Biphenylrl를 포함하는 공액 공중합체의 합성 및 전계발광 특성

박이순; 한유수; 김상대; 김우식; 이동호; 민경은; 서관호; 강인규; Lee Soon Park; Yoon Soo Han; Sang Dae Kim; Woo Sik Kim; Dong Ho Lee; Kyung Eun Min; Kwan Ho Seo; Inn Kyu Kang

Journal of the Korean Industrial and Engineering Chemistry, Vol.11, No.4, 439-445, June, 2000

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Biphenylrl를 포함하는 공액 공중합체의 합성 및 전계발광 특성

Syntheis of Conjugated Copojugated Copolymers containing Biphenyl Group and Their Electroluminescence Characteristics

박이순 ^†, 한유수, 김상대, 김우식 , 이동호 , 민경은 , 서관호 , 강인규

경북대학교 공과대학 고분자공학과, 대구 702-701

Lee Soon Park^†, Yoon Soo Han, Sang Dae Kim, Woo Sik Kim , Dong Ho Lee , Kyung Eun Min , Kwan Ho Seo , and Inn Kyu Kang

Department of Polymer Science, Kyungpook National University, Taegu 702-701, Korea

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초록

Poly(2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene)(MEH-PPV) 및 주쇄에 서로 다른 조성비의 biphenylrl를 포함하는 poly(2-methoxy-5-(2-ethylhexyl-oxy)-1,4-phenylene vinylene-co-1,1''-biphenyl-4,4''-ylene vinylene) [poly(MEHPV-co-BPV)] 공중합체를 α-elimination 법으로 합성하였다. 또한 교대 공중합체인 Poly(2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene-alt-1,1''-biphenyl-4,4''-ylene vinylene) [poly(MEHPV-alt-BPV)] 및 고분자 주쇄내에 공액 영역과 비공액 영역이 교대로 배열된 poly(1,8-octanedioxy-2-methoxy-1,4-phenylene-1,2-ethenylene-1,1''-biphenyl-4,4''-ylene-1,2-ethenylene-3-methoxy-1,4-phenylene) [poly(BFMP8-BPV)]와 poly(1,12-dodecaedioxy-s-methoxy-1,4-phenylene-1,2-ethenylene-1,1''-biphenyl4,4''-ylene-1,2-ethenylene-3-methoxy-1,4-phenylene)[poly(BFMP12-BPV)]를 Honer~ Emmons 반응으로 각각 합성하였다. 합성된 고분자를 발광층으로 하는 단일 EL 소자를 제작하여 이들의 광전기적인 특성을 비교, 평가하였다. Poly(MEHPV-co-BPV)의 경우 BPV기가 도입됨에 따라 용해도가 현저히 감소하였으며 MEHPV 반복단위에 의한 발광 (586nm)과 BPV 반복단위에 의한 발광(469, 495nm)이 동시에 관찰되었고, poly(MEHPV-alt-BPV)의 경우 두 반복단위의 중간지점 (544 nm)에서 최대 발광이 나타났다.

Poly(2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene)(MEH-PPV) and poly(2-methoxy-5-(2-ethylhexyl-oxy)-1,4-phenylene vinylene-co-1,1''-biphenyl-4,4''-ylene vinylene) [poly(MEHPV-co-BPV)] with a different feed ratio of biphenyl group in the main chain were synthesized by α-elimination reaction. Poly(2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene-alt-1,1''-biphenyl-4,4''-ylene vinylene) [poly(MEHPV-alt-BPV)], which has alternating repeat unit, and poly(1,8-octanedioxy-2-methoxy-1,4-phenylene-1,2-ethenylene-1,1''-biphenyl-4,4''-ylene-1,2-ethenylene-3-methoxy-1,4-phenylene) [poly(BFMP8-BPV)] and poly(1,12-dodecaedioxy-s-methoxy-1,4-phenylene-1,2-ethenylene-1,1''-biphenyl4,4''-ylene-1,2-ethenylene-3-methoxy-1,4-phenylene)[poly(BFMP12-BPV)] containing both conjugated and non-conjugated group in the main chain were synthesized by the Honer-Emmons were examined. The solubility of poly(MEHPV-co-BPV)s in common organic solvents decreased rapidly with the increasing amount of BPV units in the copolymer. Emission spectrum of poly(MEHPV-co-BPV)s had two peaks corresponding to MEPHV(586 nm) and BPV(469, 495 nm) moiety, respctively. However, LED fabricated with poly(MEHPV-alt-BPV)showed relatively sharp single peak(544 nm) in the middle of the two peaks.

