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Pyrrolopyrrole organic semiconductor material containing free radicals, preparation method and application thereof

A technology of pyrrolopyrrole and organic semiconductors, which is applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., and can solve problems such as complex and cumbersome manufacturing processes, error detection results, and wide response bands

Active Publication Date: 2019-07-23
UNIV OF ELECTRONICS SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The object of the present invention is to provide a free radical-containing pyrrolopyrrole organic semiconductor material, preparation method and application thereof, so as to solve the problem of wide response band of inorganic semiconductor optoelectronic materials in the existing narrow-band detection technology, complex and cumbersome production process, and detection problems. The problem of errors in the results

Method used

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  • Pyrrolopyrrole organic semiconductor material containing free radicals, preparation method and application thereof
  • Pyrrolopyrrole organic semiconductor material containing free radicals, preparation method and application thereof
  • Pyrrolopyrrole organic semiconductor material containing free radicals, preparation method and application thereof

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Embodiment 1

[0096] The preparation method of this example is carried out according to the above reaction scheme I. In the structural formula of the halogenated pyrrolopyrrole derivatives used, R 4 Is 2-octane dodecyl; R 5 is an oxygen atom, R 6 For furan; X is Br. In the structural formula of monomer I, R 1 is tert-butyl; R 2 is tert-butyl; R 3 is hydroxyl; R 7 For 1,3,2-dioxaborol, 4,4,5,5-tetramethyl.

[0097] The preparation method of the free radical-containing pyrrolopyrrole organic semiconductor material in this embodiment includes:

[0098] (1) Add pyrrolopyrrole halogenated derivatives, monomer I, tetrakis (triphenylphosphine) palladium, tris (o-methylphenyl) phosphine, tetrabutylammonium hydroxide and water, in an inert gas atmosphere at 120 Condensation and reflux reaction in toluene solvent at the reaction temperature of °C for 12 hours to obtain pyrrolopyrrole-based organic semiconductor materials. Among them, the molar ratio between pyrrolopyrrole halogenated derivati...

Embodiment 2

[0101] The preparation method of this example is carried out according to the above reaction scheme I, and the pyrrolopyrrole halogenated derivatives used in the structural formula R 4 Is 2-octane dodecyl; R 5 is an oxygen atom; R 6 For thiophene; X is Br. In the structural formula of monomer I, R 1 is tert-butyl; R 2 is tert-butyl; R 3 is hydroxyl; R 7 For 1,3,2-dioxaborol, 4,4,5,5-tetramethyl.

[0102] The preparation method of the free radical-containing pyrrolopyrrole organic semiconductor material in this embodiment includes:

[0103] (1) Add pyrrolopyrrole halogenated derivatives, monomer I, tetrakis (triphenylphosphine) palladium, tris (o-methylphenyl) phosphine, tetrabutylammonium hydroxide and water, in an inert gas atmosphere at 120 Condensation and reflux reaction in toluene solvent at the reaction temperature of °C for 12 hours to obtain pyrrolopyrrole-based organic semiconductor materials. Among them, the molar ratio between pyrrolopyrrole organic semicond...

Embodiment 3

[0106] The preparation method of this example is carried out according to the above reaction scheme I. In the structural formula of the halogenated pyrrolopyrrole derivatives used, R 4 Is 2-octane dodecyl; R 5 is an oxygen atom; R 6 For selenophene; X is Br. In the structural formula of monomer I, R 1 is tert-butyl; R 2 is tert-butyl; R 3 is hydroxyl; R 7 For 1,3,2-dioxaborol, 4,4,5,5-tetramethyl.

[0107] The preparation method of the free radical-containing pyrrolopyrrole organic semiconductor material in this embodiment includes:

[0108] (1) Add pyrrolopyrrole halogenated derivatives, monomer I, tetrakis (triphenylphosphine) palladium, tris (o-methylphenyl) phosphine, tetrabutylammonium hydroxide and water, in an inert gas atmosphere at 120 Condensation and reflux reaction in toluene solvent at the reaction temperature of °C for 12 hours to obtain pyrrolopyrrole-based organic semiconductor materials. Among them, the molar ratio between pyrrolopyrrole halogenated de...

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Abstract

The invention discloses a pyrrolopyrrole organic semiconductor material containing free radicals, a preparation method and application thereof and belongs to the technical field of photoelectric materials. The preparation method comprises the following steps: mixing a pyrrolopyrrole halogenated derivative with a monomer I, or mixing a pyrrolopyrrole organic tin compound and a monomer I' to obtaina pyrrolopyrrole organic semiconductor material; enabling the pyrrolopyrrole organic semiconductor material to react with an oxidant to obtain the pyrrolopyrrole organic semiconductor material containing the free radicals. The preparation method disclosed by the invention is simple in synthesis routine and easy in synthesis. The pyrrolopyrrole organic semiconductor material containing the free radicals prepared by the invention has the advantages that the electron mobility is high, the molecular stability is good, the absorption intensity is high, the absorption waveband is narrow, the absorption wavelength reaches a near-infrared waveband, and the pyrrolopyrrole organic semiconductor material containing the free radicals can be used as a free-radical material of devices such as near-infrared and narrowband photoelectric detectors and organic field effect transistors.

Description

technical field [0001] The invention relates to the technical field of optoelectronic materials, in particular to a free radical-containing pyrrolopyrrole organic semiconductor material, a preparation method and an application thereof. Background technique [0002] Optical detection technology can realize accurate detection from the ultraviolet visible light region to the infrared light region, and is often used in industrial production, military scientific research, optoelectronics and other fields. With the development of society, people have higher and higher requirements for optical detection technology. Therefore, in addition to the research on widening the detectable wavelength band, attention should also be paid to the development of narrow-band detection. Narrowband detectors, also known as band-distinguishing detectors, have wavelength sensitivity and can only detect light in specific wavelength bands, which play an important role in biological imaging and security ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04H01L51/46
CPCC07D487/04H10K85/649H10K85/653H10K85/655H10K85/6572
Inventor 郑永豪王文翔苗芳葛玲兵
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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