Polymer material containing anthracene and diketopyrrolopyrrole units and its preparation method and application

A technology of diketopyrrolopyrrole and polymer materials, applied in the field of organic semiconductor materials, can solve the problems of affecting the efficiency of exciton diffusion, reducing the photoelectric conversion efficiency of organic solar cells, poor solubility, etc., and achieving high photoelectric conversion efficiency and convenient The effect of promoting the application

Inactive Publication Date: 2011-12-14
OCEANS KING LIGHTING SCI&TECH CO LTD +1
View PDF1 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Diketopyrrolopyrrole or its derivatives have extremely high stability to light, heat and different climate environments, but due to the strong π-π conjugation and molecular hydrogen bonds in the molecular structure, their solubility is poor, so Poor film-forming processing performance, which leads to the phase separation problem of the prepared device, which affects the efficiency of exciton diffusion and high energy loss
At the same time, the absorption spectrum of pyrrolopyrrole or its derivatives is narrow, and the matching degree with the emission spectrum of sunlight is not high enough, so sunlight cannot be effectively used, and the photoelectric conversion efficiency of organic solar cells will also be reduced.

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
  • Polymer material containing anthracene and diketopyrrolopyrrole units and its preparation method and application
  • Polymer material containing anthracene and diketopyrrolopyrrole units and its preparation method and application
  • Polymer material containing anthracene and diketopyrrolopyrrole units and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 This example discloses polymer P1 with the following structure:

[0043]

[0044] The preparation steps of P1 are as follows:

[0045] Step 1, the preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) base anthracene:

[0046]

[0047] Set up the tetrahydrofuran (THF) distillation device, add the tetrahydrofuran solvent that has been dried with KOH for several days into a 1000ml single-necked bottle, then cut into the sodium block and add benzophenone, keep stirring and reflux until the system is dark purple, evaporate Refined THF is ready for use.

[0048] Set up an anhydrous and oxygen-free reaction device, under the protection of constant stirring and N2, add 9.0mmol of light yellow crystal 9,10-dibromoanthracene into the three-necked flask, inject 150ml of the above-mentioned refined tetrahydrofuran solvent with a syringe, and in- Slowly inject 27.0mmol n-BuLi with a syringe at 75°C, the system gradually changes from light yellow to oran...

Embodiment 2

[0070] Example 2 This example discloses polymer P2 with the following structure:

[0071]

[0072] The preparation steps of P2 are as follows:

[0073] Step 1, the preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) base anthracene:

[0074] For its preparation, see Step 1 in Example 1.

[0075] Step 2, the preparation of 3,6-dithienyl-diketopyrrolopyrrole:

[0076] For its preparation, refer to Step 2 in Example 1.

[0077] Step 3, the preparation of 2,5-dioctyl-3,6-dithienyl-pyrrolopyrrole diketone:

[0078] For its preparation, see Step 3 in Example 1.

[0079] Step 4. Preparation of 2,5-dioctyl-3,6-bis(5-bromothiophene)yl-diketopyrrolopyrrole:

[0080] For its preparation, see Step 4 in Example 1 for details.

[0081] Step 5. Preparation of 2,5-dioctyl-3,6-bis(4-dodecyldithiophene)yl-diketopyrrolopyrrole:

[0082]

[0083] Dissolve 1 mmol of 2,5-dioctyl-3,6-bis(5-bromothiophene)-pyrrolopyrrole diketone and 2.3 mmol of 4-dodecyl-2-tributyltin-based...

Embodiment 3

[0092] Example 3 This example discloses polymer P3 with the following structure:

[0093]

[0094] The preparation steps of P3 are as follows:

[0095] Step 1. 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-2,6-bis(2-octyldecyl)anthracene Preparation of:

[0096]

[0097] Set up an anhydrous and anaerobic reaction device, under the protection of constant stirring and N2, add 9,10-dibromo-2,6-bis(2-octyldecyl)anthracene 5mmol in the three-necked flask (the compound method Refer to Klaus Mullen et al's Macromol.Chem.Phys.2006, 207, 1107-1115), inject 150ml of refined tetrahydrofuran solvent with a syringe, slowly inject 15mmol n-BuLi with a syringe at -80°C, and stir the reaction 2 Hours; after 2 hours of reaction, inject 15mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with a syringe at -80°C, and raise the temperature React overnight at room temperature.

[0098] After the reaction, add saturated aqueous sodium chloride solution, extract with chloroform,...

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 polymeric material containing anthracene and a pyrrole-pyrrole-dione unit, a preparation method thereof and an application thereof. The polymeric material which has a structural formula (III) shown in the specification is copolymerized from anthracene, and pyrrole-pyrrole-dione or derivatives thereof. In the invention, groups for improving the solubility are introduced into pyrrole-pyrrole-dione at the second position and the fifth position to improve the solubility and the film forming ability of the polymeric material, and substituents at third and the sixth position of pyrrole-pyrrole are changed to regulate light absorption range of pyrrole-pyrrole-dione. So the obtained polymeric material containing anthracene and the pyrrole-pyrrole-dione unit has the advantages of good dissolvability, wide spectrum absorption range, and high energy conversion efficiency, can be applied to the organic solar cell field, the organic electroluminescent field, the organic field effect transistor field, the organic optical storage field, the organic non-linear material field, the organic laser field and the like as organic semiconductor materials.

Description

【Technical field】 [0001] The invention relates to the field of organic semiconductor materials, in particular to an organic semiconductor containing anthracene and diketopyrrolopyrrole units and a preparation method and application thereof. 【Background technique】 [0002] 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, polymer materials have good environmental stability, low preparation cost, easy modulation of functions, good flexibility and film-forming properties of organic materials; It has attracted much attention due to its low cost and other advantages, and has become a cheap and attractive solar cell material. [0003] Diketopyrrolopyrrole or its derivatives have extremely high stability to light, heat and different climate environments, but due to the strong π-π conjugation and molecular hydrogen bonds in the molecular structure, their...

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): C08G61/12C07D487/04C07D519/00H01L51/46H01L51/54H01L51/30
CPCY02E10/50Y02E10/549
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 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