2,8-bis(2-pyridyl)thianthrene | 1373485-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,8-bis(2-pyridyl)thianthrene
• 英文别名: 2-(8-Pyridin-2-ylthianthren-2-yl)pyridine
• CAS: 1373485-12-1
• 化学式: C₂₂H₁₄N₂S₂
• 分子量: 370.499
• InChiKey: PCWXJPOHDTXFIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,8-dibromothianthrene 、 三正丁基2-吡啶基锌 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到2,8-bis(2-pyridyl)thianthrene
  参考文献：
  名称：

  噻蒽基低聚物作为空穴传输材料

  摘要：

  噻蒽-亚芳基共轭单元已通过 Suzuki 或 Stille 偶联反应设计和合成。合成化合物的结构和性质通过HNMR、CNMR、MS、UV-Vis吸收光谱、荧光光谱以及电化学测量表征。发光研究表明噻蒽是良好的发色团。所得薄膜的电性能也证实了这些新型芳基 π 共轭聚合物在开发各种电和电化学固态器件方面的应用潜力。

  DOI：

  10.3998/ark.5550190.0013.315

文献信息

• HETEROCYCLIC COMPOUNDS AND THEIR USE IN ELECTRO-OPTICAL OR OPTO-ELECTRONIC DEVICES
  申请人：Power OLEDs Limited

  公开号：US20160035983A1

  公开（公告）日：2016-02-04

  Compounds exhibiting high hole mobility and/or high glass transition temperatures are provided which are of the formula [Ar 1 ] m [Ar 2 ] n wherein: m is an integer from 1-3 and n is an integer and may be 1 or 2; Ar 1 represents a thianthrene residue having a linkage to Ar 2 at one or two positions selected from ring positions 1-4 and 5-8 and optionally mono-, bi- or poly-substituted with C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, fluoro, phenyl or biphenyl which in the case of phenyl or biphenyl may be further substituted with C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or fluoro; Ar 2 represents a residue derived from an arylamine in which the aryl rings are phenyl, naphthyl or anthracenyl optionally substituted with C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or fluoro, a polycyclic fused or chain aromatic ring system optionally containing nitrogen or sulphur and in a chain aromatic ring system optionally containing one or more chain oxygen or sulphur atoms, a triarylphosphine oxide or an arylsilane the rings of any of which are optionally substituted with C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or fluoro. Certain of the compounds may be used in electron transport layers and may be doped with p-type dopants. They may be incorporated into OLEDs, organic photovoltaic devices, imaging members and thin film transistors. In further embodiments there are provided OLEDs or other devices e.g. electrostatic latent image forming members in which improved efficiency is obtained by using as electron transport layers, electron injectors, hosts and emitters (dopants) ambipolar or electron-transmitting compounds in which thianthrene is bonded to aryl e.g. 1-anthracenyl-9-yl-thianthrene, 1-biphenyl-4-yl-thianthrene and 9,10-Bis(1-thianthrenyl) anthracene.

  提供了具有高空穴迁移率和/或高玻璃化转变温度的化合物，其化学式为[Ar1]m[Ar2]n，其中：m为1-3的整数，n为整数，可以为1或2；Ar1代表具有与Ar2连接的噻吩残基，所述连接选择自环位置1-4和5-8的一个或两个位置，并可选择单取代、双取代或多取代于C1-C4烷基、C1-C4烷氧基、氟、苯基或联苯基，其中在苯基或联苯基的情况下，可以进一步取代于C1-C4烷基、C1-C4烷氧基或氟；Ar2代表从芳基胺衍生的残基，其中芳环为苯基、萘基或蒽基，可选择单取代、双取代或多取代于C1-C4烷基、C1-C4烷氧基或氟，多环融合或链芳基环系统可选择包含氮或硫，在链芳基环系统中可选择包含一个或多个链氧或硫原子，三芳基氧化磷或芳基硅烷，其任何环都可选择单取代、双取代或多取代于C1-C4烷基、C1-C4烷氧基或氟。其中某些化合物可用于电子传输层，并可掺杂p型掺杂剂。它们可被纳入OLED、有机光伏器件、成像元件和薄膜晶体管。在进一步的实施例中，提供了使用作为电子传输层、电子注入剂、宿主和发射体（掺杂剂）的双极或电子传输化合物，其中噻吩与芳基（例如1-蒽基-9-基噻吩、1-联苯基-4-基噻吩和9,10-双（1-噻吩基）蒽）结合，从而获得改进的效率的OLED或其他器件，例如静电潜影成像成员。
• Heterocyclic compounds and their use in electro-optical or opto-electronic devices
  申请人：Power OLEDs Limited

