4-(4-methylquinolin-2-yl)diphenylaniline | 863487-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(4-methylquinolin-2-yl)diphenylaniline
• 英文别名: N-(4-(4-methylquinolin-2-yl)phenyl)-N-phenylbenzenamine；4-(4-methylquinolin-2-yl)-N,N-diphenylaniline
• CAS: 863487-48-3
• 化学式: C₂₈H₂₂N₂
• 分子量: 386.496
• InChiKey: AFTHUPQWHZYBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 4-(4-methylquinolin-2-yl)diphenylaniline 以 乙二醇乙醚 、 水 为溶剂， 生成 [ClPt(4-(4-methylquinolin-2-yl)-N,N-diphenylaniline(-1H)]2
  参考文献：
  名称：

  亮氨酸基配体的环金属化铂（II）络合物作为高效电致发光剂

  摘要：

  一系列新的含lepidine-配体为基础的环金属化铂（II）配合物1 - 7与通式[PT（L）ACAC]（L =基于lepidine配体，ACAC =乙酰丙酮化物）已经被合成。配合物已使用光谱和电化学技术进行了表征。配合物2和5的单晶X射线结构已成功确定。讨论了取代基对配合物环金属化苯环的电子特征和氧化还原电势的影响。配合1 - 7在液体和固态中均具有高磷光性，覆盖从黄色到饱和红色的相当宽的光谱范围。这些配合物已成功用作掺杂材料，以制造电致发光器件，ITO / NPB（40 nm）/掺杂CBP的Pt配合物（5 wt％）（20 nm）/ BCP（10 nm）/ Alq 3（20 nm） / LiF（1 nm）/ Al（150 nm），表现出非常有前途的性能。掺杂有5 wt％3的器件产生的最大外部量子效率为15.2％，最大亮度为26847 cd m -2，对应的发光效率为29.83 cd A -1。

  DOI：

  10.1021/om100573r
• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到4-(4-methylquinolin-2-yl)diphenylaniline
  参考文献：
  名称：

  Synthesis and electroluminescent property of highly efficient phosphorescent red dopants based on modulated main ligands

  摘要：

  Novel red phosphorescent iridium(III) complexes, (DPAP-MQ)(2)Ir(tmd), (DMAP-MQ)(2)Ir(tmd), (PN-MQ)(2)Ir(tmd) were synthesized for red emitter of the phosphorescent organic light-emitting diodes (phOLEDs). The ligands have sites of both the electron donor and acceptor in a molecule. The main ligands consisted of electron-donors ((dimethylamino)phenyl, (diphenylamino)phenyl, (dimethylamino)naphthalene) and electron-acceptor methyl quinoline were synthesized by suzuki coupling reaction. The iridium(III) complexes based on main ligands and 2,2,6,6-tetramethyl-3,5-heptanedione(tmd) ancillary ligand were synthesized by Nonoyama reaction. Their luminescence property was investigated by UV-visible spectroscopy and photoluminescence (PL) spectroscopy. The manufactured PHOLEDs were characterized by investigation of current density-voltage-luminance, luminance efficiency, external quantum efficiency, electroluminescence spectrum. These phosphorescent iridium complexes will be promising candidates for highly efficient red emitters.

  DOI：

  10.1080/15421406.2017.1350041

文献信息

• Efficient Red-Emitting Cyclometalated Iridium(III) Complexes Containing Lepidine-Based Ligands
  作者：K. R. Justin Thomas、Marappan Velusamy、Jiann T. Lin、Chin-Hsiung Chien、Yu-Tai Tao、Yuh S. Wen、Ya-Hui Hu、Pi-Tai Chou

  DOI：10.1021/ic050385s

  日期：2005.8.1

  Heteroleptic cyclometalated iridium(III) complexes featuring lepidine-based ligands and acetyl acetone auxiliary ligand are synthesized. Multiple lowest energy absorption bands are observed for these complexes indicating substantial mixing of the singlet and triplet levels. All the complexes emit orange or red color in dichloromethane solutions with lifetimes in the range 1.6-3.7 mu s. The emission in the complexes probably originates from the (MLCT)-M-3 state. The complexes are applied as emitting guests in LED devices of the structure ITO/HTL(BPAPF or NPB)/6% Ir in CBP/BCP/Alq(3)LiF/Al. They exhibit excellent device characteristics with an orange to red EL profile.
• Synthesis and electroluminescent property of highly efficient phosphorescent red dopants based on modulated main ligands
  作者：Seo Yun Lee、Song Eun Lee、Ye Na Oh、Young Kwan Kim、Dong Myung Shin

  DOI：10.1080/15421406.2017.1350041

  日期：2017.8.13

  Novel red phosphorescent iridium(III) complexes, (DPAP-MQ)(2)Ir(tmd), (DMAP-MQ)(2)Ir(tmd), (PN-MQ)(2)Ir(tmd) were synthesized for red emitter of the phosphorescent organic light-emitting diodes (phOLEDs). The ligands have sites of both the electron donor and acceptor in a molecule. The main ligands consisted of electron-donors ((dimethylamino)phenyl, (diphenylamino)phenyl, (dimethylamino)naphthalene) and electron-acceptor methyl quinoline were synthesized by suzuki coupling reaction. The iridium(III) complexes based on main ligands and 2,2,6,6-tetramethyl-3,5-heptanedione(tmd) ancillary ligand were synthesized by Nonoyama reaction. Their luminescence property was investigated by UV-visible spectroscopy and photoluminescence (PL) spectroscopy. The manufactured PHOLEDs were characterized by investigation of current density-voltage-luminance, luminance efficiency, external quantum efficiency, electroluminescence spectrum. These phosphorescent iridium complexes will be promising candidates for highly efficient red emitters.
• Cyclometalated Platinum(II) Complexes of Lepidine-Based Ligands as Highly Efficient Electrophosphors
  作者：Marappan Velusamy、Chih-Hsin Chen、Yuh S. Wen、Jiann T. Lin、Chao-Chen Lin、Chin-Hung Lai、Pi-Tai Chou

  DOI：10.1021/om100573r

  日期：2010.9.13

  and redox potentials of the cyclometalated phenyl ring of the complexes are discussed. Complexes 1−7 are highly phosphorescent in fluid as well as in solid state, covering a rather broad spectral range from yellow to saturated red. These complexes were successfully used as a dopant material to fabricate the electroluminescent device, ITO/NPB (40 nm)/CBP-doped Pt complex (5 wt %) (20 nm)/BCP (10 nm)/Alq3

  一系列新的含lepidine-配体为基础的环金属化铂（II）配合物1 - 7与通式[PT（L）ACAC]（L =基于lepidine配体，ACAC =乙酰丙酮化物）已经被合成。配合物已使用光谱和电化学技术进行了表征。配合物2和5的单晶X射线结构已成功确定。讨论了取代基对配合物环金属化苯环的电子特征和氧化还原电势的影响。配合1 - 7在液体和固态中均具有高磷光性，覆盖从黄色到饱和红色的相当宽的光谱范围。这些配合物已成功用作掺杂材料，以制造电致发光器件，ITO / NPB（40 nm）/掺杂CBP的Pt配合物（5 wt％）（20 nm）/ BCP（10 nm）/ Alq 3（20 nm） / LiF（1 nm）/ Al（150 nm），表现出非常有前途的性能。掺杂有5 wt％3的器件产生的最大外部量子效率为15.2％，最大亮度为26847 cd m -2，对应的发光效率为29.83 cd A -1。