WO2021049472A1 - Composé, résine, composition, film de réserve, procédé de formation de motif, film de sous-couche et article optique - Google Patents

Composé, résine, composition, film de réserve, procédé de formation de motif, film de sous-couche et article optique Download PDF

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WO2021049472A1
WO2021049472A1 PCT/JP2020/033865 JP2020033865W WO2021049472A1 WO 2021049472 A1 WO2021049472 A1 WO 2021049472A1 JP 2020033865 W JP2020033865 W JP 2020033865W WO 2021049472 A1 WO2021049472 A1 WO 2021049472A1
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group
film
acid
composition
compound
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Japanese (ja)
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工藤　宏人
佐藤　隆
越後　雅敏
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学校法人 関西大学
三菱瓦斯化学株式会社
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Publication of WO2021049472A1 publication Critical patent/WO2021049472A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62—Three oxygen atoms, e.g. ascorbic acid
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • 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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes
    • 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
    • G03F7/022—Quinonediazides
    • 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
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34

Definitions

  • microfabrication is performed by lithography using photoresist materials, but in recent years, with the increasing integration and speed of LSIs (large-scale integrated circuits), further miniaturization by pattern rules has been performed. Is required.
  • Japanese Unexamined Patent Publication No. 53-59505 Japanese Unexamined Patent Publication No. 58-23616 JP-A-2009-501825 Japanese Patent No. 4832955
  • the present inventors have found that a compound or resin having a specific structure and a composition containing these can solve the above-mentioned problems, and have completed the present invention. That is, the present invention is as follows.
  • R 1 is independently a hydrogen atom, an alkyl group, a dissociative group or a cross-linking group, and at least one R 1 is an alkyl group, a dissociative group or a cross-linking group. is there.
  • composition according to [9] which further contains a solvent.
  • composition according to [9] or [10] which further contains an acid generator.
  • a composition for forming an underlayer film for lithography or forming an optical article which comprises ascorbic acid or a derivative thereof, or a resin containing a structural unit derived from ascorbic acid or a derivative thereof.
  • composition according to [16], wherein the ascorbic acid derivative is the compound according to any one of [1] to [3].
  • composition according to [23], wherein the silicon-containing compound is a hydrolyzable organosilane, a hydrolyzate thereof, or a hydrolyzed condensate thereof.
  • a method for purifying the compound or resin can be provided.
  • a composition for forming an underlayer film for lithography having high flatness of the obtained underlayer film, a composition for forming an optical article having high transparency of the obtained optical article, and a composition for forming an underlayer film for lithography It is possible to provide an underlayer film for lithography obtained by using an object, a pattern forming method using the underlayer film forming composition for lithography, and an optical article obtained by using the composition for forming an optical article.
  • an acid dissociable group having a property of dissociating with an acid is preferable from the viewpoint of easy availability and reactivity, and a substituted methyl group or a 1-substituted ethyl group having a property of dissociating with an acid, More preferably, a 1-substituted-n-propyl group, a 1-branched alkyl group, a silyl group, an acyl group, a 1-substituted alkoxymethyl group, a cyclic ether group, an alkoxycarbonyl group, or an alkoxycarbonylalkyl group.
  • the dissociative group preferably does not have a crosslinkable group.
  • the substituted methyl group is not particularly limited, but can usually be a substituted methyl group having 2 to 20 carbon atoms, preferably a substituted methyl group having 4 to 18 carbon atoms, and a substituted methyl group having 6 to 16 carbon atoms. More preferred. Specific examples of the substituted methyl group include, but are not limited to, a methoxymethyl group, a methylthiomethyl group, an ethoxymethyl group, an n-propoxymethyl group, an isopropoxymethyl group, an n-butoxymethyl group, a t-butoxymethyl group, and the like.
  • R 10 in the following formula (1-1) include, but are not limited to, methyl group, ethyl group, isopropyl group, n-propyl group, t-butyl group, n-butyl group and the like. Can be mentioned.
  • R 10 is an alkyl group having 1 to 4 carbon atoms.
  • the 1-substituted ethyl group is not particularly limited, but usually, it can be a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted ethyl group having 5 to 18 carbon atoms is preferable, and a 1-substituted ethyl group having 7 to 18 carbon atoms is preferable.
  • a substituted ethyl group of 16 is more preferred.
  • 1-substituted ethyl group examples include, but are not limited to, 1-methoxyethyl group, 1-methylthioethyl group, 1,1-dimethoxyethyl group, 1-ethoxyethyl group, 1-ethylthioethyl group, 1,1-diethoxyethyl group, n-propoxyethyl group, isopropoxyethyl group, n-butoxyethyl group, t-butoxyethyl group, 2-methylpropoxyethyl group, 1-phenoxyethyl group, 1-phenylthioethyl Group, 1,1-diphenoxyethyl group, 1-cyclopentyloxyethyl group, 1-cyclohexyloxyethyl group, 1-phenylethyl group, 1,1-diphenylethyl group, and represented by the following formula (1-2). Examples include a group of substituents.
  • R 10 has the same meaning as the formula (1-1).
  • the 1-substituted-n-propyl group is not particularly limited, but can be usually a 1-substituted-n-propyl group having 4 to 20 carbon atoms and a 1-substituted-n-propyl group having 6 to 18 carbon atoms.
  • a propyl group is preferable, and a 1-substituted-n-propyl group having 8 to 16 carbon atoms is more preferable.
  • Specific examples of the 1-substituted-n-propyl group include, but are not limited to, 1-methoxy-n-propyl group and 1-ethoxy-n-propyl group.
  • the 1-branched alkyl group is not particularly limited, but usually, it can be a 1-branched alkyl group having 3 to 20 carbon atoms, a 1-branched alkyl group having 5 to 18 carbon atoms is preferable, and a 1-branched alkyl group having 7 to 18 carbon atoms is preferable. 16 branched alkyl groups are more preferred. Specific examples of the 1-branched alkyl group include, but are not limited to, an isopropyl group, a sec-butyl group, a tert-butyl group, a 1,1-dimethylpropyl group, a 1-methylbutyl group, and a 1,1-dimethylbutyl group. , 2-Methyl adamantyl group, 2-ethyl adamantyl group and the like.
  • the 1-substituted alkoxymethyl group is not particularly limited, but usually it can be a 1-substituted alkoxymethyl group having 2 to 20 carbon atoms, and a 1-substituted alkoxymethyl group having 4 to 18 carbon atoms is preferable.
  • the 1-substituted alkoxymethyl group of numbers 6 to 16 is more preferable.
  • Specific examples of the 1-substituted alkoxymethyl group are not limited to the following, but are limited to 1-cyclopentylmethoxymethyl group, 1-cyclopentylethoxymethyl group, 1-cyclohexylmethoxymethyl group, 1-cyclohexylethoxymethyl group and 1-cyclooctyl. Examples thereof include a methoxymethyl group and a 1-adamantyl methoxymethyl group.
  • the alkoxycarbonylalkyl group is not particularly limited, but usually, it can be an alkoxycarbonylalkyl group having 3 to 20 carbon atoms, preferably an alkoxycarbonylalkyl group having 4 to 18 carbon atoms, and an alkoxy having 6 to 16 carbon atoms.
  • a carbonylalkyl group is more preferred.
  • Specific examples of the alkoxycarbonylalkyl group include, but are not limited to, a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxycarbonylmethyl group, an isopropoxycarbonylmethyl group, an n-butoxycarbonylmethyl group, or the following formula (1).
  • R 11 is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, and n is an integer of 0 to 4.
  • the cycloalkane having 3 to 12 carbon atoms may be monocyclic or polycyclic, but is preferably polycyclic. Specific examples of the cycloalkane having 3 to 12 carbon atoms are not limited to the following, but include, but are not limited to, monocycloalkane, bicycloalkane, tricycloalkane, tetracycloalkane, and the like. , Cyclopropane, cyclobutane, cyclopentane, cyclohexane and other monocycloalkanes, and polycycloalkanes such as adamantan, norbornane, isobornane, tricyclodecane and tetracyclodecane.
  • adamantane, tricyclodecane and tetracyclodecane are preferable, and adamantane and tricyclodecane are more preferable.
  • Cycloalkanes having 3 to 12 carbon atoms may have a substituent.
  • the lactone include, but are not limited to, butyrolactone or cycloalkane having a lactone group and having 3 to 12 carbon atoms.
  • the "crosslinkable group” refers to a group that reacts in the presence of a radical or acid / alkali and whose solubility in an acid, alkali or organic solvent used in a coating solvent or a developing solution changes.
  • a radical or acid / alkali whose solubility in an acid, alkali or organic solvent used in a coating solvent or a developing solution changes.
  • an allyl group, a (meth) acryloyl group, a vinyl group, an epoxy group, an alkoxymethyl group, or a cyano group is preferable from the viewpoint of crosslinkability.
  • the crosslinkable group preferably has a property of causing a chain cleavage reaction in the presence of an acid.
  • R 2 is the formula (Z-1), (Z -2) as synonymous .
  • R 3 ' is a divalent group of a substituted or unsubstituted 1 to 22 carbon atoms Is.
  • R 3' refers to, for example, a linear alkylene group having 1 to 22 substituted or unsubstituted carbon atoms, a branched alkylene group having 3 to 22 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon number 3 It can be a cyclic alkylene group of ⁇ 22 or an arylene group having 6 to 22 carbon atoms substituted or unsubstituted.
  • the resin according to the present embodiment has a plurality of the above formulas (Z-1) to (Z-3) in which at least one of R 2 of the formulas (Z-1) to (Z-3) is a crosslinkable group.
