Synthesis and characterization of fluorine.thiophene-based p-conjugated polymers using coupling reaction

Jang Yong Lee; Yoon Jung Kwon; Je-Wan Woo; Doo Kyung Moon

Journal of Industrial and Engineering Chemistry, Vol.14, No.6, 810-817, November, 2008

DOI10.1016/j.jiec.2008.05.005 Export Citation

Synthesis and characterization of fluorine.thiophene-based p-conjugated polymers using coupling reaction

Jang Yong Lee, Yoon Jung Kwon¹, Je-Wan Woo², and Doo Kyung Moon^†

Department of Materials Chemistry and Engineering, Konkuk University, Seoul 143-701, Republic of Korea
¹Department of Textile Engineering, College of Engineering, Konkuk University, Seoul 143-701, Republic of Korea
²Major in Industrial Chemistry, College of Natural Sciences, Sangmyung University, Seoul 110-743, Republic of Korea

E-mail:

A solution processible fluorine.thiophene-based copolymers, namely poly[2,7-bis(4-octyl-2-thienyl)-9,9-dioctylfluorene-co-alt-5,5'-(2,2'-bithiophene)] (P1), poly[2,7-bis(3-octyl-2-thienyl)-9,9-dioctylfluorene-co-alt-5,5'-(2,2'-bithiophene)] (P2), poly[2,7-bis(3,3'-dioctyl-5,5'-bithien- 2yl)-9,9'-dioctylfluorene-co-alt-5,5'-(2,2'-bithiophene)] (P3) were synthesized using Suzuki and Stille coupling reaction. The polymers showed weight loss starting around 400 ℃ indicative of good thermal stability. UV-vis properties and photoluminescence (PL) properties were investigated in toluene. P1, P2 and P3 exhibited the absorption maximum at 450, 428 and 435 nm and their PL spectrum peaked at 587, 559 and 560 nm, respectively. And all polymers, P1, P2 and P3, showed electroluminescence (EL) spectrum peaked at 592, 595 and 607 nm in the range of orange red. The polymers were electrochemically active in oxidation regions. P3 especially showed high oxidation stabilities in 1.17 V vs. Ag/Ag+. And P1 and P3 showed higher crystallinity than P2, because they have a repeated unit of 3,3"'-dialkyl-quaterthiophene.

Keywords:Conjugated polymers;Light-emitting diodes (LED);Luminescence

[References]

Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackey K, Friend RH, Burns PL, Burns AB, Holmes, Nature (London), 347, 539 (1990)
Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos DA, Bredas JL, Logdlund M, Salaneck WR, Nature, 397(6715), 121 (1999)
Tang CW, Van Slyke SA, Appl. Phys. Lett., 51, 913 (1987)
Jin SH, Park HJ, Kim JY, Lee KH, Lee SP, Moon DK, Lee HJ, Gal YS, Macromolecules, 36, 7532 (2002)
Jin SH, Yool BU, Kang SY, Gal YS, Moon DK, Opt. Mater., 21, 153 (2002)
Liu SP, Ng SC, Chan HSO, Synth. Met., 149, 1 (2005)
Liu B, Yu WL, Lai YH, Huang W, Macromolecules, 33(24), 8945 (2000)
Oh SY, Lee CH, Ryu SH, Oh HS, J. Ind. Eng. Chem., 12(1), 69 (2006)
Katz HE, Bao Z, Gilat SL, Acc. Chem. Res., 34, 359 (2001)
Yamamoto T, Yasuda T, Sakai Y, Aramaki S, Ramaw A, Macromol. Rapid Commun., 26(15), 1214 (2005)
O’Regan B, Gratzel M, Nature, 353, 737 (1991)
Schmidt-Mende L, Fechtenkotter A, Mullen K, Moons E, Friend RH, Mackenzie JD, Science, 293, 1119 (2001)
Brabec CJ, Sariciftci NS, Hummelen JC, Adv. Funct. Mater., 11(1), 15 (2001)
Crone B, Dodabalapur A, Lin YY, Filas RW, Bao Z, Laduca A, Sarpeshkar R, Katz HE, Li W, Nature (London), 403, 521 (2000)
Gelinck GH, Geuns TCT, de Leeuw DM, Appl. Phys. Lett., 77, 1487 (2000)
Klauk H, Jackson N, Solid State Technol., 43, 63 (2000)
Lin YY, Gundlach DJ, Nelson SF, Jackson TN, IEEE Trans. Electron. Devices, 44, 1325 (1997)
Cicoira F, Santato C, Dinelli F, Murgia M, Loi MA, Biscarini T, Zamboni R, Heremans P, Muccini M, Adv. Funct. Mater., 15(3), 375 (2005)
Bernius MT, Inbasekaran M, O'Brien J, Wu WS, Adv. Mater., 12(23), 1737 (2000)
Sirringhaus H, Wilson RJ, Friend RH, Inbasekaran M, Wu W, Woo EP, Crell M, Bradly DDC, Appl. Phys. Lett., 77, 406 (2000)
Ong BS, Wu YL, Liu P, Gardner S, J. Am. Chem. Soc., 126(11), 3378 (2004)
Ranger M, Rondeau D, Leclerc M, Macromolecules, 30(25), 7686 (1997)
Cho NS, Park JH, Lee SK, Lee J, Shim HK, Park MJ, Hwang DH, Jung BJ, Macromolecules, 39(1), 177 (2006)
Jayakannan M, Lou X, Van Dongen JLJ, Janssen RAJ, J. Polym. Sci. A: Polym. Chem., 43(7), 1454 (2005)
Guillerez S, Bidan G, Synth. Met., 93, 123 (1998)
Hong M, Wei HJ, Org. Chem., 65, 3894 (2000)
Wei Y, Yang Y, Yeh JM, Chem. Mater., 8, 2659 (1996)

