WO2011086757A1 - 感光性レジスト下層膜形成組成物及びレジストパターンの形成方法 - Google Patents
感光性レジスト下層膜形成組成物及びレジストパターンの形成方法 Download PDFInfo
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- WO2011086757A1 WO2011086757A1 PCT/JP2010/070380 JP2010070380W WO2011086757A1 WO 2011086757 A1 WO2011086757 A1 WO 2011086757A1 JP 2010070380 W JP2010070380 W JP 2010070380W WO 2011086757 A1 WO2011086757 A1 WO 2011086757A1
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- underlayer film
- resist underlayer
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/095—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer
- G03F7/0955—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer one of the photosensitive systems comprising a non-macromolecular photopolymerisable compound having carbon-to-carbon double bonds, e.g. ethylenic compounds
Definitions
- the present invention relates to a photosensitive resist underlayer film forming composition and a resist pattern forming method using a resist underlayer film formed from the composition, and more specifically, patterning of a resist underlayer film following the resist pattern.
- the present invention relates to a composition capable of forming a possible resist underlayer film and a method of forming a resist pattern using the resist underlayer film formed from the composition.
- a photosensitive resin composition comprising a photoresist (Patent Document 1) containing a polymer having hydroxyphenyl (meth) acrylate or a derivative thereof, an alkali-soluble resin component (A), and a photosensitive agent (B)
- a photosensitive resin composition for an interlayer insulating film wherein the component (A) contains a resin component (A1) having hydroxyphenyl (meth) acrylate or a derivative thereof as a structural unit (a1)
- Product Patent Document 2
- at least part of the hydrogen atom of the phenolic hydroxyl group of hydroxyphenyl (meth) acrylate or its derivative (a1) as a structural unit is naphthoquinone-1,2-diazide-5- (and / or- 4-)
- Photosensitive comprising a resin component (A1) having a structural unit (a
- a photosensitive resin composition (Patent Document 4) and a photoresist composition comprising a photoactive component and a resin, wherein the resin is i) one or more phenolic groups spaced apart and ii )
- a photoresist composition containing at least one photoacid-labile group (Patent Document 5).
- hydroxyphenyl methacrylate and hydroxyphenyl acrylate are collectively referred to as hydroxyphenyl (meth) acrylate.
- the photosensitive resin composition described in Patent Document 3 is suitable for forming a pattern constituting a color filter
- the photosensitive resin composition described in Patent Document 4 is used for an interlayer insulating film of an electronic component. It is merely described as being suitable for use as a microlens for a solid-state imaging device. That is, these documents are not intended for application to a photosensitive resist underlayer film forming composition of a polymer having hydroxyphenyl (meth) acrylate or a derivative thereof as a structural unit.
- a photosensitive resist underlayer film forming composition comprising a polymer comprising hydroxyphenyl (meth) acrylate or a derivative thereof, a compound having at least two vinyl ether groups, a photoacid generator and a solvent, No specific means or effects are suggested.
- the present invention has been made based on the above circumstances, and the problem to be solved is a composition for forming a photosensitive resist underlayer film containing a polymer having hydroxyphenyl (meth) acrylate or a derivative thereof as a structural unit. And a method of forming a resist pattern using a resist underlayer film formed from the composition and the composition.
- a photosensitive resist underlayer film forming composition comprising a polymer having a structural unit represented by the following formula (1), a compound having at least two vinyl ether groups, a photoacid generator and a solvent.
- a step of applying the photosensitive resist underlayer film forming composition described in the first aspect onto a semiconductor substrate and baking to form a resist underlayer film, and forming a photoresist film on the resist underlayer film A method of forming a photoresist pattern used for manufacturing a semiconductor device, comprising: a step, a step of exposing a semiconductor substrate covered with the resist underlayer film and the photoresist layer, and a step of developing after the exposure.
- the composition for forming a photosensitive resist underlayer film of the present invention can form a resist underlayer film that can be patterned by following the resist pattern.
- the photosensitive resist underlayer film forming composition of this invention has the effect that the resist underlayer film formed from this composition does not raise
- the photosensitive resist underlayer film forming composition of the present invention can provide a resist underlayer film that is well developed with an alkaline developer and that can significantly reduce the generation of residues.
- the photosensitive resist underlayer film forming composition of this invention can provide the resist underlayer film which can improve shape control remarkably.
- the composition for forming a photosensitive resist underlayer film of the present invention can form a resist underlayer film having excellent solvent resistance.
- a highly accurate and favorable photoresist pattern can be formed by forming a resist underlayer film having the above-described effects and performance.
- FIG. 1 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Example 1 is used.
- FIG. 2 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Example 2 is used.
- FIG. 3 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Example 3 is used.
- FIG. 4 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Example 4 is used.
- FIG. 5 shows a cross-sectional view of a photoresist pattern when the composition for forming a photosensitive resist underlayer film of Example 5 is used.
