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Isoindigo derivative polymer with butadiene as space isolation group, preparation and use thereof

A space isolation, butadiene technology, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components and other directions, can solve the problems of IID distortion, high TIIHOMO energy level, reduce dihedral angle, etc., to achieve low synthesis cost, Simple and effective synthesis method

Inactive Publication Date: 2016-03-02
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(References: Jung, E.H; Jo, W.H; π-Extendedlowbandgappolymerbasedonisoindigoandthienylvinyleneforhighperformancepolymersolarcells.EnergyEnviron.Sci, 2014, 7, 650-654.) IID bridges the indolinone ring on both sides of the double bond, because the H atom on the benzene ring and the C=O The O atoms in the O atom have a steric repulsion effect, which causes the IID to be distorted and reduces the degree of Π-Π conjugation
Chen et al. designed and synthesized a new type of isoindigo thiophene isoindigo TII with a thiophene ring instead of a benzene ring, which can effectively reduce the dihedral angle. However, due to the high HOMO energy level of TII, the PV performance is not ideal.

Method used

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  • Isoindigo derivative polymer with butadiene as space isolation group, preparation and use thereof
  • Isoindigo derivative polymer with butadiene as space isolation group, preparation and use thereof
  • Isoindigo derivative polymer with butadiene as space isolation group, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This embodiment provides soluble extended isoindigo EBI-based conjugated polymers PEBI-BDTO and PEBI-BDTT, the structural formula of which is shown in Table 1 (wherein, 100>n>1), and the synthetic route of its monomer EBI see figure 1 , the synthesis of polymers PEBI-BDTO and PEBI-BDTT see figure 2 shown.

[0032]

[0033]

[0034] This embodiment also relates to the preparation method of polymer PEBI-BDTO and PEBI-BDTT, comprising the following steps:

[0035] (a) Synthesis of intermediate compound benzodithiophene bistin monomer

[0036] The structural formula of benzodithiophene ditin monomer is

[0037]

[0038] For its detailed preparation method, see the literature "Hwang, Y.J; Kim, F.S; Xin, H; Jenekhe, S.A; New Thienothiadiazole-Based Conjugated Copolymers for Electronics and Optoelectronics. ;FullereneDerivative-DopedZincOxideNanofilmastheCathodeofInvertedPolymerSolarCellswithLow-BandgapPolymer(PTB7-Th)forHighPerformance.Adv.Mater.2013,25,4766–477...

Embodiment 2

[0053] This example relates to the ultraviolet absorption spectrum and electrochemical properties of the polymers PEBI-BDTO and PEBI-BDTT of Example 1. Figure 5 The UV spectral properties of polymers in chloroform solution are given, and the λ of polymers PEBI-BDTO and PEBI-BDTT in chloroform solution UV-vis max abs Very close, 663 and 668nm respectively. Figure 6 The ultraviolet spectral properties of the polymer film state are given. Compared with the solution, the UV-vis of the film is red-shifted, λ max abs are 667nm and 676nm, red-shifted by 4nm and 8nm, respectively. Figure 7 The cyclic voltammetry curves of the compound polymers are 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 Am...

Embodiment 3

[0055] This example relates to the use of the polymers PEBI-BDTO and PEBI-BDTT of Example 1 as active layer materials in thin-film solar cells. Using polymers PEBI-BDTO and PEBI-BDTT as donor materials (D), fullerene (PC 71 BM) As the acceptor material (A), the photovoltaic performance of the material was tested using the bulk heterojunction structure. The test conversion efficiency data of polymer solar cell devices is shown in Table 2, and the I-V curve is shown in Figure 8 . The highest conversion efficiency of PNDFT-DTBT in the preliminary test is 4.59%, and the polymer has high open circuit voltage and fill factor.

[0056] Table 2

[0057]

[0058] In summary, the conjugated polymer of isoindigo derivatives in which butadiene is a spacer group involved in the present invention has good planar conjugation and good ultraviolet spectrum absorption. The material can be solution-processed and has a narrow energy band gap, good UV absorption and good thermal stability....

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Abstract

The invention provides a conjugated polymer shown as formula I or II in the specification. Specifically, R1 and R2 are both C8-C20 alkyl chain, and n is smaller than or equal to 100 and greater than or equal to 1. Compared with the prior art, the synthesis method disclosed by the invention is simple and effective, the cost is low, and the material can be subjected to solution processing, and can be used for organic thin film solar cell devices.

Description

technical field [0001] The invention relates to a solution-processable organic semiconductor material, in particular to a conjugated polymer of isoindigo derivatives with butadiene as a space isolation group and its preparation and application. Background technique [0002] Energy consumption in today's world is increasing, but non-renewable energy sources such as coal, oil, and natural gas are increasingly exhausted. Using solar energy is an effective way to solve energy problems faced by human society. [0003] Isindigo is widely used in photovoltaic materials due to its good electron-deficient properties, strong light absorption ability, and planar conjugation. Jo synthesized narrow-bandgap polymers PiITVT and PiI2T. Because the planarity of TVT is better than that of 2T, the photovoltaic performance of PiITVT is higher, and the PCE is as high as 7.09%. (References: Jung, E.H; Jo, W.H; π-Extendedlowbandgappolymerbasedonisoindigoandthienylvinyleneforhighperformancepolymer...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 吴建张清赵冬李胜夏
Owner SHANGHAI JIAO TONG UNIV
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