Disilanyl Double‐Pillared Bisanthracene: A Bipolar Carrier Transport Material for Organic Light‐Emitting Diode Devices

Nakanishi, Waka; Hitosugi, Shunpei; Piskareva, Anna; Shimada, Yusuke; Taka, Hideo; Kita, Hiroshi; Isobe, Hiroyuki

doi:10.1002/anie.201002432

Cited by 54 publications

(18 citation statements)

References 45 publications

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“…The minimum of CB is higher than that of Si DPBA, which is consistent with Ref. 41, in which the LUMO of anthracene is higher than that of Si DPBA, but their VB maxima are comparable.…”

Section: Band Structuresupporting

confidence: 89%

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A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)

et al. 2011

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A novel anthracene derivative, disilanyl double-pillared bisanthracene ( Si DPBA), has been recently synthesized, which effectively functions as a bipolar carrier transport material in OLEDs. Its charge transport properties have been systemically investigated by band model and hopping model. Band structure calculations of Si DPBA show that the dispersions of the larger valence band and conduction band are comparable, which demonstrates that both electron and hole are favoured for transport, and that Si DPBA has the potential to be used as bipolar transport material from the viewpoint of band model. The density of states and transfer integrals in the main pathways show that it is the edge-to-face CH···p interaction that determines the charge transport property, and that the SiMe2 group contibutes little to it. The calculated charge mobilities of holes and electrons are 0.461 and 0.116 cm 2 ·V -1 ·s -1 , respectively. They are the same order of magnitude, and the electron mobility is on the order of magnitude of perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) derivatives (0.34 cm 2 ·V -1 ·s -1 ). Both models demonstrate that · Si DPBA has the potential to be used as a bipolar transport material.Résumé : On a récemment réalisé la synthèse d'un nouveau dérivé de l'anthracène, un disilanyl bisanthracène à double pilier (« Si DPBA ») qui fonctionne effectivement comme un matériel de transfert de charge bipolaire dans les diodes électrolu-minescentes organiques (DELO). On a étudié d'une façon systématique ses propriétés de transfert de charge par le modèle de bande et le modèle des sauts. Les calculs de structure de bande pour le « Si DPBA » montrent que les dispersions de la bande de valence (BV) la plus large et de la bande de conduction (BC) sont comparables, ce qui démontre que, selon le modèle de la bande de conduction, l'électron et le trou favorisent tous les deux le transport et que le « Si DPBA » a la capacité d'être utilisé comme matériel de transfert de charge. La densité des états et les intégrales de transfert dans les voies principales montrent que la propriété de transfert de charge est déterminée par l'interaction CH···p entre l'arête et la face et que la contribution du groupe SiMe 2 est minime. Les mobilités de charge du trou et de l'électron sont respectivement de 0 461 et 0 116 cm 2 ·V -1 ·s -1 . Elles sont du même ordre de grandeur et la mobilité de l'électron est du même ordre de grandeur que celle des dérivés bisimides de l'acide pérylène-3,4 :9,10-tétracarboxylique (BIP), soit 0,34 cm 2 ·V -1 ·s -1 . Les deux modèles montrent que le « Si DPBA » a le potentiel pour être utilisé comme matériel de transfert de charge bipolaire.

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“…The minimum of CB is higher than that of Si DPBA, which is consistent with Ref. 41, in which the LUMO of anthracene is higher than that of Si DPBA, but their VB maxima are comparable.…”

Section: Band Structuresupporting

confidence: 89%

“…This is consistent with the analysis of frontier molecular orbitals (FMOs) carried out by the authors in Ref. 41, in which the SiMe 2 group contributes to HOMO, but does not contribute to LUMO.…”

Section: Density Of States (Dos)supporting

confidence: 81%

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)

et al. 2011

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“…For similar halogen effects on the arrangement of aromatic molecules, see: Moon et al (2004); Isobe et al (2009). For an example of synthetic utility of the title compound in organic materials, see: Nakanishi et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

1,8-Diiodoanthracene

et al. 2010

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The molecule of the title compound, C14H8I2, an intermediate in the synthesis of organic materials, is nearly planar, the maximum deviation from the mean plane being 0.032 (1) Å for the C atoms and 0.082 (2) Å for the I atoms. In the crystal structure, a sandwich–herringbone arrangement of molecules is observed, whereas a columnar π-stacking arrangement has been reported for the chlorinated congener 1,8-dichloroanthracene. Similar effects of halogen substituents on the modulation of packing arrangements are reported for halogenated aromatic compounds such as tetracenes and chrycenes.

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“…It is anticipated that such a strong interaction will facilitate the construction of planar and straight-backbone structures and further extend the conjugation length of the phenyl acetylene chromophores. As a result, the excitation bands of chromophores could be extended into the visible region [19,20]. In recent years, many organic materials containing an anthracene unit have been extensively studied and developed as blue-light-emitting materials in OLEDs because of their excellent photoluminescence (PL) and electroluminescence (EL) properties [21].…”

Section: Introductionmentioning

confidence: 99%

Green Phosphors Based on 9,10-bis((4-((3,7-dimethyloctyl)oxy) phenyl) ethynyl) Anthracene for LED

et al. 2019

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An anthracene aromatic unit was introduced into the phenylethynyl structure by a rigid acetylene linkage at the C-9 and C-10 positions via Sonogashira coupling reactions, resulting in a planar and straight-backbone molecule (9,10-bis((4-((3,7-dimethyloctyl)oxy) phenyl) ethynyl) anthracene) (BPEA). Thermogravimetric analysis demonstrated the good thermal stability of the BPEA. Photoluminescence analysis showed that a suitable expanded π-conjugation in the BPEA made its excitation band extend into the visible region, and an intense green emission was observed under blue-light excitation. A bright green light-emitting diode with an efficiency of 18.22 lm/w was fabricated by coating the organic phosphor onto a 460 nm-emitting InGaN chip. All the results indicate that BPEA is a useful green-emitting material which is efficiently excited by blue light, and therefore, that it could be applied in many fields without UV radiation.

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Disilanyl Double‐Pillared Bisanthracene: A Bipolar Carrier Transport Material for Organic Light‐Emitting Diode Devices

Cited by 54 publications

References 45 publications

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)

1,8-Diiodoanthracene

Green Phosphors Based on 9,10-bis((4-((3,7-dimethyloctyl)oxy) phenyl) ethynyl) Anthracene for LED

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Disilanyl Double‐Pillared Bisanthracene: A Bipolar Carrier Transport Material for Organic Light‐Emitting Diode Devices

Cited by 54 publications

References 45 publications

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (SiDPBA)

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (SiDPBA)

1,8-Diiodoanthracene

Green Phosphors Based on 9,10-bis((4-((3,7-dimethyloctyl)oxy) phenyl) ethynyl) Anthracene for LED

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Resources

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A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)

A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (^SiDPBA)