9,9'-(1,4-苯基)二-9H-咔唑 | 19287-68-4

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 9,9'-(1,4-苯基)二-9H-咔唑
• 英文名称: 1,4-di(9H-carbazol-9-yl)benzene
• 英文别名: 1,4-bis(N-carbazolyl)benzene；1,4-bis(carbazol-9-yl)benzene；bis(carbazol-9-yl)phenylene；9-(4-carbazol-9-ylphenyl)carbazole
• CAS: 19287-68-4
• 化学式: C₃₀H₂₀N₂
• 分子量: 408.502
• InChiKey: FPMQTZDVSUPPCB-UHFFFAOYSA-N

物化性质

• 熔点：
  319-321 °C
• 沸点：
  626.9±51.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9,9'-(1,4-苯基)二-9H-咔唑 在 potassium iodate 、 溶剂黄146 、 potassium iodide 作用下， 反应 10.0h， 以75%的产率得到1,4-bis(3,6-diiodo-9H-carbazol-9-yl)benzene
  参考文献：
  名称：

  Isotropic rotation in amphidynamic crystals of stacked carbazole-based rotors featuring halogen-bonded stators

  摘要：

  在具有周边卤键的晶体分子转子中发现了1,4-苯基的固态各向同性旋转。

  DOI：

  10.1039/c6cc07379d
• 作为产物：
  描述：

  1,4-二溴苯 在 copper(l) iodide 、 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 69.0h， 生成 9,9'-(1,4-苯基)二-9H-咔唑
  参考文献：
  名称：

  Novel Organic Semiconductors Based on Phenyl and Phenylthienyl Derivatives for Organic Thin-Film Transistors

  摘要：

  New phenyl and phenylthienyl derivatives end-functionalized with carbazole and a-carboline, 9-(4(9-H-carbazol-9-yl)phenyl)-9H-carbazole, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-pyrido[2,3-b]indole, 9(3-(9H-carbazol-9-yl)pheny1)-9H-carbazole, 9-(3-(9H-carbazol-9-yl)pheny1)-9H-pyrido[2,3-b]indole, 9-(4-(5-(9H-carbazol-9-yl)thiophen-2-yl)phenyl)-9H-carbazole, and 9-(3-(5-(9H-carbazol-9-yl) thiophen-2-yl)phenyl)-9H-carbazole were synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). Most compounds exhibited p-channel characteristics with carrier mobility as high as 1.7 x 10(-5) cm(2)Ns and a current on/off ratio of 10(2)-10(4) for top-contact/bottom-gate OTFT devices.

  DOI：

  10.1166/jnn.2016.10748

文献信息

• An Efficient Synthesis of<i>N</i>-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and<i>N</i>-Carbazolylmagnesium Chloride
  作者：Yuji Nakayama、Naota Yokoyama、Hideki Nara、Tohru Kobayashi、Mitsuhiko Fujiwhara

  DOI：10.1002/adsc.201500301

  日期：2015.7.6

  under mild conditions (110 °C) in a short period of time (15 min to 2 h) to give N‐(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N‐(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light‐emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min

  报道了一种用于合成N-（杂）芳基咔唑（一种对功能材料有用的化合物）的有效方法。各种（杂）芳基氯化物与氯化N-咔唑基氯化镁在烯丙基氯化钯（II）二聚体[[PdCl（烯丙基）] 2 }和二叔丁基（ 2,2-二苯基-1-甲基环丙烷-1-基）膦（cBRIDP）在温和条件下（110°C）在短时间内（15分钟至2小时）以高收率得到N-（杂）芳基咔唑。进行溴氯苯的反应有利于溴基团生成N-（氯苯基）咔唑的选择性很高。通过（杂）芳基多卤化物的反应，还可以在15分钟内以高收率获得用于有机发光二极管的功能材料，例如mCP，26mCPy，CBP和TCB。还讨论了反应条件的优化和假定的反应催化周期。
• Transition-Metal-Free Synthesis of Carbazoles and Indoles by an S_NAr-Based “Aromatic Metamorphosis” of Thiaarenes
  作者：M. Bhanuchandra、Kei Murakami、Dhananjayan Vasu、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/anie.201503671

