Synthesis and Light-Emitting Properties of Phenyl-Thiophene-Based Alternating Copolymers Synthesized by Heck Coupling Reaction

Hong-Ku Shim; Taek Ahn; hye-Young Lee; Jeong-Ik Lee

Korea Polymer Journal, Vol.9, No.2, 116-121, April, 2001

Hong-Ku Shim^†, Taek Ahn, hye-Young Lee¹, and Jeong-Ik Lee²

Center of Advanced Functional Polymers, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Insitute of Science and Technology, Taejon 305-701, Korea
¹Samsung Advanced Institute of Technology, Taejon 305-380, Korea
²Basic Research Lab., Electronics and Telecommunications Research Institute, Taejon 305-350, Korea

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A series of poly(1,4-phenylenevinylene-alt-3-alkyl-2,5-thienylenevinylene)s (alkyl = hexyl [PPV-alt-6-TV] and octyl [PPV-alt-8-TV] group) have been synthesized by the Heck coupling reaction. These polymers were characterized using H(1)-NMR, FT-IR spectroscopy, and thermogravimetric analysis (TGA). They are solvent processible and have obviously copolymeric structure. The photophysical properties of the polymers were investigated using UV-visible and steady-state photoluminescence(PL) spectroscopy. We studied the change of light-emitting properties by incorporating the thiophene group into the PPV polymer backbone using alternating copolymer system. The properties of two synthesized polymers are very similar, but they exhibited apparent changes of light-emitting properties compared with other PPV backbone based polymers. The broad absorption bands from 350 to 570 nm are due to π-π* transitions of the polyconjugated systems. The absorption maxima of the two polymers were found at about 452 and 448 nm for PPV-alt-6-TV and PPV-alt-8-TV, respectively. The copolymers showed broad PL spectra between 550 and 700 nm without vibronic bands and PL emission maxims of PPValt-6-TV and PPV-alt-8-TV are about 620 and 605 nm, respectively. The copolymers exhibited the red emission (PPValt-6-TV), but more red shifted emissions are needed to obtain real red color.

[References]

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Kraft A, Grimsdale AC, Holmes AB, Angew. Chem.-Int. Edit. Engl., 37, 402 (1998)
Feast WJ, Tsibouklis J, Pouwer KL, Groenendaal L, Meijer EW, Polymer, 37(22), 5017 (1996)
Lee SJ, Kim DW, Park SY, Hong SI, Korea Polym. J., 5(1), 52 (1997)
Fox KC, New Sci., 141, 33 (1994)
Hwang DH, Jung SD, Do LM, Ahn T, Shim HK, Zyung T, Bull. Korean Chem. Soc., 19, 332 (1998)
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)
Kim HS, Noh SH, Tsutsui T, Korea Polym. J., 7(1), 18 (1999)
Skotheim TA, Elsenbaumer RL, Reynolds JR, Handbook of Conducting Polymers, 2(nd) ed., M. Dekker, New York, pp 1097. (1998)
Hilberer A, van Hutten PF, Wildeman J, Hadziioannou G, Macromol. Chem. Phys., 198, 2211 (1997)
Braun D, Heeger AJ, Appl. Phys. Lett., 58, 1982 (1991)
Gelinck GH, Warman JM, Staring EG, J. Phys. Chem., 100(13), 5485 (1996)
Hwang DH, Kim ST, Shim HK, Holmes AB, Moratti SC, Friend RH, Chem. Commun., 19, 2241 (1996)
Spreitzer H, Becker H, Kluge E, Kreuder W, Schenk H, Demandt R, Schoo H, Adv. Mater., 10, 1340 (1998)
Becker H, Spreitzer H, Kreuder W, Kluge E, Schenk H, Parker I, Cao Y, Adv. Mater., 12, 42 (2000)
Ahn T, Song SY, Shim HK, Macromolecules, 33(18), 6764 (2000)
Ahn T, Jang MS, Shim HK, Hwang DH, Zyung T, Macromolecules, 32(10), 3279 (1999)
Brassett AJ, Colaneri NF, Bradley DDC, Lawrence RA, Friend RH, Phys. Rev., B, Condens. Matter, 41, 10586 (1990)
Bao Z, Chen Y, Cai R, Yu L, Macromolecules, 26, 5281 (1993)
Storey BT, J. Polym. Sci. A: Polym. Chem., 3, 265 (1965)
Samuel IDE, Crystall B, Rumbles G, Burn PL, Holmes AB, Friend RH, Synth. Met., 54, 281 (1993)
Lemmer U, Mahrt RF, Wada Y, Greiner A, Bassler H, Gobel EO, Appl. Phys. Lett., 62, 2827 (1993)

[Referenced By]

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

[2] Kraft A, Grimsdale AC, Holmes AB, Angew. Chem.-Int. Edit. Engl., 37, 402 (1998)

[3] Feast WJ, Tsibouklis J, Pouwer KL, Groenendaal L, Meijer EW, Polymer, 37(22), 5017 (1996)

[4] Lee SJ, Kim DW, Park SY, Hong SI, Korea Polym. J., 5(1), 52 (1997)

[5] Fox KC, New Sci., 141, 33 (1994)

[6] Hwang DH, Jung SD, Do LM, Ahn T, Shim HK, Zyung T, Bull. Korean Chem. Soc., 19, 332 (1998)

[7] 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)

[8] Kim HS, Noh SH, Tsutsui T, Korea Polym. J., 7(1), 18 (1999)

[9] Skotheim TA, Elsenbaumer RL, Reynolds JR, Handbook of Conducting Polymers, 2(nd) ed., M. Dekker, New York, pp 1097. (1998)

[10] Hilberer A, van Hutten PF, Wildeman J, Hadziioannou G, Macromol. Chem. Phys., 198, 2211 (1997)

[11] Braun D, Heeger AJ, Appl. Phys. Lett., 58, 1982 (1991)

[12] Gelinck GH, Warman JM, Staring EG, J. Phys. Chem., 100(13), 5485 (1996)

[13] Hwang DH, Kim ST, Shim HK, Holmes AB, Moratti SC, Friend RH, Chem. Commun., 19, 2241 (1996)

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

[15] Becker H, Spreitzer H, Kreuder W, Kluge E, Schenk H, Parker I, Cao Y, Adv. Mater., 12, 42 (2000)

[16] Ahn T, Song SY, Shim HK, Macromolecules, 33(18), 6764 (2000)

[17] Ahn T, Jang MS, Shim HK, Hwang DH, Zyung T, Macromolecules, 32(10), 3279 (1999)

[18] Brassett AJ, Colaneri NF, Bradley DDC, Lawrence RA, Friend RH, Phys. Rev., B, Condens. Matter, 41, 10586 (1990)

[19] Bao Z, Chen Y, Cai R, Yu L, Macromolecules, 26, 5281 (1993)

[20] Storey BT, J. Polym. Sci. A: Polym. Chem., 3, 265 (1965)

[21] Samuel IDE, Crystall B, Rumbles G, Burn PL, Holmes AB, Friend RH, Synth. Met., 54, 281 (1993)

[22] Lemmer U, Mahrt RF, Wada Y, Greiner A, Bassler H, Gobel EO, Appl. Phys. Lett., 62, 2827 (1993)