Calixarene and Dendrimer as Novel Photoresist Materials

Abstract

Negative-working alkaline developable photoresists based on calix[4]-resorcinarene (1) or calixarene dendrimer (2), a cross linker, and a photo acid generator have been developed. Compound 2 was prepared by the condensation of compound 1 with 3,5-diallyloxybenzylbromide, followed by the removal of allyl groups. The resist consisting of 1 (70wt%), a photo-acid generator, diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS) (10wt%), and 4,4-methylenebis[2,6-bis(hydroxymethyl)-phenol] (MBHP) (20wt%) as a cross-linker showed a sensitivity of 2.2 mJ·cm-2 and a contrast of 3.1 when it was exposed to 365 nm light and postbaked at 130 °C for 3 min, followed by developing with a 0.1% aqueous tetramethylammonium hydroxide (TMAH) solution. On the other hand, the resist formulated by mixing 2 (70wt%), DIAS (10wt%), and the cross-linker, 2,6-bis(hydroxymethyl)phenol (BHP) produced a clear negative patternes by the exposure of 365 nm (10 mJ·cm-2) UV light, postbaked at 110 °C for 3 min, and developed with a 0.3% TMAH aqueous solution.