5,5-二(9-甲基-9H-咔唑-3-基)-5H-环戊二烯并[2,1-b:3,4-b']二吡啶 | 1359755-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5,5-二(9-甲基-9H-咔唑-3-基)-5H-环戊二烯并[2,1-b:3,4-b']二吡啶
• 英文名称: 9,9-bis(9-methylcarbazol-3-yl)-4,5-diazafluorene
• 英文别名: 5,5-Bis(9-methyl-9H-carbazol-3-yl)-5H-cyclopenta[2,1-b:3,4-b']dipyridine；8,8-bis(9-methylcarbazol-3-yl)-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene
• CAS: 1359755-87-5
• 化学式: C₃₇H₂₆N₄
• 分子量: 526.64
• InChiKey: HOHBMXOHHGOCGR-UHFFFAOYSA-N

物化性质

• 熔点：
  384℃

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  41
• 可旋转键数：
  2
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基咔唑 、 4,5-二氮芴-9-酮 在 eaton’s reagent 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到5,5-二(9-甲基-9H-咔唑-3-基)-5H-环戊二烯并[2,1-b:3,4-b']二吡啶
  参考文献：
  名称：

  New Ambipolar Hosts Based on Carbazole and 4,5-Diazafluorene Units for Highly Efficient Blue Phosphorescent OLEDs with Low Efficiency Roll-Off

  摘要：

  Two ambipolar host materials, 9,9-bis(9-methylcarbazol-3-yl)-4,5-diazafluorene (MCAF) and 9,9-bis(9-phenylcarbazaol-3-yl)-4,5-diazafluorene (PCAF), comprising two electron-donating carbazole units and an electron-accepting 4,5-diazafluorene group, have been designed, synthesized, and characterized. Given the nonplanar structure of the sp(3)-hybridized C9 atom of the 4,5-diazafluorene unit, MCAF and PCAF exhibit high triplet energy levels of 2.82 and 2.83 eV, as well as high glass-transition temperatures of 187 and 188 C, respectively. Equipped with ambipolar transport properties as well as suitable highest occupied and lowest unoccupied molecular orbital energy levels, the two compounds excellently perform in blue phosphorescent organic light-emitting devices (PHOLEDs). The MCAF-based blue PHOLED has a very low turn-on voltage of 2.6 V, a high current efficiency of 32.2 cd A(-1), a high external quantum efficiency of 17.9%, a high power efficiency of 31.3 Im W-1, and a low efficiency roll-off with a high efficiency of 27.6 cd A(-1) even at 10 000 cd m(-2). These values are among the highest ever reported for devices doped with iridium(III) bis[2-(4',6'-difluorophenyl)pyridinato-N,C(2')]-picolinate.

  DOI：

  10.1021/cm2036647

文献信息

• BIPOLAR COMPOUND AS A HOST MATERIAL FOR ORGANIC LIGHT EMITTING DIODES
  申请人：LEE Chun Sing

  公开号：US20130099207A1

  公开（公告）日：2013-04-25

  The present invention provides a bipolar compound represented by formula (I) and the derivatives thereof as a host material having excellent bipolar transporting properties for organic light-emitting diodes (OLEDs). The present invention also relates to a device including at least a layer of the bipolar compound and/or the derivatives thereof as a host material and a method of making the same.

  本发明提供了一种双极化合物，其表示为公式（I）及其衍生物作为有机发光二极管（OLED）的优异双极传输性能的宿主材料。本发明还涉及包括至少一层双极化合物和/或其衍生物作为宿主材料的器件以及制造该器件的方法。
• US9269908B2
  申请人：——

  公开号：US9269908B2

  公开（公告）日：2016-02-23
• New Ambipolar Hosts Based on Carbazole and 4,5-Diazafluorene Units for Highly Efficient Blue Phosphorescent OLEDs with Low Efficiency Roll-Off
  作者：Cai-Jun Zheng、Jun Ye、Ming-Fai Lo、Man-Keung Fung、Xue-Mei Ou、Xiao-Hong Zhang、Chun-Sing Lee

  DOI：10.1021/cm2036647

  日期：2012.2.28

  Two ambipolar host materials, 9,9-bis(9-methylcarbazol-3-yl)-4,5-diazafluorene (MCAF) and 9,9-bis(9-phenylcarbazaol-3-yl)-4,5-diazafluorene (PCAF), comprising two electron-donating carbazole units and an electron-accepting 4,5-diazafluorene group, have been designed, synthesized, and characterized. Given the nonplanar structure of the sp(3)-hybridized C9 atom of the 4,5-diazafluorene unit, MCAF and PCAF exhibit high triplet energy levels of 2.82 and 2.83 eV, as well as high glass-transition temperatures of 187 and 188 C, respectively. Equipped with ambipolar transport properties as well as suitable highest occupied and lowest unoccupied molecular orbital energy levels, the two compounds excellently perform in blue phosphorescent organic light-emitting devices (PHOLEDs). The MCAF-based blue PHOLED has a very low turn-on voltage of 2.6 V, a high current efficiency of 32.2 cd A(-1), a high external quantum efficiency of 17.9%, a high power efficiency of 31.3 Im W-1, and a low efficiency roll-off with a high efficiency of 27.6 cd A(-1) even at 10 000 cd m(-2). These values are among the highest ever reported for devices doped with iridium(III) bis[2-(4',6'-difluorophenyl)pyridinato-N,C(2')]-picolinate.