벤족사졸 화합물을 함유한 고분자 박막에서 형광 패터닝

김태훈; 장근석; 이택승; Tae Hoon Kim; Geunseok Jang; Taek Seung Lee

Polymer(Korea), Vol.41, No.4, 641-647, July, 2017

DOI10.7317/pk.2017.41.4.641 Export Citation

벤족사졸 화합물을 함유한 고분자 박막에서 형광 패터닝

Fluorescence Patterning on the Polymer Films Containing a Benzoxazole Compound

김태훈^{1, 2}, 장근석¹, 이택승^{1, †}

¹충남대학교 유기재료공학과
²SKC Haas 디스플레이필름

Tae Hoon Kim^{1, 2}, Geunseok Jang¹, and Taek Seung Lee^{1, †}

¹Organic and Optoelectronic Materials Laboratory, Department of Organic Materials Engineering, Chungnam National University, Daejeon 34134, Korea
²SKC Haas Display Films, 112 Seonggeo-gil, Seonggeo-eup, Seobuk-gu, Cheonan-si, Chungcheongnam-do 31044, Korea

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초록

광기록 저장재료로서 벤족사졸을 사용하기 위하여 벤족사졸 유도체(PPHBO)를 2,5-dihexyloxybenzene-1,4-diboronic acid와 t-butoxycarbonyl(t-Boc)기로 치환된 벤족사졸을 사용하여 합성하였으며, 이의 광학적 성질을 측정하고, UV 조사에 의해 형광색이 변화하는 특성을 이용하여 형광 패터닝을 수행하였다. t-Boc기가 보호/탈보호된 벤족사졸 화합물의 용액에서와 고상에서 광학적 성질을 분자 conformation 관점에서 분석하였으며, 이를 기반으로 이화합물의 분자내 양성자 이동 특성을 이용하여 형광 패터닝에 사용하였다. 벤족사졸 화합물을 PVA와 혼합하고, 실리콘 웨이퍼를 기판으로 하여 UV 조사에 의하여 형광이 변화하는 특성을 이용하여 UV 광기록 및 삭제를 실시하여 광기록 저장재료로서 활용성을 연구하였다.

p-Phenylene dihydroxyphenylbenzoxazole (PPHBO) compound was synthesized with t-butoxycarbonyl (t-Boc)-protected benzoxazole moiety and 2,5-dihexyloxybenzene-1,4-diboronic acid, followed by cleavage of the t-Boc group, in which PPHBO would be used for optical recording because of its unique photophysical properties. The optical properties of PPHBO were investigated in solution and in the solid state in terms of molecular conformation. The intramolecular proton transfer in PPHBO was used for fluorescence patterning. The solid film (mixed with PVA) on silicon wafer showed fluorescence quenching under UV irradiation, which was used for photo-triggered recording and erasing.

Keywords:hydroxyphenylbenzoxazole;fluorescence patterning;optical recording

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[1] Jia CC, Migliore A, Xin N, Huang SY, Wang JY, Yang Q, Wang SP, Chen HL, Wang DM, Feng BY, Liu ZR, Zhang GY, Qu DH, Tian H, Ratner MA, Xu HQ, Nitzan A, Guo XF, Science, 352(6292), 1443 (2016)

[2] Rostya R, Kebbekusa B, Zaitsev V, Sens. Actuat. B, 107, 347 (2005)

[3] Zhizhchenko AY, Vitrik OB, Kulchin YN, Opt. Mater., 46, 265 (2015)

[4] Wu J, Lu XM, Yi ZY, Shan F, Lu QH, Macromolecules, 46(9), 3376 (2013)

[5] Fukukawa KI, Ueda M, Polym. J., 38, 405 (2006)

[6] Tang KC, Chang MJ, Lin TY, Pan HA, Fang TC, Chen KY, Hung WY, Hsu YH, Chou PT, J. Am. Chem. Soc., 133(44), 17738 (2011)

[7] Park S, Seo J, Kim SH, Park SY, Adv. Funct. Mater., 18(5), 726 (2008)

[8] Mutai T, Tomoda H, Ohkawa T, Yabe Y, Araki K, Angew. Chem.-Int. Edit., 47, 9522 (2008)

[9] Zhao J, Ji S, Chem Y, Guo H, Yang P, Phys. Chem. Chem. Phys., 14, 8803 (2012)

[10] Chung MW, Lin TY, Hsieh CC, Tang KC, Fu H, Chou PT, Yang SH, Chi Y, J. Phys. Chem. A, 114(30), 7886 (2010)

[11] Padalkar VS, Ramasami P, Sekar N, J. Fluoresc, 23, 8539 (2013)

[12] Tu Z, Liu M, Qian Y, Yang G, Cai M, Wang L, Huang W, RSC Adv., 5, 7789 (2015)

[13] Wang J, Qian X, Cui J, J. Org. Chem., 71, 4308 (2006)

[14] Wang JF, Chu QH, Liu XM, Wesdemiotis C, Pang Y, J. Phys. Chem. B, 117(15), 4127 (2013)

[15] Li C, Yang Y, Ma C, Liu Y, RSC Adv., 6, 5134 (2016)

[16] Syetov Y, J. Fluoresc., 23, 689 (2013)

[17] Lim SJ, Seo J, Park SY, J. Am. Chem. Soc., 128(45), 14542 (2006)

[18] Wei R, Song P, Tong A, J. Phys. Chem. C, 117, 3467 (2013)

[19] Qian Y, Li S, Wang Q, Sheng X, Wu S, Wang S, Li J, Yang G, Soft Matter, 8, 757 (2012)

[20] Park S, Kwon OH, Lee YS, Jang DJ, Park SY, J. Phys. Chem., 111, 9649 (2007)

[21] Chen WH, Xing Y, Pang Y, Org. Lett., 13, 1362 (2011)

[22] Wang J, Pang Y, RSC Adv., 4, 5845 (2014)

[23] Wang J, Li Y, Patel NG, Zhang G, Zhou D, Pang Y, Chem. Commun., 50, 12258 (2014)

[24] Lee MH, Kim JS, Sessler JL, Chem. Soc. Rev., 44, 4185 (2015)

[25] Lee JK, Kim HJ, Kim TH, Lee CH, Park WH, Kim J, Lee TS, Macromolecules, 38(23), 9427 (2005)

[26] Mizuno T, Wei WH, Eller LR, Sessler JL, J. Am. Chem. Soc., 124(7), 1134 (2002)

[27] Kulkarni AP, Zhu Y, Jenekhe SA, Macromolecules, 38(5), 1553 (2005)