Novel Positive Working Photosensitive Polyimide-Carbon Black (PSPI-CB) Composites Containing Triphenylene Vinyl Ether (TP-VE) Monomers

Sun Jung Do; Young-Beom Seo; Yun Ho Kim; Jong Chan Won; Yu-Mi Ha; Jinsoo Kim

Macromolecular Research, Vol.29, No.2, 164-171, February, 2021

DOI10.1007/s13233-021-9021-8 Export Citation

Novel Positive Working Photosensitive Polyimide-Carbon Black (PSPI-CB) Composites Containing Triphenylene Vinyl Ether (TP-VE) Monomers

Sun Jung Do¹, Young-Beom Seo¹, Yun Ho Kim^{1, 2}, Jong Chan Won^{1, 2}, Yu-Mi Ha¹, and Jinsoo Kim^{1, †}

¹Advanced Materials Division, Korea Research Institute of Chemical Technology (KRICT), Daejeon 34114, Korea
²Chemical Convergence Materials and Processes, KRICT School, University of Science and Technology (UST), Daejeon 34113, Korea

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The first positive working chemically amplified photosensitive polyimidecarbon black (PSPI-CB) composite with 2,2'-bis(4-(2'-(vinyloxy)ethoxy)phenyl)propane (BPA-DEVE) as a crosslinking agent was prepared. In addition, the triphenylene vinyl ether (TP-VE) monomers 2,3-di-[(2-vinyloxy)ethoxy]triphenylene (TP-DEVE) and 2,3,6,7,10,11-hexa-[(2-vinyloxy)ethoxy]triphenylene (TP-HEVE) were used as novel CB dispersing aids as well as crosslinking agents. The photolithographic performance of TP-DEVE and TP-HEVE as crosslinking agents in the positive working PSPI and PSPI-CB composites was similar to that of BPA-DEVE. The CB dispersion ability of the crosslinking agents used in the present study was evaluated on the basis of the shading ability (optical density) and surface roughness of the PSPI-CB films. Given the same amount of crosslinking agent in the formulation of the PSP -CB composite, the optical density and surface roughness of the corresponding PSPI-CB composite film were 1.4 and 116.0 nm for PSPI-CB-1 with BPA-DEVE, 1.7 and 78.2 nm for PSPI-CB-2 with TP-DEVE, and 1.9 and 58.4 nm for PSPI-CB-3 with TP-HEVE, respectively. The results confirm that the CB dispersion ability of these crosslinking agents decreases in the order TP-HEVE > TP-DEVE > BPA-DEVE.

Keywords:photosensitive polyimide-carbon black (PSPI-CB) composite;triphenylene vinyl ether (TP-VE) monomer;crosslinking agent;carbon black (CB) dispersing aid;π-π interaction

[References]

