Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

1-alkyl-2-substituted phenyl benzimidazole compound synthesis method and application

A technology of phenylbenzimidazole and synthesis method, which is applied in chemical instruments and methods, organic chemistry, electrical components, etc., and can solve problems such as harsh reaction conditions, high reaction cost, and low yield

Inactive Publication Date: 2011-09-07
NANJING UNIV OF TECH
View PDF1 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the reported method for synthesizing benzimidazoles, there are two ways to introduce fluorescent groups: one is to introduce through Buchwald-Hartwig cross-coupling reaction, which requires special catalysts or oxidants (such as triphenylphosphine di palladium chloride, cobalt acetate, etc.), the reaction cost is high; the other is to carry out structural modification by Suzuki coupling reaction, and this type of reaction needs to synthesize phenylboronic acid at low temperature under anhydrous and oxygen-free conditions as raw material, and requires catalyst, reaction conditions Harsh, lower yield

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
  • 1-alkyl-2-substituted phenyl benzimidazole compound synthesis method and application
  • 1-alkyl-2-substituted phenyl benzimidazole compound synthesis method and application
  • 1-alkyl-2-substituted phenyl benzimidazole compound synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: 2-(4-phenylenesulfide phenyl)-6-methylbenzimidazole

[0038] Add 2.44g (20mmol) of 4-methyl o-phenylenediamine, 4.22g (20mmol) of p-phenylene sulfide benzonitrile, 20mL of phosphoric acid, and 25mL of polyphosphoric acid into a 50mL four-necked flask, and slowly heat up to 190°C. React at this temperature for 12 hours, cool to 70°C, pour the reaction solution into 500mL of water, precipitate a yellow-brown solid, filter with suction, adjust the pH of the filter cake to 8 with 10% sodium hydroxide solution, heat to reflux for 8 hours, and heat filter to obtain the crude product. Then recrystallized from absolute ethanol to obtain 5.19 g of light yellow solid with a yield of 82.2%.

Embodiment 2

[0039] Example 2: Synthesis of 2-(4-(p-tert-butylphenylsulfide) phenyl)-6-methylbenzimidazole

[0040] Add 2.44g (20mmol) of 4-methyl-o-phenylenediamine, 5.34g (20mmol) of 4-(p-tert-butylphenylsulfide)benzonitrile, 20mL of phosphoric acid, and 25mL of polyphosphoric acid into a 50mL four-necked flask. Slowly raise the temperature to 190°C, react at this temperature for 12 hours, cool to 70°C, pour the reaction solution into 500mL of water, a yellow solid precipitates, filter with suction, adjust the pH of the filter cake to 8 with 10% sodium hydroxide solution, and heat to reflux for 8h , hot filtration to obtain the crude product, and then recrystallized from absolute ethanol to obtain 5.96 g of off-white solid, with a yield of 80.2%.

Embodiment 3

[0041] Embodiment 3: the synthesis of 2-(4-phenoxyphenyl)-6-methylbenzimidazole

[0042] Add 2.44g (20mmol) of 4-methyl o-phenylenediamine, 4.00g (20mmol) of p-phenoxybenzonitrile, 20mL of phosphoric acid, and 25mL of polyphosphoric acid into a 50mL four-neck flask, and slowly heat up to 190°C. React at high temperature for 12 hours, cool to 70°C, pour the reaction solution into 500mL water, precipitate a yellow solid, filter with suction, adjust the pH of the filter cake to 8 with 10% sodium hydroxide solution, heat and reflux for 8 hours, heat filter to obtain the crude product, and then pass Recrystallization from absolute ethanol gave 5.00 g of off-white solid with a yield of 83.4%.

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

No PUM Login to View More

Abstract

The invention provides a 1-alkyl-2-substituted phenyl benzimidazole compound organic light-emitting material as well as a preparation method and application thereof. The preparation method comprises the following steps of: firstly, carrying out condensation reaction on an o-phenylenediamine compound and an aromatic cyanogens compound under the catalytic action of phosphoric acid and polyphosphoric acid to obtain a series of 2-substituted phenyl benzimidazole compounds; and reacting doubled 2-substituted phenyl benzimidazole compounds with 1.0-1.5 times of halogenated hydrocarbon or halogenated olefin under the action of 1.0-6.0 times of sodium hydride for 4-24 hours at 10-80 DEG C to obtain a series of 1-alkyl-2-substituted phenyl benzimidazole compounds. The 1-alkyl-2-substituted phenyl benzimidazole compounds can be used as a light-emitting layer or electronic transmission layer of an organic light-emitting diode.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. Specifically, it relates to a synthesis method and application of 1-hydrocarbyl-2-substituted phenyl benzimidazole compounds. The compound has luminescence and electron transport properties, and can be used as an organic light-emitting blue light material or an electron transport material for light-emitting devices, organic light-emitting diodes, and the like. technical background [0002] Organic light-emitting diode (OLED) is a new generation of flat display technology based on organic electroluminescent material technology, so it is recognized by the industry as the most ideal and most promising next-generation display technology (Mei - Yi Lai. Angew. Chem. 2008, 120, 591-595). This new display technology has almost all the excellent features required by the display device manufacturing industry. So far, people have discovered some green and red light materials with excellen...

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
IPC IPC(8): C07D235/18C07D401/10C07D403/10C09K11/06H01L51/50H01L51/54
Inventor 朱红军吴涛施红姜鹏王昆彦陈琛王凯章勤施路
Owner NANJING UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com