1-(4-fluorophenyl)-3-methyl benzimidazolium iodide | 869385-27-3

• 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-fluorophenyl)-3-methyl benzimidazolium iodide
• 英文别名: 1-(4-fluorophenyl)-3-methyl-benzimidazoline iodide
• CAS: 869385-27-3
• 化学式: C₁₄H₁₂FN₂*I
• 分子量: 354.166
• InChiKey: XPVZCJZJLWTZKG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-3-methyl benzimidazolium iodide 、 iridium(III) chloride trihydrate 在 sodium carbonate 、 silver carbonate 作用下， 以 乙二醇乙醚 为溶剂， 反应 20.0h， 以35%的产率得到Ir(nmb)3
  参考文献：
  名称：

  Deep Blue Phosphorescence of the Iridium(III) Complexes ContainingN-Heterocyclic Carbene Ligands

  摘要：

  Previously, the iridium complexes containing N-Heterocyclic carbene (NHC) ligands have caught attention because of their phosphorescence for organic light-emitting diodes (OLEDs). It was reported that the use of strong-field ligands such as carbenes should result in an increase of the blue phosphorescent efficiency of their metal complexes. In this study, the new NHC ligands, 1-(4-fluorophenyl)-3-methyl benzimidazolate (fpmb) and 1-naphthyl-3-methyl benzimidazolate (nmb), were introduced to the iridium complexes to develop phosphorescent dyes for OLED.We investigated photoabsorption and photoluminescence (PL) properties of the iridium complexes and studied their bandgaps with cyclic voltammetry (CV). Deep blue and green phosphorescence was observed with these complexes, and the bandgaps between their highest occupied molecular orbitals (HOMOs) and the lowest unoccupied molecular orbitals (LUMOs) were correlated with CV data. We also studied the electroluminescence (EL) properties of the new iridium complexes as possible phosphors for the application to OLED.

  DOI：

  10.1080/15421406.2012.703807
• 作为产物：
  描述：

  对氟碘苯 在 copper(l) iodide 、 caesium carbonate 作用下， 生成 1-(4-fluorophenyl)-3-methyl benzimidazolium iodide
  参考文献：
  名称：

  Deep Blue Phosphorescence of the Iridium(III) Complexes ContainingN-Heterocyclic Carbene Ligands

  摘要：

  Previously, the iridium complexes containing N-Heterocyclic carbene (NHC) ligands have caught attention because of their phosphorescence for organic light-emitting diodes (OLEDs). It was reported that the use of strong-field ligands such as carbenes should result in an increase of the blue phosphorescent efficiency of their metal complexes. In this study, the new NHC ligands, 1-(4-fluorophenyl)-3-methyl benzimidazolate (fpmb) and 1-naphthyl-3-methyl benzimidazolate (nmb), were introduced to the iridium complexes to develop phosphorescent dyes for OLED.We investigated photoabsorption and photoluminescence (PL) properties of the iridium complexes and studied their bandgaps with cyclic voltammetry (CV). Deep blue and green phosphorescence was observed with these complexes, and the bandgaps between their highest occupied molecular orbitals (HOMOs) and the lowest unoccupied molecular orbitals (LUMOs) were correlated with CV data. We also studied the electroluminescence (EL) properties of the new iridium complexes as possible phosphors for the application to OLED.

  DOI：

  10.1080/15421406.2012.703807

文献信息

• 一类以含氮杂环卡宾为第二主配体的铱配合 物及其制备方法
  申请人：南京大学

  公开号：CN104370974B

  公开（公告）日：2018-01-23

  本发明涉及一类具有新型配位方式的以含氮杂环卡宾为第二主配体的铱配合物，该系列铱配合物分子中含有两个相同或不同的吡啶衍生物或异喹啉衍生物作为第一主配体，以及含有氮杂环卡宾结构的第二主配体。相比于已经被广泛研究报道的铱配合物，该发明涵盖的这类新型铱配合物不仅具有发光效率高、化学性质稳定、易升华提纯等优点以外，且由于强电子给体卡宾配位结构的引入，能够有效调控配合物的发光颜色。通过修饰第一主配以及第二主配体的分子结构，能够在所有可见光波长范围内调节配合物的发光位置，这为有机电致发光显示器以及照明光源的设计生产提供了便利。同时，本发明介绍的一系列新型铱配合物的合成方法简单，产率较高，针对第一和第二主配体的化学修饰灵活。
• Carbene containing metal complexes as OLEDs
  申请人：Tsai Yui-Yi

