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Mono-alkyl-substituted H bond bioxindol-containing monomer, preparation of its copolymer and application thereof

A mono-alkyl, copolymer technology, applied in the field of organic semiconductor materials, can solve the problems of obvious phase separation, unfavorable formation of H bonds, low PCE, etc., and achieve the effect of simple and effective synthesis method, good UV absorption, and narrow molecular weight distribution

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

[0004] Since the introduction of H bonds means that the alkyl chain of the substituent is reduced, the solubility of the donor material in common organic solvents is poor, which brings difficulties to device processing. If the solubility is too poor, it may cause very obvious phase separation, and It is not conducive to the formation of H bonds, and the microscopic morphology will be very poor, resulting in a relatively low PCE

Method used

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  • Mono-alkyl-substituted H bond bioxindol-containing monomer, preparation of its copolymer and application thereof
  • Mono-alkyl-substituted H bond bioxindol-containing monomer, preparation of its copolymer and application thereof
  • Mono-alkyl-substituted H bond bioxindol-containing monomer, preparation of its copolymer and application thereof

Examples

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Effect test

Embodiment 1

[0039] This embodiment provides a monoalkyl-substituted H bond-containing isoindigo monomer IIDH and its benzodithiophene bistin copolymer (PIIDH-BDTO and PIIDH-BDTT), the structural formula of which is shown in Table 1 (wherein, 100>n>1), the synthetic route of its monomer IIDH can be found in figure 1 , the synthesis of polymers PIIDH-BDTO and PIIDH-BDTT see figure 2 shown.

[0040] Table 1

[0041]

[0042]

[0043] This embodiment also relates to the preparation method of polymer PIIDH-BDTO and PIIDH-BDTT, comprising the following steps:

[0044] (a) Synthesis of intermediate compound benzodithiophene bistin derivatives

[0045] The synthetic structural formula of intermediate compound benzodithiophene bistin derivative is

[0046] 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-DopedZincOxideNanofilma...

Embodiment 2

[0065] This example relates to the H NMR spectrum and C NMR spectrum of the monoalkyl-substituted H-bond-containing isoindigo monomer in Example 1, as well as the UV absorption spectrum and electrochemical properties of the polymers PIIDH-BDTO and PIIDH-BDTT. image 3 with Figure 4 The H NMR and C NMR spectra of compound 1 are given respectively, Figure 5 with Image 6 The H NMR and C NMR spectra of monomeric IIDH are given. Figure 7 The UV spectra of the polymers in chloroform solution are given. The maximum absorption peaks of these two polymers in chloroform solution are very close, at 630 and 625 nm, respectively. PIIDH-BDTO has a little red shift, but not obvious. Figure 8 The ultraviolet absorption spectrum of the polymer solid film is given. The UV-Vis absorption of the solid film is obviously red-shifted, and the maximum absorption peaks are 669 and 634nm, respectively, which are 39 and 9nm red-shifted compared with the chloroform solution. The onset absorption ...

Embodiment 3

[0067] This example relates to the use of the polymers PIIDH-BDTO and PIIDH-BDTT of Example 1 as active layer materials in thin-film solar cells. Using polymers PIIDH-BDTO and PIIDH-BDTT as donor materials (D), fullerene (PC7 1 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 10 . The highest conversion efficiency of PIIDH-BDTT in the preliminary test is 1.73%.

[0068] Table 2

[0069] polymer

[0070] In summary, the monoalkyl substituted H-bond-containing isoindigo and benzodithiophene copolymer of the present invention has a rigid planar Π conjugated system, good ultraviolet absorption, and the material can be processed by solution, and has a good performance in photovoltaic devices. application prospects.

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Abstract

The invention discloses a mono-alkyl-substituted H bond bioxindol-containing monomer, a preparation of its copolymer and an application thereof. The monomer IIDH has a structural formula shown as a formula I in a specification, wherein R1 is C8-C20 alkyl chains. Under condition that Pd(dba)3 is taken as a catalyst, P(o-tol)3 is taken as a ligand, anhydrous toluene is taken as a solvent, the monomer IIDH and benzodithiophene double-tin are polymerized, and a copolymer can be obtained through extraction by soxhlet. The disclosed synthetic method is simple and effective, the distribution of the obtained target polymer molecular weight is narrow; the mono-alkyl-substituted H bond bioxindol and benzodithiophene-containing copolymer has a II conjugated system of a rigid plane, and has good ultraviolet absorption function, the material can be processed with a solution, and the mono-alkyl-substituted H bond bioxindol-containing monomer has good application prospect in a photovoltaic device.

Description

technical field [0001] The invention relates to a solution-processable organic semiconductor material, in particular to a monoalkyl-substituted H-bond-containing isoindigo monomer IIDH and its benzodithiophene bistin copolymer, as well as its preparation and use. 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] In recent years, due to the advantages of light weight and solution processing, organic solar cells have attracted great research interest of researchers. The bulk heterojunction OPV active layer is composed of donor materials and acceptor materials (fullerene derivatives) to form an interpenetrating network structure. The donor material absorbs photons to generate excitons, and the excitons move to the interface and dissociate to generate charge...

Claims

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Application Information

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IPC IPC(8): C07D209/34C08G61/12H01L51/46
CPCC07D209/34C08G61/126H10K85/151H10K30/00Y02E10/549
Inventor 吴建黄灝周祥梅张清张爱迪刘影
Owner SHANGHAI JIAO TONG UNIV
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