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

Anthracene-diazosulfide copolymer, and preparation method and application thereof

A technology of benzothiadiazoles and copolymers, which is applied in the field of organic compound synthesis, can solve problems such as limiting the scope of application, and achieve the effects of increasing the absorption range, reducing the energy gap, and being easy to operate and control.

Inactive Publication Date: 2011-08-24
OCEANS KING LIGHTING SCI&TECH CO LTD +1
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been many reports on anthracene and its derivatives as organic electroluminescent materials, there are few reports on organic photovoltaic materials, which greatly limits its application range.

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
  • Anthracene-diazosulfide copolymer, and preparation method and application thereof
  • Anthracene-diazosulfide copolymer, and preparation method and application thereof
  • Anthracene-diazosulfide copolymer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)yl-anthracene:

[0055]

[0056] Set up an anhydrous and anaerobic reaction device, under constant stirring and N 2 Under the protection of the three-necked flask, add 7.2mmol of light yellow crystal 9,10-dibromoanthracene, and inject 120ml of tetrahydrofuran solvent, and then slowly inject 21.6mmol of n-BuLi at -78°C to react while stirring After 2 hours of reaction, the system gradually changed from light yellow to orange.

[0057] After reacting for 2 hours, inject 24.5mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at -78°C until the system After the red color changed to pale yellow, the temperature was raised to room temperature and the reaction was continued for 12 hours.

[0058] After the reaction is over, add saturated aqueous sodium chloride solution, then extract with chloroform, then dry with anhydrous sodium sulfate, filter, then collect the filtrate and rotary evaporate the solve...

Embodiment 2

[0060] Preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-2,6-bis(2-octyldecyl)anthracene:

[0061]

[0062] Set up an anhydrous and anaerobic reaction device, under constant stirring and N 2 Under the protection of 9,10-dibromo-2,6-bis(2-octyldecyl)anthracene 5mmol into the three-necked flask, and inject 150ml of tetrahydrofuran solvent, then slowly inject 15mmol n -BuLi, while stirring for 2 hours, inject 15mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at -78°C, After 52 hours of reaction, the temperature was raised to room temperature and the reaction was continued for 8 hours. After the reaction, add saturated aqueous sodium chloride, then extract with chloroform, then dry with anhydrous sodium sulfate, filter, then collect the filtrate and rotary evaporate the solvent to obtain a crude product, and finally separate the crude product by silica gel column chromatography , to obtain a powdery solid with a yield of 61%. GC-MS (EI-m / z): 959 (M+)....

Embodiment 3

[0064] Preparation of anthracene and 2,1,3-benzothiadiazole copolymer PAn-BT:

[0065]

[0066] Add 1.0 mmol of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) anthracene, 4,7-dibromo-2 to the reactor, 1,3-benzothiadiazole 1.0mmol, tetrakistriphenylphosphine palladium 0.01mmol, 2mol / L Na 2 CO 3 2.8ml of aqueous solution and 20ml of toluene solvent, through the uninterrupted flow of N 2 Keep the reaction system in an oxygen-free environment by vacuuming, and react at 94° C. for 24 hours. After the reaction is over, add deionized water and toluene to the reaction bottle for extraction, keep the organic phase, and then use the vacuum distillation method to spin-evaporate the mixed solution of the copolymer and toluene to about 5ml, and then drop it into a 300ml After being stirred continuously for about 4 hours in anhydrous methanol, flocculent solids were precipitated, and then solid powder was obtained after suction filtration and drying. Dissolve the solid powder in c...

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 discloses an anthracene-diazosulfide copolymer disclosed as a general formula (I), and a preparation method and application thereof. In the absence of oxygen, oxapentaborane anthracene compounds and bromine-substituted diazosulfide compounds are subjected to polymerization reaction under weakly alkaline conditions to obtain the target copolymer. The preparation method disclosed by the invention is simple and easy to operate and control, and is suitable for industrial production. The target copolymer prepared by the method disclosed by the invention can effectively reduce the energy gap of the material, and widen the spectral absorption range, thereby being beneficial to the effective transfer of the carrier inside the active layer material.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a copolymer containing anthracene and benzothiadiazole and its preparation method and application. Background technique [0002] High-efficiency solar cells are usually made of inorganic semiconductors, but the main silicon solar cells currently on the market are complicated in the production process, serious in pollution, high in energy consumption, and high in cost, which inhibits the development of its commercial application. Therefore, the preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. On the one hand, organic semiconductor materials have good environmental stability, low preparation cost, easy function modulation, good flexibility and film-forming properties; on the other hand, organic solar cells have relatively simple processing and...

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): C08G61/12H01L51/00
Inventor 周明杰黄杰黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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