WO2014171326A1 - Composition for forming resist underlayer film - Google Patents
Composition for forming resist underlayer film Download PDFInfo
- Publication number
- WO2014171326A1 WO2014171326A1 PCT/JP2014/059633 JP2014059633W WO2014171326A1 WO 2014171326 A1 WO2014171326 A1 WO 2014171326A1 JP 2014059633 W JP2014059633 W JP 2014059633W WO 2014171326 A1 WO2014171326 A1 WO 2014171326A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- resist underlayer
- underlayer film
- film forming
- forming composition
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- 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
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1422—Side-chains containing oxygen containing OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
Definitions
- the present invention relates to a resist underlayer film forming composition for a lithography process.
- the present invention relates to a composition for forming a resist underlayer film that has high hardness and is less likely to cause wiggling of a resist pattern formed by a lithography process.
- fine processing is performed by a lithography process.
- the lithography process when the resist layer on the substrate is exposed with an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser, the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
- an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser
- the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
- a resist pattern having a shape is not formed.
- it is adopted to provide a resist underlayer film (antireflection film) between the substrate and the resist layer.
- a novolak resin as a composition for forming a resist underlayer film.
- Patent Document 1 and Patent Document 2 disclose a photoresist underlayer film forming material containing a resin having a repeating unit obtained by novolakizing a compound having a bisphenol group.
- Patent Document 3 discloses a spin-coatable antireflection film composition containing a polymer having an aromatic ring condensed in three or more in the main chain of the polymer.
- a lithography process is also known in which at least two resist underlayer films are formed and used as a mask material in order to reduce the thickness of the resist layer required in accordance with the miniaturization of the resist pattern.
- the material forming the at least two layers include organic resins (for example, acrylic resins and novolac resins), silicon resins (for example, organopolysiloxane), and inorganic silicon compounds (for example, SiON, SiO 2 ).
- organic resins for example, acrylic resins and novolac resins
- silicon resins for example, organopolysiloxane
- inorganic silicon compounds for example, SiON, SiO 2
- an etching gas for example, fluorocarbon
- Patent Document 4 discloses a composition containing a polymer containing a heterocyclic aromatic moiety.
- the present invention solves the above problems. That is, the present invention provides the following formula (1): (Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, and X 2 Represents an organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, or a methoxy group. It is a resist underlayer film forming composition containing the polymer which has a structural unit represented, and a solvent.
- Examples of the halogeno group described above and below will include a chloro group and a bromo group.
- Examples of the divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring described above and below will be, for example, a phenylene group, biphenylylene group, terphenylylene group, fluorenylene group, naphthylene group, anthrylene group, pyrenylene group (the following formula ( a-1) and a group represented by the following formula (a-2)), a carbazolylene group (a group represented by the following formula (b)) and a group represented by the following formula (c) (wherein n represents Represents 0 or 1.).
- Examples of the organic group having 6 to 20 carbon atoms having at least one aromatic ring include a phenyl group, biphenylyl group, terphenylyl group, fluorenyl group, naphthyl group, anthryl group, pyrenyl group, carbazolyl group, and the following formula (d-1 And a group represented by the following formula (d-2) (wherein n represents 0 or 1).
- the polymer is further represented by the following formula (2): (Wherein X 1 represents a C 6-20 divalent organic group having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group, or a hydroxy group, and R 3 represents A phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a thienyl group or a pyridyl group; R 4 represents a hydrogen atom, a phenyl group or a naphthyl group; and R 3 and R 4 each represent a phenyl group, R 3 and R 4 may form a fluorene ring together with the same carbon atom to which they are attached. You may have a structural unit represented by these.
- the resist underlayer film forming composition of the present invention may further contain at least one of a crosslinking agent, an acidic compound, a thermal acid generator and a surfactant as an optional component.
- the resist underlayer film formed by using the resist underlayer film forming composition of the present invention has high hardness, and by applying the resist underlayer film, the bending of the pattern formed in the lithography process is suppressed. can do.
- Examples of the structural unit of the polymer having the structural unit represented by the above formula (1) contained in the resist underlayer film forming composition of the present invention are represented by the following formulas (1-1) to (1-10). Structural units.
- examples of the structural unit represented by the above formula (2) include a structural unit represented by the following formula (2-1).
- the weight average molecular weight of the polymer contained in the resist underlayer film forming composition of the present invention is, for example, 2,000 to 10,000 in terms of standard polystyrene.
- the polymer polymerizes a biphenol compound having two hydroxyphenyl groups, an aromatic compound or a heterocyclic compound, and if necessary, an aromatic aldehyde or an aromatic ketone in the presence of an acid catalyst such as a sulfonic acid compound. It can be synthesized by reaction.
- the biphenol compound having two hydroxyphenyl groups used for the synthesis of the polymer include 3,3 ', 5,5'-tetramethoxymethyl-4,4'-dihydroxybiphenyl.
- the aromatic compound used for the synthesis of the polymer include benzene, naphthalene, anthracene, pyrene, fluorene, and m-terphenyl.
- heterocyclic compound used for the synthesis of the polymer examples include carbazole.
- aromatic aldehyde used for the synthesis of the polymer examples include furfural, pyridinecarboxaldehyde, benzaldehyde, naphthylaldehyde, anthrylaldehyde, phenanthrylaldehyde, salicylaldehyde, phenylacetaldehyde, 3-phenylpropionaldehyde, tolylaldehyde, ( N, N-dimethylamino) benzaldehyde, acetoxybenzaldehyde, 1-pyrenecarboxaldehyde, anisaldehyde.
- the aromatic ketone used in the synthesis of the polymer is a diaryl ketone, and examples thereof include diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
- the biphenol compound used for the synthesis of the polymer is not limited to one type of compound, and two or more types may be used, and aromatic compounds, heterocyclic compounds, aromatic aldehydes and aromatic ketones are also limited to one type of compound. Two or more of them may be used.
- the resist underlayer film forming composition of the present invention can further contain a crosslinking agent.
- a cross-linkable compound having at least two cross-linking substituents is preferably used.
- examples thereof include melamine compounds, substituted urea compounds and phenolic compounds having a crosslink forming substituent such as a methylol group or a methoxymethyl group.
- Specific examples include compounds such as methoxymethylated glycoluril and methoxymethylated melamine, and examples include tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril, and hexamethoxymethylmelamine.
- examples of the substituted urea compound include tetramethoxymethylurea and tetrabutoxymethylurea.
- examples of phenolic compounds include tetrahydroxymethyl biphenol, tetramethoxymethyl biphenol, and tetramethoxymethyl bisphenol.
