Chemical amplified resist material containing photosensitive compound capable of generating an acid and specific polystyrene copolymer having functional groups that become alkali-soluble under an acid atmosphere

Claim 2

A resist material comprising: (a) a polymer represented by the formula: ##STR20## wherein R 1 is a methyl group, an isopropyl group, a tert-butyl group, a tetrahydropyranyl group, a trimethyl-silyl group or a tert-butoxycarbonyl group; R 2 is a hydrogen atom or a methyl group; and k and p are independently an integer of 1 or more provided that k/(k+p)=0.1 to 0.9, said repeating units (I) having a functional group which becomes alkali-soluble by chemical change during heating in the presence of an acid generated from a photosensitive compound when exposed to light; (b) a photosensitive compound capable of generating an acid, when exposure to light, in an amount of 1 to 20 parts by weight per 100 parts by weight of said polymer; and (c) a solvent for dissolving the components (a) and (b).

Claim 3

A resist material according to claim 1, wherein in the formula (I), R 1 is a tert-butyl group, a tetrahydropyranyl group or a trimethylsilyl group; and R 2 is a hydrogen atom.

Claim 4

A resist material according to claim 1, wherein in the formula (I), R 1 is a tert-butyl group; and R 2 is a hydrogen atom.

Claim 5

A resist material according to claim 1, wherein the polymer of the formula (I) is obtained by polymerizing a monomer of the formula: ##STR21## wherein R 1 and R 2 are as defined in claim 1, and eliminating R 1 at predetermined proportion using a suitable acid.

Claim 6

A resist material according to claim 1, wherein the polymer of the formula (I) is obtained by polymerizing p-tert-butoxystyrene and eliminating R 1 at predetermined proportion using a suitable acid.

Claim 7

A resist material according to claim 1, wherein the photosensitive compound (b) is a compound of the formula: ##STR22## wherein R 9 and R 10 are independently a straight-chain branched or cyclic alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms or a group of the formula: ##STR23## wherein R 11 and R 12 are independently a hydrogen atom, a lower alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms; n is zero or an integer of 1 or more; X is a carbonyl group, a carbonyloxy group or a sulfonyl group.

Claim 8

A resist material according to claim 1, wherein the photosensitive compound (b) is a compound of the formula: ##STR24## wherein R 13 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a trifluoromethyl group, or a group of the formula: ##STR25## wherein R 17 is a hydrogen atom or a methyl group; R 14 and R 15 are independently a hydrogen atom, or a lower alkyl group having 1 to 5 carbon atoms; and R 16 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a phenyl group, a halogen-substituted phenyl group, an alkyl-substituted phenyl group, an alkoxy-substituted phenyl group, or an alkylthio-substituted phenyl group.

Claim 9

A resist material according to claim 1, wherein the photosensitive compound (b) is a compound of the formula: ##STR26## wherein R 18 , R 19 , R 20 and R 21 are independently a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms; and Z - is a perchlorate ion, a p-toluenesulfonate ion or a trifluoromethanesulfonate ion.

Claim 10

A resist material according to claim 1, wherein the photosensitive compound (b) is a compound of the formula: ##STR27## wherein R 22 is a trichloroacetyl group, a p-toluenesulfonyl group, a p-trifluoromethylbenzenesulfonyl group, a methanesulfonyl group or a trifluoromethanesulfonyl group; and R 23 and R 24 are independently a hydrogen atom, a halogen atom, or a nitro group.

Claim 11

A resist material comprising: (a) a polymer represented by the formula: ##STR28## wherein R 1 is a methyl group, and isopropyl group, a tertbutyl group, a tetrahydropyranyl group, a trimethylsilyl group or a tert-butoxycarbonyl group; R 2 is a hydrogen atom or a methyl group; R 3 and R 5 are independently a hydrogen atom or a methyl group; R 4 is a hydrogen, carboxyl group, a cyano group, or a group of the formula: ##STR29## wherein R 7 is a hydrogen atom, a halogen atom or a lower alkyl group; R 6 is a hydrogen atom, a cyano group, or --COOR 8 , R 8 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms; k', p' and m are independently an integer of 1 or more, provided that 0.1≦k'/(k'+p')≦0.9 and 0.05≦m/(k'+p'+m)≦0.50 said repeating units (II) having a functional group which becomes alkali-soluble by chemical change during heating in the presence of an acid generated from a photosensitive compound when exposed to light; (b) a photosensitive compound capable of generating an acid, when exposed to light, in an amount of 1 to 20 parts by weight per 100 parts by weight of said polymer; (c) a solvent for dissolving the components (a) and (b).

