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Thiophene disilole, derivatives thereof and preparation method and use of thiophene disilole and derivatives thereof

A derivative, bisthiophene technology, applied in the application field of thienodithiophene and its derivatives, can solve the problems of difficulty in forming a plane, affecting the molecular band gap, etc., and achieve excellent carrier transport performance and solubility. Effect

Active Publication Date: 2011-12-21
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

α-thiophene (α-nT) and its derivatives have been widely used in organic field effect transistors (Katz, H.E.; Laquindanum, J.G.; Lovinger, A.J.Chem.Mater.1998, 10, 633. Ong, B.S.; Wu, Y.; Liu P.; Gardner, S.Adv.Mater.2005, 17, 1141), however, because the thiophene molecule is easy to bend, it is not easy to form a plane, thereby affecting the band gap of the molecule (Videlot-Ackermann, C.; Ackermann , J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Raynal, P.; El Kassmi, A.; , Z.; Gilat, S.L.Acc.Chem.Res.2001, 34, 359)

Method used

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  • Thiophene disilole, derivatives thereof and preparation method and use of thiophene disilole and derivatives thereof
  • Thiophene disilole, derivatives thereof and preparation method and use of thiophene disilole and derivatives thereof
  • Thiophene disilole, derivatives thereof and preparation method and use of thiophene disilole and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Si-methyldithiarolothiophene, its chemical structure is:

[0044]

[0045] The preparation method of above-mentioned Si-methyl dithiarolothiophene is as follows:

[0046] In a nitrogen atmosphere, 1 part of tetrabromothiophene solid product and 2.1 parts of trimethylsilylacetylene were dissolved in 300 parts of tetrahydrofuran, 60 parts of triethylamine, 0.05 part of bis(triphenylphosphine)palladium chloride, and 0.1 part of cuprous iodide , and stirred at reflux for 12 hours to obtain a dibromothiophene compound of trimethylsilylacetylene;

[0047] Dissolve 1 part of dibromothiophene compound of trimethylsilylacetylene in 300 parts of ether, cool to -78°C, add 2.5 mol / L n-hexane solution of butyllithium, and add 2.1 parts of dialkyl chloride after 1 hour Silane, warming up to room temperature, stirring for 24 hours to obtain a substituted thiophene compound of trimethylsilylacetylene and dialkylsilyl;

[0048] Dissolve 1 part of trimethylsilylacetylene and dialkyl...

Embodiment 2

[0051] Si-methyldithiarolodithiophene, its chemical structure is:

[0052]

[0053] The preparation method of above-mentioned Si-methyl dithiarodithiophene is as follows:

[0054] In a nitrogen atmosphere, 1 part of tetrabromodithiophene solid product and 2.1 parts of trimethylsilylacetylene were dissolved in 300 parts of tetrahydrofuran, 60 parts of triethylamine, 0.05 part of bis(triphenylphosphine) palladium chloride, 0.1 part of iodide Cuprous, refluxed and stirred for 12 hours, obtained the dibromodithiophene compound of trimethylsilylacetylene;

[0055] Dissolve 1 part of dibromodithiophene compound of trimethylsilylacetylene in 300 parts of ether, cool to -78°C, add 2.5 mol / L butyllithium in n-hexane, and add 2.1 parts of dioxane after 1 hour Chlorosilane, warming up to room temperature, stirring for 24 hours, to obtain trimethylsilyl acetylene and dialkylsilyl substituted dithiophene compound;

[0056] Dissolve 1 part of trimethylsilylacetylene and dialkylsilyl-di...

Embodiment 3

[0059] Si-methyldithiarolotrithiophene, its chemical structure is:

[0060]

[0061] The preparation method of above-mentioned Si-methyl dithiarolotrithiophene is as follows:

[0062] In a nitrogen atmosphere, 1 part of tetrabromotrithiophene solid product and 2.1 parts of trimethylsilylacetylene were dissolved in 300 parts of tetrahydrofuran, 60 parts of triethylamine, 0.05 part of bis(triphenylphosphine) palladium chloride, 0.1 part of iodide Cuprous, refluxed and stirred for 12 hours, obtained the dibromotrithiophene compound of trimethylsilylacetylene;

[0063] Dissolve 1 part of the dibromotrithiophene compound of trimethylsilylacetylene in 300 parts of ether, cool to -78°C, add 2.5 mol / L butyllithium in n-hexane, and add 2.1 parts of dioxane after 1 hour Chlorosilane, warming up to room temperature, stirring for 24 hours to obtain trimethylsilyl acetylene and dialkylsilyl substituted trithiophene compound;

[0064] Dissolve 1 part of trimethylsilylacetylene and dial...

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PUM

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Abstract

The invention discloses thiophene disilole and derivatives thereof and a preparation method of the thiophene disilole and derivatives thereof. The chemical structure of the thiophene disilole is shown below. In the structure, M may be thiophene, di-thiophene or tri-thiophene; and R may be alkyl, aryl, halo or hydrogen. The thiophene disilole and derivatives thereof have high current carrier transmitting performance and dissolving performance and have very important application values in the technical fields of donor materials of organic field-effect transistors and organic solar cells and the like.

Description

technical field [0001] The present invention relates to a thienodisilole and its derivatives, a preparation method of the thienodisilole and its derivatives, and an application of the thienodisilole and its derivatives. Background technique [0002] Since the first organic field effect transistor (OFET) was reported in 1986 (Tsumura, A.; Koezuka, H.; Ando, ​​T. Appl. Phys. Lett, 1986, 49, 1210), organic field effect transistors have achieved Great development. The advantages of organic field effect transistors are: simple preparation process, low cost, light weight and good flexibility. They can be used in smart cards, electronic trademarks, electronic paper, memory, sensors and active matrix displays. They are ideal for organic optoelectronic devices and circuits. key components. [0003] Thiophene compounds are an important class of organic semiconductor materials. α-thiophene (α-nT) and its derivatives have been widely used in organic field effect transistors (Katz, H....

Claims

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Application Information

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IPC IPC(8): C07F7/08C07F7/10H01L51/30H01L51/46C08G61/12
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 葛子义刘颖彭瑞祥欧阳新华杨峰张新业李敏
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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