Photoelectric active dithiophene benzodithiophene conjugated polymer and preparation method and application thereof

A polymer and group technology, used in photovoltaic power generation, circuits, electrical components, etc., can solve the problems of molecular structure research and application that have not yet been reported, and achieve the effect of high photoelectric conversion efficiency and good hole mobility.

Active Publication Date: 2012-07-18
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the polymer system, the research and application of the molecular structure based on DTBDT as the main chain in the field of organic optoelectronics has not been reported.

Method used

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  • Photoelectric active dithiophene benzodithiophene conjugated polymer and preparation method and application thereof
  • Photoelectric active dithiophene benzodithiophene conjugated polymer and preparation method and application thereof
  • Photoelectric active dithiophene benzodithiophene conjugated polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、2

[0060] Example 1, 2,6-bis(trimethyltin base)-4,8-bis(2-hexyldecyl)-dithieno[2,3-d:2',3'-d']benzene Synthesis of [1,2-b:4,,5-b']dithiophene (7)

[0061] chemical reaction flow chart Figure 7 Shown, concrete reaction steps and reaction conditions are as follows:

[0062]Compound 2: Compound 1 (4mmol, 2.7g) was dissolved in chloroform (30ml), and liquid bromine (24mmol, 3.8g) in chloroform (20ml) was added dropwise at room temperature. After all the dropwise addition was completed, the mixture was stirred at room temperature for 20 hours. After the reaction was completed, the reaction solution was poured into 200 mL of saturated sodium thiosulfate solution. The organic phase of the mixture was extracted twice with chloroform, and the two extracted organic phases were combined for drying over anhydrous magnesium sulfate. Column chromatography with petroleum ether eluent gave the product as a white solid (3.52 g, 89%) after removal of the solvent.

[0063] 1 H NMR (400MHz, C...

Embodiment 2

[0073] Example 2, poly{[4,8-bis(2-hexyldecyl)-dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4, ,5-b′]dithiophene]-co-[4,7-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2,5]thiadiazole} (polymer Synthesis of PDTBDT-DTBT)

[0074] chemical reaction flow chart Figure 8 Shown, concrete reaction steps and reaction conditions are as follows:

[0075] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis(2-hexyldecyl)-dithieno[2,3-d:2′,3′-d′]benzo [1,2-b:4,,5-b']dithiophene (7) (0.555 g, 0.5 mmol) and the monomer 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene -2-yl) benzo[1,2,5]thiadiazole (0.341g, 0.5mmol), after dissolving it in toluene (25mL), exhaust the air with argon for 5 minutes, then add the catalyst tetrakis(triphenyl phosphine)palladium(0) (25 mg) and continued to evacuate the air for 25 minutes. Polymerization was then stopped after 14 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, slowly poured into methanol (50 mL), and the precipitated ...

Embodiment 3

[0076] Example 3, poly{[4,8-bis(2-hexyldecyl)-dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4, ,5-b']dithiophene]-co-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione}(polymer PBDF- Synthesis of Th-TPD)

[0077] chemical reaction flow chart Figure 9 Shown, concrete reaction steps and reaction conditions are as follows:

[0078] Take the monomer 2,6-bis(trimethyltin base)-4,8-bis(2-hexyldecyl)-dithieno[2,3-d2',3'-d']benzo[1 ,2-b: 4,,5-b′]dithiophene (7) (0.218g, 0.25mmol) and the monomer 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[ 3,4-c]pyrrole-4,6(5H)-dione (TPD, 0.105g, 0.25mmol), after dissolving it in a mixed solvent of toluene (8mL) and DMF (2mL), exhaust the air with argon After 5 minutes, the catalyst tetrakis(triphenylphosphine)palladium(0) (20 mg) was added and the air was continued to be exhausted 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 me...

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Abstract

The invention discloses a photoelectric active dithiophene benzodithiophene conjugated polymer and a preparation method and an application thereof. The structural formula of the polymer is shown as a formula I, wherein A1 and A2 independently represent any one of the following unsubstituted or substituent-containing groups: hydrogen, alkyl with 1-30 carbon atoms, alkoxyl with 1-30 carbon atoms, cyano-group, nitryl, ester group, aryl, aralkyl, halogen, haloalkyl, hetero-alkyl, vinyl, single bond, double bonds, triple bonds or combined substituent-substituted aryl; Ar is selected from any one of the following unsubstituted or substituent-containing groups: vinylidene, ethynylene, monocyclic ring arylidene, dicyclo-arylidene, arylidene containing at least three rings, monocyclic ring heteroarylidene, dicyclo-heteroarylidene and heteroarylidene containing at least three rings; and n represents the quantity of repeated units of the polymer, and is a natural number ranging from 5 to 1,000. The polymer provided by the invention has very high hole mobility and high photoelectric transformation efficiency.

Description

technical field [0001] The invention relates to a photoelectrically active dithienobenzodithiophene conjugated polymer, a preparation method and application thereof. Background technique [0002] Compared with inorganic semiconductor materials, the most important advantages of organic semiconductor materials are their molecular structure diversity and modifiability. By changing the molecular composition and elemental composition of organic molecules, the performance of organic materials can be adjusted in a wide range, and it is more likely to be fully close to the requirements of practical applications. In addition, the process of organic semiconductor materials is relatively simple, and large-area printing can be achieved by spin-coating printing. Therefore, in terms of functional materials, a large number of application fields that originally used inorganic materials have switched to organic materials in recent years. For example, the following fields mainly use organic...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08L65/00H01L51/46H01L51/54
CPCY02E10/549
Inventor 霍利军侯剑辉武岳
Owner INST OF CHEM CHINESE ACAD OF SCI
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