KR102004697B1 - Composition for forming resist underlayer film - Google Patents
Composition for forming resist underlayer film Download PDFInfo
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- KR102004697B1 KR102004697B1 KR1020157027401A KR20157027401A KR102004697B1 KR 102004697 B1 KR102004697 B1 KR 102004697B1 KR 1020157027401 A KR1020157027401 A KR 1020157027401A KR 20157027401 A KR20157027401 A KR 20157027401A KR 102004697 B1 KR102004697 B1 KR 102004697B1
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- lower layer
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- KAWWJORWEBDXJN-UHFFFAOYSA-N C(C1)Cc2ccc3c4c2C1C=CC4=CCC3 Chemical compound C(C1)Cc2ccc3c4c2C1C=CC4=CCC3 KAWWJORWEBDXJN-UHFFFAOYSA-N 0.000 description 1
- MMXKBAXEKQEOPK-UHFFFAOYSA-N CCCC(C)(C)CC1=CC(c(cc2CC)cc(COC)c2O)=CC(CC)C1O Chemical compound CCCC(C)(C)CC1=CC(c(cc2CC)cc(COC)c2O)=CC(CC)C1O MMXKBAXEKQEOPK-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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
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- 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
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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
- G03F7/091—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
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- 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
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- 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
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- 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
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- 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
Abstract
[PROBLEMS] To provide a composition for forming a new resist lower layer film.
[MEANS FOR SOLVING PROBLEMS] The following formula (1)
[Chemical Formula 1]
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group, X 2 represents a halogen group, An organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a nitro group, an amino group or a hydroxy group, or a methoxy group.
And a solvent having a structural unit represented by the following formula (I).
Description
The present invention relates to a resist underlayer film forming composition for a lithographic process. In particular, the present invention relates to a composition for forming a resist underlayer film which is hard and hard to cause wiggling of a resist pattern formed by a lithography process.
In the manufacture of semiconductor devices, fine processing by a lithography process is performed. In the lithography process, when a resist layer on a substrate is exposed to an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser, a resist having a desired shape due to the influence of a standing wave generated due to reflection of the ultraviolet laser onto the substrate surface, A problem that a pattern is not formed is known. In order to solve the problem, it is employed that a resist underlayer film (antireflection film) is provided between a substrate and a resist layer. It is known that a novolak resin is used as a composition for forming a resist underlayer film. For example, Patent Document 1 and Patent Document 2 disclose a photoresist lower layer film-forming material containing a resin having a repeating unit in which a compound having a bisphenol group is novolak. Patent Document 3 discloses a spin coatable antireflection film composition comprising a polymer having an aromatic ring in which three or more of the polymer is condensed in the main chain.
Further, in order to make the required thickness of the resist layer thinner as the resist pattern is made finer, a lithography process is also known in which at least two lower resist layers are formed and the lower layer resist film is used as a mask material. (E.g., an acrylic resin, a novolac resin), a silicon resin (e.g., an organopolysiloxane), an inorganic silicon compound (e.g., SiON, SiO 2 ) . When dry etching is performed using a pattern formed from the organic resin layer as a mask, it is necessary that the pattern has an etching resistance to an etching gas (for example, fluorocarbon). As a composition for forming such an organic resin layer, for example, Patent Document 4 discloses a composition containing a polymer containing a heterocyclic aromatic moiety.
However, when the resist pattern is formed on the substrate to be processed through the lithography process and the etching process described above, irregular pattern bending tends to occur as the pattern width to be formed becomes narrow. Specifically, this means that a pattern formed from the organic resin layer, particularly in a resist underlayer film used as a mask material when etching a target substrate to be processed, is bent to the left and right.
The present invention solves the above problem. That is, the present invention relates to a compound represented by the following formula (1):
[Chemical Formula 1]
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group, X 2 represents a halogen group, An organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a nitro group, an amino group or a hydroxy group, or a methoxy group.
And a solvent having a structural unit represented by the following formula (1).
Examples of the halogen group described above and below include a chloro group and a bromo group. Examples of the divalent organic group having 6 to 20 carbon atoms and having at least one aromatic ring as described above and described later include a phenylene group, a biphenylene group, a terphenylene group, a fluorenylene group, a naphthylene group, (The group represented by the following formula (a-1) and the following formula (a-2)), the carbazolylene group (the group represented by the following formula (b) (Wherein n represents 0 or 1). Examples of the organic group having 6 to 20 carbon atoms and having at least one aromatic ring include a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a carbazolyl group, Include groups represented by formulas (d-1) and (d-2) (wherein n represents 0 or 1).
