2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2"-yl)phenoxy)decanoxy)-1,4-dimethyl benzene | 335276-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2"-yl)phenoxy)decanoxy)-1,4-dimethyl benzene
• 英文别名: 2-[4-[10-(2,5-Dimethylphenoxy)decoxy]phenyl]-5-phenyl-1,3,4-oxadiazole；2-[4-[10-(2,5-dimethylphenoxy)decoxy]phenyl]-5-phenyl-1,3,4-oxadiazole
• CAS: 335276-13-6
• 化学式: C₃₂H₃₈N₂O₃
• 分子量: 498.665
• InChiKey: ZSLQZGIIKGSHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2"-yl)phenoxy)decanoxy)-1,4-dimethyl benzene 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以35%的产率得到2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2-yl)phenoxy)decanoxy)-1,4-bis(bromomethyl)benzene
  参考文献：
  名称：

  Soluble Electroluminescent Poly(phenylene vinylene)s with Balanced Electron- and Hole Injections

  摘要：

  We report a new route for the design of efficient soluble electroluminescent PPV-based copolymers bearing electron-deficient oxadiazole (OXD) moieties on side chains. The introduction of OXD through a long alkylene spacer with PPV backbone provides a molecular dispersion of OXD in the film; both the side chain OXD and the main chain PPV do retain their own electron-transport and emissive properties, respectively. The use of phenylene vinylene derivatives with asymmetric and branched substituents and a long spacer provides solubility for ease of device fabrication as well as amorphous structure to allow a well-mixing of OXD groups with the main chains. By properly adjusting the OXD content through copolymerization, we can tailor the chemical structure of electroluminescent material to give a balance of hole- and electron injections for various metal cathodes, such that the quantum efficiency is significantly improved and the turn-on voltage is reduced for the devices with aluminum and calcium. For the device with calcium fabricated in open air, a maximum brightness of 15000 cd/m(2) at 15 V/100 nm and a maximum luminance efficiency of 2.27 cd/A can be obtained, respectively, about 30 times brighter and 9.4 times more efficient than those with the corresponding homopolymer, poly[2-methoxy-5-(2'-ethylhexyloxy)-p-phenylenevinylene] (MEH-PPV). The use of physical blends to simulate the copolymers provides no significant improvement, since phase-separation structures appear, causing an inefficient utilization of OXD and sometimes voltage-dependent emission spectra. The present route permits a fabrication of single layer PLED with high brightness, high efficiency, and low turn-on voltage.

  DOI：

  10.1021/ja003135d
• 作为产物：
  描述：

  1,10-二溴癸烷 在 sodium methylate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2"-yl)phenoxy)decanoxy)-1,4-dimethyl benzene
  参考文献：
  名称：

  Soluble Electroluminescent Poly(phenylene vinylene)s with Balanced Electron- and Hole Injections

  摘要：

  We report a new route for the design of efficient soluble electroluminescent PPV-based copolymers bearing electron-deficient oxadiazole (OXD) moieties on side chains. The introduction of OXD through a long alkylene spacer with PPV backbone provides a molecular dispersion of OXD in the film; both the side chain OXD and the main chain PPV do retain their own electron-transport and emissive properties, respectively. The use of phenylene vinylene derivatives with asymmetric and branched substituents and a long spacer provides solubility for ease of device fabrication as well as amorphous structure to allow a well-mixing of OXD groups with the main chains. By properly adjusting the OXD content through copolymerization, we can tailor the chemical structure of electroluminescent material to give a balance of hole- and electron injections for various metal cathodes, such that the quantum efficiency is significantly improved and the turn-on voltage is reduced for the devices with aluminum and calcium. For the device with calcium fabricated in open air, a maximum brightness of 15000 cd/m(2) at 15 V/100 nm and a maximum luminance efficiency of 2.27 cd/A can be obtained, respectively, about 30 times brighter and 9.4 times more efficient than those with the corresponding homopolymer, poly[2-methoxy-5-(2'-ethylhexyloxy)-p-phenylenevinylene] (MEH-PPV). The use of physical blends to simulate the copolymers provides no significant improvement, since phase-separation structures appear, causing an inefficient utilization of OXD and sometimes voltage-dependent emission spectra. The present route permits a fabrication of single layer PLED with high brightness, high efficiency, and low turn-on voltage.

  DOI：

  10.1021/ja003135d

文献信息

• Soluble Electroluminescent Poly(phenylene vinylene)s with Balanced Electron- and Hole Injections
  作者：Yuh-Zheng Lee、Xiwen Chen、Show-An Chen、Pei-Kuen Wei、Wun-Shain Fann

  DOI：10.1021/ja003135d

  日期：2001.3.1

  We report a new route for the design of efficient soluble electroluminescent PPV-based copolymers bearing electron-deficient oxadiazole (OXD) moieties on side chains. The introduction of OXD through a long alkylene spacer with PPV backbone provides a molecular dispersion of OXD in the film; both the side chain OXD and the main chain PPV do retain their own electron-transport and emissive properties, respectively. The use of phenylene vinylene derivatives with asymmetric and branched substituents and a long spacer provides solubility for ease of device fabrication as well as amorphous structure to allow a well-mixing of OXD groups with the main chains. By properly adjusting the OXD content through copolymerization, we can tailor the chemical structure of electroluminescent material to give a balance of hole- and electron injections for various metal cathodes, such that the quantum efficiency is significantly improved and the turn-on voltage is reduced for the devices with aluminum and calcium. For the device with calcium fabricated in open air, a maximum brightness of 15000 cd/m(2) at 15 V/100 nm and a maximum luminance efficiency of 2.27 cd/A can be obtained, respectively, about 30 times brighter and 9.4 times more efficient than those with the corresponding homopolymer, poly[2-methoxy-5-(2'-ethylhexyloxy)-p-phenylenevinylene] (MEH-PPV). The use of physical blends to simulate the copolymers provides no significant improvement, since phase-separation structures appear, causing an inefficient utilization of OXD and sometimes voltage-dependent emission spectra. The present route permits a fabrication of single layer PLED with high brightness, high efficiency, and low turn-on voltage.