- FIG. 5 shows a cross-sectional view of a photoresist pattern when the composition for forming a photosensitive resist underlayer film of Example 5 is used.
- FIG. 6 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 1 is used.
- FIG. 7 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 3 is used.
- FIG. 8 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 4 is used.
- FIG. 9 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 5 is used.
- FIG. 10 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 6 is used.
- FIG. 11 is a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 7 is used.
- FIG. 12 shows a cross-sectional view of a photoresist pattern when the photosensitive resist underlayer film forming composition of Comparative Example 8 is used.
- the photosensitive resist underlayer film forming composition of the present invention contains a polymer having a structural unit represented by the above formula (1), a compound having at least two vinyl ether groups, a photoacid generator and a solvent. Moreover, the photosensitive resist underlayer film forming composition of this invention can contain a basic compound, surfactant, etc. further.
- the ratio of the solid content in the photosensitive resist underlayer film forming composition is not particularly limited as long as each component is uniformly dissolved, but is, for example, 0.1 to 70% by mass, or 1 to 60% by mass.
- the solid content is obtained by removing the solvent from all components of the photosensitive resist underlayer film forming composition.
- the polymer used in the present invention is a polymer having a structural unit represented by the following formula (1). (Wherein R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group having 1 to 4 carbon atoms, and i represents an integer of 0 to 4)
- the polymer may have a structural unit represented by the following formula (2) as a structural unit other than the structural unit represented by the above formula (1).
- R 1 represents a hydrogen atom or a methyl group
- R 3 represents a substituent that can be deprotected by an acid.
- the substituent R 3 that can be deprotected by the acid is a hydrocarbon group in which the carbon atom bonded to the oxygen atom (bonded to the carbonyl group in the above formula (2)) is a tertiary carbon atom. is there.
- the substituent that can be deprotected by this acid is also referred to as a protecting group or an acid dissociable group.
- R 3 include an ethyladamantyl group, an ethylcyclohexyl group, an isopropyladamantyl group, and a tert-butyl group.
- Specific examples of the structural unit represented by the above formula (2) include structural units represented by the following formulas (3) to (9). The following formulas (3) to (9) 2) or more can be combined.
- R 1 represents a hydrogen atom or a methyl group
- R 4 represents an alkyl group having 1 to 4 carbon atoms. However, when a plurality of R 4 are present, they may be the same or different. .
- the compound represented by following formula (10), or the said compound and following formula It can be synthesized by adding a polymerization initiator to the compound represented by (11) and carrying out heat polymerization.
- R 1, R 2, and i are the same as those defined according to the equation (1).
- R 1 and R 3 have the same definitions as described in formula (2) above.
- polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (isobutyric acid) dimethyl, dimethyl
- examples include 2,2′-azobis (2-methylpropionate), benzoyl peroxide, lauroyl peroxide, and the like, and the polymerization is usually carried out by heating to 50 to 80 ° C. The reaction time is usually 2 to 100 hours, or 5 to 30 hours.
- a polymer having a structural unit represented by the above formula (1) and a structural unit represented by the above (2) that is, a copolymer, for example, 4-hydroxyphenyl methacrylate (hereinafter abbreviated as PQMA in this specification).
- EAMA Ethyl adamantyl methacrylate
- PQMA 4-hydroxyphenyl methacrylate
- ECMA ethyl cyclohexyl methacrylate
- IAM isopropyl adamantyl methacrylate
- PQMA 4-hydroxyphenyl methacrylate
- the polymer used in the present invention also has a structural unit represented by the above formula (2) in addition to the structural unit represented by the above formula (1), the above formula (1) and the above formula (2)
- the molar ratio is not particularly limited, but is 1: 1, for example.
- the polymer used in the present invention is represented by the structural unit represented by the above formula (1) and a structural unit different from the structural unit represented by the above formula (2) (for example, the following formula (12): May be included.
- ⁇ In Formula (12), R ⁇ 1 >, R ⁇ 2 > and i are synonymous with the definition as described in said Formula (1). ⁇
- the weight average molecular weight of the polymer is usually 1,000 to 200,000, or 3,000 to 30,000. If the weight average molecular weight of the polymer is less than 3,000, the solvent resistance may be insufficient. On the other hand, if the weight average molecular weight is too large, there may be a problem in resolution.
- the weight average molecular weight is a value obtained by using gel as a standard sample by gel permeation chromatography (GPC).
- the polymer content in the photosensitive resist underlayer film forming composition of the present invention is, for example, 0.5 to 95% by mass based on the solid content of the photosensitive resist underlayer film forming composition. 1.0 to 90% by mass. This is because when this ratio is too small or too large, solvent resistance may be difficult to obtain.
