3,6-二碘-9-(4-甲基苯基)-9H-咔唑 | 566143-95-1

• 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: 3,6-二碘-9-(4-甲基苯基)-9H-咔唑
• 英文名称: 3,6-diiodo-9-p-tolyl-9H-carbazole
• 英文别名: 9-(4-methyl-phenyl)-3,6-diiodocarbazole；N-(4-tolyl)-3,6-diiodocarbazole；3,6-Diiodo-9-(4-methylphenyl)-9H-carbazole；3,6-diiodo-9-(4-methylphenyl)carbazole
• CAS: 566143-95-1
• 化学式: C₁₉H₁₃I₂N
• 分子量: 509.128
• InChiKey: SCDMBDRGTOJYFM-UHFFFAOYSA-N

物化性质

• 密度：
  1.88

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,6-二碘-9-(4-甲基苯基)-9H-咔唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 18-冠醚-6 、 铜 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 3-Carbazol-9-yl-6-[2-[6-[2-[6-carbazol-9-yl-9-(4-methylphenyl)carbazol-3-yl]ethynyl]pyren-1-yl]ethynyl]-9-(4-methylphenyl)carbazole
  参考文献：
  名称：

  Carbazole–pyrene-based organic emitters for electroluminescent device

  摘要：

  Carbazole-pyrene-based compounds were synthesized and fully characterized. Their photoluminescence properties were studied. Fluorescence quantum yield was improved dramatically by inserting pyrene as electron-acceptor. Blending 9-(3-(2-(1-(2-(3-(9H-carbazol-9-yl)-9-p-tolyl-9H-carbazol-6-yl)ethynyl)pyren-6-yl)ethynyl)-9-p-tolyl-9H-carbazol-6-yl)-9H-carbazole (16) with poly(N-vinylcarbazole) (PVK), simplified electroluminescent (EL) device with green emission was fabricated. Maximum luminance reached 1000 cd/m(2). (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2005.04.019
• 作为产物：
  描述：

  9-(4-甲基苯基)-9H-咔唑 在 potassium iodate 、 potassium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以95%的产率得到3,6-二碘-9-(4-甲基苯基)-9H-咔唑
  参考文献：
  名称：

  N-苯基咔唑及其氧化物种的光物理和光谱电化学研究

  摘要：

  一系列N-苯基咔唑衍生物，即TCz（N-甲苯基咔唑），TCz-TCz（3,3′-连接的二聚体）和CzPh-CH 2 -PhCz（亚甲基桥连的N-苯基咔唑） ），已经通过吸收和荧光光谱，DFT计算，循环伏安法和光谱电化学方法进行了合成和研究。结论是，CzPh-CH 2 -PhCz中的亚甲基桥将两个TCz单元隔离开，而TCz-TCz允许沿两个咔唑扩展电子耦合。此外，TCz-TCz的磷光光谱显示出高能三重态（2.76 eV）。观察到CzPh-CH 2的氧化-PhCz生成电致变色聚合物，其中包含由亚甲基桥分隔的TCz-TCz二聚体单元。通过EPR光谱分析了氧化的TCz-TCz亚基，发现它是Robin and Day分类中的III类混合价离子。所有结果表明这些分子可能适合用作荧光传感中的选择性探针或用作电致发光器件中的主体材料。

  DOI：

  10.1016/j.jphotochem.2018.07.039

文献信息

• N-phenyl triscarbazole
  申请人：Solvay SA

  公开号：EP2433928A1

  公开（公告）日：2012-03-28

  The present invention relates to a novel triscarbazole compound having substituent on N-phenyl, which can be represented by Formula (I). wherein R1 is selected from the group consisting of halogen or alkyl or alkoxy group having 1 to 20 carbon atoms wherein one or more hydrogen atom may be replaced by halogen; RA, RB, Rc, RD and RE are any of substituents; and i, j, k, l and m are same or different at each occurrence and represent an integer from 0 to 4. By introduction of the substituent on N-phenyl, the device efficiency, stability and lifetime can be increased while maintaining the solubility. These compounds can be used in various organic devices such as organic light emitting diodes, photovoltaic cells or organic semiconductor devices.

  本发明涉及一种在N-苯基上具有取代基的新型三咔唑化合物，其可以用式（I）表示。其中R1选自卤素、烷基或含有1至20个碳原子的烷氧基团，其中一个或多个氢原子可被卤素取代；RA、RB、Rc、RD和RE是任意的取代基；i、j、k、l和m在每次出现时相同或不同，并表示从0到4的整数。通过在N-苯基上引入取代基，可以提高器件的效率、稳定性和寿命，同时保持溶解性。这些化合物可用于各种有机器件，如有机发光二极管、光伏电池或有机半导体器件。
• [EN] N-PHENYL TRISCARBAZOLE<br/>[FR] N-PHÉNYL TRISCARBAZOLE
  申请人：SOLVAY

  公开号：WO2012025510A1

  公开（公告）日：2012-03-01

  The present invention relates to a novel triscarbazole compound having substituent on N-phenyl, which can be represented by Formula (I). wherein R1 is selected from the group consisting of hydrogen, halogen or alkyl or alkoxy group having 1 to 20 carbon atoms wherein at least one hydrogen atom is optionally replaced by halogen; RA, RB, RC, RD and RE are any of substituents other than hydrogen wherein at least two of R1 and RA may further form a fused ring; and i, j, k, l and m are same or different at each occurrence and represent an integer from 0 to 4, with the proviso that when R1 is hydrogen, i is not 0. By introduction of the substituent on N-phenyl, the device efficiency, stability and lifetime can be increased while maintaining the solubility. These compounds can be used in various organic devices such as organic light emitting diodes, photovoltaic cells or organic semiconductor devices.

