2',8'-dibromo-2,2'',7,7''-tetrakis(1,1-dimethylethyl)-dispiro-[9H-fluorene-9,6'(12'H)-indeno[1,2-b]fluorene-12',9''-[9H]fluorene] | 915406-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2',8'-dibromo-2,2'',7,7''-tetrakis(1,1-dimethylethyl)-dispiro-[9H-fluorene-9,6'(12'H)-indeno[1,2-b]fluorene-12',9''-[9H]fluorene]
• 英文别名: 2,8-dibromo-2',2'',7',7''-tetra-tert-butyldispiro(fluorene-9',6-indeno[1,2-b]fluorene-12,9''-fluorene)
• CAS: 915406-69-8
• 化学式: C₆₀H₅₆Br₂
• 分子量: 936.913
• InChiKey: FZHXEFYZTDYRAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  62
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2',8'-dibromo-2,2'',7,7''-tetrakis(1,1-dimethylethyl)-dispiro-[9H-fluorene-9,6'(12'H)-indeno[1,2-b]fluorene-12',9''-[9H]fluorene] 、 4-甲酰基苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以30%的产率得到
  参考文献：
  名称：

  Synthesis and Properties of a Blue Bipolar Indenofluorene Emitter Based on a D-π-A Design

  摘要：

  Through a rational design, a novel Donor-Acceptor pi-conjugated (D-pi-A) blue fluorescent indenofluorene dye, DA-DSF-IF, has been synthesized for application In single-layer Small Molecule Organic Light Emitting Diodes (SMOLEDs). This new blue emitter possesses bipolar properties as well as good morphological and emission color stabilities and has been successfully used in a blue emitting single-layer SMOLED, with performances impressively magnified compared to a nonbipolar indenofluorene emitter.

  DOI：

  10.1021/ol201751p
• 作为产物：
  描述：

  2,2'',7.7''-tetra-tert-butyldispiro[fluorene-9,6'-indeno[1,2-b]fluorene-12',9''-fluorene] 在 溴 、 碘 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以90%的产率得到2',8'-dibromo-2,2'',7,7''-tetrakis(1,1-dimethylethyl)-dispiro-[9H-fluorene-9,6'(12'H)-indeno[1,2-b]fluorene-12',9''-[9H]fluorene]
  参考文献：
  名称：

  Synthesis and Properties of a Blue Bipolar Indenofluorene Emitter Based on a D-π-A Design

  摘要：

  Through a rational design, a novel Donor-Acceptor pi-conjugated (D-pi-A) blue fluorescent indenofluorene dye, DA-DSF-IF, has been synthesized for application In single-layer Small Molecule Organic Light Emitting Diodes (SMOLEDs). This new blue emitter possesses bipolar properties as well as good morphological and emission color stabilities and has been successfully used in a blue emitting single-layer SMOLED, with performances impressively magnified compared to a nonbipolar indenofluorene emitter.

  DOI：

  10.1021/ol201751p

文献信息

• tert-Butylated spirofluorene derivatives with arylamine groups for highly efficient blue organic light emitting diodes
  作者：Kum Hee Lee、Seul Ong Kim、Jae Nam You、Sunwoo Kang、Jin Yong Lee、Kyoung Soo Yook、Soon Ok Jeon、Jun Yeob Lee、Seung Soo Yoon

  DOI：10.1039/c2jm14869b

  日期：——

  A series of tert-butylated spirofluorene derivatives incorporating a diphenylaminoaryl-vinyl group was synthesized via the Horner–Wadsworth–Emmons olefination and a Suzuki cross-coupling reaction. To examine the electroluminescent properties of these materials, multilayered OLEDs were fabricated into the following device structure: ITO/DNTPD/NPB/MADN:blue dopant materials 1–14/Alq3/Liq/Al. All devices showed efficient blue emission. In particular, one device exhibited highly efficient sky blue emission with a maximum luminance of 25 100 cd m−2 at 8.5 V, as well as luminous, power and external quantum efficiencies of 9.5 cd A−1, 5.1 lm W−1 and 6.7% at 20 mA cm−2, respectively. The peak wavelength of electroluminescence was 458 and 484 nm with CIEx,y coordinates of (0.14, 0.21) at 8.0 V. In addition, a deep blue device with CIEx,y coordinates of (0.15, 0.15) at 8.0 V showed a luminous efficiency and external quantum efficiency of 3.8 cd A−1 and 3.3% at 20 mA cm−2, respectively.

