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Annulated indigo receptor, and polymer, preparation method and applications thereof

A polymer and compound technology, applied in the field of materials, can solve problems such as the development of high-performance n-type materials and bipolar materials.

Active Publication Date: 2020-03-10
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

Most of the current high-performance OFETs materials are p-type materials, and the development of high-performance n-type materials and bipolar materials is lagging behind

Method used

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  • Annulated indigo receptor, and polymer, preparation method and applications thereof
  • Annulated indigo receptor, and polymer, preparation method and applications thereof
  • Annulated indigo receptor, and polymer, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1, polymer P2FBAI-V

[0085] 1a) Difluoroindigo (i.e. 2F-indigo)

[0086] 30g of 5-fluoro-2-nitrobenzaldehyde (0.177mol), 1000mL of acetone and 440mL of water were successively added into the round bottom flask, and the mixture was sonicated until clear. 2mol / L sodium hydroxide (8.5g, 0.212mol) aqueous solution was slowly added dropwise under stirring. The mixture was stirred at room temperature for 48 hours. The obtained suspension was filtered, washed with water, ethanol and acetone successively, and dried to obtain a blue product (18.1 g, 68.4%).

[0087] The structural characterization data are as follows:

[0088] The product is poorly soluble in common deuterated solvents, so 1 H NMR and 13 C NMR not yet available. Mass spectrum: HREI: [M] + calcd for C 16 h 8 f 2 N 2 o 2 :298.0554,found:298.0552.

[0089] 1b) Difluorocyclized indigo (i.e. 2FBAI)

[0090] Difluoroindigo (8.0g, 26.8mmol, 1.0equiv) was dissolved in 350mL o-xylene and heated ...

Embodiment 2

[0112] Embodiment 2, polymer P2ClBAI-V

[0113] 2a) Dichloroindigo (i.e. 2Cl-indigo)

[0114] 30g of 5-chloro-2-nitrobenzaldehyde (0.162mol), 1000mL of acetone and 440mL of water were successively added into the round bottom flask, and the mixture was sonicated until clear. 2mol / L sodium hydroxide (7.8g, 0.194mol) aqueous solution was slowly added dropwise under stirring. The mixture was stirred at room temperature for 48 hours. The obtained suspension was filtered, washed with water, ethanol and acetone successively, and dried to obtain a blue product (17.7 g, 66.1%).

[0115] The structural characterization data are as follows:

[0116] The product is poorly soluble in common deuterated solvents, so 1 H NMR and 13 C NMR not yet available. Mass spectrum: HREI: [M] + calcd for C 16 h 8 Cl 2 N 2 o 2 :329.9963,found:329.9960.

[0117] 2b) Dichlorocyclized indigo (i.e. 2ClBAI)

[0118] Dichloroindigo (10.0g, 30.2mmol, 1.0equiv) was dissolved in 400mL o-xylene and he...

Embodiment 3

[0140] Embodiment 3, the spectral performance of polymer P2FBAI-V and P2ClBAI-V, electrochemical performance and field effect transistor performance

[0141] 1) Spectral and electrochemical properties of polymers P2FBAI-V and P2ClBAI-V

[0142] figure 1 UV-Vis absorption spectra of polymers P2FBAI-V and P2ClBAI-V in solutions and films.

[0143] Depend on figure 1 It can be seen that the optical bandgaps of polymers P2FBAI-V and P2ClBAI-V are 1.15eV and 1.09eV respectively (the optical bandgaps are based on the formula E g =1240 / λ calculation, where E g is the optical band gap, and λ is the boundary value of the UV absorption curve). Depend on figure 1 It can be seen that both polymers have relatively strong intramolecular charge transfer peaks, indicating that the intermolecular forces of the polymers are relatively strong.

[0144] figure 2 Cyclic voltammetry curves of polymer P2FBAI-V and P2ClBAI-V films. The measurement was carried out on a CHI660c electrochemi...

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Abstract

The invention discloses an annulated indigo receptor, and a polymer, a preparation method and applications thereof, wherein the structure of the polymer is represented by a formula I, and in the formula I, R is C1-C40 straight-chain or branched-chain alkyl. The invention also provides a preparation method of the polymer represented by the formula I. According to the invention, the raw materials are commercial products, the synthesis route is simple, and the synthesis method has universality; and the organic field effect transistor prepared by taking the novel annulated indigo polymer as an organic semiconductor layer has the highest hole mobility of 1.83 cm<2>V<-1>s<-1> and the highest electron mobility of 1.21 cm<2>V<-1>s<-1>, and has good application prospect in bipolar organic field effect transistor devices.

Description

technical field [0001] The invention belongs to the field of materials, and relates to a cyclized indigo acceptor and a polymer as well as a preparation method and application thereof. Background technique [0002] Organic field-effect transistors (OFETs for short) are a class of active devices that use π-conjugated organic semiconductor materials as the transport layer and control the conductivity of the material through a vertical electric field. OFETs are the key unit devices of organic optoelectronic devices and circuits. They have the advantages of light weight, solution processing, and good flexibility. They will have broad application prospects in future electronic products such as foldable displays, mobile phones, and computers. [0003] The semiconductor layer material of OFETs can be either organic small molecule material or high molecular polymer material. High molecular polymer materials have good flexibility and can be prepared and processed in a large area by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/05H01L51/30
CPCC08G61/126C08G61/122C08G2261/124C08G2261/146C08G2261/228C08G2261/3223C08G2261/3241C08G2261/3327C08G2261/92H10K85/151H10K10/00
Inventor 刘云圻杨杰蒋雅倩赵志远易征然郭云龙王帅
Owner INST OF CHEM CHINESE ACAD OF SCI
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