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Polymer based on fluorodithiophene ethylene derivatives and application thereof in organic field-effect transistor

A technology of polymers and transistors, applied in the fields of organic chemistry, electric solid-state devices, semiconductor devices, etc., can solve problems such as unsatisfactory performance, and achieve a simple and easy synthesis route, a wide ultraviolet-visible light absorption spectrum, and good commercial application prospects. Effect

Active Publication Date: 2018-12-11
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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  • Polymer based on fluorodithiophene ethylene derivatives and application thereof in organic field-effect transistor
  • Polymer based on fluorodithiophene ethylene derivatives and application thereof in organic field-effect transistor
  • Polymer based on fluorodithiophene ethylene derivatives and application thereof in organic field-effect transistor

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 fluorodithiophene ethylene derivatives and application thereof in an organic field-effect transistor. The structural formula of the polymer based on fluorodithiophene ethylene derivatives is shown as formula I. The polymer disclosed by the invention is simple and feasible in synthetic process, few in synthetic steps, high in yield and suitable for large-scale synthesis. Migration rate and switching ratio of the organic field-effect transistor prepared from the polymer based on fluorodithiophene ethylene derivatives are both higher; the maximal migration rate is 0.37cm<2>V<-1>s<-1>; the switching ratio is above 10<5>. The polymer disclosed by the invention has an excellent application prospect in the organic field-effect transistor. The formula I is shown in the description.

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 Applications(China)
IPC IPC(8): C08G61/12C07D409/14C07D519/00H01L51/05H01L51/30
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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