Synthesis and Characterization of Organic Semiconductors without Dopants

Hyun-Soo Yang; Haiil Ryu; Youn-Mook Lim

Journal of Industrial and Engineering Chemistry, Vol.3, No.1, 1-6, March, 1997

Hyun-Soo Yang , Haiil Ryu¹, and Youn-Mook Lim

Dept. Of Fine Chem. Eng. and Chemistry, ChungNam National Univ., 220 Goong-Dong, Taejeon, 305-764, Korea
¹Dept. of Chemistry Education, Kongju National Univ., 182 Shinkwan-Dong, Kongju-City, 314-701, Korea

Polymer-type organic semiconductors carrying [2,3-NcFeL]_n complexes have newly prepared here. The polymers (μ-1,4-diisocyanonaphthalene)-2,3-naphthalocyaninatoiron(Ⅱ), (μ-9,10-diisocyanoanthracene)-2,3-naphthalocyaninatoiron(Ⅱ), (μ-1,2-diisocyanoethaane)-2,3-naphthalocyaninatoiron(Ⅱ), (μ-1,6-diisocyanohexane)-2,3-naphthalocyaninatoiron(Ⅱ), and (μ-1,12-diisocyanododecene)-2,3-naphthalocyaninatoiron(Ⅱ) are synthesized and characterized by spectroscopic methods. These polymers showed excellent electrical conductivities without any dopant treatment. The electrical conductivities were mainly resulted from metal-ligand electron delocalization in the [2,3-NcFeL]_n complexes. The complexes have an enlarged macrocycle that the π-electron back donated ability of metal macrocycle is stronger than σ-electron coordinated ability of isonitrile ligand. In comparison with the (PcFeL)_n complexes which are a kind of organic semiconductor, the [2,3-NcFeL]_n. complexes consisting with strongly π-electron conjugated system along the axis showed much higher electrical conductivities even in the absence of dopant treatment.

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[Related Articles]

[1] Schneider O, Hanack M, Chem. Ber., 116, 2088 (1983)

[2] Koch J, Hanack M, Chem. Ber., 116, 2109 (1983)

[3] Schneider O, Metz J, Hanack M, Mol. Cryst. Liq. Cryst., 81, 273 (1982)

[4] Hanack M, Chimia., 37, 238 (1983)

[5] Metz J, Hanack M, J. Am. Chem. Soc., 105, 828 (1983)

[6] Datz A, Metz J, Schneider O, Hanack M, Synth. Met., 9, 31 (1984)

[7] Hanack M, Isral J. Chem., 25, 205 (1985)

[8] Hanack M, Munz X, Synth. Met., 10, 357 (1985)

[9] Kobel W, Hanack M, Inorg. Chem., 25, 103 (1986)

[10] Deger S, Hanack M, Synth. Met., 13, 319 (1986)

[11] Deger S, Hanack M, Isral J. Chem., 27, 347 (1986)

[12] Schultz H, Lehmann H, Rein M, Hanack M, Phthalocyaninatometal and Related Complexes with Special Electrical and Optical Properties, in: Structure and Bonding Bd. 74, Springer-Verlag, Heidelberg s.41 (1991)

[13] Hanack M, Ryu H, Synth. Met., 46, 113 (1992)

[14] Ryu H, Dessertatio, Tubingen Univ. (1992)

[15] Hanack M, Lange A, Rein M, Behnisch R, Renz G, Leverenz A, Synth. Met., 29, F1 (1989)

[16] Orti E, Piqeras MC, Crespo R, Bredas JL, Chem. Mater., 2, 110 (1990)

[17] Vail SL, Moran CM, Hoore HB, J. Org. Chem., 27, 2067 (1962)

[18] Freudenreich C, Biellmann JF, J. Am. Chem. Soc., 106, 3344 (1984)