2-(carbazol-9-yl)-4,5-diazafluorenone | 1182844-55-8

• 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-(carbazol-9-yl)-4,5-diazafluorenone
• 英文别名: 5-Carbazol-9-yl-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-8-one；5-carbazol-9-yl-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-8-one
• CAS: 1182844-55-8
• 化学式: C₂₃H₁₃N₃O
• 分子量: 347.376
• InChiKey: CFAPIDYOKLNDEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(carbazol-9-yl)-4,5-diazafluorenone 、 丙二腈 以 二甲基亚砜 为溶剂， 反应 5.0h， 以66%的产率得到2-(2-(carbazol-9-yl)-4,5-diazafluoren-9-ylidene)malononitrile
  参考文献：
  名称：

  One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation–bromination-rearrangement of phenanthroline and its hammer-shaped donor–acceptor organic semiconductors

  摘要：

  An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor acceptor organic semiconductors. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.12.065
• 作为产物：
  描述：

  2-溴-4,5-二氮杂-9-芴酮 、 咔唑 在 copper(l) iodide 、 18-冠醚-6 、 potassium carbonate 作用下， 以 邻二氯苯 为溶剂， 反应 24.0h， 以71%的产率得到2-(carbazol-9-yl)-4,5-diazafluorenone
  参考文献：
  名称：

  一种有机化合物、电致发光材料及其应用

  摘要：

  本发明提供一种有机化合物、电致发光材料及其应用，所述有机化合物具有如式I所示结构，通过螺环母核结构的设计和特定取代基的引入，可以防止材料堆叠，降低分子的结晶性；螺环结构及取代基的设计使其具有高的三线态能级T1，氮杂环及其连接基团使所述有机化合物具备较好的电子传输和空穴传输特性；而且HOMO和LUMO能级适宜，有利于和相邻层进行能级的搭配；玻璃化转变温度高，分子热稳定性好；能够有效提高器件的发光效率和工作寿命。所述有机化合物作为电致发光材料可用于OLED器件的发光层、空穴阻挡层或电子阻挡层，尤其适于作为磷光主体材料应用于发光层中，能够显著提高器件的发光性能，延长器件的工作寿命。

  公开号：

  CN112321587B

文献信息

• 一种有机化合物、电致发光材料及其应用
  申请人：武汉天马微电子有限公司

  公开号：CN112321587B

  公开（公告）日：2022-02-18

  本发明提供一种有机化合物、电致发光材料及其应用，所述有机化合物具有如式I所示结构，通过螺环母核结构的设计和特定取代基的引入，可以防止材料堆叠，降低分子的结晶性；螺环结构及取代基的设计使其具有高的三线态能级T1，氮杂环及其连接基团使所述有机化合物具备较好的电子传输和空穴传输特性；而且HOMO和LUMO能级适宜，有利于和相邻层进行能级的搭配；玻璃化转变温度高，分子热稳定性好；能够有效提高器件的发光效率和工作寿命。所述有机化合物作为电致发光材料可用于OLED器件的发光层、空穴阻挡层或电子阻挡层，尤其适于作为磷光主体材料应用于发光层中，能够显著提高器件的发光性能，延长器件的工作寿命。
• ORGANIC COMPOUND, ELECTROLUMINESCENT MATERIAL, AND APPLICATION THEREOF
  申请人：SHANGHAI TIANMA AM-OLED CO., LTD.

  公开号：US20210147442A1

  公开（公告）日：2021-05-20

  Provided are an organic compound, an electroluminescent material and an application thereof. The organic compound has a structure represented by Formula I. With the design of the spiro parent structure and the introduction of specific substituents, the organic compound can prevent materials from stacking and reduce the crystallinity of the molecule. The design of the spiro structure and substituents make the organic material have a high triplet state energy level Ti, and the nitrogen heterocycle and its linking groups make the organic compound have characteristics of good electron and hole transport performances. The organic compound has suitable HOMO and LUMO energy levels, facilitating the coordination of adjacent layers in terms of energy level. The organic compound also has advantages of high glass-transition temperature and good molecular thermal stability. Therefore, the organic compound can effectively improve the light emitting efficiency and lifetime of the device.
• One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation–bromination-rearrangement of phenanthroline and its hammer-shaped donor–acceptor organic semiconductors
  作者：Jian-Feng Zhao、Lin Chen、Peng-Ju Sun、Xiao-Ya Hou、Xiang-Hua Zhao、Wei-Jie Li、Ling-Hai Xie、Yan Qian、Nai-En Shi、Wen-Yong Lai、Qu-Li Fan、Wei Huang

  DOI：10.1016/j.tet.2010.12.065

  日期：2011.3

  An unexpected one-pot tandem procedure of 2-bromo-4,5-diazafluoren-9-one starting from phenanthroline with a yield of up to 50% has been described. The conversion mechanism involves three consecutive oxidation, bromination, and rearrangement reactions. A series of its hammer-shaped donor acceptor organic semiconductors with solvent-dependent fluorescence have also been constructed via Ullman and/or Friedel Crafts reaction. Diazafluorenes (DAFs) and derivatives are regarded as promising building blocks or candidates for donor acceptor organic semiconductors. (C) 2011 Published by Elsevier Ltd.