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Synthesis and application of novel pyridinotriazole receptor and luminescent polymer thereof

A technology of polymers and compounds, applied in the field of materials, to achieve good application prospects, simple synthetic routes, and high yield effects

Pending Publication Date: 2021-10-15
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

[0003] With the gradual and in-depth research on organic optoelectronic devices (such as OFETs, organic photovoltaic devices, and OLEDs, etc.), great progress has been made in the carrier mobility and photoelectric conversion efficiency of organic semiconductors. The synthesis and preparation of organic semiconductor materials with specific characteristics has always been a great challenge

Method used

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  • Synthesis and application of novel pyridinotriazole receptor and luminescent polymer thereof
  • Synthesis and application of novel pyridinotriazole receptor and luminescent polymer thereof
  • Synthesis and application of novel pyridinotriazole receptor and luminescent polymer thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1, polymer PPT-TT-PT-2FBT, R is 5-decyl pentadecyl (formula I-1)

[0089]

[0090] The reaction equation is as figure 1 (a) shown.

[0091] (1) 4,7-Dibromo-2H-[1,2,3]triazolo[4,5-c]pyridine

[0092] Add 2,5-dibromo-3,4-diaminopyridine (4.00g, 14.99mmol) and 60mL acetic acid into a 100mL two-necked flask, ultrasonicate for 10min, then dissolve sodium nitrite ( 1.55g, 22.48mmol) was dropped into a two-necked flask, and reacted at 30°C for 24h. Wash the product twice with distilled water, then filter the product and transfer it to a 250mL round bottom flask, add about 100mL of ethanol and spin dry (take away water with ethanol), and dry to obtain 4.05g of white solid. Yield: 97.12%.

[0093] The structural characterization data are as follows:

[0094] Mass Spectrum: ESI-MS: [M] - calcd for C 5 HBr 2 N 4 - :276.85,found:276.90.

[0095] H NMR and C NMR: 1 H NMR (400MHz, DMSO) δ8.49 (m, 1H). 13 C NMR (100MHz, DMSO) δ144.65, 140.37, 132.44, 131.32,...

Embodiment 2

[0113] Embodiment 2, polymer PPT-TT-PT-TT, R is 5-decyl pentadecyl (formula I-2)

[0114]

[0115] Wherein the definition of R is the same as the definition of R in the aforementioned formula 1.

[0116] The reaction equation is as figure 1 (b) shown.

[0117] The first three steps are the same polymer as PPT-TT-PT-2FBT;

[0118] Polymer PPT-TT-PT-TT:

[0119] 2,5-bis(7-bromo-2-(5-decylpentadecyl)-2H-[1,2,3]triazolo[4,5-c]pyridine-4 shown in formula 1 -yl)thieno[3,2-b]thiophene (100.0mg, 0.081mmol), 2,5-bis(trimethyltin)thieno[3,2-b]thiophene (37.73mg, 0.081mmol), Catalyst tris(dibenzylideneacetone)dipalladium (2.25mg, 0.0024mmol), ligand tris(o-tolyl)phosphine (5.84mg, 0.019mmol) and chlorobenzene (5mL) were added in the reaction flask, under argon Three freeze-pump-thaw cycles were performed to remove oxygen, and then the reaction mixture was heated to 125° C. for 48 h of polymerization. After cooling, 100 mL of methanol was added, stirred at room temperature for 3 ...

Embodiment 3

[0126] Optical performance, electrochemical performance and field effect transistor performance of embodiment 3, polymer PPT-TT-PT-2FBT and PPT-TT-PT-TT

[0127] (1) Optical and electrochemical properties of polymers PPT-TT-PT-2FBT and PPT-TT-PT-TT

[0128] figure 2 For the polymer PPT-TT-PT-2FBT ( figure 2 (a)) and PPT-TT-PT-TT ( figure 2 (b) UV-Vis absorption spectra in solution and film.

[0129] Depend on figure 2 It can be seen that the polymer film PPT-TT-PT-2FBT ( figure 2 (a)) and PPT-TT-PT-TT ( figure 2 The optical bandgaps of (b)) are 1.77eV and 1.73eV 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 2 It can be seen that all three polymers have relatively strong intramolecular charge transfer peaks, indicating that the intermolecular forces of the polymers are relatively strong.

[0130] image 3 For the p...

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Abstract

The invention relates to synthesis and application of a novel pyridinotriazole receptor and a luminescent polymer of the novel pyridinotriazole receptor. The structural formula of the luminescent polymer is shown as a formula I. An organic field effect transistor prepared by taking the pyridino-triazole luminescent polymer as a semiconductor layer has relatively high hole mobility (the highest hole mobility is 0.28 cm<2>V<-1>s<-1>) and solid-state luminescent quantum yield (the highest solid-state luminescent quantum yield is 10%), and the pyridino-triazole luminescent polymer has a good application prospect in the organic field effect transistor and a luminescent transistor. The invention synthesizes a novel pyridinotriazole (PT for short) receptor and a luminescent polymer thereof, and studies the luminescent characteristics of the novel pyridinotriazole receptor and the luminescent polymer thereof and the application of the novel pyridinotriazole receptor and the luminescent polymer in OFETs. The pyridinotriazole polymer further expands the types of luminescent polymer materials, and has a good application prospect in organic optoelectronic devices.

Description

technical field [0001] The invention relates to the synthesis and application of a novel pyridotriazole acceptor and a light-emitting polymer thereof, belonging to the field of materials. Background technique [0002] Organic light-emitting transistors (OLETs) are probably the smallest integrated optoelectronic devices to date, which simultaneously combine the switching function of organic field-effect transistors (OFETs) and the electroluminescent properties of organic light-emitting diodes (OLEDs). OLETs provide a good architectural platform for the study of charge injection, charge transport, charge carrier recombination, and light emission in organic semiconductors. This unique architecture makes it ideal for the development of next-generation display technologies and small photonic devices and circuits, which are expected to be applied In new flexible displays, organic electro-pumped lasers and optical communication technologies, etc. [0003] With the gradual and in-d...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/54C09K11/06
CPCC08G61/126C08G61/122C08G61/123C09K11/06C09K2211/1466C09K2211/1458C09K2211/1483C08G2261/124C08G2261/3243C08G2261/3241C08G2261/92C08G2261/95C08G2261/522H10K85/113H10K85/111
Inventor 刘云圻陈金佯匡俊华郭云龙杨杰
Owner INST OF CHEM CHINESE ACAD OF SCI
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