Kuo KH, Chiu WY, Hsieh KH, Don TM, Eur. Polym. J., 45, 474 (2009)
Kudo T, Nozaki Y, Nanjo Y, Yamaguchi H, Nagao K, Okazaki H, Pawlowski G, J. Photopolym Sci. Technol., 9, 121 (1996)
Bui TS, Kim J, Jung E, Le HS, Nguyen NT, Bae JY, Displays, 34, 192 (2013)
Koo HS, Chen M, Kawai T, Diam. Relat. Mater., 18, 533 (2009)
Lee BD, Cho YH, Oh MH, Lee SY, Lee SY, Lee JH, Zang DS, Mater. Chem. Phys., 112(3), 734 (2008)
Shi G, Park SH, Kim J, Kim M, Park LS, Int. J. Polym. Sci., 2018, Article ID 3790834 (2018).
Shi G, Park JW, Park LS, Mater. Sci. Appl., 9, 554 (2018)
Fukukawa KI, Ueda M, Polym. J., 40, 281 (2008)
Mochizuki A, Ueda M, J. Photopolym. Sci. Technol., 14, 677 (2001)
Omote T, Koseki K, Yamaoka T, Macromolecules, 23, 4788 (1990)
Jung MS, Hyeon-Lee J, Choi TL, J. Appl. Polym. Sci., 107(4), 2632 (2008)
Nakano T, Iwasa H, Miyagawa N, Takahara S, Yamaoka T, J. Photopolym Sci. Technol., 13, 715 (2000)
Okazaki M, Onishi H, Yamashita W, Tamai S, J. Photopolym Sci. Technol., 19, 277 (2006)
Reichmanis E, Houlihan F, Nalamasu O, Neenan T, Adv. Mater. Opt. Electron., 4, 83 (1994)
Malval JP, Morlet-Savary F, Allonas X, Fouassier JP, Suzuki S, Takahara S, Yamaoka T, Chem. Phys. Lett., 443(4-6), 323 (2007)
Liu CY, Cheng WT, Surf. Interface Anal., 51, 316 (2019)
Belmont JA, Moeser GD, Korchev A, Kyrlidis A, Huffman JK, U.S. Patent No. 8,501,148 (2013).
Charles RH, Combs ZA, Tunnicliffe LB, U.S. Patent Application No. 16/763,741 (2020).
Kawasaki S, Takada T, Jin F, in Metal, Ceramic and Polymeric Composites for Various Uses, IntechOpen, 2011.
Kamegawa K, Nishikubo K, Yoshida H, Carbon, 36, 433 (1998)
Yang Q, Wang L, Xiang WD, Zhou JF, Li JH, Polymer, 48(10), 2866 (2007)
Tiarks F, Landfester K, Antonietti M, Macromol. Chem. Phys., 202, 51 (2001)
Kyrlidis A, Xiong K, Sullivan X, Szwec J, Step E, 12th International Display Workshops in Conjunction with Asia Display, 2005.
Wu G, Tang Y, Weng R, Polym. Degrad. Stabil., 95, 1449 (2010)
Romyen N, Thongyai S, Praserthdam P, J. Appl. Polym. Sci., 115(3), 1622 (2010)
Lin YN, Smith TW, Alexandridis P, J. Colloid Interface Sci., 255(1), 1 (2002)
Gallucci R, Going R, J. Org. Chem., 48, 342 (1983)
Shimizu Y, et al., Liquid Crystals IX, nternational Society for Optics and Photonics, Vol. 5936, P59360M 2005.
Reynes M, Dautel OJ, Virieux D, Flot D, Moreau JJ, CrystEng-Comm, 13, 6050 (2011)
Noppakundilograt S, Miyagawa N, Takahara S, Yamaoka T, J. Photopolym Sci. Technol., 12, 773 (1999)
Moon SY, Chung CM, Yamaoka T, Polymer, 41(11), 4013 (2000)
Moon S, Yamaoka T, Polym. Adv. Technol., 6, 566 (1995)
Moon SY, J. Appl. Polym. Sci., 81(14), 3399 (2001)
Yamaoka T, Suzuki T, Yamashita Y, J. Photopolym Sci. Technol., 8, 665 (1995)
Yamamoto T, Motoyanagi J, Murakami Y, Miyauchi Y, Maruyama S, Kato M, Appl. Phys. Express, 2, 055501 (2009)

[1] Kuo KH, Chiu WY, Hsieh KH, Don TM, Eur. Polym. J., 45, 474 (2009)

[2] Kudo T, Nozaki Y, Nanjo Y, Yamaguchi H, Nagao K, Okazaki H, Pawlowski G, J. Photopolym Sci. Technol., 9, 121 (1996)

[3] Bui TS, Kim J, Jung E, Le HS, Nguyen NT, Bae JY, Displays, 34, 192 (2013)

[4] Koo HS, Chen M, Kawai T, Diam. Relat. Mater., 18, 533 (2009)

[5] Lee BD, Cho YH, Oh MH, Lee SY, Lee SY, Lee JH, Zang DS, Mater. Chem. Phys., 112(3), 734 (2008)

[6] Shi G, Park SH, Kim J, Kim M, Park LS, Int. J. Polym. Sci., 2018, Article ID 3790834 (2018).

