[<I>n</I>]Cyclo-2,7-naphthylenes: Synthesis and Isolation of Macrocyclic Aromatic Hydrocarbons having Bipolar Carrier Transport Ability

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Bibliographic Information

Other Title
  • [<I>n</I>]シクロ-2,7-ナフチレン：合成と有機ELキャリア輸送層への応用

Abstract

Acenes that are larger than anthracene have been attractive and used as organic semiconductors. On the other hand, the smaller acenes such as naphthalene have been relatively unexplored. Herein, we report concise synthesis of [n]cyclo-2,7-naphthylenes ([n]CNAP), and their performance as bipolar carrier transport materials in organic light-emitting diode (OLED) devices.<BR> A series of [n]CNAP was synthesized by a nickel promoted coupling reaction of 2,7-dibromonaphthalene, and three major congeners (n = 5, 6, and 7) were isolated in 1, 24, and 12% yield, respectively. The reaction was readily scalable and isolation of abundant [6]-, and [7]CNAP was successfully achieved without recourse to chromatographic methods, which allowed the gram-scale preparation of [6]CNAP. The structures of all the isolated CNAP were established by single-crystal X-ray analysis. Thermogravimetric analysis showed the highly resistant characters of CNAP. The carrier transport performance of [6]- and [7]CNAP was evaluated in phosphorescent OLED devices. The performance as a hole and electron transport ability was comparable or higher than that of standard materials, a-NPD and Alq3.

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Details 詳細情報について

  • CRID
    1390282680531335680
  • NII Article ID
    130004645748
  • DOI
    10.11494/kisoyuki.2011.0.242.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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