Abstract
In this work, we report for the first time the use of a nonconjugated semicrystalline polymer as a film-forming agent to control the crystallization and tune the charge transport of solution-processed, small-molecule organic semiconductors. When 6,13-bis (triisopropylsilylethynyl) pentacene (TIPS pentacene) was demonstrated as a representative material to blend with polyethylene oxide (PEO) polymer, it crystallized into uniformly-aligned needles with reduced random orientation, enhanced long-range order and elevated areal coverage. Specifically, an ultra-low misorientation angle of 7.9° ± 3.5° was obtained with 10% PEO additive, beneficial for charge transport in the TIPS pentacene/PEO hybrid film. Bottom-gate, top-contact organic thin film transistors (OTFTs) based on TIPS pentacene/PEO mixture were found to show a field-effect mobility up to 2.5 × 10−2 cm2/Vs. This work may be universally applied to other organic semiconductors to regulate their crystal formation, enhance film forming and improve device performance of OTFTs. It contributes to the utilization of flexible substrates for future-generation high-performance organic electronics.
Similar content being viewed by others
References
He ZR, Chen JH, Li DW (2019) Crystal alignment for high performance organic electronics devices. J Vac Sci Technol A 37:040801
Bi S, Li Y, He ZR, Ouyang ZL, Guo QL, Jiang CM (2019) Self-assembly diketopyrrolopyrrole-based materials and polymer blend with enhanced crystal alignment and property for organic field-effect transistors. Org Electron 65:96–99
He ZR, Asare-Yeboah K, Zhang Z, Bi S (2019) Self-assembly crystal microribbons with nucleation additive for high-performance organic thin film transistors. Jpn J Appl Phys 58:061009
Kwon J, Takeda Y, Shiwaku R, Tokito S, Cho K, Jung S (2019) Three-dimensional monolithic integration in flexible printed organic transistors. Nature Commun 10
He ZR, Zhang Z, Bi S (2019) Small-molecule additives for organic thin film transistors. J Mater Sci Mater Electron 30:20899–20913
Neo WT, Ye Q, Shi Z, Chua S-J, Xu J (2018) Control of morphology and performance of diketopyrrolopyrrole-based electrochromic polymers using solvent vapor annealing. J Polym Res 25:68
He ZR, Lopez N, Chi XL, Li DW (2015) Solution-based 5, 6, 11, 12-tetrachlorotetracene crystal growth for high-performance organic thin film transistors. Org Electron 22:191–196
Borchert JW, Peng BY, Letzkus F, Burghartz JN, Chan PKL, Zojer K, Ludwigs S, Klauk H (2019) Small contact resistance and high-frequency operation of flexible low-voltage inverted coplanar organic transistors. Nature Commun 10
Wang C, Wang TM, Wang QH (2019) Ultralow-dielectric, nanoporous poly(methyl silsesquioxanes) films templated by a self-assembled block copolymer upon solvent annealing. J Polym Res 26
Rajesh K, Crasta V, Kumar NBR, Shetty G, Rekha PD (2019) Structural, optical, mechanical and dielectric properties of titanium dioxide doped PVA/PVP nanocomposite. J Polym Res 26
Negru OI, Grigoras M (2019) Synthesis and properties of copolyarylenes containing indolo 3,2-b carbazole moieties in the backbone. J Polym Res 26
Momin MA, Hossain KS, Bhuiyan A (2019) Microstructural, compositional, topological and optical properties of plasma polymerized cyclohexane amorphous thin films. J Polym Res 26
Peng BY, Huang SY, Zhou ZW, Chan PKL (2017) Solution-processed monolayer organic crystals for high-performance field-effect transistors and ultrasensitive gas sensors. Adv Funct Mater 27:1700999
Bi S, Li Q, He ZR, Guo Q, Asare-Yeboah K, Liu Y, Jiang C (2019) Highly enhanced performance of integrated piezo photo-transistor with dual inverted OLED gate and nanowire array channel. Nano Energy 66:104101
He ZR, Shaik S, Bi S, Chen JH, Li DW (2015) Air-stable solution-processed n-channel organic thin film transistors with polymer-enhanced morphology. Appl Phys Lett 106:183301
