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

Dithiophene pentalene-fluoroquinoxaline conjugated polymer

A technology of phenocyclopentadiene and conjugated polymers, which is applied in the field of dithienocyclopentadiene-fluoroquinoxaline conjugated polymers to achieve the effect of increasing the open circuit voltage

Inactive Publication Date: 2012-12-12
XIAN MODERN CHEM RES INST
View PDF1 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the above-mentioned influence of fluorine atoms on material properties, the introduction of fluorine atoms into the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing donor-acceptor polymer is expected to further reduce HOMO and increase the open circuit voltage, thereby improving the photovoltaic performance of the device. performance, but there is no report on the preparation of such materials and their application in polymer photovoltaic cells

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
  • Dithiophene pentalene-fluoroquinoxaline conjugated polymer
  • Dithiophene pentalene-fluoroquinoxaline conjugated polymer
  • Dithiophene pentalene-fluoroquinoxaline conjugated polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline:

[0038] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 1)

[0039] Follow the reaction equation shown below:

[0040]

[0041] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 0.016mol) was dissolved in 150ml absolute ethanol, NaBH was added in batches at 0℃ 4 (11.1g, 0.29mol), then react at room temperature for 20h. After the reaction, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with brine, and finally anhydrous MgSO 4 dry. Concentrate to remove the organic solvent, and the crude product obtained is purified with a silica gel column. The eluent is n-hexane / ethyl acetate (25:1, v / v) to obtain 4-fluoro-3,6-dibromo-1,2 benzene Diamine 3.5g, yield 78%.

[0042] (2) The preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2) is carried out according to the reaction equation shown below:

[0043] ...

Embodiment 2

[0056] Example 2: Synthesis of 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline (compound 9)

[0057] Follow the reaction equation shown below.

[0058]

[0059] The synthesis method is the same as that of compound 5, except that 1,2-bis(3-octyloxyphenyl)ethanedione is replaced with 1,2-bis(4-octyloxyphenyl)ethanedione.

Embodiment 3

[0060] Example 3: Synthesis of 6,7-difluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline (Compound 14)

[0061] (1) Preparation of 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine (compound 11)

[0062] Follow the reaction equation shown below:

[0063]

[0064] 5,6-Difluoro-4,7-dibromo-2,1,3-benzothiadiazole (10g, 0.031mol) was dissolved in 300ml absolute ethanol, and NaBH was added in batches at 0℃ 4 (22.2g, 0.59mol), then react at room temperature for 5h. After the reaction, the ethanol was removed by rotating, 200ml of water was added, ethyl acetate was added, the organic phase was washed with saturated brine, and finally anhydrous MgSO 4 dry. The crude product obtained by concentration is purified with a silica gel column, and the eluent is n-hexane / ethyl acetate (20:1, v / v) to obtain 4,5-difluoro-3,6-dibromo-1,2-benzene Diamine 6.1g, the yield is 65%.

[0065] (2) Preparation of 6,7-difluoro-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 12)

[0066] Foll...

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 relates to a dithiophene pentalene-fluoroquinoxaline conjugated polymer the structure of which is as shown in a formula I. The polymer is prepared through Stille coupling reaction of a 2,6-di(trimethyltin)-4,4-di(2-ethylhexyl)-4-hydrogen-di-thiophene [3,2-b,2',3'-d] pentalane monomer serving as an electron donor unit and a di-bromine substituted fluoroquinoxaline monomer serving as an electron acceptor unit, and is used as a donor material of a bulk heterojunction solar cell. As for the polymer, a strong electron withdraw group fluorine atom is introduced to an electron-shortage unit quinoxaline to effectively reduce the HOMO energy level of the material, so that the open-circuit voltage of a polymer photovoltaic cell is improved.

Description

Technical field [0001] The invention belongs to the field of functional polymers, and specifically relates to a bisthienocyclopentadiene-fluoroquinoxaline conjugated polymer. Background technique [0002] With the increase in global energy demand year by year, the energy issue has become the primary problem encountered by the economic development of all countries in the world. As a kind of green energy, solar energy is inexhaustible and inexhaustible. It is one of the new energy sources developed and used by scientists from all over the world. Due to the high cost of raw materials of inorganic solar cells, complex production processes and severe light corrosion of narrow band gap semiconductors, solar energy Power generation cannot be widely promoted. To enable solar power to be applied on a large scale, it is necessary to reduce costs. Polymer solar cells have obvious advantages such as low cost, good flexibility, and easy preparation. Modification of materials can effectively...

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): C08G61/12H01L51/46
CPCY02E10/549
Inventor 高潮王维平武海梅刘红利陈冬安忠维陈键
Owner XIAN MODERN CHEM RES INST
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