1-(4-(3,6-di-t-butylcarbazol-9-yl))phenyl-2-phenylbenzoimidazole | 891258-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4-(3,6-di-t-butylcarbazol-9-yl))phenyl-2-phenylbenzoimidazole
• 英文别名: 1-(4-(3,6-di-t-butylcarbazol-9-yl))phenyl-2-phenylbenzimidazole；3,6-Ditert-butyl-9-[4-(2-phenylbenzimidazol-1-yl)phenyl]carbazole；3,6-ditert-butyl-9-[4-(2-phenylbenzimidazol-1-yl)phenyl]carbazole
• CAS: 891258-77-8
• 化学式: C₃₉H₃₇N₃
• 分子量: 547.743
• InChiKey: HTIZMCFTBZPTPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 2,2,6,6-四甲基-3,5-庚二酮 、 1-(4-(3,6-di-t-butylcarbazol-9-yl))phenyl-2-phenylbenzoimidazole 在 sodium carbonate 作用下， 以 乙二醇乙醚 、 水 为溶剂， 以27%的产率得到(t-BuCzPBI)Pt(dpm)
  参考文献：
  名称：

  Design, Synthesis, and Optoelectronic Properties of Dendrimeric Pt(II) Complexes and Their Ability to Inhibit Intermolecular Interaction

  摘要：

  Dendrimeric Pt(II) complexes [((CN)-N-boolean AND)Pt(dpm)] and [Pt((CN)-N-boolean AND)(2)] (Hdpm = dipivaloylmethane, (HCN)-N-boolean AND = 1,2-diphenylbenzoimidazole and its derivatives containing the carbazole. dendrons) have been synthesized and characterized systematically. All of the complexes display green emission in the range of 495-535 nm that originated from the 360-440 nm absorption bands, which are assigned to d pi(Pt)->pi*(L) metal-to-ligand charge transfer (MLCT) mixed with intraligand pi(L)->pi*(L) transition. Solution photoluminescence quantum yield (phi(p) 0.26-0.31) of the heteroleptic complexes [((CN)-N-boolean AND)Pt(dpm)] obviously increases when compared with that of complex [((CN)-N-boolean AND)Pt(acac)]. Organic light-emitting diode devices based on these Pt(II) complexes with a multilayer configuration were fabricated and gave desirable electroluminescent (EL) performances, such as non- or less red-shifted EL spectra, in comparison with the photoluminescence spectra and slow efficiency roll-off with increasing brightness or current density. Complex [(t-BuCzCzPBI)Pt(dpm)] (where t-BuCzCzPBI = 1-(4-(3,6-di-(3,6-di-t-butylcarbazol-9-yl))carbazol-9-yl)phenyl-2-phenylbenzoimidazole) showed the best performance, with a maximum current efficiency of 29.31 cd/A and a maximum external quantum efficiency (EQE) of 9.04% among the fabricated devices. Likewise, for homoleptic [Pt(t-BuCzCzPBI)(2)] dendrimer, the powder phi(p) (0.14) and maximum EQE (0.74%) improve by 7 and 7.4 times, respectively, as high as they do for nondendrimeric [Pt(1,2-diphenylbenzoimidazole)(2)] (0.02, 0.10%), although its efficiency is still lower than that of the heteroleptic counterpart due to the severely distorted square-planar geometry of the emitting core. These results reveal that large steric hindrance from ancillary ligand (dpm) or the homoleptic conformation can effectively inhibit intermolecular interaction for these denchimeric Pt(II) complexes.

  DOI：

  10.1021/ic402099x

文献信息

• Synthesis, characterization and electrophosphorescent properties of mononuclear platinum(II) complexes based on 2-phenylbenzoimidazole derivatives
  作者：Hui Li、Junqiao Ding、Zhiyuan Xie、Yanxiang Cheng、Lixiang Wang

