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Published in: Polymer Bulletin 3/2015

01-03-2015 | Original Paper

Synthesis of novel branched UV-curable methacrylate copolymer and its application in negative photoresist

Authors: Jingcheng Liu, Xiangfei Zheng, Hu Li, Ren Liu, Qidao Mu, Xiaoya Liu

Published in: Polymer Bulletin | Issue 3/2015

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Abstract

A series of novel branched methacrylate copolymers (BPMBMV) were synthesized via the mercapto chain transfer polymerization using methacrylic acid, maleic anhydride, benzyl methacrylate, and 4-vinyl benzyl thiol. Then, BPMBMV reacted with hydroxyethyl acrylate to obtain branched UV-curable copolymer H-BPMBMV, which were characterized by fourier transfer infrared spectra and proton nuclear magnetic resonance spectra. The molecular weights and glass transition temperature (T g ) of the polymers decreased with the addition of VBT. The results of photo-differential scanning calorimetry (Photo-DSC) tests showed that photo-polymerization ability of H-BPMBMV increased with the increased content of VBT. With an optimized formulation, a negative-type photoresist was prepared. The resolution of the circuit could reach as high as 20 μm, and the film of photoresist showed good acid resistance.

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Literature
1.
go back to reference Guo L, DeWeerth SP (2010) High-density stretchable electronics: toward an integrated multilayer composite. Adv Mater 22:4030–4033CrossRef Guo L, DeWeerth SP (2010) High-density stretchable electronics: toward an integrated multilayer composite. Adv Mater 22:4030–4033CrossRef
2.
go back to reference Lee CK, Hwang FH, Cheng LP et al (2012) Preparation and characterization of nanosilica-filled color resist. Adv Polym Technol 31(2):163–171CrossRef Lee CK, Hwang FH, Cheng LP et al (2012) Preparation and characterization of nanosilica-filled color resist. Adv Polym Technol 31(2):163–171CrossRef
3.
go back to reference Sakii D, Takahashi A, Oyama T (2012) Development of photosensitive vinyl polymers with imide group based on reaction development patterning. J Photopolym Sci Technol 25:371–374CrossRef Sakii D, Takahashi A, Oyama T (2012) Development of photosensitive vinyl polymers with imide group based on reaction development patterning. J Photopolym Sci Technol 25:371–374CrossRef
4.
go back to reference Eunhye K, Hyungju A, Sungmin P (2013) Directed assembly of high molecular weight block copolymers: highly ordered line patterns of perpendicularly oriented lamellae with large periods. ACS Nano 7(3):1952–1960CrossRef Eunhye K, Hyungju A, Sungmin P (2013) Directed assembly of high molecular weight block copolymers: highly ordered line patterns of perpendicularly oriented lamellae with large periods. ACS Nano 7(3):1952–1960CrossRef
5.
go back to reference Li TS, Xu WJ, Tang CQ (2012) Controllable photopatterning and photochemical properties of novel copolymer containing dianthracene Langmuir–Blodgett films. J Polym Sci Part B Polym Phys 50:139–147CrossRef Li TS, Xu WJ, Tang CQ (2012) Controllable photopatterning and photochemical properties of novel copolymer containing dianthracene Langmuir–Blodgett films. J Polym Sci Part B Polym Phys 50:139–147CrossRef
6.
go back to reference Han WS, Lin BP, Yang H et al (2012) Synthesis and properties of UV-curable hyperbranched polyurethane acrylate oligomers containing carboxyl groups. Polym Bull 68:1009–1022CrossRef Han WS, Lin BP, Yang H et al (2012) Synthesis and properties of UV-curable hyperbranched polyurethane acrylate oligomers containing carboxyl groups. Polym Bull 68:1009–1022CrossRef
7.
go back to reference Lee CK, Don TM, Lin DJ et al (2008) Characterization of acrylic copolymers applied in negative-type photoresist via a ternary composition diagram. J Appl Polym Sci 109:467–474CrossRef Lee CK, Don TM, Lin DJ et al (2008) Characterization of acrylic copolymers applied in negative-type photoresist via a ternary composition diagram. J Appl Polym Sci 109:467–474CrossRef