- cross-linking agent a compound having at least two epoxy groups can also be used.
- Examples of such compounds include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol Diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 '-Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, Epolide [registered trademark] GT-401
- Examples of such an epoxy resin include YH-434 and YH-434L (manufactured by Nippon Kayaku Epoxy Manufacturing Co., Ltd.).
- As the crosslinking agent a compound having at least two blocked isocyanate groups can also be used. Examples of such compounds include Takenate (registered trademark) B-830 and B-870N manufactured by Mitsui Chemicals, Inc. and VESTANAT (registered trademark) B1358 / 100 manufactured by Evonik Degussa.
- As the cross-linking agent a compound having at least two vinyl ether groups can also be used.
- Examples of such compounds include bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, 1,2,4-tris (4-vinyl).
- One kind selected from these various crosslinking agents may be added, or two or more kinds may be added in combination.
- the content of the crosslinking agent is, for example, 2% by mass to 60% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
- the resist underlayer film forming composition of the present invention can further contain an acidic compound.
- the acidic compound serves as a catalyst for promoting the cross-linking reaction.
- p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid examples include 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, sulfonic acid compounds such as hydroxybenzoic acid, and carboxylic acid compounds, and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid.
- a thermal acid generator can be contained.
- the thermal acid generator also serves as a catalyst for promoting the crosslinking reaction, and examples thereof include quaternary ammonium salts of trifluoromethanesulfonic acid.
- One kind selected from these acidic compounds and thermal acid generators may be added, or two or more kinds may be added in combination.
- the content ratio of the acidic compound or thermal acid generator is, for example, 0.1% by mass to 20% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
- the resist underlayer film forming composition of the present invention can further contain a surfactant.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as rubitan monopalmitate, polyoxyethylene sorbitan monostea
- One kind selected from these surfactants may be added, or two or more kinds may be added in combination.
- the content rate of the said surfactant is 0.01 mass% thru
- the resist underlayer film forming composition of the present invention can be prepared by dissolving each of the above components in an appropriate solvent, and is used in a uniform solution state.
- solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether acetate, propylene glycol.
- the step of applying and baking the resist underlayer film forming composition of the present invention includes a base material (for example, a silicon wafer, which is a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a metal film such as aluminum or tungsten).
- the composition may be coated by a suitable coating method such as a spinner or a coater, and then baked using a heating means such as a hot plate. Baking conditions are appropriately selected from a baking temperature of 100 ° C. to 400 ° C. and a baking time of 0.3 minutes to 10 minutes.
- An organopolysiloxane film is formed as a second resist underlayer film on the first resist underlayer film formed by the above process, and a resist pattern is formed thereon.
- the second resist underlayer film may be a SiON film or a SiN film formed by a vapor deposition method such as CVD or PVD.
- an antireflection film (BARC) may be formed as a third resist underlayer film on the second resist underlayer film, and the third resist underlayer film is a resist shape correction film having no antireflection ability. May be.
- exposure is performed through a mask (reticle) for forming a predetermined pattern or by direct drawing.
- the exposure source for example, g-line, i-line, KrF excimer laser, ArF excimer laser, EUV, or electron beam can be used.
- post-exposure heating Post Exposure Bake
- development is performed with a developer (for example, an aqueous 2.38 mass% tetramethylammonium hydroxide solution), and further rinsed with a rinse solution or pure water to remove the used developer.
- the resist pattern is dried and post-baked in order to improve adhesion to the base.
- the etching process performed after forming the resist pattern is performed by dry etching.
- the etching gas used for dry etching include CHF 3 , CF 4 , and C 2 F 6 for the second resist underlayer film (organopolysiloxane film).
- the resist underlayer film forming composition of the present invention For the formed first resist underlayer film, for example, O 2 , N 2 O, NO 2 can be mentioned, and for the surface having a step or a concave portion and / or a convex portion, for example, CHF 3 , CF 4 , C 2 F 6 is mentioned. Further, argon, nitrogen or carbon dioxide can be mixed with these gases.
- TMOM-Py a target polymer having a structural unit represented by the following formula (3) (hereinafter referred to as TMOM-Py in this specification) (Abbreviated) 28.6 g was obtained.
- the weight average molecular weight of the obtained TMOM-Py measured in terms of polystyrene by GPC was 2600.
- TMOM target polymer having two structural units represented by the following formula (4)
- -Cz-PCA target polymer having two structural units represented by the following formula (4)
- the obtained TMOM-Cz-PCA had a weight average molecular weight of 8,900 measured by polystyrene conversion by GPC.
- TMOM-Na a target polymer having a structural unit represented by the following formula (5) (hereinafter referred to as TMOM-Na in this specification). (Abbreviated) 5.9 g was obtained.
- the obtained TMOM-Na had a weight average molecular weight of 5,000 as measured by GPC in terms of polystyrene.
- the mixture was allowed to cool to 60 ° C., diluted with chloroform (34 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated into methanol (168 g, manufactured by Kanto Chemical Co., Inc.).
- the obtained precipitate was filtered and dried in a vacuum dryer at 80 ° C. for 24 hours to obtain 9.37 g of a target polymer having a structural unit represented by the following formula (6).
- the weight average molecular weight of the obtained polymer measured by polystyrene conversion by GPC was 2,800.
- Example 1 To 20 g of the polymer obtained in Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is 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 used in a lithography process using a multilayer film. did.
- Megafac R-30 manufactured by DIC Corporation
- Example 2 To 20 g of the polymer obtained in Synthesis Example 2, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is 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 used in a lithography process using a multilayer film. did.
- Megafac R-30 manufactured by DIC Corporation
- Example 3 To 20 g of the polymer obtained in Synthesis Example 3, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is 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 used in a lithography process using a multilayer film. did.
- Megafac R-30 manufactured by DIC Corporation
- Comparative Example 1 To 20 g of the polymer obtained in Comparative Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is 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 used in a lithography process using a multilayer film. did.
- Megafac R-30 manufactured by DIC Corporation
- Comparative Example 2 To 20 g of the polymer obtained in Comparative Synthesis Example 1, 3.0 g of TMOM-BP (produced by Honshu Chemical Industry Co., Ltd.) as a crosslinking agent, 0.6 g of pyridinium paratoluenesulfonate as a catalyst, and Megafac R-30 (as a surfactant) DIC Co., Ltd.) (0.06 g) was mixed and dissolved in 80 g of cyclohexanone to obtain a solution.
- TMOM-BP produced by Honshu Chemical Industry Co., Ltd.
