EP0588544A2
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EP
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Fine pattern forming material and pattern formation process
Assignee: Fujifilm Wako Pure Chemical Corp
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Filing: 1993-09-06
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Granted: —
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Expires: 2013-09-06
Abstract
Abstract A resist material comprising (a) a copolymer having as a functional group wherein R 2 and R 3 are, e.g. C 1-6 alkyl, and R 4 is, e.g. C 1-10 alkyl, (b) a compound which generates an acid when exposed to electron beams, and (c) a solvent, is suitable for forming a chemical-amplified positive-working fine pattern with high resolution and good shape.
Inventors
- 👤 Fumiyoshi C/O Tokyo Kenkyusho Urano
- 👤 Takaaki c/o Tokyo Kenkyusho Negishi
- 👤 Masayuki c/o Handotai Kenkyusenta Endo
- 👤 Kazuhiko c/o Handotai Kenkyusenta Hashimoto
- 👤 Akiko c/o Handotai Kenkyusenta Katsuyama
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 20:29
CPC Classifications
C; C08; C08F; C08F212/00; C08F212/02; C08F212/04; C08F212/14; C08F212/22; G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/039
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
291 words
A resist material comprising (a) a polymer represented by the formula: wherein R 1 is a hydrogen atom or a methyl group; R 2 and R 3 are independently a hydrogen atom or a straight, branched or cyclic alkyl group having 1 to 6 carbon atoms, provided that R 2 and R 3 cannot be hydrogen atoms at the same time; or R 2 and R 3 can form together a methylene linkage having 2 to 5 carbon atoms; R 4 is a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, a straight, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; R 5 is a hydrogen atom or a cyano group; R 6 is a hydrogen atom or a methyl group; R 7 is a hydrogen atom, a cyano group, -COOY in which Y is a straight, branched or cyclic alkyl group having 1 to 6 carbon atoms, or a group of the formula: in which Z is a hydrogen atom, a halogen atom, a straight or branched alkyl group having 1 to 10 carbon atoms, or a straight, branched or cyclic alkoxy group having 1 to 10 carbon atoms, or R 4 and R 5 can form together a group of the formula: -CO-O-CO-; k and t are independently an integer of 1 or more, provided that 0.1 -- k/(k+t) Z 0.9; and m is zero or an integer of 1 or more, provided that when m is an integer of 1 or more, 0.05≦ m/(k+t+m)≦ 0.50, (b) an acid generator which can generate an acid upon exposure to electron beams, and (c) a solvent capable of dissolving the components (a) and (b).
Claim 2
Dependent Claim
291 words
A resist material comprising (a) a polymer represented by the formula: wherein R 1 is a hydrogen atom or a methyl group; R 2 and R 3 are independently a hydrogen atom or a straight, branched or cyclic alkyl group having 1 to 6 carbon atoms, provided that R 2 and R 3 cannot be hydrogen atoms at the same time; or R 2 and R 3 can form together a methylene linkage having 2 to 5 carbon atoms; R 4 is a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, a straight, branched or cyclic haloalkyl group having 1 to 6 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; R 5 is a hydrogen atom or a cyano group; R 6 is a hydrogen atom or a methyl group; R 7 is a hydrogen atom, a cyano group, -COOY in which Y is a straight, branched or cyclic alkyl group having 1 to 6 carbon atoms, or a group of the formula: in which Z is a hydrogen atom, a halogen atom, a straight or branched alkyl group having 1 to 10 carbon atoms, or a straight, branched or cyclic alkoxy group having 1 to 10 carbon atoms, or R 4 and R 5 can form together a group of the formula: -CO-O-CO-; k and t are independently an integer of 1 or more, provided that 0.1 -- k/(k+t) Z 0.9; and m is zero or an integer of 1 or more, provided that when m is an integer of 1 or more, 0.05≦ m/(k+t+m)≦ 0.50, (b) an acid generator which can generate an acid upon exposure to electron beams, and (c) a solvent capable of dissolving the components (a) and (b).
Claim 3
Dependent Claim
92 words
A resist material according to Claim 1, wherein the acid generator (b) is a compound represented by the formula: wherein R 12 is a hydrogen atom, a halogen atom, a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms or a straight, branched or cyclic alkoxy group having 1 to 10 carbon atoms; and R 13 is a straight, branched or cyclic alkyl group having 1 to 8 carbon atoms, a phenyl group, an alkyl-substituted phenyl group, a halogen-substituted phenyl group, a benzyl group or an alkoxy-substituted phenyl group.