  日期：2015.8.24

  dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The “aromatic metamorphosis” of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron‐deficient thiaarene dioxides exhibit interesting reactivity

  通过母体二苯并噻​​吩的氧化容易制备的二苯并噻吩二氧化物在一次操作中在分子内然后在分子内经历苯胺的亲核芳香取代，然后生成分子内相应的咔唑。二苯并噻吩向咔唑的“芳香变形”不需要任何重金属。该策略也适用于吲哚的合成。由于缺电子的硫杂芳烃二氧化物表现出有趣的反应性，而相应的富电子氮杂芳烃则未观察到，因此，二氧化硫杂ar特定反应与基于S N Ar的芳族变态反应的结合，使得无过渡金属的结构成为可能。难以制备咔唑。
• HETEROCYCLIC COMPOUND FOR USE IN ELECTRONIC DEVICES
  申请人：Merck Patent GmbH

  公开号：US20210363159A1

  公开（公告）日：2021-11-25

  The present invention relates to heterocyclic compounds, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.

  本发明涉及杂环化合物，特别是用于电子设备。该发明还涉及制备本发明化合物的方法以及包含这些化合物的电子设备。
• Three carbazole-based host materials: facile synthesis, photophysical properties and performances in PhOLED
  作者：Tingting Yang、Huixia Xu、Bo Zhao、Peng Tao、Peng Sun、Hua Wang、Bingshe Xu、Wai-Yeung Wong

  DOI：10.1016/j.tet.2016.10.044

  日期：2016.12

  Three host materials based on the carbazole were designed and facilely synthesized, i. e., 9-(6-(9-carbazolyl)hexyl)carbazole (hCP), 9-(4-(2-thiophene-based)phenyl) carbazole (sCP) and 9-(4-(9-carbazolyl)phenyl)carbazole(pCP). The relationships between the structures and photophysical, electrochemical and electrophosphorescent performances were investigated. Their emission peaks are located in UV region

  设计并轻松合成了三种基于咔唑的主体材料，即9-（6-（9-咔唑基）己基）咔唑（hCP），9-（4-（2-噻吩基）苯基）咔唑（sCP）和9-（4-（9-咔唑基）苯基）咔唑（pCP）。研究了结构与光物理，电化学和电致磷光性能之间的关系。它们的发射峰位于UV区，光学带隙分别为3.51、3.57和3.89 eV。因此，它们可用作磷光有机发光器件（PhOLED）中的主体。通过在主体中掺杂三（2-苯基吡啶）铱（Ir（ppy）3）作为发光材料来制造PHOLED 。采用sCP作为基质的PhOLED的最大电流效率为44.88 cd / A。
• POLYCYCLIC AROMATIC COMPOUND AND LIGHT EMISSION LAYER-FORMING COMPOSITION
  申请人：Kwansei Gakuin Educational Foundation

  公开号：US20180094000A1

  公开（公告）日：2018-04-05

  The objective of the invention is to provide a polycyclic aromatic compound in which solubility to a solvent, film formability, wet coatability, thermal stability, and in-plane orientation are improved. This objective is achieved by a light emission layer-forming composition comprising: as a first component, at least one type of dopant material selected from the group consisting of polycyclic aromatic compounds represented by general formula (A) and polycyclic aromatic oligomer compounds including a plurality of structures represented by general formula (A); as a second component, a specific low-molecular-weight host material; and, as a third component, at least one type of organic solvent. In formula (A), ring A, ring B, and ring C each independently represent an aryl ring or a hetero aryl ring, Y 1 is B, and X 1 and X 2 each independently represent O or N—R wherein at least one of X 1 and X 2 is N—R.

  该发明的目的是提供一种多环芳香化合物，其溶解性、膜形成性、湿涂性、热稳定性和平面取向性得到改善。通过包括以下组分的发光层形成组合物实现这一目标：作为第一组分，至少一种从一般式（A）表示的多环芳香化合物和包括多个从一般式（A）表示的结构的多环芳香寡聚物化合物中选择的掺杂材料；作为第二组分，特定的低分子量载体材料；作为第三组分，至少一种有机溶剂。在式（A）中，环A、环B和环C分别独立表示芳基环或杂环芳基环，Y1是B，X1和X2分别独立表示O或N—R，其中X1和X2中至少一个是N—R。