- Megafac R-30 as a surfactant
- the mixture is 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 used in a lithography process using a multilayer film. did.
- the resist underlayer films formed by baking at 400 ° C. for 2 minutes using the resist underlayer film forming compositions of Examples 1 to 3 according to the present invention are those of Comparative Example 1 and Comparative Example 2. It was found that the resist underlayer film was harder than the resist underlayer film formed by baking under the same conditions using the resist underlayer film forming composition.
- the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.05 ⁇ m). These resist underlayer films were measured for refractive index (n value) and optical absorption coefficient (also referred to as k value or attenuation coefficient) at a wavelength of 193 nm using a spectroscopic ellipsometer. The results are shown in Table 2.
- the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.2 ⁇ m). These resist underlayer films were scraped from the silicon wafer to obtain a powder. The thermogravimetric phenomenon at 400 ° C. of the obtained powder was measured with TG / DTA (TG-DTA2010SR manufactured by BRUKER). The results are shown in Table 3.
- the etcher and etching gas used for the measurement of the dry etching rate are as follows.
- the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.25 ⁇ m). Next, the dry etching rate of these resist underlayer films was measured using CF 4 gas as an etching gas.
- phenol novolac resin commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5
- the applied wafer was baked on a hot plate at 205 ° C. for 1 minute to form a phenol novolac resin film (film thickness: 0.25 ⁇ m).
- CF 4 gas was used as an etching gas, and the dry etching rate of the phenol novolac resin film was measured.
- the resist underlayer film forming compositions prepared in Examples 1 to 3 and Comparative Example 2 were each applied onto a silicon wafer with a silicon oxide film using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 200 nm).
- a known silicon hard mask forming composition containing polysiloxane was applied onto the resist underlayer film and baked at 240 ° C. for 1 minute to form a silicon hard mask layer (film thickness: 45 nm). Further, a resist solution (PAR855 S90 (manufactured by Sumitomo Chemical Co., Ltd.)) was applied thereon and baked at 100 ° C.
- the above-described pattern formation is performed using the resist underlayer film forming composition prepared in Examples 1 to 3.
- the process was performed, and the pattern width at which the resulting pattern began to wiggle was observed with an electron microscope. Since the processing of the substrate based on the faithful pattern becomes impossible due to the occurrence of pattern bending, it is necessary to process the substrate with the pattern width (limit pattern width) immediately before the occurrence of the pattern bending. The narrower the limit pattern width at which pattern bending starts to occur, the finer the substrate can be processed.
- a length measurement scanning electron microscope manufactured by Hitachi High-Technologies Corporation was used for resolution measurement. Table 5 shows the measurement results.
- the resist underlayer film forming composition used in the lithography process using the multilayer film of the present invention can provide a resist underlayer film that can also have an effect as an antireflection film. Moreover, it turned out that the resist underlayer film forming composition of this invention has the heat resistance which can form a hard mask in the upper layer by CVD method. Further, even when the pattern width is narrowed, a good pattern is obtained in which pattern bending is difficult to occur, and a good pattern with no bend is obtained at a pattern width of at least about 50 nm.
Abstract
Description
(式中、X1は、ハロゲノ基、ニトロ基、アミノ基又はヒドロキシ基で置換されていてもよい芳香環を少なくとも1つ有する炭素原子数6乃至20の二価の有機基を表し、X2は、ハロゲノ基、ニトロ基、アミノ基又はヒドロキシ基で置換されていてもよい芳香環を少なくとも1つ有する炭素原子数6乃至20の有機基、又はメトキシ基を表す。)
で表される構造単位を有するポリマー及び溶剤を含むレジスト下層膜形成組成物である。 The present invention solves the above problems. That is, the present invention provides the following formula (1):
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, and X 2 Represents an organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, or a methoxy group.
It is a resist underlayer film forming composition containing the polymer which has a structural unit represented, and a solvent.
(式中、X1はハロゲノ基、ニトロ基、アミノ基又はヒドロキシ基で置換されていてもよい芳香環を少なくとも1つ有する炭素原子数6乃至20の二価の有機基を表し、R3はフェニル基、ナフチル基、アントリル基、ピレニル基、チエニル基又はピリジル基を表し、R4は水素原子、フェニル基又はナフチル基を表し、R3及びR4がそれぞれフェニル基を表すときR3及びR4はそれらが結合する同一の炭素原子と一緒になってフルオレン環を形成してもよい。)
で表される構造単位を有してもよい。 The polymer is further represented by the following formula (2):
(Wherein X 1 represents a C 6-20 divalent organic group having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group, or a hydroxy group, and R 3 represents A phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a thienyl group or a pyridyl group; R 4 represents a hydrogen atom, a phenyl group or a naphthyl group; and R 3 and R 4 each represent a phenyl group, R 3 and R 4 may form a fluorene ring together with the same carbon atom to which they are attached.
You may have a structural unit represented by these.
