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Rubrene derivatives and preparation method thereof

A technology of derivatives and rubrene, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of concentration quenching effect and low fluorescence quantum yield, and achieve reduced concentration quenching effect and high fluorescence Quantum efficiency and the effect of improving luminous performance

Inactive Publication Date: 2011-08-24
DONGGUAN ANWELL DIGITAL MASCH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the problems of low fluorescence quantum yield and concentration quenching effect in red light materials in the prior art, the purpose of the present invention is to provide a rubrene derivative with high quantum yield and stable performance and its preparation method. The rubrene derivative is characterized in that it has the following general structural formula:

Method used

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  • Rubrene derivatives and preparation method thereof
  • Rubrene derivatives and preparation method thereof
  • Rubrene derivatives and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1: 5,6,11,12-tetra-tert-butylbenzene-naphthonaphthalene synthesis (such as figure 1 ):

[0038] (1) Synthesis of 1,3-di-p-tert-butylbenzofuran

[0039] In a 150ml four-neck flask, stir and dissolve p-tert-butylbromobenzene (4.24g, 20mmol) in 50ml THF or DMF, cool to -78°C, and add 1.6M n-butyllithium n-hexane solution through a constant pressure dropping funnel (12.5ml20mmol) was added dropwise, keeping the temperature of the mixture in the flask lower than -60°C, at -78°C, stirred for 1h, then continued to drop p-3-tert-butylphenyl-phenylpeptide (5.32 g, 20mmol) in THF or 25ml of DMF solution, the dark red mixed solution was stirred at -78°C for 15min, then added acetic anhydride (2.0ml, 20mmol) and slowly raised to room temperature, then heated to reflux for 10min, and 50ml of water was added to end the reaction. The organic layer was separated and washed with anhydrous MgSO 4 After being dried and spin-dried in vacuo, recrystallized with a mixed solvent...

Embodiment 2

[0055] Embodiment 2: 5,6,11, the synthesis of 12-tetrabromobenzene-naphthacene (as figure 2 ):

[0056] (1). Synthesis of 1,3-di-p-bromophenylbenzofuran

[0057] In a 150ml four-neck flask, dissolve p-bromoiodobenzene (5.64g, 20mmol) in 50mlTHF, cool to -78°C, and add 1.6M n-butyllithium-n-hexane solution (12.5ml 20mmol) gradually through a constant pressure dropping funnel Drop in, keep the temperature of the mixture in the flask lower than -60°C, stir for 1h at -78°C, then continue to drop 25ml of THF solution of terephthalic anhydride (5.76g, 10mmol) in 45 minutes, deep The red mixed solution was stirred at -78°C for 15min, then added acetic anhydride (1.0ml, 10mmol) and slowly raised to room temperature, then heated to reflux for 10min, and 50ml of water was added to complete the reaction, the organic layer was separated and washed with anhydrous MgSO 4 After drying and spin-drying in vacuo, recrystallization was performed with a mixed solvent of ethanol and benzene to ...

Embodiment 3

[0073] Embodiment 3: 5,11-di-tert-butylbenzene-6, the synthesis of 12-triphenylamine-naphthacene (as image 3 ):

[0074] (1) Synthesis of 5,11-p-tert-butylphenyl-naphthoquinone

[0075] In a 150ml four-necked flask, 1.3-p-tert-butylbenzofuran (0.2g, 0.5mmol) was slowly added to 5ml CH of 0.08g (0.5mmol) 1,4-naphthoquinone 2 Cl 2 solution, stirred at room temperature for 12h, continued to add 10ml CH 2 Cl 2 , cooled to -78°C, 0.58ml 1M BBr 3 CH 2 Cl 2 The solution was added dropwise and reacted at -78°C for 0.5h. The dark black reaction system was then raised to room temperature, heated to reflux for 4h, and then cooled to room temperature. The reaction solution was poured into water, and the aqueous phase was separated with CH 2 Cl 2 Extraction, combined organic phases, washed with brine, anhydrous MgSO 4 Dry and concentrate in vacuo to give a yellow oil, CHCl 3 -MeOH was recrystallized to obtain a yellow solid with a yield of 55.5%.

[0076] (2) Synthesis of 6-hy...

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PUM

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Abstract

The invention relates to a 6, 11 dibasic-5,12-naphthalene and naphthoquinone which is generated by implementing a Diels-Alder cycloaddition reaction through 1,3-dibasic benzofuran and benzene naphthoquinone, and then a rubrene derivative is generated by substituting addition reaction through the lithium alkylide, through a structural modification, the main rubrene body is introduced with a plurality of active conjugation radicals, so that the emission wavelength of the main body is in red shift, thereby a red light emission wavelength is realized, simultaneously, the steric hindrance between the molecules can be enlarged through introducing larger radicals; so the glass transition temperature can be raised; the concentration quenching effect can be lowered and the lightening property of material can be improved.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a rubrene-substituted red organic electroluminescent material and a preparation method thereof. Background technique [0002] Organic Light-Emitting Display (OLED), also known as organic electroluminescent display (OELD), is a display device that causes organic materials to emit light through carrier injection and recombination under the drive of an electric field. OLED has the characteristics of low cost, all solid state, active light emission, high brightness, high contrast, wide viewing angle, fast response, thin thickness, low voltage DC drive, low power consumption, wide operating temperature range, and soft screen display. [0003] At present, the organic small molecule luminescent material AlQ3 is a very good green light luminescent small molecule material, and its green light color purity, luminous efficiency and stability are all very go...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/546C07C25/22C07C15/56C07C211/57C09K11/06
Inventor 宋君王健徐宁
Owner DONGGUAN ANWELL DIGITAL MASCH CO LTD
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