  • Examples of the structural unit represented by the formula (A-3) in which R 6 contains an ester bond include the structural unit represented by the following formula (A-3-2).
  • R 6 ′′ is a substituted or unsubstituted divalent group having 1 to 20 carbon atoms.
  • R 0 is synonymous with the above formula (X-2).
  • R 6 ′′ is, for example, a linear alkylene group having 1 to 20 carbon atoms substituted or unsubstituted, a branched alkylene group having 3 to 20 carbon atoms substituted or unsubstituted, and a substituted or unsubstituted carbon number. It can be a cyclic alkylene group of 3 to 20 or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted.
  • Examples of the linear alkylene group having 1 to 20 carbon atoms include a methylene group, an ethylene group and a propylene group.
  • Examples of the branched alkylene group having 3 to 20 carbon atoms include an isopropylene group.
  • Examples of the cyclic alkylene group having 3 to 20 carbon atoms include a cyclohexylene group and the like.
  • Examples of the arylene group having 6 to 20 carbon atoms include a phenylene group and a naphthylene group.
  • the substituent may be similar to the substituents for R 4 in the formula (a-1).
  • Examples of X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • one or more mineral acid aqueous solutions selected from the group consisting of hydrochloric acid, sulfuric acid, nitrate and phosphoric acid, or acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, It is preferably one or more organic acid aqueous solutions selected from the group consisting of tartrate acid, citric acid, methanesulfonic acid, phenolsulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid, preferably sulfuric acid, nitric acid, and acetic acid, oxalic acid.
  • the method of adding an organic solvent that is arbitrarily miscible with water is not particularly limited.
  • any of a method of adding to a solution containing an organic solvent in advance, a method of adding to water or an acidic aqueous solution in advance, and a method of adding after contacting a solution containing an organic solvent with water or an acidic aqueous solution may be used.
  • the method of adding to a solution containing an organic solvent in advance is preferable in terms of workability of operation and ease of control of the amount to be charged.
  • the temperature at the time of contact between the solution (A) and the acidic aqueous solution is preferably 20 to 90 ° C, more preferably 30 to 80 ° C.
  • the extraction operation is not particularly limited, but is performed by, for example, mixing the solution (A) and an acidic aqueous solution well by stirring or the like, and then allowing the obtained mixed solution to stand.
  • the metal content contained in the solution (A) containing one or more selected from the compounds and resins according to the present embodiment and the organic solvent is transferred to the aqueous phase. Further, by this operation, the acidity of the solution (A) is lowered, and the alteration of the compound or resin according to the present embodiment can be suppressed.
  • a solution containing one or more selected from the compounds and resins according to the present embodiment extracted and recovered from the aqueous solution after performing the extraction treatment using an acidic aqueous solution, and an organic solvent. It is preferable that the phase is further subjected to an extraction treatment with water.
  • the extraction treatment with water is not particularly limited, but can be performed, for example, by mixing the solution phase and water well by stirring or the like, and then allowing the obtained mixed solution to stand.
  • the mixed solution after standing is separated into a solution phase containing one or more selected from the compounds and resins according to the present embodiment and an organic solvent, and an aqueous phase.
  • a solution phase containing one or more selected from compounds and resins and an organic solvent can be recovered.
  • the water used here is preferably water having a low metal content, for example, ion-exchanged water, etc., in line with the purpose of the present embodiment.
  • the extraction process may be performed only once, but it is also effective to repeat the operations of mixing, standing, and separating a plurality of times.
  • the conditions such as the ratio of use of both in the extraction treatment, temperature, and time are not particularly limited, but the same as in the case of the contact treatment with the acidic aqueous solution described above may be used.
  • the method for isolating one or more selected from the compounds and resins according to the present embodiment from the obtained solution containing one or more selected from the compounds and resins according to the present embodiment and an organic solvent is not particularly limited. , Removal under reduced pressure, separation by reprecipitation, and a combination thereof, etc., can be carried out by known methods. If necessary, known treatments such as concentration operation, filtration operation, centrifugation operation, and drying operation can be performed.
  • the lithography material according to the present embodiment contains the compound or resin according to the present embodiment.
  • the lithography material according to the present embodiment is a material that can be used in the lithography technology, and is not particularly limited as long as it contains the compound or resin according to the present embodiment. It can be used as a composition, and can also be used for resist applications (that is, resist compositions) and the like.
  • the lithographic material composition according to the present embodiment includes the lithographic material according to the present embodiment and a solvent. Since the material composition for lithography has high sensitivity and the compound or resin according to the present embodiment is sufficiently dissolved in a solvent, a good resist pattern shape can be imparted. For example, a resist film can be formed from a material composition for lithography.
  • the dissolution rate of the amorphous film formed by spin-coating the lithographic material composition of the present embodiment in a developing solution at 23 ° C. is 5 ⁇ / sec or less. Is preferable, 0.05 to 5 ⁇ / sec is more preferable, and 0.0005 to 5 ⁇ / sec is even more preferable.
  • the dissolution rate is 5 ⁇ / sec or less, a resist insoluble in a developing solution can be obtained. Further, when the dissolution rate is 0.0005 ⁇ / sec or more, the resolution may be improved.
  • the dissolution rate of the amorphous film formed by spin-coating the lithographic material composition of the present embodiment in a developing solution at 23 ° C. is 10 ⁇ / sec or more. Is preferable. When the dissolution rate is 10 ⁇ / sec or more, it is easily dissolved in a developing solution and is more suitable for a resist. Further, when the dissolution rate is 10 ⁇ / sec or more, the resolution may be improved. It is presumed that this is because the micro surface portion of the compound or resin according to the present embodiment is dissolved and the line edge roughness is reduced. It also has the effect of reducing defects.
  • the dissolution rate can be determined by immersing the amorphous film in a developer for a predetermined time at 23 ° C. and measuring the film thickness before and after the immersion by a known method such as visual inspection, ellipsometer or QCM method.
  • an amorphous film KrF excimer laser, extreme ultraviolet rays, electron beams, X-rays, or the like formed by spin-coating the lithography material composition of the present embodiment may be used.
  • the dissolution rate of the radiation-exposed portion in the developing solution at 23 ° C. is preferably 10 ⁇ / sec or more.
  • the dissolution rate is 10 ⁇ / sec or more, it is easily dissolved in a developing solution and is more suitable for a resist.
  • the dissolution rate is 10 ⁇ / sec or more, the resolution may be improved. It is presumed that this is because the micro surface portion of the compound or resin according to the present embodiment is dissolved and the line edge roughness is reduced. It also has the effect of reducing defects.
  • the lithography material composition of the present embodiment is a negative resist pattern
  • an amorphous film KrF excimer laser, extreme ultraviolet rays, electron beam, X-ray or the like formed by spin coating the lithography material composition of the present embodiment may be used.
  • the dissolution rate of the radiation-exposed portion in the developing solution at 23 ° C. is preferably 5 ⁇ / sec or less, more preferably 0.05 to 5 ⁇ / sec, still more preferably 0.0005 to 5 ⁇ / sec.
  • the dissolution rate is 5 ⁇ / sec or less, a resist insoluble in a developing solution can be obtained. Further, when the dissolution rate is 0.0005 ⁇ / sec or more, the resolution may be improved.
  • the lithographic material composition of the present embodiment contains the compound or resin according to the present embodiment as a solid component.
  • the lithographic material composition of the present embodiment further contains a solvent in addition to the compound or resin according to the present embodiment.
  • the solvent used in the material composition for lithography of the present embodiment is not particularly limited, and for example, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol mono- Ethylene glycol monoalkyl ether acetates such as n-butyl ether acetate; ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate (PGMEA), propylene Propropylene glycol monoalkyl ether acetates such as glycol mono-n-propyl ether acetate and propylene glycol mono-n-butyl ether acetate; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether (PGME) and prop
  • the solvent used in the lithography material composition of the present embodiment is preferably a safe solvent, more preferably PGMEA, PGME, CHN, CPN, 2-heptanone, anisole, butyl acetate, ethyl propionate and lactic acid. At least one selected from ethyl, more preferably at least one selected from PGMEA, PGME and CHN.
  • the relationship between the amount of the solid component and the amount of the solvent is not particularly limited, but is 1 to 80% by mass of the solid component with respect to 100% by mass of the total mass of the solid component and the solvent.
  • the solvent is preferably 20 to 99% by mass, more preferably 1 to 50% by mass of the solid component and 50 to 99% by mass of the solvent, still more preferably 2 to 40% by mass of the solid component and 60 to 98% by mass of the solvent.
  • the solid component is 2 to 10% by mass and the solvent is 90 to 98% by mass.
  • the material composition for lithography of the present embodiment is selected from the group consisting of an acid generator (C), an acid cross-linking agent (G), an acid diffusion control agent (E), and other components (F) as other solid components. May contain at least one of these.
  • the content of the compound or resin according to the present embodiment is not particularly limited, but the total mass of the solid component (the compound or resin according to the present embodiment, the acid generator (C)).
  • the sum of the solid components arbitrarily used such as the acid cross-linking agent (G), the acid diffusion control agent (E) and the other component (F), the same applies hereinafter) is preferably 50 to 99.4% by mass. , More preferably 55 to 90% by mass, still more preferably 60 to 80% by mass, and particularly preferably 60 to 70% by mass.
  • the resolution is further improved and the line edge roughness (LER) is further reduced.
