Esters of 1-oxo-2-diazo-naphthalene sulfonic acid wherein the sulfonic acid group is at either the 4 or the 5 position of a hydroxymethyl-tricyclo [5.2.1.0.sup.2,6 ] decane wherein the hydroxy group is either at the 3 or 4 position and useful as sensitizers for positive resists, particularly relatively thick resists at 365 nm.
A photosensitive polymer, a dissolution inhibitor, and a chemically amplified photoresist composition containing the photosensitive polymer and the dissolution inhibitor are provided. The photosensitive polymer is a copolymer polymerized with 5-norbornene-2-methanol derivative monomer having a C.sub.1 to C.sub.20 aliphatic hydrocarbon as a side chain, and a maleic anhydride monomer. The dissolution inhibitor is a tricyclodecane derivative or a sarsasapogenin derivative, each having an acid-labile group as a functional group. The chemically amplified photoresist composition containing the photosensitive polymer and/or dissolution inhibitor has a strong resistance to etching and excellent adherence to underlying layer.
A finely structurable resist system for a dry development process is provided. A latent image is produced in a light-sensitive layer by imaging exposure and is intensified by treatment with, for example, an organosilicon compound. The etching resistance to an oxygen plasma is simultaneously increased. The light-sensitive layer preferably comprises anhydride or epoxy groups that are suitable for reaction with the functional groups of the organosilicon compounds. A silylizing treatment can be implemented with a solution or emulsion in a simple apparatus or can be implemented in the vapor phase.
Photosensitizers containing saturated and unsaturated polycyclic compounds containing the cyclopentane-2-diazo-1,3-dione structural unit. These compounds have their maximum u.v. absorption at around 248 nm, decompose into polar products upon irradiation, and can be used as photosensitizers in positive deep u.v. or excimer laser (248 nm) lithography. They are most preferably useful with deep u.v. transparent resins for forming photoresists.
Photosensitizers containing saturated and unsaturated polycyclic compounds containing the cyclopentane-2-diazo-1,3-dione structural unit. These compounds have their maximum u.v. absorption at around 248 nm, decompose into polar products upon irradiation, and can be used as photosensitizers in positive deep u.v. or excimer laser (248 nm) lithography. They are most preferably useful with deep u.v. transparent resins for forming photoresists.
A novel process for preparing sulfonic acid esters and amides of benzo-heterocyclic diazo diketo compounds, such as substituted diazo-4-oxo-3,4-dihydrocoumarins, which are useful synthetic intermediates in a wide variety of applications including photoresists, opto-electronics, agricultural, and pharmaceutical applications is disclosed and claimed. The process comprises the steps of (a) subjecting a substituted benzo-heterocyclic .beta.-keto-enol compound to suitable diazo transfer conditions in the presence of a diazo transfer agent; (b) subjecting the so formed diazo diketo compound to suitable halosulfonation conditions in the presence of a halosulfonation agent; and (c) subjecting the so formed halosulfonyl aromatic compound to suitable substitution reaction in the presence of an alcohol or an amine to form the corresponding sulfonic acid ester or amide of benzo-heterocyclic diazo diketo compound. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
