정공 전달물질 및 적색발광 물질이 곁사슬에 포함된 비공액 고분자의 합성과 특성 분석

심나영; 이후성; Na Young Shim; Hoosung Lee

Polymer(Korea), Vol.29, No.5, 486-492, September, 2005

Export Citation

정공 전달물질 및 적색발광 물질이 곁사슬에 포함된 비공액 고분자의 합성과 특성 분석

Synthesis and Characterization of Non-Conjugated Polymers with Hole-Conductor and Red-Emitter in Side-Chain

심나영, 이후성^†

서강대학교 화학과

Na Young Shim, and Hoosung Lee^†

Department of Chemistry, Sogang University, 1-1 Shinsoo-Dong, Mapo-Gu, Seoul 121-742, Korea

E-mail:

초록

적색을 낼 수 있는 물질을 만들기 위해 비공액 주사슬로 되어 있는 고분자의 곁사슬에 스티렌 분자가 연결되어 있는 트리페닐아민, 반응성 있는 작용기를 가진 아미노벤즈알데히드 그룹, 및 PM(4-(dicyanomethylene)-2-(tert-butyl)-4H-pyran) 그룹을 도입하였다. 이 고분자의 전자 흡수 스펙트럼은 용액과 필름 상태에서 비슷하였다. 모든 고분자는 전기화학적으로 활성을 보였으며, 전기 발광 소자를 작동하였을 때 700 nm 근처에서 적색을 보였다. ITO/PPV/P5-PM/BCP/Alq3/Al으로 구성된 소자는 50 mA/cm2 의 낮은 전류 밀도에서 120 cd/m2 의 밝기를 보였으며, 외부 양자 효율은 0.67%를 나타내었다. 발광 고분자 층에서의 균형있는 전하의 재결합을 유도하여 소자의 발광 효율을 높일 수 있었다. 이중 가능성(bifunctionalized)을 도입함으로써 적색 발광을 내면서 효율이 높은 발광 고분자를 개발하였다.

Into a no-conjugated polymer chain we have introduced side chains with a styrene-linked triphenylamine segment as a π-electron donor, styrene-linked aminobenzaldehyde segment as a tunable reactive-CHO group, and PM (4-(dicyanomethylene)-2-(tert-butyl)-4H-pyran) moiety as a π-electron acceptor for red emitting materials. The thermal stability and the optical properties of the statistical copolymers have been studied. All the polymers were electrochemically active and showed electroluminescent emission at around 700 nm. The EL device of P5-PM based on the structure of ITO/PPV/polymer/BCP/Alq3/Al showed a maximum brightness of 120 cd/m2 at 50 mA/cm2 with an external quantum efficiency of 0.67%. It was possible to enhance the external quantum efficiency by balancing the charge recombination. A red-emitting polymer with high external quantum efficiency was developed by incorporating bifunctionality.

Keywords:polymer light emitting diode;non-conjugated polymer;red emitter;hole conductor

[References]

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Chem CH, Klubek KP, Shi J, U. S. Patent 5,908,581 (1999)
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Chen CH, Shi J, Tang CW, Macromol. Symp., 125, 1 (1997)
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Bacher E, Bayerl M, Rudati P, Reckefuss N, Muller CD, Meerholz K, Nuyken O, Macromolecules, 38(5), 1640 (2005)
Grubbs RB, Wegrzyn JK, Xia Q, Chem. Commun., 80 (2005)
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Jung BJ, Yoon CB, Shim HK, Do LM, Zyung T, Adv. Funct. Mater., 11, 430 (2001)
Peng Q, Lu ZY, Huang Y, Xie MG, Han SH, Peng JB, Cao Y, Macromolecules, 37(2), 260 (2004)
Liu YQ, Ma H, Jen AKY, Chem. Commun., 24, 2747 (2003)
Li J, Liu D, Hong Z, Tong S, Wang P, Ma C, Lengyel O, Lee C, Kwong H, Lee S, Chem. Mater., 15, 1486 (2003)
Friend RH, Pure Appl. Chem., 73, 425 (2001)
So SK, Choi WK, Leung LM, Neyts K, Appl. Phys. Lett., 74, 1939 (1999)
Woudenbergh TV, Wildeman J, Blom PWM, Bastiaansen JJAM, Langeveld-Vos BMW, Adv. Funct. Mater., 141, 677 (2004)
Inbasekaran M, Woo E, Wu W, Bernius M, Wujkowski L, Synth. Met., 111, 397 (2000)
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Coropceanu V, Gruhn NE, Barlow S, Lambert C, Durivage JC, Bill TG, Noll G, Marder SR, Bredas JL, J. Am. Chem. Soc., 126(9), 2727 (2004)
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[1] Burroughs JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB, Nature, 347, 539 (1990)

