第 26 回万有仙台シンポジウム Poster 発表要旨有機発光デバイスのための大環状炭化水素分子 Hydrocarbon macrocycles for organic-light emitting devices Jing Xue,a Tomoo Izumi,b,c Asami Yoshii,a Koki Ikemoto,b Hideo Taka,b,c Sota Sato,a,b Hiroshi Kita,c and Hiroyuki Isobea,b (a Graduate School of Science, Tohoku University; b JST, ERATO, Isobe Degenerate c π-Integration Project, WPI-AIMR, Tohoku University; Konica Minolta, Inc) Polycyclic aromatic hydrocarbons with mobile π-electrons on rigid structures are attractive in organic electronics. We recently introduced a conjugated macrocycle containing only hydrocarbons, [n]cyclo-2,7-naphthylene ([n]CNAP)1, and revealed its features like easy synthesis, bipolar carrier transport nature and high thermal stability. Considering the notable molecular structure of [n]CNAP, we became interested in a similar meta-linked phenylene macrocycle, [n]cyclo-meta-phenylene ([n]CMP)2. The compound was first synthesized3 by Staab in 1964, but the original synthesis suffered from the low yields. Here, we achieved the gram preparation of major [n]CMP congeners (n = 5, 6) utilizing a concise one-pot method through Ni-promoted homocoupling. Structural features of [n]CMP in the solid state were revealed by X-ray diffraction and the Hirshfeld surface analyses, showing unique nanoporous structures in larger congeners to allow the encapsulation of small molecules. The sp2-carbon walls of phenylenes in the macrocycle might lead us to understand the characteristics of p-rich carbonaceous pores. The hydrocarbon macrocycles, [n]CMP, functioned as bipolar charge carrier transporting materials in OLED devices and revealed a higher performance for external quantum efficiency than the previous devices fabricated with [n]CNAP. ＜参考文献＞ 1）Nakanishi, W. et al. Angew. Chem. Int. Ed. 2011, 50, 5323; 2）Xue, J. Y.et al. J. Org. Chem. 2014, 79, 9735-9739; 3）Staab, H. A. et al. Tetrahedron Lett., 1964, 5, 319; Staab, H. A. et al. Chem. Ber., 1967, 100, 293. 発表者紹介氏名 XUE Jing（シュエジン）所属東北大学大学院理学研究科化学専攻学年博士課程後期 3 年研究室有機化学第二研究室