- the compound having at least two vinyl ether groups used in the present invention is a cross-linking agent and is a compound having 2 to 20, preferably 3 to 10, more preferably 3 to 6 vinyl ether groups.
- the compound having at least two vinyl ether groups is not particularly limited.
- the content of the compound having at least two vinyl ether groups in the photosensitive resist underlayer film forming composition of the present invention is, for example, from 0.1 to 0.1 based on the content in the solid content of the photosensitive resist underlayer film forming composition. 70% by mass and 1 to 60% by mass. This is because when this ratio is too small or too large, solvent resistance may be difficult to obtain.
- the photoacid generator used in the present invention is not particularly limited as long as it is a compound that generates an acid upon irradiation with light used for exposure.
- a diazomethane compound, an onium salt compound, a sulfonimide compound, a nitrobenzyl compound Benzoin tosylate compounds, halogen-containing triazine compounds, cyano group-containing oxime sulfonate compounds, and the like are preferred.
- the onium salt compound include diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoronormalbutanesulfonate, diphenyliodonium perfluoronormaloctanesulfonate, diphenyliodonium camphorsulfonate, bis (4-tert-butyl).
- Phenyl) iodonium camphorsulfonate iodonium salts such as bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, or triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoronormalbutanesulfonate, triphenylsulfonium camphorsulfonate, triphenyl Sulfonium salt compounds such as sulfonium perfluoro butyl sulfonate and triphenylsulfonium trifluoromethane sulfonate, and the like.
- iodonium salts such as bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, or triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoronormalbut
- sulfonimide compound examples include N- (trifluoromethanesulfonyloxy) succinimide, N- (nonafluoro-normalbutanesulfonyloxy) succinimide, N- (camphorsulfonyloxy) succinimide and N- (trifluoromethanesulfonyloxy) na
- examples include phthalimide.
- the content of the photoacid generator in the photosensitive resist underlayer film forming composition of the present invention is, for example, 0.01 to 10% by mass based on the content in the solid content of the photosensitive resist underlayer film forming composition.
- the content is 0.01 to 5% by mass. When this ratio exceeds 10% by mass, the storage stability of the resist underlayer film forming composition may be lowered, which may affect the pattern shape of the photoresist.
- the photosensitive resist underlayer film forming composition of the present invention may further contain a basic compound (quencher).
- a basic compound quencher
- By adding a basic compound it is possible to adjust the sensitivity during exposure of the resist underlayer film. Therefore, it is possible for the basic compound to react with the acid generated by the photoacid generator during exposure to reduce the sensitivity of the resist underlayer film. Moreover, the diffusion of the acid generated from the photoacid generator in the resist underlayer film in the exposed portion to the resist underlayer film in the unexposed portion can be suppressed.
- basic compounds include amines and ammonium hydroxides.
- the amines are not particularly limited.
- triethanolamine, tributanolamine, trimethylamine, triethylamine, trinormalpropylamine, triisopropylamine, trinormalbutylamine, tri-tert-butylamine, trinormaloctylamine there may be mentioned tertiary amines such as triisopropanolamine, phenyldiethanolamine, stearyldiethanolamine and diazabicyclooctane, and aromatic amines such as pyridine and 4-dimethylaminopyridine.
- primary amines such as benzylamine and normal butylamine
- secondary amines such as diethylamine and dinormal butylamine
- amines can be used alone or in combination of two or more.
- the content of the basic compound in the photosensitive resist underlayer film forming composition of the present invention is, for example, 0 to 5% by mass based on the content in the solid content of the photosensitive resist underlayer film forming composition, or 0 to 1% by mass. This is because if this ratio exceeds 1% by mass, the sensitivity may decrease.
- the photosensitive resist underlayer film forming composition of the present invention can contain a surfactant.
- the surfactant can further improve the applicability of the photosensitive resist underlayer film forming composition to the substrate.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene Polyoxyethylene alkyl allyl ethers such as ethylene nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan trioleate Sorbitan aliphatic acid esters such as stearate, polyoxyethylene sorbitan monolaurate, polyoxye Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as lensorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan
- EF303, EF352 Mitsubishi Materials Electronics Chemical Co., Ltd. (formerly Gemco Co., Ltd.)), Megafuck F171, F173, F176, F189, R189 (DIC Corporation (former Dainippon Ink and Chemicals) )), Florard FC430, FC431 (Sumitomo 3M), Asahi Guard AG710, Surflon S382, SC101, SC102, SC103, SC104, SC105, SC106 (Asahi Glass Co., Ltd.) ) Fluorine-based surfactants such as, but organosiloxane polymer KP-341 (manufactured by Shin-Etsu Chemical Co., Ltd.) and the like, but is not limited thereto. These surfactants can be used alone or in combination of two or more.
