Synthesis and Characterization of Fluorenone-Based Donor-Acceptor Small Molecule Organic Semiconductors for Organic Field-Effect Transistors

Jeongyeon Lee; Chaeyoung Yun; M. Rajeshkumar Reddy; Dongil Ho; Choongik Kim; SungYong Seo

Macromolecular Research, Vol.28, No.7, 654-659, June, 2020

DOI10.1007/s13233-020-8123-z Export Citation

Synthesis and Characterization of Fluorenone-Based Donor-Acceptor Small Molecule Organic Semiconductors for Organic Field-Effect Transistors

Jeongyeon Lee, Chaeyoung Yun¹, M. Rajeshkumar Reddy¹, Dongil Ho, Choongik Kim^†, and SungYong Seo^{1, †}

Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 04107, Korea
¹Department of Chemistry, Pukyong National University, Busan 48547, Korea

E-mail:,

In this study, a series of new fluorenone-based small molecules were synthesized and characterized as organic semiconductors for organic field-effect transistors. Thermal, optical, and electrochemical properties of the new compounds were characterized. Furthermore, thin films of the developed compounds were employed as organic semiconductors, and vacuum-deposited film of fluorenone derivative with alkylated double thiophene exhibited p-channel device characteristics with hole mobility as high as 0.02 cm2/Vs and current on/off ratio of 107. In addition, surface morphology and microstructure of vacuum deposited films were analyzed and correlated with the electrical characteristics.

Keywords:organic field effect transistor;organic semiconductor;fluorenone;donor-acceptor

[References]

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Yamashita Y, Sci. Technol. Adv. Mat., 10, 024313 (2009)
Huang PY, Chen LH, Chen YY, Chang WJ, Wang JJ, Lii KH, Yan JY, Ho JC, Lee CC, Kim C, Chem. Eur., 19, 3721 (2013)
Geffroy B, Le Roy P, Prat C, Polym. Int., 55, 572 (2006)
Xu RP, Li YQ, Tang JX, J. Mater. Chem. C, 4, 9116 (2016)
Cheng P, Li G, Zhan X, Yang Y, Nat. Photonics, 12, 131 (2018)
Inganas O, Adv. Mater., 30, 180038 (2018)
Lin P, Yan F, Adv. Mater., 24(1), 34 (2012)
Torsi L, Magliulo M, Manoli K, Palazzo G, Chem. Soc. Rev., 42, 8612 (2013)
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Suraru SL, Zschieschang U, Klauk H, Wurthner F, Chem. Commun., 47, 1767 (2011)
Mullen K, Pisula W, J. Am. Chem. Soc., 137(30), 9503 (2015)
Ozdemir R, Choi D, Ozdemir M, Kwon G, Kim H, Sen U, Kim C, Usta H, J. Mater. Chem. C, 5, 2368 (2017)
Vegiraju S, He GY, Kim C, Priyanka P, Chiu YJ, Liu CW, Huang CY, Ni JS, Wu YW, Chen Z, Adv. Funct. Mater., 27, 160676 (2017)
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Gupta A, Ali A, Singh TB, Bilic A, Bach U, Evans RA, Tetrahedron, 68, 9440 (2012)
Kim FS, Guo XG, Watson MD, Jenekhe SA, Adv. Mater., 22(4), 478 (2010)
Kim J, Cho N, Ko HM, Kim C, Lee JK, Ko J, Sol. Energy Mater. Sol. Cells, 102, 159 (2012)
Chen MC, Chiang YJ, Kim C, Guo YJ, Chen SY, Liang YJ, Huang YW, Hu TS, Lee GH, Facchetti A, Chem. Commun., 1846 (2009).
Li C, Du X, Zhou Y, Ye J, Fu L, Humphrey MG, Wu C, Zhao J, Du Y, Tao S, J. Mater. Chem. C, 6, 6949 (2018)
Kim C, Facchetti A, Marks TJ, Adv. Mater., 19(18), 2561 (2007)
Borgne ML, Quinn J, Martin J, Stingelin N, Li Y, Wantz G, J. Mater. Chem. C, 5, 5143 (2017)
Pernstich KP, Haas S, Oberhoff D, Goldmann C, Gundlach DJ, Batlogg B, Rashid AN, Schitter GJ, Appl. Phys., 96, 6431 (2004)
Kim C, Facchetti A, Marks TJ, J. Am. Chem. Soc., 131(25), 9122 (2009)