[Referenced By]

[Related Articles]

[1] Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackey K, Friend RH, Burns PL, Burns AB, Holmes, Nature (London), 347, 539 (1990)

[2] Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos DA, Bredas JL, Logdlund M, Salaneck WR, Nature, 397(6715), 121 (1999)

[3] Tang CW, Van Slyke SA, Appl. Phys. Lett., 51, 913 (1987)

[4] Jin SH, Park HJ, Kim JY, Lee KH, Lee SP, Moon DK, Lee HJ, Gal YS, Macromolecules, 36, 7532 (2002)

[5] Jin SH, Yool BU, Kang SY, Gal YS, Moon DK, Opt. Mater., 21, 153 (2002)

[6] Liu SP, Ng SC, Chan HSO, Synth. Met., 149, 1 (2005)

[7] Liu B, Yu WL, Lai YH, Huang W, Macromolecules, 33(24), 8945 (2000)

[8] Oh SY, Lee CH, Ryu SH, Oh HS, J. Ind. Eng. Chem., 12(1), 69 (2006)

[9] Katz HE, Bao Z, Gilat SL, Acc. Chem. Res., 34, 359 (2001)

[10] Yamamoto T, Yasuda T, Sakai Y, Aramaki S, Ramaw A, Macromol. Rapid Commun., 26(15), 1214 (2005)

[11] O’Regan B, Gratzel M, Nature, 353, 737 (1991)

[12] Schmidt-Mende L, Fechtenkotter A, Mullen K, Moons E, Friend RH, Mackenzie JD, Science, 293, 1119 (2001)

[13] Brabec CJ, Sariciftci NS, Hummelen JC, Adv. Funct. Mater., 11(1), 15 (2001)

[14] Crone B, Dodabalapur A, Lin YY, Filas RW, Bao Z, Laduca A, Sarpeshkar R, Katz HE, Li W, Nature (London), 403, 521 (2000)

[15] Gelinck GH, Geuns TCT, de Leeuw DM, Appl. Phys. Lett., 77, 1487 (2000)

[16] Klauk H, Jackson N, Solid State Technol., 43, 63 (2000)

[17] Lin YY, Gundlach DJ, Nelson SF, Jackson TN, IEEE Trans. Electron. Devices, 44, 1325 (1997)

[18] Cicoira F, Santato C, Dinelli F, Murgia M, Loi MA, Biscarini T, Zamboni R, Heremans P, Muccini M, Adv. Funct. Mater., 15(3), 375 (2005)

[19] Bernius MT, Inbasekaran M, O'Brien J, Wu WS, Adv. Mater., 12(23), 1737 (2000)

[20] Sirringhaus H, Wilson RJ, Friend RH, Inbasekaran M, Wu W, Woo EP, Crell M, Bradly DDC, Appl. Phys. Lett., 77, 406 (2000)

[21] Ong BS, Wu YL, Liu P, Gardner S, J. Am. Chem. Soc., 126(11), 3378 (2004)

[22] Ranger M, Rondeau D, Leclerc M, Macromolecules, 30(25), 7686 (1997)

[23] Cho NS, Park JH, Lee SK, Lee J, Shim HK, Park MJ, Hwang DH, Jung BJ, Macromolecules, 39(1), 177 (2006)

[24] Jayakannan M, Lou X, Van Dongen JLJ, Janssen RAJ, J. Polym. Sci. A: Polym. Chem., 43(7), 1454 (2005)

[25] Guillerez S, Bidan G, Synth. Met., 93, 123 (1998)

[26] Hong M, Wei HJ, Org. Chem., 65, 3894 (2000)

[27] Wei Y, Yang Y, Yeh JM, Chem. Mater., 8, 2659 (1996)