8.
go back to reference Shi J, Jim CKW, Mahtab F et al (2010) Ferrocene-functionalized hyperbranched polyphenylenes: synthesis, redox activity, light refraction, transition-metal complexation, and precursors to magnetic ceramics. Macromolecules 43:680–690CrossRef Shi J, Jim CKW, Mahtab F et al (2010) Ferrocene-functionalized hyperbranched polyphenylenes: synthesis, redox activity, light refraction, transition-metal complexation, and precursors to magnetic ceramics. Macromolecules 43:680–690CrossRef
9.
go back to reference Tang Y, Jim CKW, Liu Y, Ye L et al (2010) Synthesis and curing of hyperbranched poly(triazole)s with click polymerization for improved adhesion strength. ACS Appl Mater Interfaces 2:566–574CrossRef Tang Y, Jim CKW, Liu Y, Ye L et al (2010) Synthesis and curing of hyperbranched poly(triazole)s with click polymerization for improved adhesion strength. ACS Appl Mater Interfaces 2:566–574CrossRef
10.
go back to reference Go C, Yan D (2004) Hyperbranched polymers: from synthesis to applications. Prog Polym Sci 29:183–275CrossRef Go C, Yan D (2004) Hyperbranched polymers: from synthesis to applications. Prog Polym Sci 29:183–275CrossRef
11.
go back to reference Liu CW, Zhao XG (2013) Synthesis of soluble and autophotosensitive hyperbranched polyimides with good optical properties and thermal properties. Polym J 45:318–325CrossRef Liu CW, Zhao XG (2013) Synthesis of soluble and autophotosensitive hyperbranched polyimides with good optical properties and thermal properties. Polym J 45:318–325CrossRef
12.
go back to reference Christos L, Georges H (2009) Hyperbranched polymers for photolithographic applications—towards understanding the relationship between chemical structure of polymer resin and lithographic performances. Adv Mater 21:1121–1125CrossRef Christos L, Georges H (2009) Hyperbranched polymers for photolithographic applications—towards understanding the relationship between chemical structure of polymer resin and lithographic performances. Adv Mater 21:1121–1125CrossRef
13.
go back to reference Hae SS, Jong CL (2012) Preparation of acid-cleavable branched polymers for argon fluoride photoresists via reversible addition-fragmentation chain-transfer polymerization. J Appl Polym Sci 125(1):344–352CrossRef Hae SS, Jong CL (2012) Preparation of acid-cleavable branched polymers for argon fluoride photoresists via reversible addition-fragmentation chain-transfer polymerization. J Appl Polym Sci 125(1):344–352CrossRef
14.
go back to reference Saptarshi C SR (2013) A novel photodegradable hyperbranched polymeric photoresist. Chem Commun 49:11041–11043CrossRef Saptarshi C SR (2013) A novel photodegradable hyperbranched polymeric photoresist. Chem Commun 49:11041–11043CrossRef
15.
go back to reference Isaure F, Cormack PAG, Sherrington DC (2004) Synthesis of branched poly (methyl methacrylate)s: effect of the branching comonomer structure. Macromolecules 37:2096–2105CrossRef Isaure F, Cormack PAG, Sherrington DC (2004) Synthesis of branched poly (methyl methacrylate)s: effect of the branching comonomer structure. Macromolecules 37:2096–2105CrossRef
16.
go back to reference Graham S, Cormack PAG, Sherrington DC (2005) One-pot synthesis of branched poly(methacrylic acid)s and suppression of the rheological “polyelectrolyte effect”. Macromolecules 38:86–90CrossRef Graham S, Cormack PAG, Sherrington DC (2005) One-pot synthesis of branched poly(methacrylic acid)s and suppression of the rheological polyelectrolyte effect. Macromolecules 38:86–90CrossRef
17.
go back to reference Baudry R, Sherrington DC (2006) Facile synthesis of branched poly(vinyl alcohol)s. Macromolecules 39:5230–5237CrossRef Baudry R, Sherrington DC (2006) Facile synthesis of branched poly(vinyl alcohol)s. Macromolecules 39:5230–5237CrossRef
