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A kind of synthetic method of 3-bromo-9-(9-phenylfluoren-9-yl)carbazole

A synthetic method, benzoyl carbazole technology, applied in the field of organic synthesis, can solve problems such as high hole mobility, achieve high luminous efficiency, vitrification problem improvement, and high thermal stability

Active Publication Date: 2019-02-01
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] Carbazole-centered fluorene compounds have high hole mobility, and there is no relevant literature report on the preparation method of 3-bromo-9-(9-phenylfluoren-9-yl)carbazole compounds

Method used

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  • A kind of synthetic method of 3-bromo-9-(9-phenylfluoren-9-yl)carbazole

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Effect test

Embodiment 1

[0016] Under the protection of argon, 5.83 g (25 mmol) of 2-bromobiphenyl and 50 mL of methyl tert-butyl ether were successively added to a 250 mL three-necked flask, and the temperature was lowered to -30°C, and n-butyllithium in n-hexane was added dropwise Solution (2.5 mol / L) 12 mL (30 mmol), keep stirring at -30 ℃ for 0.5 h after the dropwise addition, add dropwise 8.76 g (25 mmol) of 3-bromo-9-benzoylcarbazole and 20 mLTHF to prepare After the reaction is over, add 30 mL of dilute hydrochloric acid aqueous solution to the reaction solution for hydrolysis, separate the organic phase, dry over anhydrous magnesium sulfate, concentrate the solvent under reduced pressure, add 50 mL of toluene, and then add 0.523 g of ferric sulfate monohydrate, Raise the temperature to 40°C and stir for 72 h. After the reaction, add 30 mL of water to the reaction liquid, separate the organic phase, extract the water layer with 30 mL of toluene, dry over anhydrous magnesium sulfate, and recover ...

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Abstract

The invention discloses a synthesis method for 3-bromine-9-(9-benzofiurene-9-base) carbazole, and belongs to organic synthesis. The synthesis method includes the steps: taking 2-bromine biphenyl and 3-bromine-9-phenacyl carbazole as raw materials; performing lithiation by the aid of n-butyllithium; hydrolyzing; synthesizing the 3-bromine-9-(9-benzofiurene-9-base) carbazole by the aid of monohydrate ferric sulfate catalytic ring closing reaction. The synthesis method is simple and practicable and suited to industrial production, and total yield reaches 85% or more. The carbazole has good heat stability and glass temperature and is suited to serving as intermediates for synthesizing organic light-emitting materials.

Description

technical field [0001] The invention relates to a synthesis method of a class of 3-bromocarbazole derivatives, in particular to a synthesis method of 3-bromo-9-(9-phenylfluoren-9-yl)carbazole, which belongs to the field of organic synthesis. Background technique [0002] Carbazole and its derivatives are a class of heterocyclic aromatic compounds with large π-electron conjugated system and strong intramolecular electron transfer characteristics. From the structural point of view, the electrophilic N atom of carbazole absorbs double atoms through the inductive effect. The electrons on the bond; on the other hand, due to the p-π conjugation effect, the unshared electrons of the N atom are supplied to the double bond, making the double bond rich in electrons. Therefore, the carbazole ring has a strong hole transport ability, and the carbazole polymer or small molecule compound can be used as a hole transport layer in organic electroluminescent devices, which reduces the crystal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88C09K11/06
CPCC07D209/88C09K11/06C09K2211/1029
Inventor 李奎杨振强杨瑞娜屈凤波陈辉席振峰侯益民王从洋
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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