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Oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and purpose thereof

A technology of conjugated molecules and oxygen group elements, applied in electrical components, photovoltaic power generation, circuits, etc., can solve problems such as poor stability, strong absorption in the visible light region, and restrictions on the development of displays, and achieve good solubility and high carrier migration rate effect

Active Publication Date: 2015-02-25
ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Among the organic semiconductor materials used in organic field effect transistors, pentacene has good film-forming properties and high mobility, but its stability is poor and its absorption in the visible light region is strong, which limits its development in the field of displays.
Researcher Liu Yunxi and academician Zhu Daoben of the Institute of Chemistry, Chinese Academy of Sciences synthesized pentathiophene with thiophene as its structural unit. It has better semiconductor performance and higher stability than pentacene, but its synthesis steps are more complicated.

Method used

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  • Oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and purpose thereof
  • Oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and purpose thereof
  • Oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and purpose thereof

Examples

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Effect test

example 1

[0043] Preparation of:

[0044] At -78°C, add 1 part of 3-bromofuran into anhydrous THF, add 1 part of BuLi dropwise, stir for 0.5-3 hours, and then move to room temperature. Add 1 to 2.0 parts of dimethyl disulfide to the above mixture, stir for 10 to 24 hours, quench with saturated ammonium chloride, extract with dichloromethane, dry and spin dry, and pass through a column to obtain 3-thiomethylfuran.

[0045] At 0°C, add 1 part of 3-thiomethylfuran into dichloromethane, add 1 part of bromine, stir for 2.5-5.0 hours, add saturated NaHSO 3 Or sodium thiosulfate solution, extract the organic phase and dry it, and pass through the column to obtain 2-bromo-3-thiomethylfuran

[0046] Take 2.2-3.0 parts of 2-bromo-3-thiomethylfuran and add it to THF, 2 Or add 2 to 10% Pd(PPh under the protection of Ar 3 ) 4 , Heated to reflux for 24 ~ 48h. The THF was spun out, the organic phase was extracted and dried, and passed through the column to obtain 2,5-(2-(3-thiomethyl)furan)fura...

example 2

[0049] Preparation of:

[0050] At -78°C, add 1 part of 3-bromothiophene to anhydrous THF, add 1 part of BuLi dropwise, stir for 0.5-3 hours, and then move to room temperature. Add 1 to 2.0 parts of dimethyl disulfide to the above mixture, stir for 10 to 24 hours, quench with saturated ammonium chloride, extract with dichloromethane, dry and spin dry, and pass through a column to obtain 3-thiomethylthiophene.

[0051] At 0°C, add 1 part of 3-thiomethylthiophene to dichloromethane, add 1 part of bromine, stir for 2.5-5.0 hours, add saturated NaHSO 3 Or sodium thiosulfate solution, extract the organic phase, dry and spin dry, and pass through the column to obtain 2-bromo-3-thiomethylthiophene.

[0052] Take 2.2-3.0 parts of 2-bromo-3-thiomethylthiophene and add it to THF, 2 Or add 2 to 10% Pd(PPh under the protection of Ar 3 ) 4 , Heated to reflux for 24 ~ 48h. The THF was spun out, and the organic phase was obtained by extraction, which was dried and spin-dried, and pass...

example 3

[0055] Preparation of:

[0056] At -78°C, add 1 part of 3-bromoselenophene to anhydrous THF, add 1 part of BuLi dropwise, stir for 0.5-3 hours and then move to room temperature. Add 1 to 2.0 parts of dimethyl disulfide to the above mixture, stir for 10 to 24 hours, quench with saturated ammonium chloride, extract with dichloromethane, dry and spin dry, and pass through a column to obtain 3-thiomethylthiophene.

[0057] At 0°C, add 1 part of 3-thiomethylselenophene to dichloromethane, add 1 part of bromine, stir for 2.5-5.0 hours, add saturated NaHSO 3 Or sodium thiosulfate solution, the organic phase was extracted and dried, and passed through the column to obtain 2-bromo-3-thiomethylselenophene.

[0058] Take 2.2-3.0 parts of 2-bromo-3-thiomethylselenophene and add it to THF, 2 Or add 2-10% Pd(PPh under the protection of Ar 3 ) 4, heating to reflux for 24 to 48 hours. The THF was spun out, the organic phase was extracted and dried, and passed through the column to obtai...

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Abstract

The invention relates to an oxygen family element-containing penta-condensed ring conjugated molecule and its derivative synthetic method and a purpose thereof. A structure of the oxygen family element-containing penta-condensed ring conjugated molecule is shown as follows, and a structure of the derivative of the oxygen family element-containing penta-condensed ring conjugated molecule is shown as follows.

Description

technical field [0001] The invention relates to a method for synthesizing the pentacondensed ring conjugated molecules containing oxygen group elements and derivatives thereof, as well as the application of the pentacondensed ring conjugated molecules containing oxygen group elements and the derivatives thereof. Background technique [0002] Field-effect transistors have been widely used as the most important unit device in microelectronics. In 1986, Tsumura, A, etc. (Tsumura, A.; Koezuka, H.; Ando, ​​T.Appl. 1210) reported a new field effect transistor - organic field effect transistor (OFET). Subsequently, organic field effect transistors are widely used in smart cards, electronic trademarks, The applications of electronic paper, memory, sensor and active matrix display have been extensively researched by many scientific researchers. [0003] Among the organic semiconductor materials used in organic field effect transistors, pentacene has good film-forming properties and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D517/22H01L51/54H01L51/46H01L51/30
CPCC07D495/22C07D517/22H10K85/6576H10K85/657Y02E10/549
Inventor 葛子义刘其达
Owner ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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