Preliminary Evaluation of Copolymers of Methyl Methacrylate and Acyloximino Methacrylate as Deep U.V. Resists

Abstract

Copolymers of methyl methacrylate and acyloximino methacrylate esters have been evaluated as deep u.v. (200–250 nm) resists. Poly (methyl methacrylate‐co‐3‐methacryloyl‐oximino‐2‐butanone) has been found to be ∼5 times faster than PMMA at λ>240 normalnm and capable of submicron resolution. It has been found that the acetyl group of the 3‐oximino‐2‐butanone substituent is more effective than the related species containing t‐butyl, phenyl, or benzoyl groups in promoting polymer degradation. The copolymers have also been exposed to 20 kV electron beam radiation and have been found to be about as sensitive as PMMA false(5×10−5C/cm2false) .

Curing Systems Using Photolysis of Carbomoyloxyimino Groups and Themally Regenerated Isocyanate Groups.

“…[ 10,11 ] Some 0-acyl-a-oxooximes are also known, whose molar absorption coefficients are higher than D-acyloximes without a-oxo moiety. [ 12] In this communication, we report the photochemical and thermo chemical behavior of oligomers bearing COI groups with or without aoxo moieties. Two monomers; 2,3-butandione 0-methacryloyloxyethylcarbamoyloxime (BaMCO) and 2-butanone 0-methacryloyloxyethylcarbamoyloxime (BMCO), were oligomerized with methyl methacrylate (MMA).…”

“…After evaporation of dichloromethane, the residue was purified through a short column of silica gel with ethyl acetate to give 12 Oligomerization: DMF solution containing 50 wt% of monomers and 0.50 wt% of a, a'-azobisisobutylonitrile was placed in a tube fitted with an adaptor with stopcock. Nitrogen gas was bubbled, and the stopcock was sealed.…”

Photolysis of Polyamides Containing Thymine Photodimer Units in the Main Chain and Application to Deep-UV Positive Type Photoresists

“…22, No. 6,1990 ' " , , , pattern transferred to these polymers had lines and spaces of even 0.1 jIm. Lines of 0.3 jIm are clearly resolved in both of these polymers.…”

“…22, No. 6,1990 The ratios of the photodissociation cross section to the equilibrium conversion ((J d Xe) can be obtained by plotting of -In{(Ae-A)/ Ae} against the exposure dose.…”

“…However, it has low sensitivity, which has been improved by copolymerization of methyl methacrylate with more absorb ant UV sensitive components. 6 Recently, we reported the successful synthesis of a new type of chain scission positive type photoresist based on polyamide containmg thymine photodimer units in the main 468 chain, and its photochemical reaction. In the synthesis of this polymer, thymine photodimer derivative prepared by photochemical reaction of the monomeric compound was reacted with 1 ,3-diamino propane in a condensation polymerization.…”