New positive-type photosensitive polyimide having sulfo groups

A new positive-working photosensitive polyimide (PSPI) has been developed, which is based on polyimide bearing sulfo groups (PIS) and 1-{1,1-bis[4-(2-diazo-1-(2H)naphthalenone-5-sulfonyloxy)phenyl]ethyl}-4-{1-[4-(2-diazo-1(2H)naphthalenone-5-sulfonyloxy)phenyl]methylethyl}benzene (S-DNQ) as a photosensitive compound. PIS was prepared by ring-opening polyaddition of 1,3-phenylenediamine-4-sulfonicacid (PDAS), 4,4′-oxydianiline (ODA), and 4,4′-hexafluoropropylidenebis(phthalic anhydride) (6FDA), followed by thermal cyclization in m-cresol. PIS containing 30 wt% of S-DNQ showed a sensitivity of 100 mJ cm−2 and a contrast of 1.7, when it was exposed to 365 nm light followed by developing with 2.38 wt% aqueous tetramethylammonium hydroxide (TMAH) solution at room temperature. A fine positive image featuring 10 μm line and space patterns was observed on the film of the photoresist exposed to 200 mJ cm−2 of UV-light at 365 nm by the contact mode. The positive image was successfully converted to the polyimide pattern by thermal treatment.