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Semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer as well as preparation method and application of semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer

A technology of diketopyrrolopyrrole and hemifluoroalkyl, which is used in semiconductor/solid-state device manufacturing, semiconductor devices, electrical components, etc.

Pending Publication Date: 2019-06-21
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the synthesis of small molecules and polymers containing semifluoroalkyl dovetail side chains substituted with DPP groups and their research in OTFTs have not been reported.

Method used

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  • Semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer as well as preparation method and application of semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer
  • Semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer as well as preparation method and application of semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer
  • Semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer as well as preparation method and application of semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Embodiment 1, copolymer shown in preparation formula I

[0129] In the Schlenk bottle of 50mL, add the compound shown in 0.186g (0.11mmol) monomeric formula M1 (m 1 = m 2 =9; n=2), 0.049g (0.11mmol) compound 5,5-bistrimethylsilyl-2,2'-bithiophene shown in monomer formula M2 and 4mL dehydrated chlorobenzene, the reaction system adopts liquid The nitrogen cooling cycle displaces the nitrogen three times. 2.22 mg (0.0024 mmol) of tris(dibenzylideneacetone) dipalladium, 3 mg (0.01 mmol) of tri-o-tolylphosphine were added. Stir under reflux at 115°C for 48 hours. 2ml of bromobenzene was added to react overnight to complete the capping of the polymer. After cooling to room temperature, the reaction mixture was poured into 200 mL of methanol solution containing 15 mL of hydrochloric acid to settle, and then suction filtered to collect a black solid. Then use a Soxhlet extractor to separate the pure product, the washing solvent is methanol (12 hours), n-hexane (12 hours), ...

Embodiment 2

[0131] Embodiment 2, copolymer shown in preparation formula I

[0132] In the Schlenk bottle of 50mL, add the compound shown in 0.186g (0.11mmol) monomeric formula M1 (m 1 = m 2 =9; n=2), 0.058g (0.11mmol) compound (3,3'-difluoro-[2,2'-dithiophene]-5,5'-diyl)bis represented by monomer formula M2 trimethyltin and 5mL of anhydrous chlorobenzene, and the reaction system was replaced with nitrogen three times by liquid nitrogen cooling cycle. 2.22 mg (0.0024 mmol) of tris(dibenzylideneacetone) dipalladium, 3 mg (0.01 mmol) of tri-o-tolylphosphine were added. Stir under reflux at 115°C for 48 hours. 2ml of bromobenzene was added to react overnight to complete the capping of the polymer. After cooling to room temperature, the reaction mixture was poured into 200 mL of methanol solution containing 15 mL of hydrochloric acid for settling, and the black solid was collected by suction filtration. Then use a Soxhlet extractor to separate the pure product, the washing solvent is meth...

Embodiment 3

[0135] Embodiment 3, copolymer shown in preparation formula I

[0136] In the Schlenk bottle of 50mL, add the compound shown in 0.186g (0.11mmol) monomeric formula M1 (m 1 = m 2 =9; n=2), 0.052g (0.11mmol) compound 2,5-bis(trimethyltin)-thienothiophene shown in monomer formula M2 and 5mL dehydrated chlorobenzene, the reaction system was cooled by liquid nitrogen circulation Nitrogen was replaced three times. 2.22 mg (0.0024 mmol) of tris(dibenzylideneacetone) dipalladium, 3 mg (0.01 mmol) of tri-o-tolylphosphine were added. Stir under reflux at 115°C for 48 hours. 2ml of bromobenzene was added to react overnight to complete the capping of the polymer. After cooling to room temperature, the reaction mixture was poured into 200 mL of methanol solution containing 15 mL of hydrochloric acid to settle, and then suction filtered to collect a black solid. Then use a Soxhlet extractor to separate the pure product, the washing solvent is methanol (12 hours), n-hexane (12 hours), c...

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Abstract

The invention discloses a semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer, and particularly relates to the semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer as well as a preparation method and an application of the semi-fluoroalkyl containing side chain substituted pyrrolo pyrroledione polymer. The provided synthesis route has the advantages of simplicity, high efficiency, low synthesis cost, good universality and repeatability, and the like, and can be popularized and applied to the synthesis of pyrrolo pyrroledione polymers of other various substituent groups. The migration rate of OTFTs (Organic Thin Film Transistors) prepared by taking the polymer PC10DPPBT as an organic semiconductor layer is as high as 0.0082 cm<2> / V.s, and the excellent application prospect of the polymer material in the OTFTs is fully shown.

Description

technical field [0001] The invention relates to a diketopyrrolopyrrole polymer substituted with a semifluoroalkyl side chain, in particular to a diketopyrrolopyrrole polymer substituted with a semifluoroalkyl dovetail side chain, a preparation method and application thereof. Background technique [0002] Since the invention of the conductive polymer polyacetylene, scientists have begun to develop organic semiconductor materials to replace the widely used inorganic semiconductor materials. Organic field-effect transistors with organic semiconductor materials as active layers have also received attention. With the unremitting efforts of scientists and the rapid development of material science and processing technology, the performance of organic field effect transistors has been greatly improved and improved, and will soon be used in people's production and life. It has strong competitive potential and broad application prospects in terms of low-cost preparation and high flex...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30
Inventor 吴倜刘省珍蒲嘉陵张伟民
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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