Effects of Different Eelectron-withdrawing Moieties on the General Photoelectric Properties of Fluorene-based Dimers

Abstract

Here, 9,9,9′-tris(4-butoxyphenyl)-9H-9′H-2,2′-difluorene(DF) was synthesized as a reference for comparison, and diphenyl sulfone and triphenylphosphine oxygen were introduced to the 9-position of fluorene through a C-H coupling reaction to produce two fluorene-based oligomers 9′,9′″-[sulfonylbis(4,1-phenylene)]bis[9,9,9′-tris-(4-butoxyphenyl)-9H,9′H-2,2′-bifluorene](DF)₂SO₂ and phenylbis(4-{9,9′,9′-tris(4-butoxyphenyl)-9H,9′H-[2,2′-bifluorene]-9-yl}phenyl)phosphine oxide[(DF)₂PO]. Solid powders of all the three compounds exhibit excellent thermal stability with thermal temperature at 5% mass loss of 375, 429 and 383 °C for (DF)₂SO₂, (DF)₂PO and DF. In addition, owing to the distorted molecular structure and weak electron-absorbing ability of the acceptor, (DF)₂SO₂ and (DF)₂PO do not have obvious intramolecular charge transfer characteristics, and exhibit stable localized 394 nm/375 nm fluorescence emission peaks in different polar solvents. The absolute luminescence quantum efficiencies of (DF)₂SO₂, (DF)₂PO and DF solid powders are 20.83%, 10.03% and 59.46%. Compound DF has the highest quantum yield as an electron donor. The chromaticity coordinates of the blue OLED devices based on DF and DF₂SO₂ fabricated by solution spin coating were (0.19, 0.10) and (0.19, 0.11), which were closest to the deep blue region, and the corresponding maximum external quantum efficiencies are 1.45% and 0.87%, respectively, which are higher than that of (DF)₂PO(0.25%) and consistent with the difference in the solid-state quantum efficiency between them.

Keywords

Organic light emitting-diode / Electron-withdrawing moiety / Fluorene / Diphenyl sulfone / Triphenylphosphine oxide

References

[1] Baldo M A, O’Brien D F, Forrest S R. Phys. Rev. B, 1999, 60: 14422.

[2] Tang C W, Vanslyke S A. Appl. Phys. Lett., 1987, 51: 913.

[3] Baldo M A, O’Brien D F, You Y J, Shoustikov A. Nature, 1998, 395: 151.

[4] Sasabe H, Kido J. Eur. J. Org. Chem., 2013, 2013: 7653.

[5] Minaev B, Baryshnikov G, Agren H. Phys. Chem. Chem. Phys., 2014, 16: 1719.

[6] Endo A, Ogasawara M, Takahashi A, Yokoyama D, Kato Y, Adachi C. Adv. Mater., 2009, 21: 4802.

[7] Zhu M R, Yang C L. Chem. Soc. Rev., 2013, 42: 4963.

[8] Lin M S, Chi L C, Chang H W, Huang Y H, Chi Y A. J. Mater. Chem., 2011, 22: 870.

[9] Tan J H, Huo Y P, Cai N, Ji S M, Li Z Z, Zhang L. Chin. J. Org. Chem., 2017, 37: 2457.

[10] Jiang H J. Macromol. Rapid Commun., 2010, 31: 2007.

[11] Wei L J, Li J, Xue K, Ye S H, Jiang H J. New J. Chem., 2019, 43: 16629.

[12] Gong S, Jiang J, Yang C. Chem. Eur. J., 201, 22: 10860.

[13] Xiang Y, Gong S, Zhao Y, Yin X, Luo J, Wu K, Lu Z, Yang C. J. Mater. Chem. C, 201, 4: 9998.

[14] Lee J, Shizu K, Tanaka H, Nakanotani H, Yasuda T, Kaji H, Adachi C. J. Mater. Chem. C, 2015, 3: 2175.

[15] Duan C, Li J, Han C, Ding D, Yang H, Wei Y, Xu H. Chem. Mater., 201, 28: 5667.

[16] Liu M, Seino Y, Chen D, Chen D, Inomata S, Kido J. Chem. Commun., 2015, 51: 16353.

[17] Zhang Q, Kuwabara H, Potscavage W J, Huang S, Hatae Y, Shibata T, Adachi C. J. Am. Chem. Soc., 2014, 136: 18070.

[18] Hirai H, Nakajima K, Nakatsuka S, Shiren K, Ni J, Nomura S, Ikuta T, Hatakeyama T. Angew. Chem. Int. Ed., 2015, 54: 13581.

[19] Li J, Zhang Q, Nomura H, Miyazaki H, Adachi C. Appl. Phys. Lett., 2014, 105: 1.

[20] Li J, Nakagawa T, Macdonald J, Zhang Q, Nomura H, Miyazaki H, Adachi C. Adv. Mater., 2013, 25: 3319.

[21] Suzuki K, Kubo S, Shizu K, Fukushima T, Wakamiya A, Murata Y, Adachi C, Kaji H. Angew. Chem. Int. Ed., 2015, 54: 15231.

[22] Lee S Y, Yasuda T, Park I S, Adachi C. J. Chem. Soc. Dalton. Trans., 2015, 44: 8356.

[23] Wu T L, Liao S Y, Huang P Y, Hong Z S, Huang M P, Lin C C, Cheng M J, Cheng C H. ACSAppl. Mater. Inter., 2019, 11: 19294.

