A kind of 2,2'-bis(benzothiophene)ethylene polymer and its preparation method and application

A technology of polymers and compounds, applied in the manufacture of semiconductor/solid-state devices, electrical components, circuits, etc., can solve the problem of less benzothiophene systems, achieve good air stability, and achieve simple and efficient synthesis routes

Active Publication Date: 2017-02-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a monomer of polymer semiconductor materials, the benzothiophene system is currently less studied

Method used

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  • A kind of 2,2'-bis(benzothiophene)ethylene polymer and its preparation method and application
  • A kind of 2,2'-bis(benzothiophene)ethylene polymer and its preparation method and application
  • A kind of 2,2'-bis(benzothiophene)ethylene polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1. Poly{2,5-di(2-octyldodecyl)-2,5-dihydro-1,4-dioxopyrrolo[3,4-c]pyrrole-3,6 -Diylthiophene-2,5-diyl-(E)-1,2-bis(benzo[b]thiophen-2-yl)ethylene-6,6'-diylthiophene-2,5-diyl }(P6BTE)(n=9)

[0061] The synthetic route of polymer P6BTE is as follows figure 1 As shown, the specific operation is as follows:

[0062] 1) Synthesis of 6-bromo[1]benzothiophene-2-carbaldehyde

[0063] Dissolve 6-bromo[1]benzothiophene (3.8g, 17.83mmol) in anhydrous THF (100mL), and slowly add fresh LDA (2.0M, 9.5mL, 19.0mmol) dropwise at 0°C, the reaction mixture After stirring at this temperature for 30 min, N-formylpiperidine (2.15 g, 19.0 mmol) was added dropwise. After warming to room temperature and reacting for 3 h, it was quenched with saturated ammonium chloride, extracted with dichloromethane, and dried over magnesium sulfate. The solution was spun off, and the mixture was subjected to silica gel column chromatography (eluent petroleum ether / ethyl acetate, v / v 10:1) to obtain...

Embodiment 2

[0088] Example 2, poly{2,5-di(2-octyldodecyl)-2,5-dihydro-1,4-dioxopyrrolo[3,4-c]pyrrole-3,6 -Diylthiophene-2,5-diyl-(E)-1,2-bis(benzo[b]thiophen-2-yl)ethylene-5,5'-diylthiophene-2,5-diyl }(compound P5BTE)

[0089] 1) Synthesis of 5-bromo[1]benzothiophene-2-carbaldehyde

[0090] 5-Bromo[1]benzothiophene (3.8g, 17.83mmol) was dissolved in anhydrous THF (100mL), and fresh LDA (2.0M, 9.5mL, 19.0mmol) was slowly added dropwise at 0°C, and the reaction mixture After stirring at this temperature for 30 min, N-formylpiperidine (2.15 g, 19.0 mmol) was added dropwise. After warming to room temperature and reacting for 3 h, it was quenched with saturated ammonium chloride, extracted with dichloromethane, and dried over magnesium sulfate. The solution was spun off, and the mixture was subjected to silica gel column chromatography (eluent petroleum ether / ethyl acetate, v / v 10:1) to obtain 3.22 g of a light yellow solid. Yield: 75%.

[0091] The structural characterization data are as ...

Embodiment 3

[0115] Spectral performance and field effect transistor performance of embodiment 3, P6BTE and P5BTE

[0116] 1) Spectral properties of P6BTE and P5BTE

[0117] image 3 UV-Vis absorption spectra of P6BTE chloroform solution and film.

[0118] Figure 4 UV-Vis absorption spectra of P5BTE chloroform solution and film.

[0119] Depend on image 3 It can be seen that the absorption peak position of the polymer P6BTE in chloroform is about 674 nanometers, and the film absorption peak positions are at 650 and 716 nanometers, and the optical bandgap calculated according to its film absorption sideband is 1.37 electron volts (the optical bandgap is based on the formula E. g =1240 / λ calculation, where E g is the optical band gap, and λ is the boundary value of the UV absorption curve).

[0120] Depend on Figure 4 It can be seen that the absorption peak position of the polymer P5BTE in chloroform is about 684 nanometers, and the absorption peak position of the film is at 676 n...

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Abstract

The invention provides a 2,2'-di(benzothiophene) ethylene polymer, a preparation method of the 2,2'-di(benzothiophene) ethylene polymer, and an application of the 2,2'-di(benzothiophene) ethylene polymer in a field effect transistor. A structural formula of the 2,2'-di(benzothiophene) ethylene polymer is shown in a formula I in the specification, wherein R is linear chain or branched chain alkyl of C1-C60. The invention also provides a preparation method of the polymer shown in the formula I. The 2,2'-di(benzothiophene) ethylene polymer provided by the invention is simple and efficient in synthetic route; and the maximum migration rate (u) of a PFET (polymer field-effect transistor) which is prepared by using a polymer semiconductor layer taking di(benzothiophene) ethylene as a copolymerization unit is 0.1cm<2>V<-1>s<-1>, and the switching ratio of the PFET is 10<5>-10<7>, so that the 2,2'-di(benzothiophene) ethylene polymer provided by the invention has a certain application prospect in the PFET.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a 2,2'-bis(benzothiophene)ethylene polymer, a preparation method thereof and its application in field effect transistors. Background technique [0002] Polymer field-effect transistors (PFETs), which use π-conjugated polymers as semiconductor materials, are active devices that control the conductivity of materials through electric fields, and have made great progress in recent years. Due to the excellent characteristics of polymer materials such as solution processing and good compatibility with plastic substrates, they are expected to become key components of circuits in next-generation flexible displays, such as electronic trademarks, smart cards, memories, electronic paper, sensors and Active matrix displays and other aspects have high application prospects and development value. [0003] The polymer semiconductor material plays a key role ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/30
Inventor 于贵黄剑耀刘晓彤毛祖攀张卫锋高冬
Owner INST OF CHEM CHINESE ACAD OF SCI
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