Polarizing Group Attached Acrylates and Polymers Viewing High Refractive Index

Ji Yun Kwon; Bong Gun Kim; Jung Yun Do; Jung-Jin Ju; Seung Koo Park

Macromolecular Research, Vol.15, No.6, 533-540, October, 2007

Export Citation

Polarizing Group Attached Acrylates and Polymers Viewing High Refractive Index

Ji Yun Kwon, Bong Gun Kim, Jung Yun Do^†, Jung-Jin Ju¹, and Seung Koo Park¹

Department of Advanced Materials for Information and Display, Pusan National University, Busan 609-735, Korea
¹Telecommunication Basic Research Laboratory, ETRI, Daejeon 305-350, Korea

E-mail:

We designed and successfully synthesized UV curable, functional acrylate monomers having a polarizing group, i.e., an electron-withdrawing and/or electron-donating group for the optical materials of high refractive index. Optical polymer films made from the functional methacrylate monomers were achieved with photo crosslinking under UV illumination. A monomer having amino and cyano groups (Dimer-CN) exhibited the highest refractive index (nTE = 1.595 at 850 nm) among the studied methacrylate derivatives, due to the large polarizability of the dipolar monomer structures with electron-donating and withdrawing groups. By controlling the compositions of the functional acrylate monomer of copolymers, the refractive indices of the polymers were readily adjusted within a wide range of 1.498-1.595. The copolymers showed a high glass transition temperature (Tg) and good thermal stability, which are desirable for optical applications. Tg and T10% (10%-weight loss occurred) of the copolymers ranged from 120-140 ℃ and from 329-387 ℃, respectively.

Keywords:high refractive index;dipolar methacrylates;UV curing;thermal stability

[References]

Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB, Nature, 347, 539 (1990)
Peng ZH, Gharavi AR, Yu LP, J. Am. Chem. Soc., 119(20), 4622 (1997)
Cui ZC, Lu CL, Yang B, Shen JC, Su XP, Yang H, Polymer, 42(26), 10095 (2001)
Shim H, Kim H, Ann T, Kang T, Zyung T, Synth. Met., 91, 289 (1997)
Ershadlangroudi A, Mai C, Vigier G, Vassoille R, J. Appl. Polym. Sci., 65(12), 2387 (1997)
Cho JD, Kim YB, Ju HT, Hong JW, Macromol. Res., 13(4), 362 (2005)
Kim TH, Chang JY, Choi JU, Kim WS, Macromol. Res., 13(6), 545 (2005)
Qi YH, Ding JF, Day M, Jiang J, Callender CL, Polymer, 47(25), 8263 (2006)
Otuska Y, Polymer Digest., 3, 2 (1986)
Assaid I, Bosc D, Hardy I, J. Phys. Chem. B, 108(9), 2801 (2004)
Yoo DW, Yang SJ, Lee JK, Park J, Char K, Macromol. Res., 14(1), 107 (2006)
Matsuda T, Funae Y, Yoshida M, Yamamoto T, Takaya T, J. Appl. Polym. Sci., 76(1), 45 (2000)
Matsuda T, Funae Y, Yoshida M, Yamamoto T, J. M. S-Pure Appl. Chem., A37, 239 (2000)
Liang J, Toussaere E, Hierle R, Levenson R, Zyss J, Ochs AV, Rousseau A, Boutevin B, Opt. Mater., 9, 230 (1998)
Yamada N, Yoshinaga I, Katayama S, J. Sol-Gel Sci. Technol., 17, 179 (2000)
Seferis JC, Refractive Indices of Polymers in Polymer Handbook, 4th ed., J. Brandrup, E. H. Immergut, and E. A. Grulke, Eds., Wiley, New York, 1999, VI, p 571
Ahlheim M, Barzoukas M, Bedworth PV, Blancharddesce M, Fort A, Hu ZY, Marder SR, Perry JW, Runser C, Staehelin M, Zysset B, Science, 271(5247), 335 (1996)
Pearson JM, Vinyl Carbazole Polymers in Encyclopedia of Polymer Science and Engineering, Wiley, New York, 1989, p 257
Arutunyan EA, Galoyan SK, Opt. Commun., 57, 391 (1986)
Davis TP, Gallagher MJ, Ranasinghe MG, Zammit MD, J. Mater. Chem., 4, 1359 (1994)
Boudroua A, Loulergue JC, Opt. Commun., 137, 37 (1997)
Zapf F, Markert H, Rogler W, Btapp B, Polym. Prepr, 30, 107 (1986)
Dekker M, Polymers for Lightwave and Integrated Optics, H. A. Hornak, Ed., New York, 1992, p 149
Simon GP, Allen PEM, Bennett DJ, Williams DRG, Williams EH, Macromolecules, 22, 3555 (1989)
Kannurpatti AR, Anderson KJ, Anseth JW, Bowman CN, J. Polym. Sci. B: Polym. Phys., 35(14), 2297 (1997)
Doyle CD, Anal. Chem., 33, 77 (1961)

