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Benzopyrrolidiketone-based semiconductor polymer and preparation and purpose thereof

A technology of diketopyrrole and diketopyrrole, which is applied in the field of diketopyrrole-based semiconducting polymers and its preparation, can solve problems such as difficulty in large-scale application, and achieve low cost and low energy synthesis. Band gap, simple and effective synthesis method

Inactive Publication Date: 2012-08-22
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the limitation of high cost, it is difficult to carry out large-scale application

Method used

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  • Benzopyrrolidiketone-based semiconductor polymer and preparation and purpose thereof
  • Benzopyrrolidiketone-based semiconductor polymer and preparation and purpose thereof
  • Benzopyrrolidiketone-based semiconductor polymer and preparation and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, preparation of the semiconducting polymer of benzopyrrole diketope group

[0035] This example provides three kinds of soluble benzopyrrole diketope-based semiconducting polymers, the structural formula of which is shown in Table 1 (wherein, n≥1), and its synthetic route can be found in figure 1 .

[0036] Table 1

[0037]

[0038] 1.1. Preparation of compounds DP-111, DP-122 and DP-133

[0039] The preparation method of the polymer (DP-111, DP-122 and DP-133) containing benzopyrrole diketopyl group comprises the steps:

[0040] (a) Synthesis of Intermediate Compound A

[0041] The structural formula of intermediate compound A is

[0042] For its detailed preparation method, see the document "Greenhalgh, C.W., Carey, J.L. and Newton, D.F., the synthesis of quinodimethanes in the benzodifuranone anf benzodipyrrolidone series, Dyes Pigm., 1, 103-120, (1980)".

[0043] (b) Synthesis of compounds M1, M2 and M3

[0044] The structural formulas of...

Embodiment 2

[0051] Gel Permeation Chromatography, UV Absorption Spectrum and Electrochemical Properties of Embodiment 2, Polymer DP-133

[0052] image 3 The number average molecular weight measured by gel permeation chromatography (GPC) of the polymer is 20710, and the distribution coefficient PDI is 2.54. Figure 4 The ultraviolet absorption spectrum of polymer DP-133 in chloroform is given, its maximum absorption peak is around 614nm, and its optical band gap is 1.57eV. Figure 5 The cyclic voltammetry curve of compound DP-133 is given. The cyclic voltammetry test is carried out on the computer-controlled CHI610D telephone line analyzer, using the traditional three-electrode test system, the platinum electrode is the working electrode, the silver / silver ion electrode is the reference electrode, and the electrolyte is tetra-n-butyl hexafluorophosphoric acid Ammonium dichloromethane solution (0.1M), the scanning speed is 50mv / s, with ferrocene as a reference. The oxidation potential...

Embodiment 3

[0053] Embodiment 3, polymer DP-133 as the purposes in thin-film solar cell as hole transport material

[0054] Figure 7 A schematic structural diagram of a bulk heterojunction organic thin film solar cell device is given, which uses polymer DP-133 as hole transport material and P71BM as acceptor. Solar cell device test I-V curve see Figure 8 , the conversion efficiency data are shown in Table 2: the conversion efficiency of the preliminary test is 0.2%, and the device shows a high open circuit voltage (0.90V).

[0055] Table 2 The parameter data of the thin film solar cell device with DP-133 / PC71BM as the semiconductor layer

[0056]

[0057] In summary, the benzopyrrole diketope-based semiconducting polymers involved in the present invention are characterized in that they have a large π-conjugated main chain body with a rigid plane and flexible solubilized alkyl side chains, and have a low energy band gap, low HOMO energy level, and thin-film solar cell device test...

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Abstract

The invention relates to a benzopyrrolidiketone-based semiconductor polymer and preparation and a purpose thereof. The structural formula of a benzopyrrolidiketone derivative is as follow: FORMULA, wherein R1 is a C8-C20 paraffin chain; R2 is a C8-C20 paraffin chain; and n is not less than 1. The invention further relates to a preparation method of the benzopyrrolidiketone-based semiconductor polymer and a purpose of the benzopyrrolidiketone-based semiconductor polymer as a semiconductor active layer in an organic thin-film photovoltaic device. The benzopyrrolidiketone-based semiconductor polymer provided by the invention includes a novel, rigid-plane, big-pi-conjugated and soluble benzopyrrolidiketone unit and the flexible and solution-promoting paraffin chains, and is a main-chain-conjugated and low-energy-gap polymer processed by a soluble solution, and the research on the thin-film photovoltaic device shows that the material has thin-film photovoltaic application potential.

Description

technical field [0001] The invention relates to a solution-processable organic semiconductor material, in particular to a benzopyrrole diketone-based semiconductor polymer and its preparation and use. Background technique [0002] The energy problem has increasingly become the primary problem that countries all over the world need to face and solve. Solar energy among renewable energy sources has received significant attention. At present, the development of inorganic solar cells is rapid, and the photoelectric conversion efficiency is continuously improved. However, due to the limitation of high cost, it is difficult to carry out large-scale application. Organic polymer solar cells have received great attention from scientific researchers in recent years. The characteristics of organic polymer solar cell materials are that there are many types of organic materials, the structure can be tailored, and the performance can be adjusted. It can realize solution processing and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00H01L51/46
CPCY02E10/549
Inventor 邓平张清李树岗曹康丽胡超
Owner SHANGHAI JIAO TONG UNIV
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