1-ethyl-2-(9-(2-ethylhexyl)-9H-carbazol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1-ethyl-2-(9-(2-ethylhexyl)-9H-carbazol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 3-Ethyl-2-[9-(2-ethylhexyl)carbazol-3-yl]imidazo[4,5-f][1,10]phenanthroline；3-ethyl-2-[9-(2-ethylhexyl)carbazol-3-yl]imidazo[4,5-f][1,10]phenanthroline
• 化学式: C₃₅H₃₅N₅
• 分子量: 525.696
• InChiKey: CBPXUSFKDHETBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 (npy)2Ir(μ-Cl)2Ir(npy)2 、 1-ethyl-2-(9-(2-ethylhexyl)-9H-carbazol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 乙二醇 、 水 为溶剂， 反应 16.0h， 以88.3%的产率得到[(npy)₂Ir(c-phen)]PF₆
  参考文献：
  名称：

  Two novel orange cationic iridium(III) complexes with multifunctional ancillary ligands used for polymer light-emitting diodes

  摘要：

  Two novel orange cationic iridium complexes [(npy)(2)Ir(o-phen)]PF6 and [(npy)(2)Ir(c-phen)] PF6 were synthesized. Hnpy: 2-(naphthalen-1-yl) pyridine; o-phen: a 1,10-phenanthroline derivative containing an electron-transporting functional group of 2,5-diphenyl-1,3,4-oxadiazole and a crystallization-resistant tert-butyl functional group; c-phen: a 1,10-phenanthroline derivative containing a hole-transporting functional group of carbazole and a crystallization-resistant 2-ethylhexyl functional group. Both of them are amorphous and possess high thermal stability with 5% weight-reduction temperatures (Delta T-5%) of 386 degrees C and 383 degrees C, and glass-transition temperatures (T-g) of 267 degrees C and 195 degrees C respectively. They were used as phosphorescent dopants in polymer light-emitting diodes (PLEDs) fabricated by solution-processed technology with configuration of ITO/PEDOT:PSS/PVK:PBD:iridium complex/TPBI/CsF/Al. At the optimal doping concentration of 2.0 wt%, the corresponding PLEDs exhibited the maximum current efficiencies of 9.1 cd A(-1) and 10.0 cd A(-1), the maximum external quantum efficiencies of 6.5% and 7.1%, and the maximum luminance of 2314 cd m(-2) and 3157 cd m(-2) respectively, with the same CIE coordinates of (0.57, 0.40). The results indicate that cationic iridium complexes are promising candidates for PLED applications when they are designed reasonably. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2012.09.035
• 作为产物：
  描述：

  9-(2-乙基己基)咔唑-3-甲醛 在 ammonium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-ethyl-2-(9-(2-ethylhexyl)-9H-carbazol-3-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Two novel orange cationic iridium(III) complexes with multifunctional ancillary ligands used for polymer light-emitting diodes

  摘要：

  Two novel orange cationic iridium complexes [(npy)(2)Ir(o-phen)]PF6 and [(npy)(2)Ir(c-phen)] PF6 were synthesized. Hnpy: 2-(naphthalen-1-yl) pyridine; o-phen: a 1,10-phenanthroline derivative containing an electron-transporting functional group of 2,5-diphenyl-1,3,4-oxadiazole and a crystallization-resistant tert-butyl functional group; c-phen: a 1,10-phenanthroline derivative containing a hole-transporting functional group of carbazole and a crystallization-resistant 2-ethylhexyl functional group. Both of them are amorphous and possess high thermal stability with 5% weight-reduction temperatures (Delta T-5%) of 386 degrees C and 383 degrees C, and glass-transition temperatures (T-g) of 267 degrees C and 195 degrees C respectively. They were used as phosphorescent dopants in polymer light-emitting diodes (PLEDs) fabricated by solution-processed technology with configuration of ITO/PEDOT:PSS/PVK:PBD:iridium complex/TPBI/CsF/Al. At the optimal doping concentration of 2.0 wt%, the corresponding PLEDs exhibited the maximum current efficiencies of 9.1 cd A(-1) and 10.0 cd A(-1), the maximum external quantum efficiencies of 6.5% and 7.1%, and the maximum luminance of 2314 cd m(-2) and 3157 cd m(-2) respectively, with the same CIE coordinates of (0.57, 0.40). The results indicate that cationic iridium complexes are promising candidates for PLED applications when they are designed reasonably. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2012.09.035

文献信息

• Two novel orange cationic iridium(III) complexes with multifunctional ancillary ligands used for polymer light-emitting diodes
  作者：Huaijun Tang、Yanhu Li、Baofeng Zhao、Wei Yang、Hongbin Wu、Yong Cao

  DOI：10.1016/j.orgel.2012.09.035

  日期：2012.12

  Two novel orange cationic iridium complexes [(npy)(2)Ir(o-phen)]PF6 and [(npy)(2)Ir(c-phen)] PF6 were synthesized. Hnpy: 2-(naphthalen-1-yl) pyridine; o-phen: a 1,10-phenanthroline derivative containing an electron-transporting functional group of 2,5-diphenyl-1,3,4-oxadiazole and a crystallization-resistant tert-butyl functional group; c-phen: a 1,10-phenanthroline derivative containing a hole-transporting functional group of carbazole and a crystallization-resistant 2-ethylhexyl functional group. Both of them are amorphous and possess high thermal stability with 5% weight-reduction temperatures (Delta T-5%) of 386 degrees C and 383 degrees C, and glass-transition temperatures (T-g) of 267 degrees C and 195 degrees C respectively. They were used as phosphorescent dopants in polymer light-emitting diodes (PLEDs) fabricated by solution-processed technology with configuration of ITO/PEDOT:PSS/PVK:PBD:iridium complex/TPBI/CsF/Al. At the optimal doping concentration of 2.0 wt%, the corresponding PLEDs exhibited the maximum current efficiencies of 9.1 cd A(-1) and 10.0 cd A(-1), the maximum external quantum efficiencies of 6.5% and 7.1%, and the maximum luminance of 2314 cd m(-2) and 3157 cd m(-2) respectively, with the same CIE coordinates of (0.57, 0.40). The results indicate that cationic iridium complexes are promising candidates for PLED applications when they are designed reasonably. (C) 2012 Elsevier B.V. All rights reserved.