(2)
(2): < EMI ID =
(3)
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group, R 3 represents a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, represents a thienyl or pyridyl, R 4 represents a hydrogen atom, a phenyl or naphthyl, R 3, and when R 4 each represent a group R 3 and R 4 are the same carbon to which they are bonded And may be monovalent with the atoms to form a fluorene ring.)
May also be used.
The resist underlayer film forming composition of the present invention may further contain, as optional components, at least one of a crosslinking agent, an acidic compound, a thermal acid generator, and a surfactant.
The resist underlayer film formed using the resist underlayer film forming composition of the present invention has a high degree of hardness. Moreover, by applying this undercoat layer film, it is possible to suppress the wiggling of the pattern formed in the lithography process.
Examples of the structural unit of the polymer having the structural unit represented by the formula (1) contained in the resist lower layer film forming composition of the present invention include structural units represented by the following formulas (1-1) to (1-10) Structural units.
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
The structural unit represented by the formula (2) includes, for example, a structural unit represented by the following formula (2-1).
(7)
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 can be synthesized by polymerization reaction in the presence of 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. As the biphenol compound having two hydroxyphenyl groups used for the synthesis of the polymer, for example, 3,3 ', 5,5'-tetramethoxymethyl-4,4'-dihydroxybiphenyl . Examples of the aromatic compound used in the synthesis of the polymer include benzene, naphthalene, anthracene, pyrene, fluorene, and m-terphenyl. As the heterocyclic compound used for synthesis of the polymer, for example, carbazole can be cited. Examples of the aromatic aldehyde used in the synthesis of the polymer include furfural, pyridine carboxyaldehyde, benzaldehyde, naphthylaldehyde, anthrylaldehyde, phenanthrylaldehyde, salicylaldehyde, phenylacetaldehyde, Tolyl aldehyde, (N, N-dimethylamino) benzaldehyde, acetoxybenzaldehyde, 1-pyrrenecarboxyaldehyde and anisaldehyde. The aromatic ketone used for the synthesis of the polymer is a diaryl ketone, and examples thereof include diphenyl ketone, phenylnaphthyl ketone, dinaphthyl ketone, phenyltolyl ketone, ditolylketone, 9-fluorenone, . The biphenol compound used in the synthesis of the polymer is not limited to one kind of compound but may be used in two or more kinds. The aromatic compound, the heterocyclic compound, the aromatic aldehyde and the aromatic ketone are not limited to one kind of compound, It can also be used.
The resist underlayer film forming composition of the present invention may further contain a crosslinking agent. As the crosslinking agent, a crosslinking compound having at least two crosslinking forming substituents is preferably used. For example, a melamine compound, a substituted urea compound and a phenol compound having a crosslinking substituent group such as a methylol group or a methoxymethyl group can be given. Specific examples thereof include compounds such as methoxymethylated glycoluril and methoxymethylated melamine, and examples thereof include tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and hexamethoxymethylmelamine. Examples of the substituent-based compound include tetramethoxymethyl urea and tetrabutoxymethyl urea. As the phenolic compound, for example, tetrahydroxymethylbiphenol, tetramethoxymethylbiphenol and tetramethoxymethylbisphenol can be given.
As the crosslinking agent, a compound having at least two epoxy groups may 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 triglyceride Diethyleneglycol 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-epoxycyclohexanecarboxylic acid GT-401, GT-403, GT-301, GT-302, and the like manufactured by Daicel Chemical Industries, Ltd., CELLOXIDE 2021 and 3000 manufactured by Nippon Kayaku Co., Ltd., 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828, 807, 152, 154, 180S75, 871, 872, manufactured by Mitsubishi Chemical Corporation EPPNs 201, 202, EOCN-102, 103S, EX-612, EX-614, EX-622, EX-411, EX-512, EX-522, EX- CY175, CY177, CY179, CY182, CY184, CY192 manufactured by BASF Japan Ltd., EPICLON 200, 400, 7015, 835LV, 850CRP manufactured by DIC Corporation . As the compound having at least two epoxy groups, an epoxy resin having an amino group may also be used. Examples of such epoxy resins include YH-434 and YH-434L (manufactured by NSCC Epoxy Manufacturing Co., Ltd.).
