Polymers based on fluorodithiophene vinyl derivatives and their applications in organic field effect transistors

A technology for polymers and transistors, applied in the fields of organic chemistry, electric solid devices, semiconductor devices, etc., can solve problems such as unsatisfactory performance, and achieve the effect of simple and easy synthesis route, excellent film formation, and excellent thermal stability.

Active Publication Date: 2020-09-29
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the performance of current field effect transistor devices cannot meet the needs of practical applications, so it is still very important to continue to develop new polymer materials. At the same time, it also provides opportunities for us to develop research results with independent intellectual property rights and seize the commanding heights of science and technology

Method used

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  • Polymers based on fluorodithiophene vinyl derivatives and their applications in organic field effect transistors
  • Polymers based on fluorodithiophene vinyl derivatives and their applications in organic field effect transistors
  • Polymers based on fluorodithiophene vinyl derivatives and their applications in organic field effect transistors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1, synthesis of polymer FVTI-BT (R=2-decyl dodecyl in formula I, X=C, Ar=2,2-dithiophene) (its synthetic route is as follows figure 2 shown)

[0075] 1) Synthesis of trans-1,2-bis(3-fluorothienyl)ethylene 1

[0076] To a solution of thiophene-2-carboxylic acid (17.0 g, 132.7 mmol) in anhydrous tetrahydrofuran (300 ml) was cooled to -78°C and slowly added 2.5M n-butyllithium in n-hexane (120 ml, 300 Millimoles). After completion, the reaction system was stirred at -78° C. for 30 minutes under the protection of nitrogen. Then N-fluorobisbenzenesulfonamide (50.0 g, 158.6 mmol) was dissolved in 300 ml of tetrahydrofuran and added to the reaction solution. After stirring at a low temperature of -78°C for 3 hours, hydrochloric acid was added to terminate the reaction, extracted with dichloromethane and washed with water several times, suspended in the solvent to obtain an intermediate product, and the amount of the intermediate product was accumulated by repeat...

Embodiment 2

[0103] Example 2, synthesis of polymer FVTI-BTF (R=2-decyl dodecyl in formula I, X=C, Ar=3,3-difluoro-2,2-dithiophene) (the synthesis route is as follows figure 2 shown)

[0104] The synthesis of compound 5 was carried out with reference to Example 1.

[0105] Compound 5 (265.5 mg, 0.20 mmol) and trimethyltin compound 8 (105.6 mg, 0.20 mmol), tris(dibenzylideneacetone) dipalladium (6.0 mg), tris(o-tolyl)phosphine ( 16.0 mg) and chlorobenzene (20 ml) were added into the reaction flask, and after deoxygenation at a low temperature of -78°C in nitrogen, the reaction was heated to 120°C under nitrogen protection for 15 minutes. After cooling, 200 ml of methanol / 6M HCl mixture (volume ratio 20:1) was added, stirred at room temperature for 2 hours, and filtered. The resulting solid was purified using a Soxhlet extractor. The extraction solvents were methanol, acetone, and n-hexane in sequence for 12 hours each, and then extracted with o-dichlorobenzene to obtain 258 mg of the ta...

Embodiment 3

[0109] Example 3, polymer FVTI-TVT synthesis (R=2-decyl dodecyl in formula I, X=C, Ar=trans-1,2-thienylethylene) (the synthesis route is as follows figure 2 shown)

[0110] The synthesis of compound 5 was carried out with reference to Example 1.

[0111] Compound 5 (200..0 mg 0.15 mmol) and trimethyltin compound 9 (77.7 mg, 0.15 mmol), tris(dibenzylideneacetone) dipalladium (6.0 mg), tris(o-tolyl) Phosphine (16.0 mg) and chlorobenzene (10 ml) were added to the reaction flask, and after deoxygenation at a low temperature of -78°C in nitrogen, the reaction was heated to 120°C under nitrogen protection for 15 minutes. After cooling, 200 ml of methanol / 6M HCl mixture (volume ratio 20:1) was added, stirred at room temperature for 2 hours, and filtered. The resulting solid was purified using a Soxhlet extractor. The extraction solvents were methanol, acetone, and n-hexane in sequence for 12 hours each, and then extracted with o-dichlorobenzene to obtain 196 mg of the target poly...

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Abstract

The invention discloses a polymer based on fluorinated dithienylethylene derivatives and its application in organic field effect transistors. The structural formula of the polymer based on fluorinated dithienylethylene derivatives is shown in formula I. The synthesis route of the present invention is simple and easy, has few synthesis steps, high yield and is suitable for large-scale synthesis. The mobility and switching ratio of the field effect transistor prepared by using the polymer based on the novel fluorodithiopheneethylene derivative of the present invention as the organic semiconductor layer are relatively high, and the mobility is up to 0.37cm 2 V ‑1 the s ‑1 , the on-off ratios are greater than 10 5 . The polymer of the invention has a good application prospect in organic field effect devices.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, in particular to polymers based on fluorinated dithienylethylene derivatives and their application in organic field effect transistors. Background technique [0002] Organic field-effect transistors (OFETs) are an important branch of organic electronics. Since its birth, it has received extensive attention from the global scientific and academic circles and has become one of the hot spots in the field of organic electronics research. . Due to its low cost, flexibility, and good compatibility with plastic substrates, organic field effect transistors are widely used in e-books, organic radio frequency tags, smart cards, integrated circuits, storage and sensor devices, and flexible display drive devices. Applications. In the next few decades, the development of science and technology, economic development, the direction of social progress, and the way of life of human being...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C07D519/00C08G61/12H01L51/05H01L51/30
CPCC07D409/14C07D519/00C08G61/122C08G61/124C08G61/126C08G2261/228C08G2261/3223C08G2261/124C08G2261/3241C08G2261/3327C08G2261/344C08G2261/354H10K85/151H10K85/113H10K10/46
Inventor 于贵周彦凯張世颖张卫锋王丽萍
Owner INST OF CHEM CHINESE ACAD OF SCI
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