Abstract
More and more studies have demonstrated the substantial impact of flexible side chains on the device performance of organic semiconductors. In this chapter, we present our research on isoindigo-based polymer FETs through careful analysis of the influences of side chains. Besides, donor symmetry and backbone curvature effects are also investigated.
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References
Wang C, Dong H, Hu W, Liu Y, Zhu D (2012) Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics. Chem Rev 112:2208–2267
Wang X-Y, Lin H-R, Lei T, Yang D-C, Zhuang F-D, Wang J-Y, Yuan S-C, Pei J (2013) Azaborine compounds for organic field-effect transistors: efficient synthesis, remarkable stability, and bn dipole interactions. Angew Chem Int Ed 52:3117–3120
Ding L, Ying H-Z, Zhou Y, Lei T, Pei J (2010) Polycyclic imide derivatives: synthesis and effective tuning of lowest unoccupied molecular orbital levels through molecular engineering. Org Lett 12:5522–5525
Biniek L, Fall S, Chochos CL, Anokhin DV, Ivanov DA, Leclerc N, Lévêque P, Heiser T (2010) Impact of the alkyl side chains on the optoelectronic properties of a series of photovoltaic low-band-gap copolymers. Macromolecules 43:9779–9786
Boese R, Weiss H-C, Bläser D (1999) The melting point alternation in the short-chain n-alkanes: single-crystal X-ray analyses of propane at 30 K and of n-butane to n-nonane at 90 K. Angew Chem Int Ed 38:988–992
Ding L, Li H-B, Lei T, Ying H-Z, Wang R-B, Zhou Y, Su Z-M, Pei J (2012) Alkylene-chain effect on microwire growth and crystal packing of π-moieties. Chem Mater 24:1944–1949
Mei J, Graham KR, Stalder R, Reynolds JR (2010) Synthesis of isoindigo-based oligothiophenes for molecular bulk heterojunction solar cells. Org Lett 12:660–663
McCulloch I, Heeney M, Bailey C, Genevicius K, MacDonald I, Shkunov M, Sparrowe D, Tierney S, Wagner R, Zhang W, Chabinyc ML, Kline RJ, McGehee MD, Toney MF (2006) Liquid-crystalline semiconducting polymers with high charge-carrier mobility. Nat Mater 5:328–333
Osaka I, Takimiya K, McCullough RD (2010) Benzobisthiazole-based semiconducting copolymers showing excellent environmental stability in high-humidity air. Adv Mater 22:4993–4997
Ito Y, Virkar AA, Mannsfeld S, Oh JH, Toney M, Locklin J, Bao Z (2009) Crystalline ultrasmooth self-assembled monolayers of alkylsilanes for organic field-effect transistors. J Am Chem Soc 131:9396–9404
Lei T, Cao Y, Zhou X, Peng Y, Bian J, Pei J (2012) Systematic investigation of isoindigo-based polymeric field-effect transistors: design strategy and impact of polymer symmetry and backbone curvature. Chem Mater 24:1762–1770
Höltje HD, Folkers G (2008) Molecular modeling: basic principles and applications. Wiley-VCH, New York
Kitchen DB, Decornez H, Furr JR, Bajorath J (2004) Docking and scoring in virtual screening for drug discovery: methods and applications. Nat Rev Drug Discov 3:935–949
Stalder R, Mei J, Subbiah J, Grand C, Estrada LA, So F, Reynolds JR (2011) N-type conjugated polyisoindigos. Macromolecules 44:6303–6310
Rieger R, Beckmann D, Mavrinskiy A, Kastler M, Müllen K (2010) Backbone curvature in polythiophenes. Chem Mater 22:5314–5318
Osaka I, Abe T, Shinamura S, Miyazaki E, Takimiya K (2010) High-mobility semiconducting naphthodithiophene copolymers. J Am Chem Soc 132:5000–5001
Sato M, Asami A, Maruyama G, Kosuge M, Nakayama J, Kumakura S, Fujihara T, Unoura K (2002) Synthesis and redox property of the binuclear Pt (II) complexes bridged by thieno[3,2-b]thiophenes. J Organomet Chem 654:56–65
Li J, Bao Q, Li CM, Zhang W, Gong C, Chan-Park MB, Qin J, Ong BS (2010) Organic thin-film transistors processed from relatively nontoxic, environmentally friendlier solvents. Chem Mater 22:5747–5753
Rieger R, Beckmann D, Pisula W, Steffen W, Kastler M, Müllen K (2010) Rational optimization of benzo[2,1-b;3,4-b′]dithiophene-containing polymers for organic field-effect transistors. Adv Mater 22:83–86
Majewski LA, Kingsley JW, Balocco C, Song AM (2006) Influence of processing conditions on the stability of poly (3-hexylthiophene)-based field-effect transistors. Appl Phys Lett 88:222108
Chang J-F, Clark J, Zhao N, Sirringhaus H, Breiby DW, Andreasen JW, Nielsen MM, Giles M, Heeney M, McCulloch I (2006) Molecular-weight dependence of interchain polaron delocalization and exciton bandwidth in high-mobility conjugated polymers. Phys Rev B 74:115318
Chai J-D, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys 10:6615–6620
Anthony JE (2008) The larger acenes: versatile organic semiconductors. Angew Chem Int Ed 47:452–483
Takimiya K, Shinamura S, Osaka I, Miyazaki E (2011) Thienoacene-based organic semiconductors. Adv Mater 23:4347–4370