As the crosslinking agent, a compound having at least two block isocyanate groups may also be used. Such compounds include, for example, TAKENATE 占 B-830, B-870N manufactured by Mitsui Chemicals, Inc., and VESTANAT 占 B1358 / 100 manufactured by Evonik Degussa.
As the crosslinking agent, a compound having at least two vinyl ether groups may also be used. As such a compound, for example, bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, Tris (4-vinyloxybutyl) trimellitate, 1,3,5-tris (4-vinyloxybutyl) trimellitate, bis (4- (vinyloxy) butyl) terephthalate, bis (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, trimethylol ethane trivinyl ether, hexanediol divinyl ether, 1,4-cyclohexanediol divinyl ether, tetraethylene glycol divinyl ether, pentaerythritol divinyl ether, pentaerythritol trivinyl ether and cyclohexanedimethanol And divinyl ether.
One kind selected from these various crosslinking agents may be added, or two or more kinds thereof 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 to be described later from the resist lower layer film forming composition of the present invention.
The resist underlayer film forming composition of the present invention may further contain an acidic compound. The acidic compound functions as a catalyst for accelerating the crosslinking reaction, and includes, for example, p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid , Sulfonic acid compounds such as 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid and hydroxybenzoic acid and carboxylic acid compounds such as hydrochloric acid, sulfuric acid, And the like. Instead of or in addition to the acidic compound, a thermal acid generator may be contained. The thermal acid generation system functions as a catalyst promoting the crosslinking reaction, and examples thereof include quaternary ammonium salts of trifluoromethanesulfonic acid. One kind selected from these acid compounds and thermal acid generators may be added, or two or more kinds thereof may be added in combination. The content of the acidic compound or thermal acid generator is, for example, from 0.1% by mass to 20% by mass with respect to the solid content excluding the solvent to be described later from the resist underlayer film forming composition of the present invention.
The resist underlayer film forming composition of the present invention may further contain a surfactant. Examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether and the like, polyoxyethylene octylphenyl Polyoxyethylene alkylaryl ethers such as ether, polyoxyethylene nonylphenyl ether and the like, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan Sorbitan fatty acid esters such as monooleate, sorbitan trioleate and sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monostearate, Polyoxyethylene sorbitan trioleate such as polyoxyethylene sorbitan trioleate and polyoxyethylene sorbitan tristearate, (Trade name) EF301, EF303, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), MEGAFAC [registered trademark] F171, F173, R-30, R- (Manufactured by DIC Corporation), FLUORAD FC430, FC431 (manufactured by Sumitomo 3M Ltd.), ASAHI GUARD [registered trademark] AG710, SURFLON [registered trademark] S-382, SC101, Fluorine surfactants such as SC102, SC103, SC104, SC105, and SC106 (manufactured by Asahi Glass Co., Ltd.), and organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.). One kind selected from these surfactants may be added, or two or more kinds thereof may be added in combination. The content of the surfactant is, for example, 0.01% by mass to 5% by mass with respect to the solid content excluding the solvent to be described later from the resist lower layer film forming composition of the present invention.
The resist lower layer film forming composition of the present invention can be prepared by dissolving each of the above components in a suitable solvent and is used in a uniform solution state. As such a solvent, for example, 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 Propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, 2- Methyl ethyl ketone, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 2-hydroxypropionate, ethyl 2-methylpropionate, ethyl ethoxyacetate, Ethyl, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate , Ethyl lactate, butyl lactate, N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone. These organic solvents may be used alone or in combination of two or more. The proportion of the solid content excluding the organic solvent from the above composition is, for example, 0.5% by mass to 30% by mass, preferably 0.8% by mass to 15% by mass.
The step of applying and baking the resist lower layer film forming composition of the present invention may be carried out by using a substrate (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, tungsten, By coating the composition on a substrate by a suitable coating method such as a spinner or a coater and then baking it using a heating means such as a hot plate. The baking conditions are appropriately selected from a baking temperature of 100 to 400 DEG C and a baking time of 0.3 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 CVD or PVD deposition method. An antireflection film (BARC) may be formed as the third resist underlayer film on the second resist underlayer film. Alternatively, the third undercoat film may be a resist-type correction film having no antireflective ability. In the step of forming the resist pattern, exposure is performed by passing through a mask (reticle) for forming a predetermined pattern or by direct drawing. As the exposure source, for example, g-line, i-line, KrF excimer laser, ArF excimer laser, EUV and electron beam can be used. After exposure, Post Exposure Bake is performed as necessary. Thereafter, development is carried out with a developer (for example, a 2.38 mass% aqueous solution of tetramethylammonium hydroxide), and the developer is washed with a rinse solution or pure water to remove the developer. Thereafter, post-baking is carried out in order to improve the drying property of the resist pattern and adhesion to the substrate.