  • the lithographic material composition of the present embodiment is directly or indirectly acid by irradiation with any radiation selected from visible light, ultraviolet light, excimer laser, electron beam, extreme ultraviolet light (EUV), X-ray and ion beam. It is preferable to contain one or more acid generators (C) that generate the above.
  • the content of the acid generator (C) is preferably 0.001 to 49% by mass, more preferably 1 to 40% by mass, based on the total mass of the solid components. 3 to 30% by mass is more preferable, and 10 to 25% by mass is particularly preferable.
  • the method of generating the acid is not limited. Finer processing is possible by using an excimer laser instead of ultraviolet rays such as g-rays and i-rays, and further fine processing is possible by using electron beams, extreme ultraviolet rays, X-rays, and ion beams as high-energy rays. Is possible.
  • the acid generator (C) is not particularly limited, and examples thereof include compounds disclosed in International Publication No. 2017/033943.
  • an acid generator having an aromatic ring is preferable, an acid generator having a sulfonic acid ion having an aryl group is more preferable, and diphenyltrimethylphenylsulfonium p-toluenesulfonate and triphenylsulfonium p-toluene are preferable.
  • Sulfonate, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoromethanesulfonate are particularly preferable.
  • the material composition for lithography of the present embodiment further contains a diazonaphthoquinone photoactive compound as an acid generator.
  • the diazonaphthoquinone photoactive compound is a diazonaphthoquinone substance containing a polymeric and non-polymeric diazonaphthoquinone photoactive compound, and is particularly limited as long as it is generally used as a photosensitive component in a positive resist composition. However, one type or two or more types can be arbitrarily selected and used.
  • the lithographic material composition of the present embodiment contains one or more acid cross-linking agents (G) when used as a negative resist material or as an additive for increasing the strength of a pattern even in a positive resist material. Is preferable.
  • the acid cross-linking agent (G) is a compound capable of intramolecularly or intermolecularly cross-linking the compound or resin according to the present embodiment in the presence of an acid generated from the acid generator (C).
  • Such an acid cross-linking agent (G) is not particularly limited, and examples thereof include a compound according to the present embodiment or a compound having one or more cross-linking groups capable of cross-linking a resin.
  • crosslinkable group examples are not particularly limited, but for example, (i) hydroxy (alkyl group having 1 to 6 carbon atoms), alkoxy having 1 to 6 carbon atoms (alkyl group having 1 to 6 carbon atoms). , Hydroxyalkyl groups such as acetoxy (alkyl groups having 1 to 6 carbon atoms) or groups derived from them; (ii) Formyl groups, carbonyl groups such as carboxy (alkyl groups having 1 to 6 carbon atoms) or derived from them.
  • Groups derived from aromatic groups such as oxy (alkyl groups having 1 to 6 carbon atoms); (vi) polymerizable multiple bond-containing groups such as vinyl groups and isopropenyl groups can be mentioned.
  • the crosslinkable group of the acid cross-linking agent (G) a hydroxyalkyl group, an alkoxyalkyl group and the like are preferable, and an alkoxymethyl group is particularly preferable.
  • the acid cross-linking agent (G) having a cross-linking group is not particularly limited, and for example, (i) a methylol group-containing melamine compound, a methylol group-containing benzoguanamine compound, a methylol group-containing urea compound, a methylol group-containing glycol uryl compound, and methylol.
  • Methyl group-containing compounds such as group-containing phenol compounds; (ii) alkoxyalkyl group-containing melamine compounds, alkoxyalkyl group-containing benzoguanamine compounds, alkoxyalkyl group-containing urea compounds, alkoxyalkyl group-containing glycol uryl compounds, alkoxyalkyl group-containing phenol compounds, etc.
  • Carboxymethyl group such as carboxymethyl group-containing melamine compound, carboxymethyl group-containing benzoguanamine compound, carboxymethyl group-containing urea compound, carboxymethyl group-containing glycoluril compound, and carboxymethyl group-containing phenol compound. Containing compounds; (iv) bisphenol A-based epoxy compounds, bisphenol F-based epoxy compounds, bisphenol S-based epoxy compounds, novolak resin-based epoxy compounds, resole resin-based epoxy compounds, poly (hydroxystyrene) -based epoxy compounds and other epoxy compounds. Can be mentioned.
  • the acid cross-linking agent (G) a compound having a phenolic hydroxyl group and a compound and a resin obtained by introducing the cross-linking group into an acidic functional group in an alkali-soluble resin to impart cross-linking property can be used. ..
  • the introduction rate of the crosslinkable group is not particularly limited, and is, for example, 5 to 100 mol%, preferably 10 to 60, based on the total acidic functional group in the compound having a phenolic hydroxyl group and the alkali-soluble resin. It is adjusted to mol%, more preferably 15-40 mol%. Within the above range, the cross-linking reaction occurs sufficiently, and a decrease in the residual film ratio, a pattern swelling phenomenon, meandering, and the like can be avoided, which is preferable.
  • the acid cross-linking agent (G) is an alkoxyalkylated urea compound or a resin thereof, an alkoxyalkylated glycol uryl compound or a resin thereof (acid cross-linking agent (G1)), and benzene in the molecule.
  • Agent (G2)) a compound having at least one ⁇ -hydroxyisopropyl group (acid cross-linking agent (G3)) is preferable.
  • the compounds disclosed in International Publication No. 2017/033943 can be mentioned.
  • the content of the acid cross-linking agent (G) is preferably 0.5 to 49% by mass, more preferably 0.5 to 40% by mass, based on the total mass of the solid components. It is more preferably from 30% by mass, particularly preferably from 2 to 20% by mass.
  • the content ratio of the acid cross-linking agent (G) is 0.5% by mass or more, the effect of suppressing the solubility of the resist film in the alkaline developer is improved, the residual film ratio is lowered, and the pattern is swollen or tortuous. It is preferable because it can suppress the occurrence, and on the other hand, when it is 49% by mass or less, it is preferable because a decrease in heat resistance as a resist can be suppressed.
  • the content of at least one compound selected from the acid cross-linking agent (G1), the acid cross-linking agent (G2), and the acid cross-linking agent (G3) in the acid cross-linking agent (G) is not particularly limited.
  • the range can be various depending on the type of the substrate used when forming the resist pattern and the like.
  • the material composition for lithography of the present embodiment controls the diffusion of the acid generated from the acid generator by irradiation in the resist film, and has an action of preventing an unfavorable chemical reaction in an unexposed region.
  • the control agent (E) may be contained.
  • the storage stability of the material composition for lithography is improved.
  • the resolution is further improved, and changes in the line width of the resist pattern due to fluctuations in the retention time before irradiation and the retention time after irradiation can be suppressed, resulting in extremely excellent process stability.
  • Such an acid diffusion control agent (E) is not particularly limited, and examples thereof include radiodegradable basic compounds such as nitrogen atom-containing basic compounds, basic sulfonium compounds, and basic iodonium compounds.
  • radiodegradable basic compounds such as nitrogen atom-containing basic compounds, basic sulfonium compounds, and basic iodonium compounds.
  • Examples of the acid diffusion control agent (E) include compounds disclosed in International Publication No. 2017/033943.
  • the acid diffusion control agent (E) may be used alone or in combination of two or more.
  • the content of the acid diffusion control agent (E) is preferably 0.001 to 49% by mass, more preferably 0.01 to 10% by mass, still more preferably 0.01 to 5% by mass, based on the total mass of the solid components. 0.01 to 3% by mass is particularly preferable.
  • the content of the acid diffusion control agent (E) is within the above range, deterioration of resolution, pattern shape, dimensional fidelity and the like can be further suppressed. Further, even if the leaving time from the electron beam irradiation to the heating after the irradiation is long, the shape of the upper layer portion of the pattern does not deteriorate.
  • the content of the acid diffusion control agent (E) is 10% by mass or less, it is possible to prevent deterioration of sensitivity, developability of the unexposed portion and the like. Further, by using such an acid diffusion control agent, the storage stability of the material composition for lithography is improved, the resolution is improved, and the retention time before irradiation and the retention time after irradiation are increased. It is possible to suppress changes in the line width of the resist pattern due to fluctuations, and the process stability is extremely excellent.
  • a dissolution accelerator In the material composition for lithography of the present embodiment, a dissolution accelerator, a dissolution control agent, a sensitizer, and a surfactant are used as other components (F), if necessary, as long as the object of the present embodiment is not impaired.
  • One or two or more kinds of additives such as an agent and an organic carboxylic acid or an oxo acid of phosphorus or a derivative thereof can be added.
  • the other component (F) include compounds disclosed in International Publication No. 2017/033943.
  • the total content of the other component (F) is preferably 0 to 49% by mass, more preferably 0 to 5% by mass, further preferably 0 to 1% by mass, and particularly preferably 0% by mass, based on the total mass of the solid component. ..
  • the compound or resin / acid generator (C) / acid diffusion control agent (E) / other component (F)) is in mass% based on the solid matter, preferably 50 to 99.4 / 0.001 to 49 /. 0.001 to 49/0 to 49, more preferably 55 to 90/1 to 40/0.01 to 10/0 to 5, still more preferably 60 to 80/3 to 30/0.01 to 5/0 to 1, particularly preferably 60 to 70/10 to 25/0.01 to 3/0.
  • the content ratio of each component is selected from each range so that the total is 100% by mass. With the above content ratio, the performance such as sensitivity, resolution, and developability is further excellent.
  • the method for preparing the material composition for lithography of the present embodiment is not particularly limited.
  • each component is dissolved in a solvent at the time of use to obtain a uniform solution, and then, if necessary, a filter having a pore size of, for example, about 0.2 ⁇ m.
