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  • H10P76/20—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials
  • H10P76/204—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials of organic photoresist masks
  • H10P76/2041—Photolithographic processes
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
  • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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  • G03F7/004—Photosensitive materials
  • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
  • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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  • G03F7/004—Photosensitive materials
  • G03F7/075—Silicon-containing compounds
  • G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/094—Multilayer resist systems, e.g. planarising layers
• • G—PHYSICS
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  • 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
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  • 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
• • G—PHYSICS
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  • 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
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/40—Treatment after imagewise removal, e.g. baking
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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  • 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
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/42—Stripping or agents therefor
  • G03F7/422—Stripping or agents therefor using liquids only
• • 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
  • G03F7/70—Microphotolithographic exposure; Apparatus therefor
  • G03F7/70008—Production of exposure light, i.e. light sources
  • G03F7/70033—Production of exposure light, i.e. light sources by plasma extreme ultraviolet [EUV] sources
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
  • H10P76/00—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
• • 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
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
• • C—CHEMISTRY; METALLURGY
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  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
  • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing 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
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
  • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing 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
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups

Definitions

• R 2 represents an optionally substituted alkyl group, an optionally substituted halogenated alkyl group, an optionally substituted alkoxyalkyl group, an optionally substituted alkenyl group, or an epoxy group; an organic group having an acryloyl group, an organic group having a methacryloyl group, an organic group having a mercapto group, an organic group having an amino group, an organic group having an alkoxy group, an organic group having a sulfonyl group, or a cyano group or a combination of two or more thereof.
• X represents an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom.
• a represents an integer of 1 to 3.
• b represents an integer of 0 to 2; a+b represents an integer of 1-3.
• R 1 represents an organic group having an unsaturated bond and a ring structure.
• R 2 represents an optionally substituted alkyl group, an optionally substituted halogenated alkyl group, an optionally substituted alkoxyalkyl group, an optionally substituted alkenyl group, or an epoxy group; an organic group having an acryloyl group, an organic group having a methacryloyl group, an organic group having a mercapto group, an organic group having an amino group, an organic group having an alkoxy group, an organic group having a sulfonyl group, or a cyano group or a combination of two or more thereof.
• R 1 , R 2 and X represents an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom.
• R 1 , R 2 and X may be plural, the plural R 1 , R 2 and X may be the same or different.
• R 2 is not an organic group having an unsaturated bond and a ring structure.
• a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned as a halogen atom.
• R 1 in formula (A-1) is preferably represented by formula (A-2a) below.
• the monovalent group for R a includes, for example, a halogen atom and a monovalent organic group having 1 to 10 carbon atoms.
• the monovalent group for R a may or may not have an unsaturated bond.
• the monovalent group for R a may or may not have a ring structure.
• the amino group (-N(R 32 )-) in the formula (A-2-2) may be cationized.
• the amino group (—N(R 32 )—) in formula (A-2-2) is cationized to form a nitrate. You may have
• the alkylene group having 1 to 6 carbon atoms in R 21 , R 31 , R 33 , R 41 , R 42 and R 51 may be linear or branched.
• Examples of the alkylene group having 1 to 6 carbon atoms include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene and hexamethylene. Among these, a methylene group, an ethylene group, a trimethylene group, and a tetramethylene group are preferred.
• alkyl group specific examples of linear or branched alkyl groups include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n -pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-dimethyl-n-butyl group, 1,3-
• n-pentyloxy group 1-methyl-n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl- n-propoxy group, 2,2-dimethyl-n-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3- methyl-n-pentyloxy group, 4-methyl-n-pentyloxy group, 1,1-dimethyl-n-butoxy group, 1,2-dimethyl-n-butoxy group, 1,3-dimethyl-n-butoxy group, 2 , 2-dimethyl-n-butoxy group, 2,3-dimethyl-n-butoxy group, 3,3-dimethyl-n-butoxy group, 1-ethyl-n-butoxy group, 2-ethyl-n-butoxy group, 1,1,2-trimethyl
• R 101 and R 102 each independently represent a hydrogen atom or a hydrocarbon group
• L each independently represents an optionally substituted alkylene group. * represents a bond.
• Hydrocarbon groups include, but are not limited to, alkyl groups, alkenyl groups, and the like. Specific examples of these alkyl groups and alkenyl groups are the same as those described above for R 2 .
• the alkylene group may be linear or branched, and usually has 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.
• R 3 is a group that bonds to a silicon atom and is independently of each other an optionally substituted alkyl group, an optionally substituted halogenated alkyl group, an optionally substituted represents a good alkoxyalkyl group or an optionally substituted alkenyl group, or an organic group having an epoxy group, an organic group having an acryloyl group, an organic group having a methacryloyl group, an organic group having a mercapto group, or an amino group. an organic group having an alkoxy group, an organic group having a sulfonyl group, an organic group having a cyano group, or a combination of two or more thereof.
