This invention provides, but is not limited to, novel oleanolic acid derivatives having the formula:

##STR00001##

wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.

This invention provides, but is not limited to, novel oleanolic acid derivatives having the formula:

##STR00001##

wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.

The invention provides a zwitterionic plastic crystal (ZIPC) compound in the form of a single molecule comprising: at least one positively charged functional group carrying at least one positive charge, and at least one negatively functional group carrying at least one negative charge, wherein the positively charged functional groups and the negatively charged functional groups are covalently tethered together in the molecule, and the net charge of the zwitterionic compound is zero, and wherein the compound exhibits evidence of molecular disorder in the solid state.

Disclosed are a salt represented by formula (I), an acid generator, and a resist composition comprising the same:

##STR00001##

wherein R.sup.1 and R.sup.2 each represent a hydroxy group, *—O—R.sup.10, *—O-L.sup.10-CO—O—R.sup.10; L.sup.10 represents an alkanediyl group; R.sup.10 represents an acid-labile group; R.sup.4, R.sup.5, R.sup.7 and R.sup.8 each represent a halogen atom, a haloalkyl group or a hydrocarbon group; A.sup.1 and A.sup.2 each represent a hydrocarbon group, the hydrocarbon group may have a substituent, and —CH.sub.2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO.sub.2—; m1 represents an integer of 1 to 5, m2 and m8 represent an integer of 0 to 5, m4, m5 and m7 represent an integer of 0 to 4, 1≤m1+m7≤5, 0≤m2+m8≤5; and AI.sup.− represents an organic anion.

A resist composition comprising a sulfonium salt of a carboxylic acid having a nitro-substituted benzene ring is provided. The carboxylic acid is free of iodine and bromine, and when the benzene ring is fluorinated, the number of fluorine atoms is up to 3. The resist composition offers a high sensitivity, reduced LWR and improved CDU independent of whether it is of positive or negative tone.

A resist composition comprising a sulfonium salt of a carboxylic acid having a nitro-substituted benzene ring is provided. The carboxylic acid is free of iodine and bromine, and when the benzene ring is fluorinated, the number of fluorine atoms is up to 3. The resist composition offers a high sensitivity, reduced LWR and improved CDU independent of whether it is of positive or negative tone.

A first object of the present invention is to provide an actinic ray-sensitive or radiation-sensitive resin composition with which a pattern having a good shape can be obtained. Furthermore, a second object of the present invention is to provide a resist film, a pattern forming method, and a method for manufacturing an electronic device, each relating to the actinic ray-sensitive or radiation-sensitive resin composition. In addition, a third object of the present invention is to provide a compound which can be suitably used in the actinic ray-sensitive or radiation-sensitive resin composition.

The actinic ray-sensitive or radiation-sensitive resin composition of an embodiment of the present invention includes a compound that generates an acid upon irradiation with actinic rays or radiation, an acid-decomposable resin having a weight-average molecular weight of 30,000 or less, and a solvent, and the compound that generates an acid upon irradiation with actinic rays or radiation includes a compound (I).

Processes for producing a N,N-dialkyl perfluoroalkyl-sulfonamide product of the formula R.sub.f—S(O).sub.2—NR.sub.aR.sub.b (I) in which R.sub.f represents fully or partially fluorinated alkyl groups with carbon 1 to 12 and R.sub.a and R.sub.b represents linear or branched or cyclic alkyl, alkene or alkyne groups with carbon 1 to 12, wherein R.sub.a=R.sub.b or R.sub.a≠R.sub.b. In some embodiments, a reaction proceeds by contacting a perfluoroalkylsulfonyl halide of the formula: X—S(O).sub.2—R.sub.f, (II), in which X represents F, Cl, Br or I, with dialkylamine of the formula HNR.sub.aR.sub.b, under conditions sufficient to produce the desired N,N-dialkyl perfluoroalkylsulfonamide product of Formula I. In some embodiments, the reaction is carried out using a solvent of Formula I.

Processes for producing a N,N-dialkyl perfluoroalkyl-sulfonamide product of the formula R.sub.f—S(O).sub.2—NR.sub.aR.sub.b (I) in which R.sub.f represents fully or partially fluorinated alkyl groups with carbon 1 to 12 and R.sub.a and R.sub.b represents linear or branched or cyclic alkyl, alkene or alkyne groups with carbon 1 to 12, wherein R.sub.a=R.sub.b or R.sub.a≠R.sub.b. In some embodiments, a reaction proceeds by contacting a perfluoroalkylsulfonyl halide of the formula: X—S(O).sub.2—R.sub.f, (II), in which X represents F, Cl, Br or I, with dialkylamine of the formula HNR.sub.aR.sub.b, under conditions sufficient to produce the desired N,N-dialkyl perfluoroalkylsulfonamide product of Formula I. In some embodiments, the reaction is carried out using a solvent of Formula I.

Processes for producing a N,N-dialkyl perfluoroalkyl-sulfonamide product of the formula R.sub.f—S(O).sub.2—NR.sub.aR.sub.b (I) in which R.sub.f represents fully or partially fluorinated alkyl groups with carbon 1 to 12 and R.sub.a and R.sub.b represents linear or branched or cyclic alkyl, alkene or alkyne groups with carbon 1 to 12, wherein R.sub.a=R.sub.b or R.sub.a≠R.sub.b. In some embodiments, a reaction proceeds by contacting a perfluoroalkylsulfonyl halide of the formula: X—S(O).sub.2—R.sub.f, (II), in which X represents F, Cl, Br or I, with dialkylamine of the formula HNR.sub.aR.sub.b, under conditions sufficient to produce the desired N,N-dialkyl perfluoroalkylsulfonamide product of Formula I. In some embodiments, the reaction is carried out using a solvent of Formula I.