Polyfunctional compounds containing .alpha.-diazo-.beta.-keto ester units and sulfonate units are disclosed. The polyfunctional compounds have high sensitivity in the deep UV and high thermal stability. Processes for producing the compounds are disclosed. A preferred process first synthesizes .beta.-ketoester/sulfonate precursors and then uses diazo transfer to convert the precursors into the novel compounds. Radiation-sensitive mixtures containing the compounds are also disclosed.
Cyclic acetals or ketals are prepared by reacting a polyol with the appropriate aldehydes or ketones, with part of the aldehyde or ketone being distilled out during the reaction.
A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups, X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.4 --, --O--C(O)--NR.sup.3 --, ##STR3## or --O--C(O)--O--, or CH groups to be replaced by ##STR4## in which R.sup.3 and R.sup.4, independently of one another, are hydrogen or an unsubstituted or substituted aliphatic, carbocyclic or araliphatic radical, m is an integer from 3 to 8, n is an integer from 1 to 3, and m>n. The radiation-sensitive mixture is especially suitable for exposure to radiation having a wavelength of about 190 to 300 nm.
A positive working photoresist composition includes at least one thermally cross-linkable photoacid generator, a binder polymer, and a solvent in which the binder polymer and photoacid generator are dissolved. The photoacid generator is represented by the general formula (I): ##STR1## wherein X is methanesulfonate, trifluoromethanesulfonate, 4-toluenesulfonate, 10-camphorsulfonate, cyclohexane sulfamate, perfluoro-1-butanesulfonate, perfluorooctanesulfonate, F, Cl, Br, SbF.sub.6, BF.sub.4, PF.sub.4, or AsF.sub.6, R.sup.1 is hydrogen or methyl, and R.sup.2 is alkyl of C.sub.1-10 or vinyloxyethyl. The binder polymer represented by the general formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are different from each other and are selected from the group consisting of acid labile groups, hydrogen, methoxy, ethoxy, n-butoxy and t-butoxy, R.sup.3 is hydrogen or alkyl of C.sub.1-10, R.sup.4 is hydrogen or methyl, 0<o.ltoreq.1, 0.ltoreq.p.ltoreq.0.7, 0.ltoreq.q.ltoreq.0.7, and 0.ltoreq.r.ltoreq.0.3, wherein p, q and r are not 0 simultaneously.
