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Trifluoromethyl-containing conjugated polymer, and preparation method and applications thereof

A technology of polymers and compounds, applied in the manufacture of semiconductor/solid-state devices, electrical components, circuits, etc., can solve the problems that are not enough to meet the structure-activity relationship and research of N-type semiconductor materials, achieve excellent thermal stability and fewer synthesis steps , The effect of simple synthetic route

Active Publication Date: 2019-06-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods are not enough for the development of N-type semiconductor materials and the research on the structure-activity relationship.

Method used

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  • Trifluoromethyl-containing conjugated polymer, and preparation method and applications thereof
  • Trifluoromethyl-containing conjugated polymer, and preparation method and applications thereof
  • Trifluoromethyl-containing conjugated polymer, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1, polymer PAIID-TFBVB-C1 synthesis (its synthetic route is as figure 2 shown)

[0073] 1) Synthesis of 2-(trifluoromethyl)-4-bromo-benzaldehyde (2)

[0074] 1,4-Dibromo-2-(trifluoromethyl)benzene (5.00 g, 16.45 mmol) and anhydrous tetrahydrofuran (120 ml) were successively added to a dry two-neck flask protected by argon. After the reaction system was cooled to -78°C, a 2.5M n-butyllithium solution in n-hexane (17.77 mmol, 7.11 mL) was slowly added dropwise. After the dropwise addition, continue stirring at -78°C for 10-20 minutes, then add N-formylpiperidine (2.79 g, 24.66 mmol) in one go, keep the reaction system at -78°C and stir for 30 minutes, Warm to room temperature slowly and stir the reaction overnight. The reaction was stopped, and the reaction solution was extracted with dichloromethane, dried over sodium sulfate and purified by column chromatography to obtain 3.50 g of the target product. Yield: 84%.

[0075] The structural characterization...

Embodiment 2

[0093] Embodiment 2, polymer PAIID-TFBVB-C3 synthesis (its synthetic route is as figure 2 shown)

[0094] Compound 5 (R=4-decyltetradecyl, 109.53 mg, 0.10 mmol) and compound 4 (56.82 mg, 0.10 mmol), tris(dibenzylideneacetone) dipalladium (4.50 mg), tris (o-Tolyl)phosphine (12.30 mg), chlorobenzene (5.0 mL), water (1.5 mL), potassium carbonate (138.21 mg, 1.0 mmol), and a catalytic amount of methyltrioctylammonium chloride were added under argon In a protected Schlenk bottle, the reaction system was refrigerated and deoxygenated at -78°C for 30 minutes, then stirred and reacted at 85°C for 72 hours, and phenylboronic acid and bromobenzene were successively added to the reaction system for capping. Stop the reaction and cool to room temperature, pour the reaction system into methanol and stir for 3 hours, then filter. The obtained product was purified with a Soxhlet extractor, and the solvents used were methanol, acetone, and n-hexane for 12 hours respectively. Finally, 133....

Embodiment 3

[0099] Spectral properties of embodiment 3, polymer PAIID-TFBVB-C1 and PAIID-TFBVB-C3

[0100] image 3 and Figure 4 The UV absorption spectrum of the polymer PAIID-TFBVB-C1 and PAIID-TFBVB-C3 chloroform solutions and films prepared in Examples 1 and 2.

[0101] Depend on image 3 It can be seen that this type of polymer exhibits strong double absorption bands in the ultraviolet region. while contrast image 3 , 4 It can be seen that the ultraviolet spectra of PAIID-TFBVB-C1 and PAIID-TFBVB-C3 do not change significantly from the solution to the film state, indicating that there is a strong interaction between the molecules in the solution state. In addition, the results also show that changing the alkyl side chain has little effect on the absorption spectrum.

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Abstract

The invention discloses a trifluoromethyl-containing conjugated polymer, and a preparation method and applications thereof. The trifluoromethyl-containing conjugated polymer is represented by formulaI. The synthesis route is simple and convenient; synthesis steps are few; yield is high; the preparation method is suitable for large scale preparation. Field effect transistors prepared taking the trifluoromethyl-containing conjugated polymer as organic semiconductor layers are relatively high in mobility and on / off ratio; the mobility is 0.11cm<2>V<-1>s<-1>, and the on-off ratio is larger than 105. It is shown by research results that the trifluoromethyl-containing conjugated polymer is an excellent electron transport material, and is promising in application prospect in the field of organicfield effect.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a trifluoromethyl-containing conjugated polymer and a preparation method and application thereof. Background technique [0002] Organic field-effect transistors (OFETs) are active electronic devices based on organic semiconductor materials. It is an important branch of organic electronics. It has attracted widespread attention and has become one of the research hotspots in organic electronics. Organic field-effect transistors have a very wide range of potential applications, and can be used to prepare e-books, organic radio frequency tags, smart cards, integrated circuits, storage and sensor devices, and flexible display drive devices. The realization of the wide application of organic field effect transistors will definitely have a significant impact on global technology and economy, human life style and social progress. [0003] An organic ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/05H01L51/30
Inventor 于贵魏聪源张卫锋
Owner INST OF CHEM CHINESE ACAD OF SCI
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