- the content of the surfactant in the photosensitive resist underlayer film forming composition of the present invention is usually 3% by mass or less based on the solid content of the photosensitive resist underlayer film forming composition, preferably It is 1 mass% or less, More preferably, it is 0.5 mass% or less.
- the photosensitive resist underlayer film forming composition of the present invention may contain a rheology adjuster, an adhesion aid, and the like as necessary.
- composition for forming a photosensitive resist underlayer film of the present invention can be prepared by dissolving each of the above components in an appropriate solvent, and can be obtained in a uniform solution state.
- solvents examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate.
- the photosensitive resist underlayer film forming composition (solution) thus prepared is preferably used after being filtered using a filter or the like having a pore size of usually about 0.2 ⁇ m or 0.1 ⁇ m.
- the composition for forming a photosensitive resist underlayer film thus prepared is excellent in long-term storage stability at room temperature.
- Substrate for example, a semiconductor substrate such as silicon coated with a silicon oxide film, a semiconductor substrate such as silicon coated with a silicon nitride film or a silicon oxynitride film, a silicon nitride substrate, a quartz substrate, a glass substrate (non-alkali glass, low (Including alkali glass, crystallized glass), glass substrate on which an ITO film is formed, etc.
- the photosensitive resist underlayer film forming composition of the present invention is applied by an appropriate application method such as a spinner or a coater
- a resist underlayer film is formed by baking using a heating means such as a hot plate.
- Baking conditions are appropriately selected from a baking temperature of 80 to 250 ° C. and a baking time of 0.3 to 60 minutes, preferably a baking temperature of 130 to 250 ° C. and a baking time of 0.5 to 5 minutes.
- the baking temperature is lower than the above range, the crosslinked structure in the resist underlayer film becomes insufficient, and the resist underlayer film may cause intermixing with the photoresist.
- the baking temperature is too high, the crosslinked structure in the resist underlayer film may be cut, and the resist underlayer film may intermix with the photoresist.
- the film thickness of the resist underlayer film formed from the photosensitive resist underlayer film forming composition of the present invention is usually 0.001 to 3.0 ⁇ m, preferably 0.01 to 1.0 ⁇ m, more preferably. Is 0.03 to 0.5 ⁇ m.
- the resist underlayer film formed from the photosensitive resist underlayer film forming composition of the present invention is a polymer having a structural unit represented by the above formula (1) or the above formula (1) and the above under baking conditions at the time of formation.
- a strong film having a crosslinked structure is obtained.
- the resist underlayer film is made of a commonly used organic solvent such as ethylene glycol monomethyl ether, ethylene cellosolve acetate, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl as a photoresist solution applied thereon.
- Ether propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, methyl ethyl ketone, cyclohexanone, ⁇ -butyrolactone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, methyl pyruvate,
- the solubility in ethyl lactate and butyl lactate is low.
- a photoresist layer is formed on the resist underlayer film.
- the formation of the photoresist layer can be performed by a general method, that is, by applying and baking a photoresist solution on the resist underlayer film.
- the photoresist formed on the resist underlayer film obtained from the photosensitive resist underlayer film forming composition of the present invention is not particularly limited as long as it is sensitive to exposure light and exhibits a positive behavior.
- the photoresist include a positive photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonate, a binder having a group that decomposes with an acid to increase the alkali dissolution rate, and a photoacid generator.
- Chemically amplified photoresist a chemically amplified photoresist consisting of a low molecular weight compound that decomposes with acid to increase the alkali dissolution rate of the photoresist, an alkali-soluble binder, and a photoacid generator, an alkali dissolution rate that decomposes with acid
- a chemically amplified photoresist composed of a low-molecular compound that decomposes with a binder having an acid-raising group and an acid to increase the alkali dissolution rate of the photoresist and a photoacid generator.
- APEX -X Rohm and Haas Electronic Material Inc. (formerly Shipley Company), Ltd.
- PAR710 manufactured by Sumitomo Chemical Co., Ltd.
- SEPR430 trade name: Shin-Etsu Chemical Co., Ltd.
- a method for forming a photoresist pattern used for manufacturing a semiconductor manufacturing apparatus exposure is performed through a predetermined mask.
- a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), or the like can be used.
- post-exposure bake is performed as necessary.
- the conditions for the post-exposure heating are appropriately selected from a heating temperature of 80 to 150 ° C. and a heating time of 0.3 to 60 minutes.
- the semiconductor substrate coated with the resist underlayer film and the photoresist layer is exposed using a photomask, and then a semiconductor device is manufactured by development.
- the resist underlayer film formed from the photosensitive resist underlayer film forming composition of the present invention is used for developing a photoresist by the action of an acid generated from a photoacid generator contained in the resist underlayer film during exposure. It becomes soluble in an alkaline developer. Therefore, when both the resist underlayer film and the photoresist layer are collectively developed with an alkaline developer after exposure, the exposed portions of the resist underlayer film and the photoresist layer are removed because they exhibit alkali solubility.
