10,10'-bis-(4-tert-butyl-phenyl)-10H,10'H-(3,3')biphenothiazinyl | 883983-89-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10,10'-bis-(4-tert-butyl-phenyl)-10H,10'H-(3,3')biphenothiazinyl
• 英文别名: 10-(4-Tert-butylphenyl)-3-[10-(4-tert-butylphenyl)phenothiazin-3-yl]phenothiazine
• CAS: 883983-89-9
• 化学式: C₄₄H₄₀N₂S₂
• 分子量: 660.947
• InChiKey: OXPVXWPACRNCSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  778.9±60.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10,10'-bis-(4-tert-butyl-phenyl)-10H,10'H-(3,3')biphenothiazinyl 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 生成 7,7'-dibromo-10,10'-bis-(4-tert-butylphenyl)-10H,10'H-[3,3']biphenothiazinyl
  参考文献：
  名称：

  High Efficiency New Hole Injection Materials for Organic Light Emitting Diodes Based on Dimeric Phenothiazine and Phenoxazine Moiety Derivatives

  摘要：

  基于苯噻嗪和苯氧咽的新型孔注入材料被合成，并通过紫外-可见光谱（UV-vis）、光致发光（PL）光谱和循环伏安法（CV）研究了合成材料的电光特性。1-BPNA-t-BPBP和1-BPNA-t-BPBPOX的玻璃化转变温度（Tg）分别为127 °C和200 °C，高于商业孔注入层（HIL）材料2-TNATA的110 °C。合成材料1-BPNA-t-BPBP和1-BPNA-t-BPBPOX的最高占据分子轨道（HOMO）能级分别为4.97 eV和4.91 eV，表明与ITO的HOMO（4.8 eV）和孔传输层（HTL）材料NPB的HOMO（5.4 eV）有良好的匹配。作为HIL在OLED器件中使用合成材料后，1-BPNA-t-BPBPOX的功率效率为2.43 lm/W，高于2-TNATA的1.98 lm/W和1-BPNA-t-BPBP的1.39 lm/W。这些结果表明，1-BPNA-t-BPBPOX表现出更高的功率效率，约比商业HIL材料2-TNATA提高了18%。

  DOI：

  10.1166/jnn.2012.5886
• 作为产物：
  描述：

  吩噻嗪 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三叔丁基膦 、 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 生成 10,10'-bis-(4-tert-butyl-phenyl)-10H,10'H-(3,3')biphenothiazinyl
  参考文献：
  名称：

  Highly Efficient New Hole Injection Materials for Organic Light Emitting Diodes Base on Phenothiazine Derivatives

  摘要：

  基于苯噻嗪的新孔注入材料被合成，合成材料的电光性能通过紫外-可见光光谱、光致发光光谱以及循环伏安法进行了测试。1-NDD-t-BPBP和2-NDD-t-BPBP的玻璃化转变温度分别为180°C和177°C，均高于商业HIL材料2-TNATA的110°C。关于合成材料的HOMO能级，1-NDD-t-BPBP和2-NDD-t-BPBP分别为4.99和5.02 eV，表明它们的HOMO值与ITO的4.8 eV和HTL材料NPB的5.4 eV之间匹配良好。此外，从合成材料在450 nm以上的波长范围内几乎没有吸收的事实来看，合成材料可以有效作为HIL材料。合成材料被用作OLED器件中的HIL，产生的光致效率分别为4.51 cd/A（1-NDD-t-BPBP）和4.44 cd/A（2-NDD-t-BPBP）。这些结果表明，1-NDD-t-BPBP表现出更优越的光致效率，比商业HIL材料2-TNATA提高约11%。

  DOI：

  10.1166/jnn.2014.8456

文献信息

• High Efficiency New Hole Injection Materials for Organic Light Emitting Diodes Based on Dimeric Phenothiazine and Phenoxazine Moiety Derivatives
  作者：Youngil Park、Beomjin Kim、Changjun Lee、Jaehyun Lee、Ji-Hoon Lee、Jongwook Park

  DOI：10.1166/jnn.2012.5886

  日期：2012.5.1

  New hole injection materials for organic light emitting diodes (OLEDs) based on phenothiazine and phenoxazine were synthesized, and the electro-optical properties of synthesized materials were examined by through UV-visible (UV-vis), photoluminescence (PL) spectrum and cyclic voltammetry (CV). 1-BPNA-t-BPBP and 1-BPNA-t-BPBPOX showed Tg of 127 and 200 °C, which are higher than that (110 °C) of 2-TNATA, a commercial hole injection layer (HIL) material. The highest occupied molecular orbital (HOMO) level of the synthesized materials of 1-BPNA-t-BPBP and 1-BPNA-t- BPBPOX were 4.97 and 4.91 eV, indicating values well-matched between HOMO (4.8 eV) of ITO and HOMO (5.4 eV) of NPB, hole transporting layer (HTL) material. As a result of using the synthesized materials in OLED device as HIL, 1-BPNA-t-BPBPOX of 2.43 lm/W was higher than 2-TNATA of 1.98 lm/W and 1-BPNA-t-BPBP of 1.39 lm/W in power efficiency. These results indicated that 1-BPNA-t-BPBPOX shows higher excellent power efficiency which is about 18% improved over 2-TNATA a commercial HIL material.

