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

An organic semiconductor and benzotriazole-based technology, which is applied in the field of organic solar cells and organic semiconductor materials, can solve the problems of insufficient sunlight absorption and low utilization rate of sunlight, and achieve broadening of the absorption band, improvement of utilization rate, and good The effect of photovoltaic performance

Active Publication Date: 2015-09-23
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

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preparation example Construction

[0031] The method for preparing a benzotriazole group-containing organic semiconductor material according to an embodiment includes the following steps:

[0032] Step S1: Provide compound A and compound B of the following structural formulas:

[0033]

[0034] Among them, in compound A, R 1 Is C 1 ~C 20 的alkyl; In compound B, R 2 Is C 1 ~C 20 的alkyl;

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

[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:

[0038]

[0039] Preferably, the preparation meth...

Embodiment 1

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

[0053]

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

[0055] Step 1. 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, dissolve the compound 2-octyl-4,7-dithiophene-1,2,3-benzotriazole (2.37g, 6mmol) in chloroform (60mL) and glacial acetic acid (60 mL) of the mixed solution, moved to an ice bath, and then N-bromosuccinimide (2.35 g, 13.2 mmol) was added to it in batches, and reacted at room temperature for 12 hours to obtain a reaction mixture.

[0058] The reaction mixture was extracted with dichloromethane three times and then washed with water, the organic p...

Embodiment 2

[0067] The benzotriazole group-containing organic semiconductor material of this embodiment 2, namely poly{3,6-divinyl-N-dodecylcarbazole-2-hexyl-4,7-dithiophene-1,2 , 3-benzotriazole} (where R 1 Dodecyl, R 2 Is hexyl, n is 32), and its structural formula is as follows:

[0068]

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

[0070] Step 1. The difference from Step 1 in Example 1 is that hexyl replaces octyl;

[0071] Step 2. 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 protection, 3,6-Divinyl-N-dodecylcarbazole (116mg, 0.3mmol), 2-n-hexyl-4,7-dibromo-benzotriazole (157.5mg, 0.3mmol) ) And 10mL of toluene were added to a 50mL two-necked flask, after fully ventilating with nitrogen for about 20 minutes, then 15mg of bistriphenylphosphonium dichloride was added to it, and then fully vented with nitrogen for about 10 minutes, at 120℃ The ...

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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, and specifically relates to an organic semiconductor material containing a benzotriazole group. 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 source for mankind in the future. Solar cells that convert solar energy into electrical energy are also a research hotspot. Conjugated polymer thin-film solar cells that have emerged in recent years have low cost, light weight, simple manufacturing processes, and can be made into flexible devices. And other outstanding advantages. In addition, there are many types of organic materials and strong designability. It is hoped that the performance of solar cells can be improved through material design and optim...

Claims

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Application Information

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Patent Type & Authority Patents(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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