双氰吡啶4位芳基取代基对热激活延迟荧光和电致发光效率的影响

IF 3.8 3区材料科学 Q2 MATERIALS SCIENCE, MULTIDISCIPLINARY

Optical Materials Pub Date : 2025-04-09 DOI:10.1016/j.optmat.2025.117027

Pavel Arsenyan , Brigita Vigante , Ehsan Ullah Rashid , Karolis Leitonas , Dmytro Volyniuk , Pavels Dimitrijevs , Juozas Vidas Grazulevicius

{"title":"双氰吡啶4位芳基取代基对热激活延迟荧光和电致发光效率的影响","authors":"Pavel Arsenyan , Brigita Vigante , Ehsan Ullah Rashid , Karolis Leitonas , Dmytro Volyniuk , Pavels Dimitrijevs , Juozas Vidas Grazulevicius","doi":"10.1016/j.optmat.2025.117027","DOIUrl":null,"url":null,"abstract":"<div><div>Our research is on the side modification of the compound exhibiting efficient thermally activated delayed fluorescence (TADF) by different aryl acetylene moieties. The modification results in the synthesis of unique 2,6-bis-(3,6-di-tert-butyl-carbazol-9-yl)-4-[4-(4-substituted ethynyl) phenyl]-pyridine-3,5-dicarbonitriles. Organic light-emitting diodes with these compounds exhibit a wide range of external quantum efficiencies from 9.8 to12.5 to 17.3%. This wide variation in efficiency, which even surpassed that of the device with the reference emitter, is primarily attributed to the significant influence of the aromatic acetylenes on the TADF properties of the compounds. The presence of ferrocene moiety results in completely quenched emission of the compound. The attachment of phenyl ethynyl group induces efficient TADF due to the narrowing of singlet-triplet energy gap (ΔE<sub>ST</sub>) down to 0.07 eV. The spatial alignment of the singlet and triplet states is studied by quantum chemical computations demonstrating the effect of the modifications on the reduction of ΔE<sub>ST</sub> values. It is shown that the different efficiency of reverse intersystem crossing is caused by the different spin-orbit coupling values between singlet and triplet states. The proposed acetylene modifications offer a chemical approach to finely tune TADF properties and control conformer formations of donor-acceptor type emitters in the solid state, providing a practical tool for the future research and applications of TADF emitters.</div></div>","PeriodicalId":19564,"journal":{"name":"Optical Materials","volume":"163 ","pages":"Article 117027"},"PeriodicalIF":3.8000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An Impact of the Aryl Substituent in Position 4 of Dicyanopyridines on Efficiency of Thermally Activated Delayed Fluorescence and Electroluminescence\",\"authors\":\"Pavel Arsenyan , Brigita Vigante , Ehsan Ullah Rashid , Karolis Leitonas , Dmytro Volyniuk , Pavels Dimitrijevs , Juozas Vidas Grazulevicius\",\"doi\":\"10.1016/j.optmat.2025.117027\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Our research is on the side modification of the compound exhibiting efficient thermally activated delayed fluorescence (TADF) by different aryl acetylene moieties. The modification results in the synthesis of unique 2,6-bis-(3,6-di-tert-butyl-carbazol-9-yl)-4-[4-(4-substituted ethynyl) phenyl]-pyridine-3,5-dicarbonitriles. Organic light-emitting diodes with these compounds exhibit a wide range of external quantum efficiencies from 9.8 to12.5 to 17.3%. This wide variation in efficiency, which even surpassed that of the device with the reference emitter, is primarily attributed to the significant influence of the aromatic acetylenes on the TADF properties of the compounds. The presence of ferrocene moiety results in completely quenched emission of the compound. The attachment of phenyl ethynyl group induces efficient TADF due to the narrowing of singlet-triplet energy gap (ΔE<sub>ST</sub>) down to 0.07 eV. The spatial alignment of the singlet and triplet states is studied by quantum chemical computations demonstrating the effect of the modifications on the reduction of ΔE<sub>ST</sub> values. It is shown that the different efficiency of reverse intersystem crossing is caused by the different spin-orbit coupling values between singlet and triplet states. The proposed acetylene modifications offer a chemical approach to finely tune TADF properties and control conformer formations of donor-acceptor type emitters in the solid state, providing a practical tool for the future research and applications of TADF emitters.</div></div>\",\"PeriodicalId\":19564,\"journal\":{\"name\":\"Optical Materials\",\"volume\":\"163 \",\"pages\":\"Article 117027\"},\"PeriodicalIF\":3.8000,\"publicationDate\":\"2025-04-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Optical Materials\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0925346725003878\",\"RegionNum\":3,\"RegionCategory\":\"材料科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"MATERIALS SCIENCE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Optical Materials","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0925346725003878","RegionNum":3,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

