9,9<,>-bisanthracene derivative and preparation method thereof

A derivative, bianthracene technology, applied in the field of blue organic electroluminescent materials, can solve the problems of less variety and the need to improve the fluorescence quantum efficiency of compounds

Inactive Publication Date: 2011-10-26
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Bianthracene-based blue light materials are a new type of blue light materials that have attracted widespread attention in recent years. At present, there are few varieties of this kind of blue light materials. In 2007, Lanzhou University reported for the first time that 9,9'-Bianthracene (its structural formula is as shown in I) shown) OLED devices as blue light materials, but the fluorescence quantum efficiency of this compound needs to be improved

Method used

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  • 9,9&lt;,&gt;-bisanthracene derivative and preparation method thereof
  • 9,9&lt;,&gt;-bisanthracene derivative and preparation method thereof
  • 9,9&lt;,&gt;-bisanthracene derivative and preparation method thereof

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Embodiment 1

[0022] Embodiment 1,10, the synthesis of 10'-diphenyl-9,9'-bianthracene

[0023] The present invention is implemented according to the following synthetic route

[0024]

[0025] 1) Synthesis of phenylboronic acid

[0026] In a 250mL round-bottomed bottle, add magnesium powder (0.72g, 0.03mol), bromobenzene (1.57g, 0.01mol), tributyl borate (4g, 0.02mol), and 20mL of tetrahydrofuran dried through molecular sieves. Condenser. Ultrasonic radiation was carried out after heating to 40° C. in an ultrasonic cleaner, and the reaction was completed after 1 hour. Add 2mol·L -1 5mL of hydrochloric acid, and after stirring for a while, the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 mL×2), several layers were combined and washed with water until neutral, dried and the solvent was removed to obtain a crude product. Recrystallization was carried out with ethanol: water = 2: 1, and 0.87 g of solid powder was obtained after drying under reduced...

Embodiment 2

[0036] Embodiment 2,10, the synthesis of 10'-bis(4-ethyl)phenyl-9,9-bianthracene

[0037] The present invention is implemented according to the following synthetic route

[0038]

[0039] 1) Synthesis of p-ethylphenylboronic acid

[0040] In a 250mL round bottom bottle, add magnesium powder (0.72g, 0.03mol), 4-ethylbromobenzene (1.85g, 0.01mol), tributyl borate (4g, 0.02mol), and 20mL of tetrahydrofuran dried over molecular sieves , install the reflux condenser. Ultrasonic radiation was carried out after heating to 40° C. in an ultrasonic cleaner, and the reaction was completed after 1 hour. Add 2mol·L -1 5mL of hydrochloric acid, and after stirring for a while, the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 mL×2), several layers were combined and washed with water until neutral, dried and the solvent was removed to obtain a crude product. Recrystallization was carried out with ethanol: water = 2: 1, and 1.12 g of solid powder w...

Embodiment 3

[0049] Embodiment 3,10, the synthesis of 10'-two (4-propyl) phenyl-9,9'-bianthracene

[0050] The present invention is implemented according to the following synthetic route

[0051]

[0052] 1) Synthesis of p-propylphenylboronic acid

[0053] In a 250mL round bottom bottle, add magnesium powder (0.72g, 0.03mol), 4-propyl bromobenzene (2g, 0.01mol), tributyl borate (4g, 0.02mol), 20mL of tetrahydrofuran dried through molecular sieves, Install the reflux condenser. Ultrasonic radiation was carried out after heating to 40° C. in an ultrasonic cleaner, and the reaction was completed after 1 hour. Add 2mol·L -1 5mL of hydrochloric acid, and after stirring for a while, the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 mL×2), several layers were combined and washed with water until neutral, dried and the solvent was removed to obtain a crude product. Recrystallization was carried out with ethanol: water = 2: 1, and 1.11 g of solid powder...

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Abstract

The invention discloses a 9,9<,>- bisanthracene derivative having the following structural formula shown in the description, wherein, R is hydrogen, ethyl, propyl or 4-propyl cyclohexyl. The invention also discloses a preparation method of the 9,9<,>- bisanthracene derivative, comprising the following steps: (1) adding magnesium powder, bromo aromatic hydrocarbon, tributyl borate in anhydrous tetrahydrofuran, for an ultrasonic radiation reaction for 1h at the temperature of 40 DEG C to obtain aryl boric acid, wherein, the molar ratio of bromo aromatic hydrocarbon to tributyl borate to magnesium powder is 1:2:3; and (2) adding 10,10<,>-dibromo-9,9<,>- bisanthracene, aryl boric acid and tetra(triphenylphosphine) palladium in a solution containing toluene, ethanol and sodium bicarbonate, wherein, the volume ratio of toluene to ethanol to sodium bicarbonate is 4:2:1, the molar ratio of 10,10<,>-dibromo-9,9<,>- bisanthracene to aryl boric acid is 2.5 :1, the amount of tetra(triphenylphosphine) palladium is 10% of the amount of 10,10<,>-dibromo-9,9<,>- bisanthracene compound, then reversing flow to obtain the 9,9<,>-bisanthracene derivative.

Description

technical field [0001] The invention relates to a blue organic electroluminescent material, in particular to a blue organic electroluminescent material of 9,9'-bianthracene derivatives. Background technique [0002] Organic electroluminescent devices (OLEDs) have the advantages of high luminous efficiency, low driving voltage, active luminescence, high brightness, wide viewing angle, fast response speed, and full-color flat-panel display, so they have broad applications in the fields of flat-panel displays and solid-state light sources. It also has important application value in the fields of display and lighting. Since C.W.Tang et al. of Kodak Company first developed a valuable low driving voltage organic electroluminescent device in 1987, OLED has attracted great attention of scientific researchers in various countries and has become a research hotspot in the field of light-emitting display. [0003] In the research of OLED, red, green and blue three primary color materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/60C07C1/32C09K11/06
Inventor 徐茂梁王子俊田杰安永宋新潮弥阳丽
Owner XIAN MODERN CHEM RES INST
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