[Referenced By]

[1] Zhang L, Di CA, Yu G, Liu Y, J. Mater. Chem., 20, 7059 (2010)

[2] Paterson AF, Singh S, Fallon KJ, Hodsden T, Han Y, Schroeder BC, Bronstein H, Heeney M, McCulloch I, Anthopoulos TD, Adv. Mater., 30, 180107 (2018)

[3] Yamashita Y, Sci. Technol. Adv. Mat., 10, 024313 (2009)

[4] Huang PY, Chen LH, Chen YY, Chang WJ, Wang JJ, Lii KH, Yan JY, Ho JC, Lee CC, Kim C, Chem. Eur., 19, 3721 (2013)

[5] Geffroy B, Le Roy P, Prat C, Polym. Int., 55, 572 (2006)

[6] Xu RP, Li YQ, Tang JX, J. Mater. Chem. C, 4, 9116 (2016)

[7] Cheng P, Li G, Zhan X, Yang Y, Nat. Photonics, 12, 131 (2018)

[8] Inganas O, Adv. Mater., 30, 180038 (2018)

[9] Lin P, Yan F, Adv. Mater., 24(1), 34 (2012)

[10] Torsi L, Magliulo M, Manoli K, Palazzo G, Chem. Soc. Rev., 42, 8612 (2013)

[11] Usta H, Facchetti A, in Large Area and Flexible Electronics, WileyVCH, Weinheim, pp.1 2015.

[12] Lin Y, Li Y, Zhan X, Chem. Soc. Rev., 41, 4245 (2012)

[13] Mei YC, Loth MA, Payne M, Zhang WM, Smith J, Day CS, Parkin SR, Heeney M, McCulloch I, Anthopoulos TD, Anthony JE, Jurchescu OD, Adv. Mater., 25(31), 4352 (2013)

[14] Anthony JE, Heeney M, Ong BS, MRS Bull., 33, 698 (2008)

[15] Suraru SL, Zschieschang U, Klauk H, Wurthner F, Chem. Commun., 47, 1767 (2011)

[16] Mullen K, Pisula W, J. Am. Chem. Soc., 137(30), 9503 (2015)

[17] Ozdemir R, Choi D, Ozdemir M, Kwon G, Kim H, Sen U, Kim C, Usta H, J. Mater. Chem. C, 5, 2368 (2017)

[18] Vegiraju S, He GY, Kim C, Priyanka P, Chiu YJ, Liu CW, Huang CY, Ni JS, Wu YW, Chen Z, Adv. Funct. Mater., 27, 160676 (2017)

[19] Bagui A, Datt R, Gupta V, Singh SP, Chem. Commun., 53, 12790 (2017)

[20] Lincker F, Heinrich B, De Bettignies R, Rannou P, Pecaut J, Grevin B, Pron A, Donnio B, Demadrille R, J. Mater. Chem., 21, 5238 (2011)

[21] Sonar P, Ha TJ, Dodabalapur A, Chem. Commun., 49, 1588 (2013)

[22] Lincker F, Attias AJ, Mathevet F, Heinrich B, Donnio B, Fave JL, Rannou P, Demadrille R, Chem. Commun., 48, 3209 (2012)

[23] Porzio W, Destri S, Giovanella U, Pasini M, Motta T, Natali D, Sampietro M, Campione M, Thin Solid Films, 492(1-2), 212 (2005)