[7] Shi G, Park JW, Park LS, Mater. Sci. Appl., 9, 554 (2018)

[8] Fukukawa KI, Ueda M, Polym. J., 40, 281 (2008)

[9] Mochizuki A, Ueda M, J. Photopolym. Sci. Technol., 14, 677 (2001)

[10] Omote T, Koseki K, Yamaoka T, Macromolecules, 23, 4788 (1990)

[11] Jung MS, Hyeon-Lee J, Choi TL, J. Appl. Polym. Sci., 107(4), 2632 (2008)

[12] Nakano T, Iwasa H, Miyagawa N, Takahara S, Yamaoka T, J. Photopolym Sci. Technol., 13, 715 (2000)

[13] Okazaki M, Onishi H, Yamashita W, Tamai S, J. Photopolym Sci. Technol., 19, 277 (2006)

[14] Reichmanis E, Houlihan F, Nalamasu O, Neenan T, Adv. Mater. Opt. Electron., 4, 83 (1994)

[15] Malval JP, Morlet-Savary F, Allonas X, Fouassier JP, Suzuki S, Takahara S, Yamaoka T, Chem. Phys. Lett., 443(4-6), 323 (2007)

[16] Liu CY, Cheng WT, Surf. Interface Anal., 51, 316 (2019)

[17] Belmont JA, Moeser GD, Korchev A, Kyrlidis A, Huffman JK, U.S. Patent No. 8,501,148 (2013).

[18] Charles RH, Combs ZA, Tunnicliffe LB, U.S. Patent Application No. 16/763,741 (2020).

[19] Kawasaki S, Takada T, Jin F, in Metal, Ceramic and Polymeric Composites for Various Uses, IntechOpen, 2011.

[20] Kamegawa K, Nishikubo K, Yoshida H, Carbon, 36, 433 (1998)

[21] Yang Q, Wang L, Xiang WD, Zhou JF, Li JH, Polymer, 48(10), 2866 (2007)

[22] Tiarks F, Landfester K, Antonietti M, Macromol. Chem. Phys., 202, 51 (2001)

[23] Kyrlidis A, Xiong K, Sullivan X, Szwec J, Step E, 12th International Display Workshops in Conjunction with Asia Display, 2005.

[24] Wu G, Tang Y, Weng R, Polym. Degrad. Stabil., 95, 1449 (2010)

[25] Romyen N, Thongyai S, Praserthdam P, J. Appl. Polym. Sci., 115(3), 1622 (2010)

[26] Lin YN, Smith TW, Alexandridis P, J. Colloid Interface Sci., 255(1), 1 (2002)

[27] Gallucci R, Going R, J. Org. Chem., 48, 342 (1983)

[28] Shimizu Y, et al., Liquid Crystals IX, nternational Society for Optics and Photonics, Vol. 5936, P59360M 2005.

[29] Reynes M, Dautel OJ, Virieux D, Flot D, Moreau JJ, CrystEng-Comm, 13, 6050 (2011)

[30] Noppakundilograt S, Miyagawa N, Takahara S, Yamaoka T, J. Photopolym Sci. Technol., 12, 773 (1999)

[31] Moon SY, Chung CM, Yamaoka T, Polymer, 41(11), 4013 (2000)

[32] Moon S, Yamaoka T, Polym. Adv. Technol., 6, 566 (1995)

[33] Moon SY, J. Appl. Polym. Sci., 81(14), 3399 (2001)

[34] Yamaoka T, Suzuki T, Yamashita Y, J. Photopolym Sci. Technol., 8, 665 (1995)

[35] Yamamoto T, Motoyanagi J, Murakami Y, Miyauchi Y, Maruyama S, Kato M, Appl. Phys. Express, 2, 055501 (2009)