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Organic semiconductor material, its preparation method and application

An organic semiconductor, coupling reaction technology, applied in the fields of semiconductor/solid-state device manufacturing, semiconductor devices, luminescent materials, etc., can solve the problems of molecular structure changes, affecting the stability and performance of devices, and achieve large modification space and flexible synthesis routes. , the effect of good solution processability

Active Publication Date: 2015-12-23
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, this type of material is prone to photochemical reactions, resulting in changes in the molecular structure, which affects the stability and performance of the device.

Method used

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  • Organic semiconductor material, its preparation method and application
  • Organic semiconductor material, its preparation method and application
  • Organic semiconductor material, its preparation method and application

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preparation example Construction

[0053] As one of the more preferred embodiments, the preparation method may include:

[0054] Direct halogenation of 2,6-dialkylnaphthalene followed by a transition metal-catalyzed coupling reaction yielded a 1,5-diarylnaphthalene-based compound containing a phenolic hydroxyl group, followed by microwave-assisted synthesis of o-dichlorobenzene The organic semiconductor material is obtained by performing a ring-closing reaction as a solvent.

[0055] In the present invention, the aromatic group Ar is used as a bridge, and the active group is introduced into the reactive site on the Ar group to solve the solubility and chemical modification problems of this type of compound and expand the reactivity of the structure of this type of compound. According to the application, a series of oxygen-bridged 1,5-diarylnaphthalene-based optoelectronic materials can be obtained, which can be widely used in the fields of organic electronics such as organic electroluminescence, organic field e...

Embodiment 1 2

[0059] The preparation process of embodiment 1 dioxaanthanthrene, comprising:

[0060] Preparation of A, 2,2'-(1,5-naphthyl)diphenol (compound a)

[0061]

[0062] In a 250mL two-neck round bottom flask, add 3g of 1,5-dibromonaphthalene, 5g of 2-hydroxyphenylboronic acid, 0.6g of tetrakistriphenylphosphopalladium, 5.8g of potassium carbonate, 60mL of toluene and 6mL of water. The system was degassed with a vacuum pump for half an hour, and then filled with nitrogen. The reaction was refluxed overnight, and the solution was cooled to room temperature after the reaction was terminated. The organic phase was collected by liquid separation through a separatory funnel, the aqueous phase was extracted three times with ethyl acetate, and the organic phases were combined. Dry with anhydrous sodium sulfate, filter, spin dry the solvent, and separate by column chromatography to obtain a white solid with a yield of 85%. 1 HNMR (CDCl 3 , 500MHz): δ=7.68(d, 2H), 7.49-7.44(m, 4H), 7....

Embodiment 23

[0066] Embodiment 23, the preparation method of 10-diphenyldioxaanthanthrene, comprising:

[0067] The preparation of A, 1,5-two (pinacol borate) naphthalene:

[0068]

[0069] Dissolve 6.86g of 1,5-dibromonaphthalene in 100mL of anhydrous N,N-dimethylformamide, then add 18.3g of biboronic acid pinacol ester, 1.75g ​​of [1,1'-bis(diphenylphosphine Base) ferrocene] palladium dichloride and 9.42g potassium acetate. The system was reacted overnight at 90°C under the protection of nitrogen, and poured into ice water after the reaction was terminated. The precipitate was filtered off, washed with ethanol, and dried in vacuo to give a white solid with a yield of 88%. 1 HNMR (CDCl 3 , 500MHz): δ=8.89(d, 2H), 8.07(d, 2H), 7.52(t, 2H), 1.42(s, 24H).

[0070] The preparation of B, 2-bromo-4-phenylphenol:

[0071]

[0072] 7.63g of 4-phenylphenol was dissolved in 50mL of chloroform, and then 10mL of chloroform dissolved in 2.63mL of liquid bromine was added dropwise. The syst...

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Abstract

The invention discloses a novel organic semiconductor material, a preparation method, and applications thereof. The organic semiconductor has a structural formula, which is represented in the description. The preparation method comprises the following steps: taking naphthalene or derivatives containing a naphthalene structure as the primary raw material, orderly subjecting the primary raw material to 1st and 5th position functionalization reactions, then subjecting the reaction product to carry out coupling reactions with aromatic groups so as to obtain a compound, which contains a phenolic hydroxyl group and takes 1,5-diaryl naphthalene as the core, and then subjecting the compound to carry out ring-closure reactions so as to obtain the novel organic semiconductor material. The novel organic semiconductor material has a good environmental stability and a photoelectric performance, at the same time, has a very good solution processing performance, is easy to prepare and carry out a post modification treatment, and can be widely applied to fields of various semiconductor electronic and photoelectric devices such as organic light emitting diodes, organic thin film transistors, organic light sensors, and the like.

Description

technical field [0001] The invention relates to an organic semiconductor material and its preparation method and application, in particular to an organic semiconductor material containing oxygen bridges and having 1,5-diarylnaphthalene as the main skeleton and its preparation method, belonging to the technology of organic photoelectric materials field. Background technique [0002] Organic electronic materials have the characteristics of rich types, cheap raw materials, adjustable molecular properties through chemical composition modification, light, thin, and flexible products, especially materials that can be processed by solution and can be printed to achieve roll-to-roll large-area, Low-cost manufacturing has attracted much attention from the industry. Since the first report of organic small molecule thin film electroluminescent devices in 1987, organic flat panel display technology has made great progress and has become the next generation of marketable products to rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07D495/22C09K11/06H01L51/54
Inventor 邱松周春山吕娜崔铮
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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