Non-substituted fused bis-tetracene based thin-film transistor with self-assembled monolayer hybrid dielectrics

Abstract

Polycyclic aromatic hydrocarbons with zigzag peripheries are high perspective candidates for organic electronics. However, large fused acenes are still poorly studied due to the tedious synthesis. Herein we report a non-substituted fused bistetracene DBATT (2.3,8.9-dibenzanthanthrene) as the semiconductor on low-voltage-driven organic thin-film transistors. The systematic studies of thin-film growth on various self-assembled monolayer (SAM) modified gate dielectrics and the electrical performances were carried out. The sub-monolayer of the semiconductor film shows larger island domains on the alkyl chain SAM. This device exhibits the hole mobility of 0.011 cm²·V⁻¹·s⁻¹ with a current ratio of I_on/I_off above 10⁵.

Keywords

fused bis-tetracene / organic field-effect transistor / contact resistance / self-assembled monolayer

References

[1] Tang M L, Reichardt A D, Okamoto T, . Functionalized asymmetric linear acenes for high-performance organic semiconductors. Advanced Functional Materials, 2008, 18(10): 1579–1585

[2] Klauk H, Halik M, Zschieschang U, . High-mobility polymer gate dielectric pentacene thin film transistors. Journal of Applied Physics, 2002, 92(9): 5259–5263

[3] Cicoira F, Santato C, Dinelli F, . Morphology and field-effect-transistor mobility in tetracene thin films. Advanced Functional Materials, 2005, 15(3): 375–380

[4] Anthony J E. Functionalized acenes and heteroacenes for organic electronics. Chemical Reviews, 2006, 106(12): 5028–5048

[5] Watanabe M, Chang Y J, Liu S W, . The synthesis, crystal structure and charge-transport properties of hexacene. Nature Chemistry, 2012, 4(7): 574–578

[6] Pannemann C, Diekmann T, Hilleringmann U. Degradation of organic field-effect transistors made of pentacene. Journal of Materials Research, 2004, 19(7): 1999–2002

[7] Baeg K J, Caironi M, Noh Y Y. Toward printed integrated circuits based on unipolar or ambipolar polymer semiconductors. Advanced Materials, 2013, 25(31): 4210–4244

[8] Zhang L, Fonari A, Liu Y, . Bistetracene: an air-stable, high-mobility organic semiconductor with extended conjugation. Journal of the American Chemical Society, 2014, 136(26): 9248–9251

[9] Sbargoud K, Mamada M, Jousselin-Oba T, . Low bandgap bistetracene-based organic semiconductors exhibiting air stability, high aromaticity and mobility. Chemistry, 2017, 23(21): 5076–5080

[10] Zhang L, Cao Y, Colella N S, . Unconventional, chemically stable, and soluble two-dimensional angular polycyclic aromatic hydrocarbons: from molecular design to device applications. Accounts of Chemical Research, 2015, 48(3): 500–509

[11] Wang Z, Li J, Zhang . Stable 2D bisthienoacenes: Synthesis, crystal packing, and photophysical properties. Chemistry, 2018, 24(54): 14442–14447

[12] Clar E. Research on the fine structure of anthanthrene and its benzologues according to the anellation procedure. Berichte der Deutschen Chemischen Gesellschaft, 1943, 76: 328–333

[13] Wang Z, Li R, Chen Y, . A novel angularly fused bistetracene: facile synthesis, crystal packing and single-crystal field effect transistors. Journal of Materials Chemistry C: Materials for Optical and Electronic Devices, 2017, 5(6): 1308–1312

[14] Lungerich D, Papaianina O, Feofanov M, . Dehydrative π-extension to nanographenes with zig–zag edges. Nature Communications, 2018, 9(1): 4756

[15] Lenz T, Schmaltz T, Novak M, . Self-assembled monolayer exchange reactions as a tool for channel interface engineering in low-voltage organic thin-film transistors. Langmuir, 2012, 28(39): 13900–13904

[16] Kwok D Y,Neumann A W.Contact angle measurement and contact angle interpretation. Advances in Colloid and Interface Science, 1999, 81(3): 167–249

[17] Virkar A A, Mannsfeld S, Bao Z, . Organic semiconductor growth and morphology considerations for organic thin-film transistors. Advanced Materials, 2010, 22(34): 3857–3875

[18] Wünsche J, Tarabella G, Bertolazzi S, . The correlation between gate dielectric, film growth, and charge transport in organic thin film transistors: the case of vacuum-sublimed tetracene thin films. Journal of Materials Chemistry C: Materials for Optical and Electronic Devices, 2013, 1(5): 967–976

[19] Akkerman H B, Mannsfeld S C B, Kaushik A P, . Effects of odd-even side chain length of alkyl-substituted diphenylbithiophenes on first monolayer thin film packing structure. Journal of the American Chemical Society, 2013, 135(30): 11006–11014

[20] Yoon M H, Kim C, Facchetti A, . Gate dielectric chemical structure-organic field-effect transistor performance correlations for electron, hole, and ambipolar organic semiconductors. Journal of the American Chemical Society, 2006, 128(39): 12851–12869

[21] Halik M, Klauk H, Zschieschang U, . Low-voltage organic transistors with an amorphous molecular gate dielectric. Nature, 2004, 431(7011): 963–966

[22] Yokota T, Kajitani T, Shidachi R, . A few-layer molecular film on polymer substrates to enhance the performance of organic devices. Nature Nanotechnology, 2018, 13(2): 139–144

[23] Liu D, He Z, Su Y, . Self-assembled monolayers of cyclohexyl-terminated phosphonic acids as a general dielectric surface for high-performance organic thin-film transistors. Advanced Materials, 2014, 26(42): 7190–7196

[24] Lee H S, Kim D H, Cho J H, . Effect of the phase states of self-assembled monolayers on pentacene growth and thin-film transistor characteristics. Journal of the American Chemical Society, 2008, 130(32): 10556–10564

[25] Ji D, Li T, Zou Y, . Copolymer dielectrics with balanced chain-packing density and surface polarity for high-performance flexible organic electronics. Nature Communications, 2018, 9: 2339

[26] Sinha S, Wang C H, Mukherjee M. Rubrene on differently treated SiO₂/Si substrates: A comparative study by atomic force microscopy, X-ray absorption and photoemission spectroscopies techniques. Thin Solid Films, 2017, 638: 167–172

[27] Sbargoud K, Mamada M, Jousselin-Oba T, . Low bandgap bistetracene-based organic semiconductors exhibiting air stability, high aromaticity and mobility. Chemistry, 2017, 23(21): 5076–5080

[28] Takimiya K, Yamamoto T, Ebata H, . Design strategy for air-stable organic semiconductors applicable to high-performance field-effect transistors. Science and Technology of Advanced Materials, 2007, 8(4): 273–276

[29] Maliakal A, Raghavachari K, Katz H, . Photochemical stability of pentacene and a substituted pentacene in solution and in thin films. Chemistry of Materials, 2004, 16(24): 4980–4986

[30] Klauk H, Schmid G, Radlik W, . Contact resistance in organic thin film transistors. Solid-State Electronics, 2003, 47(2): 297–301

[31] Kraft U, Sejfić M, Kang M J, . Flexible low-voltage organic complementary circuits: finding the optimum combination of semiconductors and monolayer gate dielectrics. Advanced Materials, 2015, 27(2): 207–214

RIGHTS & PERMISSIONS

Higher Education Press