WO2017061561A1 - 新規ポリスルホンアミド化合物、及び該化合物を含有する樹脂組成物 - Google Patents
新規ポリスルホンアミド化合物、及び該化合物を含有する樹脂組成物 Download PDFInfo
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- WO2017061561A1 WO2017061561A1 PCT/JP2016/079836 JP2016079836W WO2017061561A1 WO 2017061561 A1 WO2017061561 A1 WO 2017061561A1 JP 2016079836 W JP2016079836 W JP 2016079836W WO 2017061561 A1 WO2017061561 A1 WO 2017061561A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/30—Polysulfonamides; Polysulfonimides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/10—Polysulfonamides; Polysulfonimides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0387—Polyamides or polyimides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
Definitions
- the present invention relates to a novel polysulfonamide compound and a resin composition using the compound.
- Patent Documents 1 and 2 describe a high heat resistant positive resist material using polyimide or polybenzoxazole.
- the precursor due to the low solubility of polyimide and polybenzoxazole in the solvent, after the patterning is performed using the precursor polyamic acid or polyhydroxyamide, the precursor is polyimide at a heat treatment temperature of 300 ° C. or higher. And converted to polybenzoxazole.
- the thinning of the wafer 100 ⁇ m or less
- the problem of thermal distortion of the wafer due to high temperature processing has become apparent. Therefore, low temperature cyclization at 200 ° C. or lower to polyimide or polybenzoxazole is required.
- Non-Patent Document 1 proposes a negative photosensitive polymer using engineering ether polyether ether sulfone (PEES).
- PEES engineering ether polyether ether sulfone
- the exposed part becomes insoluble in the organic solvent of the developer due to the crosslinking reaction, and the unexposed part is dissolved well in the organic solvent of the developer to obtain a pattern.
- development with such an organic solvent is not preferable in consideration of processing of waste liquid after development, environmental load, and the like.
- an organic solvent developer is expensive, development with an alkaline aqueous solution such as a 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution that is inexpensive and widely used in lithography patterning is preferred.
- TMAH tetramethylammonium hydroxide
- the conventional heat resistant photoresist using polyimide and polybenzoxazole required a high temperature of 300 ° C. or higher for the ring closure reaction.
- a heat-resistant photoresist using PEES polyetherethersulfone
- PEES polyetherethersulfone
- development was difficult. It is desired to provide a photoresist material that does not require a high-temperature cyclization reaction to form a cured product pattern and can be developed with an aqueous developer.
- the first object of the present invention is to provide a polysulfonamide compound itself having a novel structure.
- the second object of the present invention is to provide a resin composition containing the novel polysulfonamide compound and a cured product formed using the resin composition.
- R 1 to R 8 each independently represents a hydrogen atom or a monovalent organic group.
- X represents a divalent linking group that is not conjugated to the benzene ring to which it is bonded.
- Y represents two A polysulfonamide compound having a repeating unit represented by: [2].
- Y is the following formula (2) (In the formula (2), R 9 to R 16 each independently represents a hydrogen atom or a monovalent organic group.
- Y ′ represents a direct bond, an oxygen atom, a carbonyl group, a methylene group, a sulfur atom or a sulfonyl group.
- the polysulfonamide compound according to [1] which is a divalent aromatic residue represented by: [3].
- a resin composition comprising the polysulfonamide compound according to any one of [1] to [3] above and a component other than the polysulfonamide compound. [5].
- the resin composition according to [4] which contains an organic solvent.
- a polysulfonamide compound having a novel structure that does not exist in the prior art is provided. Moreover, since the preferable polysulfonamide compound by this invention does not require a ring-closing reaction, the pattern which has the outstanding resolution and cured film physical property can be formed by using the resin composition containing this compound. In addition, the polysulfonamide compound of the present invention is environmentally friendly because it can be developed with an aqueous developer.
- the polysulfonamide compound of the present invention has a repeating unit represented by the following formula (1).
- R 1 to R 8 each independently represents a hydrogen atom or a monovalent organic group.
- X represents a divalent linking group that is not conjugated to the benzene ring to which it is bonded.