18.
go back to reference Liu J, Wang Y, Fu Q (2008) Branched polymer via free radical polymerization of chain transfer monomer: a theoretical and experimental investigation. J Polym Sci Part A Polym Chem 46:1449–1459CrossRef Liu J, Wang Y, Fu Q (2008) Branched polymer via free radical polymerization of chain transfer monomer: a theoretical and experimental investigation. J Polym Sci Part A Polym Chem 46:1449–1459CrossRef
19.
go back to reference Jiang L, Huang WY, Xue XQ et al (2012) Radical polymerization in the presence of chain transfer monomer: an approach to branched vinyl polymers. Macromolecules 45:4092–4100CrossRef Jiang L, Huang WY, Xue XQ et al (2012) Radical polymerization in the presence of chain transfer monomer: an approach to branched vinyl polymers. Macromolecules 45:4092–4100CrossRef
20.
go back to reference Liu JC, Liu XY (2013) One-pot synthesis of branched alternating copolymers P(St-alt-MAn) via free radical polymerization in the presence of chain transfer monomer. Polym Bull 70:1795–1803CrossRef Liu JC, Liu XY (2013) One-pot synthesis of branched alternating copolymers P(St-alt-MAn) via free radical polymerization in the presence of chain transfer monomer. Polym Bull 70:1795–1803CrossRef
21.
go back to reference Liu JC, Liu R, Yuan Y et al (2013) Preparation of superhydrophobic antistatic coatings from branched alternating copolymers P(St-alt-MAn) and carbon nanotubes based on organic–inorganic hybrid approach. Prog Org Coat 76:1251–1257CrossRef Liu JC, Liu R, Yuan Y et al (2013) Preparation of superhydrophobic antistatic coatings from branched alternating copolymers P(St-alt-MAn) and carbon nanotubes based on organic–inorganic hybrid approach. Prog Org Coat 76:1251–1257CrossRef
22.
go back to reference Liu JC, Jia XL, Liu R et al (2014) Synthesis of UV-curable hyperbranched polyurethane and its application in the negative-type photoresist. J Wuhan Univ Technol (Mater Sci Ed) 29(1):208–212CrossRef Liu JC, Jia XL, Liu R et al (2014) Synthesis of UV-curable hyperbranched polyurethane and its application in the negative-type photoresist. J Wuhan Univ Technol (Mater Sci Ed) 29(1):208–212CrossRef
23.
go back to reference Ma R, Ma RM, Feng LL et al (2009) The synthesis of P(MAn-co-St)-b-PS-b-P(MAn-co-St) block copolymers by RAFT polymerization and the nanostructure of their self-assembly aggregates. Colloids Surf A Physicochem Eng Aspects 346:184–194CrossRef Ma R, Ma RM, Feng LL et al (2009) The synthesis of P(MAn-co-St)-b-PS-b-P(MAn-co-St) block copolymers by RAFT polymerization and the nanostructure of their self-assembly aggregates. Colloids Surf A Physicochem Eng Aspects 346:184–194CrossRef
24.
go back to reference Carola EC, Giulio M et al (2009) Mariaenrica Frigione UV-curable epoxy systems containing hyperbranched polymers: kinetics investigation by photo-DSC and real-time FT-IR experiments. Polym Test 28:157–164CrossRef Carola EC, Giulio M et al (2009) Mariaenrica Frigione UV-curable epoxy systems containing hyperbranched polymers: kinetics investigation by photo-DSC and real-time FT-IR experiments. Polym Test 28:157–164CrossRef
25.
go back to reference Yuan Y, Chen N, Liu R et al (2014) A novel acrylic prepolymer/methacrylate modified nano-SiO2 composite used for negative photoresist. Mater Res Bull 50:392–398CrossRef Yuan Y, Chen N, Liu R et al (2014) A novel acrylic prepolymer/methacrylate modified nano-SiO2 composite used for negative photoresist. Mater Res Bull 50:392–398CrossRef
Metadata
Title
Synthesis of novel branched UV-curable methacrylate copolymer and its application in negative photoresist
Authors
Jingcheng Liu
Xiangfei Zheng
Hu Li
Ren Liu
Qidao Mu
Xiaoya Liu
Publication date
01-03-2015
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 3/2015
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-014-1289-9

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