2-溴-9,9-二乙基芴 | 287493-15-6

• 物质功能分类: 医药中间体 - OLED材料中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 2-溴-9,9-二乙基芴
• 英文名称: 2-bromo-9,9-diethyl-9H-fluorene
• 英文别名: 2-Bromo-9,9-diethylfluorene
• CAS: 287493-15-6
• 化学式: C₁₇H₁₇Br
• 分子量: 301.226
• InChiKey: HJXPGCTYMKCLTR-UHFFFAOYSA-N

物化性质

• 熔点：
  52.0 to 56.0 °C
• 沸点：
  163°C/2mmHg(lit.)
• 密度：
  1.265
• 溶解度：
  溶于甲苯

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  2-溴-9,9-二乙基芴 在 硝酸 、 溶剂黄146 作用下， 以92%的产率得到2-bromo-9,9-diethyl-7-nitrofluorene
  参考文献：
  名称：

  用于有机太阳能电池的具有更高尺寸的铂-乙炔聚合物

  摘要：

  合成了一系列新的包含不同尺寸的噻吩-三芳基胺发色团的铂（II）-乙炔聚合物P1，P2，P3，并评估了它们的电子能带结构，场效应电荷传输以及在体异质结太阳能电池中的应用。这些材料可溶于极性有机溶剂，并且在太阳光谱中显示出强吸收性（从薄膜获得的最高吸收系数为1.59×10 5  cm -1），因此使它们成为块状异质结聚合物太阳能电池的极佳候选者。旋涂聚合物薄膜表现出p沟道场效应电荷传输，空穴迁移率为1.90×10 -5对于P1，P2，P3，Ps为7.86×10 -5  cm 2  V -1  s -1，对于分子尺寸比P1高的P2，发现电荷载流子传输得到改善。还研究了它们的光伏性能和尺寸的依赖性。即使聚合物具有较高的带隙和较窄的吸收带宽，基于P3与[6,6] phenyl-C 61的共混物，仍可获得2.24％的最高功率转换效率AM1.5模拟太阳光照下的丁酸甲酯（PCBM）（1：5，w / w）。

  DOI：

  10.1002/asia.201100111
• 作为产物：
  描述：

  9,9-diethyl-9H-fluorene 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以63.4%的产率得到2-溴-9,9-二乙基芴
  参考文献：
  名称：

  Red non-doped electroluminescent dyes based on arylamino fumaronitrile derivatives

  摘要：

  A diarylamine, 2-(phenylamino)-9,9-diethylfluorene and three red fluorescent dyes based on arylamino fumaronitrile derivatives, bis(4-(N-(1-naphthyl)phenylamino)-phenyl)fumaronitrile (1-NPAFN, 5a), bis (4-(N-(2-naphthyl)phenylamino)phenyl)-fumaronitrile (2-NPAFN, 5b) and bis(4-(N-(9,9-diethyl-2-fluorenyl)phenylamino)-phenyl)fumaronitrile (EFPAFN, 5c), were prepared. The red dyes showed strong red photoluminescence upon excitation which centered at around 635, 650, 658 nm for 1-NPAFN, 2-NPAFN and EFPAFN in solid film respectively. Fluorescence concentration quenching of red dyes was suppressed. Thermal stability and energy levels were also measured. Multilayer non-doped electroluminescent devices were fabricated using the red dyes (5b, 5c) as red emitters. Device performance kept relatively constant at a wide current density level in the range of 20-150 mA/cm(2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.10.008

文献信息

• Color Pure and Stable Blue Light Emitting Material Containing Anthracene and Fluorene for OLED
  作者：Hyun-Tae Park、Dae-Hwan Oh、Jong-Won Park、Jin-Hak Kim、Sung-Chul Shin、Yun-Hi Kim、Soon-Ki Kwon

  DOI：10.5012/bkcs.2010.31.7.1951

  日期：2010.7.20

  A new blue light emitting anthracene derivative, 9,10-bis-(9',9'-diethyl-7'-t-butyl-fluoren-2'-yl)anthracene (BETF), has been designed and synthesized by a palladium catalyzed Suzuki cross-coupling. A theoretical calculation of the three-dimensional structure of BETF supports that it has a non coplanar structure and inhibited intermolecular interactions resulting in high luminescent efficiency and high color purity. BETF has good thermal stability with glass-transition temperature (Tg) of $131^\circ}C$. The PL maximum of BETF in solution and film were 438 nm and 440 nm, respectively, showing pure blue emission. A multilayer device using BETF as emitting material exhibits maximum luminescence efficiency of 2.2 cd/A and a pure blue emission (Commission Internationale de L'Eclairage (CIE) coordinates of x = 0.15, y = 0.10).

  一种新型蓝光发射的蒽衍生物——9,10-双(9',9'-二乙基-7'-叔丁基-芴-2'-基)蒽(BETF)，已通过钯催化的Suzuki交叉偶联反应设计合成。理论计算的BETF三维结构支持其具有非共面结构和抑制的分子间相互作用，从而实现高发光效率和高色纯度。BETF具有良好的热稳定性，玻璃化转变温度(Tg)为131°C。在溶液和薄膜中，BETF的PL最大值分别为438 nm和440 nm，显示出纯蓝色发射。使用BETF作为发光材料的多次层器件展现出最大发光效率为2.2 cd/A，发出纯蓝色光(国际照明委员会(CIE)坐标为x = 0.15，y = 0.10)。
• 芴并咪唑类衍生物及其制备方法
  申请人：上海大学