  • a method of filtering with or the like can be mentioned.
  • the lithographic material composition of the present embodiment may contain other resins as long as the object of the present invention is not impaired.
  • Other resins are not particularly limited, and include, for example, novolak resin, polyvinylphenols, polyacrylic acid, polyvinyl alcohol, styrene-maleic anhydride resin, and acrylic acid, vinyl alcohol, or vinylphenol as a monomer unit. Examples thereof include polymers and derivatives thereof.
  • the content of the resin is not particularly limited and is appropriately adjusted according to the type of the compound or resin according to the present embodiment to be used, but is preferably 30 parts by mass or less, more preferably 30 parts by mass or less per 100 parts by mass of the compound. It is 10 parts by mass or less, more preferably 5 parts by mass or less, and particularly preferably 0 parts by mass.
  • a pattern formation method When a pattern is formed on a substrate using a lithographic material, for example, a lithographic material according to the present embodiment and a composition containing the same (hereinafter, these may be collectively referred to as "lithographic material or the like").
  • a pattern forming method including a film forming step of forming a film on a substrate by using, an exposure step of exposing the film, and a developing step of developing the exposed film in the exposure step to form a pattern is used. be able to.
  • the method for forming the pattern is not particularly limited, and as a suitable method, a resist composition containing the above-mentioned lithography material or the like is used.
  • a film forming step of applying an object onto a substrate to form a film (resist film), an exposure step of exposing the formed film (resist film), and a film (resist film) exposed in the exposure step are developed.
  • a method including a developing step of forming a pattern (resist pattern) can be mentioned.
  • the resist pattern of this embodiment can also be formed as an upper layer resist in a multilayer process.
  • the method for forming a specific resist pattern is not particularly limited, and examples thereof include the following methods.
  • a resist film is formed by applying the resist composition onto a conventionally known substrate by coating means such as rotary coating, casting coating, and roll coating.
  • the conventionally known substrate is not particularly limited, and examples thereof include a substrate for electronic components and a substrate on which a predetermined wiring pattern is formed. More specifically, the present invention is not particularly limited, and examples thereof include a silicon wafer, a metal substrate such as copper, chromium, iron, and aluminum, and a glass substrate.
  • the material of the wiring pattern is not particularly limited, and examples thereof include copper, aluminum, nickel, and gold. Further, if necessary, an inorganic film or an organic film may be provided on the above-mentioned substrate.
  • the inorganic film is not particularly limited, and examples thereof include an inorganic antireflection film (inorganic BARC).
  • the organic film is not particularly limited, and examples thereof include an organic antireflection film (organic BARC). Surface treatment with hexamethylene disilazane or the like may be performed.
  • the heating conditions vary depending on the content of the resist composition and the like, but are preferably 20 to 250 ° C, more preferably 20 to 150 ° C. By heating, the adhesion of the resist to the substrate may be improved, which is preferable.
  • the resist film is then exposed to a desired pattern with any radiation selected from the group consisting of visible light, ultraviolet light, excimer lasers, electron beams, extreme ultraviolet light (EUV), X-rays, and ion beams.
  • the exposure conditions and the like are appropriately selected according to the compounding composition of the resist composition and the like.
  • the heating conditions vary depending on the composition of the resist composition and the like, but are preferably 20 to 250 ° C, more preferably 20 to 150 ° C.
  • a predetermined resist pattern is formed by developing the exposed resist film with a developing solution.
  • a developing solution it is preferable to select a solvent having a solubility parameter (SP value) close to that of the compound or resin according to the present embodiment to be used, and a ketone solvent, an ester solvent, an alcohol solvent, or an amide solvent.
  • Polar solvents such as ether solvents, hydrocarbon solvents or alkaline aqueous solutions can be used.
  • a positive resist pattern or a negative resist pattern can be prepared depending on the type of the developing solution, but generally, a polar solvent such as a ketone solvent, an ester solvent, an alcohol solvent, an amide solvent, or an ether solvent is used.
  • a negative resist pattern can be obtained, and in the case of an alkaline aqueous solution, a positive resist pattern can be obtained.
  • the ketone solvent, ester solvent, alcohol solvent, amide solvent, ether solvent, hydrocarbon solvent, and alkaline aqueous solution include those disclosed in International Publication No. 2017/033943.
  • a plurality of the solvents may be mixed, or may be mixed with a solvent or water other than the above as long as the solvent has performance.
  • the water content of the developer as a whole is preferably less than 70% by mass, more preferably less than 50% by mass, and more preferably less than 30% by mass. It is preferably less than 10% by mass, and particularly preferably substantially free of water. That is, the content of the organic solvent in the developing solution is not particularly limited, and is preferably 30% by mass or more and 100% by mass or less, and more preferably 50% by mass or more and 100% by mass or less with respect to the total amount of the developing solution. It is more preferably 70% by mass or more and 100% by mass or less, further preferably 90% by mass or more and 100% by mass or less, and particularly preferably 95% by mass or more and 100% by mass or less.
  • the developing solution contains at least one solvent selected from a ketone solvent, an ester solvent, an alcohol solvent, an amide solvent and an ether solvent, and the developing solution contains the resolution and roughness of the resist pattern. It is preferable because it improves the resist performance of the solvent.
  • the vapor pressure of the developing solution is not particularly limited, and for example, at 20 ° C., 5 kPa or less is preferable, 3 kPa or less is further preferable, and 2 kPa or less is particularly preferable.
  • 5 kPa or less By reducing the vapor pressure of the developer to 5 kPa or less, evaporation of the developer on the substrate or in the developing cup is suppressed, the temperature uniformity in the wafer surface is improved, and as a result, the dimensional uniformity in the wafer surface is improved. Improve.
  • Examples of the developer having such a vapor pressure include the developer disclosed in International Publication No. 2017/033943.
  • the surfactant is not particularly limited, and for example, an ionic or nonionic fluorine-based or silicon-based surfactant can be used.
  • fluorine- or silicon-based surfactants include Japanese Patent Application Laid-Open No. 62-36663, Japanese Patent Application Laid-Open No. 61-226746, Japanese Patent Application Laid-Open No. 61-226745, and Japanese Patent Application Laid-Open No. 62-170950.
  • Kaisho 63-34540 Japanese Patent Application Laid-Open No. 7-230165, Japanese Patent Application Laid-Open No. 8-62834, Japanese Patent Application Laid-Open No.
  • the surfactants described in No. 5,259881, No. 5296330, No. 5436098, No. 5576143, No. 5294511, and No. 5824451 can be mentioned.
  • it is a nonionic surfactant.
  • the nonionic surfactant is not particularly limited, but it is more preferable to use a fluorine-based surfactant or a silicon-based surfactant.
  • the amount of the surfactant used is usually 0.001 to 5% by mass, preferably 0.005 to 2% by mass, and more preferably 0.01 to 0.5% by mass with respect to the total amount of the developing solution.
  • Examples of the developing method include a method of immersing the substrate in a tank filled with a developing solution for a certain period of time (dip method), and a method of developing by raising the developing solution on the surface of the substrate by surface tension and allowing it to stand still for a certain period of time (paddle).
  • dip method a method of immersing the substrate in a tank filled with a developing solution for a certain period of time
  • piddle a method of developing by raising the developing solution on the surface of the substrate by surface tension and allowing it to stand still for a certain period of time
  • Method a method of spraying the developer on the surface of the substrate
  • spray method a method of continuing to apply the developer on the substrate rotating at a constant speed while scanning the developer application nozzle at a constant speed
  • Etc. can be applied.
  • the time for developing the pattern is not particularly limited, but is preferably 10 seconds to 90 seconds.
  • a step of stopping the development may be carried out while substituting with another solvent.
  • the rinsing solution used in the rinsing step after development is not particularly limited as long as the resist pattern cured by crosslinking is not dissolved, and a solution or water containing a general organic solvent can be used.
  • a rinsing solution it is preferable to use a rinsing solution containing at least one organic solvent selected from a hydrocarbon solvent, a ketone solvent, an ester solvent, an alcohol solvent, an amide solvent and an ether solvent. .. More preferably, after the development, a washing step is performed using a rinsing solution containing at least one organic solvent selected from the group consisting of a ketone solvent, an ester solvent, an alcohol solvent, and an amide solvent.
  • a step of washing with a rinsing solution containing an alcohol-based solvent or an ester-based solvent is performed. Even more preferably, after development, a step of washing with a rinsing solution containing a monohydric alcohol is performed. Particularly preferably, after the development, a step of washing with a rinsing solution containing a monohydric alcohol having 5 or more carbon atoms is performed.
  • the time for rinsing the pattern is not particularly limited, but is preferably 10 seconds to 90 seconds.
  • the monohydric alcohol used in the rinsing step after development is not particularly limited, and examples thereof include linear, branched, and cyclic monohydric alcohols, and specifically, 1-butanol and 2 -Butanol, 3-methyl-1-butanol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 1-hexanol, 4-methyl-2-pentanol, 1-heptanol, 1-octanol, 2-hexanol , Cyclopentanol, 2-Heptanol, 2-Octanol, 3-Hexanol, 3-Heptanol, 3-Octanol, 4-Octanol and the like can be used, and a particularly preferable monohydric alcohol having 5 or more carbon atoms is 1-. Hexanol, 2-hexanol, 4-methyl-2-pentanol, 1-pentanol, 3-methyl-1-butanol and the like can be
  • a plurality of each of the above components may be mixed, or may be mixed and used with an organic solvent other than the above.
