2-(3,5-bis(carbazol-9-yl)phenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole | 1258947-41-9

• 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: 2-(3,5-bis(carbazol-9-yl)phenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole
• 英文别名: 2-(3,5-dicarbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole；2-[3,5-di(carbazol-9-yl)phenyl]-5-(3-methoxyphenyl)-1,3,4-oxadiazole
• CAS: 1258947-41-9
• 化学式: C₃₉H₂₆N₄O₂
• 分子量: 582.661
• InChiKey: WHRYUGSKTJMXDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-bis(carbazol-9-yl)phenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-(5-(3,5-bis(carbazol-9-yl)phenyl)-1,3,4-oxadiazol-2-yl)-phenoxy)ethyl methacrylate
  参考文献：
  名称：

  Polymers with Carbazole-Oxadiazole Side Chains as Ambipolar Hosts for Phosphorescent Light-Emitting Diodes

  摘要：

  Polymethacrylates, polystyrenes, and polynorbornenes bearing 2-(3-(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole, 2-(4-(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole, 2-(3,5-di(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole) groups linked to the polymer backbone through the 3-position of their terminal phenyl groups have been synthesized for use as solution-processable ambipolar hosts for phosphorescent light-emitting diodes. The polymers exhibit good thermal stabilities, with no weight loss below 350 degrees C, and have glass-transition temperatures in the range 118-209 degrees C. Spectroscopic, electrochemical, and quantum-chemical data for small-molecule model compounds suggest that the side chain groups are suitable hosts for a range of phosphors, including the green-emitter fac-tris(2-phenylpyridinato-N,C-2')iridium (Ir(ppy)(3)). Light-emitting diodes were fabricated, each with a solution-processed photo-cross-linked hole-transport layer, a solution-processed emissive layer composed of a carbazole-oxadiazole-functionalized polymethacrylate doped with Ir(ppy)3, and an evaporated electron-transport layer. The polymer with 2-(3,5-(dicarbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole units in the side chain exhibited the lowest turn-on voltage (6.0 V), and the highest efficiency (external quantum efficiency of 10.0%, current efficiency of 34.1 cd/A).

  DOI：

  10.1021/cm201562p
• 作为产物：
  描述：

  3,5-diiodobenzohydrazide 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 2-(3,5-bis(carbazol-9-yl)phenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Polymers with Carbazole-Oxadiazole Side Chains as Ambipolar Hosts for Phosphorescent Light-Emitting Diodes

  摘要：

  Polymethacrylates, polystyrenes, and polynorbornenes bearing 2-(3-(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole, 2-(4-(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole, 2-(3,5-di(carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole) groups linked to the polymer backbone through the 3-position of their terminal phenyl groups have been synthesized for use as solution-processable ambipolar hosts for phosphorescent light-emitting diodes. The polymers exhibit good thermal stabilities, with no weight loss below 350 degrees C, and have glass-transition temperatures in the range 118-209 degrees C. Spectroscopic, electrochemical, and quantum-chemical data for small-molecule model compounds suggest that the side chain groups are suitable hosts for a range of phosphors, including the green-emitter fac-tris(2-phenylpyridinato-N,C-2')iridium (Ir(ppy)(3)). Light-emitting diodes were fabricated, each with a solution-processed photo-cross-linked hole-transport layer, a solution-processed emissive layer composed of a carbazole-oxadiazole-functionalized polymethacrylate doped with Ir(ppy)3, and an evaporated electron-transport layer. The polymer with 2-(3,5-(dicarbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole units in the side chain exhibited the lowest turn-on voltage (6.0 V), and the highest efficiency (external quantum efficiency of 10.0%, current efficiency of 34.1 cd/A).

  DOI：

  10.1021/cm201562p

文献信息

• [EN] 2-ALKYL-5-PHENYL OXADIAZOLE-CARBAZOLE HOSTS FOR GUEST EMITTERS<br/>[FR] HÔTES DE 2-ALKYL-5-PHÉNYL-OXADIAZOLE-CARBAZOLE POUR ÉMETTEURS HÉBERGÉS
  申请人：GEORGIA TECH RES INST

  公开号：WO2012088316A1

  公开（公告）日：2012-06-28

  The various inventions and/or their embodiments disclosed herein relate to and include 2-alkyl-5-phenyl-1,3,4-oxadiazole-carbazole ("2-APOC") small molecules having both hole carrying and electron carrying groups bound thereto, and the use of such ambipolar polymers, copolymers, and/or small molecules as host materials for carrying holes, electrons, and/or excitons into contact with guest light emitters, for use in the emissive layers of electronic devices such as organic light emitting diodes.

