3,5-bis-(3-bromophenyl)-1,2,4-oxadiazole | 1003221-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis-(3-bromophenyl)-1,2,4-oxadiazole
• 英文别名: 3,5-bis(3-bromophenyl)-1,2,4-oxadiazole；3,5-Bis-(3-bromo-phenyl)-1,2,4-oxadiazole
• CAS: 1003221-19-9
• 化学式: C₁₄H₈Br₂N₂O
• 分子量: 380.038
• InChiKey: DTFOAQNUFZBCRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.92
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,5-bis-(3-bromophenyl)-1,2,4-oxadiazole 、 咔唑 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 48.0h， 以69.7%的产率得到3,5-bis(3-(9H-carbazol-9-yl)phenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of new bipolar host materials based on 1,2,4-oxadiazole for blue phosphorescent OLEDs

  摘要：

  Two novel bipolar host materials, namely 3,5-bis(4-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (pCzmOXD) and 3,5-bis(3-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (mCzmOXD) were designed and synthesized, by incorporating a new block 1,2,4-oxadiazole as the n-type moiety and changing its linking pattern with carbazole. As expected, high triplet energy (over 2.81 eV) for mCzmOXD was achieved due to the intrinsic meta-linkage of 1,2,4-oxadiazole. When both materials were applied in blue phosphorescent organic light-emitting diodes, good performance of 13.0 cd A(-1)/16.0 cd A(-1) were achieved for pCzmOXD and mCzmOXD in iridium(III) bis[(4, 6 - difluorophenyl)pyridinato - N, C-2'] picolinate (Flrpic)-based devices, respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.09.029
• 作为产物：
  描述：

  间溴苯甲腈 在 吡啶 、 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 62.0h， 生成 3,5-bis-(3-bromophenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  一种1,2,4-噁二唑小分子主体材料及其制备方 法、应用

  摘要：

  本发明公开了一种1,2,4-噁二唑小分子主体材料，该类材料含有亲电性的1个或多个1,2,4-噁二唑作为电子受体单元，在分子的末端接有电子给体单元。本发明还公开了上述小分子主体材料的制备方法，以间溴苯腈作为反应原料，制备得到双溴取代的中间体1,2,4-噁二唑化合物，然后通过铃木偶联反应将电子给体单元接到双溴取代的中间体1,2,4-噁二唑化合物上。本发明还公开了上述小分子主体材料的应用。本发明的小分子主体材料，具有较好的溶解性及成膜性，具有较强的亲电性，较低的LUMO能级，较高的电子迁移率。

  公开号：

  CN103951662B

文献信息

• 一种1,2,4-噁二唑小分子主体材料及其制备方 法、应用
  申请人：华南理工大学

  公开号：CN103951662B

  公开（公告）日：2016-05-04

  本发明公开了一种1,2,4-噁二唑小分子主体材料，该类材料含有亲电性的1个或多个1,2,4-噁二唑作为电子受体单元，在分子的末端接有电子给体单元。本发明还公开了上述小分子主体材料的制备方法，以间溴苯腈作为反应原料，制备得到双溴取代的中间体1,2,4-噁二唑化合物，然后通过铃木偶联反应将电子给体单元接到双溴取代的中间体1,2,4-噁二唑化合物上。本发明还公开了上述小分子主体材料的应用。本发明的小分子主体材料，具有较好的溶解性及成膜性，具有较强的亲电性，较低的LUMO能级，较高的电子迁移率。
• Asymmetric Design of Bipolar Host Materials with Novel 1,2,4-Oxadiazole Unit in Blue Phosphorescent Device
  作者：Qian Li、Lin-Song Cui、Cheng Zhong、Zuo-Quan Jiang、Liang-Sheng Liao

  DOI：10.1021/ol5002494

  日期：2014.3.21

  The intrinsic asymmetry of 1,2,4-oxadiazole was utilized to synthesize three isomers, DCzmOXD-1, DCzmOXD-2, and mCzmOXD, and high triplet energies over 2.80 eV made them good candidates for host materials in blue OLEDs. The best efficiencies of 23.0 cd A(-1)/20.5 lm W1-/11.2% in CE/PE/EQE were achieved by DCzmOXD-1 with derivation at the beta-carbon position of 1,2,4-oxadiazole.
• Synthesis of new bipolar host materials based on 1,2,4-oxadiazole for blue phosphorescent OLEDs
  作者：Qian Li、Lin-Song Cui、Cheng Zhong、Xiao-Dong Yuan、Shou-Cheng Dong、Zuo-Quan Jiang、Liang-Sheng Liao

  DOI：10.1016/j.dyepig.2013.09.029

  日期：2014.2

  Two novel bipolar host materials, namely 3,5-bis(4-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (pCzmOXD) and 3,5-bis(3-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (mCzmOXD) were designed and synthesized, by incorporating a new block 1,2,4-oxadiazole as the n-type moiety and changing its linking pattern with carbazole. As expected, high triplet energy (over 2.81 eV) for mCzmOXD was achieved due to the intrinsic meta-linkage of 1,2,4-oxadiazole. When both materials were applied in blue phosphorescent organic light-emitting diodes, good performance of 13.0 cd A(-1)/16.0 cd A(-1) were achieved for pCzmOXD and mCzmOXD in iridium(III) bis[(4, 6 - difluorophenyl)pyridinato - N, C-2'] picolinate (Flrpic)-based devices, respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.