  • the water content in the rinse liquid is not particularly limited, and is preferably 10% by mass or less, more preferably 5% by mass or less, and particularly preferably 3% by mass or less. By setting the water content to 10% by mass or less, better development characteristics can be obtained.
  • the vapor pressure of the rinse solution used after development is preferably 0.05 kPa or more and 5 kPa or less, more preferably 0.1 kPa or more and 5 kPa or less, and further preferably 0.12 kPa or more and 3 kPa or less at 20 ° C.
  • An appropriate amount of surfactant can be added to the rinse solution before use.
  • the cleaning treatment method is not particularly limited, but for example, a method of continuously spraying the rinse liquid on a substrate rotating at a constant speed (rotary coating method), or immersing the substrate in a tank filled with the rinse liquid for a certain period of time.
  • a method (dip method), a method of spraying a rinse solution on the surface of the substrate (spray method), etc. can be applied.
  • the cleaning treatment is performed by the rotary coating method, and after cleaning, the substrate is rotated at a rotation speed of 2000 rpm to 4000 rpm. It is preferable to rotate and remove the rinse liquid from the substrate.
  • a pattern wiring board can be obtained by etching after forming a resist pattern.
  • the etching method can be performed by a known method such as dry etching using plasma gas and wet etching with an alkaline solution, a cupric chloride solution, a ferric chloride solution or the like.
  • Plating can also be performed after forming the resist pattern.
  • the plating method is not particularly limited, and examples thereof include copper plating, solder plating, nickel plating, and gold plating.
  • the residual resist pattern after etching can be peeled off with an organic solvent.
  • the organic solvent is not particularly limited, and examples thereof include PGMEA (propylene glycol monomethyl ether acetate), PGME (propylene glycol monomethyl ether), and EL (ethyl lactate).
  • the peeling method is not particularly limited, and examples thereof include a dipping method and a spray method.
  • the wiring board on which the resist pattern is formed may be a multi-layer wiring board or may have a small-diameter through hole.
  • the wiring board can also be formed by a method of depositing a metal in vacuum after forming a resist pattern and then dissolving the resist pattern with a solution, that is, a lift-off method.
  • composition for forming an underlayer film for lithography or forming an optical article contains ascorbic acid or a derivative thereof, or a structural unit derived from ascorbic acid or a derivative thereof. Contains resin.
  • the resin containing ascorbic acid or a derivative thereof or a structural unit derived from ascorbic acid or a derivative thereof according to the present embodiment contains a polar group such as a hydroxyl group, and therefore has high solubility in a solvent. Further, since the solution of the resin containing ascorbic acid or a derivative thereof or the structural unit derived from ascorbic acid or a derivative thereof according to the present embodiment has a low viscosity, a composition containing these is used to form a lower layer film for lithography. When formed, a highly flat underlayer film is obtained.
  • the resin containing ascorbic acid or a derivative thereof or a structural unit derived from ascorbic acid or a derivative thereof according to the present embodiment is amorphous, when an optical article is formed using a composition containing these. , A highly transparent optical article can be obtained.
  • the chemical structure of ascorbic acid or its derivative or resin according to this embodiment can be confirmed by 1 1 H-NMR measurement and IR measurement.
  • the “derivative of ascorbic acid” refers to one containing a ring-opened body of ascorbic acid and a derivative thereof, and containing 1 or 2 structural units derived from ascorbic acid.
  • the derivative of ascorbic acid may be a mixture of isomers.
  • the “resin” refers to a resin containing three or more structural units derived from ascorbic acid.
  • the derivative of ascorbic acid at least one of the hydroxyl groups of ascorbic acid is substituted with another substituent, the ring-opened body of ascorbic acid, and at least one of the hydroxyl groups of the ring-opened body of ascorbic acid is substituted with another substituent.
  • substituents include the compounds used.
  • Examples of the ascorbic acid derivative in the composition according to the present embodiment include the above-mentioned compounds according to the present embodiment. Specifically, the compound represented by the formula (X-1), the compound represented by the formula (Y), the compound represented by the formula (Z-1), (Z-2), or (Z-3). Examples include compounds. Examples of the resin in the composition according to the present embodiment include the above-mentioned resin according to the present embodiment.
  • composition for forming an underlayer film for lithography comprises ascorbic acid or a derivative or resin thereof according to the present embodiment and a silicon-containing compound (for example, hydrolyzable organosilane, a hydrolyzate thereof). Or a hydrolyzed derivative thereof), and a composition for forming an underlayer film for lithography.
  • the composition for forming a lower layer film for lithography of the present embodiment can form a lower layer film for lithography such as a resist underlayer film, has high heat resistance, and has high solvent solubility. Therefore, the rectangularity of the pattern is excellent. In addition, it is possible to reduce film defects (thin film formation), have high adhesion, have good storage stability, have high sensitivity, long-term light resistance, and can impart a good resist pattern shape. Further, the composition for forming a lower layer film for lithography of the present embodiment can form a lower layer film for lithography having high flatness.
  • the composition for forming a lower layer film for lithography of the present embodiment is suitably used for, for example, a multilayer resist method in which a resist lower layer film is further provided between an upper layer resist (photoresist or the like) and a hard mask, an organic lower layer film, or the like.
  • a multilayer resist method for example, a resist underlayer film is formed on an organic underlayer film or a hard mask on a substrate by a coating method or the like, and an upper layer resist (for example, photoresist, etc.) is formed on the resist underlayer film.
  • An electron beam resist, an EUV resist is formed.
  • a resist pattern is formed by exposure and development, the resist underlayer film is dry-etched using the resist pattern to transfer the pattern, and the pattern is transferred by etching the organic underlayer film, and the organic underlayer film transfers the pattern. Process the substrate.
  • the lithography lower layer film (resist lower layer film) formed by using the lithography lower layer film forming composition of the present embodiment is less likely to cause intermixing with the upper layer resist and has heat resistance, for example. Since the etching rate for halogen-based (fluorine-based) etching gas is higher than that of the patterned upper-layer resist used as a mask, a good pattern can be obtained in a rectangular shape. Further, since the lithography underlayer film (resist underlayer film) formed by using the lithography underlayer film forming composition of the present embodiment has high resistance to oxygen-based etching gas, it is provided on a substrate such as a hard mask. It can function as a good mask when patterning layers.
  • the composition for forming an underlayer film for lithography of the present embodiment can also be used in an embodiment in which a plurality of resist underlayer films are laminated.
  • the position (how many layers are laminated) of the resist lower layer film formed by using the composition for forming the lower layer film for lithography of the present embodiment is not particularly limited, and even if it is directly under the upper layer resist.
  • the layer may be located closest to the substrate, or may be sandwiched between resist underlayer films.
  • the resist film thickness tends to be thin in order to prevent the pattern from collapsing. Dry etching for transferring a pattern to a film existing in the lower layer by thinning the resist cannot transfer the pattern unless the etching rate is higher than that of the upper film.
  • the substrate is coated with the resist underlayer film (containing a silicon-based compound) of the present embodiment via the organic underlayer film, and further coated with the resist film (organic resist film). Can be done.
  • the dry etching rate differs greatly depending on the selection of the etching gas between the organic component film and the inorganic component film.
  • the organic component film has an oxygen-based gas and the dry etching rate is high, and the inorganic component film contains halogen. The dry etching rate is increased by gas.
  • the underlying organic underlayer film is dry-etched with an oxygen-based gas to perform pattern transfer to the organic underlayer film, and the pattern-transferred organic underlayer film is a halogen-containing gas.
  • the lithography underlayer film (resist underlayer film) formed by using the lithography underlayer film forming composition of the present embodiment has good adhesion, the transfer pattern can be suppressed from collapsing.
  • the resist underlayer film formed by the composition for forming an underlayer film for lithography of the present embodiment is composed of ascorbic acid or a derivative or resin thereof according to the present embodiment, which has an excellent ability to absorb active light, and a silicon-containing compound (for example, hydrolysis).
  • a silicon-containing compound for example, hydrolysis.
  • the resist underlayer film based on the composition for forming the underlayer film for lithography of the present embodiment has high heat resistance, it can be used even under high temperature baking conditions. Furthermore, since it has a relatively low molecular weight and low viscosity, it is easy to uniformly fill every corner of a substrate having a step (particularly, a fine space, a hole pattern, etc.), and as a result. , Flatness and embedding properties tend to be relatively favorably enhanced.
  • the composition for forming an underlayer film for lithography may further contain a solvent, an acid, an acid cross-linking agent, etc. in addition to ascorbic acid or a derivative or resin thereof according to the present embodiment and a silicon-containing compound. Further, as an optional component, an organic polymer compound, an acid generator and a surfactant, water, an alcohol, a curing catalyst and the like can be included. From the viewpoint of coatability and quality stability, the content of ascorbic acid or a derivative or resin thereof according to the present embodiment in the composition for forming an underlayer film for lithography is preferably 0.1 to 70% by mass. It is more preferably 0.5 to 50% by mass, and particularly preferably 3.0 to 40% by mass.
  • a known solvent can be appropriately used as long as the ascorbic acid or its derivative or resin according to the present embodiment is at least soluble.
  • a solvent that can be contained in the composition for forming an underlayer film for lithography disclosed in International Publication No. 2017/188450 can be mentioned.
  • the content of the solvent is not particularly limited, but is 100 to 10,000 parts by mass with respect to 100 parts by mass of the total solid content of the composition for forming a lower layer film for lithography from the viewpoint of solubility and film formation. It is preferably 200 to 8,000 parts by mass, more preferably 200 to 5,000 parts by mass.
  • the composition for forming an underlayer film for lithography may contain an acid from the viewpoint of promoting curability.
