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A kind of quinone conjugated polymer and its preparation method and application

A technology of conjugated polymers and quinones, which is applied in the field of quinones conjugated polymers and its preparation, can solve the problems of not being able to obtain quinones polymers, complex preparation process, and lower molecular energy gap, etc. The effect of fast process, simple preparation method and high application value

Active Publication Date: 2020-09-01
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to obtain quinone structure polymers with higher conductivity, there are currently many related researches. For example, Adv.Sci, 2018, 5, 1800947 reported a method for synthesizing a polythiophene derivative. After the polymer is doped, When the temperature is nearly 100 degrees Celsius, the conductivity of the doped polymer is greatly improved; TW201841921 reported a quinone structure organic semiconductor substituted by dicyanomethylene materials, but the synthesis of such compounds is complicated, the final aromatic structure must be converted into a quinone structure by introducing dicyanomethylene capping, and the polymerization length of the molecule is limited. Through this synthesis process, the quinone structure cannot be obtained. polymer; WO9622317 reported a method for synthesizing polypyrrole and obtaining high conductivity by doping, and the polypyrrole monomer obtained by this method is linked by a C-C single bond, and the polymer can become a conductive polymer only after doping ; JP2017206649 reported an organic semiconductor material containing a quinone structure fragment, which proved that the quinone structure can greatly reduce the energy gap of the molecule and enhance its charge transfer performance
[0007] But so far, it is usually the case that the aromatic structure is oxidized to obtain a quinoid conjugated polymer, and the preparation process is complicated, and there is no report about a quinoid polymer linked by a C=C double bond.

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  • A kind of quinone conjugated polymer and its preparation method and application
  • A kind of quinone conjugated polymer and its preparation method and application
  • A kind of quinone conjugated polymer and its preparation method and application

Examples

Experimental program
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Embodiment 1

[0037] The preparation process of the quinone conjugated polymer described in this embodiment is as follows:

[0038]

[0039] Wherein, X is S or O.

[0040] Further, its specific preparation method is:

[0041] Phthalimide (IIa, 1 gram, 6.89mmol), Lawson's reagent (2.79 gram, 6.89mmol) and a magnetic stirrer are placed in a 500ml two-necked flask and a condenser tube is installed; Vacuum nitrogen filling operation, repeat this operation three times; Inject trichlorobenzene (200ml) in the flask under the protection of nitrogen; The solution is warmed up to reflux and stirred for 72 hours; The reaction solution is cooled to separate out the solid; Wash the solid with acetone three times; dry the solid obtained by suction filtration in a vacuum oven at 100°C for 10 hours; grind the solid with an agate mortar and extract it with a Soxhlet extractor for 48 hours, collect the solid in the extraction sleeve and dry it , the solvent used for extraction is toluene. Grind the dri...

Embodiment 2

[0043] The preparation process of the quinone conjugated polymer described in this embodiment is as follows:

[0044]

[0045] Wherein, X is S or O.

[0046] Further, its specific preparation method is:

[0047] Pyridine 2,3-diimide (IIb, 1 gram, 6.75mmol), the derivative (2.73 gram, 6.75mmol) of Lawson's reagent and the magnetic stirring bar are placed in the 500ml two-necked flask and a condenser is installed; Arrangement pipe is carried out the operation of evacuating and filling the flask with nitrogen, repeat this operation three times; inject trimethylbenzene (200ml) into the flask under the protection of nitrogen; the solution is warmed up to reflux and stirred for 72 hours; the reaction solution is cooled to separate out the solid; Collect the solid, wash the solid three times with 30ml of acetone; dry the solid obtained by suction filtration in a vacuum oven at 100°C for 10 hours; grind the solid with an agate mortar and then extract it with a Soxhlet extractor for ...

Embodiment 3

[0049] The preparation process of the quinone conjugated polymer described in this embodiment is as follows:

[0050]

[0051] Wherein, X is S or O.

[0052] Further, its specific preparation method is:

[0053] Ortho-pyrazine diimide (IIc, 1 gram, 6.71mmol), phosphorus tetrasulfide (2.71 gram, 6.71mmol) and magnetic stirring bar are placed in the 500ml two-necked flask and a condenser tube is installed; Carry out the operation of vacuumizing and charging nitrogen, repeat this operation three times; Inject diphenyl ether (200ml) in the flask under the protection of nitrogen; The solution is warmed up to reflux and stirred for 72 hours; The reaction solution is cooled to separate out the solid; The solid is collected by suction filtration, Wash the solid three times with 30ml of acetone; dry the solid obtained by suction filtration at 100°C for 10 hours in a vacuum oven; grind the solid with an agate mortar and extract it with a Soxhlet extractor for 48 hours, and collect t...

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Abstract

The invention relates to a quinoid conjugated polymer, a preparation method and application thereof. The quinoid conjugated polymer is a novel quinoid structure polymer connected by C=C double bonds and has good electrical conductivity. , the monomer used in the preparation of the quinoid conjugated polymer contains at least two carbonyl groups, the preparation method is simple, and the conductive properties can be exhibited without oxidation treatment or doping, the preparation process is fast and convenient, and can be applied to optoelectronic devices , has high application value.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, more specifically, to a quinone conjugated polymer and its preparation method and application. Background technique [0002] In recent decades, with the continuous development of new semiconductor devices and integrated circuit technology, research on semiconductor materials has become more and more in-depth. Among them, conductive polymers have become a research hotspot of semiconductor materials because they have the properties of ordinary polymers, can prepare foldable and curved devices, and have good film-forming properties. Conductive polymers are commonly used in electrical devices such as batteries, capacitors, electronic sensors, antistatic coatings, EMI protection, anti-corrosion coatings on metals, lithography, circuit boards, organic light-emitting diodes, solar cells, and field effect transistors. [0003] Most organic polymers are insulators or semiconductors, and som...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/12H10K85/10C08G61/124C08G2261/3241C08G2261/11C08G2261/18C08G2261/52C08G2261/91C08G2261/43C08G75/30
Inventor 李辰段若蒙刘志宏赵雁飞克劳斯·缪伦田禾魏文山
Owner DONGGUAN UNIV OF TECH
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