Synthesis and Characterization of Novel Light-Emitting Copolymers with Electron-Withdrawing Substituents

Sung-Ho Jin; Dae-Sung Koo; Chan-Koo Hwang; Jung Yun Do; Young-Inn Kim; Yeong-Soon Gal; Jae Wook Lee; Jin-Taek Hwang

Macromolecular Research, Vol.13, No.2, 114-119, April, 2005

Sung-Ho Jin^†, Dae-Sung Koo, Chan-Koo Hwang, Jung Yun Do, Young-Inn Kim, Yeong-Soon Gal¹, Jae Wook Lee², and Jin-Taek Hwang³

Department of Chemistry Education and Center for Plastic Information System, Pusan National University, Busan 609-735, Korea
¹Polymer Chemsitry Lab., Kyungil University, Hayang 712-701, Korea
²Department of Chemistry, Dong-A University, Busan 604-714, Korea
³Department of Materials Sci. & Eng., Gwangju Institute of Science and Technology, Gwangju 500-712, Korea

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We synthesized two new series of alternating copolymers, poly[bis(2-(4-phenylenevinylene)-2-cyanoethenyl)-9,9-dihexyl-9H-fluoren-2,7-yl-alt-1,4-phenylene] (Polymer-I) and poly[bis(2-(4-phenylenevinylene)-2-cyanoethenyl)-9,9-dihexyl-9H-fluoren-2,7-yl-alt-2,7-(9,9-dihexylfluorene)] (Polymer-II), via the Suzuki coupling reaction, for use in light-emitting diodes (LEDs). Defect-free uniformly thin films of these polymers were found to be easily formed on indium-tin oxide (ITO) coated glass substrates. Multi-layer LEDs with ITO/PEDOT/Polymer/LiF/Al configurations with or without an Alq3 electron transport layer were fabricated with these polymers. The maximum EL emissions of Polymer-I and Polymer-II with an Alq3/LiF/Al cathode were observed at 516 and 533 nm, respectively. The maximum brightness and external luminance efficiency of the devices fabricated with the EL polymers were found to be 411 cd/m2 and 0.16 cd/A, respectively.

Keywords:electroluminescence;light-emitting polymer;light-emitting diode;luminescence efficiency

[References]

Tang CW, VanSlyke SA, Appl. Lett., 51, 913 (1987)
VanSlyke SA, Bryan PS, Tang CW, Proceedings of the 8th International Workshop on Inorganic and Organic Electroluminescence, Berlin, Germany, 1996, pp 195. (1996)
Kido J, Shionoya H, Nagai K, Appl. Phys. Lett., 67, 2281 (1995)
Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB, Nature, 347, 539 (1990)
Grem G, Leditzky G, Ullrich B, Leising G, Adv. Mater., 4, 36 (1992)
Hwang DH, Shim HK, Lee JI, Lee KS, J. Chem. Soc. Chem. Commun., 2461 (1994)
Greenham NC, Moratti SC, Bradley DDC, Friend RH, Holmes AB, Nature, 365, 628 (1993)
Liu YQ, Jiang XZ, Li QL, Zhu DB, Synth. Met., 4, 36 (1997)
Peng Z, Bao Z, Galving ME, Adv. Mater., 10, 680 (1998)
Liu YQ, Liu MS, Li XC, Jen AKY, Chem. Mater., 10, 3301 (1998)
Li XC, Liu YQ, Liu MS, Jen AKY, Chem. Mater., 11, 1568 (1999)
Johansson DM, Wang XJ, Johansson T, Inganas O, Yu G, Srdanov G, Andersson MR, Macromolecules, 35(13), 4997 (2002)
Spreitzer H, Becker H, Kluge E, Kreuder W, Schenk H, Demandt R, Schoo H, Adv. Mater., 10, 1340 (1998)
Bernius MT, Inbasekaran M, OBrien J, Wu WS, Adv. Mater., 12, 1737 (2000)
Ding JF, Day M, Robertson G, Roovers J, Macromolecules, 35(9), 3474 (2002)
Scherf U, List EJ, Adv. Mater., 14, 477 (2002)
Bouillud AD, Levesque I, Diorio M, Beaupre S, Blondin P, Ranger M, Bouchard J, Leclerc M, Chem. Mater., 12, 1931 (2000)
Zhan X, Wang S, Liu Y, Wu X, Zhu D, Chem. Mater., 15, 1963 (2003)
Jin SH, Jung JE, Park DK, Jeon BC, Kwon SK, Kim YH, Moon DK, Gal YS, Eur. Polym. J., 37, 921 (2001)
Lee JH, Yu HS, Kim W, Gal YS, Park JH, Jin SH, J. Polym. Sci. A: Polym. Chem., 38(23), 4185 (2000)
Jin SH, Sun YK, Sohn BH, Kim WH, Eur. Polym. J., 36, 957 (2000)
Jin SH, Jang MS, Suh HS, Cho HN, Lee JH, Gal YS, Chem. Mater., 14, 643 (2002)
Jin SH, Park HJ, Kim JY, Lee K, Lee SP, Moon DK, Lee HJ, Gal YS, Macromolecules, 35(20), 7532 (2002)
Jin SH, Kang SY, Kim MY, Chan YU, Kim JY, Lee K, Gal YS, Macromolecules, 36(11), 3841 (2003)
Jin SH, Kim MY, Kim JY, Lee K, Gal YS, J. Am. Chem. Soc., 126(8), 2474 (2004)
Jin SH, Kim MY, Park SH, Lee K, Gal YS, Chem. Mater., 16, 3299 (2004)
Yu WL, Pei J, Cao Y, Huang W, Heeger AJ, Chem. Commun., 1837 (1999)

