Journal of Industrial and Engineering Chemistry, Vol.86, 150-157, June, 2020
Synthetic strategy for thienothiophene-benzotriazole-based polymers with high backbone planarity and solubility for field-effect transistor applications
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We report on a synthetic strategy for a series of thienothiophene-benzotriazole-based polymers.octyl- PTTBTz-F, Si-PTTBTz, and Si-PTTBTz-F.wherein conformational locks are introduced to induce intra- and intermolecular interactions (F…S, F…H-C, and C-F…πF) for high backbone planarity and siloxane- terminated side chains are introduced to increase solubility. The three polymers were utilized as active layers in organic field-effect transistors, and the effects of thermal annealing on the polymer crystallinity and device performances were studied. Although the fluorine-atom-substituted octyl-PTTBTz-F showed a moderate hole mobility of up to 4.2 X 10-3cm2 V-1 s-1 with enhanced molecular orientation because of conformational locks, it had poor solubility in common organic solvents. The Si-PTTBTz polymer with the siloxane-terminated side chains showed good solubility but inferior device performance with a hole mobility of up to 2.2 X 10-4cm2 V-1 s-1. The rationally designed Si-PTTBTz-F polymer, which contains both fluorine atoms in the backbone and siloxane-terminated groups in the side chains, showed an excellent hole mobility of up to 0.11 cm2 V-1 s-1 and good solubility in common organic solvents.
Keywords:Organic field-effect transistor (OFET);Siloxane-terminated side chain;Thienothiophene;Benzotriazole;Conformational locking;Solubility
- Baeg KJ, Binda M, Natali D, Caironi M, Noh YY, Adv. Mater., 25(31), 4267 (2013)
- Sirringhaus H, Adv. Mater., 26(9), 1319 (2014)
- Zhang C, Chen P, Hu W, Chem. Soc. Rev., 44, 2087 (2015)
- Trung TQ, Lee NE, Adv. Mater., 28(22), 4338 (2016)
- Mazzio KA, Luscombe CK, Chem. Soc. Rev., 44, 78 (2015)
- Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z, Aldred MP, Chem. Soc. Rev., 46, 915 (2017)
- Im Y, Byun SY, Kim JH, Lee DR, Oh CS, Yook KS, Lee JY, Adv. Funct. Mater., 27, 160300 (2017)
- Zhao WC, Li SS, Yao HF, Zhang SQ, Zhang Y, Yang B, Hou JH, J. Am. Chem. Soc., 139(21), 7148 (2017)
- Kim K, Sim KM, Yoon S, Jang MS, Chung DS, Adv. Funct. Mater., 28, 180258 (2018)
- Jeong YJ, Yun DJ, Noh SH, Park CE, Jang J, ACS Nano, 12, 7701 (2018)
- Meng LX, Zhang YM, Wan XJ, Li CX, Zhang X, Wang YB, Ke X, Xiao Z, Ding LM, Xia RX, Yip HL, Cao Y, Chen YS, Science, 361(6407), 1094 (2018)
- Kroon R, Mengistie DA, Kiefer D, Hynynen J, Ryan JD, Yu L, Muller C, Chem. Soc. Rev., 45, 6147 (2016)
- Russ B, Glaudell A, Urban JJ, Chabinyc ML, Segalman RA, Nat. Rev. Mater., 1, 16050 (2016)
- Suh EH, Jeong YJ, Oh JG, Lee K, Jung J, Kang YS, Jang J, Nano Energy, 58, 585 (2019)
- Jung J, Suh EH, Jeong YJ, Yang HS, Lee T, Jang J, ACS Appl. Mater. Interfaces, 11, 47330 (2019)
- Someya T, Kato Y, Sekitani T, Iba S, Noguchi Y, Murase Y, Kawaguchi H, Sakurai T, Natl P, Acad. Sci. USA, 102, 12321 (2005)
- Rim YS, Bae SH, Chen HJ, De Marco N, Yang Y, Adv. Mater., 28(22), 4415 (2016)
- Wang SH, Xu J, Wang WC, Wang GJN, Rastak R, Molina-Lopez F, Chung JW, Niu SM, Feig VR, Lopez J, Lei T, Kwon SK, Kim Y, Foudeh AM, Ehrlich A, Gasperini A, Yun Y, Murmann B, Tok JBH, Bao ZA, Nature, 555(7694), 83 (2018)
- Kim K, Hong J, Hahm SG, Rho Y, An TK, Kim SH, Park CE, ACS Appl. Mater. Interfaces, 11, 13481 (2019)
- Pati PB, Zade SS, Cryst. Growth Des., 14, 1695 (2014)
- Nielsen CB, White AJP, McCulloch I, J. Org. Chem., 80, 5045 (2015)
- Pati PB, Org. Electron., 38, 97 (2016)
- Zhang AD, Xiao CY, Wu Y, Li C, Ji YJ, Li L, Hu WP, Wang ZH, Ma W, Li WW, Macromolecules, 49(17), 6431 (2016)
- Zhao Z, Yin Z, Chen H, Zheng L, Zhu C, Zhang L, Tan S, Wang H, Guo Y, Tang Q, Liu Y, Adv. Mater., 29, 160241 (2017)
- Ha YH, Oh JG, Park S, Kwon SK, An TK, Jang J, Kim YH, Org. Electron., 63, 250 (2018)
- Raj MR, Kim Y, Park CE, An TK, Park T, Org. Electron., 65, 251 (2019)
- Odajima T, Ashizawa M, Konosu Y, Matsumoto H, Mori T, J. Mater. Chem. C, 2, 10455 (2014)
- Venkateshvaran D, Nikolka M, Sadhanala A, Lemaur V, Zelazny M, Kepa M, Hurhangee M, Kronemeijer AJ, Pecunia V, Nasrallah I, Romanov I, Broch K, McCulloch I, Emin D, Olivier Y, Cornil J, Beljonne D, Sirringhaus H, Nature, 515(7527), 384 (2014)
- Yu SH, Park KH, Kim YH, Chung DS, Kwon SK, Macromol, 50, 4227 (2017)
- Wang Z, Liu Z, Ning L, Xiao M, Yi Y, Cai Z, Sadhanala A, Zhang G, Chen W, Sirringhaus H, Zhang D, Chem. Mater., 30, 3090 (2018)
- Lee W, Cha H, Kim YJ, Jeong JE, Hwang S, Park CE, Woo HY, ACS Appl. Mater. Interfaces, 6, 20510 (2014)
- Ngai JHL, Leung LM, So SK, Lee HKH, Org. Electron., 32, 258 (2016)
- Wu JS, Cheng YJ, Dubosc M, Hsieh CH, Chang CY, Hsu CS, Chem. Commun., 46, 3259 (2010)
- Zhang Z, Li M, Liu YH, Zhang JC, Feng SY, Xu XJ, Song JS, Bo ZS, J. Mater. Chem. A, 5, 7776 (2017)
- Li J, Yan M, Xie Y, Qiao Q, Energy Environ. Sci., 4, 4276 (2011)
- Mei J, Bao Z, Chem. Mater., 26, 604 (2013)
- Yang Y, Liu Z, Zhang G, Zhang X, Zhang D, Adv. Mater., e1903104 (2019).
