3-bromo-7-(N,N-diphenylamino)-5,5-spirofluorenyl-5H-dibenzo[a,d]cycloheptene | 1375329-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-bromo-7-(N,N-diphenylamino)-5,5-spirofluorenyl-5H-dibenzo[a,d]cycloheptene
• 英文别名: 3-bormo-7-(N,N-diphenylamino)-5,5-spirofluorenyl-5H-dibenzo-[a,d]cycloheptene；14'-bromo-N,N-diphenylspiro[fluorene-9,2'-tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene]-5'-amine
• CAS: 1375329-10-4
• 化学式: C₃₉H₂₆BrN
• 分子量: 588.546
• InChiKey: URKSWCKKVPOTLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-7-(N,N-diphenylamino)-5,5-spirofluorenyl-5H-dibenzo[a,d]cycloheptene 在 哌啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 36.0h， 生成 3-(N,N-diphenylamino)-7-((thiophenyl-2-yl)acrylic acid)-5,5-spirofluorenyl-5H-dibenzo-[a,d]cycloheptene
  参考文献：
  名称：

  Spirally configured cis-stilbene/fluorene hybrids as bipolar, organic sensitizers for solar cell applications

  摘要：

  基于二苯并苏伯烯核心的杂合材料，在C-5位具有螺旋荧光苯连接，C-3和C-7位分别带有氨基供体和β-噻吩基-α-氰基丙烯酸受体基团，作为新型有机敏化剂材料用于太阳能电池应用。基于这些材料的太阳能电池设备在AM 1.5 G条件下显示出高达6.1%的转换效率（η）（开路电压Voc = 697 mV，短路电流密度Jsc = 12.2 mA cm−2，填充因子FF = 0.72）。最佳的光电流转换效率（IPCE）值在450–550 nm吸收范围内超过75%。

  DOI：

  10.1039/c2cc17079e
• 作为产物：
  描述：

  3,7-dibromodibenzosuberone 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 3-bromo-7-(N,N-diphenylamino)-5,5-spirofluorenyl-5H-dibenzo[a,d]cycloheptene
  参考文献：
  名称：

  SPIRALLY CONFIGURED CIS-STILBENE/FLUORENE HYBRID MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

  摘要：

  式（1）展示了一个螺旋配置的顺式-双苯/芴杂化材料，其中n为1、2或3，R1至R6独立地选自氢原子、卤原子、氰基、烷基、环烷基、烷氧基、氨基、卤代烷基、硫代烷基、硅基、烯基和芳香环基的组合，R8为氢原子、叔丁基或芳基，当n为1时，R7为氢原子、二芳基胺基或2-二芳基胺基螺环芴基团，当n为2或3时，R7为氢原子、二芳基胺基或2-二芳基胺基螺环芴基团。

  公开号：

  US20180298279A1

文献信息

• Enabling a bright orange–red emission with a high EQE with a seven-member-ring based fluorescent emitter with a matching host
  作者：Jwo-Huei Jou、Yao-Ching Hsieh、Hui-Huan Yu、Chih-Chia An、Chieh-Ju Li、Chien-Tien Chen、Wei-Shan Chao、Hao-Wei Liu、Jing-Jong Shyue

  DOI：10.1016/j.orgel.2015.07.055

  日期：2015.11

  A bright orange-red organic light-emitting diode (OLED) with an extraordinarily high external quantum efficiency (EQE) was achieved by using a seven-member-ring based fluorescent emitter with a matching host. The emitter, 3-(N,N-diphenylamino)-7-(beta, beta-dicyanoethenyl)-5,5-spirofluorenyl-5H-dibenzo[ a,d]cycloheptene, was composed of a spirally configured cis-stilbene/fluorene moiety with an ambipolar character, and the matching host was 1-butyl-9,10-naphthalene-anthracene (BANE). An orange-red emission peaking at 617 nm with an EQE continuously rolling up to its observable maximum luminance was obtained as a 1.5 wt% of the red emitter was doped into the BANE host. For examples, the EQEs were increased from 5.01 +/- 0.015% to 5.76 +/- 0.02%, and 6.43 +/- 0.04% as the luminance was increased from 10,000 to 15,000 and 20,000 cd/m(2), respectively. The high efficiency at high brightness as well as an unusual efficacy roll-up may be attributed to both the efficiency-effective device architectural factors, including low injection barriers, balanced carrier injection, effective host-to-guest energy transfer, and effective exciton generation on both host and guest, and the ambipolar emitter that showed an increasing balance in carrier injection as the applied voltage continued to increase. (C) 2015 Elsevier B.V. All rights reserved.