9-[4-(isoquinolin-1-yl)phenyl]-9H-carbazole | 1395928-53-6

• 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: 9-[4-(isoquinolin-1-yl)phenyl]-9H-carbazole
• 英文别名: 9-(4-Isoquinolin-1-ylphenyl)carbazole
• CAS: 1395928-53-6
• 化学式: C₂₇H₁₈N₂
• 分子量: 370.453
• InChiKey: SQPHALNVNZFXNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  iridium(III) acetylacetonate 、 9-[4-(isoquinolin-1-yl)phenyl]-9H-carbazole 在 anthracene 作用下， 以 neat (no solvent) 为溶剂， 以80%的产率得到fac-[Ir(9-[4-isoquinolin-1-yl-phenyl]-9H-carbazole(-H))3]
  参考文献：
  名称：

  Synthesis, structure, photophysical and electrochemical properties of series of new fac-triscyclometallated iridium complexes with carbazole or oxadiazole moieties

  摘要：

  A series of new fac-triscyclometallated iridium complexes Ir(Ln)(3) (n = 1-6) (L-1: 2-{4-[5-phenyl-[1,3,4] oxadiazol-2-yl]-phenyl}-pyridine, L2: 2-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}pyridine, L3: 9-(4-pyridin-2-yl-phenyl)-9H-carbazole, L4: 1-[4-(5-phenyl-[1,3,4] oxadiazol-2-yl)-phenyl]- isoquinoline, L5: 1-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}-isoquinoline, L6: 9-(4-isoquinolin-1-yl-phenyl)-9H-carbazole) based on Ir(ppy)(3) (ppy = phenyl-pyridine) and Ir(piq)(3) (piq = 1-phenylisoquinoline) were synthesized from Ir(acac)(3) and corresponding ligands by a new and effective way using anthracene as a solvent. Single-crystal X-ray diffraction spectra of three complexes were studied and the iridium centers were found to adopt distorted octahedral coordination geometry. UV-Vis, photoluminescence, cyclic voltammetry were employed for studying the photophysical and electrochemical properties. These complexes exhibit intense phosphorescence in toluene solution at room temperature with high quantum efficiencies (0.07-0.58) and submicrosecond lifetimes (0.57-0.87 mu s). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.010
• 作为产物：
  描述：

  9-(4-溴苯基)咔唑 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 28.75h， 生成 9-[4-(isoquinolin-1-yl)phenyl]-9H-carbazole
  参考文献：
  名称：

  Synthesis, structure, photophysical and electrochemical properties of series of new fac-triscyclometallated iridium complexes with carbazole or oxadiazole moieties

  摘要：

  A series of new fac-triscyclometallated iridium complexes Ir(Ln)(3) (n = 1-6) (L-1: 2-{4-[5-phenyl-[1,3,4] oxadiazol-2-yl]-phenyl}-pyridine, L2: 2-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}pyridine, L3: 9-(4-pyridin-2-yl-phenyl)-9H-carbazole, L4: 1-[4-(5-phenyl-[1,3,4] oxadiazol-2-yl)-phenyl]- isoquinoline, L5: 1-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}-isoquinoline, L6: 9-(4-isoquinolin-1-yl-phenyl)-9H-carbazole) based on Ir(ppy)(3) (ppy = phenyl-pyridine) and Ir(piq)(3) (piq = 1-phenylisoquinoline) were synthesized from Ir(acac)(3) and corresponding ligands by a new and effective way using anthracene as a solvent. Single-crystal X-ray diffraction spectra of three complexes were studied and the iridium centers were found to adopt distorted octahedral coordination geometry. UV-Vis, photoluminescence, cyclic voltammetry were employed for studying the photophysical and electrochemical properties. These complexes exhibit intense phosphorescence in toluene solution at room temperature with high quantum efficiencies (0.07-0.58) and submicrosecond lifetimes (0.57-0.87 mu s). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.010