前記架橋剤としては、また、少なくとも二つのエポキシ基を有する化合物を用いることもできる。このような化合物として、例えば、トリス(2,3-エポキシプロピル)イソシアヌレート、1,4-ブタンジオールジグリシジルエーテル、1,2-エポキシ-4-(エポキシエチル)シクロヘキサン、グリセロールトリグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、2,6-ジグリシジルフェニルグリシジルエーテル、1,1,3-トリス[p-(2,3-エポキシプロポキシ)フェニル]プロパン、1,2-シクロヘキサンジカルボン酸ジグリシジルエステル、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、トリメチロールエタントリグリシジルエーテル、ビスフェノール-A-ジグリシジルエーテル、(株)ダイセル製のエポリード〔登録商標〕GT-401、同GT-403、同GT-301、同GT-302、セロキサイド〔登録商標〕2021、同3000、三菱化学(株)製の1001、1002、1003、1004、1007、1009、1010、828、807、152、154、180S75、871、872、日本化薬(株)製のEPPN201、同202、EOCN-102、同103S、同104S、同1020、同1025、同1027、ナガセケムテックス(株)製のデナコール〔登録商標〕EX-252、同EX-611、同EX-612、同EX-614、同EX-622、同EX-411、同EX-512、同EX-522、同EX-421、同EX-313、同EX-314、同EX-321、BASFジャパン(株)製のCY175、CY177、CY179、CY182、CY184、CY192、DIC(株)製のエピクロン200、同400、同7015、同835LV、同850CRPを挙げることができる。前記少なくとも二つのエポキシ基を有する化合物としては、また、アミノ基を有するエポキシ樹脂を使用することもできる。このようなエポキシ樹脂として、例えば、YH-434、YH-434L(新日化エポキシ製造(株)製)が挙げられる。
前記架橋剤としては、また、少なくとも2つのブロックイソシアネート基を有する化合物を使用することもできる。このような化合物として、例えば、三井化学(株)製のタケネート〔登録商標〕B-830、同B-870N、エボニックデグサ社製のVESTANAT〔登録商標〕B1358/100が挙げられる。
前記架橋剤としては、また、少なくとも2つのビニルエーテル基を有する化合物を使用することもできる。このような化合物として、例えば、ビス(4-(ビニルオキシメチル)シクロヘキシルメチル)グルタレート、トリ(エチレングリコール)ジビニルエーテル、アジピン酸ジビニルエステル、ジエチレングリコールジビニルエーテル、1,2,4-トリス(4-ビニルオキシブチル)トリメリテート、1,3,5-トリス(4-ビニルオキシブチル)トリメリテート、ビス(4-(ビニルオキシ)ブチル)テレフタレート、ビス(4-(ビニルオキシ)ブチル)イソフタレート、エチレングリコールジビニルエーテル、1,4-ブタンジオールジビニルエーテル、テトラメチレングリコールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ネオペンチルグリコールジビニルエーテル、トリメチロールプロパントリビニルエーテル、トリメチロールエタントリビニルエーテル、ヘキサンジオールジビニルエーテル、1,4-シクロヘキサンジオールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ペンタエリスリトールジビニルエーテル、ペンタエリスリトールトリビニルエーテル及びシクロヘキサンジメタノールジビニルエーテルを挙げることができる。
これらの各種架橋剤から選択された1種類を添加してもよいし、2種以上を組合せて添加することもできる。前記架橋剤の含有割合は、本発明のレジスト下層膜形成組成物から後述する溶剤を除いた固形分に対して、例えば2質量%乃至60質量%である。 The resist underlayer film forming composition of the present invention can further contain a crosslinking agent. As the cross-linking agent, a cross-linkable compound having at least two cross-linking substituents is preferably used. Examples thereof include melamine compounds, substituted urea compounds and phenolic compounds having a crosslink forming substituent such as a methylol group or a methoxymethyl group. Specific examples include compounds such as methoxymethylated glycoluril and methoxymethylated melamine, and examples include tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril, and hexamethoxymethylmelamine. Furthermore, examples of the substituted urea compound include tetramethoxymethylurea and tetrabutoxymethylurea. Examples of phenolic compounds include tetrahydroxymethyl biphenol, tetramethoxymethyl biphenol, and tetramethoxymethyl bisphenol.
As the cross-linking agent, a compound having at least two epoxy groups can also be used. Examples of such compounds include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol Diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 '-Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, Epolide [registered trademark] GT-401, GT-403, GT-301, GT-302, Celoxide [registered trademark] 2021, 3000 manufactured by Daicel Corporation, 1001, 1002 manufactured by Mitsubishi Chemical Corporation 1003, 1004, 1007, 1009, 1010, 828, 807, 152, 154, 180S75, 871, 872, EPPN201, 202, EOCN-102, 103S, 104S, 1020 manufactured by Nippon Kayaku Co., Ltd. 1025, 1027, Denasel (registered trademark) EX-252, EX-611, EX-612, EX-614, EX-622, EX-611, EX-411, manufactured by Nagase ChemteX Corporation EX-512, EX-522, EX-421, EX-313, EX-314, EX-321, BAS Japan made of (stock) CY175, CY177, CY179, CY182, CY184, CY192, DIC (Ltd.) of Epichlone 200, the 400, the 7015, the 835LV, mention may be made of the same 850CRP. As the compound having at least two epoxy groups, an epoxy resin having an amino group can also be used. Examples of such an epoxy resin include YH-434 and YH-434L (manufactured by Nippon Kayaku Epoxy Manufacturing Co., Ltd.).
As the crosslinking agent, a compound having at least two blocked isocyanate groups can also be used. Examples of such compounds include Takenate (registered trademark) B-830 and B-870N manufactured by Mitsui Chemicals, Inc. and VESTANAT (registered trademark) B1358 / 100 manufactured by Evonik Degussa.
As the cross-linking agent, a compound having at least two vinyl ether groups can also be used. Examples of such compounds include bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, 1,2,4-tris (4-vinyl). Oxybutyl) trimellitate, 1,3,5-tris (4-vinyloxybutyl) trimellitate, bis (4- (vinyloxy) butyl) terephthalate, bis (4- (vinyloxy) butyl) isophthalate, ethylene glycol divinyl ether, 1 , 4-butanediol divinyl ether, tetramethylene glycol divinyl ether, tetraethylene glycol divinyl ether, neopentyl glycol divinyl ether, trimethylolpropane trivinyl ether Le, trimethylolethane trivinyl ether, hexanediol divinyl ether, 1,4-cyclohexanediol divinyl ether, tetraethylene glycol divinyl ether, pentaerythritol divinyl ether, and pentaerythritol trivinyl ether, and cyclohexanedimethanol divinyl ether.
One kind selected from these various crosslinking agents may be added, or two or more kinds may be added in combination. The content of the crosslinking agent is, for example, 2% by mass to 60% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
GPCカラム:TSKgel SuperMultipore〔登録商標〕Hz-N(東ソー(株))
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:0.35ml/分
標準試料:ポリスチレン(東ソー(株)) The weight average molecular weight and polydispersity shown in the following Synthesis Examples 1 to 3, Comparative Synthesis Example 1 and Comparative Synthesis Example 2 are measured by gel permeation chromatography (hereinafter abbreviated as GPC in this specification). based on. For the measurement, a GPC system manufactured by Tosoh Corporation is used, and the measurement conditions are as follows.