- Gruber M, Jung SH, Schott S, Venkateshvaran D, Andreasen AJ, McNeill CR, Wong WWH, Shahid M, Heeney M, Lee JK, Sirringhaus H, Chem. Sci., 6, 6949 (2015)
- Shi LX, Guo YL, Hu WP, Liu YQ, Mater. Chem. Front., 1, 2423 (2017)
- Kim M, Ryu SU, Park SA, Choi K, Kim T, Chung D, Park T, Adv. Funct. Mater., 1904545 (2019).
- Lee E, Shin W, Bae O, Kim FS, Hwnag YJ, Polymer, 184, 121856 (2019)
- Neo WT, Loo LM, Song J, Wang XB, Cho CM, Chan HSO, Zong Y, Xu JW, Polym. Chem., 4, 4663 (2013)
- Cui Y, Wu Y, Lu X, Zhang X, Zhou G, Miapeh FB, Zhu W, Wang ZS, Chem. Mater., 23, 4394 (2011)
- Ye X, Zhao X, Li Q, Ma Y, Song W, Quan YY, Wang Z, Wang M, Huang ZS, Dyes Pigment., 164, 407 (2019)
- Yum S, An TK, Wang X, Lee W, Uddin MA, Kim YJ, Nguyen TL, Xu S, Hwnag S, Park CE, Woo HY, Chem. Mater., 26, 2147 (2014)
- Yum S, An TK, Wang X, Uddin MA, Nguyen TL, Xu S, Ryu H, Kim YJ, Hwang S, Park CE, Woo HY, Pure Appl. Chem., 86, 1293 (2014)
- Hwang J, Park J, Kim YJ, Ha YH, Park CE, Chung DS, Kwon SK, Kim YH, Chem. Mater., 29, 2135 (2017)
- Gu HH, Qin YC, Dai WL, Zhou D, Xie Y, Synth. Met., 251, 95 (2019)
- Lee JS, Son SK, Song S, Kim H, Lee DR, Kim K, Ko MJ, Choi DH, Kim B, Cho JH, Chem. Mater., 24, 1316 (2012)
- Mei JG, Kim DH, Ayzner AL, Toney MF, Bao ZA, J. Am. Chem. Soc., 133(50), 20130 (2011)
- Kim DH, Ayzner AL, Appleton AL, Schmidt K, Mei J, Toney MF, Bao Z, Chem. Mater., 25, 431 (2013)
- Mei JG, Wu HC, Diao Y, Appleton A, Wang H, Zhou Y, Lee WY, Kurosawa T, Chen WC, Bao ZN, Adv. Funct. Mater., 25(23), 3455 (2015)
- Prakoso SP, Ciou GT, Lin HY, Peng WC, Sie JH, Huang YF, Gan YH, Ke YJ, Wu CY, Wang CL, Tao YT, AIP Conference Proceedings, 2168, 020003 (2019)
- Kim JH, Kim HU, Song CE, Kang IN, Lee JK, Shin WS, Hwang DH, Sol. Energy Mater. Sol. Cells, 108, 113 (2013)
- Elbing M, Garcia A, Urban S, Nguyen TQ, Bazan GC, Macromol., 41, 9146 (2008)
- Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al., Gaussian, Inc., Wallingford CT, 2016.
- Zhang SQ, Qin YP, Uddin MA, Jang B, Zhao WC, Liu DL, Woo HY, Hou JH, Macromolecules, 49(8), 2993 (2016)
- Fronk SL, Wang M, Ford M, Coughlin J, Mai CK, Bazan GC, Chem. Sci., 7, 5313 (2016)
- Kaya E, Apaydin DH, Yildiz DE, Toppare L, Cirpan A, Sol. Energy Mater. Sol. Cells, 99, 321 (2012)
- Lei T, Wang JY, Pei J, Accounts Chem. Res., 47, 1117 (2014)
- Babudri F, Farinola GM, Naso F, Ragni R, Chem. Commun., 1003 (2007).
- Gu H, Qin Y, Dai W, Zhou D, Xie Y, Synth. Met., 251, 95 (2019)