4’-bromo-N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-1,1’-biphenyl-4-amine | 1443670-92-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4’-bromo-N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-1,1’-biphenyl-4-amine
• 英文别名: 4-(4-bromophenyl)-N,N-bis[4-(3,6-ditert-butylcarbazol-9-yl)phenyl]aniline
• CAS: 1443670-92-5
• 化学式: C₆₄H₆₄BrN₃
• 分子量: 955.136
• InChiKey: ZOIFWENURJUMGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.3
• 重原子数：
  68
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,7-双(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)-2,1,3-苯并噻二唑 、 4’-bromo-N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-1,1’-biphenyl-4-amine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到4-[4-[4-[4-[4-[4-(3,6-ditert-butylcarbazol-9-yl)-N-[4-(3,6-ditert-butylcarbazol-9-yl)phenyl]anilino]phenyl]phenyl]-2,1,3-benzothiadiazol-7-yl]phenyl]-N,N-bis[4-(3,6-ditert-butylcarbazol-9-yl)phenyl]aniline
  参考文献：
  名称：

  Bis(carbazol-9-ylphenyl)aniline End-Capped Oligoarylenes as Solution-Processed Nondoped Emitters for Full-Emission Color Tuning Organic Light-Emitting Diodes

  摘要：

  A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling, reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end cap, we are able to reduce the crystallization and retain the high emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of pi-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole. As a result, their emission spectra measured in solution and thin films can cover the full UV-vis spectrum (426-644 nm). Remarkably, solution-processed nondoped BCPA-Ars-based OLEDs could show moderate to excellent device performance with emission colors spanning the whole visible spectrum (deep blue to red). Particularly, the RGB (red, green, blue) OLEDs exhibit good color purity close to the pure RGB colors. This report offers a practical approach for both decorating the highly efficient but planar fluorophores and tuning their emission colors to be suitable for applications in nondoped and solution-processable full-color emission OLEDs.

  DOI：

  10.1021/jo4008332
• 作为产物：
  描述：

  N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-4-iodoaniline 、 4-溴苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到4’-bromo-N,N-bis(4-(3,6-di-tert-butylcarbazol-9-yl)phenyl)-1,1’-biphenyl-4-amine
  参考文献：
  名称：

  Bis(carbazol-9-ylphenyl)aniline End-Capped Oligoarylenes as Solution-Processed Nondoped Emitters for Full-Emission Color Tuning Organic Light-Emitting Diodes

  摘要：

  A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling, reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end cap, we are able to reduce the crystallization and retain the high emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of pi-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole. As a result, their emission spectra measured in solution and thin films can cover the full UV-vis spectrum (426-644 nm). Remarkably, solution-processed nondoped BCPA-Ars-based OLEDs could show moderate to excellent device performance with emission colors spanning the whole visible spectrum (deep blue to red). Particularly, the RGB (red, green, blue) OLEDs exhibit good color purity close to the pure RGB colors. This report offers a practical approach for both decorating the highly efficient but planar fluorophores and tuning their emission colors to be suitable for applications in nondoped and solution-processable full-color emission OLEDs.

  DOI：

  10.1021/jo4008332

文献信息

• Bis(carbazol-9-ylphenyl)aniline End-Capped Oligoarylenes as Solution-Processed Nondoped Emitters for Full-Emission Color Tuning Organic Light-Emitting Diodes
  作者：Tanika Khanasa、Narid Prachumrak、Rattanawaree Rattanawan、Siriporn Jungsuttiwong、Tinnagon Keawin、Taweesak Sudyoadsuk、Thawatchai Tuntulani、Vinich Promarak

  DOI：10.1021/jo4008332

  日期：2013.7.5

  A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling, reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end cap, we are able to reduce the crystallization and retain the high emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of pi-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole. As a result, their emission spectra measured in solution and thin films can cover the full UV-vis spectrum (426-644 nm). Remarkably, solution-processed nondoped BCPA-Ars-based OLEDs could show moderate to excellent device performance with emission colors spanning the whole visible spectrum (deep blue to red). Particularly, the RGB (red, green, blue) OLEDs exhibit good color purity close to the pure RGB colors. This report offers a practical approach for both decorating the highly efficient but planar fluorophores and tuning their emission colors to be suitable for applications in nondoped and solution-processable full-color emission OLEDs.