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2, 7-dibromo-n-perfluorooctylethyl carbazole and preparation method thereof

A technology of perfluorooctylethylcarbazole and dibromocarbazole is applied in the field of 2,7-dibromo-N-perfluorooctylethylcarbazole and its preparation, and can solve poor stability and difficult post-processing and other problems, to achieve the effect of good stability, simple post-processing method and simple preparation method

Inactive Publication Date: 2015-01-07
SUZHOU SHENGPULA NEW MATERIAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are patent reports on 2,7-dibromo-N-perfluorobutylethyl carbazole and its preparation method, but 2,7-dibromo-N-perfluorobutyl ethyl carbazole has poor stability and is later difficult to deal with

Method used

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  • 2, 7-dibromo-n-perfluorooctylethyl carbazole and preparation method thereof
  • 2, 7-dibromo-n-perfluorooctylethyl carbazole and preparation method thereof
  • 2, 7-dibromo-n-perfluorooctylethyl carbazole and preparation method thereof

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Experimental program
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Embodiment 1

[0020] Step (1): Add 4,4'-dibromobiphenyl, dichloromethane and nitric acid mixed acid with a molar ratio of 1:25:1 in sequence in the reaction flask, stir, and react at a constant temperature of 25°C for 1 to 4 hours , cooled to room temperature to obtain the reaction solution, washed with NaOH aqueous solution until neutral, extracted with dichloromethane, and the organic phase was washed with anhydrous NaSO 4 Drying, concentration, and ethanol recrystallization to obtain 2-nitro-4,4'-dibromobiphenyl, the mixed nitric acid is a mixture of fuming nitric acid and concentrated sulfuric acid, and its volume ratio is 1:1;

[0021] Step (2): Add 2-nitro-4,4'-dibromobiphenyl, triphenylphosphine, and o-dichlorobenzene obtained in step (2) into the reaction flask at a molar ratio of 1:3:15 in, stirred, and refluxed for 5 hours, cooled to room temperature, then petroleum ether was added thereto, filtered, and dried to obtain 2,7-dibromocarbazole, wherein the amount of petroleum ether a...

Embodiment 2

[0025] Step (1): Add 4,4'-dibromobiphenyl, dichloromethane and nitric acid mixed acid with a molar ratio of 1:78:5 in sequence in the reaction flask, stir, react at a constant temperature of 40°C for 4 hours, and cool to room temperature, the reaction solution was obtained, washed with NaOH aqueous solution until neutral, extracted with dichloromethane, and the organic phase was washed with anhydrous NaSO 4 Dry, concentrate, and recrystallize from ethanol to obtain 2-nitro-4,4'-dibromobiphenyl. The mixed nitric acid is a mixture of fuming nitric acid and concentrated sulfuric acid, and its volume ratio is 1:8;

[0026] Step (2): Add 2-nitro-4,4'-dibromobiphenyl, triphenylphosphine and o-dichlorobenzene obtained in step (2) into the reaction flask at a molar ratio of 1:5:25 , stirred, refluxed for 9 hours, cooled to room temperature, then added petroleum ether, filtered, and dried to obtain 2,7-dibromocarbazole, wherein the amount of petroleum ether added was 1.5 times the volu...

Embodiment 3

[0029] Step (1): Add 4,4'-dibromobiphenyl, dichloromethane and nitric acid mixed acid with a molar ratio of 1:52:3 in sequence in the reaction flask, stir, react at a constant temperature of 35°C for 3 hours, and cool to room temperature to obtain the reaction solution, washed with KOH aqueous solution to neutrality, extracted with dichloromethane, and the organic phase was washed with anhydrous NaSO 4 Dry, concentrate, and recrystallize from ethanol to obtain 2-nitro-4,4'-dibromobiphenyl. The mixed nitric acid is a mixture of fuming nitric acid and concentrated sulfuric acid, and its volume ratio is 1:5;

[0030] Step (2): Add 2-nitro-4,4'-dibromobiphenyl, triphenylphosphine, and o-dichlorobenzene obtained in step (2) into the reaction flask at a molar ratio of 1:4:21 , stirred, refluxed for 7 hours, cooled to room temperature, then added petroleum ether therein, filtered, and dried to obtain 2,7-dibromocarbazole, wherein the amount of petroleum ether added was twice the volu...

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Abstract

The invention belongs to the technical field of organic synthesis and specifically relates to 2, 7-dibromo-N-perfluorooctylethyl carbazole. 2, 7-dibromo-N-perfluorooctylethyl carbazole is obtained by taking 4, 4'-dibromobiphenyl as a raw material, firstly performing nitration reaction with a mixed acid of nitric acid and sulfuric acid, then performing cyclization with triphenylphosphine to obtain 2, 7-dibromocarbazole and further performing alkylation. The post-treatment method provided by the invention is simple and relatively good in stability; simultaneously, 2, 7-dibromo-N-perfluorooctylethyl carbazole prepared by the method provided by the invention has better water resistance by utilizing the hydrophobicity of fluorine atoms, and has good application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 2,7-dibromo-N-perfluorooctylethylcarbazole and a preparation method thereof. Background technique [0002] Most of the small molecule OLED device materials synthesized by carbazole compounds are made of 3,6,9-modified carbazole small molecules, because the hydrogen on the 3,6-position of carbazole is easily activated , an electrophilic substitution reaction occurs, and the 2,7-substituted carbazole compounds are relatively difficult to synthesize. However, recent experimental studies have found that the 2,7-position substituted carbazole-based small-molecule OLED materials have many superior properties due to their larger conjugated systems, such as high thermal stability, excellent photoelectric Conductivity, etc., is a very promising blue electroluminescent material. [0003] Due to people's higher and higher requirements on material performance, material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 费金华
Owner SUZHOU SHENGPULA NEW MATERIAL SCI & TECH
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