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Thiadiazolobenzotriazole near-infrared organic photoelectric small molecule as well as preparation method and application thereof

A benzotriazole and near-infrared technology, used in photovoltaic power generation, organic chemistry, circuits, etc., can solve problems such as the lack of organic optoelectronic materials, and achieve the effects of good application prospects, good solubility and high crystallinity

Pending Publication Date: 2022-04-22
UNIV OF ELECTRONIC SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned problems or deficiencies, in order to solve the problem that the existing spectral absorption range is greater than 1 μm and the organic optoelectronic materials that can be applied to high-sensitivity organic light detectors are scarce, the present invention provides a thiadiazobenzotriazole near-infrared An organic photoelectric small molecule and its preparation method and application. The material is centered on [1,2,5]thiadiazolo[3,4-f]benzotriazole, connected with thiophene structural units, and 2-( 2-methylene-3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile is terminal, has solubility, is beneficial to preparation, and can be applied to highly sensitive organic photodetectors

Method used

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  • Thiadiazolobenzotriazole near-infrared organic photoelectric small molecule as well as preparation method and application thereof
  • Thiadiazolobenzotriazole near-infrared organic photoelectric small molecule as well as preparation method and application thereof
  • Thiadiazolobenzotriazole near-infrared organic photoelectric small molecule as well as preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0036] Synthesis of embodiment 1, SM1.

[0037] chemical reaction flow chart figure 1 Shown, concrete reaction steps and reaction conditions are as follows:

[0038] Compound 3 ( figure 1 The preparation of the compound marked as 3): under an inert atmosphere, compound 1 (680mg, 1mmol) and compound 2 (112mg, 0.25mmol) in anhydrous toluene (10ml) solution, add Pd (PPh 3 ) 4 (11.6 mg, 0.01 mmol). The whole reaction system was heated to 110°C and stirred for 36 hours. After the reaction solution was cooled, methanol was added for precipitation, centrifuged, and the solid part was dissolved with chloroform, washed three times with water, and dried over anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent, using petroleum ether:dichloromethane (20:1) as eluent, separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain compound 3 (149 mg, 56%), MS (MALDI- TOF): m / z=1066.8.

[0039] Compound...

Embodiment 2

[0041] Synthesis of embodiment 2, SM2.

[0042] Wherein the synthesis of compound 3 and 4 is the same as in Example 1, and the chemical reaction flow diagram is as follows figure 1 Shown, the preparation reaction steps and reaction conditions of compound SM2 are as follows:

[0043] Under an inert atmosphere, 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (115 mg, 0.5 mmol) was added to compound 4 (56 mg , 0.05mmol) and pyridine (0.2mL, 2.5mmol) in anhydrous chloroform (15ml), heated to 60°C and stirred for 12 hours. After the reaction liquid was cooled down, methanol was added for precipitation, centrifuged, and the solid part was dissolved with chloroform, washed with water three times, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, petroleum ether: chloroform (2:1) was used as eluent, and the product was separated by silica gel chromatography. The product was recrystallized from chlorofo...

Embodiment 3

[0044] Example 3, Determining the photodetection performance test of organic optoelectronic molecules SM1 and SM2

[0045] Diode-type organic photodetection devices were prepared by solution spin coating with thiadiazolobenzotriazole near-infrared organic optoelectronic small molecules SM1 and SM2 prepared in Examples 1 and 2 as acceptor materials and PTB7-Th as donor materials. The device structure is ITO / ZnO / SM1 or SM2:PTB7-Th / MoOx / Ag.

[0046] The preparation method is as follows: the transparent conductive glass with ITO is ultrasonically cleaned with deionized water, acetone, and isopropanol successively for 15 minutes, and then the surface of the substrate is treated with ozone. A 30nm thick ZnO modification layer is coated on the surface of ITO. The organic optoelectronic molecules SM1 and SM2 were blended with PTB7-Th (1:1 mass ratio) and dissolved in chlorobenzene to obtain a 40 mg / mL solution. The solution is uniformly spin-coated on the ZnO modification layer at a...

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Abstract

The invention belongs to the field of organic photoelectric materials, and particularly relates to a thiadiazolobenzotriazole near-infrared organic photoelectric small molecule as well as a preparation method and application thereof. A quinonoid receptor unit [1, 2, 5] thiadiazole [3, 4-f] benzotriazole with a strong electron deficiency characteristic is introduced into molecular design, A-D-A-D-A type thiadiazole benzotriazole near-infrared organic photoelectric small molecules are constructed, [1, 2, 5] thiadiazole [3, 4-f] benzotriazole is used as a central unit, D is a thiophene structural unit, 2-(2-methylene-3-oxo-2, 4-dioxo-1, 3, 4-thiadiazole) is used as an electron acceptor, and an electron acceptor unit is used as an electron acceptor. And 2, 3-dihydro-1H-indene-1-subunit) malononitrile is used as a terminal group, so that the band gap of molecules is effectively reduced. The preparation method is simple, the product is easy to dissolve and form a film, the extinction coefficient is high, the absorption range is over 1.2 microns, and the crystallinity is high; when the material is applied to near-infrared or wide-spectrum photoelectric detection devices, excellent performance is shown, the specific detection rate within the spectrum range of 0.4-1.2 microns can reach 10 < 11 > Jones or above, and the material has good application prospects.

Description

technical field [0001] The invention belongs to the field of organic optoelectronic materials, and in particular relates to a thiadiazolobenzotriazole near-infrared organic optoelectronic small molecule and its preparation method and application. The material is [1,2,5]thiadiazole[3,4 -f] benzotriazole structure. Background technique [0002] Organic photodetection diodes (OPD) have broad application prospects in image sensing, biomedical detection, optical communication, environmental monitoring, night vision, remote control, etc. (Science2009, 325, 1665-1667; Adv.Mater.2016, 28 , 5969-5974). OPD can be prepared on flexible substrates by simple and cheap solution film-forming technology, which is suitable for bending, folding, miniaturization, biocompatibility and other diverse products, and does not require refrigeration work. It will have huge commercial development value and market in the future (Laser Photonics Rev. 2020, 14, 2000262). However, limited by the lack of...

Claims

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Application Information

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IPC IPC(8): C07D513/04B05D7/24B05D5/06H01L51/42H01L51/46
CPCC07D513/04B05D7/24B05D5/06H10K30/20Y02E10/549
Inventor 袁柳蒋亚东太惠玲王洋顾德恩黎威志
Owner UNIV OF ELECTRONIC SCI & TECH OF CHINA
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