- alkali developer examples include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, aqueous solutions of quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, and ethanolamine.
- alkaline aqueous solution such as an aqueous amine solution such as propylamine or ethylenediamine can be used.
- a surfactant or the like can be added to these developers.
- the development conditions are appropriately selected from a development temperature of 5 to 50 ° C. and a development time of 10 to 300 seconds.
- the resist underlayer film formed from the composition for forming a photosensitive resist underlayer film of the present invention is easily developed at room temperature using a 2.38 mass% tetramethylammonium hydroxide aqueous solution that is widely used for developing photoresists. It can be performed.
- the resist underlayer film formed from the photosensitive resist underlayer film forming composition of the present invention is formed upon exposure to a layer for preventing interaction between the substrate and the photoresist, a material used for the photoresist, or the photoresist. Reduces the poisoning effect of photoresist due to the layer that has the function of preventing the adverse effect of the substance on the semiconductor substrate, the layer that has the function of preventing the diffusion of the substance generated from the semiconductor substrate upon heating into the upper layer photoresist, and the dielectric layer It can also be used as a barrier layer or the like.
- this reaction liquid mixture was put into hexane, and the polymer was precipitated. And this polymer was dried under reduced pressure to obtain 13.7 g of a polymer represented by the following formula (16).
- the weight average molecular weight by GPC was 16,900 in terms of polystyrene.
- this reaction liquid mixture was put into hexane, and the polymer was precipitated. And this polymer was dried under reduced pressure, thereby obtaining 12.4 g of a polymer represented by the following formula (17).
- 10 g of the polymer thus obtained and 3 g of triethylamine were dissolved in 3 g of water, 30 g of methanol and 30 g of tetrahydrofuran, heated under reflux for 14 hours, then returned to room temperature, and the solution was concentrated. Then, after redissolving in 30 g of acetone, 3 g of acetic acid was added. Next, after stirring at room temperature for 30 minutes, 9.9 g of a polymer represented by the following formula (18) was obtained by adding the solution to water.
- the weight average molecular weight by GPC was 5,900 in terms of polystyrene.
- the mixture was filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a photosensitive resist underlayer film forming composition (solution).
- Example 5 To 0.3 g of the polymer obtained in Synthesis Example 1, 0.12 g of 1,3,5-tris (4-vinyloxybutyl) trimellitate represented by the above formula (19) and triphenylsulfonium perfluorobutylsulfonate 0 0.005 g was mixed and dissolved in 20.8 g of propylene glycol monomethyl ether to obtain a solution. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition (solution).
- the mixture was filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a photosensitive resist underlayer film forming composition (solution).
- the mixture was filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition (solution).
- the photosensitive resist underlayer film forming composition (solution) prepared in Comparative Examples 2 and 8 was applied onto a semiconductor substrate (silicon wafer) by a spinner and then baked at 200 ° C. for 1 minute using a hot plate. Then, a resist underlayer film (film thickness 0.05 ⁇ m) was formed.
- the line width of the photoresist pattern and the width between the lines are set to 0.00.
- Exposure was performed through a mask set to 20 ⁇ m.
- post-exposure bake was performed using a hot plate at 110 ° C. for 60 seconds.
- development was performed using a 0.26N tetramethylammonium hydroxide aqueous solution as a developer.
- the line width of the photoresist pattern and the width between the lines are set to 0.00.
- Exposure was performed through a mask set to 20 ⁇ m.
- post-exposure heating was performed at 110 ° C. for 60 seconds using a hot plate.
- development was performed using a 0.26N tetramethylammonium hydroxide aqueous solution as a developer.
- Comparative Example 5 showed an undercut shape in which a portion of the resist underlayer film under the photoresist pattern was removed as a result of excessive development of the resist underlayer film (see FIG. 9).
- Comparative Example 4 and Comparative Example 6 in which the basic compound was added without adding the photoacid generator, the resist underlayer film was not resolved in both cases (see FIGS. 8 and 10).
- Example 1 to which a photoacid generator and a basic compound were added was compared with Comparative Example 1, Example 1 showed a good pattern shape with no residual resist underlayer film after development (see FIG. 1).
- poly (4-hydroxyphenyl methacrylate) is contained together with a photoacid generator as compared with the case where poly (4-vinylphenol) is used as the polymer contained in the photosensitive resist underlayer film forming composition.
- poly (4-vinylphenol) is used as the polymer contained in the photosensitive resist underlayer film forming composition.
- there was no residue of the resist underlayer film and it was found that the shape of the resist underlayer film can be easily controlled.