[24] Cho K, Reddy MR, Kim D, Ho D, Yun C, Seo S, Kim C, Mol. Cryst. Liq. Cryst., 690(1), 56 (2019)

[25] Lim CJ, Lei Y, Wu B, Li L, Liu X, Lu Y, Zhu F, Ong BS, Hu X, Ng SC, Tetrahedron Lett., 57, 1430 (2016)

[26] Demadrille R, Delbosc N, Kervella Y, Firon M, De Bettignies R, Billon M, Rannou P, Pron A, J. Mater. Chem., 17, 4661 (2007)

[27] Qin C, Islam A, Han L, J. Mater. Chem., 22, 19236 (2012)

[28] Do TT, Rundel K, Gu Q, Gann E, Manzhos S, Feron K, Bell J, McNeill CR, Sonar P, New J. Chem., 41, 2899 (2017)

[29] Ozdemir M, Choi D, Kwon G, Zhrlu Y, Kim H, Kim MG, Seo S, Sen U, Citir M, Kim C, RSC Adv., 6, 212 (2016)

[30] Hu T, Han L, Xiao M, Bao X, Wang T, Sun M, Yang R, J. Mater. Chem. C, 2, 8047 (2014)

[31] Reddy MR, Kim H, Kim C, Seo S, Synth. Met., 235, 153 (2018)

[32] Junichi H, Hisashi O, Takayuki U, Hiroaki I, Tokyo Institute of Technology, JP Patent 2017066089 (2017).

[33] Lai LF, Qin C, Chui CH, Islam A, Han L, Ho CL, Wong WY, Dyes Pigment., 98, 428 (2013)

[34] Durso M, Zambianchi M, Zanelli A, LoBello MG, De Angelis F, Toffanin S, Cavallini S, Gentili D, Tinti F, Cavallini M, Tetrahedron, 70, 6222 (2014)

[35] Zhang S, Ocheje MU, Huang L, Galuska L, Cao Z, Luo S, Cheng YH, Ehlenberg D, Goodman RB, Zhou D, Adv. Electron. Mater., 5, 180089 (2019)

[36] Fu B, Baltazar J, Hu Z, Chien AT, Kumar S, Henderson CL, Collard DM, Reichmanis E, Chem. Mater., 24, 4123 (2012)

[37] Gibson GL, McCormick TM, Seferos DS, J. Am. Chem. Soc., 134(1), 539 (2012)

[38] Yassin A, Leriche P, Allain M, Roncali J, New J. Chem., 37, 502 (2013)

[39] Gupta A, Ali A, Singh TB, Bilic A, Bach U, Evans RA, Tetrahedron, 68, 9440 (2012)

[40] Kim FS, Guo XG, Watson MD, Jenekhe SA, Adv. Mater., 22(4), 478 (2010)

[41] Kim J, Cho N, Ko HM, Kim C, Lee JK, Ko J, Sol. Energy Mater. Sol. Cells, 102, 159 (2012)

[42] Chen MC, Chiang YJ, Kim C, Guo YJ, Chen SY, Liang YJ, Huang YW, Hu TS, Lee GH, Facchetti A, Chem. Commun., 1846 (2009).

[43] Li C, Du X, Zhou Y, Ye J, Fu L, Humphrey MG, Wu C, Zhao J, Du Y, Tao S, J. Mater. Chem. C, 6, 6949 (2018)

[44] Kim C, Facchetti A, Marks TJ, Adv. Mater., 19(18), 2561 (2007)

[45] Borgne ML, Quinn J, Martin J, Stingelin N, Li Y, Wantz G, J. Mater. Chem. C, 5, 5143 (2017)

[46] Pernstich KP, Haas S, Oberhoff D, Goldmann C, Gundlach DJ, Batlogg B, Rashid AN, Schitter GJ, Appl. Phys., 96, 6431 (2004)

[47] Kim C, Facchetti A, Marks TJ, J. Am. Chem. Soc., 131(25), 9122 (2009)