[20p-B104-1~20] 12.4 Organic light-emitting devices and organic transistors

[20p-B104-7] Intramolecular Proton Transfer and Charge Transport in Organic Semiconductors

Kyohei Nakano¹, Iat Wai Leong², Yusuke Nishiyama^3,4, Yutaro Ogaeri^3,4, Toshio Yamazaki⁵, Daisuke Hashizume¹, 〇Keisuke Tajima¹ (1.RIKEN CEMS, 2.SANKEN Osaka Univ., 3.RIKEN-JEOL, 4.JEOL RESONANCE, 5.RIKEN BDR)

Keywords:organic semiconductor, proton transfer, tautomer

We have newly synthesized a group of derivatives of 2,2’-bi-1H-indene-3,3’-dihydroxy-1,1’-dione (BIT) as organic semiconductor molecules having a π-conjugated structure planarized by intramolecular hydrogen bonding and capable of intramolecular proton transfer between the tautomers. The C₁₆-BIT with a long alkyl group on one side can induce a lamellar structure suitable for charge transport in thin films, and a relatively good hole mobility of 0.01 cm²/Vs was observed in OFETs. In another BIT derivative, solid-state NMR and other measurements suggest that fast intramolecular proton transfer is also occurring in the solid state.