  通过 Horner-Wadsworth-Emmons 烯化反应和铃木交叉偶联反应，合成了一系列含有二苯基氨基芳基乙烯基的叔丁基化螺芴衍生物。为了研究这些材料的电致发光特性，将多层有机发光二极管制成了以下器件结构：ITO/DNTPD/NPB/MADN：蓝色掺杂材料 1-14/Alq3/Liq/Al。所有器件都显示出高效的蓝色发射。其中，一个器件显示出高效的天蓝色发射，在 8.5 V 时的最大亮度为 25 100 cd m-2，在 20 mA cm-2 时的发光效率、功率效率和外部量子效率分别为 9.5 cd A-1、5.1 lm W-1 和 6.7%。电致发光的峰值波长为 458 和 484 nm，8.0 V 时的 CIEx,y 坐标为 (0.14, 0.21)。此外，深蓝色器件的 CIEx,y 坐标为 (0.15, 0.15)，8.0 V 时的发光效率和外部量子效率分别为 3.8 cd A-1 和 3.3%（20 mA cm-2）。
• Novel Materials for Organic Electroluminescent Devices
  申请人：Vestweber Horst

  公开号：US20080220285A1

  公开（公告）日：2008-09-11

  The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) as dopants in the emitting layer.

  本发明涉及利用式（1）化合物作为发光层杂质，改善有机电致发光装置，特别是蓝色发射装置。
• Intramolecular excimer emission as a blue light source in fluorescent organic light emitting diodes: a promising molecular design
  作者：Damien Thirion、Maxime Romain、Joëlle Rault-Berthelot、Cyril Poriel

  DOI：10.1039/c2jm16774c

  日期：——

  Intramolecular excimer emission arising from organic molecules as a blue light source in fluorescent Small Molecule Organic Light Emitting Diodes (SMOLEDs) is almost absent from the literature. In this work, three aryl-substituted DiSpiroFluorene–IndenoFluorenes (DSF–IFs 1–3) possessing different fluorescent properties due to their different main emitters have been investigated through a structure–property relationship study. Due to its particular geometry, the rigid DSF–IF platform 2 allows an ‘aryl/fluorene/aryl’ dimer to be preformed in the ground state leading, in the excited state, to a deep blue fluorescent emission through strong π–π intramolecular interactions between the two ‘aryl/fluorene/aryl’ arms. 2 has been successfully used as an emitting layer in a SMOLED with electroluminescence arising from electrogenerated intramolecular excimers and the properties of these excimer-based OLEDs have been compared to those of two model compounds (1 and 3). The simple and non-optimized double-layer device displays a deep blue colour (CIE coordinates: 0.19; 0.18) exhibiting a luminance of 510 Cd m−2 with a luminous efficiency of ca. 0.1 Cd A−1. This work is, to the best of our knowledge, the first rational and comparative study describing an intramolecular excimer based-SMOLED.

  有机分子产生的分子内激子发射是荧光小分子有机发光二极管（SMOLED）中的蓝光光源，但文献中几乎没有相关研究。在这项工作中，通过结构-性质关系研究，对三种具有不同主发射体的芳基取代二螺芴-茚芴（DSF-IFs 1-3）进行了研究，它们具有不同的荧光性质。由于其特殊的几何结构，刚性DSF-IF平台2允许“芳基/芴/芳基”二聚体在基态下形成，在激发态下，通过两个“芳基/芴/芳基”臂之间的强π-π分子内相互作用，产生深蓝色荧光发射。2已成功用作SMOLED中的发射层，其电致发光来自电致分子内激子，这些基于激子的OLED的特性与两种模型化合物（1和3）的特性
• Luminescence modulation in liquid crystalline phases containing a dispiro[fluorene-9,11′-indeno[1,2-b]fluorene-12′,9′′-fluorene] core
  作者：Sébastien Thiery、Benoît Heinrich、Bertrand Donnio、Cyril Poriel、Franck Camerel

  DOI：10.1039/c4tc00038b

  日期：——

  Luminescence modulations of a bulky dispiro[fluorene-9,11′-indeno[1,2-b]fluorene-12′,9′′-fluorene] (DSF-IF) core embedded in thermotropic liquid crystal phases.

  一个大的二螺旋[芴-9,11′-吲哚[1,2-b]芴-12′,9′′-芴]（DSF-IF）核心嵌入热致液晶相中的发光调制。
• VERBINDUNGEN FÜR ORGANISCHE ELEKTRONISCHE VORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP1883688B1

  公开（公告）日：2018-04-11