[2] Chem CH, Klubek KP, Shi J, U. S. Patent 5,908,581 (1999)

[3] Peng Q, Lu ZY, Huang Y, Xie MG, Han SH, Peng JB, Cao Y, Macromolecules, 37(2), 260 (2004)

[4] Parker ID, Marrocco M, Appl. Phys. Lett., 1994, 65 (1994)

[5] Son S, Dodabalapur A, Lovinger AJ, Galvin ME, Science, 269(5222), 376 (1995)

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

[7] Behl M, Hattemer E, Brehmer M, Zentel R, Macromol. Chem. Phys., 203, 503 (2002)

[8] Tamada M, Koshikawa H, Hosoi F, Suwa T, Usui H, Kosaka A, Sato H, Polymer, 40(11), 3061 (1999)

[9] Chen CH, Shi J, Tang CW, Macromol. Symp., 125, 1 (1997)

[10] Chen CH, Tang CW, Shi J, Klubek KP, Thin Solid Films, 363(1-2), 327 (2000)

[11] Bacher E, Bayerl M, Rudati P, Reckefuss N, Muller CD, Meerholz K, Nuyken O, Macromolecules, 38(5), 1640 (2005)

[12] Grubbs RB, Wegrzyn JK, Xia Q, Chem. Commun., 80 (2005)

[13] Hawker CJ, J. Am. Chem. Soc., 116(24), 11185 (1994)

[14] Shaheen SE, Jabbour GE, Kippelen B, peyghambarian N, Anderson JD, Marder SR, Armstrong NR, Bellmann E, Grubbs RH, Appl. Phys. Lett., 74, 3212 (1999)

[15] Jung BJ, Yoon CB, Shim HK, Do LM, Zyung T, Adv. Funct. Mater., 11, 430 (2001)

[16] Peng Q, Lu ZY, Huang Y, Xie MG, Han SH, Peng JB, Cao Y, Macromolecules, 37(2), 260 (2004)

[17] Liu YQ, Ma H, Jen AKY, Chem. Commun., 24, 2747 (2003)

[18] Li J, Liu D, Hong Z, Tong S, Wang P, Ma C, Lengyel O, Lee C, Kwong H, Lee S, Chem. Mater., 15, 1486 (2003)

[19] Friend RH, Pure Appl. Chem., 73, 425 (2001)

[20] So SK, Choi WK, Leung LM, Neyts K, Appl. Phys. Lett., 74, 1939 (1999)

[21] Woudenbergh TV, Wildeman J, Blom PWM, Bastiaansen JJAM, Langeveld-Vos BMW, Adv. Funct. Mater., 141, 677 (2004)

[22] Inbasekaran M, Woo E, Wu W, Bernius M, Wujkowski L, Synth. Met., 111, 397 (2000)

[23] Fang Q, Yamamoto T, Macromolecules, 37(16), 5894 (2004)

[24] Coropceanu V, Gruhn NE, Barlow S, Lambert C, Durivage JC, Bill TG, Noll G, Marder SR, Bredas JL, J. Am. Chem. Soc., 126(9), 2727 (2004)

[25] Bacher E, Bayerl M, Rudati P, Reckefuss N, Muller CD, Meerholz K, Nuyken O, Macromolecules, 38(5), 1640 (2005)