Zhao YY, Fan XY, Feng JG, Wang XD, Wu YC, Su B, Jiang L (2018) Regulated dewetting for patterning organic single crystals with pure crystallographic orientation toward high performance field-effect transistors. Adv Funct Mater 28
Bi S, Li Q, Yan Y, Asare-Yeboah K, Ma T, Tang C, Ouyang Z, He ZR, Liu Y, Jiang C (2019) Layer-dependent anisotropic frictional behavior in two-dimensional monolayer hybrid perovskite/ITO layered heterojunctions, hys. Chem Chem Phys 21:2540–2546
Li H, He ZR, Ouyang Z, Palchoudhury S, Ingram CW, Harruna II, Li D (2020) Modifying electrical and magnetic properties of single-walled carbon nanotubes by decorating with Iron oxide nanoparticles. J Nanosci Nanotechnol 20:2611–2616
He ZR, Xiao K, Durant W, Hensley DK, Anthony JE, Hong KL, Kilbey SM, Chen JH, Li DW (2011) Enhanced performance consistency in nanoparticle/TIPS Pentacene-based organic thin film transistors. Adv Funct Mater 21:3617–3623
Bi S, He ZR, Chen JH, Li DW (2015) Solution-grown small-molecule organic semiconductor with enhanced crystal alignment and areal coverage for organic thin film transistors. AIP Adv 5:077170
Asare-Yeboah K, Frazier RM, Szulczewski G, Li D (2014) Temperature gradient approach to grow large, preferentially oriented 6,13-bis(triisopropylsilylethynyl) pentacene crystals for organic thin film transistors. J Vac Sci Technol B 32:052401
Chen JH, Tee CK, Shtein M, Martin DC, Anthony J (2009) Controlled solution deposition and systematic study of charge-transport anisotropy in single crystal and single-crystal textured TIPS pentacene thin films. Org Electron 10:696–703
Cho SY, Ko JM, Jung JY, Lee JY, Choi DH, Lee C (2012) High-performance organic thin film transistors based on inkjet-printed polymer/TIPS pentacene blends. Org Electron 13:1329–1339
He ZR, Zhang Z, Bi S (2019) Polyacrylate polymer assisted crystallization: improved charge transport and performance consistency for solution-processable small-molecule semiconductor based organic thin film transistors. J Sci Adv Mater Devices 4:467–472
Kim SH, Hwang HR, Kwon HJ, Jang J (2012) Unipolar depletion-load organic circuits on flexible substrate by self-organized polymer blending with 6, 13-bis(triisopropylsilylethynyl)pentacene using ink-jet printing. Appl Phys Lett 100:4
He ZR, Chen JH, Li DW (2019) Polymer additive controlled morphology for high performance organic thin film transistors. Soft Matter 15:5790–5803
Bi S, Ouyang Z, Guo Q, Jiang C (2018) Additive effect for organic solar cell fabrication by multi-layer inking and stamping. J Sci Adv Mater Devices 3:221–225
He ZR, Zhang Z, Asare-Yeboah K, Bi S (2019) Poly(α-methylstyrene) polymer and small-molecule semiconductor blend with reduced crystal misorientation for organic thin film transistors. J Mater Sci Mater Electron 30:14335–14343
Hirao A, Matsuo Y, Goseki R (2019) Synthesis of novel block polymers with unusual block sequences by methodology combining living anionic polymerization and designed linking chemistry. J Polym Res 26
Ayat M, Rahmouni A, Belbachir M, Bensaada N, Baghdadli MC, Meghabar R (2019) Thermoplastic block copolymer: alpha-MethylStyrene and vinyl acetate catalyzed by clay layered called Maghnite-Na+ (Algerian MMT). J Polym Res 26
Park JH, Lee YT, Lee HS, Lee JY, Lee K, Lee GB, Han J, Kim TW, Im S (2013) Origin of bias-stress induced instability in organic thin-film transistors with semiconducting small-molecule/insulating polymer Blend Channel. ACS Appl Mater Interfaces 5:1625–1629
Li ZJ, Stoffel M, Ding LY, Rouxel D, Ding QJ (2019) Synthesis of hydrophilic P (VDF-TrFE) chloride sensitive polymer films for fluorescence sensing. J Polym Res 26
James DT, Kjellander BKC, Smaal WTT, Gelinck GH, Combe C, McCulloch I, Wilson R, Burroughes JH, Bradley DDC, Kim JS (2011) Thin-film morphology of inkjet-printed single-droplet organic transistors using polarized Raman spectroscopy: effect of blending TIPS-Pentacene with insulating polymer. ACS Nano 5:9824–9835
Cho SY, Ko JM, Lim J, Lee JY, Lee C (2013) Inkjet-printed organic thin film transistors based on TIPS pentacene with insulating polymers. J Mater Chem C 1:914–923