- Y represents a divalent aromatic residue.
- the monovalent organic group represented by R 1 to R 8 in the formula (1) is not particularly limited.
- an aliphatic hydrocarbon residue, a cyano group, a halogen atom, a carboxylic acid amide group, an amino group, an alkoxy group examples thereof include an aryloxy group, an alkoxycarbonyl group, an arylcarbonyl group, and an acyl group.
- the aliphatic hydrocarbon residue which is a monovalent organic group represented by R 1 to R 8 in Formula (1) is a residue obtained by removing one hydrogen atom from an aliphatic hydrocarbon composed of a carbon atom and a hydrogen atom. is there. Examples thereof include saturated or unsaturated, linear, branched or cyclic aliphatic hydrocarbon residues.
- the number of carbon atoms of the aliphatic hydrocarbon residue is not particularly limited, and the hydrogen atom of the aliphatic hydrocarbon group is, for example, a cyano group, a halogen atom, a carboxylic acid amide group, an amino group, an alkoxy group, an aryloxy group It may be substituted with a group, an alkoxycarbonyl group, an arylcarbonyl group or an acyl group.
- halogen atom that is a monovalent organic group represented by R 1 to R 8 in Formula (1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the amino group that is a monovalent organic group represented by R 1 to R 8 in the formula (1) is not particularly limited, but is not limited to an unsubstituted amino group, a mono- or dimethylamino group, a mono- or diethylamino group, a mono- or di- ( n-propyl) amino group and other alkyl-substituted amino groups, mono- or diphenylamino groups, mono- or dinaphthylamino groups and other aromatic-substituted amino groups, monoalkylmonophenylamino groups and other alkyl groups and aromatic residues
- Examples thereof include an amino group or a benzylamino group each substituted, an acetylamino group, and a phenylacetylamino group.
- the alkoxy group that is a monovalent organic group represented by R 1 to R 8 in the formula (1) is not particularly limited, but is a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group. Group, sec-butoxy group, t-butoxy group and the like.
- the aryloxy group that is a monovalent organic group represented by R 1 to R 8 in Formula (1) is not particularly limited, and examples thereof include a phenoxy group and a naphthoxy group.
- the alkoxycarbonyl group that is a monovalent organic group represented by R 1 to R 8 in Formula (1) is not particularly limited, and examples thereof include an alkoxycarbonyl group having 1 to 10 carbon atoms. Specific examples thereof include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, t-butoxycarbonyl group, n-pentene.
- the arylcarbonyl group which is a monovalent organic group represented by R 1 to R 8 in Formula (1), is not particularly limited.
- it represents a group in which an aryl group such as benzophenone or naphthophenone and carbonyl are linked.
- the acyl group represented by R 1 to R 8 in the formula (1) is not particularly limited, and examples thereof include an alkylcarbonyl group having 1 to 10 carbon atoms and an arylcarbonyl group.
- alkylcarbonyl group having 1 to 4 carbon atoms is preferred, and specific examples include an acetyl group, a propionyl group, a trifluoromethylcarbonyl group, a pentafluoroethylcarbonyl group, a benzoyl group, and a naphthoyl group. It is preferable that all of R 1 to R 8 in the formula (1) are hydrogen atoms.
- the divalent linking group that is not conjugated to the benzene ring represented by X in the formula (1) is not particularly limited.
- a VI group element such as an oxygen atom
- a divalent substituent such as a sulfonyl group or an alkylene group
- a direct bond refers to the case where two benzene rings in Formula (1) are bonded via no linking group; the same shall apply hereinafter) is also included in the category of the divalent linking group.
- the divalent linking groups X that the polysulfonamide compound has in its structure may be the same or different.
- the divalent linking group that is not conjugated to the benzene ring represented by X in the formula (1) is preferably an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, a methylene group, or a direct bond, More preferably, it is more preferably an oxygen atom.
- the divalent aromatic residue represented by Y in the formula (1) means a residue obtained by removing two hydrogen atoms from the aromatic ring of the aromatic.
