Syntheses and Properties of Semiconducting Polymers Based on Pyrimidine Series Substituted with Thiazolo-Pyridine

Juae Kimv; Sangmin Chae; Ahra Yi; Minji Kim; Hyo Jung Kim; Hongsuk Suh

Macromolecular Research, Vol.26, No.5, 438-445, May, 2018

DOI10.1007/s13233-018-6063-7 Export Citation

Syntheses and Properties of Semiconducting Polymers Based on Pyrimidine Series Substituted with Thiazolo-Pyridine

Juae Kimv, Sangmin Chae¹, Ahra Yi¹, Minji Kim, Hyo Jung Kim^{1, †}, and Hongsuk Suh^†

Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 46239, Korea
¹Department of Organic Material Science and Engineering, Pusan National University, Busan 46239, Korea

E-mail:,

For the utilization in the polymer solar cells, conjugated polymers were synthesized using electron-deficient units, 2-{3-[4,6-bis-(4-hexyl-thiophen-2-yl)-pyrimidin-2-yl]-phenyl}-thiazolo[5,4-b]pyridine (mTP) or 2-{4-[4,6-bis-(4-hexylthiophen-2-yl)-pyrimidin-2-yl]-phenyl}-thiazolo[5,4-b]pyridine (pTP). To increase the electron-deficiency of the pyrimidine unit, thiazolopyridine (TP), strong electron-withdrawing group, was incorporated at the meta-/para-position of the phenylene connector which is attached to the pyrimidine. It was confirmed that the TP unit at para-position has stronger intramolecular charge transfer (ICT) effect to shift the absorption to the longer wavelength region and deepens the highest occupied molecular orbital (HOMO) energy level. The polymers with 4-(1-octylnonyl)-6-(2-thienyl)-4H-thieno[3,2,-b]indole (TTI) having the decent solubility for the morphology show the superior open-circuit voltage (V OC ) value of the mTTI/pTTI devices compared to the others. Also, the polymers with TTI show increased short-circuit current (J SC ), fill factor (FF), and power conversion efficiency (PCE) due to high face-on populations.

Keywords:thiazolopyridine (TP);organic solar cells;meta-/para-position

[References]

Forrest SR, Nature, 428, 911 (2004)
Chunhui D, Fei H, Yong C, J. Mater. Chem., 22, 10416 (2012)
Li G, Zhu R, Yang Y, Nat. Photonics, 6, 153 (2012)
Walker B, Kim C, Nguyen TQ, Chem. Mater., 23, 470 (2011)
Lin Y, Ma L, Li Y, Liu Y, Zhu D, Zhan X, Adv. Eng. Mater., 3, 1166 (2013)
Demeter D, Rousseau T, Leriche P, Cauchy T, Po R, Roncali J, Adv. Funct. Mater., 21(22), 4379 (2011)
Deng P, Zhang Q, Polym. Chem., 5, 3298 (2014)
Zhang FL, Jespersen KG, Bjorstrom C, Svensson M, Andersson MR, Sundstrom V, Magnusson K, Moons E, Yartsev A, Inganas O, Adv. Funct. Mater., 16(5), 667 (2006)
Zou YP, Najari A, Berrouard P, Beaupre S, Aich BR, Tao Y, Leclerc M, J. Am. Chem. Soc., 132(15), 5330 (2010)
Piliego C, Holcombe TW, Douglas JD, Woo CH, Beaujuge PM, Frechet JMJ, J. Am. Chem. Soc., 132(22), 7595 (2010)
Huang J, Zhao Y, Ding X, Jia H, Jiang B, Zhang Z, Zhan C, He S, Pei Q, Li Y, Liu Y, Yao J, Polym. Chem., 3, 2170 (2012)
Chiu SW, Lin LY, Lin HW, Chen YH, Huang ZY, Lin YT, Lin F, Liu YH, Wong KT, Chem. Commun., 48, 1857 (2012)
Verbitskiy EV, Cheprakova EM, Subbotina JO, Schepochkin AV, et al., Dyes Pigment., 100, 201 (2014)
Kim J, Shim JY, Lee J, Lee DY, Chae S, Kim J, Kim I, Kim HJ, Park SH, Suh H, J. Polym. Sci. A: Polym. Chem., 54(6), 771 (2016)
Kim J, Lee J, Chae S, Shim JY, Lee DY, Kim I, Kim HJ, Park SH, Suh H, Polymer, 83, 50 (2016)
Yuya O, Douglas RC, Miyamoto N, Tawada M, Iwata H, Miki H, Hori A, Imamura S, Bioorg. Med. Chem., 21, 4714 (2013)
Manuela M, Raposo M, Cidalia M, Castro R, Belsley M, Mauricio A, Fonseca C, Dyes Pigment., 91, 454 (2011)
Kim J, Syntheses of Conjugated Polymers Containing Heterocycle Derivatives for High VOC in Organic Solar Cells, Pusan National University, Busan, Korea, 2017.
Smith JG, in Organic Chemistry, M. G. Hill, Ed., New York, United States, p 654-655 2011.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, et al., Gaussian 03, Revision E.01, Gaussian Inc., Wallingford, CT, USA, 2004.
James C, Blakesley, Dieter N, Phys. Rev. B, 84, 075210 (2011)
Yi YP, Coropceanu V, Bredas JL, J. Am. Chem. Soc., 131(43), 15777 (2009)
Blom PWM, Mihailetchi VD, Koster LJA, Markov DE, Adv. Mater., 19(12), 1551 (2007)
Vandewal K, Tvingstedt K, Gadisa A, Inganas O, Manca JV, Phys. Rev. B, 81, 125204 (2010)
Potscavage WJ, Potscavage A, Kippelen B, Accounts Chem. Res., 42, 1758 (2009)
Rand BP, Burk DP, Forrest SR, Phys. Rev. B, 75, 115327 (2007)
Tada A, Geng YF, Wei QS, Hashimoto K, Tajima K, Nat. Mater., 10(6), 450 (2011)
Kitchen B, Awartani O, Kline RJ, McAfee T, Ade H, O’Connor BT, ACS Appl. Mater. Interfaces, 7, 13208 (2015)
Liu F, Gu Y, Jung JW, Jo WH, Russell TP, J. Polym. Sci. B: Polym. Phys., 50(15), 1018 (2012)
Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H, Nat. Photonics, 9, 403 (2015)

