Donor-acceptor alternating π-conjugated polymers containing Di(thiophen-2-yl)pyrene and 2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H, 5H)-dione for organic thin-film transistors

New diketopyrrolopyrrole (DPP)-containing conjugated polymers such as poly(2,5-bis(2-octyldodecyl)-3-(5-(pyren-1-yl)thiophen-2-yl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (P(DTDPP-alt-(1,6)PY)) and poly(2,5-bis(2-octyldodecyl)-3-(5-(pyren-2-yl)thiophen-2-yl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (P(DTDPP-alt-(2,7)PY)) were successfully synthesized via Suzuki coupling reactions under Pd(0)-catalyzed conditions. P(DTDPP-alt-(2,7)PY), incorporating 2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DTDPP) at the 2,7-position of a pyrene ring showed a lower band-gap energy (E. = 1.65 eV) than the 1,6-substituted analog, P(DTDPP-alt-(1,6)PY) (E = 1.71 eV). The energies of the molecular frontier orbitals of the substituted polymers were successfully tuned by changing the anchoring position of DTDPP from the 1,6- to the 2,7-position of the pyrene ring. An organic thin-film transistor fabricated using the newly synthesized P(DTDPP-alt-(2,7)PY), as a semiconductor material exhibited a maximum mobility of up to 0.23 cm2 V−1 s−1 (Ion/off ∼ 106), which was much larger than that obtained using P(DTDPP-alt-(1,6)PY). This distinction is attributed to morphological differences in the solid state arising from differences between the geometrical configurations of DTDPP and the pyrene ring. In addition, the organic phototransistor devices made of P(DTDPP-alt-(2,7)PY) showed interesting photoinduced enhancement of drain current when irradiating the excitation light whose intensity is very small. Based on the photoinduced effect on IDS, photocontrolled memory could be realized under the variation of gate voltages. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

[1]  Maxim Shkunov,et al.  Liquid-crystalline semiconducting polymers with high charge-carrier mobility , 2006, Nature materials.

[2]  D. Seferos,et al.  Atomistic band gap engineering in donor-acceptor polymers. , 2012, Journal of the American Chemical Society.

[3]  Oana D. Jurchescu,et al.  Effect of impurities on the mobility of single crystal pentacene , 2004, cond-mat/0404130.

[4]  John E. Anthony,et al.  High mobility solution processed 6,13-bis(triisopropyl-silylethynyl) pentacene organic thin film transistors , 2007 .

[5]  Prashant Sonar,et al.  A High Mobility P‐Type DPP‐Thieno[3,2‐b]thiophene Copolymer for Organic Thin‐Film Transistors , 2010, Advanced materials.

[6]  S. Jenekhe,et al.  New Ambipolar Organic Semiconductors. 2. Effects of Electron Acceptor Strength on Intramolecular Charge Transfer Photophysics, Highly Efficient Electroluminescence, and Field-Effect Charge Transport of Phenoxazine-Based Donor−Acceptor Materials , 2008 .

[7]  Bernard Kippelen,et al.  A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. , 2007, Journal of the American Chemical Society.

[8]  Youngmee Kim,et al.  Highly sensitive phototransistor with crystalline microribbons from new π-extended pyrene derivative via solution-phase self-assembly. , 2011, Chemical communications.

[9]  Ji-hoon Kim,et al.  Photovoltaic devices using semiconducting polymers containing head‐to‐tail‐structured bithiophene, pyrene, and benzothiadiazole derivatives , 2012 .

[10]  R. Stoltenberg,et al.  Ambipolar, high performance, acene-based organic thin film transistors. , 2008, Journal of the American Chemical Society.

[11]  John E. Anthony,et al.  Contact-induced crystallinity for high-performance soluble acene-based transistors and circuits. , 2008, Nature materials.

[12]  D. Kumaki,et al.  Surface-energy-dependent field-effect mobilities up to 1 cm2/V s for polymer thin-film transistor , 2009 .

[13]  Robert Graf,et al.  Ultrahigh mobility in polymer field-effect transistors by design. , 2011, Journal of the American Chemical Society.

[14]  Chen Li,et al.  Tuning the photoresponse in organic field-effect transistors. , 2012, Journal of the American Chemical Society.

[15]  P. Sonar,et al.  Annealing-free high-mobility diketopyrrolopyrrole-quaterthiophene copolymer for solution-processed organic thin film transistors. , 2011, Journal of the American Chemical Society.

[16]  Ute Zschieschang,et al.  High-mobility polymer gate dielectric pentacene thin film transistors , 2002 .

