Organic luminescent material 9-(4-aryl ethynyl phenyl) carbazoles compounds, synthesis method and uses

A technology of ethynylphenyl and synthetic methods, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc.

Inactive Publication Date: 2009-11-25
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are no literature and patent reports for further structural modification and synthesis research on it.

Method used

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  • Organic luminescent material 9-(4-aryl ethynyl phenyl) carbazoles compounds, synthesis method and uses
  • Organic luminescent material 9-(4-aryl ethynyl phenyl) carbazoles compounds, synthesis method and uses
  • Organic luminescent material 9-(4-aryl ethynyl phenyl) carbazoles compounds, synthesis method and uses

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Experimental program
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Embodiment 1

[0036] Embodiment 1: 9-(4-(4-methylphenylethynyl) phenyl) carbazole ( 1a )Synthesis

[0037] Add 1.18g (3.2mmol) of 9-(4-iodophenyl)carbazole, 0.098g (0.14mmol) of bistriphenylphosphine palladium dichloride, and 0.026g (0.14mmol) of cuprous iodide into a 100mL four-neck flask , 1.86g (4.48mmol) of tri-tert-butylamine and 30mL of tetrahydrofuran were stirred at room temperature for 0.5h under the protection of nitrogen, then 0.43g (3.68mmol) of p-methylphenylacetylene was added, and the reaction was continued for 24h, and then 50mL of water was added to quench the reaction. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4Dry, evaporate the solvent under reduced pressure to obtain a black solid, which is separated and purified by column chromatography (filling with silica gel, petroleum ether / dichloromethane) to obtain a light yellow solid 9-(4-(4-methylphenylethynyl)phenyl) Carbazole 0.97g, productive rate 7...

Embodiment 2

[0038] Embodiment 2: 9-(4-(4-methoxyphenylethynyl) phenyl) carbazole ( 1b )Synthesis

[0039] Add 1.18g (3.2mmol) of 9-(4-iodophenyl)carbazole, 0.098g (0.14mmol) of bistriphenylphosphine palladium dichloride, and 0.026g (0.14mmol) of cuprous iodide into a 100mL four-neck flask , 1.86g (4.48mmol) of tri-tert-butylamine and 30mL of tetrahydrofuran were stirred at room temperature for 0.5h under the protection of nitrogen, then 0.49g (3.68mmol) of p-methoxyphenylacetylene was added, and the reaction was continued for 24h, and then 50mL of water was added to quench the reaction. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, evaporate the solvent under reduced pressure to obtain a black solid, which is separated and purified by column chromatography (filling with silica gel, petroleum ether / dichloromethane) to obtain a light yellow solid 9-(4-(4-methoxyphenylethynyl)phenyl ) carbazole 0.75g, productive r...

Embodiment 3

[0040] Embodiment 3: 9-(4-(4-thioacetylphenylethynyl) phenyl) carbazole ( 1c )Synthesis

[0041] Add 1.18g (3.2mmol) of 9-(4-iodophenyl)carbazole, 0.098g (0.14mmol) of bistriphenylphosphine palladium dichloride, and 0.026g (0.14mmol) of cuprous iodide into a 100mL four-neck flask , 1.86g (4.48mmol) of tri-tert-butylamine and 30mL of tetrahydrofuran were stirred at room temperature for 0.5h under the protection of nitrogen, then 0.65g (3.68mmol) of p-thioacetylphenylacetylene was added, and the reaction was continued for 24h, and then 50mL of water was added to quench the reaction. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, evaporate the solvent under reduced pressure to obtain a black solid, which is separated and purified by column chromatography (filling with silica gel, petroleum ether / dichloromethane) to obtain a light yellow solid 9-(4-(4-thioacetylphenylethynyl)benzene Base) carbazole 1.06g...

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Abstract

The present invention provides an organic luminescent material 9-(4-aryl ethynyl phenyl) carbazoles, prepartion method and uses. The invention uses 9-(4-iodo-benzene) carbazole or derivates thereof as raw materials, under the action of tri-n-butylamine, using dual-triphenylphosphine palladium dichloride/cuprous iodide as catalyst to proceed a Sonogashira coupling reaction with the terminal aryne in tetrahydrofuran for 20 to 50 hours to obtain series of 9-(4-aryl ethynyl phenyl) carbazoles compounds. The compounds can by used as organic luminescent materials.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a 9-(4-arylethynylphenyl) carbazole compound, a synthesis method and an application. The compound has light-emitting properties, and can be used as an organic light-emitting material in the fields of light-emitting devices, photovoltaic cells, organic light-emitting diodes, and the like. technical background [0002] Organic light-emitting diode display device (Organic light-emitting diode, OLED) will become a new generation of light source and flat panel due to its many excellent advantages such as rich colors, active light emission, small size, thin thickness, wide viewing angle, low energy consumption and fast response speed. A strong contender for the display. So far, the development of novel and highly stable carrier-transporting materials and light-emitting materials is a key factor in improving the efficiency and lifetime of organic electronic, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D409/10C07D401/10C09K11/06
Inventor 朱红军刘睿常进李钰皓肖琪陈洪彬
Owner NANJING UNIV OF TECH
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