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9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-dicarbazole and synthesis method thereof

A synthetic method, the technology of bicarbazole, applied in the field of organic chemical synthesis, can solve the problems of reducing the rigidity of the plane, and there is no research report on the structure and synthetic method, and achieve the effect of easy separation, good stability, and simple operation process

Active Publication Date: 2019-01-18
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2,9′-Bicarbazole is a very important class of carbazole derivatives. Its special structure is suitable for application in hole transport materials. 9-([1,1′-biphenyl]-3-yl) -2'-Bromo-2,9'-bicarbazole is chemically modified on the basis of 2,9'-bicarbazole, which reduces the plane rigidity and increases the conjugated system, making it more suitable as an electroluminescent material and Its intermediates are used, and there is no research report on its structure and synthesis method. The research of this kind of compound will help to improve the performance of organic electroluminescent materials, especially hole transport materials, and expand their applications.

Method used

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  • 9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-dicarbazole and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0023] Add 54.1g (0.22mol) of 2-bromocarbazole, 28.0g (0.1mol) of 3-iodobiphenyl, 33.1g (0.02mol) of potassium iodide, and Dipotassium hydrogen 153.3g (0.88mol), then add 300mL N-methylpyrrolidone solvent to dissolve. After being protected by argon, 5.7 g (0.03 mol) of cuprous 2-thiophenecarboxylate was added, the reaction temperature was controlled at 110° C., and mechanical stirring at constant temperature was continued for 36 hours. After the reaction was detected by high performance liquid chromatography, water was added to terminate the reaction. The reaction solution was extracted with 300 mL of dichloromethane, the organic layer was washed with ammonia solution, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain a crude product, which was recrystallized from a mixed solvent of 300 mL of toluene and 300 mL of methanol to obtain 47.5 g of off-white powder. The yield is 84.2%, the content ...

Embodiment 2

[0026] Add 98.5g (0.4mol) of 2-bromocarbazole, 140.1g (0.2mol) of 3-iodobiphenyl, 6.6g (0.04mol) of potassium iodide, and phosphoric acid Dipotassium hydrogen 348.4g (2mol), then add 500mL N-methylpyrrolidone solvent to dissolve. After being protected by argon, 11.5 g (0.06 mol) of cuprous 2-thiophenecarboxylate was added, the reaction temperature was controlled at 100°C, and mechanical stirring at constant temperature was continued for 48 hours. After the reaction was detected by high performance liquid chromatography, the reaction was terminated by adding water. The reaction solution was extracted with 800mL of dichloromethane, washed with ammonia solution, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain a crude product, which was recrystallized from a mixed solvent of toluene 600mL-methanol 600mL to obtain 91.2g of an off-white powder with a yield of 80.9 %, content 99.5%.

Embodiment 3

[0028] Add 246.1g (1mol) of 2-bromocarbazole, 140.0g (0.5mol) of 3-iodobiphenyl, 8.3g (0.05mol) of potassium iodide, hydrogen phosphate Dipotassium 870.1g (5mol), then add 1L N-methylpyrrolidone. After being protected by argon, 190.7 g (0.1 moL) of cuprous 2-thiophenecarboxylate was added, the reaction temperature was controlled at 120° C., and mechanical stirring at constant temperature was continued for 24 hours. After the reaction was detected by high performance liquid chromatography, water was added to terminate the reaction. The reaction solution was extracted with 3L of dichloromethane, washed with ammonia solution, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain a crude product, which was recrystallized from a mixed solvent of 1.4L of toluene-1.4L of methanol to obtain 233.3g of an off-white powder. The rate is 82.8%, and the content is 99.1%.

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Abstract

The invention discloses 9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-dicarbazole and a synthesis method thereof, and belongs to the field of organic chemical synthesis. The 9-([1,1'-biphenyl]-3-yl)-2'-bromine-2,9'-dicarbazole is implemented by the following method: 2-bromocarbazole and 3-iodine biphenyl are used as raw materials, N-methylpyrrolidone is used as a solvent, dipotassium phosphate is used asan acid-binding agent, 2-cuprous thiophene benzoate is used as a catalyst, and the 9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-dicarbazole is synthesized by Ullmann coupling reaction. The process is simple to operate, high in yield and suitable for industrial production. The 9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-dicarbazole can be used in the fields of organic photoelectric materials, medicines and the like.

Description

technical field [0001] The present invention relates to a synthesis method of carbazole derivatives, in particular to a 9-([1,1'-biphenyl]-3-yl)-2'-bromo-2,9'-bicarbazole and a synthesis method thereof , belongs to the field of organic chemical synthesis. Background technique [0002] Due to its incomparable advantages and huge application potential in the new generation of flat panel display technology and solid-state lighting, organic electroluminescent devices have attracted widespread attention in the fields of academia and electronic technology. As one of the components of the device, the material of the hole transport layer strengthens the injection of holes from the anode to the light-emitting layer, and plays an important role in improving the performance of the device. Carbazole is a nitrogen-containing aromatic heterocycle with a special rigid fused ring structure, which is easy to form relatively stable positive ions. It has a large conjugated system and strong ...

Claims

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Application Information

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IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 屈凤波李瑞李奎杨振强陈辉杨瑞娜杨霞席振峰
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD