Abstract
A novel poly(o-hydroxyamide) (PHA) as a precursor of photosensitive polybenzoxazole (PSPBO) that exhibits high transparency at 365 nm wavelength (i-line) has been developed. Time-dependent density functional theory (TD-DFT) calculations using the B3LYP hybrid functional were performed to predict the transparencies of various o-hydroxyamides in the i-line region. Based on these results, 2,2′-dimethyl-biphenyl-3,3′-dicarboxylic acid chloride was prepared and polymerized with 4,4′-(hexafluoroisopropylidene)bis(o-aminophenol). The resulting PHA-3 showed a high transparency (92%, 1.0×10−3 mol/L in N,N-dimethylacetamide (DMAc)), superior to that of the conventional PHA-1 (83% at the same concentration in DMAc) derived from 4,4′-oxybis(benzoyl chloride) in transparency. The positive-type PSPBO was then formulated based on PHA-3 with a cross-linker 1,3,5-tris[(2-vinyloxy)ethoxy]benzene (TVEB) and a photoacid generator (5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-2-(methylphenyl)acetonitrile (PTMA), and the resulting polymer film (1.5 μm-thick) demonstrated the high photosensitivity and contrast of 32 mJ/cm2 and 7.2, respectively. A clear positive image featuring 6 μm line-and-space was obtained, when a 6.0 μm-PSPBO film containing PHA-3, TVEB, and PTMA (15:3:2 in weight ratio) was exposed to i-line at 80 mJ/cm2, post-baked at 120 °C for 5 min, developed with an alkaline tetramethylammonium hydroxide solution. The positive image was converted to the corresponding polybenzoxazole pattern upon heating at 350 °C.
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Shibasaki, Y., Toyokawa, F., Ando, S. et al. Highly Transparent Photosensitive Polybenzoxazole: Poly(o-hydroxy amide) Derived from 4,4′-(Hexafluoroisopropylidene)bis(o-aminophenol) and o-Substituted Dicarboxylic Acid Chlorides. Polym J 39, 81–89 (2007). https://doi.org/10.1295/polymj.PJ2006114
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DOI: https://doi.org/10.1295/polymj.PJ2006114
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