1-(10'-bromodecanoxy)-2,5-dimethylbenzene | 130402-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(10'-bromodecanoxy)-2,5-dimethylbenzene
• 英文别名: 2-(10-Bromodecoxy)-1,4-dimethylbenzene
• CAS: 130402-65-2
• 化学式: C₁₈H₂₉BrO
• 分子量: 341.332
• InChiKey: LRFKEJMIQWNGFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(10'-bromodecanoxy)-2,5-dimethylbenzene 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 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：

  2,5-二甲基苯酚 、 1,10-二溴癸烷 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以63%的产率得到1-(10'-bromodecanoxy)-2,5-dimethylbenzene
  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

• Electroluminiscent conjugated polymers modified with high eletronegative heterocyclic moieties and their applications in polymeric light emitting diodes
  申请人：National Science Council Taiwan corporation

  公开号：US20030109656A1

  公开（公告）日：2003-06-12

  This invention provides a method for syntheses of new electroluminescent conjugated polymers modified with high electronegative heterocyclic groups (such as 1,3,4-oxadiazole-diyl, 1,3,4-thiadiazole-diyl, and 1,2,4-triazole-diyl). These electroluminescent polymers (homopolymers, statistical copolymers or block coplymers) are obtained by polymerization of bis(halomethyl) arenes modified with heterocyclic groups via the Wessling precursor route, Gilch side chain route, Wittig reaction or Wittig-Hornor reaction. By a proper selection of the monomers and their ratios in the polymerization, the emissive polymers (fully conjugated or limited conjugating length) covering the full visible range even extending to the near-IR range can be prepared. The polymeric light emitting diodes (PLED) with these materials as emissive layer or electron transport layer have high external quantum efficiency and can be used as indicators and displays for cellular phones, pagers, portable computer, wristwatch, toys, etc.

  本发明提供了一种合成新型电致发光的共轭聚合物的方法，其经过修饰的含有高电负性杂环基团（如1,3,4-噁二唑-二基基团、1,3,4-噻二唑-二基基团和1,2,4-三唑-二基基团）。这些电致发光聚合物（同聚物、随机共聚物或嵌段共聚物）是通过通过Wessling前驱体路线、Gilch侧链路线、Wittig反应或Wittig-Hornor反应修饰的双(卤甲基)芳烃聚合而成。通过适当选择单体和它们在聚合中的比例，可以制备出发射聚合物（完全共轭或有限共轭长度），其覆盖整个可见光范围，甚至延伸到近红外范围。使用这些材料作为发射层或电子传输层的聚合物发光二极管（PLED）具有高外部量子效率，可以用作手机、寻呼机、便携式计算机、手表、玩具等的指示器和显示器。
• US6495644B1
  申请人：——

  公开号：US6495644B1

  公开（公告）日：2002-12-17
• US6693158B2
  申请人：——

  公开号：US6693158B2

  公开（公告）日：2004-02-17
• 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.