GPC column: TSKgel SuperMultipore [registered trademark] Hz-N (Tosoh Corporation)
Column temperature: 40 ° C
Solvent: tetrahydrofuran (THF)
Flow rate: 0.35 ml / min Standard sample: Polystyrene (Tosoh Corporation)
200mL四口フラスコに3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル(以下、本明細書ではTMOM-BPと略称する。)(23.83g、0.066mol、本州化学工業(株)製)、ピレン(27.00g、0.134mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.53g、0.003mol、東京化成工業(株)製)を加え、さらに1,4-ジオキサン(119.84g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。6時間後60℃まで放冷後、メタノール(1000g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、12時間乾燥させ、下記式(3)で表される構造単位を有する、目的とするポリマー(以下、本明細書ではTMOM-Pyと略称する。)28.6gを得た。得られたTMOM-Pyの、GPCによるポリスチレン換算で測定される重量平均分子量は2600であった。
In a 200 mL four-necked flask, 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl (hereinafter abbreviated as TMOM-BP) (23.83 g, 0.066 mol, Honshu Chemical Industry Co., Ltd.), pyrene (27.00 g, 0.134 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), p-toluenesulfonic acid monohydrate (0.53 g, 0.003 mol, Tokyo Chemical Industry Co., Ltd.) The product was further charged with 1,4-dioxane (119.84 g, manufactured by Kanto Chemical Co., Inc.), stirred, heated and dissolved until reflux was confirmed, and polymerization was started. Six hours later, the mixture was allowed to cool to 60 ° C. and then reprecipitated into methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered, dried in a vacuum dryer at 60 ° C. for 12 hours, and a target polymer having a structural unit represented by the following formula (3) (hereinafter referred to as TMOM-Py in this specification) (Abbreviated) 28.6 g was obtained. The weight average molecular weight of the obtained TMOM-Py measured in terms of polystyrene by GPC was 2600.
100mL四口フラスコにTMOM-BP(2.21g、0.006mol、本州化学工業(株)製)、カルバゾール(5.00g、0.030mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(5.76g、0.025mol、シグマアルドリッチ社製)、パラトルエンスルホン酸一水和物(0.89g、0.006mol、東京化成工業(株)製)を加え、さらに1,4-ジオキサン(25.75g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。7時間後60℃まで放冷後、メタノール(1000g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、12時間乾燥させ、下記式(4)で表される2種の構造単位を有する、目的とするポリマー(以下、本明細書ではTMOM-Cz-PCAと略称する。)6.3gを得た。得られたTMOM-Cz-PCAの、GPCによるポリスチレン換算で測定される重量平均分子量は8900であった。
In a 100 mL four-necked flask, TMOM-BP (2.21 g, 0.006 mol, manufactured by Honshu Chemical Industry Co., Ltd.), carbazole (5.00 g, 0.030 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 1-pyrenecarboxaldehyde (5.76 g, 0.025 mol, manufactured by Sigma-Aldrich), paratoluenesulfonic acid monohydrate (0.89 g, 0.006 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and 1,4-dioxane ( 25.75 g (manufactured by Kanto Chemical Co., Inc.) was charged, stirred, and heated to dissolve until reflux was confirmed, and polymerization was started. After 7 hours, the mixture was allowed to cool to 60 ° C. and then reprecipitated into methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered, dried in a vacuum dryer at 60 ° C. for 12 hours, and a target polymer having two structural units represented by the following formula (4) (hereinafter referred to as TMOM in the present specification). (Abbreviated as -Cz-PCA). The obtained TMOM-Cz-PCA had a weight average molecular weight of 8,900 measured by polystyrene conversion by GPC.
200mL四口フラスコにTMOM-BP(13.93g、0.038mol、本州化学工業(株)製)、ナフタレン(10.00g、0.078mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.31g、0.002mol、東京化成工業(株)製)を加え、さらに1,4-ジオキサン(56.56g、関東化学(株)製)を仕込み、撹拌し、リフラックスが確認されるまで昇温し溶解させ、重合を開始した。5時間後60℃まで放冷後、メタノール(1000g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、12時間乾燥させ、下記式(5)で表される構造単位を有する、目的とするポリマー(以下、本明細書ではTMOM-Naと略称する。)5.9gを得た。得られたTMOM-Naの、GPCによるポリスチレン換算で測定される重量平均分子量は5000であった。
In a 200 mL four-necked flask, TMOM-BP (13.93 g, 0.038 mol, manufactured by Honshu Chemical Industry Co., Ltd.), naphthalene (10.00 g, 0.078 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), p-toluenesulfonic acid Hydrate (0.31 g, 0.002 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and 1,4-dioxane (56.56 g, manufactured by Kanto Chemical Co., Inc.) was further added and stirred. The temperature was raised until dissolution was confirmed, and polymerization was started. After 5 hours, the mixture was allowed to cool to 60 ° C. and then reprecipitated into methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered, dried in a vacuum dryer at 60 ° C. for 12 hours, and a target polymer having a structural unit represented by the following formula (5) (hereinafter referred to as TMOM-Na in this specification). (Abbreviated) 5.9 g was obtained. The obtained TMOM-Na had a weight average molecular weight of 5,000 as measured by GPC in terms of polystyrene.
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9-フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、さらに1,4-ジオキサン(6.69g、関東化学(株)製)を仕込み、撹拌し、100℃まで昇温し溶解させ、重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥させ、下記式(6)で表される構造単位を有する、目的とするポリマー9.37gを得た。得られたポリマーの、GPCによるポリスチレン換算で測定される重量平均分子量は2800であった。
Carbazole (6.69 g, 0.040 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 9-fluorenone (7.28 g, 0.040 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), paratoluene in a 100 mL four-necked flask under nitrogen. Sulfonic acid monohydrate (0.76 g, 0.0040 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and 1,4-dioxane (6.69 g, manufactured by Kanto Chemical Co., Inc.) was further added and stirred. The temperature was raised to 100 ° C. to dissolve, and polymerization was started. After 24 hours, the mixture was allowed to cool to 60 ° C., diluted with chloroform (34 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated into methanol (168 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered and dried in a vacuum dryer at 80 ° C. for 24 hours to obtain 9.37 g of a target polymer having a structural unit represented by the following formula (6). The weight average molecular weight of the obtained polymer measured by polystyrene conversion by GPC was 2,800.
合成例1で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80g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、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。 (Example 1)
To 20 g of the polymer obtained in Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 μm, and further filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
合成例2で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80g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、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。 (Example 2)
To 20 g of the polymer obtained in Synthesis Example 2, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 μm, and further filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
合成例3で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80g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、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。 (Example 3)
To 20 g of the polymer obtained in Synthesis Example 3, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 μm, and further filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
比較合成例1で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80g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、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。 (Comparative Example 1)
To 20 g of the polymer obtained in Comparative Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 μm, and further filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
比較合成例1で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.6g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80g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、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。 (Comparative Example 2)
To 20 g of the polymer obtained in Comparative Synthesis Example 1, 3.0 g of TMOM-BP (produced by Honshu Chemical Industry Co., Ltd.) as a crosslinking agent, 0.6 g of pyridinium paratoluenesulfonate as a catalyst, and Megafac R-30 (as a surfactant) DIC Co., Ltd.) (0.06 g) was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 μm, and further filtered using a polyethylene microfilter having a pore size of 0.05 μm to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
実施例1乃至実施例3、比較例1及び比較例2で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で240℃1分間、または400℃2分間ベークし、レジスト下層膜(膜厚0.25μm)を形成した。これらのレジスト下層膜を、ナノインデンテーション装置G200(アジレント・テクノロジー社製)を用いて膜の硬度を測定した。その結果を表1に示す。 (Measurement of film hardness)
The resist underlayer film forming compositions prepared in Examples 1 to 3, Comparative Example 1 and Comparative Example 2 were each applied onto a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness: 0.25 μm). The hardness of the resist underlayer film was measured using a nanoindentation apparatus G200 (manufactured by Agilent Technologies). The results are shown in Table 1.