  基于苯噻嗪和苯氧咽的新型孔注入材料被合成，并通过紫外-可见光谱（UV-vis）、光致发光（PL）光谱和循环伏安法（CV）研究了合成材料的电光特性。1-BPNA-t-BPBP和1-BPNA-t-BPBPOX的玻璃化转变温度（Tg）分别为127 °C和200 °C，高于商业孔注入层（HIL）材料2-TNATA的110 °C。合成材料1-BPNA-t-BPBP和1-BPNA-t-BPBPOX的最高占据分子轨道（HOMO）能级分别为4.97 eV和4.91 eV，表明与ITO的HOMO（4.8 eV）和孔传输层（HTL）材料NPB的HOMO（5.4 eV）有良好的匹配。作为HIL在OLED器件中使用合成材料后，1-BPNA-t-BPBPOX的功率效率为2.43 lm/W，高于2-TNATA的1.98 lm/W和1-BPNA-t-BPBP的1.39 lm/W。这些结果表明，1-BPNA-t-BPBPOX表现出更高的功率效率，约比商业HIL材料2-TNATA提高了18%。
• NEW EMITTER MATERIALS AND MATRIX MATERIALS FOR OPTOELECTRONIC AND ELECTRONIC COMPONENTS, IN PARTICULAR ORGANIC LIGHT-EMITTING DIODES (OLEDS)
  申请人：Technische Universität Dresden

  公开号：US20210167304A1

  公开（公告）日：2021-06-03

  The invention relates to compounds, comprising at least one donor group and at least one acceptor group, in which the transition energy of the lowest excited triplet hack into the ground state both of the corresponding donor molecule and of the corresponding acceptor molecule being at least 2.2 eV, and the use thereof as an emitter or a carrier material in an optoelectronic component.
• [EN] CHROMOPHORE COMPOUNDS AND ORGANIC ELECTROLUMINESCENC DISPLAY DEVICE COMPRISING THE SAME<br/>[FR] COMPOSES CHROMOPHORES ET DISPOSITIF D'AFFICHAGE ELECTROLUMINESCENT ORGANIQUE COMPRENANT CES COMPOSES
  申请人：DOOSAN CORP

  公开号：WO2006041263A1

  公开（公告）日：2006-04-20

  The present invention relates to chromophore compounds applicable to any one of a hole injection layer (HIL)1 a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL) and an electron injection layer (EIL) of an organic electroluminescence display device. The compound is a derivative of phenothiazine, phenoxazine, phenoxathin, acridine, phenazasiline, or 9-aza-10- germa-anthracene. The compound has a substituent selected from the group consisting of a substituted or unsubstituted linear or branched alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl. The substituent may include at least one substituent selected from the group consisting of an alkyl, an alkoxy, a cycloalkyl, an alkenyl, an alkynyl, an aryl, a heteroaryl, a halogen such as F, Cl, Br, or I, aliphatic amine, aromatic amine, and an aryloxy.
• Highly Efficient New Hole Injection Materials for Organic Light Emitting Diodes Base on Phenothiazine Derivatives
  作者：Beomjin Kim、Jaehyun Lee、Youngil Park、Changjun Lee、Jong Wook Park

  DOI：10.1166/jnn.2014.8456

  日期：2014.8.1

  New hole injection materials for OLED based on phenothiazine were synthesized, and the electro-optical properties of synthesized materials were examined by through UV-Vis. and photoluminescence spectroscopy as well as cyclic voltammetry. 1-NDD-t-BPBP and 2-NDD-t-BPBP showed Tg of 180 and 177 °C. These are higher than that (110 °C) of 2-TNATA, commercial HIL material. As for the HOMO level of the synthesized materials, 1-NDD-t-BPBP and 2-NDD-t-BPBP were 4.99 and 5.02 eV, indicating well-matched values between HOMO (4.8 eV) of ITO and HOMO (5.4 eV) of NPB, HTL material. In addition, judging from the fact that the synthesized materials both barely showed any absorption in the range of over 450 nm, the synthesized materials could be effectively used as an HIL material. The synthesized materials were used as the HIL in OLED device, yielding luminance efficiencies of 4.51 cd/A (1-NDD-t-BPBP) and 4.44 cd/A (2-NDD-t-BPBP). These results indicated that 1-NDD-t-BPBP shows more excellent luminance efficiency which is about 11% improved over 2-TNATA a commercial HIL material.

  基于苯噻嗪的新孔注入材料被合成，合成材料的电光性能通过紫外-可见光光谱、光致发光光谱以及循环伏安法进行了测试。1-NDD-t-BPBP和2-NDD-t-BPBP的玻璃化转变温度分别为180°C和177°C，均高于商业HIL材料2-TNATA的110°C。关于合成材料的HOMO能级，1-NDD-t-BPBP和2-NDD-t-BPBP分别为4.99和5.02 eV，表明它们的HOMO值与ITO的4.8 eV和HTL材料NPB的5.4 eV之间匹配良好。此外，从合成材料在450 nm以上的波长范围内几乎没有吸收的事实来看，合成材料可以有效作为HIL材料。合成材料被用作OLED器件中的HIL，产生的光致效率分别为4.51 cd/A（1-NDD-t-BPBP）和4.44 cd/A（2-NDD-t-BPBP）。这些结果表明，1-NDD-t-BPBP表现出更优越的光致效率，比商业HIL材料2-TNATA提高约11%。