4,6-双（3-（9H-咔唑-9-基）苯基）嘧啶 | 1262678-77-2

• 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
• 中文名称: 4,6-双（3-（9H-咔唑-9-基）苯基）嘧啶
• 英文名称: 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine
• 英文别名: 4,6-Bis(3-(9H-carbazol-9-yl)phenyl)pyrimidine；9-[3-[6-(3-carbazol-9-ylphenyl)pyrimidin-4-yl]phenyl]carbazole
• CAS: 1262678-77-2
• 化学式: C₄₀H₂₆N₄
• 分子量: 562.673
• InChiKey: LNNMKLNCLINVKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-(3-溴苯基)-9H-咔唑 在 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 potassium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 生成 4,6-双（3-（9H-咔唑-9-基）苯基）嘧啶
  参考文献：
  名称：

  RGB Phosphorescent Organic Light-Emitting Diodes by Using Host Materials with Heterocyclic Cores: Effect of Nitrogen Atom Orientations

  摘要：

  A series of host materials 1-7 containing various heterocyclic cores, like pyridine, pyrimidine, and pyrazine, were developed for RGB phosphorescent organic light-emitting diodes (OLEDs). Their energy levels can be tuned by the change of heterocyclic cores and their nitrogen atom orientations, and decrease of singlet-triplet exchange energy (Delta E-ST) was achieved with introducing one or two nitrogen atoms into the central arylene; this is also consistent with density functional theory calculations. Their carrier mobilities can also be tuned by the choice of heterocyclic cores, giving improved bipolarity compared with that without any heterocyclic cores. Due to the high triplet energy level of the developed host materials, well confinement of triplet excitons of blue emitter iridium(III) bis(4,6-(difluorophenyl)pyridinato-N,C-2') picolinate (FIrpic) was achieved except for 7 due to its low E-T. In contrast, triplet energy can be well confined on green emitter fac-tris-(2-phenylpyridine) iridium (Ir(PPy)(3)) and red emitter tris(1-phenylisoquinolinolato-C-2,N)iridium(III) (Ir(piq)(3)) for all the hosts, giving comparable lifetime (tau), photoluminescent quantum efficiency (eta(PL)), and radiative and nonradiative rate constants (k(r) and k(nr)). Highly efficient blue and green phosphorescent OLEDs were achieved for 2, exhibiting one of the highest ever efficiencies to date, especially at much brighter luminance for lighting applications. In comparison, the highest efficiencies hitherto were achieved for the red phosphorescent OLED based on 6, which can be attributed to its lower-lying LUMO level and the smallest Delta E-ST, giving improved electron injection and carrier balance. Different from the blue and green phosphorescent OLEDs based on FIrpic and Ir(PPy)(3), the host materials with lower-lying LUMO levels seem to be better hosts for a red emitter Ir(piq)(3), achieving improved efficiency and reduced efficiency roll-off at high current density.

  DOI：

  10.1021/cm102975d

文献信息

• Light-Emitting Element, Lighting Device, Light-Emitting Device, and Electronic Device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20160343968A1

  公开（公告）日：2016-11-24

  A light-emitting element includes a first electrode; a first light-emitting layer over the first electrode, containing a first phosphorescent compound and a first host material; a second light-emitting layer over the first light-emitting layer, containing a second phosphorescent compound and a second host material; a third light-emitting layer over the second light-emitting layer, containing a third phosphorescent compound and a third host material; and a second electrode over the third light-emitting layer. Between peaks of emission spectra of the first, second, and third phosphorescent compounds, the peak of the emission spectrum of the second phosphorescent compound is on the longest wavelength side and that of the emission spectrum of the third phosphorescent compound is on the shortest wavelength side. The third host material has higher triplet excitation energy than the first host material and the second host material.

  一个发光元件包括：第一电极；设置在第一电极上的第一发光层，包含第一磷光化合物和第一主体材料；设置在第一发光层上的第二发光层，包含第二磷光化合物和第二主体材料；设置在第二发光层上的第三发光层，包含第三磷光化合物和第三主体材料；以及设置在第三发光层上的第二电极。在第一、第二和第三磷光化合物的发射光谱的峰值之间，第二磷光化合物的发射光谱峰值位于最长波长侧，而第三磷光化合物的发射光谱峰值位于最短波长侧。第三主体材料具有高于第一主体材料和第二主体材料的三重态激发能。
• [EN] ORGANIC COMPOUND, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE<br/>[FR] COMPOSÉ ORGANIQUE, ÉLÉMENT ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTRONIQUE ET DISPOSITIF D'ÉCLAIRAGE
  申请人：SEMICONDUCTOR ENERGY LAB

  公开号：WO2018167606A1

  公开（公告）日：2018-09-20

  A novel organic compound is provided. That is, a novel organic compound that is effective in improving reliability of a light-emitting element is provided. The organic compound includes a condensed ring including a pyrimidine ring and is represented by General Formula (G1). In General Formula (G1), A represents a group having 6 to 100 carbon atoms and includes at least one of an aromatic ring and a heteroaromatic ring. The aromatic ring and the heteroaromatic ring may each include a substituent. Furthermore, Q represents oxygen or sulfur. A ring X represents a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring.

