9-(dicyanomethylene)-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile | 489402-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 9-(dicyanomethylene)-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile
• 英文别名: 9-(Dicyanomethylidene)indeno[1,2-b]pyrazine-2,3-dicarbonitrile
• CAS: 489402-93-9
• 化学式: C₁₆H₄N₆
• 分子量: 280.248
• InChiKey: VIQMVMWFDHETIL-UHFFFAOYSA-N

物化性质

• 沸点：
  582.1±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苝 、 9-(dicyanomethylene)-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile 以 氯苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  分子重排的共晶工程：高性能 N 型有机半导体的“开启”方法

  摘要：

  开发新型高性能 n 型半导体对于未来的有机电子学非常重要。新的缺电子骨架或化学修饰以控制能级和电子传输路线的复杂合成程序限制了它们的应用。在这里，使用 PAH 供体掺杂，我们报告了基于 TCAF 的复合物的两种多晶型物作为源自非活性原始材料的高效 n 型半导体。这些超分子结构沿混合 π-π 堆积方向具有不同的供体-受体重叠，摩尔比为 1:1。在可控溶剂处理下，基底上微晶的完全相变也可能发生。结果，电子迁移率从 0.06 到 0.88 cm 2 V -1的大转变由于相变，观察到s -1。量子计算证实，包含更好重叠的多态结构允许比扭曲重叠更大的转移积分。二元超分子体系的电荷传输特性与分子取向高度相关。这种相位控制的共晶工程方法为我们提供了对高性能 n 型有机半导体探索的新见解。

  DOI：

  10.1039/d1tc01441b
• 作为产物：
  描述：

  水合茚三酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 9-(dicyanomethylene)-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Material for an organic electroluminescence device and an organic electroluminescence device

  摘要：

  以下是有机电致发光装置的材料，其化学式如下（I）：其中X1是以下（a）到（e）中表示的二价基团之一；Y1到Y4独立地是碳原子或氮原子；而R1到R4独立地是氢原子、烷基、取代或未取代芳基、取代或未取代杂环、卤素原子、氟烷基或氰基，或者R1和R2以及R3和R4独立地结合形成取代或未取代芳环或取代或未取代杂环。

  公开号：

  US08119828B2

文献信息

• Green-synthesized, low-cost tetracyanodiazafluorene (TCAF) as electron injection material for organic light-emitting diodes
  作者：Bing Yang、Jianfeng Zhao、Zepeng Wang、Zhenlin Yang、Zongqiong Lin、Yanni Zhang、Jiewei Li、Linghai Xie、Zhongfu An、Hongmei Zhang、Jiena Weng、Wei Huang

  DOI：10.1016/j.cclet.2019.08.054

  日期：2019.11

  Two electron-deficient azaacenes including di- and tetra-cyanodiazafluorene (DCAF and TCAF) with the advantages of deep lowest unoccupied molecular orbital (LUMO), green-synthesis, low-cost, simply purification method, excellent yields have been obtained, characterized and used as electron injection materials (ElMs) in three groups of electroluminescence devices. Device B with TCAF as EIM exhibited the best performance including turn-on voltage of 5.0 V, stronger maximum luminance intensity of 31,549 cd/m(2), higher luminance efficiency of 62.34 cd/A and larger power efficiency of 21.74 lm/W which are 0.53, 6.7, 9.3 and 15.3 times than that of device A with DCAF as ElMs, respectively. The enhanced interfacial electron injection ability of TCAF than that of DCAF is supported by its better electron mobility in electron-only device, deeper LUMO (-4.52 eV), and stronger electronic affinity. Best external quantum efficiency of 16.56% was achieved with optimized thicknesses of TCAF as EIM and TPBi as electron transporting layer. As a new corner of acceptor family, TCAF would push forward organic electronics with more fascinating and significant applications. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• MATERIAL FOR AN ORGANIC ELECTROLUMINESCENCE DEVICE AND AN ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：Morishita Hironobu

  公开号：US20100044686A1

  公开（公告）日：2010-02-25

  A material for an organic electroluminescence device represented by the following formula (I): wherein X 1 is one of divalent groups represented by the following (a) to (e); Y 1 to Y 4 are independently a carbon atom or a nitrogen atom; and R 1 to R 4 are independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocycle, a halogen atom, a fluoroalkyl group or a cyano group, or R 1 and R 2 , and R 3 and R 4 are independently bonded to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle.
• US8119828B2
  申请人：——

  公开号：US8119828B2

  公开（公告）日：2012-02-21
• Material for an organic electroluminescence device and an organic electroluminescence device
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：US08119828B2

  公开（公告）日：2012-02-21

  A material for an organic electroluminescence device represented by the following formula (I): wherein X1 is one of divalent groups represented by the following (a) to (e); Y1 to Y4 are independently a carbon atom or a nitrogen atom; and R1 to R4 are independently a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocycle, a halogen atom, a fluoroalkyl group or a cyano group, or R1 and R2, and R3 and R4 are independently bonded to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle.

  以下是有机电致发光装置的材料，其化学式如下（I）：其中X1是以下（a）到（e）中表示的二价基团之一；Y1到Y4独立地是碳原子或氮原子；而R1到R4独立地是氢原子、烷基、取代或未取代芳基、取代或未取代杂环、卤素原子、氟烷基或氰基，或者R1和R2以及R3和R4独立地结合形成取代或未取代芳环或取代或未取代杂环。
• Cocrystal engineering of molecular rearrangement: a “turn-on” approach for high-performance N-type organic semiconductors
  作者：Wei Wang、Lixing Luo、Zongqiong Lin、Zifeng Mu、Zhengkun Ju、Bo Yang、Yang Li、Menglu Lin、Guankui Long、Jing Zhang、Jianfeng Zhao、Wei Huang

  DOI：10.1039/d1tc01441b

  日期：——

  novel high-performance n-type semiconductors is of great importance for future organic electronics. Complicated synthesizing procedures of new electron deficient backbones or chemical modification to control the energy level and electron transport route limit their applications. Here, using PAH donor doping, we report that two polymorphs of TCAF based complexes act as efficient n-type semiconductors originating

  开发新型高性能 n 型半导体对于未来的有机电子学非常重要。新的缺电子骨架或化学修饰以控制能级和电子传输路线的复杂合成程序限制了它们的应用。在这里，使用 PAH 供体掺杂，我们报告了基于 TCAF 的复合物的两种多晶型物作为源自非活性原始材料的高效 n 型半导体。这些超分子结构沿混合 π-π 堆积方向具有不同的供体-受体重叠，摩尔比为 1:1。在可控溶剂处理下，基底上微晶的完全相变也可能发生。结果，电子迁移率从 0.06 到 0.88 cm 2 V -1的大转变由于相变，观察到s -1。量子计算证实，包含更好重叠的多态结构允许比扭曲重叠更大的转移积分。二元超分子体系的电荷传输特性与分子取向高度相关。这种相位控制的共晶工程方法为我们提供了对高性能 n 型有机半导体探索的新见解。