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2-(2'-hydroxyphenyl) benzoxazole compound containing substituent at 4-site and preparation method and application thereof

A technology of hydroxyphenyl and benzoxazole, applied in the field of organic semiconductor optoelectronics, can solve the problems of high production cost, complex preparation process, poor repeatability, etc., and achieve the effects of large Stokes shift, simple synthesis and high yield

Inactive Publication Date: 2017-05-31
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the technical problems such as complex device preparation process, high production cost and poor repeatability in current white light organic light-emitting diodes, the present invention provides a new organic fluorescent material, that is, 2-(2 '-Hydroxyphenyl) benzoxazole compound, its preparation method and application

Method used

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  • 2-(2'-hydroxyphenyl) benzoxazole compound containing substituent at 4-site and preparation method and application thereof
  • 2-(2'-hydroxyphenyl) benzoxazole compound containing substituent at 4-site and preparation method and application thereof
  • 2-(2'-hydroxyphenyl) benzoxazole compound containing substituent at 4-site and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0037] First, the preparation of 2-(2'-4-bromophenol)benzothiazole:

[0038] Get diaminophenol (4.4g, 20mmol, 1equiv) and p-aminobenzoic acid (2.5g, 20mmol, 1equiv) and add in 130ml polyphosphoric acid, in N 2 Heated to 168°C in an ambient environment, and refluxed for 6 hours. After the reaction was complete, the product was dissolved in 100 ml of ice-water mixture after cooling, and saturated NaOH aqueous solution was added thereto for neutralization. When the pH value is adjusted to about 6, add NaHCO 3 , while adding and stirring until there is no more CO 2 Bubbles are generated. The neutralized solution was left to stand until the solution was clarified and then suction filtered. Add the filtered solid to saturated NaHCO 3 The aqueous solution was extracted three times with ethyl acetate, the combined organic layers were washed with anhydrous Na 2 SO 4 After drying and rotary evaporation, 5 g of green product was obtained with a yield of 83%. (In the following exa...

Embodiment 2

[0043]Preparation of 2-(2'-benzothiazole)-4-(9'-phenanthrene)phenol

[0044] (1) Borylation of compounds containing aromatic hydrocarbon conjugated structures: under the protection of nitrogen, 9-bromophenanthrene was dissolved in dry tetrahydrofuran, placed in a dry ice acetone bath and cooled to -78°C, and n-butyllithium was added at low temperature, 9 -The addition ratio of phenanthrene bromide and n-butyllithium is 1:1.2. After stirring for 3 hours, add n-butyl borate, borate, continue the reaction for 0.5 hours, remove the dry ice acetone bath, heat up to room temperature and react for 18 hours. After the reaction was completed, the reaction was quenched in an ice-water bath, and then the organic phase was extracted with water and dichloromethane, and the organic phases were combined, dried and spin-dried to obtain the product.

[0045] (2) Take 9-phenanthrene borate (0.18g, 0.75mmol, 1 equivalent) and 2-(2'-4-bromophenol) benzothiazole (0.24g, 0.75mmol, 1 equivalent) and...

Embodiment 3

[0048] Preparation of 2-(2'-benzothiazole)-4-(1'-pyrene)phenol

[0049] 9-phenanthrene borate in embodiment 2 is changed into 1-pyrene borate, and concrete steps are:

[0050] (1) Borylation of compounds containing aromatic hydrocarbon conjugated structures: under the protection of nitrogen, 1-bromopyrene was dissolved in dry tetrahydrofuran, placed in a dry ice acetone bath and cooled to -78 ° C, and n-butyllithium was added at low temperature, 1 - The addition ratio of bromopyrene and n-butyllithium is 1:1.2. After stirring for 3 hours, add n-butyl borate, borate, continue the reaction for 0.5 hours, remove the dry ice acetone bath, heat up to room temperature and react for 18 hours. After the reaction was completed, the reaction was quenched in an ice-water bath, and then the organic phase was extracted with water and dichloromethane, and the organic phases were combined, dried and spin-dried to obtain the product.

[0051] (2) Take 9-pyrene borate (0.6g, 2.2mol, 1 equival...

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Abstract

The invention belongs to the technical field of organic semiconductor photoelectricity, and provides a 2-(2'-hydroxyphenyl) benzoxazole compound containing substituent at 4-site and a preparation method and application thereof. The general formula of the 2-(2'-hydroxyphenyl) benzoxazole compound containing the substituent at the 4-site is as shown in description, wherein X is S, O or NH, Ar is an aromatic hydrocarbon-containing conjugated structure unit. The compound is prepared from 2-(2'-4-bromophenol) benzoxazole and a polycyclic aromatic hydrocarbon compound containing bromine through Suzuki reaction. The compound disclosed by the invention has a four energy level transition fluorescence property of excited-state molecular proton transfer compound, can be used as a luminescent material, and can be applied to an organic white-light diode device. The compound disclosed by the invention has the advantages of being large in Stokes shift, good in luminescent quantum efficiency, simple in preparation, and high in synthetic yield.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor optoelectronics, and in particular relates to a 2-(2'-hydroxyphenyl) benzoxazole compound containing a substituent at the 4-position and its preparation and application. Background technique [0002] In 1987, C.W.Tang and others in the United States invented a multi-layered organic light-emitting diode (OLED) by vacuum evaporation, which made the research on organic electroluminescent devices highly valued by scientists from all over the world. The development of OLED technology has produced earth-shaking changes in the field of optoelectronic display. Nowadays, the development of material science and the maturity of theory and technology play a vital role in the development of new OLEDs, making researchers in the field of materials have great interest in the exploration of luminescent materials. White organic light-emitting diodes (WOLEDs) have excellent properties such as high eff...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06H01L51/54
CPCC09K11/06C07D277/66C09K2211/1037H10K85/657
Inventor 钱妍方启运檀康明
Owner NANJING UNIV OF POSTS & TELECOMM
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