A kind of di(benzothiophene)ethylene polymer and its preparation method and application

A technology of benzothiophene and polymers, applied in the application field of diethylene polymers and its preparation, and field effect transistors, can solve the problems of less research on materials, achieve good stability, good application prospects, and simple synthetic routes Efficient effect

Active Publication Date: 2017-02-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few researches on polymer semiconductor materials of benzothiophene system

Method used

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  • A kind of di(benzothiophene)ethylene polymer and its preparation method and application
  • A kind of di(benzothiophene)ethylene polymer and its preparation method and application
  • A kind of di(benzothiophene)ethylene polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Synthesis of (n=12, P6TBE-8-10)

[0062] 1) Synthesis of (E)-1,2-bis([1]benzothiophen-6-yl)ethylene

[0063] Titanium tetrachloride (1.6mL, 13.9mmol, 1.2eq) was added dropwise to anhydrous tetrahydrofuran (50mL) cooled in an ice-salt bath under a nitrogen atmosphere, and after stirring for 30 minutes, Zn powder (1.9g) was added, and the reaction mixture was Heat and boil for 1h. After cooling down in an ice bath, benzothiophene-6-carbaldehyde (1.88 g, 11.6 mmol) was added dropwise, stirred for 15 min, and then the reaction solution was heated to boiling for 4 h. After cooling to room temperature, the reaction was quenched with 100 mL of ice water, filtered, and the filter cake was washed with ethanol and then recrystallized with toluene to obtain 1.21 g of light yellow crystals. Yield: 71.3%. Structural characterization data are as follows:

[0064] Mass Spectrum: [MS(EI)]m / z:292(M + ), [HR-EI] 292.0380.

[0065] H NMR and C NMR: 1 H NMR (300MHz, CDCl ...

Embodiment 2

[0077] Embodiment 2, Synthesis of (n=17, P5TBE-8-10)

[0078] 1) Synthesis of (E)-1,2-bis([1]benzothiophen-5-yl)ethylene

[0079] Titanium tetrachloride (3.2mL, 27.8mmol, 1.5eq) was added dropwise to anhydrous tetrahydrofuran (50mL) cooled in an ice-salt bath under a nitrogen atmosphere, and after stirring for 30 minutes, Zn powder (3.4g, 2.8eq) was added , The reaction mixture was heated and boiled for 1h. After cooling down in an ice bath, benzothiophene-5-carbaldehyde (3.00 g, 18.5 mmol) was added dropwise, stirred for 20 min, and then the reaction solution was heated to boiling for 6 h. After cooling to room temperature, the reaction was quenched with 100 mL of ice water, filtered, and the filter cake was washed with ethanol and then recrystallized with toluene to obtain 1.87 g of white crystals. Yield: 69%. Structural characterization data are as follows:

[0080] Mass spectrum: [HR-EI] 292.0380.

[0081] H NMR and C NMR: 7.942-7.939 (m, 2H), 7.868 (d, 2H, J = 8.1Hz...

Embodiment 3

[0092] Embodiment 3, Synthesis of (n=21, P6TBE-3CH2)

[0093] 1) Synthesis of compound a

[0094] Into a 500mL single-necked bottle, add 8.4g 3,6-bis(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione in sequence (refer to literature Li, Yuning; Sonar, Prashant; Singh, Samarendra P.; Soh, Mui Siang; VanMeurs, Martin; Tan, Jozel, J. Am. Chem. Soc., 2011, 133, 2198–2204 Synthesis), anhydrous potassium carbonate 9.0 g and 90 mL of DMF. Under the protection of nitrogen, after stirring at 100°C for 60min, 30.7g of 1-iodo-4-decyltetradecane and 40mg of 18-crown-6 were added, and then stirring was continued at 120°C for 24h. Extract with chloroform and dry over anhydrous magnesium sulfate. The crude product was sonicated with methanol to wash away a small amount of large polar impurities, and then sonicated with a small amount of n-hexane to remove excess iodide. Afterwards, the residue was separated by silica gel column chromatography (dichloromethane:petroleum ether=0-0.5) to obtain ...

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PUM

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Abstract

The invention discloses bis(benzothiophene) ethylene polymers and a preparation method and application thereof. The polymers have a structural formula I or I' shown in the specification, wherein R is C1-C60 straight-chain or branched-chain alkyl. The invention further discloses a preparation method of the polymers. The synthesis route of the method is simple and effective; the raw materials are commercialized cheap products, thereby ensuring low synthesis cost; the synthesis method has universality and can be popularized in the synthesis of polymers based on bis(benzothiophene) ethylene compounds through substitution with various substituent groups. The migration rate and switch ratio of PFET prepared by using the polymers based on bis(benzothiophene) ethylene compounds as an organic semiconductor layer are relatively high, wherein the migration rate can be 5.79cm<2>V<-1>s<-1> at most and the switch ratio is larger than 10<6>; the polymers have a good application prospect to PFET devices.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a bis(benzothiophene)ethylene polymer, a preparation method thereof and its application in field effect transistors. Background technique [0002] Polymer field-effect transistors (PFETs) are active devices that use highly π-conjugated polymers as semiconductor materials and control the conductivity of materials through electric fields. Great progress has been made in recent years. PFETs have many excellent characteristics of organic semiconductors, such as flexibility, large-area preparation, solution processing, low cost, and good compatibility with plastic substrates. They have attracted more and more attention and are expected to become the next generation The key components of optoelectronic devices and circuits, such as smart cards, electronic labels, electronic paper, memory, sensors and active matrix displays, have extremely high applic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D333/54C07F7/22H01L51/30
Inventor 于贵黄剑耀刘晓彤毛祖攀张卫锋高冬
Owner INST OF CHEM CHINESE ACAD OF SCI
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