実施例1乃至実施例3及び比較例1で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で400℃2分間ベークし、レジスト下層膜(膜厚0.25μm)を形成した。このレジスト下層膜をレジストに使用する溶剤(乳酸エチル、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、シクロヘキサノン)に浸漬し、これらの溶剤に不溶であることを確認した。 (Elution test for photoresist solvent)
The resist underlayer film forming compositions prepared in Examples 1 to 3 and Comparative Example 1 were each applied onto a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness: 0.25 μm). This resist underlayer film was immersed in a solvent (ethyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone) used for the resist, and it was confirmed that the resist underlayer film was insoluble in these solvents.
実施例1乃至実施例3で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で240℃1分間または400℃2分間ベークし、レジスト下層膜(膜厚0.05μm)を形成した。これらのレジスト下層膜を、分光エリプソメーターを用いて波長193nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数ともいう)を測定した。その結果を表2に示す。
The resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.05 μm). These resist underlayer films were measured for refractive index (n value) and optical absorption coefficient (also referred to as k value or attenuation coefficient) at a wavelength of 193 nm using a spectroscopic ellipsometer. The results are shown in Table 2.
実施例1乃至実施例3で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で400℃2分間ベークし、レジスト下層膜(膜厚0.2μm)を形成した。これらのレジスト下層膜をシリコンウェハーから削り取り、粉末体を得た。得られた粉末体の400℃での熱重量現象をTG/DTA(BRUKER社製 TG-DTA2010SR)にて測定した。その結果を表3に示す。
The resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.2 μm). These resist underlayer films were scraped from the silicon wafer to obtain a powder. The thermogravimetric phenomenon at 400 ° C. of the obtained powder was measured with TG / DTA (TG-DTA2010SR manufactured by BRUKER). The results are shown in Table 3.
ドライエッチング速度の測定に用いたエッチャー及びエッチングガスは以下のものである。
エッチャー:RIE-10NR(サムコ(株)製)
エッチングガス:CF4
実施例1乃至実施例3で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で240℃1分間または400℃2分間ベークし、レジスト下層膜(膜厚0.25μm)を形成した。次にエッチングガスとしてCF4ガスを使用して、これらのレジスト下層膜のドライエッチング速度を測定した。また、フェノールノボラック樹脂(市販品、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.5)の溶液を、スピンコーターを用いてシリコンウェハー上に塗布し、塗布されたウェハーをホットプレート上で205℃1分間ベークしてフェノールノボラック樹脂膜(膜厚0.25μm)を形成した。次にエッチングガスとしてCF4ガスを使用して、そのフェノールノボラック樹脂膜のドライエッチング速度を測定した。このフェノールノボラック樹脂膜のドライエッチング速度を1.00とした時の、実施例1乃至実施例3で調製したレジスト下層膜形成組成物から形成したレジスト下層膜のドライエッチング速度を、ドライエッチング速度比として算出した結果を表4に示す。ドライエッチング速度が小さいほど、CF4ガスに対する耐エッチング性が高いことを示す。
ドライエッチング速度比=(レジスト下層膜のドライエッチング速度)/(フェノールノボラック樹脂膜のドライエッチング速度)
The etcher and etching gas used for the measurement of the dry etching rate are as follows.
Etcher: RIE-10NR (Samco Co., Ltd.)
Etching gas: CF 4
The resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.25 μm). Next, the dry etching rate of these resist underlayer films was measured using CF 4 gas as an etching gas. In addition, a solution of phenol novolac resin (commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5) is applied onto a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 205 ° C. for 1 minute to form a phenol novolac resin film (film thickness: 0.25 μm). Next, CF 4 gas was used as an etching gas, and the dry etching rate of the phenol novolac resin film was measured. When the dry etching rate of this phenol novolac resin film was set to 1.00, the dry etching rate of the resist underlayer film formed from the resist underlayer film forming composition prepared in Examples 1 to 3 was expressed as a dry etching rate ratio. The results calculated as are shown in Table 4. The smaller the dry etching rate, the higher the etching resistance against CF 4 gas.
Dry etching rate ratio = (Dry etching rate of resist underlayer film) / (Dry etching rate of phenol novolac resin film)
実施例1乃至実施例3及び比較例2で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてそれぞれ酸化ケイ素膜付きシリコンウェハー上に塗布した。塗布されたウェハーをホットプレート上で400℃2分間ベークし、レジスト下層膜(膜厚200nm)を形成した。そのレジスト下層膜上にポリシロキサンを含有する公知のシリコンハードマスク形成組成物を塗布し、それを240℃で1分間ベークし、シリコンハードマスク層(膜厚45nm)を形成した。さらにその上にレジスト溶液(PAR855 S90(住友化学(株)製))を塗布し、それを100℃で1分間ベークしレジスト層(膜厚120nm)を形成した。このレジスト層をマスクを用いて波長193nmで露光し、露光後加熱(PEB、105℃で1分間)を行った後、現像してレジストパターンを得た。その後、フッ素系ガス(成分はCF4)でドライエッチングを行い、レジストパターンをハードマスク層に転写した。次いで酸素系ガス(成分はO2)でドライエッチングを行い、レジストパターンを上記レジスト下層膜に転写した。その後、さらにフッ素系ガス(成分はC4F8)でドライエッチングを行い、シリコンウェハー上の酸化ケイ素膜の除去を行った。最終的に得られたそれぞれのパターン形状を電子顕微鏡で観察した。 (Check wiggling pattern width)
The resist underlayer film forming compositions prepared in Examples 1 to 3 and Comparative Example 2 were each applied onto a silicon wafer with a silicon oxide film using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 200 nm). A known silicon hard mask forming composition containing polysiloxane was applied onto the resist underlayer film and baked at 240 ° C. for 1 minute to form a silicon hard mask layer (film thickness: 45 nm). Further, a resist solution (PAR855 S90 (manufactured by Sumitomo Chemical Co., Ltd.)) was applied thereon and baked at 100 ° C. for 1 minute to form a resist layer (film thickness 120 nm). This resist layer was exposed using a mask at a wavelength of 193 nm, post-exposure heating (PEB, 105 ° C. for 1 minute), and then developed to obtain a resist pattern. Thereafter, dry etching was performed with a fluorine-based gas (component is CF 4 ), and the resist pattern was transferred to the hard mask layer. Next, dry etching was performed with an oxygen-based gas (component is O 2 ) to transfer the resist pattern to the resist underlayer film. Thereafter, dry etching was further performed with a fluorine-based gas (component is C 4 F 8 ) to remove the silicon oxide film on the silicon wafer. Each finally obtained pattern shape was observed with an electron microscope.
