Dicarbonyl bridged pyrrolo-pyrrole-dione polymer as well as preparation method and application thereof

A polymer, polymerization reaction technology, applied in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., can solve the problem that the mobility cannot meet the wide range of applications, achieve excellent thermal stability, wide UV-Vis absorption spectrum, good film-forming effect

Active Publication Date: 2016-08-10
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 p

Method used

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  • Dicarbonyl bridged pyrrolo-pyrrole-dione polymer as well as preparation method and application thereof
  • Dicarbonyl bridged pyrrolo-pyrrole-dione polymer as well as preparation method and application thereof
  • Dicarbonyl bridged pyrrolo-pyrrole-dione polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0042] Example 1, polymer PDTO-1 synthesis (R=2-decyl dodecyl 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] Add 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 liquid bromine (2.0 ml, 40 mmol) was slowly added dropwise. After completion, the reaction system was heated to 60° C. and stirred for 4 hours under the protection of argon. 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 resulting 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 characterization data are as follows:

[0046] Mass Spectrum: HRMS(m / z):...

Example Embodiment

[0059] Example 2, polymer PDTO-2 synthesis (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 belonging 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), tetrahydrofuran (20 mL) was cooled to -20°C, lithium diisopropylamide (1.2 mL, 2.4 mmol) was added dropwise under the protection of argon, and then the temperature was slowly raised to 0°C to continue the reaction 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 characterization data are as follows:

[0065] Mass Spectrum: HRMS(m / z):[M] + :1...

Example Embodiment

[0073] Spectral properties of embodiment 3, polymer PDTO-1 and PDTO-2

[0074] image 3 and Figure 4 UV-Vis absorption spectra of the 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 molecule has a 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 dicarbonyl bridged pyrrolo-pyrrole-dione polymer as well as a preparation method and application thereof. The structural formula of the dicarbonyl bridged pyrrolo-pyrrole-dione polymer is shown by formula I. As shown in the formula I, R is selected from any one of C5-C80 (preferably C5-C50) linear or branched alkyl, and n is a polymerization degree that is 5-200. The invention also provides a preparation method of the polymer shown by the formula I. The synthetic route of the polymer disclosed by the invention is simple and feasible, is few in synthetic step, and is suitable for large-scale synthesis. The mobility ratio and on-off ratio of a field-effect transistor prepared by taking the dicarbonyl bridged pyrrolo-pyrrole-dione polymer disclosed by the invention as an organic semiconductor layer are relatively high, the mobility ratio is 0.54cm<2>V<-1>s<-1>, and the on-off ratio is greater than 10<6>. The polymer disclosed by the invention has a good application prospect in an organic field-effect device.

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 (OFETs for short) are active devices that use organic semiconductor materials as carrier transport layers and control the conductivity of materials through electric fields. They are based on the unique structural characteristics of π-conjugated molecules and Important applications derived from rich physical and chemical properties. High-performance OFETs have broad application prospects. Its successful application in the fields of smart cards, sensors, electronic radio frequency tags, large-screen displays, and integrated circuits will certainly promote technological innovation in many fields such as information, energy, and life, and will definitely contribute to economic development. ...

Claims

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Application Information

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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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