He M, Li J, Tandia A, Sorensen M, Zhang F, Fong HH, Pozdin VA, Smilgies D-M, Malliaras GG (2010) Importance of C 2 symmetry for the device performance of a newly synthesized family of fused-ring thiophenes. Chem Mater 22:2770–2779
Osaka I, Abe T, Shinamura S, Takimiya K (2011) Impact of isomeric structures on transistor performances in naphthodithiophene semiconducting polymers. J Am Chem Soc 133:6852–6860
Li Y, Singh SP, Sonar P (2010) A high mobility p-type DPP-thieno[3,2-b]thiophene copolymer for organic thin-film transistors. Adv Mater 22:4862–4866
Li Y, Sonar P, Singh SP, Soh MS, van Meurs M, Tan J (2011) Annealing-free high-mobility diketopyrrolopyrrole–quaterthiophene copolymer for solution-processed organic thin film transistors. J Am Chem Soc 133:2198–2204
Ha JS, Kim KH, Choi DH (2011) 2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-based donor–acceptor alternating copolymer bearing 5,5′-di(thiophen-2-yl)-2,2′-biselenophene exhibiting 1.5 cm2 V−1 s−1 hole mobility in thin-film transistors. J Am Chem Soc 133:10364–10367
Yan H, Chen Z, Zheng Y, Newman C, Quinn JR, Dotz F, Kastler M, Facchetti A (2009) A high-mobility electron-transporting polymer for printed transistors. Nature 457:679–686
Bijleveld JC, Zoombelt AP, Mathijssen SGJ, Wienk MM, Turbiez M, de Leeuw DM, Janssen RAJ (2009) Poly(diketopyrrolopyrrole–terthiophene) for ambipolar logic and photovoltaics. J Am Chem Soc 131:16616–16617
Sonar P, Singh SP, Li Y, Soh MS, Dodabalapur A (2010) A low-bandgap diketopyrrolopyrrole-benzothiadiazole-based copolymer for high-mobility ambipolar organic thin-film transistors. Adv Mater 22:5409–5413
Bronstein H, Chen Z, Ashraf RS, Zhang W, Du J, Durrant JR, Shakya Tuladhar P, Song K, Watkins SE, Geerts Y, Wienk MM, Janssen RAJ, Anthopoulos T, Sirringhaus H, Heeney M, McCulloch I (2011) Thieno[3,2-b]thiophene–diketopyrrolopyrrole-containing polymers for high-performance organic field-effect transistors and organic photovoltaic devices. J Am Chem Soc 133:3272–3275
Bürgi L, Turbiez M, Pfeiffer R, Bienewald F, Kirner H-J, Winnewisser C (2008) High-mobility ambipolar near-infrared light-emitting polymer field-effect transistors. Adv Mater 20:2217–2224
Mei J, Kim DH, Ayzner AL, Toney MF, Bao Z (2011) Siloxane-terminated solubilizing side chains: bringing conjugated polymer backbones closer and boosting hole mobilities in thin-film transistors. J Am Chem Soc 133:20130–20133
Lei T, Dou J-H, Pei J (2012) Influence of alkyl chain branching positions on the hole mobilities of polymer thin-film transistors. Adv Mater 24:6457–6461
Coropceanu V, Cornil J, da Silva Filho DA, Olivier Y, Silbey R, Brédas J-L (2007) Charge transport in organic semiconductors. Chem Rev 107:926–952
Tsao HN, Cho DM, Park I, Hansen MR, Mavrinskiy A, Yoon DY, Graf R, Pisula W, Spiess HW, Müllen K (2011) Ultrahigh mobility in polymer field-effect transistors by design. J Am Chem Soc 133:2605–2612
Chen H, Guo Y, Yu G, Zhao Y, Zhang J, Gao D, Liu H, Liu Y (2012) Highly π-extended copolymers with diketopyrrolopyrrole moieties for high-performance field-effect transistors. Adv Mater 24:4618–4622
Niedzialek D, Lemaur V, Dudenko D, Shu J, Hansen MR, Andreasen JW, Pisula W, Müllen K, Cornil J, Beljonne D (2013) Probing the relation between charge transport and supramolecular organization down to ångström resolution in a benzothiadiazole-cyclopentadithiophene copolymer. Adv Mater 25:1939–1947
Letizia JA, Salata MR, Tribout CM, Facchetti A, Ratner MA, Marks TJ (2008) N-channel polymers by design: optimizing the interplay of solubilizing substituents, crystal packing, and field-effect transistor characteristics in polymeric bithiophene-imide semiconductors. J Am Chem Soc 130:9679–9694
van Pham C, Burkhardt A, Shabana R, Cunningham DD, Mark HB, Zimmer H (1989) A convenient synthesis of 2,5-thienylene oligomers: some of their spectroscopic and electrochemical properties. Phosphorus Sulfur Silicon Relat Elem 46:153–168
Sotgiu G, Zambianchi M, Barbarella G, Botta C (2002) Synthesis and optical properties of soluble sexithiophenes with one central head-to-head junction. Tetrahedron 58:2245–2251
Li Y, Li Z, Wang C, Li H, Lu H, Xu B, Tian W (2010) Novel low-bandgap oligothiophene-based donor-acceptor alternating conjugated copolymers: synthesis, properties, and photovoltaic applications. J Polym Sci Part A: Polym Chem 48:2765–2776
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Lei, T. (2015). Side Chain Effects and Design of Isoindigo-Based Polymers. In: Design, Synthesis, and Structure-Property Relationship Study of Polymer Field-Effect Transistors. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45667-5_2
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DOI: https://doi.org/10.1007/978-3-662-45667-5_2
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