  • the acid include hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, methanesulfonic acid, benzenesulfonic acid, toluenesulfon and the like.
  • the acid content is not particularly limited, but from the viewpoint of solubility and shape stability of the coating film, 0.001 to 20 mass by mass with respect to 100 parts by mass of the total solid content of the composition for forming an underlayer film for lithography.
  • the amount is preferably 0.005 to 10 parts by mass, and further preferably 0.01 to 5 parts by mass.
  • the composition for forming an underlayer film for lithography may contain one or more acid cross-linking agents when used as a negative resist material or as an additive for increasing the strength of a pattern even in a positive resist material.
  • the acid cross-linking agent is a compound capable of intramolecularly or intermolecularly cross-linking ascorbic acid or a derivative thereof or a resin according to the present embodiment in the presence of the above-mentioned acid.
  • Such an acid cross-linking agent is not particularly limited, but for example, a compound having one or more groups (hereinafter, referred to as "cross-linking group") capable of cross-linking ascorbic acid or a derivative thereof or a resin according to the present embodiment.
  • an acid cross-linking agent that can be contained in the composition for forming an underlayer film for lithography disclosed in International Publication No. 2017/188450 can be mentioned. Further, for example, the one described in International Publication WO2013 / 024779 can be mentioned as a specific example of the acid cross-linking agent.
  • the content of the acid cross-linking agent is not particularly limited, but is 0.01 to 100 parts by mass with respect to 100 parts by mass of the total solid content of the composition for forming an underlayer film for lithography from the viewpoint of solubility and shape stability of the coating film. It is preferably 30 parts by mass, more preferably 0.05 to 20 parts by mass, and even more preferably 0.1 to 10 parts by mass.
  • the composition for forming an underlayer film for lithography contains a silicon-containing compound together with ascorbic acid or a derivative thereof or a resin according to the present embodiment.
  • the silicon-containing compound may be either an organosilicon-containing compound or an inorganic silicon-containing compound, but is preferably an organosilicon-containing compound.
  • the inorganic silicon-containing compound include a polysilazane compound composed of a silicon oxide, a silicon nitride, and a silicon oxide nitride that can be formed by a coating method at a low temperature.
  • organosilicon-containing compound examples include polysilsesquioxane-based compounds, hydrolyzable organosilanes, hydrolysates thereof, and hydrolyzed condensates thereof.
  • the specific material based on polysilsesquioxane is not limited to the following, and for example, those described in JP-A-2007-226170 and JP-A-2007-226204 can be used.
  • the hydrolyzable organosilane, its hydrolyzate, or its hydrolyzate condensate is at least one selected from the group consisting of the hydrolyzable organosilane of the following formula (D1) and the following formula (D2).
  • Hydrolyzable organosilanes, their hydrolysates, or their hydrolyzed condensates are simply at least one organic silicon compound selected from the group consisting of formulas (D1) and (D2). May be referred to).
  • the composition for forming an underlayer film for lithography contains at least one organosilicon compound selected from the group consisting of the formulas (D1) and (D2), the Si—O bond is controlled by adjusting the curing conditions. It is easy to use, it is advantageous in terms of cost, and it is suitable for introducing an organic component.
  • the composition for forming the underlayer film for lithography is formed by using the composition for forming the underlayer film for lithography containing at least one organosilicon compound selected from the group consisting of the formula (D1) and the formula (D2).
  • the formed layer is useful as an intermediate layer of the resist layer (a layer between the upper resist layer and the organic lower layer film provided on the substrate).
  • R 3 is an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide group, an alkenyl group, an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group,
  • R 4 represents an alkoxy group, an acyloxy group or a halogen group, and a represents an integer of 0 to 3).
  • Equation (D2) [(R 5 ) c Si (R 6 ) 4-c ] 2 Y b
  • R 5 represents an alkyl group
  • R 6 represents an alkoxy group, an acyloxy group or a halogen group
  • Y represents an alkylene group or an arylene group
  • b represents an integer of 0 or 1
  • c Represents an integer of 0 or 1.
  • composition for forming an underlayer film for lithography at least one selected from the group consisting of ascorbic acid or a derivative or resin thereof according to the present embodiment and a silicon-containing compound (for example, formula (D1) and formula (D2)).
  • a silicon-containing compound for example, formula (D1) and formula (D2)
  • (Organosilicon compound) can be used in a molar ratio of 1: 2 to 1: 200. In order to obtain a good resist shape, for example, it can be used in the range of 1: 2 to 1: 100 in the molar ratio.
  • At least one organosilicon compound selected from the group consisting of the formula (D1) and the formula (D2) is preferably used as a hydrolyzed condensate (polymer of polyorganosiloxane).
  • R 3 in the hydrolyzable organosilane represented by the formula (D1) is an alkyl group, an aryl group, an aralkyl group, an alkyl halide group, an aryl halide group, an aralkyl halide group, an alkenyl group, an epoxy group or an acryloyl.
  • An "organic group” having a group, a methacryloyl group, a mercapto group, an alkoxyaryl group, an acyloxyaryl group, an isocyanurate group, a hydroxy group, a cyclic amino group, or a cyano group, or a combination thereof, and a Si—C bond.
  • R 4 represents an alkoxy group, an acyloxy group, or a halogen group, and a represents an integer of 0 to 3.
  • R 5 represents an alkyl group
  • R 6 represents an alkoxy group, an acyloxy group, or a halogen group
  • Y represents an alkylene group or an arylene group
  • b represents 0 or 1. It represents an integer
  • c represents an integer of 0 or 1.
  • hydrolyzable organosilanes represented by the formulas (D1) and (D2) include hydrolyzable organosilanes that can be contained in the composition for forming an underlayer film for lithography disclosed in International Publication No. 2017/188450. Silane can be mentioned.
  • a film may be formed as a mixture without reacting the ascorbic acid or a derivative or resin thereof according to the present embodiment with hydrolyzable organosilane or the like, but a lower layer film for lithography is formed.
  • Examples of the acid catalyst used at this time include hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, methanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid and the like.
  • the amount of the catalyst, the monomer is preferably 10 -6 to 10 moles relative to 1 mole, more preferably 10 - It is 5 to 5 mol, more preferably 10 -4 to 1 mol.
  • the amount of water when hydrolyzing and condensing these monomers is per mol of hydrolyzable substituents bonded to the monomer (ascorbic acid or its derivative or resin according to the present embodiment, hydrolyzable organosilane, etc.). It is preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, and even more preferably 0.1 to 30 mol. If the addition is 100 mol or less, the apparatus used for the reaction does not become excessive, which is economical.
  • a monomer is added to an aqueous catalyst solution to start a hydrolysis condensation reaction.
  • an organic solvent may be added to the aqueous catalyst solution, the monomer may be diluted with the organic solvent, or both may be performed.
  • the reaction temperature is preferably 0 to 100 ° C, more preferably 40 to 100 ° C.
  • a method in which the temperature is maintained at 5 to 80 ° C. when the monomer is added dropwise and then aged at 40 to 100 ° C. is preferable.
  • the resist underlayer film of the present embodiment can also be used as an antireflection film for a normal single-layer resist or a base material for suppressing pattern collapse. Since the resist underlayer film of the present embodiment has excellent etching resistance for base processing, it can be expected to function as a hard mask for base processing.
  • the thickness of the substrate to be processed or the film to be processed is not particularly limited, but is usually preferably about 50 nm to 10,000 nm, and more preferably 75 nm to 5,000 nm.
  • the refractive index of the optical article is preferably 1.65 or more, more preferably 1.70 or more, and further preferably 1.75 or more, from the viewpoint of miniaturization of the optical component and improvement of the light collection rate.
  • the transparency of the optical article is preferably 70% or more, more preferably 80% or more, still more preferably 90% or more.
  • the content of at least one compound selected from the acid cross-linking agent (G1), the acid cross-linking agent (G2), and the acid cross-linking agent (G3) in the acid cross-linking agent (G) is not particularly limited.
  • the range can be various depending on the type of the substrate used when forming the composition for forming an optical component.
  • the composition for forming an optical component of the present embodiment contains a dissolution accelerator, a dissolution control agent, a sensitizer, and a surfactant as other components (F), if necessary, as long as the object of the present embodiment is not impaired.
  • One or two or more kinds of additives such as an activator and an organic carboxylic acid or an oxo acid of phosphorus or a derivative thereof can be added.
  • the other component (F) can be, for example, the same as the other component (F) that can be contained in the composition for forming a lower layer film for lithography of the present embodiment described above.
  • Example 1-2 The reaction was carried out in the same manner as in Example 1-1 except that the reaction was carried out at 80 ° C., and the desired compound was obtained in a yield of 71%.
  • Example 1-3 The same procedure as in Example 1-1 was carried out except that NMP (N-methylpyrrolidone) was used instead of DMSO as the solvent, and the desired compound was obtained in a yield of 29%.
  • NMP N-methylpyrrolidone
  • Example 2-1 The compound according to this embodiment was synthesized based on the reaction formula represented by the following formula (2-2).
  • Example 4 The compound according to this embodiment was synthesized based on the reaction formula represented by the following formula (2-4).
  • Example 5-1 The resin according to this embodiment was synthesized based on the reaction formula represented by the following formula (2-5).
  • L-ascorbic acid (3 mmol: 0.528 g) was placed in a 50 ml eggplant flask, nitrogen substitution was performed, and triethylamine (7 mmol: 1.0 ml) and NMP 15 ml were added.
