2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole | 1256943-90-4

• 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
• 英文名称: 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole
• 英文别名: 2,7-Bis(3,6-ditert-butylcarbazol-9-yl)-9-phenylcarbazole
• CAS: 1256943-90-4
• 化学式: C₅₈H₅₉N₃
• 分子量: 798.127
• InChiKey: JNUHIGMYFXFZGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  61
• 可旋转键数：
  7
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  14.8
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,7-二溴咔唑 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 1,10-菲罗啉 、 三叔丁基膦 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole
  参考文献：
  名称：

  High-triplet-energy tri-carbazole derivatives as host materials for efficient solution-processed blue phosphorescent devices

  摘要：

  一种新型的可溶液加工的基于咔唑的主材料，包括3,6-bis(N-carbazolyl)-N-phenylcarbazole (BCC-36)、3,6-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-36)、2,7-bis(N-carbazolyl)-N-phenylcarbazole (BCC-27)和2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-27)，被设计和合成。由于高度扭曲的构型，这些主材料展现出高的三重态能级（2.90–3.02 eV）和高的玻璃转变温度（147–210 °C）。它们还表现出合适的HOMO能级（−5.21–−5.36 eV），从而改善了载流子的注入特性。这些新化合物用于制造磷光有机发光二极管（OLED），作为与铱(III) bis(4,6-difluorophenylpyridinato)-picolinate（FIrpic）和铱(III) bis(4′,6′-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borate（FIr6）掺杂的主材料，通过旋涂工艺制备。基于FIrpic的蓝光发射器件的最佳性能具有较低的开启电压为3.9 V，最高效率为27.2 cd A−1（11.8 lm W−1），以及最大外量子效率为14.0%。此外，基于FIr6的深蓝光发射器件的最佳性能表现为启动电压4.9 V，最高效率为11.5 cd A−1（4.9 lm W−1），以及最大外量子效率为6.8%。这些性能数据在溶液加工的蓝色磷光OLED中表现突出。

  DOI：

  10.1039/c0jm03365k

文献信息

• METHOD FOR PURIFYING ORGANIC MATERIAL, MATERIAL FOR ORGANIC ELECTRONICS, PHOTOELECTRIC CONVERSION DEVICE, OPTICAL SENSOR, IMAGING DEVICE, AND ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：FUJIFILM CORPORATION

  公开号：US20140042411A1

  公开（公告）日：2014-02-13

  Provided is a method for purifying an organic material having a 10% weight reduction temperature of 250° C. or more as measured by thermogravimetry at a vacuum degree of 1×10 −2 Pa or less, which may sublime and purify the organic material having high heat resistance at high sublimation temperature with high purity and high yield in a short period of time, in which the organic material is subjected sublimation purification after a concentration of inorganic impurities in the organic material is adjusted to 5,000 ppm or less.
• ORGANIC MATERIAL FOR DEPOSITION, AND ORGANIC PHOTOELECTRIC CONVERSION ELEMENT, IMAGING ELEMENT, DEPOSITION METHOD, AND MANUFACTURING METHOD FOR ORGANIC PHOTOELECTRONIC ONVERSION ELEMENT OBTAINED USING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150129861A1

  公开（公告）日：2015-05-14

  An organic material for deposition that is used for dry deposition of an organic layer included in an organic photoelectric conversion element is provided in which the organic material contains an organic composition of the organic layer as a principal component, and a residual solvent content of the organic material for deposition is equal to or less than 3 mol %.
• US9085537B2
  申请人：——

  公开号：US9085537B2

  公开（公告）日：2015-07-21
• High-triplet-energy tri-carbazole derivatives as host materials for efficient solution-processed blue phosphorescent devices
  作者：Wei Jiang、Lian Duan、Juan Qiao、Guifang Dong、Deqiang Zhang、Liduo Wang、Yong Qiu

  DOI：10.1039/c0jm03365k

  日期：——

  A novel series of solution-processible carbazole-based host materials, 3,6-bis(N-carbazolyl)-N-phenylcarbazole (BCC-36), 3,6-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-36), 2,7-bis(N-carbazolyl)-N-phenylcarbazole (BCC-27), and 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-27), is designed and synthesized. Owing to the highly twisted configuration, these hosts exhibit high triplet energy levels (2.90–3.02 eV) and high glass transition temperatures (147–210 °C). They also exhibit appropriate HOMO energy levels (−5.21–−5.36 eV), resulting in an improved hole-injection property. These novel compounds are employed to fabricate phosphorescent organic lighting-emitting diodes (OLEDs) as the host materials doped with the guests of iridium(III) bis(4,6-difluorophenylpyridinato)-picolinate (FIrpic) and iridium(III) bis(4′,6′-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borate (FIr6) by spin coating. The best device performance of FIrpic based blue-emitting devices has a rather low turn-on voltage of 3.9 V, a maximum efficiency of 27.2 cd A−1 (11.8 lm W−1), and a maximum external quantum efficiency of 14.0%. Moreover, the best device performance of FIr6 based deep-blue-emitting devices exhibits a turn-on voltage of 4.9 V, a maximum efficiency of 11.5 cd A−1 (4.9 lm W−1), and a maximum external quantum efficiency 6.8%. The performance data are outstanding for solution-processed blue phosphorescent OLEDs.

  一种新型的可溶液加工的基于咔唑的主材料，包括3,6-bis(N-carbazolyl)-N-phenylcarbazole (BCC-36)、3,6-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-36)、2,7-bis(N-carbazolyl)-N-phenylcarbazole (BCC-27)和2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-27)，被设计和合成。由于高度扭曲的构型，这些主材料展现出高的三重态能级（2.90–3.02 eV）和高的玻璃转变温度（147–210 °C）。它们还表现出合适的HOMO能级（−5.21–−5.36 eV），从而改善了载流子的注入特性。这些新化合物用于制造磷光有机发光二极管（OLED），作为与铱(III) bis(4,6-difluorophenylpyridinato)-picolinate（FIrpic）和铱(III) bis(4′,6′-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borate（FIr6）掺杂的主材料，通过旋涂工艺制备。基于FIrpic的蓝光发射器件的最佳性能具有较低的开启电压为3.9 V，最高效率为27.2 cd A−1（11.8 lm W−1），以及最大外量子效率为14.0%。此外，基于FIr6的深蓝光发射器件的最佳性能表现为启动电压4.9 V，最高效率为11.5 cd A−1（4.9 lm W−1），以及最大外量子效率为6.8%。这些性能数据在溶液加工的蓝色磷光OLED中表现突出。