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Organic semiconductor material and preparation method and application thereof

An organic semiconductor and conjugation technology, applied in the field of organic semiconductor materials and their preparation, can solve problems such as low efficiency of organic solar cells, and achieve the effects of being beneficial to charge transport, good planarity and high yield

Active Publication Date: 2015-06-03
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Compared with inorganic semiconductor solar cells, the efficiency of organic solar cells is still low

Method used

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  • Organic semiconductor material and preparation method and application thereof
  • Organic semiconductor material and preparation method and application thereof
  • Organic semiconductor material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]Example 1, 4,4'-(2,6-dibromobenzo[1,2-B:4,5-B']dithiophene-4,8-diyl)bis(1-2-butyl Synthesis of octyl)-1H-1,2,3-triazole) (abbreviated as DBrTRI12)

[0043] The chemical reaction process is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:

[0044] Among them, (I) oxalyl chloride, dichloromethane, room temperature for 12 hours; (II) dimethylamine hydrochloride, triethyl, dichloromethane, room temperature for 12 hours; (Ⅲ) NBS, DMF, room temperature for 6 hours; (IV )-78°C, tetrahydrofuran, n-butyllithium, room temperature for 12 hours; (Ⅴ)-78°C, trimethylsilylacetylene, tetrahydrofuran, return to room temperature for 1 hour, then add anhydrous stannous chloride, 50°C, 12 hours; (VI) azidoalkyl chain, anhydrous potassium carbonate, cuprous iodide, tetrahydrofuran, water, acetonitrile, reflux.

[0045] (1) Dissolve 2,5-dibromothiophene-3-carboxylic acid dimethylamide (compound 3, 15.6g, 50mmol) synthesized according ...

Embodiment 2

[0051] Example 2, 4,4'-(2,6-dibromobenzo[1,2-B:4,5-B']dithiophene-4,8-diyl)bis(1-2-hexyldecane Synthesis of -1H-1,2,3-triazole) (abbreviated as DBrTRI16)

[0052] Synthetic method is consistent with embodiment 1. A light yellow powder (DBrTRI16, 1.7 g, 92%) was obtained.

[0053] The NMR data of the product are as follows: 1 H NMR (600MHz, CDCl 3 ),δ(ppm):8.05(s,2H).7.96(s,2H),4.44(d,4H),2.07(m,2H),1.36-1.25(m,48H),0.89-0.85(m, 12H). 13 C NMR (150MHz, CDCl 3 ), δ(ppm): 144.23, 138.49, 135.05, 126.10, 123.17, 118.15, 117.42, 54.38, 39.23, 31.88, 31.78, 31.46, 31.45, 29.89, 29.55, 29.54, 265.30, 26.369, 24.26 ,14.09.

Embodiment 3

[0054] Example 3, 4,4'-(2,6-dibromobenzo[1,2-B:4,5-B']dithiophene-4,8-diyl)bis(1-2-octyl) Synthesis of dodecyl)-1H-1,2,3-triazole) (abbreviated as DBrTRI20)

[0055] Synthetic method is consistent with embodiment 1. A pale yellow powder (DBrTRI20, 2.0 g, 95%) was obtained.

[0056] The NMR data of the product are as follows: 1 H NMR (600MHz, CDCl 3 ),δ(ppm):8.05(s,2H),7.96(s,2H),4.44(d,4H),2.07(m,2H),1.36-1.25(m,64H),0.89-0.85(m, 12H). 13 C NMR (150MHz, CDCl 3 ), δ(ppm): 144.26, 138.51, 135.07, 126.12, 123.14, 118.17, 117.43, 54.38, 39.23, 31.91, 31.88, 31.45, 29.88, 29.65, 29.63, 29.59, 29.54, 29.30, 26.26.29 ,22.65,14.11,14.09.

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Abstract

The invention discloses an organic semiconductor material. The organic semiconductor material contains a 4, 4'-bi-1H-1, 2, 3-triazolyl dibenzothiophene unit and an aromatic group which are connected by a conjugating manner. The invention further discloses a preparation method of the inorganic semiconductor material. The inorganic semiconductor material is prepared from a bialkynyl-containing dibenzothiophene monomer and an alkyl chain containing azide by click chemistry. Compared with the prior art, the organic semiconductor material is beneficial for pi-pi accumulation of molecules and enables good planarity of a polymer, and the performances of a device can be improved. The preparation method is simple and convenient, high in yield, simple in after-treatment, and convenient to purify.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic semiconductor material and its preparation method and application. Background technique [0002] In today's world, energy issues have become a common concern of all mankind. With the continuous consumption of non-renewable fossil energy and the deterioration of environmental pollution, people are eager to seek and develop and utilize various renewable clean energy. Among them, since solar energy is an inexhaustible and inexhaustible clean energy source, the research on solar cells that convert solar energy into electrical energy has been highly valued by various countries. In recent years, organic photovoltaic devices have become a research hotspot in solar cells due to their advantages of light weight, simple processing, low cost, and the ability to make large-area flexible devices. Among them, the highest energy conversion efficiency of singl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/12
Inventor 黄飞谢锐浩曹镛
Owner SOUTH CHINA UNIV OF TECH
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