  提供了一种新的有机化合物。也就是说，提供了一种能够提高发光元件可靠性的新型有机化合物。该有机化合物包括一个包含嘧啶环的缩合环，并由通用式（G1）表示。在通用式（G1）中，A代表含有6至100个碳原子的基团，并且至少包括一个芳香环和一个杂芳环中的一个。芳香环和杂芳环中每个都可以包括一个取代基。此外，Q代表氧或硫。环X代表取代或未取代的萘环或取代或未取代的菲环。
• [EN] LIGHT-EMITTING DEVICE, LIGHT-EMITTING APPARATUS, ELECTRONIC DEVICE, AND LIGHTING DEVICE<br/>[FR] ÉLÉMENT ÉLECTROLUMINESCENT, APPAREIL ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTRONIQUE ET DISPOSITIF D'ÉCLAIRAGE
  申请人：SEMICONDUCTOR ENERGY LAB

  公开号：WO2020053689A1

  公开（公告）日：2020-03-19

  To provide a light-emitting device not only including a light-emitting layer in which energy is efficiently transferred from a host material to a guest material but also having high reliability. The light-emitting device not only includes a light-emitting layer in which the T1 levels and the S1 levels of a host material and a guest material fall within certain ranges so that energy can be efficiently transferred from the host material to the guest material and but also has improved reliability.

  为了提供一种发光装置，不仅包括一个发光层，其中能量从主体材料有效地转移到客体材料，而且具有很高的可靠性。这种发光装置不仅包括一个发光层，其中主体材料和客体材料的T1能级和S1能级落在一定范围内，以便能量可以有效地从主体材料转移到客体材料，而且还具有改善的可靠性。
• Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20170092881A1

  公开（公告）日：2017-03-30

  A novel organometallic complex with high reliability is provided. The organometallic complex includes iridium and ligands coordinated to the iridium. The ligands are a dipivaloylmethanato ligand and a ligand including a phenyl group to which an alkyl group is bonded and which is bonded to the 5-position of a pyrazine ring. In the formula, Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; and R1 and R2 each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R3 to R6 each independently represent any of hydrogen, halogen, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted hydroxyl group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

  提供了一种具有高可靠性的新型有机金属配合物。这种有机金属配合物包括铱和配体与铱配位。配体是二戊酰丙酮配体和包括苯基与烷基键合并与吡啶环的5位键合的配体。在公式中，Ar代表具有6到13个碳原子的取代或未取代芳基基团；R1和R2分别独立地代表具有1到6个碳原子的取代或未取代烷基基团。R3到R6分别独立地代表氢、卤素、氰基、取代或未取代氨基、取代或未取代羟基、取代或未取代巯基、具有1到6个碳原子的取代或未取代烷基基团、具有6到13个碳原子的取代或未取代芳基基团以及具有3到12个碳原子的取代或未取代杂环基团中的任意一种。
• [EN] ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE<br/>[FR] COMPLEXE ORGANOMÉTALLIQUE, ÉLÉMENT ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTRONIQUE ET DISPOSITIF D'ÉCLAIRAGE
  申请人：SEMICONDUCTOR ENERGY LAB

  公开号：WO2018109621A1

  公开（公告）日：2018-06-21

  A novel organometallic complex with high emission efficiency is provided. The organometallic complex, which is represented by General Formula (G1), includes iridium and a ligand including an aryl group including a cyano group at the 1-position of a benzimidazole skeleton and a phenyl group at the 2-position of the benzimidazole skeleton. (In the formula, Ar1 represents an aryl group having one or more substituents and 6 to 13 carbon atoms, and Arl includes at least one cyano group as the substituent. Each of R1 to R8 separately represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group.)

  提供了一种具有高发射效率的新型有机金属配合物。该有机金属配合物由通用公式（G1）表示，包括铱和一种配体，其中该配体包括一个芳基团，在苯并咪唑骨架的1-位置带有一个氰基团和在苯并咪唑骨架的2-位置带有一个苯基团。（在公式中，Ar1代表具有一个或多个取代基和6到13个碳原子的芳基团，Arl至少包括一个氰基作为取代基。R1至R8中的每一个分别代表氢、具有1到6个碳原子的取代或未取代烷基基团、具有3到6个碳原子的取代或未取代环烷基基团、具有6到13个碳原子的取代或未取代芳基基团、具有3到12个碳原子的取代或未取代杂环芳基基团和一个氰基。）