Organic semiconductor material containing benzotriazole group, preparation method thereof and organic solar cell

An organic semiconductor and benzotriazole-based technology, applied in the field of optoelectronic materials, can solve the problems of low utilization rate of sunlight and insufficient absorption of sunlight, and achieve the effects of broadening the absorption band, good photovoltaic performance, and improving utilization rate

Active Publication Date: 2013-01-02
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
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Problems solved by technology

From the absorption spectrum, their maximum absorption wavelength is 500nm. Compared with the solar spectrum, it can be seen that the absorption of sunlight by the material is obviously insufficient, and the utilization rate of sunlight is low; therefore, designing and synthesizing narrow-bandgap polycarbazole has become an important research. direction

Method used

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  • Organic semiconductor material containing benzotriazole group, preparation method thereof and organic solar cell
  • Organic semiconductor material containing benzotriazole group, preparation method thereof and organic solar cell
  • Organic semiconductor material containing benzotriazole group, preparation method thereof and organic solar cell

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preparation example Construction

[0031] A method for preparing a benzotriazole group-containing organic semiconductor material according to an embodiment, comprising the steps of:

[0032] Step S1, respectively provide compound A and compound B of the following structural formula:

[0033]

[0034] Among them, in compound A, R 1 for C 1 ~C 20 the alkyl group; in compound B, R 2 for C 1 ~C 20 the alkyl group;

[0035] Step S2, in an oxygen-free environment (consisting of an inert atmosphere, such as a nitrogen atmosphere or an argon atmosphere), add the compounds A and B to an organic solvent containing a catalyst in a molar ratio of 1:1, and the temperature is 90-120° C. The Heck coupling reaction was carried out for 24 to 72 h to obtain a benzotriazole group-containing organic semiconductor material with the following general structural formula:

[0036]

[0037] In the above formula, n is an integer greater than or equal to 10 and less than or equal to 50; the reaction formula is as follows:

...

Embodiment 1

[0052] The organic semiconductor material containing a benzotriazole group in this Example 1, namely poly{3,6-divinyl-N-octylcarbazole-2-octyl-4,7-dithiophene-1,2, 3-benzotriazole} (wherein R 1 for octyl, R 2 is octyl, n is 25), and its structural formula is as follows:

[0053]

[0054] The preparation steps of above-mentioned polymer are as follows:

[0055] Step 1, the preparation of 2-octyl-4,7-bis(5,5'-dibromothienyl)-1,2,3-benzotriazole, the reaction formula is as follows:

[0056]

[0057] The specific process is as follows: under dark conditions, compound 2-octyl-4,7-dithiophene-1,2,3-benzotriazole (2.37g, 6mmol) was dissolved in chloroform (60mL) and glacial acetic acid (60 mL) mixed solution, moved to an ice bath, then N-bromosuccinimide (2.35 g, 13.2 mmol) was added in batches, and reacted at room temperature for 12 h to obtain a reaction mixture.

[0058] The reaction mixture was extracted with dichloromethane three times and washed with water. The organi...

Embodiment 2

[0067] The organic semiconductor material containing a benzotriazole group in Example 2 is poly{3,6-divinyl-N-dodecylcarbazole-2-hexyl-4,7-dithiophene-1,2 , 3-benzotriazole} (wherein, R 1 is dodecyl, R 2 is hexyl, n is 32), and its structural formula is as follows:

[0068]

[0069] The preparation steps of above-mentioned polymer are as follows:

[0070] Step 1, the difference with step 1 in embodiment 1 is: hexyl replaces octyl;

[0071] Step 2, the preparation of poly{3,6-divinyl-N-dodecylcarbazole-2-hexyl-4,7-dithiophene-1,2,3-benzotriazole}, the reaction formula is as follows shown:

[0072]

[0073] Under nitrogen, 3,6-divinyl-N-dodecylcarbazole (116 mg, 0.3 mmol), 2-n-hexyl-4,7-dibromo-benzotriazole (157.5 mg, 0.3 mmol) ) and 10mL of toluene were respectively added to the two-necked bottle of 50mL, fully vented with nitrogen for about 20min, then added 15mg of bistriphenylphosphonium palladium dichloride, fully vented with nitrogen for about 10min, at 120°C ...

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Abstract

The invention belongs to the photoelectric material field, which discloses an organic semiconductor material containing benzotriazole group, preparation method thereof and organic solar cell. The organic semiconductor material containing benzotriazole group has a general structural formula, wherein R1 and R2 are C1-C20 alkyl group, and n is an integer of 10-50. The inventive organic semiconductor material containing benzotriazole group is prepared by polymerization of dithienyl benzotriazole and vinylcarbazole through Heck coupling, to broaden absorption bands of polycarbazole and improve sunlight utilization range of polycarbazole, so as to obtain better photovoltaic performance.

Description

technical field [0001] The invention belongs to the field of optoelectronic materials, in particular to a benzotriazole group-containing organic semiconductor material. The invention also relates to a preparation method of the benzotriazole group-containing organic semiconductor material and an organic solar cell using the benzotriazole group-containing organic semiconductor material. Background technique [0002] Solar energy is the most ideal alternative energy for human beings in the future, and solar cells that convert solar energy into electrical energy are also a research hotspot. In recent years, conjugated polymer thin film solar cells have emerged with low cost, light weight, simple fabrication process, and can be fabricated into flexible devices. etc. outstanding advantages. In addition, organic materials are diverse and highly designable, promising to improve the performance of solar cells through material design and optimization. [0003] Polycarbazole derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 周明杰王平张振华黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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