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Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compounds, synthesis method and application thereof

A synthesis method and compound technology, applied in 4 fields, can solve the problems of affecting performance test, not very good solubility, not very good solubility of anthraline-based small molecule compounds, etc.

Inactive Publication Date: 2012-05-09
NANJING UNIV OF TECH
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Problems solved by technology

However, the solubility of the anthracene-based small molecule compounds reported above is not very good, which affects some of their performance tests and their further development in the field of OLEDs.
Therefore, in order to solve the problem that the solubility of small-molecule anthracene compounds is not very good, our research group designed and synthesized a series of organic light-emitting materials of 4,6-diphenyl-1,9-anthracene compounds, hoping to ensure Under the premise of their excellent fluorescence quantum efficiency and thermal stability, they can better solve the solubility problem of this type of compound

Method used

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  • Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compounds, synthesis method and application thereof
  • Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compounds, synthesis method and application thereof
  • Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compounds, synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0045] Embodiment 1: 2,4,6,8-tetraphenyl-1,9-anthracene ( 1a )Synthesis

[0046] 4,6-dibenzoyl-1,3-m-phenylenediamine (0.6328g, 2.0mmol), acetophenone 0.5046g (4.2mmol) was added to polyphosphoric acid (4.2g) and m-cresol (10ml) and mixed In the solution, stir magnetically, control the temperature at 130-140°C, and react for 50h. Then cool to 80°C, dilute with methanol (50ml), pour 1mol·L -1 KOH aqueous solution (500ml), filtered, and the precipitate was collected, washed 3 times with hot water (500ml each time), and dried. Finally, recrystallize twice with methanol / THF solution (methanol / THF volume ratio is 30-60%) to obtain orange-yellow flaky solid 2,4,6,8-tetraphenyl-1,9-anthraline (1a ) 0.78g, yield 80.5%, melting point 265.4 ℃, see attached figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

Embodiment 2

[0047] Embodiment 2: 2,8-two (p-tert-butylphenyl)-4,6-diphenyl-1,9-anthracene ( 1b )Synthesis

[0048] 4,6-dibenzoyl-1,3-m-phenylenediamine (0.6328g, 2.0mmol), p-tert-butylacetophenone 0.7402g (4.2mmol) was added to polyphosphoric acid (4.2g) and m-cresol (10ml) in the mixed solution, magnetically stirred, temperature controlled at 130-140°C, and reacted for 50h. Then cool to 80°C, dilute with methanol (50ml), pour 1mol·L -1 KOH aqueous solution (500ml), filtered, and the precipitate was collected, washed 3 times with hot water (500ml each time), and dried. Finally, recrystallize twice with methanol / THF solution (methanol / THF volume ratio is 30-60%) to obtain yellow flaky solid 2,8-bis(p-tert-butylphenyl)-4,6-diphenyl -1,9-Anthracene ( 1b ) 0.72g, yield 60.4%, melting point 280.9 ℃, see attached figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

Embodiment 3

[0049] Embodiment 3: 2,8-two (p-methoxyphenyl)-4,6-diphenyl-1,9-anthracene ( 1c )Synthesis

[0050] 4,6-dibenzoyl-1,3-m-phenylenediamine (0.6328g, 2.0mmol), p-methoxyacetophenone 0.6303g (4.2mmol) was added to polyphosphoric acid (4.2g) and m-cresol (10ml) in the mixed solution, magnetically stirred, temperature controlled at 130-140°C, and reacted for 50h. Then cool to 80°C, dilute with methanol (50ml), pour 1mol·L -1 KOH aqueous solution (500ml), filtered, and the precipitate was collected, washed 3 times with hot water (500ml each time), and dried. Finally, recrystallize twice with methanol / THF solution (methanol / THF volume ratio is 30-60%) to obtain bright yellow needle-like solid 2,8-bis(p-methoxyphenyl)-4,6-diphenyl Base-1,9-anthracene ( 1c ) 0.70g, yield 64.3%, melting point 266.5 ℃, see attached figure 1 , the fluorescence emission spectrum is shown in the attached figure 2 .

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Abstract

The invention provides a 4, 6-diphenyl-1, 9-anthralin compound luminescent material, a preparation method and application thereof. In the invention, 4, 6-dibenzoyl-1, 3-m-phenylenediamine and p-alkyl hypnone, p-acetyl biphenyl, p-acetyl diphenyl ether, 2-acetamidofluorene, 3-acetyl carbazole and mono-acetyl compounds substituted by alkyl thereof are used as raw materials, polyphosphoric acid is adopted as a catalyst, metacresol is employed as solvent, and a Friedlander condensation reaction is performed to obtain a series of 4, 6-diphenyl-1, 9-anthralin compounds which can be used as a luminous layer or an electron transport layer of an organic light emitting diode.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a 4,6-diphenyl-1,9-anthracene compound, a synthesis method and an application. The compound has light-emitting properties and can be used as a light-emitting layer or an electron-transporting layer of an organic light-emitting diode. technical background [0002] Organic light-emitting diode display device (Organic light-emitting diode, OLED) because of its high luminous brightness, low driving voltage, low power consumption, fast response, high definition, full-color display, simple process and other advantages, will become A strong contender for next-generation light sources and flat-panel displays. In recent years, the research in the field of organic thin film electroluminescence has mainly focused on controlling the luminous color of OLEDs, improving the efficiency and life of the device, including optimizing the manufacturing process of the devic...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/54
Inventor 朱红军章勤姜鹏王昆彦张东明吴涛施路陈琛
Owner NANJING UNIV OF TECH
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