Keywords:light-emitting diode;conjugated polymer;α-elimination;honer-emmons reaction

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Gurge RM, Sarker AM, Lahti PM, Hu B, Karasz FE, Macromolecules, 30(26), 8286 (1997)
Bradley DDC, Synth. Met., 54, 401 (1993)
Yoon CB, Kang IN, Shim HK, J. Polym. Sci. A-Polym. Chem., 35(11), 2253 (1997)
Kaeriyama K, Tsukahara Y, Negora S, Tanigaki N, Masuda H, Synth. Met., 84, 263 (1997)
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Bao Z, Chen Y, Cai R, Yu L, Macromolecules, 26, 5281 (1993)
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Sokolik I, Yang Z, Karasz FE, J. Appl. Phys., 74(5), 3584 (1993)
Agoston GA, "Color Theory and Its Application in Art and Design," D.L. MacAdam, 19, 57, Springer-Verlag, Berlin (1979)
Pavia DL, Lampman GM, Kriz GS, "Introduction to Spectroscopy: A Guide for Students of Organic Chemistry," 200, W.B. Sunders Company, Philadelphia (1979)

[Related Articles]

[1] Burn PL, Bradley DDC, Friend RH, Halliday DA, Holmes AB, Jackson RW, Kraft A, J. Chem. Soc.-Perkin Trans. 1, 1, 3225 (1992)

[2] Askari SH, Rughooputh SD, Wudl F, Synth. Met., 29, E129 (1989)

[3] Gurge RM, Sarker AM, Lahti PM, Hu B, Karasz FE, Macromolecules, 30(26), 8286 (1997)

[4] Bradley DDC, Synth. Met., 54, 401 (1993)

[5] Yoon CB, Kang IN, Shim HK, J. Polym. Sci. A-Polym. Chem., 35(11), 2253 (1997)

[6] Kaeriyama K, Tsukahara Y, Negora S, Tanigaki N, Masuda H, Synth. Met., 84, 263 (1997)

[7] Hwang DH, Kim ST, Shim HK, Holmes AB, Moratti SC, Friend RH, Synth. Met., 84, 615 (1997)

[8] Wudl F, Srdanov G, U.S. Patent, 5,189,136 (1993)

[9] Doi S, Kuwabara M, Noguchi T, Ohnishi T, Synth. Met., 55-57, 4174 (1993)

[10] Klanderman BH, J. Org. Chem., 31, 2618 (1966)

[11] Peake SL, U.S. Patent, 4,588,163 (1985)

[12] Paquette LA, "Encyclopedia of Reagents for Organic Synthesis," 7, 5082, John Wiley & Sons, New York (1995)

[13] Larsen M, Krebs FC, Jorgensen M, Harrit N, J. Org. Chem., 63, 4420 (1998)

[14] Kim Y, Kwon S, Yoo D, Rubner MF, Wrighton MS, Chem. Mater., 9, 2699 (1997)

[15] Gurge RM, Hickl M, Krause G, Lahti PM, Hu B, Yang Z, Karasz FE, Polym. Adv. Technol., 9, 504 (1998)

[16] Yang Z, Sokolik I, Karasz FE, Macromolecules, 26, 1188 (1993)

[17] Brandon KL, Bently PG, Bradley DD, Dunmur DA, Synth. Met., 91, 305 (1997)

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

[19] Suppan P, "Chemistry and Light," 55, The Royal Society of Chemistry, Cambridge (1994)

[20] Sokolik I, Yang Z, Karasz FE, J. Appl. Phys., 74(5), 3584 (1993)

[21] Agoston GA, "Color Theory and Its Application in Art and Design," D.L. MacAdam, 19, 57, Springer-Verlag, Berlin (1979)

[22] Pavia DL, Lampman GM, Kriz GS, "Introduction to Spectroscopy: A Guide for Students of Organic Chemistry," 200, W.B. Sunders Company, Philadelphia (1979)