Semiconductor conjugated polymer and preparation method thereof

A conjugated polymer and semiconductor technology, applied in the field of semiconductor conjugated polymers and their preparation, can solve the problems of expensive PCBM, poor compatibility, and affecting device performance.

Active Publication Date: 2014-03-12
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, almost all high-performance organic photovoltaic cells use PCBM material as the acceptor material, but PCBM also has obvious disadvantages as an organic photovoltaic acceptor material. First, the compatibility between PCBM and organic materials is poor, which is easy to cause polymer It forms a large-scale phase separation with PCBM, which affects the performance of organic photovoltaics; secondly, PCBM has weak absorption in the visible light region and basically no absorption in the near-infrared region, which causes the donor material to bear the effective absorption of solar photons, and the absorption of PCBM Weakness directly affects the current of the device, thereby affecting the performance of the device; finally, PCBM is expensive and expensive to use

Method used

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  • Semiconductor conjugated polymer and preparation method thereof
  • Semiconductor conjugated polymer and preparation method thereof
  • Semiconductor conjugated polymer and preparation method thereof

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preparation example Construction

[0029] The preparation method of each monomer is described as follows:

[0030] Preparation of two-dimensional conjugated benzodithiophene bistin monomer

[0031] The schematic diagram of the synthetic route of the two-dimensional conjugated benzodithiophene ditin monomer is shown in figure 2 As shown, the bistin monomer is prepared by the literature method, and the detailed preparation method can be found in the literature report (Polymer Chemistry, 2013, 4, 536-541.).

[0032] Preparation of (2-oxindol-3-ylidene)benzodifuran-dione dibromomonomers

[0033] The synthetic route of (2-oxindol-3-ylidene)benzodifuran-dione dibromomonomer is as follows figure 2 shown. For the detailed preparation method, please refer to the literature report (Chemical Communication, 2013, 49, 3790-3792.).

Embodiment 1

[0034] Embodiment 1, synthetic polymer P1

[0035] The synthetic route of polymer P1 is as follows image 3 As shown, the specific steps are: add 0.5mmol of bis-tin monomer and 0.5mmol of bis-bromine monomer (R1 and R2 are shown in Table 1) into a 100mL reaction bottle, then add 10mL of anhydrous toluene, replace with nitrogen for 40 minutes, Add 2% catalyst tris(dibenzylideneacetone) dipalladium, use tris(o-methylphenyl)phosphorus as ligand, react at 110oC for 24 hours, cool the reaction to room temperature, add 200mL of methanol to precipitate, filter the solid, respectively Soxhlet extraction with methanol and n-hexane for 24 hours, and then Soxhlet extraction with chloroform for 24 hours, and finally the liquid was rotary evaporated, methanol precipitated to obtain a black polymer.

Embodiment 2-3

[0037] The specific steps are the same as in Example 1: add 0.5 mmol of bistin monomer and 0.5 mmol of bis-bromine monomer (R1 and R2 are shown in Table 1) into a 100 mL reaction bottle, add 10 mL of anhydrous toluene, replace with nitrogen for 40 minutes, and add 2% Catalyst tris(dibenzylideneacetone)dipalladium, with tris(o-methylphenyl)phosphorus as ligand, react at 110oC for 24 hours, cool to room temperature, add 200mL of methanol to precipitate, and the solid is Soxhlet with methanol and n-hexane respectively Extracted for 24 hours, then Soxhlet extracted with chloroform for 24 hours, and finally the liquid was rotary evaporated, and methanol precipitated to obtain black polymers P2-P3, the specific structure of which is shown in Table 1.

[0038] Figure 4 The absorption spectrum of polymer P1 is given, and the absorption peak covers visible light and extends to the near-infrared region. Figure 5 The electrochemical curve of polymer P1 is given, and it can be concluded ...

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Abstract

The invention relates to a semiconductor conjugated polymer and a preparation method thereof. The invention discloses a solution-processable polymer semiconductor material and particularly relates to a semiconductor conjugated polymer based on two-dimensional conjugated dibenzothiophene and (2-oxyindole-3-subunit)dibenzofuran-diketone and preparation thereof. The synthesized semiconductor conjugated polymer has wide absorption peak which covers visible light, even extends to a near infrared region; in addition, the synthesized semiconductor conjugated polymer has low lowest unoccupied molecular orbital (LUMO) energy level and can replace fullerene derivative (PCBM) to serve as a photovoltaic receptor material applied to the organic photovoltaic field. The introduced side chain serves as a solubilized alkyl chain. The semiconductor conjugated polymer prepared by the method can be subjected to solution processing, and has a certain application prospect in the organic photovoltaic field.

Description

technical field [0001] The present invention relates to a solution-processable polymer semiconductor material, specifically a two-dimensional conjugated benzodithiophene and (2-oxindole-3-ylidene)benzodifuran-diketone semiconducting conjugated polymers and their preparation. The polymer has a low LUMO energy level, and the absorption peak extends to cover visible light and extends to the near-infrared region. The polymer of the invention can replace fullerene derivatives (PCBM), increase light absorption, and be applied in the field of organic photovoltaics. Background technique [0002] In recent years, organic photovoltaic has become a research hotspot because of its outstanding advantages, such as low cost, light weight, and solution processing, and it is an important part of utilizing renewable energy in the future. Bulk heterojunction (BHJ) is the most basic device structure currently used in organic photovoltaics. It uses organic materials such as conjugated polymers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
Inventor 张国兵郭景华张捷李朋吕国强
Owner HEFEI UNIV OF TECH
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