Benzothiadiazole을 기본골격으로 한 공액형 올리고머 합성 및 유기태양전지 응용

신웅; 김윤환; Nadhila Sylvianti; Mutia Anissa Marsya; Devi Saskia Putri; 문두경; 김주현; Woon Shin; Youn Hwan Kim; Nadhila Sylvianti; Mutia Anissa Marsya; Devi Saskia Putri; Doo Kyung Moon; Joo Hyun Kim

Polymer(Korea), Vol.40, No.6, 960-966, November, 2016

DOI10.7317/pk.2016.40.6.960 Export Citation

Benzothiadiazole을 기본골격으로 한 공액형 올리고머 합성 및 유기태양전지 응용

Synthesis of Conjugated Oligomer Based on Benzothiadiazole and Its Application of Organic Solar Cells

신웅, 김윤환, Nadhila Sylvianti, Mutia Anissa Marsya, Devi Saskia Putri, 문두경 ¹, 김주현^†

부경대학교 고분자공학과
¹건국대학교 신소재공학과

Woon Shin, Youn Hwan Kim, Nadhila Sylvianti, Mutia Anissa Marsya, Devi Saskia Putri, Doo Kyung Moon¹, and Joo Hyun Kim^†

Department of Polymer Engineering, Pukyong National University, Busan 48547, Korea
¹Department of Materials Chemistry and Engineering, Konkuk Univerisity, Seoul 05029, Korea

E-mail:

초록

2,1,3-benzothiadiazole(BT)과 silofluorene(SiF)을 기본골격으로 하는 acceptor(A) - donor(D) - acceptor(A) 형태의 공액형(conjugated) 분자(SiF-BT)를 합성하였다. 공액결합의 길이를 늘여 주기 위하여 두 개의 thiophene을 SiF와 BT 사이에 도입하였으나 밴드갭은 꽤 큰 2.26 eV에 불과하였다. 이는 SiF와 BT 사이의 intramolecular charge transfer 의 정도가 작기 때문이라 판단된다. 순환전압전류법 및 흡수분광법을 이용하여 측정한 SiF-BT의 HOMO 및 LUMO 에너지 준위는 각각 -5.43 and -3.17 eV이며, 최적화된 유기태양전지의 효율은 0.53%(단락전류=-2.06 mA/cm2, 충진인자=29.8%, 개방전압=0.90 V)임을 확인하였다.

Acceptor (A) - donor (D) - acceptor (A) type conjugated small molecule based on 2,1,3-benzothiadiazole and silofluorene (2,7-bis[5-(7-methyl-benzo[1,2,5]thiadiazol-4-yl)-thiophen-2-yl]-9-(9,9-dioctyl)-9H-silofluorene, SiF-BT) is synthesized for application in organic solar cells (OSCs). Even though two thiophene rings are introduced as the π-extender, SiF-BT exhibits a wide band gap of 2.26 eV due to weak intramolecular charge transfer between SiF and BT. The HOMO and LUMO energy levels of SiF-BT figured out from the cyclic voltammogram and UV-Visible spectrum are -5.43 and -3.17 eV, respectively. Optimized OSCs with a blend of SiF-BT:PC71BM (3:6) exhibits a power conversion efficiency (PCE) of 0.53% with a short-circuit current density of -2.06 mA/cm2, fill factor of 29.8%, and open-circuit voltage of 0.90 V.

Keywords:conjugated oligomer;silofluorene;benzothiadiazole;organic solar cell

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[2] Wessendorf CD, Rodriguez AP, Hanisch J, Arndt AP, Ata I, Schulz GL, Quintilla A, Bauerle P, Lemmer U, Wochner P, Ahlswede E, Barrena E, J. Mater. Chem., 4, 2571 (2016)

[3] Zhou C, Liang YM, Liu F, Sun C, Huang XL, Xie ZQ, Huang F, Roncali J, Russell TP, Cao Y, Adv. Funct. Mater., 24(47), 7538 (2014)

[4] Yuan L, Zhao YF, Zhang JQ, Zhang YJ, Zhu LY, Lu K, Yan W, Wei ZX, Adv. Mater., 27(28), 4229 (2015)

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[6] Ku J, Lansac Y, Jang YH, J. Phys. Chem. C, 115, 21508 (2011)

[7] Park G, Ryu I, Yim S, Bull. Korean Chem. Soc., 32, 943 (2011)

[8] Tregnago G, Steckler TT, Fenwick O, Andersson MR, Cacialli F, J. Mater. Chem. C, 3, 2792 (2015)

[9] Marzari G, Durantini J, Minudri D, Gervaldo M, Otero L, Fungo F, Pozzi G, Cavazzini M, Orlandi S, Quici S, J. Phys. Chem. C, 116, 21190 (2012)

[10] Rodrigues PC, Berlim LS, Azevedo D, Saavedra NC, Prasad PN, Schreiner WH, Atvars TDZ, Akcelrud L, J. Phys. Chem. A, 116, 3681 (2012)

[11] Mori D, Benten H, Ohkita H, Ito S, Miyake K, ACS Appl. Mater. Interfaces, 4, 3325 (2012)

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[13] Lu J, Xia PF, Lo PK, Tao Y, Wong MS, Chem. Mater., 18, 6194 (2006)

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[16] Kim JB, Allen K, Oh SJ, Lee S, Toney MF, Kim YS, Kagan CR, Nuckolls C, Loo YL, Chem. Mater., 22, 5762 (2010)

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[18] Yamamoto NAD, Lavery LL, Nowacki BF, Grova IR, Whiting GL, Krusor B, Azevedo ER, Akcelrud L, Arias AC, Roman LS, J. Phys. Chem. C, 116, 18641 (2012)

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[20] Huang H, Youn J, Ortiz RP, Zheng Y, Facchetti A, Marks T, Chem. Mater., 23, 2185 (2011)

[21] Yamaguchi S, Tamao K, Bull. Chem. Soc. Jpn., 69, 2327 (1996)

[22] Song S, Choi HI, Shin IS, Hyun MH, Suh H, Park SS, Park SH, Jin Y, Bull. Korean Chem. Soc., 35, 2963 (2014)

[23] Jorgensen M, Krebs FC, J. Org. Chem., 70, 6004 (2005)

[24] Chan KL, McKiernan MJ, Towns CR, Holmes AB, J. Am. Chem. Soc., 127(21), 7662 (2005)

[25] Shin W, Park JH, Lim GE, Sylvianti N, Ahn BH, Kim JH, Synth. Met., 210, 201 (2015)

[26] Xue J, Uchida S, Rand BP, Forrest SR, Appl. Phys. Lett., 84, 3013 (2004)

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