The etching process performed after forming the resist pattern is performed by dry etching. As the etching gas used for dry etching, for example, CHF 3 , CF 4 and C 2 F 6 can be given as the second resist underlayer film (organopolysiloxane film), and as the resist underlayer film forming composition of the present invention The first resist underlayer film formed may be, for example, O 2 , N 2 O, or NO 2 , and may be CHF 3 , CF 4 , or C 2 for surfaces having stepped or concave portions and / F 6 . Further, these gases may be mixed with argon, nitrogen or carbon dioxide.
Hereinafter, the present invention will be described with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Examples.
Example
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 were measured by gel permeation chromatography (hereinafter abbreviated as GPC in this specification) . For the measurement, a GPC system manufactured by Tosoh Corporation was used, and the measurement conditions were as follows.
GPC column: TSKgel SuperMultipore TM Hz-N (Tosoh Corporation)
Column temperature: 40 ° C
Solvent: tetrahydrofuran (THF)
Flow rate: 0.35 ml / min
Standard samples: Polystyrene (Tosoh Corporation)
(Synthesis Example 1)
3,3 ', 5,5'-tetramethoxymethyl-4,4'-dihydroxybiphenyl (hereinafter abbreviated as TMOM-BP in the present specification) (23.83 g, 0.066 mol (27.00 g, 0.134 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), paratoluene sulfonic acid monohydrate (0.53 g, 0.003 mol, manufactured by Honshu Chemical Industry Co., Ltd.) (119.84 g, manufactured by Kanto Chemical Co., Inc.) was added thereto, stirred, heated to dissolve until the reflux was confirmed, and polymerization was initiated . After 6 hours, the mixture was cooled to 60 DEG C and then reprecipitated in methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered and dried in a vacuum dryer at 60 ° C for 12 hours to obtain 28.6 g of a target polymer having a structural unit represented by the following formula (3) (hereinafter abbreviated as TMOM-Py in this specification) ≪ / RTI > The weight average molecular weight of the obtained TMOM-Py measured by GPC in terms of polystyrene was 2,600.
(7)
(Synthesis Example 2)
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-pylene carboxy (0.25 g, 0.006 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added thereto, followed by the addition of 1,4-dioxane (25.75 g, 0.025 mol, manufactured by Sigma Aldrich) and paratoluene sulfonic acid hydrate Kanto Chemical Co., Inc.) was added thereto, stirred, heated to dissolve until the reflux was confirmed, and polymerization was initiated. After 7 hours, the mixture was cooled to 60 DEG C and then reprecipitated in methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The resulting precipitate was filtered and dried in a vacuum dryer at 60 ° C for 12 hours to obtain a target polymer having two kinds of structural units represented by the following formula (4) (hereinafter abbreviated as TMOM-Cz-PCA in this specification) ) Were obtained. The weight average molecular weight of the obtained TMOM-Cz-PCA measured by GPC conversion in terms of polystyrene was 8900.
[Chemical Formula 8]
(Synthesis Example 3)
(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.), paratoluene sulfonic acid monohydrate (0.31 g, 0.002 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added and then 1,4-dioxane (56.56 g, manufactured by Kanto Chemical Co., Inc.) Was heated to dissolve, and polymerization was initiated. After 5 hours, the mixture was cooled to 60 DEG C and then reprecipitated in methanol (1000 g, manufactured by Kanto Chemical Co., Inc.). The resulting precipitate was filtered and dried in a vacuum dryer at 60 ° C for 12 hours to obtain 5.9 g of a target polymer having a structural unit represented by the following formula (5) (hereinafter abbreviated as TMOM-Na in the present specification) ≪ / RTI > The weight average molecular weight of the obtained TMOM-Na measured by GPC conversion in terms of polystyrene was 5000.