- Aromatics that can be divalent aromatic residues include not only aromatic rings such as benzene and naphthalene, but also aromatics in which multiple aromatic rings such as diphenyl ether, diphenylmethane, and biphenyl are bonded via a linking group or directly. It is.
- the divalent aromatic residue Y which the polysulfonamide compound has in its structure may be the same or different.
- Y in the formula (1) is preferably a divalent aromatic residue represented by the following formula (2).
- R 9 to R 16 each independently represents a hydrogen atom or a monovalent organic group.
- Y ′ represents a direct bond, an oxygen atom, a carbonyl group, a methylene group, a sulfur atom or a sulfonyl group.
- Y 'which plural polysulfonamide compounds have in the structure may be the same or different.
- Examples of the monovalent organic group represented by R 9 to R 16 in the formula (2) include the same monovalent organic groups represented by R 1 to R 8 in the formula (1). All of R 9 to R 16 in Formula (2) are preferably hydrogen atoms. Y ′ in Formula (2) is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
- the number of the repeating unit of the formula (1) possessed by the polysulfonamide compound of the present invention is not particularly limited as long as it is plural, but is preferably a number so as to satisfy the range of the preferred number average molecular weight described later. .
- the method for producing the polysulfonamide compound of the present invention is not particularly limited, but a general method is to convert a disulfonic acid derivative into a dihalide derivative using a halogenating agent and then react the diamine with the dihalide derivative.
- a dichloride derivative is preferable.
- the halogenating agent that can be used when the disulfonic acid derivative is converted to the dichloride derivative include thionyl chloride, phosphoryl chloride, and phosphorus oxychloride, which are used in a normal acid chloride reaction.
- the dichloride derivative can be synthesized by directly reacting an aromatic compound with chlorosulfonic acid.
- Examples of the disulfonic acid derivative that can be used in producing the polysulfonamide compound of the present invention include the following compound No. Examples thereof include, but are not limited to, disulfonic acids represented by 1 to 6. These disulfonic acids can be used alone or in combination of two or more.
- the reaction between the dihalide derivative and the diamine is desirably performed in an organic solvent in the presence of a dehalogenating agent.
- a dehalogenating agent organic bases such as pyridine, picoline and triethylamine can be usually used.
- organic solvent sulfolane, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N, N-dimethylformamide and the like can be used.
- the concentration of the reaction solution is preferably 20 to 50% by mass, more preferably 30 to 40% by mass.
- diamines are first dissolved in an organic solvent. After cooling this solution to 0 ° C. or lower, a dihalide derivative is added.
- the temperature at which the dihalide derivative is added is preferably ⁇ 20 to 0 ° C., more preferably ⁇ 15 to ⁇ 5 ° C.
- the reaction temperature between the dihalide derivative and the diamine is preferably -20 to 60 ° C, more preferably -10 to 30 ° C.
- the reaction time is preferably 30 minutes to 24 hours, more preferably 1 hour to 8 hours.
- Both ends of the polysulfonamide compound of the present invention obtained by the reaction of a dichloride derivative and diamines may be either an amino group or a sulfonyl group.
- the polysulfonamide compound having amino groups at both ends can be obtained by using an excess molar amount of diamine with respect to the dichloride derivative when the dichloride derivative is reacted with the diamine.
- a polysulfonamide compound having a sulfonyl group at both ends can be obtained by using an excess molar amount of a dichloride derivative with respect to the diamine when the dichloride derivative is reacted with the diamine.
- the terminal structure of the polysulfonamide compound can be distinguished by 1 H-NMR.
- the molecular weight of the polysulfonamide compound of the present invention can be controlled by the molar ratio of the dichloride derivative used in the reaction and the diamine. Specifically, the molecular weight of the resulting polysulfonamide compound decreases as the difference in molar amount between the dichloride derivative and the diamine increases, and the molecular weight of the resulting polysulfonamide compound increases as the difference in molar amount decreases.
- the number average molecular weight of the polysulfonamide compound of the present invention is preferably 3,000 to 100,000, and more preferably 8,000 to 50,000.
