Abstract
N-alkoxybenzyl aromatic polyamides were synthesized by polycondensation of N-alkoxybenzyl aromatic diamine with equimolar dicarboxylic acid chloride in the presence of 2.2 equiv. of pyridine at room temperature for 2 days. The obtained polyamides were mainly cyclic polymers, as determined by means of matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, and showed higher solubility in organic solvents than unprotected aromatic polyamides. Photodeprotection of N-alkoxybenzyl aromatic polyamide film containing photo acid generator (PAG) proceeded well under UV irradiation (5 J/cm2), followed by heating at 130 °C for 15 min. The nature of the polymer end groups of N-alkoxybenzyl aromatic polyamides was found to be crucial for photodeprotection reactivity. These polymers are promising candidates for photosensitive heat-resistant materials for fine Cu wiring formation by electroless Cu plating of high-density semiconductor packaging substrates.
Highlights
Electronic devices, such as mobile phones, tablets, and personal computers, are becoming dramatically smaller and more functionalized
We have developed film-type photosensitive heat-resistant materials for high-density packaging, such as phenolic-resin-based negative tone resist containing cross-linkers and photo acid generator (PAG), and these materials provide high resolution (10 μm via for 25 μm-thick film), high adhesion to Ti/Cu sputtering seed layer, and capability to fabricate Cu wiring of less than 5 μm [6]
We have demonstrated that highly soluble N-alkoxybenzyl aromatic polyamides can serve as photosensitive materials through photodeprotection of the alkoxybenzyl group with PAG, affording N-H polyamides with low solubility
Summary
Electronic devices, such as mobile phones, tablets, and personal computers, are becoming dramatically smaller and more functionalized. There is a continuing requirement for packaging structures for semiconductors to be made smaller and thinner, and further scaling-down of Cu wiring and vias in packaging substrates is needed [1]. Is currently a cutting-edge technology for Cu wiring and via formation in packaging substrate manufacturing. In this process, electroless Cu plating is applied to form patterned Cu wires on the substrate. To obtain fine Cu wiring below 5 μm, sputtering Ti/Cu has been investigated [2]. CO2 lasers have been used for via formation to non-photosensitive heat-resistant material, while
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