Mohan Gandhi Devulapally, Kiun Cheong, Jangho Moon, Rajkumar Nagavath, Jae Hee Lee, Jun Yeob Lee, Wan Pyo Hong
{"title":"硼氧掺杂π扩展纳米石墨烯:有机发光二极管的发光材料","authors":"Mohan Gandhi Devulapally, Kiun Cheong, Jangho Moon, Rajkumar Nagavath, Jae Hee Lee, Jun Yeob Lee, Wan Pyo Hong","doi":"10.1002/adom.202500848","DOIUrl":null,"url":null,"abstract":"<p>Expanding the molecular framework of hexabenzo[<i>a,c,fg,j,l,op</i>]tetracene (HBT) via heteroatom incorporation and topological edge control is crucial for achieving desired photophysical properties. However, synthesizing heteroatom-doped HBT derivatives remains highly challenging, and effective molecular design strategies have not yet been established. Herein, the synthesis of boron (B)- and oxygen (O)-doped expanded HBT (<b>BO-HBT</b>) is carried using a sequential Scholl cyclization strategy. This work is the first example of a B/O-expanded HBT molecule, demonstrating that heteroatom incorporation and peripheral alkyl group modifications enable accurate tuning of its electronic structure and photonic properties. Consequently, <b>BO-HBT</b> exhibits a reduced bandgap (2.55 eV), robust electrochemical stability, a horizontal emitting dipole orientation ratio of 88%, and a high photoluminescence quantum yield of 62.8% in toluene. Density functional theory calculations further elucidate its fluorescence mechanism, revealing that all the frontier orbitals of <b>BO-HBT</b> are predominantly localized in the central pyrene and boron-containing parts and the peripheral biphenyl moieties play a minor role. Hence, the redox and photoluminescence properties of <b>BO-HBT</b> closely resemble those of <b>BO-BPP</b>, a structurally related B/O-fused pyrene system. Notably, <b>BO-HBT</b> demonstrated promising performance as an emitting dopant material in organic light-emitting diodes (OLEDs), achieving an external quantum efficiency of up to 6.2% in the pure green visible region and exceeding 10% in hyperfluorescent devices. These results represent the first successful demonstration of an HBT derivative as an emissive dopant in OLEDs and underscore BO-HBT's potential for advanced optoelectronic applications.</p>","PeriodicalId":116,"journal":{"name":"Advanced Optical Materials","volume":"13 28","pages":""},"PeriodicalIF":7.2000,"publicationDate":"2025-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Boron- and Oxygen-Doped π-Extended Nanographene: An Emitting Material for Organic Light-Emitting Diodes\",\"authors\":\"Mohan Gandhi Devulapally, Kiun Cheong, Jangho Moon, Rajkumar Nagavath, Jae Hee Lee, Jun Yeob Lee, Wan Pyo Hong\",\"doi\":\"10.1002/adom.202500848\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Expanding the molecular framework of hexabenzo[<i>a,c,fg,j,l,op</i>]tetracene (HBT) via heteroatom incorporation and topological edge control is crucial for achieving desired photophysical properties. However, synthesizing heteroatom-doped HBT derivatives remains highly challenging, and effective molecular design strategies have not yet been established. Herein, the synthesis of boron (B)- and oxygen (O)-doped expanded HBT (<b>BO-HBT</b>) is carried using a sequential Scholl cyclization strategy. This work is the first example of a B/O-expanded HBT molecule, demonstrating that heteroatom incorporation and peripheral alkyl group modifications enable accurate tuning of its electronic structure and photonic properties. Consequently, <b>BO-HBT</b> exhibits a reduced bandgap (2.55 eV), robust electrochemical stability, a horizontal emitting dipole orientation ratio of 88%, and a high photoluminescence quantum yield of 62.8% in toluene. Density functional theory calculations further elucidate its fluorescence mechanism, revealing that all the frontier orbitals of <b>BO-HBT</b> are predominantly localized in the central pyrene and boron-containing parts and the peripheral biphenyl moieties play a minor role. Hence, the redox and photoluminescence properties of <b>BO-HBT</b> closely resemble those of <b>BO-BPP</b>, a structurally related B/O-fused pyrene system. Notably, <b>BO-HBT</b> demonstrated promising performance as an emitting dopant material in organic light-emitting diodes (OLEDs), achieving an external quantum efficiency of up to 6.2% in the pure green visible region and exceeding 10% in hyperfluorescent devices. 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Boron- and Oxygen-Doped π-Extended Nanographene: An Emitting Material for Organic Light-Emitting Diodes
Expanding the molecular framework of hexabenzo[a,c,fg,j,l,op]tetracene (HBT) via heteroatom incorporation and topological edge control is crucial for achieving desired photophysical properties. However, synthesizing heteroatom-doped HBT derivatives remains highly challenging, and effective molecular design strategies have not yet been established. Herein, the synthesis of boron (B)- and oxygen (O)-doped expanded HBT (BO-HBT) is carried using a sequential Scholl cyclization strategy. This work is the first example of a B/O-expanded HBT molecule, demonstrating that heteroatom incorporation and peripheral alkyl group modifications enable accurate tuning of its electronic structure and photonic properties. Consequently, BO-HBT exhibits a reduced bandgap (2.55 eV), robust electrochemical stability, a horizontal emitting dipole orientation ratio of 88%, and a high photoluminescence quantum yield of 62.8% in toluene. Density functional theory calculations further elucidate its fluorescence mechanism, revealing that all the frontier orbitals of BO-HBT are predominantly localized in the central pyrene and boron-containing parts and the peripheral biphenyl moieties play a minor role. Hence, the redox and photoluminescence properties of BO-HBT closely resemble those of BO-BPP, a structurally related B/O-fused pyrene system. Notably, BO-HBT demonstrated promising performance as an emitting dopant material in organic light-emitting diodes (OLEDs), achieving an external quantum efficiency of up to 6.2% in the pure green visible region and exceeding 10% in hyperfluorescent devices. These results represent the first successful demonstration of an HBT derivative as an emissive dopant in OLEDs and underscore BO-HBT's potential for advanced optoelectronic applications.
期刊介绍:
Advanced Optical Materials, part of the esteemed Advanced portfolio, is a unique materials science journal concentrating on all facets of light-matter interactions. For over a decade, it has been the preferred optical materials journal for significant discoveries in photonics, plasmonics, metamaterials, and more. The Advanced portfolio from Wiley is a collection of globally respected, high-impact journals that disseminate the best science from established and emerging researchers, aiding them in fulfilling their mission and amplifying the reach of their scientific discoveries.