[Chemical Formula 9]
(Comparative Synthesis Example 1)
Carbazole (6.69 g, 0.040 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) and 9-fluorenone (7.28 g, 0.040 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) (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.) Stirred, heated to 100 DEG C to dissolve, and polymerization started. After 24 hours, the mixture was cooled to 60 DEG C, diluted with chloroform (34 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated in methanol (168 g, manufactured by Kanto Chemical Co., Inc.). The resulting precipitate was filtered and dried in a reduced pressure dryer at 80 DEG C for 24 hours to obtain 9.37 g of a target polymer having the structural unit represented by the following formula (6). The polymer obtained had a weight average molecular weight of 2,800 as measured by GPC in terms of polystyrene.
[Chemical formula 10]
(Example 1)
20 g of the polymer obtained in Synthesis Example 1 was mixed with 0.06 g of MEGAFAC R-30 (manufactured by DIC Corporation) as a surfactant and dissolved in 80 g of cyclohexanone to prepare a solution. Thereafter, the mixture was filtered using a microfilter made of polyethylene having a pore diameter of 0.10 mu m, and then filtered using a microfilter made of polyethylene having a pore diameter of 0.05 mu m to prepare a resist lower layer film forming composition used in a lithography process using a multilayer film .
(Example 2)
20 g of the polymer obtained in Synthesis Example 2 was mixed with 0.06 g of MEGAFAC R-30 (manufactured by DIC Corporation) as a surfactant and dissolved in 80 g of cyclohexanone to prepare a solution. Thereafter, the mixture was filtered using a microfilter made of polyethylene having a pore diameter of 0.10 mu m, and then filtered using a microfilter made of polyethylene having a pore diameter of 0.05 mu m to prepare a resist lower layer film forming composition used in a lithography process using a multilayer film .
(Example 3)
20 g of the polymer obtained in Synthesis Example 3 was mixed with 0.06 g of MEGAFAC R-30 (manufactured by DIC Corporation) as a surfactant and dissolved in 80 g of cyclohexanone to prepare a solution. Thereafter, the mixture was filtered using a microfilter made of polyethylene having a pore diameter of 0.10 mu m, and then filtered using a microfilter made of polyethylene having a pore diameter of 0.05 mu m to prepare a resist lower layer film forming composition used in a lithography process using a multilayer film .
(Comparative Example 1)
20 g of the polymer obtained in Comparative Synthesis Example 1 was mixed with 0.06 g of MEGAFAC R-30 (manufactured by DIC Corporation) as a surfactant and dissolved in 80 g of cyclohexanone to prepare a solution. Thereafter, the mixture was filtered using a microfilter made of polyethylene having a pore diameter of 0.10 mu m, and then filtered using a microfilter made of polyethylene having a pore diameter of 0.05 mu m to prepare a resist lower layer film forming composition used in a lithography process using a multilayer film .
(Comparative Example 2)
3.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd.) as crosslinking agent, 0.6 g of pyridinium paratoluene sulfonate as a catalyst, and MEGAFAC R-30 (manufactured by DIC Corporation) as a surfactant were added to 20 g of the polymer obtained in Comparative Synthesis Example 1 0.06 g) were mixed and dissolved in 80 g of cyclohexanone to prepare a solution. Thereafter, the mixture was filtered using a microfilter made of polyethylene having a pore diameter of 0.10 mu m, and then filtered using a microfilter made of polyethylene having a pore diameter of 0.05 mu m to prepare a resist lower layer film forming composition used in a lithography process using a multilayer film .
(Measurement of film hardness)
The resist underlayer film forming compositions prepared in Examples 1 to 3 and Comparative Example 1 and Comparative Example 2 were respectively applied to a silicon wafer using a spin coater. The coated wafer was baked on a hot plate at 240 DEG C for 1 minute or 400 DEG C for 2 minutes to form a resist underlayer film (film thickness 0.25 mu m). The lower layer films of these resist films were measured for hardness by using a nanoindentation device G200 (manufactured by Agilent Technologies, Inc.). The results are shown in Table 1.
From the results shown in Table 1, the resist underlayer film formed by baking at 400 ° C for 2 minutes using the resist underlayer film forming composition of Examples 1 to 3 according to the present invention was found to have a resist underlayer film formation of Comparative Example 1 and Comparative Example 2 It can be seen that the composition has a higher hardness than the resist underlayer film formed by baking under the same conditions.
