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Naphthalimide thiophene cyanoethylene polymer as well as preparation method and application thereof

A polymer and compound technology, applied in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., can solve problems such as unsatisfactory stability, and achieve good thermal stability, broad application prospects, and high reaction yield.

Inactive Publication Date: 2017-09-08
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the stability of existing polymer semiconductor materials as semiconductor layer materials still cannot meet the actual application environment. Therefore, designing and synthesizing high-performance and stable semiconductor materials has become the primary task of researchers.

Method used

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  • Naphthalimide thiophene cyanoethylene polymer as well as preparation method and application thereof
  • Naphthalimide thiophene cyanoethylene polymer as well as preparation method and application thereof
  • Naphthalimide thiophene cyanoethylene polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthesis of embodiment 1, polymer PNCNTVT-8

[0042] 4,9-dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraketone ( 0.20mmol, 197.01mg) and cis-2,3-bis(5-(trimethyltin) thiophen-2-yl) acrylonitrile (0.20mmol, 108.60mg) shown in formula III, the palladium catalyst is three (diethylene Benzylacetone) dipalladium (6mg, 0.0065mmol), the ligand tris(o-tolyl)phosphine (16.2mg, 0.053mmol) and the organic solvent chlorobenzene (6.0mL) were added to the reaction flask and carried out three times under argon. The freeze-pump-thaw cycle was used to deoxygenate, and then the reaction mixture was heated to 110 °C under the protection of argon to carry out the Stille coupling reaction for 24 h. After cooling, 200 mL of methanol / 6M HCl mixture (v / v 20:1) was added, stirred at room temperature for 2 h, and filtered. The resulting solid was extracted with a Soxhlet extractor. The extraction solvents were methanol, acetone, and n-hexane in sequence,...

Embodiment 2

[0047] Embodiment 2, polymer PNCNTVT-10

[0048] 4,9-dibromo-2,7-bis(2-decyltetradecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraketone ( 0.20mmol, 219.46mg) and cis-2,3-bis(5-(trimethyltin)thiophen-2-yl)acrylonitrile (0.20mmol, 108.60mg) shown in formula III, three(dibenzylideneacetone ) Dipalladium (6mg, 0.0065mmol), tri(o-tolyl)phosphine (16.2mg, 0.053mmol) and chlorobenzene (6.0mL) were added to the reaction flask, and three freeze-pump-thaw cycles were carried out under argon After deoxygenation, the reaction mixture was heated to 110 °C under the protection of argon to perform Stille coupling reaction for 24 h. After cooling, 200 mL of methanol / 6M HCl mixture (v / v 20:1) was added, stirred at room temperature for 2 h, and filtered. The resulting solid was extracted with a Soxhlet extractor. The extraction solvents were methanol, acetone, and n-hexane in sequence, each for 24 hours, and finally extracted with chloroform to obtain 182.26 mg of the target polymer,...

Embodiment 3

[0053] Spectral performance test of embodiment 3, polymer PNCNTVT-8 and polymer PNCNTVT-10

[0054] image 3 and Figure 4 Be respectively the chloroform solution (concentration is 0.005mmol / L) of the polymer PNCNTVT-8 and polymer PNCNTVT-10 prepared by embodiment 1 and embodiment 2 and the ultraviolet-visible absorption spectrum figure of film, from image 3 It can be seen that there are two absorption bands in this type of polymer, the main absorption band is a high energy band, and its absorption is at 360 to 470 nm, and the secondary absorption band is a low energy band, and its absorption is at 480 to 750 nm. The strong low-energy band absorption indicates that there is a strong D-A interaction in the polymer molecule. Depend on Figure 4 It can be seen that the absorption curve of the film has a red shift to a certain extent compared with that of the solution.

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Abstract

The invention discloses a naphthalimide thiophene cyanoethylene polymer as well as a preparation method and application thereof. The polymer has a structural formula as shown in formula I; and the polymer has a strong interchain interaction, and has a rigid planar structure. The material has relatively high ultraviolet-visible absorption and high thermal stability, has relatively low energy level structure beneficial for injection of current carriers, and can be used for preparing bipolar organic field-effect transistors with relatively high performance; obtained devices have high hole mobility ([mu]h) and on-off ratio, wherein the hole mobility is up to 6.41*10<-3>cm<2>V<-1>s<-1>; the on-off ratio is 10<2>-10<3>; and the obtained devices have relatively high electron mobility ([mu]e) (the electron mobility is up to 4.82*10<-2>cm<2>V<-1>s<-1>), and have broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a naphthalene imide thiophene cyanoethylene polymer and a preparation method and application thereof. Background technique [0002] An organic field effect transistor is an active device that controls the current between the source and the drain through the voltage of the gate, and uses organic semiconductor materials as the carrier transport layer. High-performance organic field-effect transistors have broad application prospects. Their successful applications in smart cards, sensors, electronic radio frequency tags, large-screen displays and integrated circuits will certainly promote technological innovation in many fields such as information, energy, and life. It will have a profound impact on economic development and social progress. Compared with traditional inorganic materials, organic semiconductor materials have the following characteri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/05H01L51/30
CPCC08G61/122C08G61/126C08G2261/92C08G2261/334C08G2261/414C08G2261/514C08G2261/592C08G2261/3223C08G2261/3241C08G2261/124C08G2261/1412C08G2261/1428C08G2261/143H10K85/113H10K10/46
Inventor 于贵林祖樟刘晓彤张卫锋王丽萍
Owner INST OF CHEM CHINESE ACAD OF SCI
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