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Abstract
Description
したがって、従来より様々なリソグラフィー用レジスト下層膜形成組成物が報告されている。
本明細書では、ヒドロキシフェニルメタクリレート及びヒドロキシフェニルアクリレートを総称して、ヒドロキシフェニル(メタ)アクリレートという。
すなわち、第1観点として、下記式(1)で表される構造単位を有するポリマー、少なくとも2つのビニルエーテル基を有する化合物、光酸発生剤及び溶剤を含む感光性レジスト下層膜形成組成物。
第2観点として、第1観点に記載の感光性レジスト下層膜形成組成物を半導体基板上に塗布し、ベークしてレジスト下層膜を形成する工程、前記レジスト下層膜上にフォトレジスト膜を形成する工程、前記レジスト下層膜と前記フォトレジスト層で被覆された半導体基板を露光する工程、及び前記露光後に現像する工程、を含む半導体装置の製造に用いるフォトレジストパターンの形成方法。
また本発明の感光性レジスト下層膜形成組成物は、該組成物から形成されるレジスト下層膜がその上のフォトレジストとの間でインターミキシングを起こさないという効果が得られる。
さらに、本発明の感光性レジスト下層膜形成組成物は、アルカリ性現像液を用いた現像が良好であって、残渣の発生を著しく低減させることが可能であるレジスト下層膜を提供することができる。
また本発明の感光性レジスト下層膜形成組成物は、形状制御を著しく改善できるレジスト下層膜を提供することができる。
本発明の感光性レジスト下層膜形成組成物は、優れた溶剤耐性を有するレジスト下層膜を形成することができる。
さらに本発明のフォトレジストパターンの形成方法によれば、上述の効果・性能を有するレジスト下層膜の形成により、高精度の良好なフォトレジストパターンを形成することができる。
本発明に用いられるポリマーは、下記式(1)で表される構造単位を有するポリマーである。
前記R3としては、例えばエチルアダマンチル基、エチルシクロヘキシル基、イソプロピルアダマンチル基、tert-ブチル基等が挙げられる。また上記式(2)で表される構造単位としては、具体的には下記式(3)乃至式(9)で表される構造単位を挙げることができ、下記式(3)乃至式(9)から2種以上を組み合わせることもできる。
式(11)中、R1、R3は、上記式(2)に記載の定義と同義である。}
また、本発明に用いられるポリマーは、上記式(1)で表される構造単位と共に、上記式(2)で表される構造単位とは異なる構造単位(例えば、下記式(12)で表される)を有していてもよい。
塩基性化合物を添加することにより、レジスト下層膜の露光時の感度調整を行うことができる。したがって、塩基性化合物が、露光時に光酸発生剤により発生した酸と反応し、レジスト下層膜の感度を低下させることが可能である。また、露光部のレジスト下層膜中の光酸発生剤より生じた酸の未露光部のレジスト下層膜への拡散を抑えることができる。
塩基性化合物としては、例えば、アミン類、水酸化アンモニウム類等を挙げることができる。
レジスト下層膜とフォトレジスト層で被膜された半導体基板を、フォトマスクを用いて露光を行い、その後、現像により半導体装置を製造する。本発明の感光性レジスト下層膜形成組成物から形成されるレジスト下層膜は、露光時にレジスト下層膜に含まれている光酸発生剤から発生する酸の作用によって、フォトレジストの現像に使用されるアルカリ性現像液に可溶となる。そのため、露光後、アルカリ性現像液でレジスト下層膜とフォトレジスト層の両方を一括現像すると、そのレジスト下層膜及びフォトレジスト層の露光された部分はアルカリ溶解性を示すため、除去される。
[下記合成例で得られたポリマーの重量平均分子量の測定]
装置:TOSOH HLC-8220GPC system
カラム:Shodex〔登録商標〕KF-803L、KF-802及びKF-801
カラム温度:40℃
溶離液:テトラヒドロフラン
流量:1ml/分
検出器:RI
<合成例1>
4-ヒドロキシフェニルメタクリレート(昭和高分子(株))15.0g、及び2,2’-アゾビス(イソ酪酸)ジメチル(和光純薬工業(株))0.9gをテトラヒドロフラン37.1gに溶解させ、窒素雰囲気下、加熱還流させたテトラヒドロフラン26.5g中へ滴下した。滴下終了後、加熱還流を保ちながら、18時間反応させた。その後、この反応混合液をヘキサンに入れ、ポリマーを沈殿させた。そして、このポリマーを減圧下で乾燥することで、下記式(13)で表されるポリマー14.1gを得た。GPCによる重量平均分子量は、ポリスチレン換算で24,700であった。
4-ヒドロキシフェニルメタクリレート(昭和高分子(株))5.5g、エチルアダマンチルメタクリレート(大阪有機化学工業(株))7.7g、及び2,2’-アゾビス(イソ酪酸)ジメチル(和光純薬工業(株))0.79gをテトラヒドロフラン32.6gに溶解させ、窒素雰囲気下、70℃に加熱させたプロピレングリコールモノメチルエーテル23.3g中へ滴下した。滴下終了後、70℃に保ちながら、14時間反応させた。その後、この反応混合液をヘキサンに入れ、ポリマーを沈殿させた。そして、このポリマーを減圧下で乾燥することで、下記式(14)で表されるポリマー10.8gを得た。GPCによる重量平均分子量は、ポリスチレン換算で10,150であった。
4-ヒドロキシフェニルメタクリレート(昭和高分子(株))5.5g、エチルシクロヘキシルメタクリレート(ダイセル化学工業(株))6.0g、及び2,2’-アゾビス(イソ酪酸)ジメチル(和光純薬工業(株))0.79gをテトラヒドロフラン28.8gに溶解させ、窒素雰囲気下、加熱還流させたテトラヒドロフラン20.6g中へ6時間かけて滴下した。滴下終了後、加熱還流を保ちながら、16時間反応させた。その後、この反応混合液をヘキサンに入れ、ポリマーを沈殿させた。そして、このポリマーを減圧下で乾燥することで、下記式(15)で表されるポリマー9.5gを得た。GPCによる重量平均分子量は、ポリスチレン換算で14,600であった。
