Abstract
A new negative-working and alkaline-developable photosensitive polyimide precursor based on semi-aromatic poly(amic acid)s (4), 4,4′-methylenebis[2,6-bis(hydroxymethyl)]phenol (MBHP) as a cross-linker, and a photoacid generator (5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-2-(methylphenyl)acetonitrile (PTMA) has been developed. Novel polymers 4 were prepared by ring-opening polyadditions of alicyclic dianhydrides (1), 1,2,3,4-cyclobutanetetracarboxylic dianhydride (1a), bicyclo[2.2.2]oct-7-ene-2,3;5,6-tetracarboxylic dianhydride (1b), and bicyclo[2.2.1]heptane-2-methanecarboxylic-3,5,6-tricarboxylic-2,3:5,6-dianhydride (1c) with 1,3-bis(4-aminophenoxy)adamantane (3). Polymers 4 were converted to corresponding poly(imide)s (5) by thermal treatment. The dielectric constants (ε) of 5 estimated from the refractive indices were 2.72–2.74. The photosensitive polyimide precursor containing 4 (60 wt %), MBHP (30 wt %), and PTMA (10 wt %) cast from 2-methoxyethanol solution showed a clear negative image featuring 15 μm line and space patterns when it was exposed to 436 nm light, post-exposure baked at 110 °C for 3 min, followed by developing with 2.38 wt % aqueous tetramethylammonium hydroxide (TMAH) solution at 25 °C for 40 s.
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Watanabe, Y., Shibasaki, Y., Ando, S. et al. New Negative-type Photosensitive Alkaline-developable Semi-aromatic Polyimides with Low Dielectric Constants Based on Poly(amic acid) from Aromatic Diamine Containing Adamantyl Units and Alicyclic Dianhydrides, A Cross-linker, and A Photoacid Generator. Polym J 37, 270–276 (2005). https://doi.org/10.1295/polymj.37.270
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DOI: https://doi.org/10.1295/polymj.37.270
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