  本文披露的各种发明和/或其具体实施例涉及并包括具有既携带空穴又携带电子团的2-烷基-5-苯基-1,3,4-噁二唑-咔唑（"2-APOC"）小分子，以及将这种两性聚合物、共聚物和/或小分子用作载荷空穴、电子和/或激子与客体发光体接触的基材的使用，用于有机发光二极管等电子器件的发射层。
• [EN] POLYMERIZABLE AMBIPOLAR HOSTS FOR PHOSPHORESCENT GUEST EMITTERS<br/>[FR] HÔTES AMBIPOLAIRES POLYMÉRISABLES POUR ÉMETTEURS INVITÉS PHOSPHORESCENTS
  申请人：GEORGIA TECH RES INST

  公开号：WO2010149620A1

  公开（公告）日：2010-12-29

  The inventions describe disclosed and described herein relate to polymerizable ambipolar monomers, useful for making polymer or copolymer host materials for guest phosphorescent metal complexes, which together can form emission layers of organic light emitting diodes (OLEDs). Methods of making the ambipolar monomers are also described. Formula (I) wherein at least one of the R1, R2 and R3 groups is an optionally substituted carbazole group.

  本发明涉及可聚合的两性单体，用于制备用于客体磷光金属配合物的聚合物或共聚物基体材料，二者共同形成有机发光二极管（OLEDs）的发射层。还描述了制备两性单体的方法。其中，至少有一个R1、R2和R3基团是可选择取代的咔唑基团的化学式（I）。
• [EN] CARBAZOLE SUBSTITUTED TRIAZOLE, TRIAZINE, AND TETRAZINE AMBIPOLAR HOST MATERIALS AND DEVICES<br/>[FR] MATÉRIAUX HÔTES AMBIPOLAIRES À BASE DE TRIAZOLE, DE TRIAZINE ET DE TÉTRAZINE, SUBSTITUÉS PAR CARBAZOLE, ET DISPOSITIFS
  申请人：GEORGIA TECH RES INST

  公开号：WO2014011491A1

  公开（公告）日：2014-01-16

  Disclosed herein are ambipolar host compounds represented by formula (I): (I), wherein: a) at least one of the R1, R2 and R3 groups is an optionally substituted carbazole group, and the remaining of R1, R2 and R3 are independently selected from hydrogen, halogen and a C1-20 organic group; b) R4 is an optionally substituted alkyl group, an optionally substituted heteroalkyl group, a substituted aryl group comprising at least one heteroatom in the substituent, or an optionally substituted heteroaryl group; and c) Y is selected from, and, wherein R5 is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group, and wherein R6 is hydrogen, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group. The compounds can be used in OLED devices.

  本文揭示了由式(I)表示的双极主体化合物：(I)，其中：a) R1、R2和R3中至少一个是可选取代的咔唑基团，其余的R1、R2和R3独立地选自氢、卤素和C1-20有机基团；b) R4是可选取代的烷基基团、可选取代的杂环烷基基团、带有至少一个杂原子的取代芳基基团或可选取代的杂芳基基团；c) Y选自，并且其中R5是可选取代的芳基基团、可选取代的杂芳基基团、可选取代的烷基基团或可选取代的杂环烷基基团，而R6是氢、可选取代的芳基基团、可选取代的杂芳基基团、可选取代的烷基基团或可选取代的杂环烷基基团。这些化合物可用于OLED器件。
• AMBIPOLAR SMALL MOLECULE HOSTS FOR PHOSPHORESCENT GUEST EMITTERS
  申请人：Zhang Yadong

  公开号：US20120168732A1

  公开（公告）日：2012-07-05

  The inventions describe disclosed and described herein relate to ambipolar small molecule host materials for guest phosphorescent metal complexes. Methods of making the ambipolar small molecules are also described. These ambipolar small molecules, which comprise both an oxadiazole and one or more carbazole groups, can be used to make the emission layers of unexpectedly efficient OLED devices containing the materials of the inventions, wherein (I) at least one of the R 1 , R 2 and R 3 groups is an optionally substituted carbazole group.

  本发明涉及用于客体磷光金属配合物的双极小分子主体材料的发明和描述。还描述了制造双极小分子的方法。这些双极小分子包括氧化二唑和一个或多个咔唑基团，可用于制造意外高效的OLED器件的发射层，其中至少R1、R2和R3中的一个是可选取代的咔唑基团。
• POLYMERIZABLE AMBIPOLAR HOSTS FOR PHOSPHORESCENT GUEST EMITTERS
  申请人：Zhang Yadong

  公开号：US20120172556A1

  公开（公告）日：2012-07-05

  The inventions describe disclosed and described herein relate to polymerizable ambipolar monomers, useful for making polymer or copolymer host materials for guest phosphorescent metal complexes, which together can form emission layers of organic light emitting diodes (OLEDs). Methods of making the ambipolar monomers are also described. Formula (I) wherein at least one of the R 1 , R 2 and R 3 groups is an optionally substituted carbazole group.

  本发明涉及可聚合的双极性单体，用于制备用于客体磷光金属络合物的高分子或共聚物主体材料，这些材料可以与一起形成有机发光二极管（OLED）的发射层。还描述了制备双极性单体的方法。其中至少一个R1、R2和R3基团是可选择取代的咔唑基团的公式（I）。