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Polymer semiconductor containing bipyridine diazole derivative receptor and preparation method and application thereof

A pyridinediazole and polymer technology, which is applied in the field of polymer semiconductors containing bispyridinediazole derivative acceptors and its preparation, to achieve high electron mobility, short and efficient synthesis routes, and enhanced π-π interaction effects

Active Publication Date: 2018-01-12
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, electron-transporting pyridinediazole derivative-based polymer semiconductor materials have not been reported

Method used

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  • Polymer semiconductor containing bipyridine diazole derivative receptor and preparation method and application thereof
  • Polymer semiconductor containing bipyridine diazole derivative receptor and preparation method and application thereof
  • Polymer semiconductor containing bipyridine diazole derivative receptor and preparation method and application thereof

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Effect test

specific Embodiment 1

[0056] A polymer semiconductor containing a bispyridinediazole derivative acceptor of the present invention, specifically a polymer semiconductor material with a chemical structure of PBPTV, and its synthetic route is as follows:

[0057]

[0058] (1) Synthesis of an intermediate whose chemical structural formula is a: under nitrogen protection, tributyl-[4-(2-decyltetradecyl)thiophen-2-yl]alkyltin (5.8g , 8.2mmol), 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine (2.0g, 6.8mmol), bis(triphenylphosphine)palladium dichloride (0.24g, 0.34mmol) catalyst, 70mL toluene solvent. After reflux for 4 hours, cool to room temperature. Using dichloromethane for extraction, the organic phase was dried with magnesium sulfate, and the solvent was spin-dried to obtain a crude product. Then use silica gel column purification to obtain the target product 7-bromo-4-(4-(2-decyltetradecyl)thiophen-2-yl)-[1,2,5]thiazole[3,4-c] Pyridine, yield = 85%.

[0059] The structural characterization data...

specific Embodiment 2

[0075] A polymer semiconductor containing a bispyridinediazole derivative acceptor of the present invention, specifically a polymer semiconductor material with a chemical structure of PBPT2V, its synthetic route is as follows:

[0076]

[0077] (1) Synthesis of an intermediate whose chemical structural formula is a: Synthesize with reference to the synthetic method of the above-mentioned Example 1.

[0078] (2) Synthesis of an intermediate whose chemical structural formula is c: under nitrogen protection, add compound b[(E)-1,2-bis(tributyltin-based)ethylene] (0.56g, 0.92mmol) and compound a (1.75g, 2.76mmol), tetrakis(triphenylphosphine) palladium catalyst (0.053g, 0.046mmol) and toluene solvent. After reflux for 24 hours, cool to room temperature. Extract with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, and spin the solvent to obtain a crude product. The target product (E)-1,2-bis(4-4-(2-decyltetradecyl)thiophen-2-yl)-[1,2,5]thiazo[3, 4-c]p...

Embodiment 1 and 2

[0091] The measurement of the spectroscopic property of gained polymer PBPTV and PBPT2V and thin film field effect transistor property prepared by above-mentioned embodiment 1 and 2:

[0092] (1) Absorption spectral properties of polymers PBPTV and PBPT2V

[0093] figure 1 UV-visible-near-infrared absorption spectra of polymer PBPTV in chlorobenzene solution and thin film on quartz plate. Depend on figure 1 It can be seen that both the polymer PBPTV solution and the film exhibit a wide absorption range, and the maximum absorption sideband value of the film is about 865nm, and the corresponding optical band gap is 1.43eV (the optical band gap is calculated according to the formula E g =1240 / λ calculation, where E g is the optical bandgap, and λ is the maximum absorption sideband value of film absorption).

[0094] figure 2 UV-visible-near-infrared absorption spectra of polymer PBPT2V in chlorobenzene solution and thin film on quartz wafer. Depend on figure 2 It can be ...

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Abstract

The invention belongs to the field of polymer semiconductor materials, and discloses a polymer semiconductor containing a bipyridine diazole derivative receptor and a preparation method and application thereof. A structure of the polymer semiconductor is shown in a formula (I), and the preparation method comprises the following steps: (1) reacting 2-tributyltin-4-alkylthiophene with a dibromobenzimidazole derivative to prepare an intermediate a; (2) reacting the compound a with a bis-butyltin b to obtain a compound c; (3) performing a reaction on the compound c and N-bromosuccinimide to obtainM1; and (4) performing a palladium-catalyzed coupling reaction on the M1 and (E)-bis1,2-(tri-n-butyltin)ethylene to obtain the final product. According to the invention, the synthetic route is simpleand high-efficiency, the raw materials are easy to obtain, the costs are low, the universality is high and the repeatability is good, and a field effect transistor prepared by using the polymer semiconductor as an active layer obtains outstanding bipolar transmission characteristics, and has wide market prospects.

Description

technical field [0001] The invention belongs to the field of polymer semiconductor materials, and relates to a polymer semiconductor containing a bispyridinediazole derivative acceptor, a preparation method and application thereof. Background technique [0002] Bipolar polymer semiconductor materials can simplify the preparation process of bipolar logic complementary circuits and reduce construction costs, but such materials face challenges such as low mobility, unbalanced carrier transport, and scarcity of building units. At present, high-mobility bipolar polymer semiconductor materials are mainly constructed from diketopyrrolopyrrole and isoindigo derivative units, and there are only a few polymer semiconductor materials with hole and electron mobilities that can exceed 4.0 cm at the same time. 2 / V s (J. Am. Chem. Soc., 2013, 135, 9540; Chem. Mater., 2014, 26, 6963; Adv. Mater., 2015, 27, 4963). Therefore, exploring new design strategies and finding new building blocks i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/05H01L51/30
Inventor 陈华杰朱春光郑丽萍
Owner XIANGTAN UNIV
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