Diethynyl Aryl Derivatives for P-Channel and N-Channel Organic Field-Effect Transistors
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1091-AA11-12
Diethynyl Aryl Derivatives for P-Channel and N-Channel Organic Field-Effect Transistors Takeshi Yasuda1,2, Kimiaki Kashiwagi3, Yoshitomi Morizawa3, and Tetsuo Tsutsui1 1 Institute for Material Chemistry and Engineering, Kyushu University, Kasuga koen 6-1, Kasuga, Fukuoka, 816-0943, Japan 2 JST, PRESTO, 5 Sanbancho, Chiyoda-ku, Tokyo, 102-0075, Japan 3 Research Center, Asahi Glass Co., Ltd., Yokohama, Kanagawa, 221-8755, Japan ABSTRACT Organic field-effect transistors (OFETs) consisted of vacuum-evaporated diethynyl aryl derivatives were prepared and the device characteristics were evaluated. The fabricated OFETs showed typical p-type characteristics for diethynyl naphthalene derivative with two end naphthyl groups. By optimizing the fabrication process, the device exhibited a high field-effect hole mobility up to 0.12 cm2V-1s-1 and a high on/off current ratio of 3.3×105. On the other hand, OFETs showed typical n-type characteristics for diethynyl aryl derivative with two end heptafluoronaphthyl groups. We have observed clear changes from p-channel to n-channel conductions in OFETs by chemically modifying diethynyl aryl derivatives. INTRODUCTION Much attention has been paid on the development of organic semiconductors for applications to organic field-effect transistors (OFETs) [1,2]. Recently some linear planar-shaped extended π-electron systems, which are composed of two or three aromatic groups such as naphthalene and anthracene connected together with carbon-carbon bonds (a simple C-C single bond or a transvinylene double bond), have been synthesized and reported to exhibit excellent performances in OFETs [3,4]. When a rigid and straight acetylenic triple bond is accepted as the linkage unit, two aromatic rings can lie on the same plain and be arranged on exactly a straight line [5,6]. This can be a big advantage for attaining compact planar rectangular shapes favorable for attaining good molecular packing in crystalline states. In this work, we designed a series of linear molecules, in which three aromatic rings are connected together with rigid acetylenic linkages [7,8]. The central core aromatic group is either benzene or naphthalene or anthracene, and two end aromatic groups are either naphthyl or pentafluorophenyl or heptafluoronaphthyl groups. We report herein the synthesis and characterization of those compounds. Furthermore these derivatives have been used as organic semiconductors for OFETs. EXPERIMENT We prepared seven kinds of diethynyl aryl derivatives, as shown in Fig. 1. These materials except BH-101 were synthesized according to the reported method [7]. For use as reference, BH-101 was purchased from Wako Pure Chemical Industries, Ltd. All compounds were purified twice by train sublimation before use. Here, we briefly describe the procedure of BH-202.
F
F
F
F
n
m F F
n
n
n=0: BH-101 n=1: BH-202
F n
F
F
m F
F
F
F
F
m=0, n=1: BF-102 m=1, n=1: BF-202 m=0, n=2: BF-103 m=1, n=2: BF-203 m=1, n=0: BF-201
Figure 1. Structures of diethynyl aryl derivatives.
Synthesis of 2,
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