1,5-bis[(4-hexylphenyl)methyl]-3,7-diphenyl-2,6-bis[4-(N,N-diphenyamino)phenyl]benzo[1,2-b:4,5-b']dipyrrole | 1210481-00-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,5-bis[(4-hexylphenyl)methyl]-3,7-diphenyl-2,6-bis[4-(N,N-diphenyamino)phenyl]benzo[1,2-b:4,5-b']dipyrrole
• 英文别名: 4-[1,5-bis[(4-hexylphenyl)methyl]-3,7-diphenyl-2-[4-(N-phenylanilino)phenyl]pyrrolo[2,3-f]indol-6-yl]-N,N-diphenylaniline
• CAS: 1210481-00-7
• 化学式: C₈₄H₇₈N₄
• 分子量: 1143.57
• InChiKey: MDKCXSBNZROELQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.2
• 重原子数：
  88
• 可旋转键数：
  24
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  16.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-bis[(4-hexylphenyl)methyl]-3,7-diphenyl-2,6-bis[4-(N,N-diphenyamino)phenyl]benzo[1,2-b:4,5-b']dipyrrole 在 aluminum (III) chloride 、 苯甲醚 作用下， 以56%的产率得到2,6-bis(4-(N,N-diphenylamino)phenyl)-3,7-diphenylbenzo[1,2-b:4,5-b']dipyrrole
  参考文献：
  名称：

  Hexaaryl-benzodipyrroles: Properties and Application as Amorphous Carrier-Transporting Materials

  摘要：

  We have newly synthesized 1,2,3,5,6,7-hexaarylbenzo-[1,2-b:4,5-b']dipyrroles (HABDPs) and studied their properties. The HABDPs showed UV absorption maxima at 377-390 nm, indicating their extended pi-conjugation system. They were also found to serve as efficient amorphous materials, featuring high electrochemical and thermal stability with high carrier mobility of up to 10(-3) cm(2)/Vs using the time-of-flight technique. Application of the HABDPs to organic light-emitting diodes resulted in significantly improved performance in driving voltage and efficiency compared with alpha-NPD, a commonly used hole-transporting material.

  DOI：

  10.3987/com-14-s(k)16
• 作为产物：
  描述：

  碘苯 、 N,N'-bis[(4-hexylphenyl)methyl]-2,5-bis[(N,N-diphenylamino)phenylethynyl]benzene-1,4-diamine 在 正丁基锂 、 zinc(II) chloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三叔丁基膦 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 N-甲基吡咯烷酮 为溶剂， 反应 22.0h， 以27%的产率得到1,5-bis[(4-hexylphenyl)methyl]-3,7-diphenyl-2,6-bis[4-(N,N-diphenyamino)phenyl]benzo[1,2-b:4,5-b']dipyrrole
  参考文献：
  名称：

  四芳基取代的苯并[1,2-b：4,5-b']双吡咯：OLED器件中的空穴注入材料的合成，性质和应用

  摘要：

  是的，HIM可以！使用锌介导的双环化反应合成了一系列2,3,6,7-四芳基苯并[1,2- b：4,5- b ']双吡咯（BDP）。由BDP：PPB构成的有机发光二极管作为空穴注入层的电压可以低于基于PEDOT：PSS的器件的电压。IP值与驱动电压的相关性为空穴注入过程的机理提供了一些启示。

  DOI：

  10.1002/asia.200800471

文献信息

• Tetraaryl-Substituted Benzo[1,2-<i>b</i>:4,5-<i>b</i>′]dipyrroles: Synthesis, Properties, and Applications to Hole-Injection Materials in OLED Devices
  作者：Hayato Tsuji、Yuki Yokoi、Chikahiko Mitsui、Laurean Ilies、Yoshiharu Sato、Eiichi Nakamura

  DOI：10.1002/asia.200800471

  日期：2009.5.4

  Yes, HIMs can! A series of 2,3,6,7‐tetraarylbenzo[1,2‐b:4,5‐b′]dipyrroles (BDPs) were synthesized using zinc‐mediated double cyclization. Organic light‐emitting diodes consisting of BDP:PPB as a hole‐injection layer could be driven at a lower voltage than a PEDOT:PSS‐based device. Correlation of the IP values with the driving voltage shed some light on the mechanism of hole‐injection processes.

  是的，HIM可以！使用锌介导的双环化反应合成了一系列2,3,6,7-四芳基苯并[1,2- b：4,5- b ']双吡咯（BDP）。由BDP：PPB构成的有机发光二极管作为空穴注入层的电压可以低于基于PEDOT：PSS的器件的电压。IP值与驱动电压的相关性为空穴注入过程的机理提供了一些启示。
• Hexaaryl-benzodipyrroles: Properties and Application as Amorphous Carrier-Transporting Materials
  作者：Eiichi Nakamura、Hayato Tsuji、Yuki Yokoi、Shunsuke Furukawa

  DOI：10.3987/com-14-s(k)16

  日期：——

  We have newly synthesized 1,2,3,5,6,7-hexaarylbenzo-[1,2-b:4,5-b']dipyrroles (HABDPs) and studied their properties. The HABDPs showed UV absorption maxima at 377-390 nm, indicating their extended pi-conjugation system. They were also found to serve as efficient amorphous materials, featuring high electrochemical and thermal stability with high carrier mobility of up to 10(-3) cm(2)/Vs using the time-of-flight technique. Application of the HABDPs to organic light-emitting diodes resulted in significantly improved performance in driving voltage and efficiency compared with alpha-NPD, a commonly used hole-transporting material.