화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.29, No.1, 89-97, January, 2021
DOI10.1007/s13233-021-9009-4  Export Citation
Impact of Intermolecular Interactions Between a Diketopyrrolopyrrole- Based Conjugated Polymer and Bromobenzaldehyde on Field-Effect Transistors
Dong Geon Koo, Dabin Lee, Juran Noh1, Yong Hyun Lee, Seohyeon Jang, Inho Nam, Tae Joo Shin2, and Juhyun Park†
  • Department of Intelligent Energy and Industry, School of Chemical Engineering and Materials Science, Chung-Ang University, Seoul 06974, Korea
  • 1Department of Materials Science and Engineering, Texas A&M University, College Station, TX 77843, USA
  • 2UNIST Central Research Facilities & School of Natural Science, Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, Korea
E-mail:
In this study, intermolecular interactions were investigated for increasing the charge carrier mobility of organic field-effect transistors (OFETs) based on a conjugated polymer. A diketopyrrolopyrrole (DPP)-based conjugated polymer widely used in OFETs, i.e., poly[2,5-(2-octyldodecyl)-3,6-diketopyrrolopyrrole-alt-5,5-(2,5-di(thien-2-yl)thieno[3,2-b]thiophene)] (PDPP-DTT), was assembled using 2-bromobenzaldehyde (2-BBA) and used as an active layer for OFETs. Morphological characterization and analysis for non-covalent intermolecular interactions suggested that the halogen bonding between the bromide of 2-BBA and electron-donor group of PDPP-DTT and the association between the electron-acceptor group in 2-BBA and sulfur of PDPP-DTT improved the hole transfer in the PDPP-DTT based OFETs. The intermolecular interactions resulting from the addition of 2-BBA contributed to the two-fold enhancement of the hole mobility, two-order increase in magnitude of the current on/off ratio, and 50% decrease in the threshold voltage of the OFETs based on PDPP-DPP.
Keywords:diketopyrrolopyrrole;organic field-effect transistors;halogen bonding;chalcogen bonding;X-ray photoelectron spectroscopy
  1. Bi S, He Z, Chen J, Li D, AIP Adv., 5, 07717 (2015)
  2. Han W, Byun M, Zhao L, Rzayev J, Lin Z, J. Mater. Chem., 21, 14248 (2011)
  3. Han W, Lin Z, Angew. Chem.-Int. Edit., 51, 1534 (2012)
  4. Kwon SW, Byun M, Yoon DH, Park JH, Kim WK, Lin Z, Yang WS, J. Mater. Chem., 21, 5230 (2011)
  5. Sun Y, Xiao G, Lin Y, Su Z, Wang Q, RSC Adv., 5, 20491 (2015)
  6. Luo C, Kyaw AKK, Perez LA, Patal S, Wang M, Grimm B, Bazan GC, Kramer EJ, Heeger AJ, Nano Lett., 14, 2764 (2014)
  7. Koizumi S, Hori M, Hayashida Y, Naito K, Kawabata S, Ishigaki Y, Kito Y, J. Soc. Inf. Disp., 27, 679 (2019)
  8. Noh J, Jung S, Koo DG, Kim G, Choi KS, Park J, Shin TJ, Yang C, Park J, Sci. Rep., 8, 14448 (2018)
  9. Wang BH, Huang W, Chi LF, Al-Hashimi M, Marks TJ, Facchetti A, Chem. Rev., 118(11), 5690 (2018)
  10. Kim G, Kang SJ, Dutta GK, Han YK, Shin TJ, Noh YY, Yang C, J. Am. Chem. Soc., 136(26), 9477 (2014)
  11. Shin EY, Cho HJ, Jung S, Yang C, Noh YY, Adv. Funct. Mater., 28, 170478 (2018)
  12. Pei M, Ko JS, Shin HH, Cho MS, Baek JI, Kim GD, Youk JH, Yang HC, Macromol. Res., 26(10), 942 (2018)
  13. Kim HS, Mun JY, Lee WH, Park YD, Macromol. Res., 26(2), 139 (2018)
  14. Lei Y, Wu B, Chan WKE, Zhu F, Ong BS, J. Mater. Chem. C, 3, 12267 (2015)
  15. Tiwari SP, Knauer KA, Dindar A, Kippelen B, Org. Electron., 13, 18 (2012)
  16. Kim DK, Lee M, Kim B, Choi JH, Org. Electron., 74, 135 (2019)
  17. Lee S, Li FM, Nathan A, IEEE. J. Electron Devices Soc., 6, 653 (2018)
  18. Tseng HR, Phan H, Luo C, Wang M, Perez LA, Patel SN, Ying L, Kramer EJ, Nguyen TQ, Bazan GC, Heeger AJ, Adv. Mater., 26(19), 2993 (2014)
  19. Feng L, Tang W, Zhao R, Hu W, Li Q, Wang R, Guo X, Sci. Rep., 6, 20671 (2016)
