1-((9,9-diethyl-9H-fluoren-2-yl)ethynyl)pyrene | 1369762-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-((9,9-diethyl-9H-fluoren-2-yl)ethynyl)pyrene
• 英文别名: 1-[2-(9,9-Diethylfluoren-2-yl)ethynyl]pyrene
• CAS: 1369762-91-3
• 化学式: C₃₅H₂₆
• 分子量: 446.591
• InChiKey: AAWQCCDAAFULFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-溴芘 、 9,9-diethyl-2-ethynyl-9H-fluorene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 生成 1-((9,9-diethyl-9H-fluoren-2-yl)ethynyl)pyrene
  参考文献：
  名称：

  The use of a polarity matching and high-energy exciton generating host in fabricating efficient purplish-blue OLEDs from a sky-blue emitter

  摘要：

  我们在这篇论文中揭示了一项新发现，即利用极性匹配和高能激子产生宿主的有机发光二极管（OLED），使用天蓝色发射器产生紫蓝色发射。作为天蓝色发射体，1-((9,9-二乙基-9H-芴-2-基)乙炔基)芘的CIExy坐标为(0.190, 0.241)，外部量子效率为3.5%，在100 cd m-2条件下的功率效率为1.2 lm W-1。由此产生的紫蓝色发射使色彩饱和度超过 100%。之所以能产生异常明显的蓝移，可能是因为掺杂浓度较低，可防止发射体分离导致的浴色偏移；极性匹配的宿主可进一步分散发射体；高效的宿主和客体能级配对可在宿主上产生激子，从而触发短波长发射。此外，宿主还能产生更高能量的激子，以促进触发更短波长的发射。高效率的原因可能是低掺杂浓度防止了浓度淬灭引起的效率衰减，宿主上产生的激子促进了有效的宿主-宿主能量转移，以及所采用的宿主具有有效的宿主-宿主能量转移效应。值得注意的是，这种新方法也适用于其他淡蓝色发光体，只要它们的分子结构没有立体阻碍，就能产生非常理想的深蓝色光。

  DOI：

  10.1039/c2jm32216a

文献信息

• The use of a polarity matching and high-energy exciton generating host in fabricating efficient purplish-blue OLEDs from a sky-blue emitter
  作者：Jwo-Huei Jou、Yu-Lin Chen、Jing-Ru Tseng、Ri-Zong Wu、Jing-Jong Shyue、K. R. Justin Thomas、Neha Kapoor、Chien-Tien Chen、Yi-Ping Lin、Po-Hung Wang、Hsiao-Wen Hung、Jung-Yu Li、Shih-Pu Chen

  DOI：10.1039/c2jm32216a

  日期：——

  We reveal in this communication a new finding regarding the use of a sky-blue emitter to generate purplish-blue emission from organic light emitting diodes (OLEDs) with a polarity matching and high-energy exciton generating host. The resulting device exhibits CIExy coordinates of (0.155, 0.063) and a 3.5% external quantum efficiency, with a 1.2 lm W−1 power efficiency at 100 cd m−2 as a sky-blue emitter, 1-((9,9-diethyl-9H-fluoren-2-yl)ethynyl)pyrene with CIExy of (0.190, 0.241) is doped into a host of 4,4′-bis(9-carbazolyl)-biphenyl, for example. The resulting purplish-blue emission enables a greater than 100% color saturation. The extraordinarily marked blue-shift may result from a low doping concentration to prevent bathochromic shift due to emitter segregation, a polarity matching host to further disperse the emitter, and an efficient host and guest energy level pairing that enables excitons to be generated on the host to trigger short wavelength emission. Furthermore, the host is capable of generating excitons with higher energy to facilitate the triggering of emission with a shorter wavelength. The high efficiency may be attributed to the low doping concentration preventing efficiency roll-off caused by concentration-quenching, the excitons generated on the host facilitating the occurrence of the effective host-to-guest energy transfer, and the employed host possessing an effective host-to-guest energy transfer effect. Notably, the new approach also works for other light-blue emitters in yielding a highly desirable deep-blue light, provided their molecular structure is free of steric hindrance.

  我们在这篇论文中揭示了一项新发现，即利用极性匹配和高能激子产生宿主的有机发光二极管（OLED），使用天蓝色发射器产生紫蓝色发射。作为天蓝色发射体，1-((9,9-二乙基-9H-芴-2-基)乙炔基)芘的CIExy坐标为(0.190, 0.241)，外部量子效率为3.5%，在100 cd m-2条件下的功率效率为1.2 lm W-1。由此产生的紫蓝色发射使色彩饱和度超过 100%。之所以能产生异常明显的蓝移，可能是因为掺杂浓度较低，可防止发射体分离导致的浴色偏移；极性匹配的宿主可进一步分散发射体；高效的宿主和客体能级配对可在宿主上产生激子，从而触发短波长发射。此外，宿主还能产生更高能量的激子，以促进触发更短波长的发射。高效率的原因可能是低掺杂浓度防止了浓度淬灭引起的效率衰减，宿主上产生的激子促进了有效的宿主-宿主能量转移，以及所采用的宿主具有有效的宿主-宿主能量转移效应。值得注意的是，这种新方法也适用于其他淡蓝色发光体，只要它们的分子结构没有立体阻碍，就能产生非常理想的深蓝色光。
• Pyrene-Fluorene Hybrids Containing Acetylene Linkage as Color-Tunable Emitting Materials for Organic Light-Emitting Diodes
  作者：K. R. Justin Thomas、Neha Kapoor、M. N. K. Prasad Bolisetty、Jwo-Huei Jou、Yu-Lin Chen、Yung-Cheng Jou

  DOI：10.1021/jo300285v

  日期：2012.4.20

  New blue- to yellow-emitting materials have been developed by incorporating fluorene-based chromophores on pyrene core with acetylene linkage and using multifold palladium-catalyzed cross-coupling reactions. Both mono- and tetrasubstituted derivatives have been synthesized and characterized. The tetrasubstituted derivatives displayed red-shifted emission when compared to the monosubstituted derivative indicative of an extended conjugation in the former. End-capping with a diphenylamine unit further red-shifted the absorption and emission profiles and imparted a weak dipolar character to the molecules. Amine-containing derivatives displayed positive solvatochromism in the fluorescence spectra indicating a more polar excited state due to an efficient charge migration from the diphenylamine donor to the pyrene pi-acceptor. All of the derivatives were tested as emitting dopants with host material 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) in a multilayered OLED and found to exhibit bright blue or yellow electroluminescence. The device utilizing 1,3,6,8-tetrasubstituted pyrene derivative as a dopant emitter displayed highest maximum luminescence 4630 cd/m(2) with power efficiency 3.8 lm/W and current efficiency 7.1 cd/A at 100 cd/m(2) attributable to the proper alignment of energy levels that led to the efficient harvesting of excitons. All of the devices exhibited color purity over a wide range of operating voltages.