我们的研究是通过不同的芳基乙炔基团对具有高效热激活延迟荧光（TADF）的化合物进行侧修饰。该修饰合成了独特的2,6-二-（3,6-二叔丁基-咔唑-9-基）-4-[4-（4-取代乙基）苯基]-吡啶-3,5-二碳腈。具有这些化合物的有机发光二极管表现出广泛的外部量子效率，从9.8到12.5到17.3%。这种效率的巨大变化，甚至超过了具有参考发射器的装置，主要归因于芳香乙炔对化合物的TADF性质的显著影响。二茂铁部分的存在导致化合物的完全淬灭发射。苯基乙基的附着使单重态-三重态能隙（ΔEST）缩小至0.07 eV，从而诱导了高效的TADF。通过量子化学计算研究了单重态和三重态的空间排列，证明了修改对ΔEST值降低的影响。结果表明，单重态和三重态的自旋轨道耦合值不同是导致系统间反向交叉效率不同的原因。所提出的乙炔修饰为精细调节TADF性质和控制固体施主-受主型发射体的构象提供了一种化学方法，为TADF发射体的未来研究和应用提供了实用工具。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

An Impact of the Aryl Substituent in Position 4 of Dicyanopyridines on Efficiency of Thermally Activated Delayed Fluorescence and Electroluminescence

Our research is on the side modification of the compound exhibiting efficient thermally activated delayed fluorescence (TADF) by different aryl acetylene moieties. The modification results in the synthesis of unique 2,6-bis-(3,6-di-tert-butyl-carbazol-9-yl)-4-[4-(4-substituted ethynyl) phenyl]-pyridine-3,5-dicarbonitriles. Organic light-emitting diodes with these compounds exhibit a wide range of external quantum efficiencies from 9.8 to12.5 to 17.3%. This wide variation in efficiency, which even surpassed that of the device with the reference emitter, is primarily attributed to the significant influence of the aromatic acetylenes on the TADF properties of the compounds. The presence of ferrocene moiety results in completely quenched emission of the compound. The attachment of phenyl ethynyl group induces efficient TADF due to the narrowing of singlet-triplet energy gap (ΔE_ST) down to 0.07 eV. The spatial alignment of the singlet and triplet states is studied by quantum chemical computations demonstrating the effect of the modifications on the reduction of ΔE_ST values. It is shown that the different efficiency of reverse intersystem crossing is caused by the different spin-orbit coupling values between singlet and triplet states. The proposed acetylene modifications offer a chemical approach to finely tune TADF properties and control conformer formations of donor-acceptor type emitters in the solid state, providing a practical tool for the future research and applications of TADF emitters.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Optical Materials 工程技术-材料科学：综合

CiteScore

6.60

自引率

12.80%

发文量

1265

审稿时长

38 days

期刊介绍： Optical Materials has an open access mirror journal Optical Materials: X, sharing the same aims and scope, editorial team, submission system and rigorous peer review. The purpose of Optical Materials is to provide a means of communication and technology transfer between researchers who are interested in materials for potential device applications. The journal publishes original papers and review articles on the design, synthesis, characterisation and applications of optical materials. OPTICAL MATERIALS focuses on: • Optical Properties of Material Systems; • The Materials Aspects of Optical Phenomena; • The Materials Aspects of Devices and Applications. Authors can submit separate research elements describing their data to Data in Brief and methods to Methods X.