  公开号：US10439147B2

  公开（公告）日：2019-10-08

  Compounds exhibiting high hole mobility and/or high glass transition temperatures are provided which are of the formula [Ar1]m[Ar2]n wherein: m is an integer from 1-3 and n is an integer and may be 1 or 2; Ar1 represents a thianthrene residue having a linkage to Ar2 at one or two positions selected from ring positions 1-4 and 5-8 and optionally mono-, bi- or poly-substituted with C1-C4-alkyl-, C1-C4-alkoxy-, fluoro, phenyl or biphenyl which in the case of phenyl or biphenyl may be further substituted with C1-C4-alkyl-, C1-C4-alkoxy- or fluoro; Ar2 represents a residue derived from an arylamine in which the aryl rings are phenyl, naphthyl or anthracenyl optionally substituted with C1-C4-alkyl-, C1-C4-alkoxy- or fluoro, a polycyclic fused or chain aromatic ring system optionally containing nitrogen or sulphur and in a chain aromatic ring system optionally containing one or more chain oxygen or sulphur atoms, a triarylphosphine oxide or an arylsilane the rings of any of which are optionally substituted with C1-C4-alkyl-, C1-C4-alkoxy- or fluoro. Certain of the compounds may be used in electron transport layers and may be doped with p-type dopants. They may be incorporated into OLEDs, organic photovoltaic devices, imaging members and thin film transistors. In further embodiments there are provided OLEDs or other devices e.g. electrostatic latent image forming members in which improved efficiency is obtained by using as electron transport layers, electron injectors, hosts and emitters (dopants) ambipolar or electron-transmitting compounds in which thianthrene is bonded to aryl e.g. 1-anthracenyl-9-yl-thianthrene, 1-biphenyl-4-yl-thianthrene and 9,10-Bis(1-thianthrenyl) anthracene.

  提供了具有高空穴迁移率和/或高玻璃化转变温度的化合物，其化学式为[Ar1]m[Ar2]n，其中： m 是 1-3 之间的整数，n 是整数，可以是 1 或 2； Ar1 代表噻蒽残基，在选自环位置 1-4 和 5-8 的一个或两个位置与 Ar2 连接，并可选地被 C1-C4-烷基、C1-C4-烷氧基、氟、苯基或联苯单取代、双取代或多取代，其中苯基或联苯可进一步被 C1-C4-烷基、C1-C4-烷氧基或氟取代； Ar2 代表衍生自芳基胺的残留物，其中芳基环为可选被 C1-C4-烷基、C1-C4-烷氧基或氟取代的苯基、萘基或蒽基，可选含有氮或硫的多环融合或链状芳香环系统，以及在链状芳香环系统中可选含有一个或多个链状氧原子或硫原子的三芳基氧化膦或芳基硅烷，其中任一芳基环可选被 C1-C4-烷基、C1-C4-烷氧基或氟取代。 某些化合物可用于电子传输层，并可掺杂 p 型掺杂剂。这些化合物可用于有机发光二极管、有机光伏器件、成像元件和薄膜晶体管。 在更进一步的实施方案中，提供了有机发光二极管或其他装置，例如静电潜像形成部件，其中通过使用噻蒽与芳基（例如 1-蒽基-9-基-噻蒽、1-联苯-4-基-噻蒽和 9,10-双（1-噻蒽）蒽）键合的双极性或电子传递化合物作为电子传输层、电子注入器、宿主和发射器（掺杂剂），可提高效率。
• [EN] HETEROCYCLIC COMPOUNDS AND THEIR USE IN ELECTRO-OPTICAL OR OPTO-ELECTRONIC DEVICES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION DANS DES DISPOSITIFS ÉLECTRO-OPTIQUES OU OPTO-ÉLECTRONIQUES
  申请人：POWER OLEDS LTD

  公开号：WO2014167286A2

  公开（公告）日：2014-10-16

  Compounds exhibiting high hole mobility and/or high glass transition temperatures are provided which are of the formula [Ar1]m[Ar2]n wherein: m is an integer from 1-3 and n is an integer and may be 1 or 2; Ar1 represents a dibenzo[b,e][1,4]dioxine, phenoxanthine, thianthrene, dibenzo[b,e]1,4-thiaselenane or selenanthrene residue having a linkage to Ar2 at one or two positions selected from ring positions 1-4 and 5-8 and optionally mono-, bi-or poly-substituted with C1-C4-alkyl-, C1-C4-alkoxy-, fluoro, phenyl or biphenyl which in the case of phenyl or biphenyl may be further substituted with C1-C4-alkyl-, C1-C4-alkoxy-or fluoro; Ar2represents a residue derived from an arylamine in which the aryl rings are phenyl, naphthyl or anthracenyl optionally substituted with C1-C4-alkyl-, C1-C4-alkoxy- or fluoro, a polycyclic fused or chain aromatic ring system optionally containing nitrogen or sulphur and in a chain aromatic ring system optionally containing one or more chain oxygen or sulphur atoms, a triarylphosphine oxide or an arylsilane the rings of any of which are optionally substituted with C1-C4-alkyl-, C1-C4-alkoxy-or fluoro. The compounds may be used in electron transport layers and may be doped with p-type dopants. They may be incorporated into OLEDs, organic photovoltaic devices, imaging members and thin film transistors. In further embodiments there are provided OLEDs or other devices e.g. electrostatic latent image forming members in which improved efficiency is obtained by using as electron transport layers, electron injectors, hosts and emitters (dopants) ambipolar or electron-transmitting compounds in which thianthrene is bonded to aryl e.g.1-anthracenyl-9-yl-thianthrene, 1-biphenyl-4-yl-thianthrene and 9,10-Bis(1-thianthrenyl) anthracene.