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Star-shaped three-dimensional conjugated molecule based on triphenylamine-benzothiadiazole and its preparation method and application

A technology of benzothiadiazole and conjugated molecule is applied in the field of star-shaped three-dimensional conjugated molecule and its preparation, and can solve the energy conversion efficiency of triphenylamine donor-bridging group-benzothiadiazole acceptor material Low problems, to achieve the effect of good processability, good stability and good solubility

Inactive Publication Date: 2011-12-28
INST OF CHEM CHINESE ACAD OF SCI
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  • Description
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Problems solved by technology

From the reported device results, the energy conversion efficiency based on this triphenylamine donor-bridging group-benzothiadiazole acceptor material is generally low, which may be related to the fact that such molecules contribute less to visible light absorption. The introduction of bridging groups is related to

Method used

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  • Star-shaped three-dimensional conjugated molecule based on triphenylamine-benzothiadiazole and its preparation method and application
  • Star-shaped three-dimensional conjugated molecule based on triphenylamine-benzothiadiazole and its preparation method and application
  • Star-shaped three-dimensional conjugated molecule based on triphenylamine-benzothiadiazole and its preparation method and application

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Experimental program
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Embodiment 1

[0038] The synthetic route of conjugated molecule 1 is as follows (see the synthetic route for the yield of each step product).

[0039]

[0040]

[0041] (1) Synthesis of Intermediate I

[0042] Add 4,7-dibromobenzothiadiazole (250mg, 0.85mmol), 5-hexyl-5″-tributyltin-2,2′:5′,2″-trithiophene ( 460mg, 0.74mmol) and anhydrous tetrahydrofuran (10mL), purged the air with nitrogen, and added dichlorobis(triphenylphosphine)palladium (14mg, 0.02mmol). Reflux at a temperature of 80°C for 24 hours. The organic phase was extracted with dichloromethane, and the extracted organic phase was dried over anhydrous magnesium sulfate. After removing the solvent, it was purified by silica gel column chromatography (eluent: petroleum ether / chloroform mixed solvent, volume ratio 1:1) to obtain a brown solid (182 mg, 45%). 1 H NMR (400MHz, CDCl 3 ): δ8.02(d, J=7.6Hz, 1H), 7.85(d, J=7.6Hz, 1H), 7.70(d, J=7.6Hz, 1H), 7.23(d, J=3.9Hz, 1H ), 7.18(d, J=3.1Hz, 1H), 7.04(d, J=3.2Hz, 1H), 7.01(...

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Abstract

The invention relates to a class of star-shaped three-dimensional conjugated molecules based on triphenylamine-benzothiadiazole and a preparation method thereof, and the application of the molecules as active layer materials in organic semiconductor devices such as organic solar cells (OPV). The star-shaped three-dimensional conjugated molecule based on triphenylamine-benzothiadiazole of the present invention has good solar light harvesting ability and hole transport ability, and has good solution processability and thermal stability, and is useful for making organic solar energy Ideal material for battery devices. Its general structure is as follows:

Description

technical field [0001] The invention relates to a class of star-shaped three-dimensional conjugated molecules based on triphenylamine-benzothiadiazole and a preparation method thereof, and the application of the molecules as active layer materials in organic semiconductor devices such as organic solar cells (OPV). Background technique [0002] Due to their good optical and electrical properties, organic semiconductor materials have become an important part of organic electronics research. Compared with traditional inorganic semiconductor devices, the devices made of them have the following advantages: low cost, flexibility, light weight , Can be prepared in a large area, etc. Based on these advantages, people have great interest in the research of organic electronics. Organic semiconductor devices mainly include organic solar cells (OPV), organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). In recent years, the research and development of OPV...

Claims

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Application Information

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IPC IPC(8): C07D417/14H01L51/46
CPCY02E10/50Y02E10/549
Inventor 占肖卫范海军尚会霞
Owner INST OF CHEM CHINESE ACAD OF SCI
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