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2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide monomer

A technology of aminophenoxy and benzamide, which is applied in the field of fluorescent active 2--6--N-benzamide monomer and its preparation, can solve the problems of few public reports of polymer monomers, and achieve high fluorescence emission efficiency effect

Active Publication Date: 2019-11-12
ANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, in terms of macromolecular electroluminescent materials, there are few public reports on asymmetric organic fluorene-based polymer monomers with an "electron-donating group-electron-withdrawing group / conjugated" system.

Method used

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  • 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide monomer
  • 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide monomer
  • 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of 2,6-difluoro-N-[2-(fluorenylamino)]benzamide:

[0041] Under a nitrogen atmosphere and an ice-water bath, 9.06 g (50 mmol) of 2-aminofluorene, 150 mL of dichloromethane and 10.6 mL (75 mmol) of triethylamine were sequentially added to a thick-walled eggplant-shaped bottle (250 mL) equipped with a magnet, After the mixture was stirred well and mixed uniformly, 6.9 mL (65 mmol) of 2,6-difluorobenzoyl chloride was slowly added dropwise to the reaction mixture. The mixture continued to stir under this condition for 8 hours. After the 2-aminofluorene had completely reacted, the reaction was quenched with 100 mL of saturated ammonium chloride aqueous solution. At this time, a large amount of white solid was precipitated in the mixed system, which was suction filtered after standing for half an hour, and the filter cake was After washing with water and petroleum ether, 2,6-difluoro-N-[2-(fluorenylamino)]benzamide 2 was obtained with a yield of 90%.

[0042] Synth...

Embodiment 2

[0047] Synthesis of 2,6-difluoro-N-[2-(fluorenylamino)]benzamide:

[0048] Under a nitrogen atmosphere and an ice-water bath, 9.06 g (50 mmol) of 2-aminofluorene, 150 mL of dichloromethane and 10.6 mL (75 mmol) of triethylamine were sequentially added to a thick-walled eggplant-shaped bottle (250 mL) equipped with a magnet, After the mixture was stirred well and mixed uniformly, 6.9 mL (65 mmol) of 2,6-difluorobenzoyl chloride was slowly added dropwise to the reaction mixture. The mixture continued to stir under this condition for 8 hours. After the 2-aminofluorene had completely reacted, the reaction was quenched with 100 mL of saturated ammonium chloride aqueous solution. At this time, a large amount of white solid was precipitated in the mixed system, which was suction filtered after standing for half an hour, and the filter cake was After washing with water and petroleum ether, 2,6-difluoro-N-[2-(fluorenylamino)]benzamide 2 was obtained with a yield of 90%.

[0049] Synth...

Embodiment 3

[0054] Synthesis of 2,6-difluoro-N-[2-(fluorenylamino)]benzamide:

[0055] Under a nitrogen atmosphere and an ice-water bath, 9.06 g (50 mmol) of 2-aminofluorene, 150 mL of dichloromethane and 10.6 mL (75 mmol) of triethylamine were sequentially added to a thick-walled eggplant-shaped bottle (250 mL) equipped with a magnet, After the mixture was stirred well and mixed uniformly, 6.9 mL (65 mmol) of 2,6-difluorobenzoyl chloride was slowly added dropwise to the reaction mixture. The mixture continued to stir for 8 hours under this condition. After the 2-aminofluorene was completely reacted, the reaction was quenched with 100 mL of saturated ammonium chloride aqueous solution. At this time, a large amount of white solid was precipitated in the mixed system, which was suction filtered after standing for half an hour, and the filter cake was After washing with water and petroleum ether, 2,6-difluoro-N-[2-(fluorenylamino)]benzamide 2 was obtained with a yield of 90%.

[0056] Synth...

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Abstract

The invention discloses a 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide macromolecule monomer with fluorescence activity, and a preparation method thereof, and belongs to the field of functional macromolecule materials. The 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide macromolecule monomer is prepared from p-aminophenol / m-aminophenol and 2-fluorenyl-2,6-difluorobenzamide in a two-step reaction. The 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene)benzamide macromolecule monomer contains a phenylamine fragment capable of being polymerized and afluorenyl fragment with the fluorescence activity, and thus the macromolecule materials with the specific function can be further prepared.

Description

technical field [0001] The invention relates to a fluorescent active 2-(3-aminophenoxy)-6-(4-aminophenoxy)-N-(2-aminofluorene) benzamide monomer and a preparation method thereof, belonging to the field of functional polymer materials . [0002] technical background [0003] In the research field of organic electroluminescent materials, macromolecular electroluminescent materials have good mechanical properties, can be bent, and are relatively simple to prepare. When synthesizing macromolecular electroluminescent materials, macromolecular electroluminescent materials can be doped Miscellaneous, so that it has excellent carrier transport performance and luminescent performance; small molecule electroluminescent materials are the most abundant and most invested type of electroluminescent materials. Small-molecule electroluminescent materials have the advantages of diverse structures, simple purification, high fluorescence efficiency, and rich luminescent colors, and some of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/56C07C231/12C09K11/06
CPCC07C235/56C09K11/06C07C2603/18C09K2211/1007C09K2211/1011C09K2211/1014
Inventor 翟圣先牛永生董端柴德源林广成胡春旺韩楚楚
Owner ANYANG INST OF TECH
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