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N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and synthetic method thereof

A kind of technology of diaminophenyl and dimethyl fluorene, applied in the field of organic synthesis

Active Publication Date: 2016-03-09
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no reports on compounds that combine aromatic amine compounds with carbazole and fluorene functional groups. The research and development of such compounds will help improve the performance of organic electroluminescent materials and their development and utilization.

Method used

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  • N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and synthetic method thereof
  • N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and synthetic method thereof
  • N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and synthetic method thereof

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Embodiment 1

[0026] (1) Synthesis of 2,7-dibromo-N-hexylcarbazole (a)

[0027] Under the protection of argon, 4.88g (15mmol) of 2,7-dibromocarbazole, 0.72g of sodium hydride, and 30mL of DMSO solvent were sequentially added to a 100mL three-necked flask, and the reaction temperature was controlled at 20-30°C, and 1-bromocarbazole was added dropwise. n-Hexane, HPLC detects that the reaction is complete. Quench with 100mL of water, extract with 100mL of dichloromethane, separate layers, extract the aqueous layer with 50mL of dichloromethane, combine the organic phases, dry over anhydrous magnesium sulfate, recover the solvent under reduced pressure to obtain a solid crude product, and carry out extraction with dichloromethane-methanol After recrystallization, 5.87 g of white product 2,7-dibromo-N-hexylcarbazole was obtained, with a purity of 99.8% (HPLC), a yield of 95.6%, and a melting point of 70.6-72.5°C. 1 HNMR (400MHz, CDCl 3 ), δ: 0.858-0.906 (3H, t), 1.295-1.351 (6H, m), 1.786-1.885...

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Abstract

The invention discloses N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and a synthetic method thereof and belongs to the field of organic synthesis. According to the synthetic method, 2,7-dibromo-carbazole is used as a raw material and subjected to N-alkylation and a Suzuki coupled reaction to synthesize 2,7-di(4-bromophenyl)-N-hexyl carbazole; 2-bromo-9,9-dimethyl fluorene and aniline are used as raw materials and subjected to a Buchwald-Hartwig coupled reaction to synthesize 9,9-dimethyl-N-phenyl fluorine-2-amine; lastly, 2,7-di(4-bromophenyl)-N-hexyl carbazole and the 9,9-dimethyl-N-phenyl fluorine-2-amine are used as raw materials and subjected to a Buchwald-Hartwig coupled reaction to synthesize a target compound. The target compound has good heat stability and glass transition temperature and is suitable for hole transport materials of organic light-emitting devices.

Description

technical field [0001] The present invention relates to 9,9-dimethylfluorene-modified 2,7-disubstituted carbazole compounds and a synthesis method thereof, in particular to N,N'-diphenyl-N,N'-bis(9,9- The invention discloses dimethylfluoren-2-yl)-N-hexyl-(4,4'-diaminophenyl)carbazole and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] Aromatic amine compounds have the characteristics of high hole mobility, excellent electrochemical performance and host luminescence, and have been widely studied and applied as hole transport materials and luminescent materials. Carbazole is a typical electron-rich group. Conjugated π electrons endow it with excellent photoelectric performance, good hole transport ability and high luminescence ability. Its derivatives have strong ultraviolet absorption intensity and can emit blue light with a band gap around 3.20eV. . In addition, fluorene has a wide energy gap and high luminous efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029
Inventor 孙敏青陈鹏丽屈凤波杨振强周铎杨瑞娜陈辉
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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