4-ヒドロキシフェニルメタクリレート(昭和高分子(株))5.5g、イソプロピルアダマンチルメタクリレート(ダイセル化学工業(株))8.1g、及び2,2’-アゾビス(イソ酪酸)ジメチル(和光純薬工業(株))0.79gをテトラヒドロフラン33.6gに溶解させ、窒素雰囲気下、加熱還流させたテトラヒドロフラン24.0g中へ7時間かけて滴下した。滴下終了後、加熱還流を保ちながら、14時間反応させた。その後、この反応混合液をヘキサンに入れ、ポリマーを沈殿させた。そして、このポリマーを減圧下で乾燥することで、下記式(16)で表されるポリマー13.7gを得た。GPCによる重量平均分子量は、ポリスチレン換算で16,900であった。
4-アセトキシスチレン(東ソー有機化学(株))5.5g、エチルアダマンチルメタクリレート(大阪有機化学工業(株))8.4g、及び2,2’-アゾビス(イソ酪酸)ジメチル(和光純薬工業(株))0.87gをテトラヒドロフラン34.6gに溶解させ、窒素雰囲気下、70℃に加熱させたプロピレングリコールモノメチルエーテル24.7g中へ滴下した。滴下終了後、70℃に保ちながら、14時間反応させた。その後、この反応混合液をヘキサンに入れ、ポリマーを沈殿させた。そして、このポリマーを減圧下で乾燥することで、下記式(17)で表されるポリマー12.4gを得た。
<実施例1>
合成例1で得られたポリマー0.3gに、下記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0002gを混合し、プロピレングリコールモノメチルエーテル20.82gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例2で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0008gを混合し、プロピレングリコールモノメチルエーテル20.85gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例3で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0008gを混合し、プロピレングリコールモノメチルエーテル20.85gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例4で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0002gを混合し、プロピレングリコールモノメチルエーテル20.82gに溶解させ溶液とした。その後、孔経0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例1で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、及びトリフェニルスルホニウムパーフルオロブチルスルホネート0.005gを混合し、プロピレングリコールモノメチルエーテル20.8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過してレジスト下層膜形成組成物(溶液)を調製した。
ポリ(4-ビニルフェノール)0.3g(重量平均分子量Mw=8,000)(日本曹達(株))に、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0001gを混合し、プロピレングリコールモノメチルエーテル21.93gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例5で得られたポリマー0.35gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.14g、トリフェニルスルホニウムパーフルオロブチルスルホネート0.005g、及びトリエタノールアミン0.0001gを混合し、プロピレングリコールモノメチルエーテル25.30gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例1で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12gを混合し、プロピレングリコールモノメチルエーテル20.58gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過してレジスト下層膜形成組成物(溶液)を調製した。
合成例1で得られたポリマー0.3gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、及びトリエタノールアミン0.0002gを混合し、プロピレングリコールモノメチルエーテル20.8gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過してレジスト下層膜形成組成物(溶液)を調製した。
ポリ(4-ビニルフェノール)0.3g(重量平均分子量Mw=8,000)(日本曹達(株))に、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、及びトリフェニルスルホニウムパーフルオロブチルスルホネート0.005gを混合し、プロピレングリコールモノメチルエーテル21.93gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過してレジスト下層膜形成組成物(溶液)を調製した。
