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Polyanthracene compound, and preparation method and application thereof

A compound and polymer technology, applied in polyanthracene and its synthesis method, and in the application field of polymer light-emitting diodes, can solve the problems of troublesome processing, deep color, wide spectrum, etc. high rate effect

Inactive Publication Date: 2018-05-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It was previously reported that ferric chloride was oxidatively polymerized (please refer to Journal Of Applied Polymer Science2013, 127, 4524). It may be oxidized or oxidized, the color is darker, the post-treatment is more troublesome, and the purification is more difficult. The product The fluorescent colors are colorful and the spectrum is very wide

Method used

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  • Polyanthracene compound, and preparation method and application thereof
  • Polyanthracene compound, and preparation method and application thereof
  • Polyanthracene compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of 9,10-dibromoanthracene, the synthetic route is as follows:

[0036]

[0037] Add anthracene (10g, 56.1mmol) and 200ml chloroform in a 1000ml single-necked flask, stir and dissolve at room temperature, add liquid bromine (18g, 112.6mmol) and 100ml chloroform in a 250ml constant pressure funnel, and keep the reaction device away from light. And the ventilation tube on the constant pressure funnel was piped into the sodium hydroxide solution, and stirred at room temperature for 4 hours. Add sodium hydroxide solution to quench, after layering, wash the organic layer with brine, add anhydrous magnesium sulfate to dry, spin off the solvent after Buchner funnel filtration, and dry it with a vacuum pump to obtain a yellow solid, which is recrystallized with toluene to obtain 16.7 g of yellow needles, yield 88.6%. 1 H NMR (600MHz, CDCl 3 )δ8.67–8.47(m,4H),7.69–7.58(m,4H).

[0038] Add 9,10-dibromoanthracene (0.25g, 0.744mmol) and activated magnesium (0.0...

Embodiment 2

[0040] The preparation of 2-n-butyl-9,10-dibromoanthracene, the synthetic route is as follows:

[0041]

[0042] Add phthalic anhydride (11.11g, 75mmol), anhydrous aluminum chloride (24g, 180mmol), and 50ml of chloroform into a three-necked flask, and add n-butylbenzene (10.07g, 75mmol) and 50ml of chloroform into a constant pressure funnel , drop slowly, react at 50°C for 1 hour after the drop is completed, then rise to cool, pour into a mixed solution of 48ml concentrated hydrochloric acid and 96g ice to quench, add chloroform to extract three times, add anhydrous magnesium sulfate to dry, and use Brinell After filtering through the funnel, the solvent was evaporated by rotary evaporation, and dried by vacuum pump to obtain 21.09 g of brown solid, with a crude yield of 99.6%.

[0043] Add 2-(3-n-butylbenzoyl)benzoic acid (21.09g, 74.7mmol) and 126ml of concentrated sulfuric acid into a single-necked flask, react at 125°C for one hour, pour into ice to quench, extract with...

Embodiment 3

[0048] The preparation of 2-tert-butyl-9,10-dibromoanthracene, the synthetic route is as follows:

[0049]

[0050] Weigh phthalic anhydride (11.11g, 75mmol), anhydrous aluminum chloride (24g, 180mmol), and 50ml of chloroform in a single-necked bottle, and add tert-butylbenzene (10.07g, 75mmol) and chloroform into the constant pressure funnel Add 50ml slowly, react at 50°C for 1 hour after the drop, rise to cool, pour into a mixed solution of 48ml concentrated hydrochloric acid and 96g ice to quench, add chloroform to extract three times, add anhydrous magnesium sulfate to dry, Brinell After filtering through the funnel, the solvent was evaporated and sucked to dryness to obtain 21.68 g of a brown solid, and the crude yield was greater than 100%.

[0051] Add 2-(3-tert-butylbenzoyl)benzoic acid (4.35g, 15.4mmol) and 25ml concentrated sulfuric acid into a single-necked bottle, react at 125°C for one hour, pour into ice to quench, extract with toluene, add anhydrous Dry over...

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Abstract

The invention belongs to the field of organic light-emitting diodes, and specifically discloses a polyanthracene compound, and a preparation method and application thereof. The structure of polyanthracene is as shown in a formula I in the description, wherein R1 to R4 are same or different C1 to C20 long-chain alkyl and are connected with aryl in a form of alkyl or alkoxy. According to the preparation method, 9,10-dibromoanthracene with different groups is firstly synthesized, then the 9,10-dibromoanthracene is reacted with magnesium to generate a Grignard reagent, and finally free radical polycondensation is carried out under high-temperature conditions to generate poly(9,10-anthracene). According to the invention, an anthracene oligomer is synthesized by employing a free radical couplingmethod, has a narrow spectrum and only emits blue light. The method has a clean system, is simple in operation, does not easily bring impurities, and has a high synthesis yield. The polyanthracene compound can be used in polymer light emitting diodes.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a polyanthracene and its synthesis method and application in polymer light-emitting diodes. Background technique [0002] The phenomenon of organic electroluminescence can be traced back to 1963. Pope's research group and Visco's research group found that blue light emission could be observed by applying a DC voltage of not less than 400V to micron-thick anthracene single crystals. Until 1987, Dr. Deng Qingyun of Kodak Company of the United States and others invented a sandwich-type organic double-layer thin film electroluminescent device, using 8-hydroxyquinoline aluminum as the material of the light-emitting layer, and the luminous brightness of the device reached 1000cd / m 2 , the external quantum efficiency is increased to 1%, and the efficiency is 1.51m / W, thus arousing a research boom of organic electroluminescent materials and devices. In 1990, Burroughes et ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/10
CPCC08G61/10C08G2261/11C08G2261/1412C08G2261/18C08G2261/314C08G2261/5222C08G2261/91C08G2261/94C08G2261/95
Inventor 莫越奇潘雅娟
Owner SOUTH CHINA UNIV OF TECH
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