Claims (6)
- 下記式(1):
(式中、X1は、ハロゲノ基、ニトロ基、アミノ基又はヒドロキシ基で置換されていてもよい芳香環を少なくとも1つ有する炭素原子数6乃至20の二価の有機基を表し、X2は、ハロゲノ基、ニトロ基、アミノ基又はヒドロキシ基で置換されていてもよい芳香環を少なくとも1つ有する炭素原子数6乃至20の有機基、又はメトキシ基を表す。)
で表される構造単位を有するポリマー及び溶剤を含むレジスト下層膜形成組成物。 Following formula (1):
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, and X 2 Represents an organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, or a methoxy group.
A resist underlayer film forming composition comprising a polymer having a structural unit represented by formula (I) and a solvent. - 前記式(1)において、芳香環を少なくとも1つ有する炭素原子数6乃至20の二価の有機基はフェニレン基、ビフェニリレン基、ターフェニリレン基、フルオレニレン基、ナフチレン基、アントリレン基、ピレニレン基、カルバゾリレン基又は下記式(c)で表される基(式中、nは0又は1を表す。)であり、芳香環を少なくとも1つ有する炭素原子数6乃至20の有機基はフェニル基、ビフェニリル基、ターフェニリル基、フルオレニル基、ナフチル基、アントリル基、ピレニル基、カルバゾリル基、又は下記式(d-1)もしくは下記式(d-2)で表される基(式中、nは0又は1を表す。)である、請求項1に記載のレジスト下層膜形成組成物。
In the formula (1), the divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring is a phenylene group, a biphenylylene group, a terphenylylene group, a fluorenylene group, a naphthylene group, an anthrylene group, a pyrenylene group, a carbazolylene group. Or a group represented by the following formula (c) (wherein n represents 0 or 1), and the organic group having 6 to 20 carbon atoms having at least one aromatic ring is a phenyl group, a biphenylyl group, A terphenylyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a carbazolyl group, or a group represented by the following formula (d-1) or the following formula (d-2) (wherein n represents 0 or 1) The composition for forming a resist underlayer film according to claim 1, wherein
- 前記ポリマーは、更に下記式(2):
(式中、X1は請求項1に記載の定義と同義であり、R3はフェニル基、ナフチル基、アントリル基、ピレニル基、チエニル基又はピリジル基を表し、R4は水素原子、フェニル基又はナフチル基を表し、R3及びR4がそれぞれフェニル基を表すときR3及びR4はそれらが結合する同一の炭素原子と一緒になってフルオレン環を形成してもよい。)
で表される構造単位を有する請求項1又は請求項2に記載のレジスト下層膜形成組成物。 The polymer is further represented by the following formula (2):
Wherein X 1 is as defined in claim 1, R 3 represents a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a thienyl group or a pyridyl group, and R 4 represents a hydrogen atom or a phenyl group. Alternatively, it represents a naphthyl group, and when R 3 and R 4 each represent a phenyl group, R 3 and R 4 together with the same carbon atom to which they are bonded may form a fluorene ring.
The resist underlayer film forming composition of Claim 1 or Claim 2 which has a structural unit represented by these. - 更に界面活性剤を含む請求項1乃至請求項3のいずれか一項に記載のレジスト下層膜形成組成物。 The resist underlayer film forming composition according to any one of claims 1 to 3, further comprising a surfactant.
- 更に架橋剤を含む請求項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。 Furthermore, the resist underlayer film forming composition as described in any one of Claims 1 thru | or 4 containing a crosslinking agent.
- 更に酸性化合物及び/又は酸発生剤を含む請求項1乃至請求項5のいずれか一項に記載のレジスト下層膜形成組成物。 Furthermore, the resist underlayer film forming composition as described in any one of Claim 1 thru | or 5 containing an acidic compound and / or an acid generator.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015512438A JP6327481B2 (en) | 2013-04-17 | 2014-04-01 | Resist underlayer film forming composition |
CN201480021117.6A CN105143979B (en) | 2013-04-17 | 2014-04-01 | Composition is used in the formation of resist lower membrane |
KR1020157027401A KR102004697B1 (en) | 2013-04-17 | 2014-04-01 | Composition for forming resist underlayer film |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013-086861 | 2013-04-17 | ||
JP2013086861 | 2013-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014171326A1 true WO2014171326A1 (en) | 2014-10-23 |
Family
ID=51731278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2014/059633 WO2014171326A1 (en) | 2013-04-17 | 2014-04-01 | Composition for forming resist underlayer film |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP6327481B2 (en) |
KR (1) | KR102004697B1 (en) |
CN (1) | CN105143979B (en) |
TW (1) | TW201504766A (en) |
WO (1) | WO2014171326A1 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107531597A (en) * | 2015-03-06 | 2018-01-02 | 三菱瓦斯化学株式会社 | Compound, resin, lower layer film for lithography form material, lower layer film for lithography, pattern formation method and the purification process of compound or resin |
WO2018198960A1 (en) * | 2017-04-25 | 2018-11-01 | 日産化学株式会社 | Resist underlayer film formation composition in which fluorene compound is used |
US20190354018A1 (en) * | 2017-01-13 | 2019-11-21 | Nissan Chemical Corporation | Resist underlayer film-forming composition containing amide solvent |
WO2021112194A1 (en) * | 2019-12-04 | 2021-06-10 | 三菱瓦斯化学株式会社 | Composition for forming underlayer film for lithography, underlayer film for lithography, resist pattern forming method, circuit pattern forming method, oligomer, and purification method |
US20220089811A1 (en) * | 2019-01-11 | 2022-03-24 | Mitsubishi Gas Chemical Company, Inc. | Composition for film formation, resist composition, radiation-sensitive composition, method for producing amorphous film, resist pattern formation method, composition for underlayer film formation for lithography, method for producing underlayer film for lithography, and circuit pattern formation method |
WO2022107759A1 (en) * | 2020-11-19 | 2022-05-27 | 日産化学株式会社 | Resist underlayer film-forming composition |
KR20220149703A (en) | 2020-02-28 | 2022-11-08 | 닛산 가가쿠 가부시키가이샤 | Polymer manufacturing method |
KR20220149704A (en) | 2020-02-28 | 2022-11-08 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
KR20240009452A (en) | 2021-05-18 | 2024-01-22 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107340688B (en) * | 2016-04-29 | 2022-05-06 | 东友精细化工有限公司 | Composition for hard mask |
KR102349937B1 (en) * | 2017-03-27 | 2022-01-10 | 동우 화인켐 주식회사 | Composition for hard mask |
