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Polymer semiconductor containing quinoid-donor-receptor unit, and preparation method and application thereof

An acceptor unit and polymer technology, applied in the field of polymer semiconductors and their preparation, can solve the problems of lowering the lowest occupied orbit, blurring boundaries, affecting the device performance of polymers, etc., achieving high yield, simple synthesis path, The effect of great development prospects and potential

Active Publication Date: 2021-12-31
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since they all contain an electron-withdrawing group with a carbonyl group at the end, this will significantly lower the lowest occupied orbital (LUMO energy level). The boundaries between electron acceptors, and even larger rings due to extended deformation, may form steric hindrance, affecting the device performance of the polymer

Method used

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  • Polymer semiconductor containing quinoid-donor-receptor unit, and preparation method and application thereof
  • Polymer semiconductor containing quinoid-donor-receptor unit, and preparation method and application thereof
  • Polymer semiconductor containing quinoid-donor-receptor unit, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] The synthesis path is as above

[0034] 1) Under inert gas conditions, (3Z, 6Z)-3,6-bis((5-bromothiophen-2-yl)methylene)piperazine-2,5-dione (1.6mmol, 1eq) , potassium carbonate (8.0mmol, 5eq), alkyl bromide (6.4mmol, 4eq) and N,N-dimethylformamide (15mL) were added to the reaction flask, heated to 90-110°C, reacted for 2 hours, and cooled to After room temperature, the reaction mixture was suction-filtered, and the filtrate was concentrated by rotary evaporation under reduced pressure, and subjected to silica gel column chromatography (hexane / dichloromethane ratio of 9:1 to 3:1), spin-dried and then used anhydrous Ethanol was recrystallized to obtain the desired compound 1 as an orange solid;

[0035] 2) Under inert gas conditions, compound 1 (600mg, 0.53mmol, 1eq) was dissolved in dry tetrahydrofuran (40mL) solution, cooled to -78°C, and n-butyllithium (0.83mL, 1.6M, 2.5 eq), after stirring the reaction for 1-2 hours, trimethyltin chloride (1.43mL, 1M, 2...

Embodiment 2

[0039] The synthesis route of this example is the same as that of Example 1, the difference is that the raw materials for preparing Compound 1 are different, and the compound 1 synthesized has a structural formula of The structural formula of compound 3 is

Embodiment 3

[0041] The synthesis route of this example is the same as that of Example 1, the difference is that the raw materials for preparing Compound 1 are different, and the compound 1 synthesized has a structural formula of The structural formula of compound 3 is

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Abstract

The invention discloses a polymer semiconductor containing a quinoid-donor-receptor unit, and a preparation method and application thereof. The synthesis method comprises the following steps: mixing (3Z, 6Z)-3, 6-bis((5-bromothiophen-2-yl)methylene)piperazine-2, 5-dione, potassium carbonate and alkyl bromide or alkyl iodide in N, N-dimethylformamide, reacting under inert gas, cooling, performing suction filtration, performing evaporative concentration on the obtained filtrate, performing silica gel column chromatography, recrystallizing with absolute ethyl alcohol to obtain a product, dissolving the product in a dry tetrahydrofuran solution, cooling, dropwise adding n-butyllithium, stirring for reaction, adding trimethyltin chloride, slowly raising the temperature to room temperature, stirring, quenching with water for reaction, extracting with dichloromethane, drying, filtering and spin-drying, and recrystallizing to obtain an oily product M; and carrying out Stille coupling polymerization reaction by taking the product M as a raw material to prepare the polymer. The polymer disclosed by the invention has the characteristics of high carrier mobility, simplicity in synthesis and relatively high yield, and has great development prospects and potential in the field of organic photoelectricity.

Description

technical field [0001] The invention relates to a semiconductor polymer, in particular to a polymer semiconductor whose main chain contains quinone-donor-acceptor units and its preparation method and application. Background technique [0002] Semiconducting polymers have attracted much attention due to their broad applications in organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and other electronic devices. How to modify the molecular structure to tune the energy levels of frontier orbitals and achieve high carrier mobility is one of the most fundamental issues in semiconducting polymers. At present, strategies to enhance carrier mobility by effectively controlling carrier hopping between chains and transport efficiency within chains have been proposed, such as rational design of novel structural units, side chain engineering, and optimization of active layer processing and device structure. . Among these attempts, the frontier orbital hybridization ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/42
CPCC08G61/126C08G61/123C08G2261/124C08G2261/3223C08G2261/3221C08G2261/3246C08G2261/414C08G2261/91C08G2261/92H10K30/00Y02E10/549
Inventor 刘迅成刘成梁欢欢
Owner GUIZHOU UNIV
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