  • terephthaloyl chloride (3 mmol: 0.61 g) dissolved in 5 ml of NMP in an ice bath was added dropwise, and the mixture was reacted at room temperature for 24 hours. After completion of the reaction, the mixture was redisposited in a 1 mol / L hydrochloric acid aqueous solution and filtered through Kiriyama to obtain a brown solid. This was dissolved in methanol, reprecipitated in ether, filtered through membranes, and dried under reduced pressure. The desired resin, which is a white solid, was obtained.
  • Example 6-1 The resin according to this embodiment was synthesized based on the reaction formula represented by the following formula (2-7).
  • Example 6-2 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (10 mmol: 1.780 g), hexamethylene diisocyanate (10 mmol: 1.675 g), NMP 15 ml, and TEA 5.6 ml were added, and the mixture was added under nitrogen at room temperature. The mixture was stirred for 24 hours and reacted. After completion of the reaction, reprecipitation was carried out with diethyl ether, and a pink viscous solid was precipitated.
  • Example 6-3 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (5 mmol: 0.8879 g), hexamethylene diisocyanate (10 mmol: 1.7233 g), THF 15 ml, and TEA 2.8 ml were added, and the mixture was added under nitrogen at room temperature. The mixture was stirred for 24 hours and reacted. After completion of the reaction, the reaction solution was concentrated with an evaporator and reprecipitated with water. As a result, a white solid was precipitated.
  • the mixture was dried under reduced pressure at 60 ° C. to obtain the desired resin in a yield of 19%.
  • Example 6-4 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (10 mmol: 1.7681 g), hexamethylene diisocyanate (10 mmol: 1.7338 g), THF 15 ml, and TEA 5.6 ml were added, and the temperature was changed to room temperature under nitrogen. Was stirred for 24 hours and reacted. After completion of the reaction, the reaction solution was concentrated with an evaporator, and half was reprecipitated with diethyl ether and the other half was reprecipitated with hexane.
  • Example 6-5 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (10 mmol: 1.7612 g), hexamethylene diisocyanate (15 mol: 2.5218 g), THF 15 ml, and TEA 5.6 ml were added, and the mixture was added under nitrogen at room temperature. The reaction was carried out for 24 hours. After completion of the reaction, the reaction solution was concentrated with an evaporator and reprecipitated with diethyl ether. As a result, a pink viscous solid was precipitated.
  • Example 6-6 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (10 mmol: 1.7612 g), hexamethylene diisocyanate (15 mmol: 2.5218 g), THF 15 ml, and TEA 5.6 ml were added, and the mixture was added under nitrogen at room temperature. The reaction was carried out for 48 hours. After completion of the reaction, the reaction solution was concentrated with an evaporator and reprecipitated with diethyl ether. As a result, a pink viscous solid was precipitated.
  • Example 6-7 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (5 mmol: 0.8806 g), hexamethylene diisocyanate (10 mmol: 1.682 g), THF 15 ml, and TEA 2.8 ml were added, and the mixture was added under nitrogen at room temperature. The reaction was carried out for 24 hours. After completion of the reaction, the reaction solution was concentrated with an evaporator and reprecipitated with diethyl ether. As a result, a pink viscous solid was precipitated.
  • Example 6-8 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, L-ascorbic acid (5 mmol: 0.8806 g), hexamethylene diisocyanate (10 mmol: 1.682), THF 15 ml, and TEA 2.8 ml were added, and the mixture was added under nitrogen at room temperature. The reaction was carried out for 48 hours. After completion of the reaction, the reaction solution was concentrated with an evaporator and reprecipitated with diethyl ether. As a result, a pink viscous solid was precipitated.
  • the resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, and L-ascorbic acid (10 mmol: 1.7612 g), hexamethylene diisocyanate (15 mmol: 2.5218 g), THF 15 ml, and dibutyltin dilaurate (4 mmol: 2.5262 g) were added. In addition, the reaction was carried out under nitrogen at room temperature for 2 hours. After completion of the reaction, Kiriyama filtration was performed to obtain a white gel. Then, it was dried under reduced pressure, and the target resin was obtained in a yield of 99% or more. The structure of the resin was confirmed by IR measurement.
  • Example 6-11 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, and L-ascorbic acid (10 mmol: 1.7612 g), hexamethylene diisocyanate (10 mmol: 1.6812 g), THF 15 ml, and dibutyltin dilaurate (4 mmol: 2.5262 g) were added. In addition, the reaction was carried out under nitrogen at room temperature for 2 hours. After completion of the reaction, Kiriyama filtration was performed to obtain a white gel. Then, it dried under reduced pressure, and the target resin was obtained in a yield of 85%. The structure of the resin was confirmed by IR measurement.
  • Example 6-12 The resin according to this embodiment was synthesized based on the reaction formula represented by the above formula (2-7). Specifically, a stirrer was placed in a 100 ml eggplant flask, and L-ascorbic acid (5 mmol: 0.8806 g), hexamethylene diisocyanate (10 mmol: 1.6812 g), THF 15 ml, and dibutyltin dilaurate (2 mmol: 1.263 g) were added. In addition, the reaction was carried out under nitrogen at room temperature for 4 hours. After completion of the reaction, Kiriyama filtration was performed to obtain a white gel. Then, it was dried under reduced pressure, and the target resin was obtained in a yield of 99% or more. The structure of the resin was confirmed by IR measurement.
  • the molecular weight of the obtained dimethylnaphthalene formaldehyde resin was number average molecular weight (Mn): 562, weight average molecular weight (Mw): 1168, and dispersity (Mw / Mn): 2.08.
  • a four-necked flask with an internal volume of 0.5 L equipped with a Dimroth condenser, a thermometer and a stirring blade was prepared.
  • 100 g (0.51 mol) of the dimethylnaphthalene formaldehyde resin obtained as described above and 0.05 g of p-toluenesulfonic acid were charged under a nitrogen stream, and the temperature was raised to 190 ° C. After heating for 2 hours, the mixture was stirred. After that, 52.0 g (0.36 mol) of 1-naphthol was further added, the temperature was further raised to 220 ° C., and the reaction was carried out for 2 hours.
  • the obtained resin (C-1) was Mn: 885, Mw: 2220, and Mw / Mn: 2.51.
  • Tetrahydrofuran contains 4.15 g of 2-methyl-2-methacryloyloxyadamantane, 3.00 g of methacrylloyloxy- ⁇ -butyrolactone, 2.08 g of 3-hydroxy-1-adamantyl methacrylate, and 0.38 g of azobisisobutyronitrile. It was dissolved in 80 mL to prepare a reaction solution. The reaction solution was polymerized under a nitrogen atmosphere at a reaction temperature of 63 ° C. for 22 hours, and then the reaction solution was added dropwise to 400 mL of n-hexane. The obtained produced resin was coagulated and purified, and the produced white powder was filtered and then dried under reduced pressure at 40 ° C. overnight to obtain a resin (AC-1) represented by the following formula.
  • Examples 7-1 to 7-9, Comparative Example 2 As the compound or resin, it was obtained in Example 1-1, Example 2-1 and Example 3, Example 4, Example 5-1 and Example 6-1 and Example 6-4, and Comparative Example 1.
  • the compositions for forming a resist film having the compositions shown in Table 1 below were prepared by using the above compounds or resins. The following were used as the acid generator, the acid diffusion control agent, and the organic solvent.
  • Acid generator Triphenylsulfonium nonafluoromethanesulfonate manufactured by Midori Kagaku Co., Ltd. (referred to as "TPS-109" in the table)
  • Acid diffusion control agent Tri-n-octylamine manufactured by Kanto Chemical Co., Inc.
  • Crosslinking agent Nikalac MW-100LM manufactured by Sanwa Chemical (indicated as “MW-100LM” in the table)
  • Organic solvent Kanto Chemical Co., Ltd., propylene glycol monomethyl ether (indicated as "PGME” in the table)
  • Solubility of compound or resin in safe solvent The solubility of the compound or resin used in Examples 7-1 to 7-9 and Comparative Example 2 in a safe solvent is based on the following criteria based on the amount dissolved in PGME. Evaluated in. The amount of dissolution was measured at 23 ° C. The compound or resin is weighed alone in a test tube, PGME is added so that the concentration of the compound or resin becomes a predetermined concentration, ultrasonic waves are applied for 30 minutes with an ultrasonic cleaner, and the state of the liquid thereafter is visually observed. The amount of dissolution was measured by observing at. The results are shown in Table 2. A: 5.0% by mass ⁇ dissolution amount B: 2.0% by mass ⁇ dissolution amount ⁇ 5.0% by mass C: Soluble amount ⁇ 2.0% by mass
  • the shape of the obtained resist pattern of 50 nm L / S (1: 1) was observed using an electron microscope (S-4800) manufactured by Hitachi, Ltd. Regarding the resist pattern shape after development, a resist pattern having no pattern collapse and having a better rectangular property than Comparative Example 2 was evaluated as "A”, and a resist pattern having the same or inferiority as Comparative Example 2 was evaluated as "C”. The results are shown in Table 2.
  • Examples 8-1 to 8-8, Comparative Example 3 Compositions for forming a resist underlayer film having the compositions shown in Table 3 were prepared. The following were used as the acid generator, the cross-linking agent and the organic solvent.