(Dissolution test for photoresist solvent)
The resist lower layer film forming compositions prepared in Examples 1 to 3 and Comparative Example 1 were applied to a silicon wafer using a spin coater. The coated wafer was baked on a hot plate at 400 DEG C for 2 minutes to form a resist lower layer film (film thickness 0.25 mu m). This lower resist film was immersed in a solvent (ethyl acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone) used for resists, and it was confirmed that these films were insoluble in these solvents.
(Measurement of optical parameters)
The resist lower layer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The coated wafer was baked on a hot plate at 240 DEG C for 1 minute or 400 DEG C for 2 minutes to form a resist lower layer film (film thickness: 0.05 mu m). The refractive index (n value) and the optical absorption coefficient (k value, damping coefficient) of these lower resist films were measured at a wavelength of 193 nm using a spectroscopic ellipsometer. The results are shown in Table 2.
(Measurement of heat resistance)
The resist lower layer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The coated wafer was baked on a hot plate at 400 DEG C for 2 minutes to form a resist lower layer film (film thickness 0.2 mu m). These lower resist film layers were cut out from a silicon wafer to obtain a powder. The thermogravimetric phenomenon of the obtained powder at 400 DEG C was measured by TG / DTA (TG-DTA2010SR manufactured by BRUKER). The results are shown in Table 3.
(Measurement of dry etching rate)
Etchers and etching gases used for the measurement of the dry etching rate are as follows.
Etcher: RIE-10NR (made by SAMCO Inc.)
Etching gas: CF 4
The resist lower layer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The coated wafer was baked on a hot plate at 240 DEG C for 1 minute or 400 DEG C for 2 minutes to form a resist lower layer film (film thickness 0.25 mu m). Next, the dry etching rate of these under-layer films was measured using CF 4 gas as the etching gas. Further, a solution of a 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 on a silicon wafer using a spin coater, The resulting wafer was baked on a hot plate at 205 DEG C for 1 minute to form a phenol novolak resin film (film thickness 0.25 mu m). Next, the dry etching rate of the phenol novolak resin film was measured using CF 4 gas as the etching gas. The dry etching rate of the resist lower layer film formed of the resist lower layer film forming composition prepared in Examples 1 to 3 when the dry etching rate of the phenol novolac resin film was 1.00 was calculated as the dry etching rate ratio Table 4 shows the results. The smaller the dry etching rate, the higher the etching resistance to CF 4 gas.
Dry etching rate ratio = (dry etching rate of resist lower layer film) / (dry etching rate of phenol novolak resin film)
(Confirmation of wiggling occurrence pattern width)
Each of the resist lower layer film forming compositions prepared in Examples 1 to 3 and Comparative Example 2 was applied to a silicon wafer having a silicon oxide film attached thereto using a spin coater, respectively. The coated wafer was baked on a hot plate at 400 DEG C for 2 minutes to form a resist lower layer film (film thickness: 200 nm). A known silicon hard mask forming composition containing polysiloxane was applied on the resist underlayer film and baked at 240 캜 for one minute to form a silicon hard mask layer (film thickness: 45 nm). Then, a resist solution (PAR855 S90, manufactured by Sumitomo Chemical Co., Ltd.) was coated thereon and baked at 100 DEG 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, followed by post exposure baking (PEB at 105 DEG C for 1 minute), and then developed to obtain a resist pattern. Thereafter, dry etching was performed with a fluorine-based gas (component: CF 4 ), and the resist pattern was transferred to the hard mask layer. Subsequently, dry etching was performed with an oxygen-based gas (O 2 component), and the resist pattern was transferred to the resist underlayer film. Thereafter, dry etching was performed again with a fluorine-based gas (component C 4 F 8 ) to remove the silicon oxide film on the silicon wafer. Each pattern shape finally obtained was observed with an electron microscope.
As the width of the pattern narrows, irregular patterns called wiggling tend to occur. Therefore, the above-described pattern forming process is performed using the resist lower layer film forming composition prepared in Examples 1 to 3, The pattern width at which wiggling of the obtained pattern starts to occur was observed with an electron microscope. As wiggling of the pattern occurs, it becomes impossible to process the substrate based on the faithful pattern. Therefore, it is necessary to perform the substrate processing by the pattern width (limit pattern width) just before the pattern wiggling occurs . The narrower the pattern width at which the wiggling of the pattern starts to become narrower, the finer the substrate can be processed. For measurement of the resolution, a scanning electron microscope (manufactured by Hitachi High-Technologies Corporation) was used. The measurement results are shown in Table 5.