[Referenced By]

[Related Articles]

[1] Tang CW, VanSlyke SA, Appl. Lett., 51, 913 (1987)

[2] VanSlyke SA, Bryan PS, Tang CW, Proceedings of the 8th International Workshop on Inorganic and Organic Electroluminescence, Berlin, Germany, 1996, pp 195. (1996)

[3] Kido J, Shionoya H, Nagai K, Appl. Phys. Lett., 67, 2281 (1995)

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

[5] Grem G, Leditzky G, Ullrich B, Leising G, Adv. Mater., 4, 36 (1992)

[6] Hwang DH, Shim HK, Lee JI, Lee KS, J. Chem. Soc. Chem. Commun., 2461 (1994)

[7] Greenham NC, Moratti SC, Bradley DDC, Friend RH, Holmes AB, Nature, 365, 628 (1993)

[8] Liu YQ, Jiang XZ, Li QL, Zhu DB, Synth. Met., 4, 36 (1997)

[9] Peng Z, Bao Z, Galving ME, Adv. Mater., 10, 680 (1998)

[10] Liu YQ, Liu MS, Li XC, Jen AKY, Chem. Mater., 10, 3301 (1998)

[11] Li XC, Liu YQ, Liu MS, Jen AKY, Chem. Mater., 11, 1568 (1999)

[12] Johansson DM, Wang XJ, Johansson T, Inganas O, Yu G, Srdanov G, Andersson MR, Macromolecules, 35(13), 4997 (2002)

[13] Spreitzer H, Becker H, Kluge E, Kreuder W, Schenk H, Demandt R, Schoo H, Adv. Mater., 10, 1340 (1998)

[14] Bernius MT, Inbasekaran M, OBrien J, Wu WS, Adv. Mater., 12, 1737 (2000)

[15] Ding JF, Day M, Robertson G, Roovers J, Macromolecules, 35(9), 3474 (2002)

[16] Scherf U, List EJ, Adv. Mater., 14, 477 (2002)

[17] Bouillud AD, Levesque I, Diorio M, Beaupre S, Blondin P, Ranger M, Bouchard J, Leclerc M, Chem. Mater., 12, 1931 (2000)

[18] Zhan X, Wang S, Liu Y, Wu X, Zhu D, Chem. Mater., 15, 1963 (2003)

[19] Jin SH, Jung JE, Park DK, Jeon BC, Kwon SK, Kim YH, Moon DK, Gal YS, Eur. Polym. J., 37, 921 (2001)

[20] Lee JH, Yu HS, Kim W, Gal YS, Park JH, Jin SH, J. Polym. Sci. A: Polym. Chem., 38(23), 4185 (2000)

[21] Jin SH, Sun YK, Sohn BH, Kim WH, Eur. Polym. J., 36, 957 (2000)

[22] Jin SH, Jang MS, Suh HS, Cho HN, Lee JH, Gal YS, Chem. Mater., 14, 643 (2002)

[23] Jin SH, Park HJ, Kim JY, Lee K, Lee SP, Moon DK, Lee HJ, Gal YS, Macromolecules, 35(20), 7532 (2002)

[24] Jin SH, Kang SY, Kim MY, Chan YU, Kim JY, Lee K, Gal YS, Macromolecules, 36(11), 3841 (2003)

[25] Jin SH, Kim MY, Kim JY, Lee K, Gal YS, J. Am. Chem. Soc., 126(8), 2474 (2004)

[26] Jin SH, Kim MY, Park SH, Lee K, Gal YS, Chem. Mater., 16, 3299 (2004)

[27] Yu WL, Pei J, Cao Y, Huang W, Heeger AJ, Chem. Commun., 1837 (1999)