Claim 4
Dependent Claim
164 words
A resist material according to Claim 1, wherein the acid generator (b) is a compound represented by the formula: wherein R 22 , R 23 , R 24 and R 25 are independently a hydrogen atom, a halogen atom, a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group having 2 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a phenyl group, a substituted phenyl group, in which the substituent being one or more halogen atoms, straight, branched or cyclic alkyl groups having 1 to 10 carbon atoms, straight, branched or cyclic alkoxy groups having 1 to 10 carbon atoms, nitro groups or cyano groups, and R 22 together with R 23 , R 23 together with R 24 , adn R 24 together with R 25 , can independently form an alicyclic ring, a heteroalicyclic ring, an aromatic ring or a heteroaromatic ring.
Claim 5
Dependent Claim
152 words
A resist material according to Claim 1, wherein the acid generator (b) is a compound represented by the formula: wherein R 26 is a hydrogen atm, a halogen atom, a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, or a straight, branched or cyclic alkoxy group having 1 to 10 carbon atoms; R 27 is a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms; R 28 is an alkyl group having 1 to 3 carbon atoms; and R 29 is a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a phenyl group, a substituted phenyl group in which the substituent being one or more halogen atoms, straight, branched or cyclic alkyl groups having 1 to 10 carbon atoms or straight, branched or cyclic alkoxy groups having 1 to 10 carbon atoms.
Claim 6
Dependent Claim
75 words
A process for forming a fine pattern, which comprises (i) a step of coating the resist material of Claim 1 on a semiconductor substrate, followed by heat treatment for forming a resist film, (ii) a step of exposing the resist film to electron beams to image a pattern, followed by heat treatment depending on necessity, and (iii) a step of developing the resulting resist film with an alkaline aqueous solution to form a positive-working pattern.
Claim 7
Dependent Claim
137 words
A process for forming a fine pattern, which comprises (i) a step of coating an organic high polymer solution on a semiconductor substrate, followed by heat treatment to form an underlying film, (ii) a step of forming an inorganic intermediate film on the underlying film, (iii) coating the resist material of Claim 1 on the intermediate film, followed by heat treatment to form a resist film, (iv) a step of exposing the resist film to electron beams to image a pattern, followed by heat treatment depending on necessity, (v) a step of developing the resist film with an alkaline aqueous solution to form a positive-working pattern, (vi) a step of masking the resulting resist pattern, followed by etching of the intermediate film, and (vii) a step of masking the resulting pattern, followed by etching the underlying film.
Claim 8
Dependent Claim
23 words
A process according to Claim 6, wherein the organic high polymer solution is a solution containing a novolak resin as a major component.
Claim 9
Dependent Claim
20 words
A process according to Claim 6, wherein the inorganic intermediate film is a silicon oxide film or a spin- on-glass.
Claim 10
Dependent Claim
18 words
A resist material according to Claim 1, wherein m in the polymer of the formula [I] is zero.
Claim 11
Dependent Claim
72 words
A resist material according to Claim 1, wherein the monomer unit of the formula: in the polymer of the formula [I] is derived from at least one monomer selected from the group consisting p- and m-hydroxystyrene derivatives having a functional group of the formula: wherein R 2 , R 3 and R 4 are as defined in Claim 1, and p- and m-hydroxy-a-methylstyrene derivatives having a functional group of the formula [VI].
Claim 12
Dependent Claim
71 words
A resist material according to Claim 10, wherein the monomer is at least one member selected from the group consisting of p- and m-1-methoxy-1-methyl-ethoxystyrene, p- and m-1-benzyloxy-1-methylethox- ystyrene, p- and m-1-ethoxyethoxystyrene, p- and m-1-methoxyethoxystyrene, p- and m-1-n-butoxye- thoxystyrene, p- and m-1-isobutoxyethoxystyrene, p- and m-1-(1,1-dimethylethoxy)-1-methylethoxys- tyrene, p- and m-1-(1,1-dimethyiethoxy)ethoxystyrene, p- and m-1-(2-chloroethoxy)ethoxystyrene, p-and m-1-cyclohexyloxyethoxy-styrene, p- and m-1-(2-ethylhexyloxy)ethoxystyrene, p-and m-1-ethoxy-1-methylethoxystyrene, p- and m-1-n-propoxyethoxyethoxystyrene, p- and m-1-ethoxypropoxystyrene, p- and m-1-methoxybutoxystyrene, and p- and m-1-methoxycyclohexyloxystyrene.
References Cited (Backward Citations)
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