  • Acid generator Ditert-butyldiphenyliodonium nonafluoromethanesulfonate (manufactured by Midori Chemical Co., Ltd.) (referred to as "DTDPI” in the table)
  • Cross-linking agent "Nikalac MX270” (product name, manufactured by Sanwa Chemical Co., Ltd.) (indicated as “MX270” in the table)
  • Organic solvent Propylene glycol monomethyl ether acetate (indicated as "PGMEA” in the table)
  • the resist underlayer film forming composition prepared above is applied onto a SiO 2 substrate having a film thickness of 300 nm, and baked at 240 ° C. for 60 seconds and then at 400 ° C. for 120 seconds to obtain a resist underlayer having a film thickness of 70 nm. A film was formed. A resist solution for ArF was applied onto the resist underlayer film and baked at 130 ° C. for 60 seconds to form a photoresist film having a film thickness of 140 nm.
  • the ArF resist solution contains 5 parts by mass of the resin (AC-1) of Synthesis Example 1, 1 part by mass of triphenylsulfonium nonafluoromethanesulfonate, 2 parts by mass of tributylamine, and 92 parts by mass of PGMEA. Was used.
  • the photoresist film was exposed using an electron beam drawing apparatus "ELS-7500” (product name, manufactured by Elionix Inc., 50 keV), and baked (PEB) at 115 ° C. for 90 seconds to 2.38 mass%.
  • ELS-7500 product name, manufactured by Elionix Inc., 50 keV
  • PEB baked
  • a positive resist pattern was obtained by developing with an aqueous solution of tetramethylammonium hydroxide (TMAH) for 60 seconds.
  • TMAH tetramethylammonium hydroxide
  • Table 4 shows the results of observing the defects of the obtained resist patterns of 55 nm L / S (1: 1) and 80 nm L / S (1: 1).
  • "good” shown as a result of "resist pattern after development” means that no pattern collapse was observed in the formed resist pattern
  • “poor” means the formed resist pattern. Indicates that the pattern collapsed.
  • the minimum line width having no pattern collapse and good rectangularity was used as an evaluation index as "resolution”.
  • the minimum amount of electron beam energy that can draw a good pattern shape was defined as "sensitivity” and used as an evaluation index.
  • Examples 9-1 to 9-8 The resist underlayer film forming composition of Examples 8-1 to 8-8 was applied onto a SiO 2 substrate having a film thickness of 300 nm, and baked at 240 ° C. for 60 seconds and then at 400 ° C. for 120 seconds to obtain a film thickness. An 80 nm resist underlayer film was formed. A silicon-containing intermediate layer film material was applied onto the resist underlayer film and baked at 200 ° C. for 60 seconds to form a silicon-containing intermediate layer film having a film thickness of 35 nm. Further, the above resist solution for ArF was applied onto the silicon-containing intermediate layer film and baked at 130 ° C. for 60 seconds to form a photoresist film having a film thickness of 150 nm.
  • the silicon-containing intermediate layer film material As the silicon-containing intermediate layer film material, the silicon atom-containing polymer described in ⁇ Synthesis Example 1> of JP-A-2007-226170 was used. Next, the photoresist film was mask-exposed using an electron beam drawing apparatus (ELS-7500, 50 keV), baked (PEB) at 115 ° C. for 90 seconds, and 2.38 mass% tetramethylammonium hydroxide was used. By developing with an aqueous solution (hereinafter, also referred to as “TMAH”) for 60 seconds, a positive resist pattern of 55 nm L / S (1: 1) was obtained.
  • ELS-7500 electron beam drawing apparatus
  • PEB baked
  • 2.38 mass% tetramethylammonium hydroxide was used.
  • TMAH aqueous solution
  • the silicon-containing intermediate layer film is dry-etched using the obtained resist pattern as a mask.
  • the dry etching process of the resist underlayer film using the silicon-containing intermediate layer film pattern as a mask and the dry etching process of the SiO 2 film using the obtained resist underlayer film pattern as a mask were sequentially performed.
  • Each etching condition is as shown below.
  • the pattern cross section obtained as described above (that is, the shape of the SiO 2 film after etching) was observed using an electron microscope "S-4800" (product name, manufactured by Hitachi, Ltd.) to form a resist pattern. Gender was evaluated. The results are shown in Table 5.
  • "good” shown as “resist pattern formability” means that no large defect was found in the formed pattern cross section, and "defective” means that a large defect was not found in the formed pattern cross section. Indicates that it was seen.
  • Example 10-1 to 10-8 Comparative Example 4
  • the resist underlayer film forming compositions of Examples 8-1 to 8-8 are placed on a SiO 2 stepped substrate having a step of width 1000 nm, pitch 2000 nm, and depth 200 nm. Each was applied.
  • Comparative Example 4 in the resist underlayer film forming composition of Example 8-1, the resin (C-1) obtained in Comparative Example 1 was used instead of the compound obtained in Example 1-1.
  • a composition for forming a resist underlayer film was prepared, and the composition was applied onto a SiO 2 stepped substrate in the same manner as in Examples 10-1 to 10-8. Then, it was calcined at 240 ° C.
  • Examples 11-1 to 11-7, Comparative Example 5 Each compound or resin shown in Table 7 was dissolved in PGMEA as a solvent to prepare a solution having a solid content concentration of 10% by mass.
  • the prepared solution was formed on a 12-inch silicon wafer using a spin coater LithiusPro (manufactured by Tokyo Electron Limited) while adjusting the rotation speed so as to have a film thickness of 200 nm. Then, it was baked at 250 ° C. for 1 minute to prepare a substrate on which the films were laminated. The prepared substrate was baked at 350 ° C. for 1 minute using a hot plate capable of further high temperature treatment to obtain a cured resin film.
  • the composition containing the compound or resin of the present embodiment can form a resin film having a high n value and a low k value at a wavelength of 193 nm used in ArF exposure. ..
  • Example 12-1 to 12-8 Comparative Example 6
  • the resist underlayer film forming composition prepared in Examples 8-1 to 8-8 was used as the optical member forming composition.
  • the resin (C-1) obtained in Comparative Example 1 was used instead of the compound obtained in Example 1-1.
  • a composition for forming a resist underlayer film was applied onto a SiO 2 substrate having a film thickness of 300 nm and baked at 260 ° C. for 300 seconds to form a film for an optical member having a film thickness of 100 nm.
  • compositions for forming optical articles of Examples 12-1 to 12-8 not only had a high refractive index but also a low extinction coefficient and excellent transparency. On the other hand, it was found that the composition of Comparative Example 6 was inferior in performance as an optical component.
  • the composition according to the present embodiment is excellent in solubility in an organic solvent, sensitivity, flatness, and resist pattern forming property, and is useful as a composition for forming a lithography film. It also has excellent transparency at wavelengths of 193 nm and 633 nm, and is useful as a composition for forming a lithography film or forming an optical component, which requires transparency.
  • the present invention includes the following embodiments.
  • the dissociable group has a property of being dissociated by an acid, a substituted methyl group, a 1-substituted ethyl group, a 1-substituted-n-propyl group, a 1-branched alkyl group, a silyl group, an acyl group, 1-.
  • a compound according to the present embodiment which is a substituted alkoxymethyl group, a cyclic ether group, an alkoxycarbonyl group, or an alkoxycarbonylalkyl group.
  • crosslinkable group is an allyl group, a (meth) acryloyl group, a vinyl group, an epoxy group, an alkoxymethyl group, or a cyano group.
  • R 3 in the formulas (Z-1) to (Z-3) is a hexamethylene group or a phenylene group.
  • R 0 is synonymous with the formula (X-2), and R 4 is synonymous with the formula (a-1).
  • R 0 is a hydrogen atom, a dissociative group or a crosslinkable group, respectively, and at least one R 0 is a hydrogen atom.
  • R 5 is a divalent group of a substituted or unsubstituted carbon atoms 1 ⁇ 22 .
  • X is a halogen atom, Me is a methyl group.
  • R 0 is synonymous with the formula (X-2), and R 5 is synonymous with the formula (a-2).
  • R 0 is a hydrogen atom, a dissociative group or a crosslinkable group, respectively, and at least one R 0 is a hydrogen atom.
  • Equation (a-3) X-R 6- X
  • R 6 is a substituted or unsubstituted divalent group having 1 to 22 carbon atoms, and may contain a ketone group or an ester bond.
  • X is a halogen atom.
  • R 0 is synonymous with the formula (X-2), and R 6 is synonymous with the formula (a-3).
  • R 0 is a hydrogen atom, a dissociative group or a crosslinkable group, respectively, and at least one R 0 is a hydrogen atom.
  • R 7 is a substituted or unsubstituted divalent group having 1 to 20 carbon atoms.
  • X is a halogen atom.
  • R 0 is synonymous with the formula (X-2), and R 7 is synonymous with the formula (a-4).
  • the dissociable group has a property of being dissociated by an acid, a substituted methyl group, a 1-substituted ethyl group, a 1-substituted-n-propyl group, a 1-branched alkyl group, a silyl group, an acyl group, 1-.
  • a resin according to the present embodiment which is a substituted alkoxymethyl group, a cyclic ether group, an alkoxycarbonyl group, or an alkoxycarbonylalkyl group.
  • crosslinkable group is an allyl group, a (meth) acryloyl group, a vinyl group, an epoxy group, an alkoxymethyl group, or a cyano group.

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  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'invention concerne un composé qui présente une sensibilité élevée et est hautement soluble dans un solvant. Le composé est représenté par la formule générale (X-1). [Formule chimique 1] (Dans la formule (X-1), chaque R0 désigne indépendamment un atome d'hydrogène, un groupe dissociable ou un groupe réticulable, et au moins l'un des R0 est un groupe dissociable ou un groupe réticulable.)
PCT/JP2020/033865 2019-09-10 2020-09-08 Composé, résine, composition, film de réserve, procédé de formation de motif, film de sous-couche et article optique WO2021049472A1 (fr)

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