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

Pyrene derivative as well as preparation method and application thereof

A technology of derivatives and reactions, which is applied in the field of pyrene derivatives and their preparation, can solve the problems of low fluorescence quantum yield and complicated preparation methods of pyrene-based blue light materials, and improve the charge transport ability. The effect of color purity and stability improvement

Inactive Publication Date: 2015-09-02
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
View PDF3 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. The preparation method is relatively complicated;
[0007] 2. The fluorescence quantum yield of pyrene-based blue light materials is low;

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
  • Pyrene derivative as well as preparation method and application thereof
  • Pyrene derivative as well as preparation method and application thereof
  • Pyrene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Preparation of 1-phenyl-6,8-bis-(4,4,-difluorodianiline)pyrene

[0075] The molecular structural formula of 1-phenyl-6,8-bis-(4,4,-difluorodianiline)pyrene is as follows:

[0076]

[0077] Concrete preparation steps are as follows:

[0078] The first step: under the condition of nitrogen protection, take pyrene 1g (4.9mmol) and benzyltrimethylammonium tribromide (NBS) 974mg (5.5mmol), dissolve in 50ml dichloromethane, stir at room temperature for 5 hours , filtered, and recrystallized in dichloromethane and n-hexane to obtain 1-bromopyrene (1.08g), with a yield of 78%;

[0079] The second step: under the condition of nitrogen protection, the first step product 1-bromopyrene 500mg (1.78mmol), phenylboronic acid 270mg (2.2mmol), tetrakis (triphenylphosphine) palladium 70mg (0.06mmol), potassium carbonate Add 300mg (2.2mmol) into a single-necked bottle, then add toluene (10ml) and ethanol (4ml), stir vigorously, keep the temperature at 90°C, reflux for 24 hours, filte...

Embodiment 2

[0085] Preparation of 1-phenyl-6,8-dicyanoprene

[0086] The molecular structural formula of 1-phenyl-6,8-dicyanoprene is as follows:

[0087]

[0088] Concrete preparation steps are as follows:

[0089]The first step: under the condition of nitrogen protection, take pyrene 1g (4.9mmol) and NBS974mg (5.5mmol), dissolve in 50ml of dichloromethane, stir at room temperature for 5 hours, filter, and weigh in dichloromethane and n-hexane Crystallization gave 1-bromopyrene (1.08g) with a yield of 78%;

[0090] The second step: under the condition of nitrogen protection, the first step product 1-bromopyrene 500mg (1.78mmol), phenylboronic acid 270mg (2.2mmol), tetrakis (triphenylphosphine) palladium 70mg (0.06mmol), potassium carbonate Add 300mg (2.2mmol) into a single-necked bottle, then add toluene (10ml) and ethanol (4ml), stir vigorously, keep the temperature at 90°C, reflux for 24 hours, filter the product, and go through column chromatography or recrystallization to obtain...

Embodiment 3

[0096] Preparation of 1-phenyl-6-bis-(4-ethynylbiphenyl)pyrene

[0097] The molecular structural formula of 1-phenyl-6-bis-(4-ethynylbiphenyl)pyrene is as follows:

[0098]

[0099] The specific preparation method is as follows:

[0100] The first step: under the condition of nitrogen protection, take pyrene 1g (4.9mmol) and iso-tert-butyl chloride 450mg (4.9mmol) as raw materials, in AlCl 3 Under the catalysis of 1.4g (9mmol), in dichloromethane solution (50ml), stir at room temperature for 5 hours, filter, and recrystallize in n-hexane to obtain 2-tert-butylpyrene (1.9g), the yield is 83%;

[0101] The second step: under the condition of nitrogen protection, take 2-tert-butylpyrene 2.58g (1mmol), BTMABr 3 4.41g (3.5mmol) was used as raw material, dissolved in dichloromethane solution (30ml), stirred at room temperature for 12 hours, filtered, and recrystallized in dichloromethane and n-hexane to obtain 7-tert-butyl-1,3- Dibromopyrene 3.02g, the productive rate is 78%;...

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
decomposition temperatureaaaaaaaaaa
Login to View More

Abstract

The invention relates to the field of organic electroluminescent materials, and in particular relates to a pyrene derivative as well as a preparation method and application thereof; the pyrene derivative provided by the invention is that large substituent group units having different electronic properties and rigid structures are introduced at the positions of 1-, 3-, 6- and 8- of pyrene; intermolecular phi-phi stacking can be inhibited through molecular coplanar damage; therefore, an exciplex is difficult to form; the crystallization process is inhibited; the film-forming property is improved; therefore, the purpose of improving device properties is achieved; because an electron donor and an electron acceptor are introduced at special positions, a pyrene ring is asymmetrically functionalized; push-pull type molecular is constructed; intramolecular charge transfer is induced to generate; the charge transmission capability of the material is increased; and an organic light-emitting material having blue light property and high fluorescence quantum yield can be prepared. Compared with the existing light-emitting material, the light-emitting efficiency, the colour purity and the stability of the material are greatly improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a pyrene derivative and its preparation method and application. Background technique [0002] With the development of multimedia technology and the advent of the information society, the performance requirements of flat panel displays are getting higher and higher. Organic Light-Emitting Diodes (OLED) devices have shown great commercial application prospects in high-tech fields such as communications, information, display, lighting and new full-color flat-panel displays (Full-Color Flat-Panel Displays). A research hotspot at this stage. Many scientists have devoted themselves to the research of OLED and achieved remarkable results. [0003] At present, research on OLEDs is mainly focused on the fabrication of devices and the development of functional materials, and the development of organic light-emitting materials with unique electronic structures and lumin...

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 Applications(China)
IPC IPC(8): C07C211/61C07C209/10C07C255/52C07C253/30C07C15/60C07C2/86C09K11/06H01L51/54
Inventor 冯星郭长龙魏先福魏微大和武彦
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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