KR102383692B1 (en) * | 2017-06-30 | 2022-04-05 | 동우 화인켐 주식회사 | Composition for hard mask |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006259249A (en) * | 2005-03-17 | 2006-09-28 | Shin Etsu Chem Co Ltd | Material for forming lower layer film of photoresist and pattern forming method |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4570485B2 (en) * | 2005-03-04 | 2010-10-27 | 株式会社ニデック | Ophthalmic equipment |
JP4592463B2 (en) * | 2005-03-24 | 2010-12-01 | 三菱電線工業株式会社 | Electrical connector |
US7375172B2 (en) | 2005-07-06 | 2008-05-20 | International Business Machines Corporation | Underlayer compositions containing heterocyclic aromatic structures |
JP4662063B2 (en) | 2006-05-25 | 2011-03-30 | 信越化学工業株式会社 | Photoresist underlayer film forming material and pattern forming method |
US8017296B2 (en) | 2007-05-22 | 2011-09-13 | Az Electronic Materials Usa Corp. | Antireflective coating composition comprising fused aromatic rings |
CN101910949B (en) * | 2008-01-11 | 2013-07-24 | 日产化学工业株式会社 | Composition having urea group for forming silicon-containing resist underlying film |
US8722840B2 (en) * | 2010-11-17 | 2014-05-13 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition, and method for forming resist pattern using the same |
US8906592B2 (en) * | 2012-08-01 | 2014-12-09 | Az Electronic Materials (Luxembourg) S.A.R.L. | Antireflective coating composition and process thereof |
-
2014
- 2014-04-01 WO PCT/JP2014/059633 patent/WO2014171326A1/en active Application Filing
- 2014-04-01 KR KR1020157027401A patent/KR102004697B1/en active IP Right Grant
- 2014-04-01 JP JP2015512438A patent/JP6327481B2/en active Active
- 2014-04-01 CN CN201480021117.6A patent/CN105143979B/en active Active
- 2014-04-14 TW TW103113545A patent/TW201504766A/en unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006259249A (en) * | 2005-03-17 | 2006-09-28 | Shin Etsu Chem Co Ltd | Material for forming lower layer film of photoresist and pattern forming method |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3266759A4 (en) * | 2015-03-06 | 2018-10-17 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin |
CN107531597A (en) * | 2015-03-06 | 2018-01-02 | 三菱瓦斯化学株式会社 | Compound, resin, lower layer film for lithography form material, lower layer film for lithography, pattern formation method and the purification process of compound or resin |
US20190354018A1 (en) * | 2017-01-13 | 2019-11-21 | Nissan Chemical Corporation | Resist underlayer film-forming composition containing amide solvent |
US11798810B2 (en) * | 2017-01-13 | 2023-10-24 | Nissan Chemical Corporation | Resist underlayer film-forming composition containing amide solvent |
JP7056651B2 (en) | 2017-04-25 | 2022-04-19 | 日産化学株式会社 | Resist underlayer film forming composition using fluorene compound |
WO2018198960A1 (en) * | 2017-04-25 | 2018-11-01 | 日産化学株式会社 | Resist underlayer film formation composition in which fluorene compound is used |
JPWO2018198960A1 (en) * | 2017-04-25 | 2020-03-12 | 日産化学株式会社 | Resist underlayer film forming composition using fluorene compound |
US20220089811A1 (en) * | 2019-01-11 | 2022-03-24 | Mitsubishi Gas Chemical Company, Inc. | Composition for film formation, resist composition, radiation-sensitive composition, method for producing amorphous film, resist pattern formation method, composition for underlayer film formation for lithography, method for producing underlayer film for lithography, and circuit pattern formation method |
WO2021112194A1 (en) * | 2019-12-04 | 2021-06-10 | 三菱瓦斯化学株式会社 | Composition for forming underlayer film for lithography, underlayer film for lithography, resist pattern forming method, circuit pattern forming method, oligomer, and purification method |
KR20220149703A (en) | 2020-02-28 | 2022-11-08 | 닛산 가가쿠 가부시키가이샤 | Polymer manufacturing method |
KR20220149704A (en) | 2020-02-28 | 2022-11-08 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
WO2022107759A1 (en) * | 2020-11-19 | 2022-05-27 | 日産化学株式会社 | Resist underlayer film-forming composition |
KR20230108255A (en) | 2020-11-19 | 2023-07-18 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
KR20240009452A (en) | 2021-05-18 | 2024-01-22 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
Also Published As
Publication number | Publication date |
---|---|
JPWO2014171326A1 (en) | 2017-02-23 |
JP6327481B2 (en) | 2018-05-23 |
KR102004697B1 (en) | 2019-07-29 |
KR20160002741A (en) | 2016-01-08 |
CN105143979A (en) | 2015-12-09 |
CN105143979B (en) | 2019-07-05 |
TW201504766A (en) | 2015-02-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6191831B2 (en) | Resist underlayer film forming composition | |
JP6327481B2 (en) | Resist underlayer film forming composition | |
US8962234B2 (en) | Resist underlayer film forming composition and method for forming resist pattern using the same | |
CN107077071B (en) | Resist underlayer film forming composition containing polymer having arylene group | |
CN110546569B (en) | Composition for forming resist underlayer film | |
JP6471873B2 (en) | Resist underlayer film forming composition | |
US11542366B2 (en) | Composition for forming resist underlayer film and method for forming resist pattern using same | |
WO2018012253A1 (en) | Resist underlayer film forming composition containing compound having hydantoin ring | |
JP6901704B2 (en) | Resist underlayer film forming composition | |
JP2015145944A (en) | Composition for forming resist underlay film and method for forming resist pattern using the composition | |
WO2019039355A1 (en) | Composition for forming resist underlayer film |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201480021117.6 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14785384 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2015512438 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20157027401 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 14785384 Country of ref document: EP Kind code of ref document: A1 |