1,5-Diazocine-Based Diaryl Ketones: Design, Synthesis, and Optoelectronic Properties

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2024-10-04 DOI:10.1002/jhet.4915

Anjitha Sebastian, Vibhu Darshan, Bijoy Nharangatt, Vijay Kumar Maka, Amrutham Linet, Simi Achankunju, Masaki Nagaoka, Shigeyuki Yagi, Narayanan Unni K. N., Ishita Neogi

{"title":"1,5-Diazocine-Based Diaryl Ketones: Design, Synthesis, and Optoelectronic Properties","authors":"Anjitha Sebastian, Vibhu Darshan, Bijoy Nharangatt, Vijay Kumar Maka, Amrutham Linet, Simi Achankunju, Masaki Nagaoka, Shigeyuki Yagi, Narayanan Unni K. N., Ishita Neogi","doi":"10.1002/jhet.4915","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>Three novel heterocyclic host based on diaryl ketone-tethered 1,5-diazocines were designed and synthesized for applications in phosphorescent organic light-emitting diodes (PhOLEDs). The hosts were derived by anchoring the naphthyl ketone (TBN), anthryl ketone (TBA), and phenanthryl ketone (TBP) to the 1,5-diazocine core. The materials were successfully characterized using spectroscopic techniques. TBN and TBP exhibited low external quantum efficiency of 1.5% and 1.9% when explored as hosts in PhOLED devices. Among the series, TBP exhibited the highest luminance of 4160 cd/m<sup>2</sup>, maximum luminance efficiency of 6.3 cd/A, and power efficiency of 3.21 lm/w, when doped with Ir(ppy)<sub>3</sub> in PhOLED. Nevertheless to our surprise, TBA manifested the lowest device performance than other TBs as a host due to low carrier mobility caused by a highly twisted structure as deciphered from the comparative analysis of single-crystal structure that could impede carrier transport crucial for efficient electroluminescence. The outcomes of electroluminescence were validated and explained with analysis of single-crystal structure, and also with the aid of density functional theory.</p>\n </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"2040-2049"},"PeriodicalIF":2.0000,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Heterocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4915","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

Abstract

Three novel heterocyclic host based on diaryl ketone-tethered 1,5-diazocines were designed and synthesized for applications in phosphorescent organic light-emitting diodes (PhOLEDs). The hosts were derived by anchoring the naphthyl ketone (TBN), anthryl ketone (TBA), and phenanthryl ketone (TBP) to the 1,5-diazocine core. The materials were successfully characterized using spectroscopic techniques. TBN and TBP exhibited low external quantum efficiency of 1.5% and 1.9% when explored as hosts in PhOLED devices. Among the series, TBP exhibited the highest luminance of 4160 cd/m², maximum luminance efficiency of 6.3 cd/A, and power efficiency of 3.21 lm/w, when doped with Ir(ppy)₃ in PhOLED. Nevertheless to our surprise, TBA manifested the lowest device performance than other TBs as a host due to low carrier mobility caused by a highly twisted structure as deciphered from the comparative analysis of single-crystal structure that could impede carrier transport crucial for efficient electroluminescence. The outcomes of electroluminescence were validated and explained with analysis of single-crystal structure, and also with the aid of density functional theory.

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.