Anthracene and benzothiadiazole 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 the problems of mismatching device spectral response and solar radiation spectrum, ineffective use of red light region, and low collection efficiency of carrier electrodes. , to achieve high mobility, excellent reduction reversibility, and improved absorption coverage

Inactive Publication Date: 2011-11-09
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research of polymer solar cells mainly focuses on the blending system of donor and acceptor. The energy conversion efficiency of PCPDTBT and PCBM blending system has reached 6.5%, but it is still much lower than the conversion efficiency of inorganic solar cells. The main constraints to performance improvement are: the relatively low carrier mobility of organic semiconductor devices, the spectral response of the device does not match the solar radiation spectrum, the red region of high photon flux is not effectively utilized, and the electrode of the carrier low collection efficiency

Method used

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  • Anthracene and benzothiadiazole copolymer, and preparation method and application thereof
  • Anthracene and benzothiadiazole copolymer, and preparation method and application thereof
  • Anthracene and benzothiadiazole copolymer, and preparation method and application thereof

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preparation example Construction

[0040] And, the embodiment of the present invention also provides the preparation method of the copolymer containing anthracene and benzothiadiazole, including the following chemical reaction formula:

[0041]

[0042] That is, the specific process steps included are:

[0043] Compounds A and B represented by the following structural formula are provided respectively,

[0044] Among them, R 1 , R 2 selected from -H, cyano, halogen, or from substituted or unsubstituted C 1 ~C 40 Alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; R 3 , R 4 selected from -H, cyano, or selected from substituted or unsubstituted C 1 ~C 40 Alkyl, substituted or unsubstituted C 1 ~C 40 Alkoxy, substituted or unsubstituted C 6 ~C 40 Aryl, substituted or unsubstituted C 6 ~C 40 Aralkyl, substituted or unsubstituted C 6 ~C 40 Arylalkoxy, Ar is an organic group with electron-donating properties;

[0045] In an oxygen-free and alkaline environment and i...

Embodiment 1

[0055] Containing the preparation of anthracene and benzothiadiazole copolymer PA-BFB, its structural formula is as follows:

[0056]

[0057] 1) The preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan) base-anthracene, its reaction is shown in the following formula:

[0058]

[0059] The specific process of preparation is: set up an anhydrous and anaerobic reaction device, and continuously stir and N 2 Under the protection of the three-necked flask, add 9.0mmol of light yellow crystal 9,10-dibromoanthracene, then inject 150ml of refined tetrahydrofuran solvent with a syringe, and then slowly inject 27.0mmol of n- BuLi reacted with each other, and the system gradually changed from light yellow to orange. After stirring the reaction for 2 hours, inject 30.6mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with a syringe at -78°C, the system From orange to light yellow, warmed up to room temperature and reacted overnight. After the reaction, add satur...

Embodiment 2

[0067] Containing the preparation of anthracene and benzothiadiazole copolymer PODA-BFB, its structural formula is as follows:

[0068]

[0069] 1) 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-2,6-bis(2-octyldecyl)anthracene Preparation, its reaction is shown in the following formula:

[0070]

[0071] Set up an anhydrous and anaerobic reaction device, stirring and N 2 Under the protection of 9,10-dibromo-2,6-bis(2-octyldecyl)anthracene 5mmol into the three-necked flask, inject 150ml of refined tetrahydrofuran solvent with a syringe, and then re- Slowly inject 15mmol n-BuLi with a syringe, and stir for 2 hours; after 2 hours of reaction, inject 15mmol 2-isopropoxy-4,4,5,5-tetramethyl-1 with a syringe at -78°C , 3,2-dioxaborolane, warmed to room temperature and reacted overnight. After the reaction, add saturated aqueous sodium chloride solution, extract with chloroform, dry over anhydrous sodium sulfate, collect the filtrate after filtration and rotary evaporate t...

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Abstract

The invention discloses an anthracene and benzothiadiazole copolymer, and a preparation method and application thereof. The anthracene and benzothiadiazole copolymer has a general molecular structure formula shown in (I), wherein R1 and R2 are selected from -H, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, cyano or halogen; R3 and R4 are selected from -H, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C6-C40arylalkyl, and substituted or unsubstituted C6-C40 alkoxy or cyano; n is the polymerization degree and is a natural number ranging from 1 to 500; and Ar is an organic group with an electron donating property. The anthracene and benzothiadiazole copolymer disclosed by the invention has the advantages of low energy gap, high carrier mobility and wide spectral absorption range, and improves the photoelectric conversion efficiency. The preparation method of the anthracene and benzothiadiazole copolymer is simple in process, high in product yield, and easy to operate and control.

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, and the use of cheap materials to prepare low-cost, high-efficiency solar cells has always been a research hotspot and difficulty in the field of photovoltaics. At present, silicon solar cells used on the ground are complicated in production process, serious in pollution, high in energy consumption, and high in cost, which inhibits the development of its commercial application. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54H01L51/30
CPCY02E10/50Y02E10/549
Inventor 周明杰黄杰黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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