The resist underlayer film forming composition used in the lithography process by the multilayer film of the present invention can provide a resist underlayer film which can also have an effect as an antireflection film. It is also understood that the resist underlayer film forming composition of the present invention has heat resistance capable of forming a hard mask on its upper layer by the CVD method. Even when the pattern width is narrowed, wiggling of the pattern hardly occurs and a good pattern can be obtained, and a good pattern without bending can be obtained at a pattern width of at least around 50 nm.
Claims (6)
(Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group, X 2 represents a halogen group, An organic group having 6 to 20 carbon atoms and at least one aromatic ring which may be substituted with a nitro group, an amino group or a hydroxy group, or a methoxy group.
And a solvent having a structural unit represented by the following formula (I).
In the above formula (1), the divalent organic group having 6 to 20 carbon atoms and having at least one aromatic ring may be a phenylene group, a biphenylene group, a terphenylene group, a fluorenylene group, a naphthylene 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 and at least one aromatic ring is preferably a phenyl group, (D-1) or a group represented by the following formula (d-2): wherein R 1 and R 2 are each independently a hydrogen atom, and n represents 0 or 1).
(2): < EMI ID =
(Wherein, X 1 is defined as agreed set forth in claim 1, R 3 is a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, represents a thienyl or pyridyl, R 4 is a hydrogen atom, a phenyl group or a naphthyl When R 3 and R 4 each represent a phenyl group, R 3 and R 4 may be taken together with the same carbon atom to which they are bonded to form a fluorene ring.)
And a structural unit represented by the following formula.
A composition for forming a resist lower layer film further comprising a surfactant.
A composition for forming a resist lower layer film, which further comprises a crosslinking agent.
A resist underlayer film forming composition further comprising an acidic compound and / or an acid generator.
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| JP2013086861 | 2013-04-17 | ||
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| PCT/JP2014/059633 WO2014171326A1 (en) | 2013-04-17 | 2014-04-01 | Composition for forming resist underlayer film |
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| KR102552910B1 (en) * | 2015-03-06 | 2023-07-10 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | Compound, resin, material for forming lower layer film for lithography, lower layer film for lithography, pattern formation method, and purification method of compound or resin |
| CN107340688B (en) * | 2016-04-29 | 2022-05-06 | 东友精细化工有限公司 | Composition for hard mask |
| KR102511277B1 (en) | 2017-01-13 | 2023-03-17 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition containing an amide solvent |
| KR102349937B1 (en) * | 2017-03-27 | 2022-01-10 | 동우 화인켐 주식회사 | Composition for hard mask |
| TWI748087B (en) * | 2017-04-25 | 2021-12-01 | 日商日產化學工業股份有限公司 | Resistor underlayer film forming composition using stilbene compound |
| KR102383692B1 (en) * | 2017-06-30 | 2022-04-05 | 동우 화인켐 주식회사 | Composition for hard mask |
| TW202039619A (en) * | 2019-01-11 | 2020-11-01 | 日商三菱瓦斯化學股份有限公司 | Composition for forming film, resist composition,radiation-sensitive composition, method forproducing amorphous film, method for formingresist pattern, composition for forming underlayerfilm for lithography, method for producing underlayer film for lithography, and method for forming circuit pattern |
| 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 |
| JPWO2021172296A1 (en) | 2020-02-28 | 2021-09-02 | ||
| WO2021172295A1 (en) | 2020-02-28 | 2021-09-02 | 日産化学株式会社 | Composition for forming resist underlayer film |
| 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 |
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| JP2006269249A (en) | 2005-03-24 | 2006-10-05 | Mitsubishi Cable Ind Ltd | Electric connector |
| US20140038109A1 (en) | 2012-08-01 | 2014-02-06 | Az Electronic Materials (Luxembourg) S.A.R.L. | Antireflective coating composition and process thereof |
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| JP4539845B2 (en) * | 2005-03-17 | 2010-09-08 | 信越化学工業株式会社 | Photoresist underlayer film forming material and pattern forming method |
| 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 |
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| JP2006269249A (en) | 2005-03-24 | 2006-10-05 | Mitsubishi Cable Ind Ltd | Electric connector |
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