• silane compound having an onium group in the molecule hydrolyzable organosilane
• a silane compound having an onium group in its molecule is expected to effectively and efficiently promote the cross-linking reaction of hydrolyzable silane.
• the silicon-bonded group R 11 in formula (3) can be a heteroaliphatic cyclic ammonium group represented by formula (S2) below.
• the reaction between the silanol group of the hydrolytic condensate and the hydroxy group of the alcohol is carried out by contacting the hydrolytic condensate with the alcohol at a temperature of 40 to 160° C., for example, 60° C., for 0.1 to 48 hours, for example. By reacting for 24 hours, a modified product with capped silanol groups is obtained.
• the alcohol of the capping agent can be used as a solvent in the composition containing polysiloxane.
• a hydrolytic condensate of hydrolyzable silane is obtained by hydrolyzing and condensing the aforementioned silane compound (hydrolyzable silane).
• the aforementioned silane compounds (hydrolyzable silanes) contain an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom directly bonded to a silicon atom, i.e., an alkoxysilyl group, an aralkyloxysilyl group, an acyloxysilyl group, or a halogen atom.
• silyl groups hereinafter referred to as hydrolyzable groups).
• the obtained polysiloxane varnish may be subjected to solvent replacement or may be diluted with a solvent as appropriate.
• the resulting polysiloxane varnish may have a film-forming component concentration of 100% by distilling off the organic solvent if the storage stability is not poor.
• the film-forming component refers to a component excluding the solvent component from all components of the composition.
• the organic solvent used for solvent replacement, dilution, etc. of the polysiloxane varnish may be the same as or different from the organic solvent used for the hydrolysis and condensation reaction of the hydrolyzable silane.
• the diluting solvent is not particularly limited, and one or two or more can be arbitrarily selected and used.
• the compound of formula (D-2) is a quaternary ammonium salt represented by R 22 R 23 R 24 R 25 N + Y - .
• R 22 , R 23 , R 24 and R 25 of this quaternary ammonium salt are, for example, an alkyl group having 1 to 18 carbon atoms such as ethyl, propyl, butyl, cyclohexyl, cyclohexylmethyl, phenyl or an aryl group having 6 to 18 carbon atoms such as a group, or an aralkyl group having 7 to 18 carbon atoms such as a benzyl group.
• This compound is also commercially available, and for example, by reacting a substituted pyridine such as picoline with an alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
• an alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
• alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
• the compound of formula (D-6) is a tertiary ammonium salt derived from an amine, where m a represents an integer of 2-11 and n a represents 2 or 3.
• the anion (Y ⁇ ) includes halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ) and other acid groups.
• This compound can be produced by reacting an amine with a weak acid such as a carboxylic acid or phenol.
• Carboxylic acids include formic acid and acetic acid.
• Phosphonium triphenylmethylphosphonium halide, triphenylmonoalkylphosphonium halide such as triphenylethylphosphonium halide, triphenylbenzylphosphonium halide, tetraphenylphosphonium halide, tritolylmonoarylphosphonium halide, or tritolylmonohalide
• Alkylphosphonium (wherein the halogen atom is a chlorine atom or a bromine atom) can be mentioned.
• maleimide compounds include, but are not limited to, maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and N-hydroxyethylmaleimide.
• the weight-average molecular weight of the organic polymer can generally range from 1,000 to 1,000,000.
• the weight average molecular weight is, for example, 3,000 to 300,000, or 5,000 to 5,000. It can be 300,000, or 10,000-200,000, and so on.
• Such organic polymers may be used singly or in combination of two or more.
• onium salt compounds include diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-normal butanesulfonate, diphenyliodonium perfluoro-normal octane sulfonate, diphenyliodonium camphorsulfonate, bis(4-t-butylphenyl ) iodonium salt compounds such as iodonium camphorsulfonate, bis(4-t-butylphenyl)iodonium trifluoromethanesulfonate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoron-butanesulfonate, triphenylsulfonium camphorsulfonate, triphenylsulfonium Examples include, but are not limited to,
• a silicon-containing resist underlayer film-forming composition filtered through a nylon filter can be used as the silicon-containing resist underlayer film-forming composition used for forming the resist underlayer film.
• the silicone-containing resist underlayer film-forming composition filtered through a nylon filter means that the silicone-containing resist underlayer film-forming composition was filtered through a nylon filter in the middle of manufacturing the silicon-containing resist underlayer film-forming composition, or after all the components were mixed. Refers to composition.
• an organic solvent can be used as a developer, and development is performed with the developer (solvent) after exposure.
• the developer solvent
• the metal-containing resist film in the unexposed portions is removed to form a pattern of the metal-containing resist film.
• the resist underlayer film (intermediate layer) is removed, and then the patterned metal-containing resist film and the patterned resist underlayer film ( An intermediate layer) is used as a protective film to remove the organic underlayer film (lower layer). Finally, the substrate is processed using the patterned resist underlayer film (intermediate layer) and the patterned organic underlayer film (lower layer) as protective films.
• Resist patterns were formed using the compositions obtained in Examples 2 to 11 and Comparative Examples 1 to 4 in the same procedure. Using a critical dimension SEM (CG4100) manufactured by Hitachi High-Technologies Co., Ltd., the amount of exposure when a line is formed with a line dimension of 16 nm is measured and this is taken as the sensitivity, and the line width of 120 lines at this time is measured. It was measured to determine the line width roughness (LWR). Table 3 shows the results.
• Comparative Example 1 using a hydrolyzable silane having no unsaturated bond or alicyclic structure Comparative Example 2 using a hydrolyzable silane having a cyclic structure but no unsaturated bond
• the pattern width roughness (LWR) was inferior to that of Examples.

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