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A class of diketopyrrolopyrrole polymers bridged by dicarbonyl group and its preparation method and application

A technology of polymer and polymerization reaction, which is applied in the manufacture of semiconductor/solid-state devices, electrical components, circuits, etc., can solve the problems that the mobility cannot meet the wide application, and achieve excellent thermal stability, wide ultraviolet-visible light absorption spectrum, good The effect of film formation

Active Publication Date: 2018-04-03
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 mobility and other properties of the existing polymer field effect transistor devices still cannot meet the needs of wide application, so it is of great significance to continue to develop new polymer materials, and it also gives us the development of research results and technologies with independent intellectual property rights. Seizing the commanding heights of technology provides opportunities

Method used

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  • A class of diketopyrrolopyrrole polymers bridged by dicarbonyl group and its preparation method and application
  • A class of diketopyrrolopyrrole polymers bridged by dicarbonyl group and its preparation method and application
  • A class of diketopyrrolopyrrole polymers bridged by dicarbonyl group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1. Synthesis of polymer PDTO-1 (R=2-decyldodecyl in formula I) (its synthetic route is as follows: figure 2 shown)

[0043] 1) Synthesis of compound 1,2-bis(5-bromothienyl)ethane-1,2-dione (2) belonging to formula IV

[0044] Mix 1,2-bis(2-thienyl)ethane-1,2-dione (2.0 g, 10 mmol), sodium bicarbonate (3.4 g, 40 mmol) in chloroform (40 mL) ) solution was cooled to 0°C and slowly added dropwise bromine (2.0 mL, 40 mmol). After completion, the reaction system was heated to 60°C under argon protection and stirred for 4 hours. After cooling to room temperature, it was poured into water and extracted three times with chloroform. After removing the organic solvent under reduced pressure, the obtained solid residue was recrystallized. The obtained yellow solid was dried under vacuum at room temperature to obtain 2.2 g of the target product. Yield: 58%.

[0045] The structural representation data is as follows:

[0046] Mass spectrum: HRMS (m / z): [M] + :379.7994.....

Embodiment 2

[0059] Example 2. Synthesis of polymer PDTO-2 (R=4-decyltetradecyl in formula I) (its synthetic route is as follows: figure 2 shown)

[0060] 1) Synthesis of compound 2 belonging to formula IV

[0061] The synthesis of compound 2 was carried out with reference to Example 1.

[0062] 1) Synthesis of compound 4b assigned to formula VIII

[0063] 3b (973 mg, 1.0 mmol), 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.6 mL, 3.0 mmol) and tetrahydrofuran (20 mL), cooled to -20°C, added dropwise lithium diisopropylamide (1.2 mL, 2.4 mmol) under argon protection, and then slowly warmed to 0°C and continued to react for 1 h. The reaction was quenched with saturated aqueous ammonium chloride, extracted with dichloromethane, dried over anhydrous sodium sulfate, recrystallized and dried under vacuum to give a red solid (796 mg). Yield: 65%.

[0064] The structural representation data is as follows:

[0065] Mass spectrum: HRMS (m / z): [M] + :1225.9324.

[0066] Hydrogen sp...

Embodiment 3

[0073] Example 3. Spectral properties of polymers PDTO-1 and PDTO-2

[0074] image 3 and Figure 4 UV-Vis absorption spectra of polymers PDTO-1 and PDTO-2 chlorobenzene solutions and films prepared for Examples 1 and 2.

[0075] Depend on image 3 It can be seen that this type of polymer exhibits strong absorption in the ultraviolet-visible region and even the near-infrared region, indicating that the polymer molecules have strong intramolecular charge transfer.

[0076] Depend on Figure 4 It can be seen that the two polymers exhibit strong ordered aggregation or ordered aggregation in the solid.

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Abstract

The invention discloses a diketopyrrolopyrrole polymer bridged by a dicarbonyl group, a preparation method and application thereof. The structural formula of the diketopyrrolopyrrole bridged dicarbonyl polymer is shown in Formula I. In the above formula I, R is selected from any one of the following: C5-C80 (preferably C5-C50) straight-chain or branched-chain alkyl, n is a polymerization degree of 5-200. The present invention also provides a preparation method of the polymer represented by formula I. The synthesis route of the present invention is simple and easy, has few synthesis steps, and is suitable for large-scale synthesis. The field effect transistor prepared by using the diketopyrrolopyrrole bridged dicarbonyl polymer of the present invention as the organic semiconductor layer has relatively high mobility and on-off ratio, the mobility is 0.54cm2V-1s-1, and the on-off ratio is greater than 106. 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 a class of dicarbonyl bridged diketopyrrolopyrrole polymers and a preparation method and application thereof. Background technique [0002] Organic field-effect transistors (Organic Field-effect Transistors, referred to as OFETs) are active devices that use organic semiconductor materials as the carrier transport layer and control the conductivity of materials through an electric field. They are based on the unique structural characteristics of π-conjugated molecules and Important applications derived from rich physicochemical properties. High-performance OFETs have broad application prospects. Their successful application in the fields of smart cards, sensors, electronic radio frequency tags, large-screen displays and integrated circuits will inevitably promote technological innovation in many fields such as information, energy, and life, and will certain...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/30
CPCC08G61/121C08G61/124C08G61/126C08G2261/411C08G2261/12C08G2261/3221C08G2261/3223H10K85/113H10K85/151
Inventor 张卫锋毛祖攀郑乃杭陈智慧于贵
Owner INST OF CHEM CHINESE ACAD OF SCI
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