Near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyano thiophene

A cyanothiophene, molecular material technology, applied in photovoltaic power generation, organic chemistry, silicon organic compounds, etc., can solve the problems of small absorption spectrum, lack of organic photoelectric materials, etc., to reduce the molecular band gap, enhance the charge transfer effect, The effect of good solubility

Active Publication Date: 2022-03-18
UNIV OF ELECTRONICS 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 problems of the lack of types of existing organic photoelectric materials and the relatively small absorption spectrum, the present invention provides a near-infrared organic photodetector based on 3-alkoxy-4-cyanothiophene Molecular materials and their preparation methods and applications

Method used

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  • Near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyano thiophene
  • Near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyano thiophene
  • Near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyano thiophene

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Embodiment 1

[0044] The synthesis of embodiment 1, CN5T

[0045] chemical reaction flow chart figure 1 Shown, concrete reaction steps and reaction conditions are as follows:

[0046] Compound 2 ( figure 1 The preparation of the compound marked as 2) in: under inert atmosphere, compound 1 ( figure 1The solution of the compound marked as 1) (2.37g, 10mmol) in anhydrous tetrahydrofuran (100mL) was lowered to -78°C, and a solution of n-butyl lithium (2.4M, 4.17mL) was slowly added dropwise, and the reaction was stirred for 1h. Then dry N,N-dimethylformamide (1.46g, 20mmol) was added slowly at -78°C, and the reaction was stirred for 1h. The reaction solution was raised to room temperature to continue the reaction for 3 h, and then 5 mL of water was added to quench the reaction. The reaction solution was extracted with dichloromethane, washed three times with water, and dried over anhydrous magnesium sulfate. The organic phase was rotovapped to remove the solvent, using petroleum ether:dich...

Embodiment 2

[0050] The synthesis of embodiment 2, CN4T

[0051] chemical reaction flow chart figure 2 The specific reaction steps and reaction conditions are as follows:

[0052] Compound 8 ( figure 2 The preparation of the compound marked as 8 in the middle: under inert atmosphere, compound 3 (1.47g, 4.26mmol) and compound 7 ( figure 2 In the solution of the compound marked as 7) (1.39g, 1.42mmol) in anhydrous toluene (30mL), add Pd(PPh 3 ) 4 (116 mg, 0.1 mmol). The whole reaction system was heated to 110°C and stirred for 48 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 (4:1) as eluent, separated by silica gel column chromatography, and the purple solid product-compound 8 (0.91g, 69%) was obtained after r...

Embodiment 3

[0054] Example 3 Determination of the UV-visible-near-infrared absorption spectrum of the organic optoelectronic molecule CN5T in a thin film state: the organic optoelectronic molecule CN5T was dissolved in chloroform to prepare a solution with a concentration of 20 mg / mL, and a part of the solution was spin-coated on a quartz plate to form a film. The absorption spectrum measured in the thin film state is as follows image 3 As shown, the absorption spectrum exceeds 1.2 μm.

[0055] It can be seen from the above examples that the present invention applies the 3-alkoxy-4-cyanothiophene structure to the construction of near-infrared organic photoreceptor molecules, wherein the alkoxy group forms a strong electron-donating conjugation effect with the central unit, and the cyano group Form a strong electron-pulling conjugation effect with the terminal unit, which can simultaneously improve the electron-donating ability of the former and the electron-accepting ability of the latt...

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Abstract

The invention belongs to the field of organic photoelectric materials, and particularly relates to a near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyano thiophene as well as a preparation method and application of the near-infrared organic photoelectric molecular material. A 3-alkoxy-4-cyano thiophene structure is used for constructing a near-infrared organic photoelectric acceptor molecule, alkoxy and a central unit part form a strong electron donating conjugation effect, cyano and a terminal unit form a strong electron withdrawing conjugation effect, and the electron donating ability of the alkoxy and the electron accepting ability of the cyano and the terminal unit can be improved at the same time. Alkoxy and cyano are used for modifying a molecular skeleton structure, so that the dielectric constant of molecules can be effectively improved, the dissociation of excitons in a photoelectric process is facilitated, and the generation efficiency of free charges is improved. And the film is easily dissolved in common organic solvents, so that a high-quality film can be prepared by a solution spin-coating method. The absorption spectrum range of the prepared organic photoelectric molecular film exceeds 1.2 microns, and the organic photoelectric molecular film shows excellent performance when applied to organic photoelectric detectors.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a near-infrared organic photoelectric molecular material based on 3-alkoxy-4-cyanothiophene and its preparation method and application. Background technique [0002] Organic optoelectronic materials are rich in structure, cheap to prepare, solution-processable, suitable for large-area and flexible devices, and have good application potential in light-emitting devices, field-effect transistors, photovoltaic cells and other fields. The absorption spectrum reaches the near-infrared region, especially organic optoelectronic materials larger than 1 micron, which can be used in organic photodetection devices to realize the detection of near-infrared light information, in image sensing, biomedical detection, optical communication, environmental monitoring, night vision , remote control and other aspects have broad application prospects (Science2009, 325, 1665-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D495/14C07F7/08C07D333/38C07D417/14C07D333/60C07D333/78H01L51/46
CPCC07D495/04C07D495/14C07F7/0816C07F7/0832C07D333/38C07D417/14C07D333/60C07D333/78H10K85/615H10K85/626H10K85/655H10K85/657H10K85/6576H10K85/40Y02E10/549
Inventor 袁柳太惠玲王洋蒋亚东顾德恩黎威志
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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