Macrocyclic and Acyclic Bis(2,5‐diphenyl‐1,3,4‐oxadiazole)s with Electron‐Transporting and Hole‐Blocking Ability in Organic Electroluminescent Devices

Ono, Katsuhiko; Ezaka, Seiichi; Higashibata, Akinori; Hosokawa, Ryohei; Ohkita, Masakazu; Saito, Katsuhiro; Suto, Michitaka; Tomura, Masaaki; Matsushita, Yosuke; Naka, Shigeki; Okada, Hiroyuki; Onnagawa, Hiroyoshi

doi:10.1002/macp.200500122

Cited by 10 publications

(7 citation statements)

References 37 publications

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“…38 Cyclic and the acyclic derivatives of bis(2,5-diphenyl-1,3,4-oxadiazole) (CSD codes DAXBOU and DAXBUA) have been successfully tested in devices. 39 The acyclic isomer shows a large hole-blocking capacity, while the cyclic one improves the efficiency. 1,3bis[(4-tertbutylphenyl)-1,3,4-oxadiazolyl]phenylene (CSD code XIZDOZ) proved to be good hole-blocking and electron-transporting material when tested in the device.…”

Section: ■ Introductionmentioning

confidence: 99%

“…To name a few, specifically, symmetrically substituted ones, meta -terphenyloxadiazole derivative (CSD code TEDGIU) has been used as an electron-transport material in fluorescent devices; it was found to substantially improve the performance . Cyclic and the acyclic derivatives of bis(2,5-diphenyl-1,3,4-oxadiazole) (CSD codes DAXBOU and DAXBUA) have been successfully tested in devices . The acyclic isomer shows a large hole-blocking capacity, while the cyclic one improves the efficiency.…”

Section: Introductionmentioning

confidence: 99%

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Toward Designing Efficient Multifunctional Bipolar Molecules: DFT Study of Hole and Electron Mobilities of 1,3,4-Oxadiazole Derivatives

2015

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With a general aim to analyze molecules containing 1,3,4-oxadiazole moiety for charge transport in organic light-emitting diode devices, in this study we use density functional theory methods to compute reorganization energies, transfer integrals, and hole and electron mobilities of a very large number of symmetrically substituted small and large oxadiazole derivatives retrieved from Cambridge Structural Database. The study reveals that for the majority of small planar molecules, the reorganization energies are large, and the transfer integral plays a crucial role in the charge transport. In the case of large planar molecules, small reorganization energies leading to large drift mobility for both hole and electron transport is observed. The detailed analyses of the geometry and molecular orbitals of the molecules along with the pathways in the solid state were performed, which should be helpful for improving the design of oxadiazole derivatives for multifunctional bipolar properties.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Toward Designing Efficient Multifunctional Bipolar Molecules: DFT Study of Hole and Electron Mobilities of 1,3,4-Oxadiazole Derivatives

2015

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“…Up to now, various electron-transporting materials with 1,3,4-oxadiazole system have been synthesized and investigated for application in EL devices (Hughes & Bryce, 2005). The research of crystal structures is important for the design of electron-transporting materials (Ono et al 2005;Ono et al 2008), because these properties depend on their molecular arrangements in the solid state. Thus, we synthesized the title compound (I) as a novel 1,3,4-oxadiazole derivative and investigated its molecular and crystal structure.…”

Section: Supporting Informationmentioning

confidence: 99%

5,5′-Di-4-pyridyl-2,2′-(5-tert-butyl-m-phenylene)bis(1,3,4-oxadiazole)

Ono¹,

Tsukamoto²,

Tomura³

2009

Acta Cryst E

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The title compound, C24H20N6O2, is a novel 1,3,4-oxadiazole derivative which has potential as an electron-transporting material in organic electroluminescent (EL) devices. In the crystal, the molecular framework is almost planar with an r.m.s. deviation of 0.091 (4) Å and it exists in an E form. Intramolecular C—H⋯O and C—H⋯N hydrogen bonds are observed between the benzene and 1,3,4-oxadiazole rings. The tert-butyl group is disordered over two sites, with occupancy factors of 0.78 (1) and 0.22 (1) for the major and minor orientations, respectively. In the crystal structure, molecules aggregate via C—H⋯N interactions, forming molecular tapes along the b axis, which aggregate to form a molecular sheet via C—H⋯N interactions.

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“…The increasing interest in the synthesis of 2,5-substituted-1,3,4-oxadiazoles can be attributed to their remarkable photophysical properties , but also because they have been evaluated as promising antiviral, , antibacterial, anti-inflammatory/analgesic or antifungal agents, as well as inhibitors of various enzymes . Bis-1,3,4-oxadiazoles have emerged as important targets for development of organic light emitting diodes (OLEDs) − as a consequence of their improved optoelectronic properties with an increasing number of the heterocyclic rings.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes

et al. 2013

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Reaction between ortho-phthalaldehyde and various aroylhydrazines unexpectedly yields N-(1-(2-aryl-hydrazono)isoindolin-2-yl)benzamides as major products along with the predictable 1,2-bis-aroylhydrazones. NMR investigation of the major reaction products indicate the presence of a mixture of geometrical isomers, in various ratios. Single crystal X-ray diffraction confirms the proposed structure and indicates a Z configuration of the C═N double bond substitutents. Optimization of the condensation reaction conditions enabled quantitative isolation of the cyclic isomer. Oxidation of the isomers with bis(trifluoroacetoxy)iodobenzene (PIFA) leads to rapid formation of new highly fluorescent 1,2-bis(5-aryl-1,3,4-oxadiazol-2-yl)benzenes.

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Macrocyclic and Acyclic Bis(2,5‐diphenyl‐1,3,4‐oxadiazole)s with Electron‐Transporting and Hole‐Blocking Ability in Organic Electroluminescent Devices

Cited by 10 publications

References 37 publications

Toward Designing Efficient Multifunctional Bipolar Molecules: DFT Study of Hole and Electron Mobilities of 1,3,4-Oxadiazole Derivatives

Toward Designing Efficient Multifunctional Bipolar Molecules: DFT Study of Hole and Electron Mobilities of 1,3,4-Oxadiazole Derivatives

5,5′-Di-4-pyridyl-2,2′-(5-tert-butyl-m-phenylene)bis(1,3,4-oxadiazole)

Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes

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