Compound, polymer, polymer semiconductor material and organic thin film transistor

A compound and polymer technology, applied in semiconductor devices, tin organic compounds, semiconductor/solid-state device manufacturing, etc., can solve problems that limit the application of polymer semiconductor materials, achieve good solubility, improve conjugation, and high mobility Effect

Active Publication Date: 2012-09-19
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are few alternative heteroatom-containing fused-ring aromatic compounds for constructing high mobility, which limits the application of polymer semiconductor materials in organic thin film transistors.

Method used

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  • Compound, polymer, polymer semiconductor material and organic thin film transistor
  • Compound, polymer, polymer semiconductor material and organic thin film transistor
  • Compound, polymer, polymer semiconductor material and organic thin film transistor

Examples

Experimental program
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preparation example Construction

[0085] The invention provides a kind of preparation method of above-mentioned polymer, comprises the following steps:

[0086]Under the protection of an inert gas, the compound with the structure of formula (I) and the polymerized monomer will generate a polymer under the action of a catalyst and an auxiliary ligand; the polymerized monomer has the formula (XII), formula (XIII), formula (XIV ), formula (XV), formula (XVI), formula (XVII), formula (XVIII), formula (XIX) or formula (XX) structure;

[0087]

[0088] Among them, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 Each independently is an alkyl group, preferably C 12 ~C 30 of alkyl. The R 3 preferably C 12 ~C 30 straight chain alkyl or C 12 ~C 30 branched chain alkyl; the R 4 , R 5 and R 6 each independently preferably C 12 ~C 30 branched chain alkyl.

[0089] In the present invention, when preparing the polymer, under the protection of an inert gas, the compound having ...

Embodiment 1

[0136] Embodiment 1N-dodecyl-2,7-dibromo-3,6-two (methylthio) carbazole synthesis

[0137] Add 9.2mmol dimethyl sulfide to 20mL dichloromethane solution containing 9.2mmol trifluoromethanesulfonic anhydride, stir at -40°C for 15 minutes, then add dropwise 40mL containing 4.4mmol N-dodecyl -2,7-Dibromocarbazole in dichloromethane, stirred at -40°C for 2 hours and then at room temperature for 3 hours, and the solvent was removed in vacuo. Then add 44mL acetonitrile to the system, add 22mmol triethylamine dropwise at 0°C, stir at room temperature for 3 hours, remove the solvent in vacuo, and purify by silica gel column chromatography, the eluent is a mixed solution of dichloromethane and petroleum ether, dichloromethane The volume ratio of methane to petroleum ether was 1:4, and finally a solid, N-dodecyl-2,7-dibromo-3,6-bis(methylthio)carbazole, was obtained with a yield of 53.0%. The structural characterization data are as follows: 1 H NMR (300MHz, CDCl3): δ (ppm) 7.92 (s, 2H...

Embodiment 2

[0138] Example 2 Preparation of N-dodecyl-2,7-bis(trimethylsiliethynyl)-3,6-bis(methylthio)carbazole

[0139] Under argon atmosphere, add 2.1mmol N-dodecyl-2,7-dibromo-3,6-bis(methylthio)carbazole, 72mg bis(triphenylphosphine)palladium dichloride (Pd (PPh 3 ) 2 Cl 2 ), 39mg of cuprous iodide (CuI), and 20mL of triethylamine were slowly added dropwise with 4.53mmol of trimethylsilylacetylene, stirred at room temperature for 28 hours, washed with ethyl acetate, collected the organic phase, and washed with saturated ammonium chloride solution Wash the organic phase twice with saturated saline, dry over anhydrous magnesium sulfate, remove the solvent, and purify with silica gel column chromatography. The eluent is a mixed solution of dichloromethane and petroleum ether. The volume ratio of dichloromethane to petroleum ether is The ratio is 1:4, and finally a solid is obtained, that is, N-dodecyl-2,7-bis(trimethylsilylethynyl-3,6-bis(methylthio)carbazole, the yield is 70.0%, and...

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Abstract

The invention provides a compound in a formula (I) structure and a polymer in a formula (II) structure. A preparation method of the polymer in the formula (II) structure provided by the invention is characterized in that under the inert gas protection, the compound in the formula (I) structure and polymerization monomers generate the polymer under the effects of catalysts and auxiliary ligands. The invention also provides an organic thin film transistor and a polymer semiconductor material consisting of the polymer, wherein a charge transmission layer of the organic thin film transistor is made of the polymer semiconductor material. The polymer in the formula (II) structure has a good linear structure, and the conjugate degree of the polymer is improved, so the polymer semiconductor material formed by the polymer is enabled to have a better migration rate. The polymer of the compound based on N and S two-kind heteroatoms provided by the invention has good solubility in organic solvents.

Description

technical field [0001] The invention relates to the field of semiconductor materials, in particular to compounds, polymers, polymer semiconductor materials and organic thin film transistors. Background technique [0002] Organic thin film transistors are field effect transistors that use organic semiconductor materials as the active layer. The manufacturing process of organic thin film transistors is simple, the cost is low, and it is easy to prepare flexible large-area devices. The core of an organic thin film transistor is an organic semiconductor material. [0003] In the mid-1980s, scientists from various countries began to try to use organic semiconductor materials to make organic thin-film crystals, but the mobility of the first organic thin-film transistor made of organic semiconductor materials was less than 10 -5 cm 2 / V·s. In organic semiconductor materials, the weak van der Waals interaction between adjacent molecules is the main reason for limiting the mobili...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14C07F7/22C07D519/00C08G61/12H01L51/30
Inventor 耿延候陈亚刚邓云峰田洪坤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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