Preparation method of key intermediate of triphenylene bisborate

Abstract

The invention discloses a preparation method of a key intermediate, represented as the formula V, of triphenylene bisborate. The method includes the following steps: a) with 1,2-dibromobenzene and 3-methoxyphenylboronic acid as raw materials, performing a coupling reaction to obtain a compound (1) which is represented as the formula (I); b) adding molybdenum pentachloride to the compound (1) to perform oxidizing coupling to obtain a compound (2) which is represented as the formula (II); c) adding an acid to the compound (2) to perform a demethylating reaction to obtain a compound (3) which isrepresented as the formula (III); d) performing a reaction to the compound (3) with trifluoromethanesulfonic anhydride to prepare a compound (4) which is represented as the formula (IV); e) performinga boronizing reaction to the compound (4) with catalysis by Pd (II) to prepare the key intermediate (5), which is represented as the formula (V), of the triphenylene bisborate. In the invention, theinitial raw material, 1,2-dibromobenzene and 3-methoxyphenylboronic acid, are low in cost and easy to obtain; the total yield of the product, key intermediate (5) of the triphenylene bisborate, can reach 48.6%; the reaction process is free of liquid bromine, which is liable to cause environment pollution.

Description

technical field [0001] The invention relates to the preparation of a key intermediate of triphenylene bis-boronate, an important electron transport material in the field of OLEDs. Background technique [0002] OLED is an autonomous light-emitting device without a backlight. It has the characteristics of fast response, low driving voltage, high luminous efficiency and resolution, high contrast, and wide viewing angle. In addition, it can use cheap glass, metal or even flexible plastic as a substrate. Therefore, it also has the advantages of low cost, simple production process, and large-area production, and has become a new generation of full-color display and lighting technology. Since Deng Qingyun and VanSlyke of Kodak Company prepared the first organic light-emitting diode (OLED) in 1987 (Appl. Phys. Lett. 1987, 51, 913), due to its huge potential application in the field of full-color display and solid-state lighting, Whether in academia or industry, OLEDs are attracting...

AI Technical Summary

Problems solved by technology

[0017] The present invention is aimed at the expensive starting raw materials that exist in the triphenylene bis-boronate key intermediate 5 shown in the formula V existing in the existing synthesis technology, the need to use liquid bromine, and the key step MoCl 5 The low yield of the promoted oxidative coupling and the low overall yield of the key intermediate 5 shown in the formula V provide an efficient preparation method for the key intermediate 5 of the triphenylene bis-boronate shown in the formula V , its preparation cost is low, the yield is high, the process is stable, the quality is good, the operation is simple, and it is suitable for the preparation of gram level and more

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