  20. del Pozo FG, Fabiano S, Pfattner R, Georgakopoulos S, Galindo S, Liu XJ, Braun S, Fahlman M, Veciana J, Rovira C, Crispin X, Berggren M, Mas-Torrent M, Adv. Funct. Mater., 26(14), 2379 (2016)
  21. Kim K, Kim SH, Cheon H, Jeon J, Kim YH, An TK, Polymers, 11, 1759 (2019)
  22. Sonar P, Chang J, Kim JH, Ong KH, Gann E, Manzhos S, Wu J, McNeill CR, ACS Appl. Mater. Interfaces, 8, 24325 (2016)
  23. Li J, Zhao Y, Tan HS, Ong BS, Sci. Rep., 2, 754 (2012)
  24. Bi S, Li Y, He Z, Ouyang Z, Guo Q, Jiang C, Org. Electron., 65, 96 (2019)
  25. Okachi T, Org. Electron., 57, 34 (2018)
  26. Lee JW, Park HJ, Joo JM, Hwang DH, Macromol. Res., 27(2), 115 (2019)
  27. Huang J, Pei M, Kim HS, Yang HC, Hwang DH, Macromol. Res., 27(3), 227 (2019)
  28. Madathil PK, Cho SU, Choi SI, Kim TD, Lee KS, Macromol. Res., 26(10), 934 (2018)
  29. Bronstein H, Chen ZY, Ashraf RS, Zhang WM, Du JP, Durrant JR, Tuladhar PS, Song K, Watkins SE, Geerts Y, Wienk MM, Janssen RAJ, Anthopoulos T, Sirringhaus H, Heeney M, McCulloch I, J. Am. Chem. Soc., 133(10), 3272 (2011)
  30. Kim NK, Shin ES, Noh YY, Kim DY, Org. Electron., 55, 6 (2018)
  31. Shin J, Park HW, Kim S, Yang J, Kim J, Park HW, Kim DH, Kang MS, J. Mater. Chem. C, 7, 14889 (2019)
  32. Li D, Wang Q, Huang J, Wei C, Zhang W, Wang L, Yu G, ACS Appl. Mater. Interfaces, 11, 43416 (2019)
  33. Ugur E, Khan JI, Aydin E, Wang M, Kirkus M, Neophytou M, McCulloch I, Wolf SD, J. Phys. Chem. Lett., 10, 6921 (2019)
  34. Jeon S, Lee JH, Park J, Jo B, Whang DR, Ahn TK, Park HJ, Kim SD, Lee WH, Kim BG, ACS Appl. Mater. Interfaces, 9, 22757 (2017)
  35. Yao JJ, Yu CM, Liu ZT, Luo HW, Yang Y, Zhang GX, Zhang DQ, J. Am. Chem. Soc., 138(1), 173 (2016)
  36. Frausto F, Smith ZC, Haas TE, Thomas SW, Chem. Commun., 51, 8825 (2015)
  37. Esrafill MD, Mohammadian-Sabet F, Struct. Chem., 26, 199 (2015)
  38. Mahmudov KT, Kopylovich MN, Guedes da Silva MFC, Pombeiro AJL, Dalton Trans., 46, 10121 (2017)
  39. Nikolka M, Nasrallah I, Rose B, Ravva MK, Broch K, Sadhanala A, Harkin D, Charmet J, Hurhangee M, Brown A, Illig S, Too P, Jongman J, McCulloch I, Bredas JL, Sirringhaus H, Nat. Mater., 16(3), 356 (2017)
  40. Kang I, Yun HJ, Chung DS, Kwon SK, Kim YH, J. Am. Chem. Soc., 135(40), 14896 (2013)
  41. Seo D, Park J, Shin TJ, Yoo PJ, Park J, Kwak K, Macromol. Res., 23(6), 574 (2015)
  42. Peters VN, Tumkur TU, Zhu G, Noginov MA, Sci. Rep., 5, 14620 (2015)
  43. Gavrilenko AV, Matos TD, Bonner CE, Sun SS, Zhang C, Gavrilenko VI, J. Phys. Chem. C, 112, 7908 (2008)
  44. Wu Y, Li ZJ, Ma W, Huang Y, Huo LJ, Guo X, Zhang MJ, Ade H, Hou JH, Adv. Mater., 25(25), 3449 (2013)
  45. Raghavan D, Gu X, Nguyen T, VanLandingham M, Karim A, Macromolecules, 33(7), 2573 (2000)
  46. Rajabifar B, Jadhav YM, Kiracofe D, Meyers GF, Raman A, Macromolecules, 51(23), 9649 (2018)
  47. O’Neil KD, Semenikhin OA, J. Electrochem., 46, 1345 (2010)
  48. Paterno GM, Robbiano V, Fraser KJ, Frost C, Sakai VG, Cacialli F, Sci. Rep., 7, 41013 (2017)
  49. Gora M, Krzywiec W, Mieczkowski J, Maia ECR, Louarn G, Zagorska M, Pron A, Electrochim. Acta, 144, 211 (2014)
  50. Arado OD, Monig H, Franke JH, Timmer A, Held PA, Studer A, Fuchs H, Chem. Commun., 51, 4887 (2015)
  51. Ponnappa SP, Liu Q, Umer M, MacLeod J, Jickson J, Ayoko G, Shiddiky MJA, O’Mullane AP, Sonar P, Polym. Chem., 10, 3722 (2019)
  52. Deng S, Ting YP, Water Res., 39, 2167 (2005)
  53. Zaman S, Hussain S, Butt FK, Jianguo X, Zhu C, J. Nanosci. Nanotechnol., 17, 8557 (2017)
  54. Thiry D, Pouyanne M, Cossement D, Hemberg A, Snyders R, Langmuir, 34(26), 7655 (2018)
  55. Al-Bataineh SA, Britcher LG, Griesser HJ, Surf. Sci., 600, 952 (2006)