[17]  Albert J. J. M. van Breemen,et al.  High‐Performance Solution‐Processable Poly(p‐phenylene vinylene)s for Air‐Stable Organic Field‐Effect Transistors , 2005 .

[18]  Daoben Zhu,et al.  Novel butterfly pyrene-based organic semiconductors for field effect transistors. , 2006, Chemical communications.

[19]  Martin Baumgarten,et al.  Dithieno[2,3‐d;2′,3′‐d′]benzo[1,2‐b;4,5‐b′]dithiophene (DTBDT) as Semiconductor for High‐Performance, Solution‐Processed Organic Field‐Effect Transistors , 2009 .

[20]  Samson A. Jenekhe,et al.  New Conjugated Polymers with Donor−Acceptor Architectures: Synthesis and Photophysics of Carbazole−Quinoline and Phenothiazine−Quinoline Copolymers and Oligomers Exhibiting Large Intramolecular Charge Transfer , 2001 .

[21]  Gui Yu,et al.  Highly π‐Extended Copolymers with Diketopyrrolopyrrole Moieties for High‐Performance Field‐Effect Transistors , 2012, Advanced materials.

[22]  Liping Ding,et al.  Pyrene-Containing Conjugated Polymer-Based Fluorescent Films for Highly Sensitive and Selective Sensing of TNT in Aqueous Medium , 2011 .

[23]  A. Heeger,et al.  High performance weak donor-acceptor polymers in thin film transistors: effect of the acceptor on electronic properties, ambipolar conductivity, mobility, and thermal stability. , 2011, Journal of the American Chemical Society.

[24]  B. Ong,et al.  Thieno[3,2-b]thiophene oligomers and their applications as p-type organic semiconductors , 2009 .

[25]  Youngmee Kim,et al.  Highly Photosensitive J‐Aggregated Single‐Crystalline Organic Transistors , 2011, Advanced materials.

[26]  Deqing Zhang,et al.  1-Imino nitroxide pyrene for high performance organic field-effect transistors with low operating voltage. , 2006, Journal of the American Chemical Society.

[27]  Alberto Salleo,et al.  Indacenodithiophene semiconducting polymers for high-performance, air-stable transistors. , 2010, Journal of the American Chemical Society.

[28]  Xiao Hu,et al.  Synthesis and characterization of soluble conjugated polymers having pyrene moiety in the main chain , 2010 .

[29]  K. Müllen,et al.  Blue-Emitting Poly(2,7-pyrenylene)s: Synthesis and Optical Properties , 2008 .

[30]  N. Stingelin,et al.  Low band gap selenophene–diketopyrrolopyrrole polymers exhibiting high and balanced ambipolar performance in bottom-gate transistors , 2012 .

[31]  Zhenan Bao,et al.  Effect of Mesoscale Crystalline Structure on the Field‐Effect Mobility of Regioregular Poly(3‐hexyl thiophene) in Thin‐Film Transistors , 2005 .

[32]  K. Müllen,et al.  The Influence of Morphology on High‐Performance Polymer Field‐Effect Transistors , 2009 .

[33]  Koichi M. T. Yamada,et al.  Effect of Molecular Packing on Field-Effect Performance of Single Crystals of Thienyl-Substituted Pyrenes , 2008 .

[34]  J. Cho,et al.  Importance of Solubilizing Group and Backbone Planarity in Low Band Gap Polymers for High Performance Ambipolar field-effect Transistors , 2012 .

[35]  Daoben Zhu,et al.  High-Performance, Stable Organic Field-Effect Transistors Based on trans-1,2-(Dithieno[2,3-b:3′,2′-d]thiophene)ethene , 2009 .

[36]  R. Perutz,et al.  Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters. , 2005, Chemical communications.

[37]  Wen‐Chang Chen,et al.  Selenophene-DPP donor–acceptor conjugated polymer for high performance ambipolar field effect transistor and nonvolatile memory applications , 2012 .

[38]  Donghoon Choi,et al.  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. , 2011, Journal of the American Chemical Society.

[39]  Youngmee Kim,et al.  Unusually High‐Performing Organic Field‐Effect Transistors Based on π‐Extended Semiconducting Porphyrins , 2012, Advanced materials.

[40]  Aram Amassian,et al.  Tetrathienoacene copolymers as high mobility, soluble organic semiconductors. , 2008, Journal of the American Chemical Society.

[41]  H. Sirringhaus,et al.  Thieno[3,2-b]thiophene-diketopyrrolopyrrole-containing polymers for high-performance organic field-effect transistors and organic photovoltaic devices. , 2011, Journal of the American Chemical Society.