  公开号：CN105418515A

  公开（公告）日：2016-03-23

  本发明公开了一种一类芴并咪唑类衍生物及其制备方法。该化合物的结构通式为：。该方法便捷、普适、经济。式Ⅰ在有机光电材料和基于荧光探测的分析领域中有广泛应用前景；除此之外，由于此类化合物是含有两个氮原子的杂环化合物，具有良好的生物活性，也可作为药物中间体,制备人、畜的驱虫药物。
• 饱和红色发光的芴基苯喹啉铱配合物
  申请人：北京印刷学院

  公开号：CN111825722B

  公开（公告）日：2023-06-09

  本发明涉及一种饱和红色发光的芴基苯喹啉铱配合物，属于发光材料技术领域，其通式结构如下：其中，Y的结构为：本发明的饱和红色发光的芴基苯喹啉铱配合物既能保持2‑苯基喹啉铱配合物的高发光效率和饱和红光坐标(0.67,0.33)两个重要特征，也能够拓展分子的共轭程度，有效抑制分子间的强烈接触和内旋转，降低非辐射弛豫，改善热稳定和成膜性，增强化合物的空穴传输能力以及主体到客体的能量传递，有效提高材料和器件的红光效率。
• Multi-armed chromophores with very large two-photon absorption cross-sections
  申请人：The United States of America as represented by the Secretary of the Air Force

  公开号：US06300502B1

  公开（公告）日：2001-10-09

  Provided are chromophores with very large two-photon absorption cross-sections. One group of these chromophores has the formula: (T—Q)n—N—Phm wherein Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-3 and m has a value of 3−n, and wherein T is wherein R1 and R2 are alkyl groups having 1 to 20 carbon atoms, provided that when Q is a single bond, the value of n is 2 or 3. Another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as defined above, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-4 and m has a value of 4−n, and wherein G is a 4-arm core unit. Yet another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as described previously, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-6 and m has a value of 6−n, and wherein G is a 6-arm core unit.

  提供了具有非常大的双光子吸收截面的色素。其中一组这些色素具有以下结构式：(T—Q)n—N—Phm，其中Q是一个单键或1,4-苯基，Ph是一个苯基，n的值为1-3，m的值为3−n，而T是其中R1和R2是具有1到20个碳原子的烷基基团，条件是当Q是一个单键时，n的值为2或3。另一组这些色素具有以下结构式：(T—Q)n—G—Phm，其中T如上定义，Q是一个单键或1,4-苯基，Ph是一个苯基，n的值为1-4，m的值为4−n，而G是一个4臂核心单元。还有另一组这些色素具有以下结构式：(T—Q)n—G—Phm，其中T如前述所述，Q是一个单键或1,4-苯基，Ph是一个苯基，n的值为1-6，m的值为6−n，而G是一个6臂核心单元。
• Solution-processable organic fluorescent dyes for multicolor emission in organic light emitting diodes
  作者：Yong-Jin Pu、Makoto Higashidate、Ken-ichi Nakayama、Junji Kido

  DOI：10.1039/b806160b

  日期：——

  Four novel fluorescent dyes, bis(difluorenyl)amino-substituted carbazole 1, pyrene 2, perylene 3, and benzothiadiazole 4, were synthesized by C–N cross-coupling with a palladium catalyst. These dyes are soluble in common organic solvents, and their uniform films were formed by spin-coating from their solutions. Their glass transition temperatures were sufficiently high (120–181 °C) to form amorphous films for organic light emitting diodes. These solution processable dyes exhibited strong photoluminescence (PL) in the film form (1: sky blue, 2: blue-green, 3: yellow, and 4: deep red). Optical and electrochemical properties of the compounds were investigated with photoelectron spectroscopy and cyclic voltammetry. The energy levels obtained from both measurements were in good agreement, and those levels were related to the electronic properties of the central core; the electron-donating carbazole compound showed the lowest ionization potential and the electron-withdrawing benzothiadiazole compound showed the largest electron affinity. Simple double layer devices were prepared with these fluorescent dyes as emitting layer and bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (BAlq) as a common hole blocking layer for each color. Electroluminescence colors were the same as those of the PL spectra in each compound. These multicolor electroluminescences show that these conjugated oligomers can be candidates for solution processable light emitting materials for OLEDs as well as conjugated polymers or dendrimers.

  通过钯催化的C-N交叉耦合反应合成了四种新型荧光染料,即双(二芴基)氨基取代的咔唑1、芘2、苝3和苯并噻二唑4。这些染料能溶于常见的有机溶剂,并通过旋涂法制备了它们的均匀膜。它们的玻璃化转变温度足够高（120-181 °C）,足以形成用于有机发光二极管的非晶膜。这些可通过溶液法制备的染料在膜状态下呈现强烈的荧光发射（1:天蓝,2:蓝绿,3:黄色和4:深红）。通过光电子能谱和循环伏安法研究了所合成染料的光学和电化学性质。由这些测量得到的能级数据吻合良好,且发现这些能级与中心核的电子性质相关,其中给电子性的咔唑化合物表现出最低的电离势,而吸电子性的苯并噻二唑化合物表现出最大的电子亲和能。分别以这些荧光染料和双(2-甲基-8-喹啉酸)（对联苯酚酸）铝(III)（BAlq）为发射层和公共的空穴阻挡层制备了简单的双层器件。器件电致发光的颜色与每种染料的荧光光谱颜色相同。这些多色电致发光表明,这些共轭齐聚物不仅是共轭高分子或树枝状聚合物,也可以成为适用于有机电致发光材料的溶液可加工材料。