  DOI：10.1016/j.jorganchem.2009.04.024

  日期：2009.8

  The rational design, synthesis and characterization of five phosphorescent platinum complexes [(C boolean AND N) Pt(acac)] [Hacac = acetylacetone, HC boolean AND N = 1-methyl-2-(4-fluorophenyl)benzoimidazole (H-FMBI), 1-methyl-2-phenylbenzoimidazole (H-MBI), 1,2-diphenyl-benzoimidazole (H-PBI), 1-(4-(3,6-di-t-butylcarbazol-9-yl)) phenyl-2-phenylbenzoimidazole (t-BuCz-H-PBI), and 1-(4-(3,6-di-(3,6-di-t-butyl-carbazol-9-yl))carbazol-9-yl) phenyl-2-phenylbenzoimidazole (t-BuCzCz-H-PBI)] have been discussed. The crystal structure of (MBI) Pt(acac) shows a nearly ideal square planar geometry around Pt atom and the weak intermolecular interactions with pi-pi spacing of 3.55 angstrom. All of the complexes emit green phosphorescence from the metal-to-ligand charge-transfer (MLCT) excited state with high quantum efficiency (0.08-0.17) at room temperature. A multilayer organic light-emitting diode (OLED) with (MBI) Pt(acac) as phosphorescent dopant was fabricated using the method of high-vacuum thermal evaporation, which gives a maximum brightness, luminous and power efficiency of 13 605 cd/m(2), 15.1 cd/A and 4.3 lm/W, respectively. In contrast, the comparable performance can be achieved in the solution-processed OLED based on (t-BuCzPBI) Pt(acac) with a peak brightness, luminous and power efficiency of 13 606 cd/m(2), 17.5 cd/A and 8.4 lm/W, respectively. The better device efficiency results from the good square plane of central Pt coordination unit and the inhibition of the aggregates due to bulky and rigid t-butylcarbazole dendrons. (C) 2009 Elsevier B.V. All rights reserved.
• Design, Synthesis, and Optoelectronic Properties of Dendrimeric Pt(II) Complexes and Their Ability to Inhibit Intermolecular Interaction
  作者：Hui Li、Jing Li、Junqiao Ding、Wei Yuan、Zilong Zhang、Luyi Zou、Xingdong Wang、Hongmei Zhan、Zhiyuan Xie、Yanxiang Cheng、Lixiang Wang

  DOI：10.1021/ic402099x

  日期：2014.1.21

  Dendrimeric Pt(II) complexes [((CN)-N-boolean AND)Pt(dpm)] and [Pt((CN)-N-boolean AND)(2)] (Hdpm = dipivaloylmethane, (HCN)-N-boolean AND = 1,2-diphenylbenzoimidazole and its derivatives containing the carbazole. dendrons) have been synthesized and characterized systematically. All of the complexes display green emission in the range of 495-535 nm that originated from the 360-440 nm absorption bands, which are assigned to d pi(Pt)->pi*(L) metal-to-ligand charge transfer (MLCT) mixed with intraligand pi(L)->pi*(L) transition. Solution photoluminescence quantum yield (phi(p) 0.26-0.31) of the heteroleptic complexes [((CN)-N-boolean AND)Pt(dpm)] obviously increases when compared with that of complex [((CN)-N-boolean AND)Pt(acac)]. Organic light-emitting diode devices based on these Pt(II) complexes with a multilayer configuration were fabricated and gave desirable electroluminescent (EL) performances, such as non- or less red-shifted EL spectra, in comparison with the photoluminescence spectra and slow efficiency roll-off with increasing brightness or current density. Complex [(t-BuCzCzPBI)Pt(dpm)] (where t-BuCzCzPBI = 1-(4-(3,6-di-(3,6-di-t-butylcarbazol-9-yl))carbazol-9-yl)phenyl-2-phenylbenzoimidazole) showed the best performance, with a maximum current efficiency of 29.31 cd/A and a maximum external quantum efficiency (EQE) of 9.04% among the fabricated devices. Likewise, for homoleptic [Pt(t-BuCzCzPBI)(2)] dendrimer, the powder phi(p) (0.14) and maximum EQE (0.74%) improve by 7 and 7.4 times, respectively, as high as they do for nondendrimeric [Pt(1,2-diphenylbenzoimidazole)(2)] (0.02, 0.10%), although its efficiency is still lower than that of the heteroleptic counterpart due to the severely distorted square-planar geometry of the emitting core. These results reveal that large steric hindrance from ancillary ligand (dpm) or the homoleptic conformation can effectively inhibit intermolecular interaction for these denchimeric Pt(II) complexes.