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Benzodifuran conjugated polymer material and preparation method and application thereof

A polymer and group technology, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of spectral response range radiation spectrum mismatch, low electrode collection efficiency, low carrier mobility, etc.

Active Publication Date: 2012-04-11
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In order to improve its energy conversion efficiency, starting from the perspectives of material synthesis, device structure, and device preparation, many chemists, physicists and material scientists have conducted in-depth research on polymer solar cells and found that restricting their energy conversion efficiency The main factors are that the spectral response range of the battery does not match the solar ground radiation spectrum, the mobility of the carriers is not high, and the collection efficiency of the electrode is low.

Method used

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  • Benzodifuran conjugated polymer material and preparation method and application thereof
  • Benzodifuran conjugated polymer material and preparation method and application thereof
  • Benzodifuran conjugated polymer material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、2

[0064] Embodiment 1,2,2,6-bis(trimethyltin base)-4,8-bis(isooctyloxy)-benzo[1,2-b:4,5-b '] the synthesis of difuran

[0065] chemical reaction flow chart Figure 7 Shown, concrete reaction steps and reaction conditions are as follows:

[0066] N,N-Diacetamide-3-furan (compound 2, 28.47 g, 0.17 mol) synthesized according to the method disclosed by Keiji Kobayashi [J.Org.Chem.2000, 65, 2577-2579] was dissolved in anhydrous tetrahydrofuran (150 mL), n-butyl lithium (75 mL, 2.5 M) was added dropwise to the above reaction system in 5 minutes under an ice-water bath at 0° C., then slowly warmed to room temperature and kept stirring overnight. After 15 hours, dilute hydrochloric acid (100 mL, 3 mol / L) was added to the reaction system to quench the reaction. The organic phase of the mixture was extracted twice with dichloromethane, and the two extracted organic phases were combined and dried over anhydrous magnesium sulfate. After removal of the solvent, recrystallization with acet...

Embodiment 2

[0072] Example 2. Poly[4,8-bis(isooctyloxy)benzo[1,2-b:4,5-b']difuran-2,6-diyl]-co-[4,7 - Synthesis of bis(4-(2-ethylhexyl)thiophen-2yl)-2,1,3-benzothiadiazol-5,5'-yl] (polymer 1).

[0073] chemical reaction flow chart Figure 8 Shown, concrete reaction steps and reaction conditions are as follows:

[0074] Take monomer 2,6-bis(trimethyltin base)-4,8-bis(isooctyloxy)-benzo[1,2-b:4,5-b']difuran (compound 5 , 0.37g, 0.5mmol) and the monomer 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2,5]thiadiazole (DTBT, 0.341g, 0.5mmol), after it was dissolved in toluene (10mL), the air was exhausted with argon for 5 minutes, and the catalyst tetrakis(triphenylphosphine)palladium(0) (30mg) was added and the air was continuously exhausted for 25 minutes. Polymerization was then stopped at reflux temperature of toluene for 16 hours. The polymer solution was cooled to room temperature, slowly poured into methanol (50 mL), and the precipitated solid polymer was sequentially eluted w...

Embodiment 3

[0075] Example 3, poly{[4,8-di(isooctyloxy)benzo[1,2-b:4,5-b']difuran-2,6-diyl]-co-[1- Synthesis of Thienyl[3,4-b]thiophen-2yl-]-2-ethylhexyl-1-one}(Polymer 2)

[0076] chemical reaction flow chart Figure 9 Shown, concrete reaction steps and reaction conditions are as follows:

[0077]Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis(isooctyloxy)-benzo[1,2-b:4,5-b']difuran (compound 5, 0.259g, 0.35mmol) and monomer 1-[(4,6-dibromo-thienyl[3,4-b]thiophen-2yl-]-2-ethylhexyl-1-one (TT-C, 0.148g, 0.35mmol), after it is dissolved into the mixed solvent of toluene (8mL) and DMF (2mL), exhaust the air with argon for 5 minutes, then add catalyst tetrakis (triphenylphosphine) palladium (0) (20mg) After that, continue to exhaust air for 25 minutes. Polymerization was then stopped after 15 hours at the toluene reflux temperature. Polymer solution was cooled to room temperature, slowly poured into methanol (50mL), and the solid polymer precipitated out was successively in the Soxhlet e...

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Abstract

The invention discloses a benzodifuran conjugated polymer material and a preparation method and application thereof. The structural formula of the polymer is shown by a formula I, wherein A1, A2, R1 and R2 separately represent hydrogen, alkyl group with 1-30 carbon atoms, alkoxyl group with 1-30 carbon atoms, cyano group, nitro group, carbonyl group, ester group, aryl group, aralkyl group, halogen, haloalkyl, heteroalkyl, alkenyl, and aryl or conjugation unit substituted by a substituent group containing single bond, double bond, triple bond or the combination thereof; and Ar is selected fromthe groups substituted or unsubstituted: vinylidene, ethynylene, monocycle arylene, bicyclo-arylene, arylene with three or more rings, monocyclic heteroarylene, bicyclo-heteroarylene, heteroarylene with three or more rings and 1-6 of the groups condensed or connected. The polymer material disclosed by the invention can be applied to the photoelectric field such as organic solar cells and high-shift field effect transistors. The formula I is shown in the specification.

Description

technical field [0001] The invention relates to a benzodifuran conjugated polymer material and its preparation method and its application in photoelectric conversion and field effect devices. Background technique [0002] Solar energy is an inexhaustible and inexhaustible clean energy. Today, as fossil energy is increasingly exhausted and environmental pollution is becoming more and more serious, the research on solar cells that convert solar energy into electrical energy has become one of the high-tech countries that are particularly concerned about. In recent years, organic (including polymer) photovoltaic devices have become a research hotspot in solar cells due to their outstanding advantages of light weight, low cost, and flexible large-area devices, and their highest energy conversion efficiency has reached 7-8%. (Lijun Huo, Shaoqing Zhang, Xia Guo, Feng Xu, Yongfang Li, and Jianhui Hou Angew. Chem. Int. Ed. 2011, 50, 9697-9702; Samuel C. Price, Andrew C. Stuart, Liqia...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08L65/00H01L51/46H01L51/30
CPCY02E10/549
Inventor 霍利军侯剑辉
Owner INST OF CHEM CHINESE ACAD OF SCI
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