5mgPd(OAc) 2 (0.02mmol) and 14.3mg of bis(1-adamantyl)butylphosphine (0.04mmol), continue to heat up to 80-100°C, and react for 2-6h. TLC followed the reaction until no 1-hydroxypyrene remained. Add 50mL of tetrahydrofuran to the reaction solution, filter, and concentrate the filtrate under reduced pressure to remove the organic solvent to obtain 9.7g of brown solid, add 48.5g of toluene and absolute ethanol mixture (the mass ratio of toluene and absolute ethanol is 2:1), Heat to dissolve, co...

Embodiment 2

[0032] The preparation of embodiment 2 bipyrenol

[0033] In a 250mL three-necked flask, add 4.36g 1-hydroxypyrene (20mmol), 11.24g 1-bromopyrene (40mmol) and 3.84g sodium tert-butoxide (40mmol), then add 50mL o-xylene, mechanically stir, and add to the reaction Continue to pass nitrogen in the container for 10 minutes to obtain a mixed solution, raise the temperature to 40-60°C, pass nitrogen and stir for 10 minutes to remove oxygen in the reaction flask, add 4.5mgPd(OAc) 2 (0.02mmol) and 14.3mg of bis(1-adamantyl)butylphosphine (0.04mmol), continue to heat up to 80-100°C, and react for 2-6h. TLC followed the reaction until no 1-hydroxypyrene remained. Add 50mL of tetrahydrofuran to the reaction solution, filter, and concentrate the filtrate under reduced pressure to remove the organic solvent to obtain 9.3g of brown solid, add 46.5g of toluene and absolute ethanol mixture (the mass ratio of toluene and absolute ethanol is 2:1), Heat to dissolve, cool down naturally, a ligh...

Embodiment 3

[0035] The preparation of embodiment 3 bipyrenol

[0036] In a 250mL three-necked flask, add 4.36g 1-hydroxypyrene (20mmol), 11.24g 1-bromopyrene (40mmol) and 4.48g potassium tert-butoxide (40mmol), then add 50mL o-xylene, mechanically stir, and add to the reaction Continue to pass nitrogen in the container for 10 minutes to obtain a mixed solution, raise the temperature to 40-60°C, pass nitrogen and stir for 10 minutes to remove oxygen in the reaction flask, add 4.5mgPd(OAc) 2 (0.02mmol) and 8.1mg tri-tert-butylphosphine (0.04mmol), continue to heat up to 80-100°C, and react for 2-6h. TLC followed the reaction until no 1-hydroxypyrene remained. Add 50mL of tetrahydrofuran to the reaction solution, filter, and concentrate the filtrate under reduced pressure to remove the organic solvent to obtain 8.9g of brown solid, add 44.5g of toluene and absolute ethanol mixture (the mass ratio of toluene and absolute ethanol is 2:1), Heat to dissolve, cool down naturally, a light yellow...

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Abstract

The invention relates to dipyrenol, a preparation method and an application thereof. The preparation method includes the steps of performing a coupling reaction with 1-bromopyrene and 1-hydroxypyrene as raw materials under catalysis of palladium, and treating the product after the reaction is finished to obtain the dipyrenol. The dipyrenol is a new compound which is not reported before and has excellent application value in the field of photoresists. Compared with conventional methods for preparing the compound, the preparation method relates to carbon-hydrogen bond activation and coupling of an aromatic compound. A palladium catalyst is easy to obtain. The reaction method is simple and the reaction conditions are easy to reach. The preparation method is high in application value and commercial value.

Description

technical field [0001] The invention relates to a bipyrene phenol and its preparation method and application, belonging to the field of synthesis of photoresist materials. Background technique [0002] In recent years, China's microelectronics and flat panel display industries have developed rapidly, driving the establishment and development of related supporting enterprises in the industrial chain such as photoresist materials. In particular, the rapid development of LED (light emitting diode) in 2009 has more effectively promoted the development of the photoresist industry. On the basis of the original discrete devices, IC, and LCD (liquid crystal display), China's photoresist industry market has added LEDs, coupled with the potential market for photovoltaics. By 2010, China's photoresist market will exceed 2 billion yuan. Accounting for more than 10% of the international photoresist market. [0003] During the imaging process of the photoresist, due to certain diffracti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/12C07C37/18C09D5/00
CPCC07C37/18C07C39/12C09D5/006
Inventor 李强马振堂易朝辉李王敏焦瑶候美玲
Owner VALIANT CO LTD
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