Two-dimensional conjugated dibenzofuran conjugated polymer material and preparation method and application thereof

A technology of polymers and groups, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve problems such as low carrier mobility, low electrode collection efficiency, and mismatching radiation spectrum in the spectral response range

Active Publication Date: 2012-07-18
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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  • Two-dimensional conjugated dibenzofuran conjugated polymer material and preparation method and application thereof
  • Two-dimensional conjugated dibenzofuran conjugated polymer material and preparation method and application thereof
  • Two-dimensional conjugated dibenzofuran conjugated polymer material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、2

[0072] Example 1, 2,6-bis(trimethyltin base)-4,8-bis(5-(2-ethylhexyl)thiophen-2 base)-benzo[1,2-b:4,5 Synthesis of -b']difuran

[0073] chemical reaction flow chart Figure 7 Shown, concrete reaction steps and reaction conditions are as follows:

[0074] 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, recrystallizati...

Embodiment 2

[0080] Example 2, poly{[4,8-bis(5-(2-ethylhexyl)thiophen-2 base)benzo[1,2-b:4,5-b']difuran-2,6- Synthesis of diyl]-co-[3-fluoro-thienyl[3,4-b]thiophen-2yl-]-2-ethylhexyl-1-one}(polymer PBDF-Th-TTCF).

[0081] chemical reaction flow chart Figure 8 Shown, concrete reaction steps and reaction conditions are as follows:

[0082] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis(5-(2-ethylhexyl)thiophen-2 base)-benzo[1,2-b:4,5- b']difuran (compound 5, 0.218g, 0.25mmol) and the monomer 4,6-dibromo-3-fluoro-thienyl[3,4-b]thiophen-2yl-]-2-ethylhexyl -1-ketone (TT-CF, 0.110g, 0.25mmol), dissolved in toluene (10mL), evacuated with argon for 5 minutes, then added the catalyst tetrakis(triphenylphosphine) palladium (0) (30mg ) and continue to exhaust the air 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 seque...

Embodiment 3

[0083]Example 3, poly{[4,8-bis(5-(2-ethylhexyl)thiophen-2 base)benzo[1,2-b:4,5-b']difuran-2,6- Synthesis of diyl]-co-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione}(polymer PBDF-Th-TPD)

[0084] chemical reaction flow chart Figure 9 Shown, concrete reaction steps and reaction conditions are as follows:

[0085] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis(5-(2-ethylhexyl)thiophen-2 base)-benzo[1,2-b:4,5- b']difuran (compound 5, 0.218g, 0.25mmol) and the monomer 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4, 6(5H)-diketone (TPD, 0.105g, 0.25mmol), dissolved in a mixed solvent of toluene (8mL) and DMF (2mL), exhausted the air with argon for 5 minutes, and then added the catalyst tetrakis(triphenyl phosphine)palladium(0) (20 mg) and continued to evacuate the air for 25 minutes. Polymerization was then stopped after 15 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, slowly poured into methanol (50 mL), and...

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Abstract

The invention discloses a two-dimensional conjugated dibenzofuran conjugated polymer photoelectric material and a preparation method and application thereof. The polymer has a structural formula as shown in formula I, wherein A1, A2, R1 and R2 independently represent any one of the following groups: hydrogen, C1-C30 alkyl group, C1-C30 alkoxy group, cyan group, nitro group, ester group, aryl group, aralkyl group, halogen, alkylogen group, heteralkyl group, alkenyl group, and aryl group substituted by a substituent of a single bond, a double bond, a triple bond or combination thereof; Ar1, Ar2 and Ar independently represent any one of the following unsubstituted groups or groups containing a substituent: vinylidene group, ethynylene group, single ring arylene group, double ring arylene group, arylene group containing at least three rings, single ring heteroarylene group, double ring heteroarylene group, and conjugated units of heteroarylene group containing at least three rings, and n is a natural number between 5 and 500. The polymer material disclosed by the invention can be applied in the photoelectric field such as organic solar batteries and the high-mobility field effect tube field. (Formula I).

Description

technical field [0001] The invention relates to a two-dimensional conjugated benzodifuran conjugated polymer material and its preparation method and application 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, Liqiang Yang, Huaxing Zhou , Wei Yo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C08L65/00H01L51/46
CPCY02E10/549
Inventor 霍利军侯剑辉
Owner INST OF CHEM CHINESE ACAD OF SCI
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