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Aromatic enediyne derivatives, organic semiconductor thin films using the same and manufacturing methods thereof, and electronic devices incorporating such films

A technology of aromatic enediynes and derivatives, which is applied in semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., and can solve problems such as the high price of pentacene and the inapplicability of preparing organic semiconductor films.

Inactive Publication Date: 2007-05-30
SAMSUNG ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the use of low molecular weight compounds such as pentacene is expensive and generally not suitable for the preparation of organic semiconducting films on large area substrates to produce price sensitive products

Method used

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  • Aromatic enediyne derivatives, organic semiconductor thin films using the same and manufacturing methods thereof, and electronic devices incorporating such films
  • Aromatic enediyne derivatives, organic semiconductor thin films using the same and manufacturing methods thereof, and electronic devices incorporating such films
  • Aromatic enediyne derivatives, organic semiconductor thin films using the same and manufacturing methods thereof, and electronic devices incorporating such films

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0065] Preparation Example 1: Synthesis of Arenediyne Derivative A Example

[0066]

[0067] 2ml (18.0mmol) of 2,3-dibromothiophene and 3.5ml (27.0mmol) of 1-heptyne were mixed with tetrahydrofuran / diisopropylamine (1:1) solvent, and 0.23g (0.36mmol) of dichloro Diphosphine palladium, 70 mg (0.36 mmol) of copper iodide and 0.1 g (0.36 mmol) of triphenylphosphine were subsequently added thereto. The reaction solution was heated at 70°C for 8 hours, and then washed with an aqueous ammonium chloride solution. The obtained organic layer was dried over magnesium sulfate, dried under reduced pressure, and purified by silica gel column chromatography, thereby obtaining 4.6 g of 2-heptynyl-3-bromothiophene. 3.3 ml (23.2 mmol) of trimethylsilylacetylene was added to the compound obtained above, and then it was returned to the above synthesis process to prepare 2.7 g (9.84 mmol) of 2-heptynyl-3-trimethylmethyne The silylethynylthiophene was then mixed with 12.8 ml (12.8 mmol) lithi...

preparation Embodiment 2

[0070] Preparation Example 2: Synthesis of Arenediyne Derivative B Example

[0071]

[0072] 0.25 g (1 mmol) of tetrathiophene (terthiophene) was added to chloroform, and 0.35 g (2.0 mmol) of N-bromosuccinimide was added thereto, thereby obtaining dibromide 1b, which was then mixed with synthetic derivatives A derivative B was obtained by Suzuki coupling and desilylation reaction under the same synthesis conditions. Analyzing the prepared derivative B obtains the following NMR data: 1 H NMR (300MHz, CDCl 3 ), δ(ppm) 0.93(t, 6H, J=7.2Hz), 1.24-1.67(m, 12H), 2.51(t, 4H, J=7.0Hz), 3.26(s, 2H), 7.05-7.08( m, 8H).

preparation Embodiment 3

[0073] Preparation Example 3: Synthesis of Arenediyne Derivative C Example

[0074]

[0075] 2,2'-Dibromodithiophene and 2-bromothiophene are subjected to Suzuki coupling, thereby obtaining the intended or desired product, to which N-bromosuccinimide is then added to prepare dibromotetrathiophene 1c. Subsequently, the compound 1c was subjected to Suzuki coupling and desilylation reaction under the same synthesis conditions as for the synthesis of derivative A, whereby derivative C was obtained. The derivative C prepared by analysis obtains the following NMR data: 1 H NMR (300MHz, CDCl 3 ), δ(ppm) 0.93(t, 6H, J=7.2Hz), 1.24-1.67(m, 12H), 2.51(t, 4H, J=7.0Hz), 3.27(s, 2H), 7.05-7.09( m, 10H).

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Abstract

Disclosed are aromatic enediyne derivatives, methods of manufacturing organic semiconductor thin films from such aromatic enediyne derivatives, and methods of fabricating electronic devices incorporating such organic semiconductor thin films. Aromatic enediyne derivatives according to example embodiments provide improved chemical and / or electrical stability which may improve the reliability of the resulting semiconductor devices. Aromatic enediyne derivatives according to example embodiments may also be suitable for deposition on various substrates via solution-based processes, for example, spin coating, at temperatures at or near room temperature to form a coating film that is then heated to form an organic semiconductor thin film. The availability of this reduced temperature processing allows the use of the aromatic enediynes derivatives on large substrate surfaces and / or on substrates not suitable for higher temperature processing. Accordingly, the organic semiconductor thin films according to example embodiments may be incorporated in thin film transistors, electroluminescent devices, solar cells, and memory devices.

Description

technical field [0001] The present invention relates to an aromatic enediyne derivative, an organic semiconductor thin film formed using the aromatic enediyne derivative and a method for producing the film, an electronic device including the organic semiconductor thin film and a method for producing the device, and also relates to, for example , organic semiconducting thin films fabricated from arylediyne derivatives that exhibit improved chemical and electrical stability. The aromatic enediyne derivatives of the present invention can be coated on a substrate by a solution-based method such as spin coating, and it is also suitable for coating at room temperature or a temperature close to room temperature to form a coating film, and the coating film after heat treatment An organic semiconductor thin film can be formed on a substrate, which can be used to form a carrier transport layer in an electronic device including the organic semiconductor thin film. Background technique ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/18H01L51/00H01L51/30H01L51/40H01L51/46H01L51/48H01L51/54H01L51/56H10K99/00
CPCY02E10/549C07D333/08H10K85/655
Inventor 郑银贞文炫植韩国珉
Owner SAMSUNG ELECTRONICS CO LTD
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