ポリ(4-ビニルフェノール)0.3g(重量平均分子量Mw=8,000)(日本曹達(株))に、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12g、及びトリエタノールアミン0.0001gを混合し、プロピレングリコールモノメチルエーテル21.69gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過してレジスト下層膜形成組成物(溶液)を調製した。
ポリ(4-ビニルフェノール)0.3g(重量平均分子量Mw=8,000)(日本曹達(株))に、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.12gを混合し、プロピレングリコールモノメチルエーテル21.69gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
合成例5で得られたポリマー0.35gに、上記式(19)で表される1,3,5-トリス(4-ビニルオキシブチル)トリメリテート0.14gを混合し、プロピレングリコールモノメチルエーテル25.30gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して感光性レジスト下層膜形成組成物(溶液)を調製した。
実施例1~5、及び比較例1、3~7で調製された感光性レジスト下層膜形成組成物(溶液)をスピナーにより、半導体基板(シリコンウェハ)上に塗布した。その後、ホットプレートを用いて、190℃で1分間ベークし、レジスト下層膜(膜厚0.05μm)を形成した。この得られたレジスト下層膜をフォトレジストに使用する溶剤、例えばプロピレングリコールモノメチルエーテル/プロピレングリコールモノメチルエーテルアセテート=7/3に浸漬し、その溶剤に難溶であることを確認した。なお、実施例1~4の溶剤耐性の結果を表1に示す。
実施例1~5、比較例1、3~7で調製された感光性レジスト下層膜形成組成物(溶液)を、スピナーを用いて半導体基板(シリコンウェハ)上に塗布した後、ホットプレートを用いて、190℃で1分間ベークし、レジスト下層膜(膜厚0.05μm)を形成した。この得られたレジスト下層膜の上に、市販のフォトレジスト溶液(JSR(株)製、商品名:V146G)を、スピナーを用いて塗布し、ホットプレートを用いて、110℃で60秒間加熱してフォトレジスト膜(膜厚0.28μm)を形成した。その後、(株)ニコン製スキャナーS-205C(波長248nm、NA:0.73、σ:0.85(CONVENTIONAL))を用い、現像後にフォトレジストパターンのライン幅及びそのライン間の幅が0.20μmになるよう設定されたマスクを通して、露光を行った。次に、ホットプレートを用いて、110℃で60秒間、露光後加熱(Post Exposure Bake)を行なった。冷却後、現像液として0.26規定のテトラメチルアンモニウムヒドロキシド水溶液を用いて現像した。
その結果、実施例1~5で調製された感光性レジスト下層膜形成組成物(溶液)を用いた場合、得られたフォトレジストパターンの形状は、図1~図5に示すようにレジスト下層膜が良好に解像され、残渣は観察されなかった。一方、比較例1で調製された感光性レジスト下層膜形成組成物(溶液)を用いた場合、レジスト下層膜が現像されず、フォトレジストパターンのライン間にレジスト下層膜の残渣が残っていた(図6参照)。また比較例2で調製された感光性レジスト下層膜形成組成物(溶液)を用いた場合、レジスト下層膜が過剰に現像され、フォトレジストパターンが倒れた。
各実施例及び各比較例で使用したポリマー及び上記組成物(溶液)中に含まれる添加剤を表2に示す。
次に、光酸発生剤を加え、塩基性化合物を加えなかった実施例5及び比較例5の場合、実施例5ではレジスト下層膜の残渣がなく良好なパターン形状を示し(図5参照)、一方、比較例5ではレジスト下層膜が過剰に現像された結果、フォトレジストパターン下部のレジスト下層膜の一部が除去されたアンダーカット形状を示した(図9参照)。
一方、光酸発生剤は加えずに塩基性化合物を加えた比較例4及び比較例6では、両方ともレジスト下層膜が解像されなかった(図8及び図10参照)。
光酸発生剤及び塩基性化合物を加えた実施例1と比較例1を比較したところ、実施例1では現像後にレジスト下層膜の残渣がなく良好なパターン形状を示した(図1参照)。一方、比較例1ではレジスト下層膜が解像されていないことが分かった(図6参照)。
Claims (6)
- 前記酸により脱保護が可能な置換基R3は、酸素原子に結合する炭素原子が第3級炭素原子であるところの炭化水素基である請求項2に記載の感光性レジスト下層膜形成組成物。
- さらに塩基性化合物を含む請求項1乃至請求項4のいずれか一項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項5のいずれか一項に記載の感光性レジスト下層膜形成組成物を半導体基板上に塗布し、ベークしてレジスト下層膜を形成する工程、前記レジスト下層膜上にフォトレジスト膜を形成する工程、前記レジスト下層膜と前記フォトレジスト層で被覆された半導体基板を露光する工程、及び前記露光後に現像する工程、を含む半導体装置の製造に用いるフォトレジストパターンの形成方法。
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TWI477918B (zh) | 2015-03-21 |
TW201135369A (en) | 2011-10-16 |
JP5708938B2 (ja) | 2015-04-30 |
JPWO2011086757A1 (ja) | 2013-05-16 |
KR20120105545A (ko) | 2012-09-25 |
US20120288795A1 (en) | 2012-11-15 |
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