A kind of naphthalimide-fluorinated dithienylethylene conjugated polymer and its preparation method and application

A technology of fluorinated dithiophene ethylene and conjugated polymers, which is applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve problems such as poor device stability, achieve low frontier orbital energy levels, and reduce reaction yields. The effect of high rate and high polymer molecular weight

Active Publication Date: 2019-08-02
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And due to the energy level structure, most polymer materials with high electron mobility are susceptible to oxygen and water vapor in the air, showing poor device stability.

Method used

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  • A kind of naphthalimide-fluorinated dithienylethylene conjugated polymer and its preparation method and application
  • A kind of naphthalimide-fluorinated dithienylethylene conjugated polymer and its preparation method and application
  • A kind of naphthalimide-fluorinated dithienylethylene conjugated polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Poly{N,N-bis(2-octyldodecyl)-1,4,5,8-naphthalimide-2,6-(trans-1,2-bis(3-fluorothiophene-2 -base) vinyl)-2,5-diyl} is abbreviated as polymer PNFDTE1 below, that is, R in formula (I) 1 =R 2 = 2-octyldodecyl, the synthetic route is as figure 2 As shown, the preparation method is as follows:

[0049] Mix (trans)-1,2-bis(3-fluoro-5-trimethyltin-thiophen-2-yl)ethylene (110.8mg, 0.20mmol) and 2,6-dibromo-N,N-di (2-Octyldodecyl)-1,4,5,8-naphthalimide (197.0mg, 0.2mmol), tris(dibenzylideneacetone)dipalladium (9mg), tris(o-tolyl ) Phosphine (24.6mg) and chlorobenzene (5.0mL) were added to the reaction flask, three freeze-pump-thaw cycles were performed in argon to remove oxygen, and the reaction mixture was heated to 110°C under argon protection for 72h. After cooling, 200 mL of methanol / 6M hydrochloric acid 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 we...

Embodiment 2

[0055] Poly{N,N-bis(2-decyltetradecyl)-1,4,5,8-naphthalimide-2,6-(trans-1,2-bis(3-fluorothiophene-2 -base) ethylene) -2,5-diyl} hereinafter abbreviated as polymer PNFDTE2, that is, R in formula (I) 1 =R 2 =2-decyltetradecyl, the synthetic route is as figure 2 As shown, the preparation method is as follows:

[0056] Mix (trans)-1,2-bis(3-fluoro-5-trimethyltin-thiophen-2-yl)ethylene (110.8mg, 0.20mmol) and 2,6-dibromo-N,N-di (2-decyltetradecyl)-1,4,5,8-naphthalimide (219.5mg, 0.20mmol), tris(dibenzylideneacetone)dipalladium (9mg), tris(o-tolyl ) Phosphine (24.6mg) and chlorobenzene (5.0mL) were added to the reaction flask, three freeze-pump-thaw cycles were performed in argon to remove oxygen, and the reaction mixture was heated to 110°C under argon protection for 72h. After cooling, 200 mL of methanol / 6M hydrochloric acid 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 extrac...

Embodiment 3

[0062] Experiments on Spectral Properties of Polymer PNFDTE1 and Polymer PNFDTE2

[0063] image 3 and Figure 4 Be respectively the ultraviolet-visible absorption spectrogram of polymer PNFDTE1 and polymer PNFDTE2 chlorobenzene solution and film prepared by embodiment 1 and embodiment 2, from image 3 It can be seen that there are two absorption bands in this type of polymer, the secondary absorption band is a high energy band, and its absorption is at 300 to 470 nm, and the main absorption band is a low energy band, and its absorption is at 470 to 810 nm. Stronger low-energy band absorption indicates stronger intramolecular charge transfer within the polymer molecule. Depend on Figure 4 It can be seen that the absorption curve of the film has a certain degree of red shift compared with that of the solution, and the main absorption band is a low energy band, and the absorption is from 470 to 850 or 870 nanometers.

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Abstract

The invention discloses a naphthalimide-fluorinated dithienylethylene conjugated polymer, the structural formula of which is shown in formula (I), the polymer has a wide ultraviolet-visible absorption spectrum and good thermal stability, It has a lower frontier orbital energy level, which is beneficial to electron injection, and can prepare higher-performance field-effect transistors. The synthesis route of the naphthalimide-fluorinated dithienylethylene conjugated polymer of the present invention is simple and efficient, the molecular weight of the polymer is high, the post-treatment is simple, the reaction yield is high, and it is suitable for large-scale industrial synthesis. The organic field effect transistor prepared by using the naphthalimide-fluorinated dithiophene vinyl conjugated polymer semiconductor material of the present invention as a semiconductor layer has very high electron mobility

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a naphthalimide-fluorinated dithienylethylene conjugated polymer and a preparation method and application thereof. Background technique [0002] Polymer field effect transistor is an active device that uses polymer semiconductor material as the carrier transport layer and controls the conductivity of the material through the electric field. It has broad applications in the fields of smart cards, sensors, electronic radio frequency tags, large-screen displays and integrated circuits. Application prospect. Polymer semiconductor materials have the advantages of wide range of raw materials, easy synthesis, and simple purification process. At the same time, they have the controllability of physical and chemical properties, good flexibility and film-forming properties, and can be processed by solution methods. High-quality, flexible electronics offe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/05H01L51/30
CPCC08G61/122C08G61/126C08G2261/92C08G2261/124C08G2261/18C08G2261/3223C08G2261/3241C08G2261/146C08G2261/3422C08G2261/34C08G2261/514H10K85/111H10K85/113H10K85/151H10K10/46
Inventor 张卫锋陈智慧魏聪源于贵
Owner INST OF CHEM CHINESE ACAD OF SCI
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