[Referenced By]

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

[2] Peng ZH, Gharavi AR, Yu LP, J. Am. Chem. Soc., 119(20), 4622 (1997)

[3] Cui ZC, Lu CL, Yang B, Shen JC, Su XP, Yang H, Polymer, 42(26), 10095 (2001)

[4] Shim H, Kim H, Ann T, Kang T, Zyung T, Synth. Met., 91, 289 (1997)

[5] Ershadlangroudi A, Mai C, Vigier G, Vassoille R, J. Appl. Polym. Sci., 65(12), 2387 (1997)

[6] Cho JD, Kim YB, Ju HT, Hong JW, Macromol. Res., 13(4), 362 (2005)

[7] Kim TH, Chang JY, Choi JU, Kim WS, Macromol. Res., 13(6), 545 (2005)

[8] Qi YH, Ding JF, Day M, Jiang J, Callender CL, Polymer, 47(25), 8263 (2006)

[9] Otuska Y, Polymer Digest., 3, 2 (1986)

[10] Assaid I, Bosc D, Hardy I, J. Phys. Chem. B, 108(9), 2801 (2004)

[11] Yoo DW, Yang SJ, Lee JK, Park J, Char K, Macromol. Res., 14(1), 107 (2006)

[12] Matsuda T, Funae Y, Yoshida M, Yamamoto T, Takaya T, J. Appl. Polym. Sci., 76(1), 45 (2000)

[13] Matsuda T, Funae Y, Yoshida M, Yamamoto T, J. M. S-Pure Appl. Chem., A37, 239 (2000)

[14] Liang J, Toussaere E, Hierle R, Levenson R, Zyss J, Ochs AV, Rousseau A, Boutevin B, Opt. Mater., 9, 230 (1998)

[15] Yamada N, Yoshinaga I, Katayama S, J. Sol-Gel Sci. Technol., 17, 179 (2000)

[16] Seferis JC, Refractive Indices of Polymers in Polymer Handbook, 4th ed., J. Brandrup, E. H. Immergut, and E. A. Grulke, Eds., Wiley, New York, 1999, VI, p 571

[17] Ahlheim M, Barzoukas M, Bedworth PV, Blancharddesce M, Fort A, Hu ZY, Marder SR, Perry JW, Runser C, Staehelin M, Zysset B, Science, 271(5247), 335 (1996)

[18] Pearson JM, Vinyl Carbazole Polymers in Encyclopedia of Polymer Science and Engineering, Wiley, New York, 1989, p 257

[19] Arutunyan EA, Galoyan SK, Opt. Commun., 57, 391 (1986)

[20] Davis TP, Gallagher MJ, Ranasinghe MG, Zammit MD, J. Mater. Chem., 4, 1359 (1994)

[21] Boudroua A, Loulergue JC, Opt. Commun., 137, 37 (1997)

[22] Zapf F, Markert H, Rogler W, Btapp B, Polym. Prepr, 30, 107 (1986)

[23] Dekker M, Polymers for Lightwave and Integrated Optics, H. A. Hornak, Ed., New York, 1992, p 149

[24] Simon GP, Allen PEM, Bennett DJ, Williams DRG, Williams EH, Macromolecules, 22, 3555 (1989)

[25] Kannurpatti AR, Anderson KJ, Anseth JW, Bowman CN, J. Polym. Sci. B: Polym. Phys., 35(14), 2297 (1997)

[26] Doyle CD, Anal. Chem., 33, 77 (1961)