[Referenced By]

[1] Forrest SR, Nature, 428, 911 (2004)

[2] Chunhui D, Fei H, Yong C, J. Mater. Chem., 22, 10416 (2012)

[3] Li G, Zhu R, Yang Y, Nat. Photonics, 6, 153 (2012)

[4] Walker B, Kim C, Nguyen TQ, Chem. Mater., 23, 470 (2011)

[5] Lin Y, Ma L, Li Y, Liu Y, Zhu D, Zhan X, Adv. Eng. Mater., 3, 1166 (2013)

[6] Demeter D, Rousseau T, Leriche P, Cauchy T, Po R, Roncali J, Adv. Funct. Mater., 21(22), 4379 (2011)

[7] Deng P, Zhang Q, Polym. Chem., 5, 3298 (2014)

[8] Zhang FL, Jespersen KG, Bjorstrom C, Svensson M, Andersson MR, Sundstrom V, Magnusson K, Moons E, Yartsev A, Inganas O, Adv. Funct. Mater., 16(5), 667 (2006)

[9] Zou YP, Najari A, Berrouard P, Beaupre S, Aich BR, Tao Y, Leclerc M, J. Am. Chem. Soc., 132(15), 5330 (2010)

[10] Piliego C, Holcombe TW, Douglas JD, Woo CH, Beaujuge PM, Frechet JMJ, J. Am. Chem. Soc., 132(22), 7595 (2010)

[11] Huang J, Zhao Y, Ding X, Jia H, Jiang B, Zhang Z, Zhan C, He S, Pei Q, Li Y, Liu Y, Yao J, Polym. Chem., 3, 2170 (2012)

[12] Chiu SW, Lin LY, Lin HW, Chen YH, Huang ZY, Lin YT, Lin F, Liu YH, Wong KT, Chem. Commun., 48, 1857 (2012)

[13] Verbitskiy EV, Cheprakova EM, Subbotina JO, Schepochkin AV, et al., Dyes Pigment., 100, 201 (2014)

[14] Kim J, Shim JY, Lee J, Lee DY, Chae S, Kim J, Kim I, Kim HJ, Park SH, Suh H, J. Polym. Sci. A: Polym. Chem., 54(6), 771 (2016)

[15] Kim J, Lee J, Chae S, Shim JY, Lee DY, Kim I, Kim HJ, Park SH, Suh H, Polymer, 83, 50 (2016)

[16] Yuya O, Douglas RC, Miyamoto N, Tawada M, Iwata H, Miki H, Hori A, Imamura S, Bioorg. Med. Chem., 21, 4714 (2013)

[17] Manuela M, Raposo M, Cidalia M, Castro R, Belsley M, Mauricio A, Fonseca C, Dyes Pigment., 91, 454 (2011)

[18] Kim J, Syntheses of Conjugated Polymers Containing Heterocycle Derivatives for High VOC in Organic Solar Cells, Pusan National University, Busan, Korea, 2017.

[19] Smith JG, in Organic Chemistry, M. G. Hill, Ed., New York, United States, p 654-655 2011.

[20] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, et al., Gaussian 03, Revision E.01, Gaussian Inc., Wallingford, CT, USA, 2004.

[21] James C, Blakesley, Dieter N, Phys. Rev. B, 84, 075210 (2011)

[22] Yi YP, Coropceanu V, Bredas JL, J. Am. Chem. Soc., 131(43), 15777 (2009)

[23] Blom PWM, Mihailetchi VD, Koster LJA, Markov DE, Adv. Mater., 19(12), 1551 (2007)

[24] Vandewal K, Tvingstedt K, Gadisa A, Inganas O, Manca JV, Phys. Rev. B, 81, 125204 (2010)

[25] Potscavage WJ, Potscavage A, Kippelen B, Accounts Chem. Res., 42, 1758 (2009)

[26] Rand BP, Burk DP, Forrest SR, Phys. Rev. B, 75, 115327 (2007)

[27] Tada A, Geng YF, Wei QS, Hashimoto K, Tajima K, Nat. Mater., 10(6), 450 (2011)

[28] Kitchen B, Awartani O, Kline RJ, McAfee T, Ade H, O’Connor BT, ACS Appl. Mater. Interfaces, 7, 13208 (2015)

[29] Liu F, Gu Y, Jung JW, Jo WH, Russell TP, J. Polym. Sci. B: Polym. Phys., 50(15), 1018 (2012)

[30] Vohra V, Kawashima K, Kakara T, Koganezawa T, Osaka I, Takimiya K, Murata H, Nat. Photonics, 9, 403 (2015)