n,n'-diphenyl-n,n'-di(9,9-dimethylfluoren-2-yl)-n-hexyl-(4,4'-diaminophenyl)carbazole and its resolve resolution

A technology of hexylcarbazole and dimethyl, applied in the field of organic synthesis

Active Publication Date: 2017-10-24
PUYANG HUICHENG ELECTRONICS MATERIAL
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • n,n'-diphenyl-n,n'-di(9,9-dimethylfluoren-2-yl)-n-hexyl-(4,4'-diaminophenyl)carbazole and its resolve resolution
  • n,n'-diphenyl-n,n'-di(9,9-dimethylfluoren-2-yl)-n-hexyl-(4,4'-diaminophenyl)carbazole and its resolve resolution
  • n,n'-diphenyl-n,n'-di(9,9-dimethylfluoren-2-yl)-n-hexyl-(4,4'-diaminophenyl)carbazole and its resolve resolution

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
glass transition temperatureaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(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王朝杰席振峰
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap