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Novel blue light material-thiotrzinone-containing anthracene derivatives

A technology of triazine rings and derivatives, which is applied in the field of new anthracene derivatives containing triazine rings, can solve the problems of industrialization and other problems, and achieve good electron transfer performance, high thermal stability, and excellent electrochemical performance. Effect

Inactive Publication Date: 2006-06-21
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After more than 20 years of hard work, green devices have been partially commercialized, while blue and red devices are still far from industrialization due to efficiency or life expectancy.

Method used

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  • Novel blue light material-thiotrzinone-containing anthracene derivatives
  • Novel blue light material-thiotrzinone-containing anthracene derivatives
  • Novel blue light material-thiotrzinone-containing anthracene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of 2-methyl-9,10-diphenyl-anthracene

[0029]

[0030] Under argon protection and vigorous stirring, a solution of bromobenzene (7.9g, 50mmol) in THF (tetrahydrofuran, 40mL) was added dropwise at 60°C to a solution containing magnesium (1.44g, 60mmol), a catalytic amount of iodine and THF (40mL). In the mixed solution, after dropping, continue to stir and reflux for 3 hours, then cool to room temperature. The resulting solution was added dropwise to a THF (80mL) solution of 2-methylanthraquinone (5.4g, 24mmol) cooled to -78°C under the protection of argon under the protection of argon. After the addition was complete, the reaction solution was naturally warmed to room temperature and stirred. After overnight, pour into 100 mL of distilled water and extract twice with dichloromethane (200 mL). The organic phases were combined, washed with water, washed with saturated brine and dried over anhydrous sodium sulfate, then filtered, and the solvent was...

Embodiment 2

[0031] Example 2 Synthesis of 2-methyl-9,10-bis(2-naphthyl)-anthracene

[0032]

[0033] In an atmosphere of argon, 2-bromonaphthalene (10.4 g, 50 mmol) was added dropwise to a vigorously stirred mixture containing magnesium (1.4 g, 60 mmol), catalytic amount of iodine and THF (40 mL) at 60 °C solution in THF (40 mL). After dropping, the reaction solution was stirred and refluxed for 3 hours, then cooled to room temperature. The resulting solution was added dropwise to a solution of 2-methylanthraquinone (5.4 g, 24 mmol) in THF (80 mL) that had been cooled to -78°C under the protection of argon with stirring. After the addition was complete, the reaction solution was naturally warmed to room temperature and stirred overnight, poured into 100mL distilled water, extracted twice with dichloromethane (200mL), combined the organic phases, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was distilled off the solv...

Embodiment 3

[0034] Example 3 Synthesis of 2-methyl-9,10-bis(pentafluorophenyl)-anthracene

[0035]

[0036] In an argon atmosphere, at -78°C, in a solution of 1-bromo-2,3,4,5,6-tetrafluorobenzene (12.4g, 50mmol) in THF (40mL), slowly dropwise add n-butyllithium n-Hexane solution (1.6 mol / L, 35 mL). After stirring at this temperature for 1 hour, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature naturally. The obtained material was slowly added to a solution of 2-methylanthraquinone (5.4 g, 24 mmol) in THF (80 mL) which had been cooled to -78°C under the protection of argon. After the addition was complete, the reaction solution was naturally warmed to room temperature, then heated to reflux, and stirred overnight at this temperature. After the mixture was cooled to room temperature, it was poured into 100 mL of distilled water, and extracted twice with dichloromethane (200 mL). The organic phases were combined, washed with water, washed wit...

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Abstract

The invention relates to an anthracene deviant containing triazine ring, its preparing method and application, which is prepared through trilooping reaction under strong protonic acid catalysis with cyano anthracene derivant. The molecular structure of this material employs triazine ring as parent body and employs anthracene derivant as extending arm. The product can be used as luminescent layer for organic light-emitting diode, and the produced device emits blue light. The invention is characterized by the simple synthetic process, easy for purification, high heat stability, easy to dissolve into normal organic dissolvent and high fluorescent light intensity.

Description

technical field [0001] The invention relates to a novel anthracene derivative containing a triazine ring, which is prepared from commercial 2-methylanthraquinone and aromatic halogenated hydrocarbons as starting materials. The compound provided by the invention is a kind of blue organic electroluminescent material with electron transport performance. Background technique [0002] Organic light-emitting diodes (OLEDs) have drawn close attention from the scientific and industrial circles because of their great application prospects in various displays. After more than 20 years of hard work, green devices have been partially commercialized, while blue and red devices are still far from industrialization due to reasons such as efficiency or lifespan. Due to the final use of organic electrophoresis, it is a new generation of large-scale ultra-thin color display screens (Science, 1996, 273, 884; Journal of the American Chemical Society, 2002, 124, 11576), therefore, research on n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/24C09K11/06H01L51/54H05B33/14
Inventor 房强陈小幺姜标金松卜东生黄浩何钧杜俊平任世杰余锋徐兵曾丹黎许二建
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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