[24] Krishnamoorthy T, Ding H, Yan C, Leong W, Baikie T, Zhang Z, Sherburne M, Li S, Asta M, Mathews N, Mhaisalkar S G. J. Mater. Chem. A, 2015, 3: 23829.

[25] Omer K M, Ku S Y, Wong K T, Bard A J. Angew. Chem. Int. Ed., 2009, 121: 9464.

[26] Wu C H, Shih P I, Shu C F, Chi Y. Appl. Phys. Lett., 2008, 92: 233303.

[27] Chien C H, Hsu F M, Shu C F, Chi Y. Org. Electron., 2009, 10: 871.

[28] Uoyama H, Goushi K, Shizu K, Nomura H, Adachi C. Nature, 2012, 492: 234.

[29] Kim O Y, Kim B S, Lee J Y. Synth. Met., 2015, 201: 49.

[30] Sun M L, Zhu W S, Zhang Z S, Qu C J, Xie L H, Yang Y, Qian Y, Zhao Y, Huang W. J. Mater. Chem. C, 2015, 3: 94.

[31] Liu F, Xie L H, Tang C, Liang J, Chen Q Q, Peng B, Wei W, Cao Y, Huang W. Org. Lett., 2009, 11: 3850.

[32] Poriel C, Sicard L, Joëlle R-B. Chem. Commun., 2019, 55: 14238.

[33] Tseng Y H, Shih P I, Chien C H, Dixit A K, Shu C F, Liu Y H, Lee G H. Macromolecules, 2005, 38: 10055.

[34] Xin Y, Wen G A, Zeng W J, Zhao L, Zhu X R, Fan Q L, Feng J C, Wang L H, Peng B, Cao Y. Macromolecules, 2005, 38: 6755.

[35] Bernius M, Inbasekaran M, Woo E, Wu W, Wujkowski L. J. Mater. Sci. Mater. Electron., 2000, 11: 111.

[36] Bai K, Wang S, Zhao L, Ding J, Wang L. Macromolecules, 2017, 50: 6945.

[37] Wong K T, Chien Y Y, Chen R T, Wang C F, Lin Y T, Chiang H H, Hsieh P Y, Wu C C, Chou C H, Su Y O, Lee G H, Peng S M. J. Am. Chem. Soc., 2002, 124: 11576.

[38] Wong K T, Chen R T, Fang F C, Wu C C, Lin Y T. Org. Lett., 2005, 7: 5925.

[39] Tao S, Zhou Y, Lee C S, Zhang X, Lee S T. Chem. Mater., 2010, 22: 2138.

[40] Wu F I, Reddy D S, Shu C F, Liu M S, Jen K Y. Chem. Mater, 2003, 15: 269.

[41] Grisorio R, Allegretta G, Mastrorilli P, Suranna G P. Macromolecules, 2011, 44: 7977.

[42] Hu X D, Wang S H, Hou Z X, Wang M H, Wang N. Adv. Mater. Res., 2015, 1089: 20.

[43] He X, Xiao Y P, Yuan X L, Ye S H, Jiang H J. Chin. J. Org. Chem., 2019, 37: 761.

[44] Cao X, Yang W, Liu C, Wei F L, Wu K, Sun W, Song J, Xie L H, Huang W. Org. Lett, 2013, 15: 3102.

[45] Jiang H J, He X, Li X. Chin. J. Org. Chem., 2020, 40: 763.

[46] An Z F, Chen R F, Yin J, Xie G H, Shi H F, Tsuboi T, Huang W. Chem. Eur. J., 2011, 17: 10871.

[47] Tanaka H, Shizu K, Miyazaki H, Adachi C. Chem. Commun., 2012, 48: 11392.

[48] Ishiyama T, Murata M, Miyaura N. J. Org. Chem., 1995, 60: 7508.

[49] Jiang H J, Zhang Q W, He X, Zhang X L, Zhang X W. Chin. J. Polym. Sci., 2017, 35: 611.

[50] Jou J H, Li J L, Sahoo S, Dubey D K, Yadav R A K, Joseph V, Cheng C H. J. Phys. Chem. C, 2018, 122: 24295.

[51] Bulovic V, Deshpande R, Thompson M E, Forrest S R. Chem. Phys. Lett., 1999, 308: 317.

[52] Li W, Liu D, Shen F, Ma D, Wang Z, Feng T, Xu Y, Yang B, Ma Y. Adv. Funct. Mater., 2012, 22: 2797.

[53] Zong L, Xie Y, Wang C, Li J R, Li Q, Li Z. Chem. Commun., 201, 52: 11496.

[54] Mei J, Hong Y, Jacky W Y L, Qin A, Tang Y, Tang B Z. Adv. Mater., 2014, 26: 5429.

[55] Liu Y, Wang Y, Li C, Ren Z, Ma D, Yan S. Macromolecules, 2018, 51: 4615.

[56] Zhao B, Zhang T, Chu B, Li W, Su Z, Luo Y, Li R, Yan X, Jin F, Gao Y, Wu H. Org. Electron, 2015, 17: 15.

[57] Wang Q, Tian Q S, Zhang Y L, Tang X, Liao L S. J. Mater. Chem. C, 2019, 7: 11329.

[58] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Montgomery J A, Vreven J, Kudin T K N, Burant J C, Millam J M, Iyengar S S, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A, Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C, Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q, Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin R L, Fox D J, Keith T, AlLaham M A, Peng C Y, Nanayakkar A, Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A. Gaussian 09, Revision A02, 2009, Wallingford CT: Gaussian Inc.