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US 5,670,299 AGranted
Pattern formation process
AssigneeWako Pure Chemical Industries, Ltd.
InventorsFumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
Life of this patent
Estimating the term…
Abstract
A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
Claims18
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR20## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.5;
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of exposing the coating to light having a wavelength of 300 nm or less through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a developing solution after carrying out heat treatment if necessary.
12 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR22## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.5;
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of irradiating the coating with electron beams through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a development solution after carrying out heat treatment or without heat treatment.
12 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR24## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR25## wherein R.sup.8 are R.sup.9 independently a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a group represented by the formula:
- ##STR26## wherein R.sup.10 and R.sup.11 are independently a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms which may be either linear or branched;
- and n is zero or a natural number, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of exposing the coating to light having a wavelength of 300 nm or less through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a developing solution after carrying out heat treatment if necessary.
15 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR27## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.1 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- .sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR28## wherein R.sup.12 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group, a trifluoromethyl group, a phenyl group or a tolyl group;
- R.sup.13 and R.sup.14 are independently a hydrogen atom, or a linear or branched alkyl group having 1 to 5 carbon atoms;
- and R.sup.15 is a linear, 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, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of exposing the coating to light having a wavelength of 300 mm or less through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a developing solution after carrying out heat treatment if necessary.
15 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR29## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR30## wherein R.sup.16 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group, a trifluoromethyl group, a phenyl group or a tolyl group;
- and R.sup.17 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group or an alkoxy group, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of exposing the coating to light having a wavelength of 300 nm or less through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a developing solution after carrying out heat treatment if necessary.
14 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR31## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR32## wherein R.sup.18 is a trichloroacetyl group, a p-toluene-sulfonyl group, a p-trifluoromethylbenzenesulfonyl group, a methanesulfonyl group or a trifluoromethanesulfonyl group;
- and R.sup.19 and R.sup.20 are independently a hydrogen atom, a halogen atom or a nitro group, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of exposing the coating to light having a wavelength of 300 nm or less through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a developing solution after carrying out heat treatment if necessary.
14 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR33## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR34## wherein R.sup.8 and R.sup.9 are independently a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a group represented by the formula:
- ##STR35## wherein R.sup.10 and R.sup.11 are independently a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms which may be either linear or branched;
- and n is zero or a natural number, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of irradiating the coating with electron beams through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a development solution after carrying out heat treatment or without heat treatment.
15 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR36## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR37## wherein R.sup.12 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group, a trifluoromethyl group, a phenyl group or a tolyl group;
- R.sup.13 and R.sup.14 are independently a hydrogen atom, or a linear or branched alkyl group having 1 to 5 carbon atoms;
- and R.sup.15 is a linear, 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, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of irradiating the coating with electron beams through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a development solution after carrying out heat treatment or without heat treatment.
15 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR38## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR39## wherein R.sup.16 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group, a trifluoromethyl group, a phenyl group or a tolyl group;
- and R.sup.17 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group or an alkoxy group, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of irradiating the coating with electron beams through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a development solution after carrying out heat treatment or without heat treatment.
14 more elements
A process for forming a pattern which comprises
- (i) a step of coating a photoresist composition on a substrate, the photoresist composition comprising
- (a) a polymer having repeating units of the formula:
- ##STR40## wherein R.sup.1 is a hydrogen atom or a methyl group;
- R.sup.2 and R.sup.3 are independently a hydrogen atom, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms provided that R.sup.2 and R.sup.3 cannot be hydrogen atoms at the same time, and a combination of R.sup.2 and R.sup.3 being able to form a methylene chain having 2 to 5 carbon atoms;
- R.sup.4 is a linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, a linear, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group;
- R.sup.5 is a hydrogen atom or a cyano group;
- R.sup.7 is a hydrogen atom, a cyano group or--COOY;
- Y is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;
- R.sup.5 and R.sup.7 may bind to each other to form --CO--O--CO;
- k and l are independently a natural number (0.1.ltoreq.k/(k+l).ltoreq.0.9);
- and m is zero or a natural number (when m is a natural number, 0.05.ltoreq.m/(k+l+m).ltoreq.0.50),
- (b) a photosensitive compound which generates an acid upon exposure to light, the photosensitive compound being a compound represented by the formula:
- ##STR41## wherein R.sup.18 is a trichloroacetyl group, a p-toluene-sulfonyl group, a p-trifluoromethylbenzenesulfonyl group, a methanesulfonyl group or a trifluoromethanesulfonyl group;
- and R.sup.19 and R.sup.20 are independently a hydrogen atom, a halogen atom or a nitro group, and,
- (c) a solvent capable of dissolving the components (a) and (b);
- (ii) a step of irradiating the coating with electron beams through a mask after heat treatment, and
- (iii) a step of developing the coating by use of a development solution after carrying out heat treatment or without heat treatment.
14 more elements
Dependencies are inferred from the claim text.