文献信息

• Bipolar Host Materials with Carbazole and Isoquinoline/Benzothiazole Moieties for Green Phosphorescent Organic Light-Emitting Diodes
  作者：Jwajin Kim、Se Hyun Kim、Ho Won Lee、Song Eun Lee、Young Kwan Kim、Seung Soo Yoon

  DOI：10.1166/jnn.2016.13241

  日期：2016.10.1

  In this study, we demonstrate three bipolar host materials based on carbazole and isoquinoline/benzothiazole derivatives for use in green phosphorescent organic light-emitting diodes. Particularly, 9-[4-(isoquinolin-1-yl)phenyl]-9H-carbazole (1) exhibited good properties for use in green phosphorescent organic light-emitting diodes. A device using compound 1 as the host with the green phosphorescent dopant bis[2-(1,1′,2′,1″-terphen-3-yl)pyridinato- C,N]iridium(III)(acetylacetonate) showed the green emission with a maximum external quantum efficiency, power efficiency, and luminance efficiency of 8.1%, 26.71 lm/W, and 29.76 cd/A at 20 mA/cm2, respectively. The Commission International de L’Eclairage (CIE) chromaticity coordinates of this device were (0.35, 0.61) at 8.0 V.

  在这项研究中，我们展示了三种基于咔唑和异喹啉/苯噻唑衍生物的双极性主材料，可用于绿色磷光有机发光二极管。特别是，9-[4-(异喹啉-1-基)苯基]-9H-咔唑（1）表现出良好的特性，适用于绿色磷光有机发光二极管。使用化合物1作为主材料，并与绿色磷光掺杂剂双[2-(1,1′,2′,1″-三苯基-3-基)吡啶基-C,N]铱(III)(乙酰丙酮)的设备显示出绿色发光，最大外量子效率为8.1%，功率效率为26.71 lm/W，亮度效率为29.76 cd/A，电流密度为20 mA/cm²。在8.0 V下，此设备的国际照明委员会（CIE）色度坐标为(0.35, 0.61)。
• Red-emitting IrIII(C^N)2(P-donor ligand)Cl-type complexes showing aggregation-induced phosphorescent emission (AIPE) behavior for both red and white OLEDs
  作者：Huiying Li、Dongming Jia、Chaofan Yao、Yulin Jing、Bochen Li、Xiaolong Yang、Yuanhui Sun、Bochao Su、Guijiang Zhou、Bo Jiao

  DOI：10.1016/j.dyepig.2022.110538

  日期：2022.9

  can show decent EL efficiencies in the solution-processed red-emitting organic Light-emitting diodes (OLEDs) with a maximum external quantum efficiency (ηext) of 8.5%, a maximum current efficiency (ηL) of 22.0 cd A−1 and a maximum power efficiency (ηP) of 15.9 lm W−1. Furthermore, as long-wavelength emitter, solution-processed white OLEDs (WOLEDs) have been constructed based on the red-emitting AIPE IrIII(C^N)2(P-donor

  分别用三苯基膦和三乙基膦的不同P-供体配体成功制备了两种带有C^N配体和咔唑官能团的红色发光Ir III (C^N) 2 (P-供体配体)Cl型配合物。研究它们在 THF 和水的混合物中的磷光行为以揭示它们的聚集诱导磷光发射 (AIPE) 能力，这也表明它们在掺杂薄膜中的磷光量子产率 ( Φ P ) 远高于在稀溶液中的磷光量子产率 (Φ P )。它们的AIPE主要是由C^N配体中芳香链段的受阻拉伸运动引起的，并抑制了它们的配位骨架的变形。AIPE 配合物可以具有 AIE 因子 ( αAIE )约。7.4. 此外，咔唑基团可有效提高相关AIPE发光体的空穴传输能力，有利于其电致发光能力。因此，Ir III (C^N) 2 (P 供体配体)Cl 型配合物可以在溶液处理的红色发光有机发光二极管 (OLED) 中显示出良好的 EL 效率，具有最大的外量子效率 ( η ext ) 为 8.5%，最大电流效率