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Novel anthracene luminescent material, preparation method, and applications thereof

A luminescent material, anthracene technology, applied in the field of new anthracene luminescent materials and their preparation, can solve the problem of quantum efficiency less than 1%, and achieve the effect of improving luminous intensity

Active Publication Date: 2018-10-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since Pope et al. first discovered that anthracene single crystal has organic electroluminescence, although its driving voltage is as high as 400V and its quantum efficiency is less than 1%, it has opened up a road to the development of blue fluorescent materials.

Method used

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  • Novel anthracene luminescent material, preparation method, and applications thereof
  • Novel anthracene luminescent material, preparation method, and applications thereof
  • Novel anthracene luminescent material, preparation method, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Preparation of 2,3,6,7,9,10-hexa-bromoanthracene

[0054] Under the condition of nitrogen protection, 1 part of anthracene was dissolved in dichloromethane, and iron powder (the molar ratio of iron powder:anthracene was 1:1~10), bromine water (the molar ratio of bromine water:anthracene was 1:1) ~10) respectively add to a single-neck bottle, stir vigorously at room temperature for 6h, filter to obtain insoluble matter, and further wash with dilute hydrochloric acid, purified water and acetone to obtain 2,3,6,7,9,10-hexa-bromoanthracene (shown by 1 in formula (1)), its synthetic route is shown in formula (1), and the yield of 2,3,6,7,9,10-hexa-bromoanthracene is about 70%.

[0055]

Embodiment 2

[0057] Under the condition of nitrogen protection, 1 part of 9-anthracene was dissolved in dichloromethane, and iron powder (the molar ratio of iron powder: 9-bromoanthracene was 1:1~10), bromine water (bromine water: 9-bromine The molar ratio of anthracene is 1:1~10) were added into single-neck flasks, stirred vigorously at room temperature for 6h, filtered to obtain insoluble matter, and further washed with dilute hydrochloric acid, purified water and acetone to obtain mixtures 2, 3, 6, 7,9,10-hexa-bromoanthracene (shown by 1 in formula (2)) and 2,3,6,7,9-penta-bromoanthracene (shown by 1' in formula (2)), its synthetic route As shown in formula (2), the yield of 2,3,6,7,9,10-hexa-bromoanthracene is about 65%.

[0058]

Embodiment 3

[0059] Example 3 Preparation of 2,3,6,7,9,10-hexa-(4-methoxyphenyl)anthracene

[0060] 1. Under the condition of nitrogen protection, the 2,3,6,7,9,10-hexa-bromoanthracene and 4-methoxyphenyl borate (molar ratio is 1:7) in step 1, Add tetrakis(triphenylphosphine)palladium and potassium carbonate into a single-necked bottle, then 10-20mL of toluene and ethanol, stir vigorously, keep the temperature at 90°C, reflux for 24h, extract, wash and filter to obtain the initial product, and go through column chromatography Chromatography or recrystallization, obtain 2,3,6,7,9,10-hexa-(4-methoxyphenyl) anthracene, its molecular structure is as shown in 2a in formula (3), and its synthetic route is as formula ( 3), the yield is about 60%.

[0061]

[0062] figure 1 For the 2,3,6,7,9,10-sixa-(4-methoxyphenyl)-anthracene obtained in this example 1 H CNMR diagram. figure 2 For the 2,3,6,7,9,10-sixa-(4-methoxyphenyl)-anthracene obtained in this example 13 C NMR image. image 3 In or...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a novel anthracene luminescent material, a preparation method and applications thereof; the preparation method includes the steps of: in an inert gas atmosphere, performing a bromination reaction to anthracene, 9-bromoanthracene or 9,10-dibromoanthracene as raw material with addition of a bromination agent under catalysis by metal or Lewis acid; then performing palladium-catalyzed coupling reaction to introduce substituent groups on the 2nd, 3rd, 6th, 7th, 9th and 10th or 2nd, 3rd, 6th, 7th and 9th loci of theanthracene. The luminescent material has a symmetrical functionalized molecular structure of anthracene, so that luminescent intensity, color purity and stability are improved. For the first time, through catalysis, the substituent groups are introduced onto the 2nd, 3rd, 6th, 7th, 9th and 10th or 2nd, 3rd, 6th, 7th and 9th loci of the anthracene, so that molecular planarity is damaged and [pi]-[pi] stacking is inhibited, thus improving the luminescent efficiency and quantum yield performance of the material are enhanced, controlling the luminescent range of the material, inhibiting crystallization, improving film-forming property and improving charge transmission performance.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductors, and more specifically relates to a novel anthracene-based luminescent material and its preparation method and application. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diodes, OLED) devices have excellent characteristics such as high efficiency, high brightness, ultra-thin, ultra-light, and flexibility, and have broad application prospects in the fields of information display and lighting. As the next generation flat panel display technology, [0003] Organic light-emitting diodes have attracted extensive attention from academia and industry. According to the latest report, BOE has successfully realized the mass production of the 6th generation flexible AMOLED production line. To realize the full-color display of OLEDs, high-efficiency three-color organic light-emitting materials—red, green and blue materials are essential. Especially blue-...

Claims

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Application Information

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IPC IPC(8): C07D319/02C07C25/22C07C17/12C07C41/30C07C43/205C07C45/68C07C47/546C07D209/86C09K11/06
CPCC07C17/12C07C25/22C07C41/30C07C43/2055C07C45/68C07C47/546C07D209/86C07D319/02C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088
Inventor 冯星吴荣东姚家杰牟中飞李京波
Owner GUANGDONG UNIV OF TECH
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