吲哚[3,2,1-jk]咔唑衍生的窄带紫蓝色荧光团：通过发色团杂耍调节光学和电致发光特性,The Journal of Organic Chemistry

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吲哚[3,2,1-jk]咔唑衍生的窄带紫蓝色荧光团：通过发色团杂耍调节光学和电致发光特性
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-05-05 , DOI: 10.1021/acs.joc.2c00322
Rajendra Kumar Konidena ₁ , Seyoung Oh ₁ , Seokwoo Kang ₁ , Sang-Shin Park ₁ , Hayoon Lee ₁ , Jongwook Park ₁

Affiliation

用于窄带紫色荧光团的刚性多环芳烃结构单元的开发受到了极大的关注。在此，我们设计并合成了两种新型三角形刚性结构单元，即 2,5-二叔丁基吲哚[3,2,1- jk ]咔唑（tBuICz）和2,11-二叔丁基吲哚[ 3,2,1- jk ]carbazole-4-carbonitrile ( tBuICzCN )，并用不同的发色团将它们束缚，产生一系列紫蓝色荧光团，即。, ICzTPA–ICzPICN，并研究了它们的结构-功能关系。附加的发色团和氰基单元在控制化合物的光学和电学性质方面发挥了至关重要的作用。除三苯胺取代衍生物外，这些化合物均显示出纯紫色发射（λ _em ≤ 403 nm）。有趣的是，这些化合物表现出窄带发射，半高全宽 ≤ 40 nm，这归因于 ICz 核心的刚性。化合物的发射表现出正溶剂化显色性，这归因于激发态的光诱导分子内电荷转移。该化合物在T _{5d时表现出优异的热稳定性}≥ 363℃。由于其富含电子的性质，与它们的同类物相比，具有三苯胺的衍生物显示出较高的 HOMO。当我们将这些材料应用于有机发光二极管时，ICzPI在该系列中表现出色，EQE_最大值为 3.07%，电流效率为 1.04 cd/A。值得注意的是，它的 CIEy ∼ 0.046 与 Rec.2020 深蓝色标准（CIEy ∼ 0.046）精确匹配。

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Indolo[3,2,1-jk]carbazole-Derived Narrowband Violet–Blue Fluorophores: Tuning the Optical and Electroluminescence Properties by Chromophore Juggling

The development of rigid polyaromatic building blocks for narrowband violet fluorophores has received tremendous attention. Herein, we designed and synthesized two new triangle-shaped rigid building blocks, namely, 2,5-di-tert-butylindolo[3,2,1-jk]carbazole (tBuICz) and 2,11-di-tert-butylindolo[3,2,1-jk]carbazole-4-carbonitrile (tBuICzCN), and tethered them with different chromophores to yield a series of violet–blue fluorophores, viz., ICzTPA–ICzPICN, and studied their structure–function relationship. The appended chromophores and cyano unit played a vital role in controlling the optical and electrical properties of the compounds. Except triphenylamine-substituted derivatives, the compounds showed pure violet emission (λ_em ≤ 403 nm). Intriguingly, the compounds exhibited narrow-band emission with a full-width at half-maximum ≤ 40 nm, attributed to the rigidity of the ICz core. The emission of the compounds displayed positive solvatochromism, which is ascribed to the photoinduced intramolecular charge transfer in the excited state. The compounds revealed excellent thermal robustness with T_5d ≥ 363 °C. The triphenylamine-featuring derivatives displayed a high-lying HOMO compared to their congeners due to their electron-rich nature. When we applied these materials in organic light-emitting diodes, ICzPI outperformed in the series with an EQE_max of 3.07% and a current efficiency of 1.04 cd/A. Notably, its CIEy ∼ 0.046 precisely matched with the Rec.2020 standard of deep-blue color (CIEy ∼ 0.046).

更新日期：2022-05-05

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