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Diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer as well as preparation method and application of diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer

A technology of polymers and compounds, applied in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., can solve problems that cannot meet actual needs, achieve good optical properties and thermal stability, simple and efficient synthesis routes, narrow energy gap effect

Inactive Publication Date: 2015-07-08
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

But generally speaking, the existing organic semiconductor materials still cannot meet the actual needs.

Method used

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  • Diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer as well as preparation method and application of diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer
  • Diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer as well as preparation method and application of diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer
  • Diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer as well as preparation method and application of diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1, poly{2,5-di(2-octyldodecyl)-2,5-dihydro-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5 -(3,6-dimethoxythiophene[3,2-b]thiophene)-2,5-diyl}(polymer PDMOTT-118, that is, R in formula Ⅰ 1 = R 2 = 2-Octyldodecyl, R 3 = R 4 =CH 3 )

[0053] 1) Synthesis of 2,5-bis(trimethyltin-based)-3,6-dimethoxythiophene[3,2-b]thiophene (2)

[0054] Under the protection of argon, 3,6-dimethoxythiophene[3,2-b]thiophene (1) (0.8g, 4.0mmol) was dissolved in 20mL of anhydrous tetrahydrofuran, cooled to -78°C, and added dropwise 2.5M solution of n-butyllithium in n-hexane (4.0mL, 2.5eq.). After the addition, control the temperature of the reaction suspension at -78°C, stir for 1 hour, then slowly raise the temperature to 0°C, stir for 5 minutes, then cool to -78°C and add 1.0M tetrahydrofuran solution of trimethyltin chloride (10.0mL, 10mmol, 2.5eq.), and then the reaction system was stirred at room temperature overnight. After the mixture was quenched with water, it was extracted with e...

Embodiment 2

[0064] Example 2, poly{2,5-di(2-decyltetradecyl)-2,5-dihydro-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5 -(3,6-dimethoxythiophene[3,2-b]thiophene-2,5-diyl}(compound PDMOTT-122, that is, R in formula Ⅰ 1 = R 2 = 2-decyltetradecyl, R 3 = R 4 =CH 3 )

[0065] 1) According to the steps in Example 1, 2,5-bis(trimethyltinyl)-3,6-dimethoxythiophene[3,2-b]thiophene (2) was synthesized.

[0066] 2) Synthesis of polymer PDMOTT-122

[0067] Compound (2) (105.18mg, 0.2mmol) and 3,6-bis(5-bromo-2-thienyl)-2,5-bis(2-decyltetradecyl)-pyrrolo[3, 4-c]pyrrole-1,4-dione (4) (226.28 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium (9 mg), tris(o-tolyl)phosphine (24.6 mg) and chlorine Benzene (5 mL) was added into the reaction flask, three freeze-pump-thaw cycles were performed in argon to remove oxygen, and then the reaction mixture was heated to 110° C. for 24 h under argon protection. After cooling, 200 mL of methanol / 6M HCl mixture (v / v 20:1) was added, stirred at room temperature for 2 h, ...

Embodiment 3

[0072] Example 3, poly{2,5-di(4-decyltetradecyl)-2,5-dihydro-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5 -(3,6-dimethoxythiophene[3,2-b]thiophene)-2,5-diyl}(compound PDMOTT-320, that is, R in formula Ⅰ 1 = R 2 = 4-decyltetradecyl, R 3 = R 4 =CH 3 )

[0073] 1) According to the steps in Example 1, 2,5-bis(trimethyltinyl)-3,6-dimethoxythiophene[3,2-b]thiophene (2) was synthesized.

[0074] 2) Synthesis of polymer PDMOTT-320

[0075] Compound (2) (105.18mg, 0.2mmol) and 3,6-bis(5-bromo-2-thienyl)-2,5-bis(4-decyltetradecyl)-pyrrolo[3, 4-c]pyrrole-1,4-dione (5) (226.28mg, 0.2mmol), tris(dibenzylideneacetone)dipalladium (9mg), tris(o-tolyl)phosphine (24.6mg) and chlorine Benzene (5 mL) was added into the reaction flask, three freeze-pump-thaw cycles were performed in argon to remove oxygen, and then the reaction mixture was heated to 110° C. for 24 h under argon protection. After cooling, 200 mL of methanol / 6M HCl mixture (v / v 20:1) was added, stirred at room temperature for 2 h, and...

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Abstract

The invention discloses a diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer, a preparation method of the diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer and application of the diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer to a field effect transistor. The diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer has a structural formula as shown in the formula I, wherein R1 and R2 are respectively and independently selected from any one of C1-C120 straight-chain or branch-chain alkyls; and R3 and R4 are respectively and independently selected from any one of C1-C60 straight-chain or branch-chain alkyls. The invention also provides the preparation method of the polymer as shown in the formula I. The synthesis route is simple and efficient, raw materials are easily obtained, and the preparation method is suitable for large-scale synthesis. The field effect transistor prepared by taking the diketopyrrolopyrrole and thieno[3,2-b]thiophene polymer disclosed by the invention as an organic semiconductor layer is relatively high in migration rate and switch ratio and has the highest migration rate of 2.0cm<2>V<-1>s<-1> and the switch ratio of 105. The polymer disclosed by the invention has a favorable application prospect in organic field effect transistor devices.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a kind of pyrrolopyrrole diketopo-dithiophene polymer, a preparation method thereof and its application in field effect transistors. Background technique [0002] Field Effect Transistor (FETs for short) is an active electronic device that uses electric field effects to control the magnitude of current in semiconductors. This type of electronic devices widely used at present are prepared with traditional inorganic semiconductor materials such as silicon, germanium, gallium, and their derivatives as core materials. The superior performance of these inorganic materials and devices has effectively promoted the development of science and technology, economy, society and human progress all over the world. However, due to the depletion of mineral resources of traditional semiconductor materials and the serious environmental pollution and huge water ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30
Inventor 张卫锋毛祖攀黄剑耀高冬陈智慧于贵
Owner INST OF CHEM CHINESE ACAD OF SCI
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