Ohe T, Kuribayashi M, Yasuda R, Tsuboi A, Nomoto K, Satori K, Itabashi M, Kasahara J (2008) Solution-processed organic thin-film transistors with vertical nanophase separation. Appl Phys Lett 93:3
Kang J, Shin N, Jang DY, Prabhu VM, Yoon DY (2008) Structure and properties of small molecule-polymer blend semiconductors for organic thin film transistors. JACS 130:12273–12275
Asare-Yeboah K, Bi S, He ZR, Li DW (2016) Temperature gradient controlled crystal growth from TIPS pentacene-poly(alpha-methyl styrene) blends for improving performance of organic thin film transistors. Org Electron 32:195–199
Chen JH, Shao M, Xiao K, He ZR, Li DW, Lokitz BS, Hensley DK, Kilbey SM, Anthony JE, Keum JK, Rondinone AJ, Lee WY, Hong SY, Bao ZA (2013) Conjugated polymer-mediated polymorphism of a high performance, small-molecule organic semiconductor with tuned intermolecular interactions, enhanced long-range order, and charge transport. Chem Mater 25:4378–4386
Park M, Min Y, Lee YJ, Jeong U (2014) Growth of long Triisopropylsilylethynyl Pentacene (TIPS-PEN) Nanofibrils in a polymer thin film during spin-coating. Macromol Rapid Commun 35:655–660
He ZR, Zhang ZY, Bi S (2019) Long-range crystal alignment with polymer additive for organic thin film transistors. J Polym Res 26:173. https://doi.org/10.1007/s10965-019-1842-1
He ZR, Chen JH, Keum JK, Szulczewski G, Li DW (2014) Improving performance of TIPS pentacene-based organic thin film transistors with small-molecule additives. Org Electron 15:150–155
He ZR, Zhang Z, Bi S (2020) Nanoparticles for organic electronics applications. Mater Res Express 7:012004
He ZR, Zhang Z, Bi S (2019) Nanoscale alignment of semiconductor crystals for high-fidelity organic electronics applications. Appl Nanosci. https://doi.org/10.1007/s13204-019-01068-4
Chen JH, Subramanian S, Parkin SR, Siegler M, Gallup K, Haughn C, Martin DC, Anthony JE (2008) The influence of side chains on the structures and properties of functionalized pentacenes. J Mater Chem 18:1961–1969
Anthony JE, Brooks JS, Eaton DL, Parkin SR (2001) Functionalized pentacene: improved electronic properties from control of solid-state order. J Am Chem Soc 123:9482–9483
Park SK, Jackson TN, Anthony JE, Mourey DA (2007) High mobility solution processed 6,13-bis (triisopropyl-silylethynyl) pentacene organic thin film transistors. Appl Phys Lett 91:063514
He ZR, Li DW, Hensley DK, Rondinone AJ, Chen JH (2013) Switching phase separation mode by varying the hydrophobicity of polymer additives in solution-processed semiconducting small-molecule/polymer blends. Appl Phys Lett 103:113301
Zhong HL, Smith J, Rossbauer S, White AJP, Anthopoulos TD, Heeney M (2012) Air-stable and high-mobility n-channel organic transistors based on small-molecule/polymer semiconducting blends. Adv Mater 24:3205–3211
He ZR, Chen JH, Sun ZZ, Szulczewski G, Li DW (2012) Air-flow navigated crystal growth for TIPS pentacene-based organic thin-film transistors. Org Electron 13:1819–1826
Chen JH, Tee CK, Shtein M, Anthony J, Martin DC (2008) Grain-boundary-limited charge transport in solution-processed 6,13 bis (tri-isopropylsilylethynyl) pentacene thin film transistors. J Appl Phys 103:114513
Acknowledgements
Z. H. would like to acknowledge support provided from the University of Alabama. S. Bi would like to thank Science and Technology Project of Liaoning Province (20180540006). A part of this research was conducted at the Center for Nanophase Materials Sciences, Oak Ridge National Laboratory, which is a DOE Office of Science User Facility.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
He, Z., Zhang, Z., Bi, S. et al. Ultra-low misorientation angle in small-molecule semiconductor/polyethylene oxide blends for organic thin film transistors. J Polym Res 27, 75 (2020). https://doi.org/10.1007/s10965-020-02047-y
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-020-02047-y