Claim 12

A resist material comprising: (a) a polymer represented by the formula: ##STR28## wherein R 1 is a methyl group, and isopropyl group, a tertbutyl group, a tetrahydropyranyl group, a trimethylsilyl group or a tert-butoxycarbonyl group; R 2 is a hydrogen atom or a methyl group; R 3 and R 5 are independently a hydrogen atom or a methyl group; R 4 is a hydrogen, carboxyl group, a cyano group, or a group of the formula: ##STR29## wherein R 7 is a hydrogen atom, a halogen atom or a lower alkyl group; R 6 is a hydrogen atom, a cyano group, or --COOR 8 , R 8 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms; k', p' and m are independently an integer of 1 or more, provided that 0.1≦k'/(k'+p')≦0.9 and 0.05≦m/(k'+p'+m)≦0.50 said repeating units (II) having a functional group which becomes alkali-soluble by chemical change during heating in the presence of an acid generated from a photosensitive compound when exposed to light; (b) a photosensitive compound capable of generating an acid, when exposed to light, in an amount of 1 to 20 parts by weight per 100 parts by weight of said polymer; (c) a solvent for dissolving the components (a) and (b).

Claim 13

A resist material according to claim 10, wherein in the formula (II), R 1 is a tert-butyl group, a tetrahydropyranyl group, or a trimethylsilyl group; R 4 is a hydrogen atom or a cyano group; R 6 is a cyano group or a tert-butoxycarbonyl group; and R 2 , R 3 and R 5 are independently a hydrogen atom.

Claim 14

A resist material according to claim 10, wherein in the formula (II), R 1 is a tert-butyl group; R 4 is a hydrogen atom or a cyano group; R 6 is a cyano group; and R 2 , R 3 and R 5 are independently a hydrogen atom.

Claim 15

A resist material according to claim 10, wherein in the formula (II), R 1 is a tert-butyl group; R 6 is a tert-butoxycarbonyl group; and R 2 , R 3 , R 4 and R 5 are independently a hydrogen atom.

Claim 16

A resist material according to claim 10, wherein the polymer of the formula (II) is obtained by copolymerizing a monomer of the formula: ##STR30## wherein R 1 and R 2 are as defined in claim 4, with a monomer of the formula: ##STR31## wherein R 3 through R 6 are as defined in claim 4, and eliminating R 1 at predetermined proportion using a suitable acid.

Claim 17

A resist material according to claim 10, wherein the polymer of the formula (II) is obtained by copolymerizing p-tert-butoxystyrene and a monomer of the formula: ##STR32## wherein R 3 through R 6 are as defined in claim 4, and eliminating R 1 at predetermined proportion using a suitable acid.

Claim 18

A resist material according to claim 10, wherein the photosensitive compound (b) is a compound of the formula: ##STR33## wherein R 9 and R 10 are independently a straight-chain, branched, or cyclic alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms or a group of the formula: ##STR34## wherein R 11 and R 12 are independently a hydrogen atom, a lower alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms; n is zero or an integer of 1 or more; X is a carbonyl group, a carbonyloxy group or a sulfonyl group.

Claim 19

A resist material according to claim 10, wherein the photosensitive compound (b) is a compound of the formula: ##STR35## wherein R 13 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a trifluoromethyl group, or a group of the formula: ##STR36## wherein R 17 is a hydrogen atom or a methyl group; R 14 and R 15 are independently a hydrogen atom, or a lower alkyl group having 1 to 5 carbon atoms; and R 16 is a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a phenyl group, a halogen-substituted phenyl group, an alkyl-substituted phenyl group, an alkoxy-substituted phenyl group, or an alkylthio-substituted phenyl group.

Claim 20

A resist material according to claim 10, wherein the photosensitive compound (b) is a compound of the formula: ##STR37## wherein R 18 , R 19 , R 20 and R 21 are independently a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms; and Z - is a perchlorate ion, a p-toluenesulfonate ion or a trifluoromethanesulfonate ion.

Claim 21

A resist material according to claim 10, wherein the photosensitive compound (b) is a compound of the formula: ##STR38## wherein R 22 is a trichloroacetyl group, a p-toluenesulfonyl group, a p-trifluoromethylbenzenesulfonyl group, a methanesulfonyl group or a trifluoromethanesulfonyl group; and R 23 and R 24 are independently a hydrogen atom, a halogen atom, or a nitro group.