Synthesis of New Polymers for Photoresist and Lithographic Printing Applications

J of Applied Polymer Sci

Sadik

2010

Negative photoresists are materials that become insoluble in developing solution when exposed to optical radiation. This work describes the production of simple negative-working resists, demonstrating aqueous development, for potential printing plate applications. The copolymers comprised glycidyl methacrylate (GMA) and acrylic acid (AA) via free-radical solution polymerization in methyl ethyl ketone as a solvent using azobisisobutyronitrile as initiator at 60 C. Characterization of the copolymers prepared was carried out via IR, 1 H-NMR, and thermal analysis techniques. The copolymers of GMA/AA were successfully prepared over a wide range of composition. It was found that the copolymer containing 15 mol % of AA unit in the feed was developed with NaOH on copper plate rather than zinc plate and crosslinked in the presence of photogenerated acid (PAG) caused by acid-initiated ring-opening polymerization of pendant epoxide groups. Exposure of the resist films to UV radiation at k max ¼ 365 nm results in the generation of acid, and the subsequent baking process at 80 C for 1 min promotes the diffusion of the PAG, which initiates the cationic crosslinking of the epoxide rings.

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

New aqueous base developable photoresist for lithographic printing plates applications

J of Applied Polymer Sci

Sadik

2010

“…[15][16][17] The high reactivity of the epoxide group is due to the considerable strain in the three-membered ring. The MAA monomer was chosen to provide water solubility.…”

Section: Poly(gma/maa/t-bocvp) Terpolymersmentioning

confidence: 99%

Preparation, characterization, and lithographic applications of glycidyl methacrylate/methacrylic acid/t‐butyl‐4‐vinylphenyl carbonate terpolymers

J of Applied Polymer Sci

Sadik

El‐Maghraby

2008

At present, most negative working lithographic plates use organic solvents as a developing medium. These developers have the obvious disadvantages of toxicity, fire risk, and are more expensive than the aqueous developers. This work describes the synthesis and characterization of materials that have similar photoactive properties to existing materials, but are soluble in water or aqueous medium rather than organic solvents. These materials are terpolymers comprising of one sort of material to induce water solubility, such as methacrylic acid (MAA) and another material to give the photoactive response such as glycidyl methacrylate (GMA). The tertiary-butyl-4-vinyl phenyl carbonate (t-BOCVP) was added as a chemically amplifying agent. Various terpolymers were prepared via free-radical solution polymerization, typically in methyl ethyl ketone (MEK). Crosslinking reaction was induced using mixed arylsulphonium hexafluoroantimonate (MAS1 -SbF À 6 ) as a photogenerating acid. It was found that the films of the terpolymer containing 85 mol % of GMA unit with the addition of 5 mol % rather than 2 mol % of the t-BOCVP in the feed ratio gave good acid resistance and good adhesion to the surface of the zinc plate.

“…This reaction was explored further by Crivello who named these mixtures mixed aryl sulphonium (MAS) salts [10]. Further study has suggested that these mixtures contain more than 12 UV-absorbing components, which may play a part in the photoproduction of acidic species [11] The (MAS 3 -SbF 4 6 ) salt was made in a good yield as a white powder. The characteristic data for this material is presented in table 3.…”

Section: Synthesis and Evaluation Of Acrylate Copolymers 447mentioning

confidence: 99%

Synthesis and Characterization of Some Acrylate Copolymers and their Evaluation as Aqueous Developable Photoresists

High Performance Polymers

Abdel-Alim

Ahmed

2007

In the recent past, it has been found that the use of onium salts as acid-generating species has improved the performance of photoresists, particularly for microelectronic applications. However, little research has been dedicated to the use of these photo-initiators in aqueous-developable resists. This work describes the synthesis and characterization of some water-soluble polymers and investigates the feasibility of employing one of the onium salts in the formulation of a resist polymer for use in aqueous conditions. The ability of this onium salt to photo-initiate the cationic polymerization of epoxies residues was exploited using water-soluble copolymers, containing glycidyl methacrylate (GMA). The comonomers included methacrylic acid. Various copolymers were prepared by radical copolymerization typically in methyl ethyl ketone. It was found that the copolymer containing 85 mol.% of GMA unit in feed was soluble in aqueous base and crosslinked in the presence of photogenerated acid caused by acid-initiated ring opening polymerization of the pendant epoxide groups. A good pattern with reasonable resolution was attained by exposure to a UV lamp with λ = 365 nm light followed by a post exposure bake at 80° C for 1 min.