Synthesis and characterization of solution-processable core-1,2,4-triazoline-3,5-diones derivatives as organic semiconductors

Guhyun Kwon; Jaeuk Han; Choongik Kim; SungYong Seo

Journal of Industrial and Engineering Chemistry, Vol.21, 178-181, January, 2015

DOI10.1016/j.jiec.2014.07.033 Export Citation

Synthesis and characterization of solution-processable core-1,2,4-triazoline-3,5-diones derivatives as organic semiconductors

Guhyun Kwon, Jaeuk Han, Choongik Kim^†, and SungYong Seo^{1, †}

Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 121-742, South Korea
¹Department of Chemistry, Pukyong National University, Busan 608-737, South Korea

E-mail:,

Organic semiconductors have drawn significant interest over the last two decades as essential components of various flexible electronic devices such as flexible displays, printable RFID tags, and sensors. To enhance the electrical properties of organic semiconductors, the design, synthesis, and characterization of new organic semiconductors has been of great interest. 1,2,4-Triazoline-3,5-dione derivatives are known to have various biological activities. The core structure of phenyl triazolopyridazine derivatives seems to be promising as potential organic semiconductors. To validate this possibility, two new compounds are synthesized and characterized using DSC, TGA, UV-vis, CV, XRD, and AFM. Organic TFT performance was showing but low.

Keywords:1,2,4-Triazoline-3,5-dione;Organic semiconductor;Thin film transistor

[References]

Kim C, Facchetti A, Marks TJ, Science, 318, 76 (2007)
Usta H, Kim C, Wang Z, Lu S, Huang H, Facchetti A, Marks TJ, J. Mater. Chem., 22, 4459 (2012)
Klauk H, Halik M, Zschieschang U, Eder F, Schmid G, Dehm C, Appl. Phys. Lett., 82, 4175 (2003)
Tan L, Zhang L, Jiang X, Yang XD, Wang LJ, Wang Z, Li LQ, Hu WP, Shuai ZG, Li L, Zhu DB, Adv. Funct. Mater., 19(2), 272 (2009)
Simlot R, Izydore RA, Wong OT, Hall IH, J. Pharm. Sci., 83, 367 (1994)
Martinez A, Alonso M, Castro A, Dorronsoro I, Gelpi JL, Luque FJ, Perez C, Moreno FJ, J. Med. Chem., 48, 7103 (2005)
Hall IH, Wong OT, Simlot S, Miller III MV, Izydo RA, Anticancer Res., 12, 1355 (1992)
Mitchell CL, Keasling HH, Gross EG, J. Am. Pharm. Assoc., 48, 122 (1959)
Cookson RC, Gupte SS, Stevens IDR, Watts CT, Organ. Synth., 51, 121 (1971)
Adam W, Carballeira N, J. Am. Chem. Soc., 106, 2874 (1984)
Adam A, De Lucchi O, Angew. Chem. Int. Ed., 110, 1638 (1980)
Moriarity RM, Prakash I, Penmasta R, Synth. Commun., 17, 409 (1987)

[1] Kim C, Facchetti A, Marks TJ, Science, 318, 76 (2007)

[2] Usta H, Kim C, Wang Z, Lu S, Huang H, Facchetti A, Marks TJ, J. Mater. Chem., 22, 4459 (2012)

[3] Klauk H, Halik M, Zschieschang U, Eder F, Schmid G, Dehm C, Appl. Phys. Lett., 82, 4175 (2003)

[4] Tan L, Zhang L, Jiang X, Yang XD, Wang LJ, Wang Z, Li LQ, Hu WP, Shuai ZG, Li L, Zhu DB, Adv. Funct. Mater., 19(2), 272 (2009)

[5] Simlot R, Izydore RA, Wong OT, Hall IH, J. Pharm. Sci., 83, 367 (1994)

[6] Martinez A, Alonso M, Castro A, Dorronsoro I, Gelpi JL, Luque FJ, Perez C, Moreno FJ, J. Med. Chem., 48, 7103 (2005)

[7] Hall IH, Wong OT, Simlot S, Miller III MV, Izydo RA, Anticancer Res., 12, 1355 (1992)

[8] Mitchell CL, Keasling HH, Gross EG, J. Am. Pharm. Assoc., 48, 122 (1959)

[9] Cookson RC, Gupte SS, Stevens IDR, Watts CT, Organ. Synth., 51, 121 (1971)

[10] Adam W, Carballeira N, J. Am. Chem. Soc., 106, 2874 (1984)

[11] Adam A, De Lucchi O, Angew. Chem. Int. Ed., 110, 1638 (1980)

[12] Moriarity RM, Prakash I, Penmasta R, Synth. Commun., 17, 409 (1987)