diethyl 6-[2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl]hexylphosphonate | 1268162-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: diethyl 6-[2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl]hexylphosphonate
• 英文别名: diethyl 6-(2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazol-9-yl)hexylphosphonate；9-[6-[Diethoxy(oxido)phosphaniumyl]hexyl]-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole；9-[6-[diethoxy(oxido)phosphaniumyl]hexyl]-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 1268162-41-9
• 化学式: C₃₄H₅₂B₂NO₇P
• 分子量: 639.385
• InChiKey: CLPYNJJWBKDLGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,7-二溴咔唑 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 51.0h， 生成 diethyl 6-[2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl]hexylphosphonate
  参考文献：
  名称：

  具有聚（2,7-咔唑）主链的共轭聚电解质和中性聚合物：合成，表征和光伏应用

  摘要：

  合成了具有氨，膦酸酯和磺酸酯亲水侧基的聚（2,7-咔唑）中性聚合物（PC-N，PC-NOH和PC-P）和聚电解质（PC-NBr和PC-SO 3 Na）用作体异质结光伏电池（BHJ PVC）阴极修饰的中间层。聚合物的吸收由聚（2,7-咔唑）主链确定，在溶液和薄膜中显示在约390 nm处的吸收峰。由于大的分子间相互作用，在聚合物膜的光致发光光谱中发现了波长大于500nm的受激准分子发射，这削弱了聚合物的发光。PC‐N，PC‐NBr，PC‐NOH和PC‐P具有可比的-5.23 eV的HOMO水平和-2.4 eV的LUMO水平，但是PC-SO 3的HOMO和LUMO水平Na分别上升至-4.91和-2.12 eV。选择PC‐N，PC‐NBr，PC‐NOH和PC‐P在BHJ PVC中构造薄的中间层，并以PFO‐DBT35：PCBM = 1：4作为活性层。与传统的铝阴极相比，具有中间层的双层阴极显示出P

  DOI：

  10.1002/pola.24547

文献信息

• 2,7-Carbazole-1,4-phenylene Copolymers with Polar Side Chains for Cathode Modifications in Polymer Light-Emitting Diodes
  作者：Xiaofeng Xu、Bing Han、Junwu Chen、Junbiao Peng、Hongbin Wu、Yong Cao

  DOI：10.1021/ma200191p

  日期：2011.6.14

  Alcohol-soluble 2,7-carbazole-1,4-phenylene copolymers PCP-NOH and PCP-EP, comprising surfactant-like diethanolamino and phosphonate end groups on the side chains, respectively, were synthesized and utilized as electron injection layer (EIL) in combination with high work function Al electrode in polymer light-emitting diodes (PLEDs). The UV-vis absorption and photoluminescence properties of the PCP-NOH and PCP-EP are mainly determined by the conjugated 2,7-carbazole-1,4-phenylene main chain. The PCP-NOH and PCP-EP possess comparable HOMO levels of -5.20 eV and LUMO levels arround -2.35 eV. Multilayer PLEDs with a device configuration of ITO/PEDOT:PSS (40 nm)/emissive layer (70 nm)/EIL (15 nm)/Al (100 am) were successfully fabricated. With fluorescent PFO-DBT15 as the emissive layer, the PLEDs using the PCP-NOH and PCP-EP as the EIL displayed luminous efficiency.(LE) of 1.01 and 0.88 cd/A, respectively, all obviously higher than 0.015 cd/A for sole Al cathode and 0.58 cd/A for the well-known Ba/Al cathode. With a phosphorescent Ir(mppy)(3)-doped polymer blend (PVK:PBD:Ir(mppy)(3) = 100:30:1) as the emissive layer, the PLEDs with the EIL showed high maximum LE of 39.3 cd/A for PCP-NOH and 42.5 cd/A for PCP-EP, in comparison to 0.35 cd/A for sole Al cathode and 32.2 cd/A for the Ba/Al cathode. Particularly, the PLED with PCP-EP as EIL exhibited an excellent LE of 33.3 cd/A at a current density of 61.1 mA/cm(2) (luminance = 20 300 cd/cm(2)), showing weak roll-off of efficiency at high current density. Inserting the polar alcohol-soluble polymers as interlayer can significantly increase built-in potentials in the PLEDs, from which electron injection barrier from the Al electrode is decreased. The results indicate that the PCP-NOH and PCP-EP are excellent electron injection polymers for high-performance PLEDs with high work function Al electrode.
• Conjugated polyelectrolytes and neutral polymers with poly(2,7‐carbazole) backbone: Synthesis, characterization, and photovoltaic application
  作者：Xiaofeng Xu、Wanzhu Cai、Junwu Chen、Yong Cao

  DOI：10.1002/pola.24547

  日期：2011.3

  Poly(2,7‐carbazole) neutral polymers (PC‐N, PC‐NOH, and PC‐P) and polyelectrolytes (PC‐NBr and PC‐SO3Na) with hydrophilic pendant groups of ammonium, phosphonate, and sulfonate were synthesized as interlayers for cathode modifications in bulk‐heterojunction photovoltaic cells (BHJ PVCs). The absorptions of the polymers were determined by the poly(2,7‐carbazole) backbone, showing absorption peaks at

  合成了具有氨，膦酸酯和磺酸酯亲水侧基的聚（2,7-咔唑）中性聚合物（PC-N，PC-NOH和PC-P）和聚电解质（PC-NBr和PC-SO 3 Na）用作体异质结光伏电池（BHJ PVC）阴极修饰的中间层。聚合物的吸收由聚（2,7-咔唑）主链确定，在溶液和薄膜中显示在约390 nm处的吸收峰。由于大的分子间相互作用，在聚合物膜的光致发光光谱中发现了波长大于500nm的受激准分子发射，这削弱了聚合物的发光。PC‐N，PC‐NBr，PC‐NOH和PC‐P具有可比的-5.23 eV的HOMO水平和-2.4 eV的LUMO水平，但是PC-SO 3的HOMO和LUMO水平Na分别上升至-4.91和-2.12 eV。选择PC‐N，PC‐NBr，PC‐NOH和PC‐P在BHJ PVC中构造薄的中间层，并以PFO‐DBT35：PCBM = 1：4作为活性层。与传统的铝阴极相比，具有中间层的双层阴极显示出P