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Soluble electro-green light organic molecule glass material and preparation method and use thereof

A technology of organic molecules and glass materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of high-resolution color display devices, achieve high film shape stability, convenient purification, and simple synthesis Effect

Inactive Publication Date: 2013-01-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, although multilayer electroluminescent devices prepared by vacuum thermal evaporation can achieve high efficiency, it is difficult to realize high-resolution color display devices.

Method used

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  • Soluble electro-green light organic molecule glass material and preparation method and use thereof
  • Soluble electro-green light organic molecule glass material and preparation method and use thereof
  • Soluble electro-green light organic molecule glass material and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, the preparation of 2-(4-isobutoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane:

[0040]

[0041] 4-isobutoxy-1-bromobenzene (4.5g, 19.65mmol) was dissolved in dried tetrahydrofuran (40mL), and n-butyllithium (2.5M, 7.86mL, 19.65mL) was added dropwise at -78°C mmol), in N 2 React under atmosphere for 1 hour, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (4.61mL, 19.65mmol) rapidly, and then gradually increase Reaction at room temperature for 8 hours. The reaction mixture was poured into water, and extracted with dichloromethane. The organic layer was washed with brine and washed with anhydrous MgSO 4 dry. After the solvent was removed under reduced pressure, it was separated with a silica gel column, and the eluent was petroleum ether to obtain a colorless transparent liquid.

Embodiment 2

[0042] Embodiment 2, the preparation of 4-bromo-7-(4-isobutoxyphenyl)-2,1,3-benzothiadiazole:

[0043]

[0044] 2-(4-isobutoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (3.1g, 11.2mmol), 4,7-di Bromo-2,1,3-benzothiadiazole (4.26g, 14.6mmol), toluene (70mL), ethanol (25mL), and 2M aqueous sodium carbonate solution (20mL) were added to a two-necked flask, and nitrogen gas was bubbled to exhaust for 30 minute. The catalyst tetrakis(triphenylphosphine)palladium (195mg, 0.168mmol) was quickly added into the reaction flask, and then heated to 70°C for reflux reaction for 36 hours. After the mixture was cooled, it was washed with distilled water and extracted three times with toluene and dichloromethane respectively, and the organic phase was extracted with MgSO 4dry. A yellow-green solid was obtained by column chromatography.

Embodiment 3

[0045] The preparation of embodiment 3,3,5-two (4-isobutoxyphenyl) bromobenzene:

[0046]

[0047] 2-(4-isobutoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.58g, 20.2mmol), s-tribromobenzene ( 3.03g, 9.63mmol), toluene (50mL), ethanol (20mL), and 2M sodium carbonate aqueous solution (20mL) were added into a two-necked flask, and nitrogen gas was bubbled to exhaust for 30 minutes. The catalyst tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) was quickly added into the reaction flask, and then heated to 90° C. for reflux reaction for 8 hours. After the mixture was cooled, it was washed with distilled water and extracted 3 times with dichloromethane, and the organic phase was washed with MgSO 4 After drying, a white solid was obtained by column chromatography. Example 4, 3,5-bis(4-isobutoxyphenyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaboryl)benzene preparation:

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Abstract

The invention discloses a soluble electroluminescent green light organic molecule glass material, a preparation method and applications thereof. The material comprises two types of a symmetric substituent benzothiadiazole derivative and a dissymmetric substituent benzothiadiazole derivative. The preparation method of the material comprises: carbazol and fluorine or anthracene are taken as raw materials, a bromide that contains Ar1 is obtained through palladium-catalyzed coupling reaction or cuprous salt catalyzed coupling reaction, and corresponding boric acid ester is generated through a next reaction; the boric acid ester is reacted with 4, 7-dibromo benzothiadiazole or a bromide of benzothiadiazole substituted by soluble resin Ar2 and a tiny molecule luminescent material which is symmetric or dissymmetric is obtained. The luminescent material prepared has good solubility in a solvent with high boiling point and weak polarity and can be purified by the solution method; simultaneously, the luminescent material has good thermal stability and morphologic stability, particularly the luminescent material with the dissymmetric structure has advantages in both synthesis and purification, thus having important application prospect in electroluminescence display, illumination and laser.

Description

technical field [0001] The invention relates to a novel soluble electro-green organic molecular glass material and a preparation method thereof, and also relates to the application of the molecular material in the preparation of light-emitting materials, light-emitting diodes, lasers and lighting devices. Background technique [0002] In 1987, Tang and VanSlyke of Kodak Corporation of the United States prepared a small molecule organometallic complex octahydroxyquinoline aluminum (Alq 3 ) as a "sandwich" (anode / luminescent layer / cathode) thin-film electroluminescent device as a light-emitting layer, creating a fundamental and applied research on electroluminescence with extremely small molecules. During the past two decades, organic light-emitting diodes (OLEDs) have attracted considerable attention due to their potential applications in next-generation display and lighting technologies. [0003] At present, the research and development of electroluminescent materials has e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/10C07D285/14C09K11/06H01L51/54
Inventor 朱旭辉李远黄菊曹镛
Owner SOUTH CHINA UNIV OF TECH
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