  公开号：US20050258742A1

  公开（公告）日：2005-11-24

  A process for preparing a compound having the formula L 2 IrL′ is provided. The process comprises: combining and L′ in the presence of an organic solvent to form a mixture, wherein L is a suitable carbene ligand precursor coordinated to Ir; and L′ is a bidentate ligand or two monodentate ligands, and L is different from L′; Also provided is a process for preparing a compound having the formula The process comprises: (a) combining L, a carbene ligand precursor, with an organic solvent; (b) maintaining the mixture of step (a) at a temperature from about 175° C. to less than the boiling point of the organic solvent in (a). A process for preparing a compound with the formula L 3 Ir is also provided. This process comprises combining and L in the presence of alcohol and a base to form a mixture, wherein L is a bidentate ligand that may form a five-membered chelate ring.

  提供了一种制备具有公式L2IrL′的化合物的方法。该方法包括：在有机溶剂存在下结合L和L′以形成混合物，其中L是适当的卡宾配体前体与Ir配位；L′是双齿配体或两个单齿配体，且L与L′不同；还提供了一种制备具有公式的化合物的方法。该方法包括：(a)将L，卡宾配体前体与有机溶剂结合；(b)将步骤(a)的混合物保持在约175℃至有机溶剂沸点以下的温度下。还提供了一种制备具有公式L3Ir的化合物的方法。该方法包括在醇和碱的存在下结合L和L以形成混合物，其中L是可能形成五元螯合环的双齿配体。
• <i>N</i>-Heterocyclic Carbenes: Versatile Second Cyclometalated Ligands for Neutral Iridium(III) Heteroleptic Complexes
  作者：Tian-Yi Li、Xiao Liang、Liang Zhou、Chen Wu、Song Zhang、Xuan Liu、Guang-Zhao Lu、Li-Sha Xue、You-Xuan Zheng、Jing-Lin Zuo

  DOI：10.1021/ic501949h

  日期：2015.1.5

  With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)(2)Ir(NHC), were synthesized efficiently. The obtained Ir(III) complexes display typical phosphorescence of 455-485 nm with quantum yields up to 0.73. By modifying the phenyl moiety in the NHCs with electron-withdrawing substituents (e.g., -F or -CF3) or replacing it with N-heteroaromatic rings (pyridine or pyrimidine), the HOMO-LUMO gaps are broadened, and the emissions shift to the more blue region accordingly. Furthermore, to extend the application scope of NHCs as the second cyclometalated ligands, five other Ir(III) complexes from blue to red were synthesized with different first cyclometalated ligands. Finally, the organic light-emitting diodes using one blue emitter exhibit a maximum current efficiency of 37.83 cd A(-1), an external quantum efficiency of 10.3%, and a maximum luminance of 8709 cd m(-2). Our results demonstrate that NHCs as the second cyclometalated ligands are good candidates for the achievement of efficient phosphorescent Ir-III complexes and corresponding devices.
• An exploration of N -heterocyclic carbene-based Ir(III) complexes for phosphorescent organic light-emitting diode applications
  作者：Woosum Cho、Juho Yoon、Ganguri Sarada、Thota Giridhar、Yuan Liu、Zuo-Quan Jiang、Young Hoon Son、Byoung Yeop Kang、Jang Hyuk Kwon、Sung-Ho Jin

  DOI：10.1016/j.dyepig.2015.07.038

  日期：2015.12

  Two new blue emitting heteroleptic Ir(III) complexes containing a difluorophenylmethylpyridine (fpmpy)-based main ligand and a carbene-based ancillary ligand were synthesized: bis[2-(4,6-difluorophenyl)-4-methylpyridinato-C2,N](1'-(4'-fluorophenyl)-3'-methylbenzimidazole)iridium(III) and bis[2-(4,6-difluorophenyl)-4-methylpyridinato-C2,N](1'-methyl-3'-phenylbenzimidazole)iridium(III). The synthesis, X-ray crystal structures, photophysical and electrochemical properties, and PhOLED performance of both Ir(III) complexes are described. The two Ir(III) complexes showed very similar UV visible absorption spectra irrespective of the presence of the fluorine atom in the ancillary ligand. The photoluminescence spectrum of the complex with the additional fluorine atom showed double emission bands at 464 and 482 nm in dichloromethane solution, whereas the alternate complex, without the extra fluorine atom, only exhibited a single emission at 487 nm. Both Will) complexes were utilized for blue PhOLEDs with an identical device configuration. The complex with the additional fluorine atom exhibited an external quantum efficiency of 4.2%, which was higher than that of the alternate complex (3.5%). (C) 2015 Elsevier Ltd. All rights reserved.