  本发明涉及一种具有N-苯基上取代基的新型三咔唑化合物，可以用化学式（I）表示。其中R1选自氢、卤素或具有1至20个碳原子的烷基或烷氧基组成的基团，其中至少有一个氢原子可以被卤素取代；RA、RB、RC、RD和RE是除氢之外的任何取代基，其中至少有两个R1和RA可以进一步形成融合环；i、j、k、l和m在每次出现时相同或不同，并表示0至4的整数，但当R1为氢时，i不为0。通过在N-苯基上引入取代基，可以增加器件的效率、稳定性和寿命，同时保持溶解性。这些化合物可用于各种有机器件，如有机发光二极管、光伏电池或有机半导体器件。
• Highly efficient deep-red organic electrophosphorescent devices with excellent operational stability using bis(indoloquinoxalinyl) derivatives as the host materials
  作者：Tsu-Hui Su、Chun-Hsiang Fan、Yu-Han Ou-Yang、Lun-Chia Hsu、Chien-Hong Cheng

  DOI：10.1039/c3tc30823e

  日期：——

  synthesized, characterized and used as the hosts for deep-red phosphorescent organic light-emitting diodes (PhOLEDs). The central linkers provide a way to reach higher molecular weights with little change of the energy gap of the molecules relative to the parent indoloquinoxaline molecule. These materials are bipolar and show high glass transition temperatures ∼200 °C and triplet energy gaps 2.25–2.37 eV. The

  三种新的双（吲哚并喹喔啉基）衍生物BIQF（6,6'-（4,4'-（9 H-芴-9,9-二基）双（4,1-亚苯基））bis（6 H-吲哚[2 ，3- b ] quinoxaline）），BIQTP（9,9'-（1,1'：4'，1''- terphenyl -4,4''- diyl ）bis（6 H -indolo [2,3- b ]喹喔啉）和BIQMCz（6,6'-（9-对甲苯基9 H-咔唑-3,6-二基）双（6 H-吲哚并[2,3- b ]喹喔啉）分别合成了由芴基，三联苯基和咔唑基连接的），表征并用作深红色磷光有机发光二极管（PhOLED）的主体。中心接头提供了一种在分子的能隙相对于母体几乎没有变化的情况下达到较高分子量的方法吲哚喹喔啉分子。这些材料是双极性的，显示出约200°C的高玻璃化转变温度和3.25-2.37 eV的三重态能隙。基于这些主体材料和铱深红色发射体的电致发光（EL）器件具有很高的器件效率，最大EQE
• Synthesis and characterization of deep blue emitters from starburst carbazole/fluorene compounds
  作者：Zujin Zhao、Xinjun Xu、Xiaopeng Chen、Xiaoming Wang、Ping Lu、Gui Yu、Yunqi Liu

  DOI：10.1016/j.tet.2007.12.059

  日期：2008.3

  A series of well-defined, highly fluorescent starburst compounds with a carbazole core and oligo(2,7-fluorene ethynylene) arms have been synthesized by Sonogashira coupling reaction and fully characterized. These conjugated compounds exhibit good solubility, high thermal stability, and excellent fluorescence quantum yields (up to 0.99). The incorporation of carbazole core interrupted the main-chain conjugation and resulted in blue-shifted absorption and emission. Moreover, deep blue light has been approached from organic light-emitting diodes (OLEDs) adopting these compounds as emitting layer. (c) 2008 Elsevier Ltd. All rights reserved.
• Blue light-emitting, electron-transporting materials based on ethynyl-linked D–A systems
  作者：Zujin Zhao、Peng Zhang、Fang Wang、Zixing Wang、Ping Lu、Wenjin Tian

  DOI：10.1016/j.cplett.2006.03.095

  日期：2006.6

  Two ethynyl-linked pi-conjugated compounds with bright blue photoluminescence property were designed, synthesized and fully characterized. The main structures of them contain a pyrene as electron acceptor, a carbazole as electron donor linked by an ethynyl unit. This D-A system has increased electron mobility and high quantum yields. One of the compounds was sandwiched as luminescent in single- and double-layer devices. By incorporating Alq as electron transport layer, the double-layer device exhibits dramatically improved performances compared with the single-layer device. The compounds are promising blue light-emitting and electron-transport materials. (c) 2006 Elsevier B.V. All rights reserved.