- the number average molecular weight here is a value obtained by measurement by gel permeation chromatography and conversion from a standard polystyrene calibration curve.
- the resin composition of the present invention comprises a polysulfonamide compound having a repeating unit represented by formula (1) and a component other than the polysulfonamide compound (hereinafter, the component other than the polysulfonamide compound is simply referred to as “other component”). Contain).
- other components contained in the resin composition of the present invention include adhesion enhancers such as organic solvents, crosslinking agents, acid generators, and coupling agents.
- adhesion enhancers such as organic solvents, crosslinking agents, acid generators, and coupling agents.
- a resin composition containing an organic solvent is preferred because it is easy to handle.
- the organic solvent that can be contained in the resin composition of the present invention is not particularly limited.
- organic solvents can be used alone or in combination of two or more.
- the content of the organic solvent in the resin composition of the present invention is not particularly limited. Usually, the content of the solvent in the resin composition is more than 0% by mass and 95% by mass or less, preferably 20 to 90% by mass. is there.
- the crosslinking agent that can be contained in the resin composition of the present invention is a compound having two or more substituents that can be crosslinked or polymerized with the polysulfonamide compound of the present invention in its structure.
- the crosslinking agent is preferably a crosslinking agent having a substituent that can be crosslinked or polymerized by heating.
- the crosslinking agent is preferably a compound capable of undergoing a polymerization reaction between substituents of the crosslinking agent not involved in the crosslinking or polymerization reaction with the polysulfonamide compound of the present invention, that is, a compound capable of self-polymerization.
- the crosslinking agent may be either a low molecular weight compound or a high molecular weight compound such as resins.
- the substituent which a crosslinking agent has will not be specifically limited if it is a substituent which can be bridge
- the crosslinking agent that can be contained in the resin composition of the present invention includes a compound in which the above substituent is bonded to a benzene ring, a melamine resin in which the N-position is substituted with a methylol group and / or an alkoxymethyl group, and a urea resin. Etc. are preferred.
- Specific examples of preferred crosslinking agents include compounds represented by the following formulas (3) to (5).
- G represents a monovalent to tetravalent organic group.
- R 17 and R 18 each independently represent a hydrogen atom or a monovalent organic group.
- o represents an integer of 1 to 4
- p and q each independently represents an integer of 0 to 4.
- Examples of the monovalent organic group represented by G, R 17 and R 18 in the formula (3) include the same monovalent organic groups represented by R 1 to R 8 in the formula (1).
- Examples of the divalent to tetravalent organic group represented by G in the formula (3) include an oxygen atom, a sulfur atom, a carbon atom, a methyl group, a methylene group, an isopropylidene group, a hexafluoroisopropylidene group, and a benzal group. It is done.
- each J independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group or an alkoxyalkoxyalkyl group, and the hydrogen atom in these substituents is fluorine It may be substituted with an atom.
- R 19 to R 22 each independently represents a hydrogen atom or a monovalent organic group. r and s each independently represent an integer of 1 to 3, and p and q each independently represents an integer of 0 to 4. Examples of the monovalent organic group represented by R 19 to R 22 in the formula (4) include the same monovalent organic groups represented by R 1 to R 8 in the formula (1).
- R 23 and R 24 each independently represent a hydrogen atom or a monovalent organic group, and R 24 may be bonded to each other to form a ring structure.
- Examples of the monovalent organic group represented by R 23 and R 24 in the formula (5) include the same monovalent organic groups represented by R 1 to R 8 in the formula (1).
- crosslinking agent represented by the formulas (3) to (5) for example, the following compound No. Although the compound represented by 13 thru
- the content of the crosslinking agent in the resin composition of the present invention is usually more than 0 parts by mass with respect to 100 parts by mass of the polysulfonamide compound from the viewpoints of development time, allowable width of unexposed part remaining film ratio, and cured film physical properties. And 70 parts by mass or less, preferably 1 to 50 parts by mass.
- any compound that generates an acid by light or heat can be used as the acid generator that can be contained in the resin composition of the present invention.
- a compound that generates an acid by light is desirable.
- the acid generator include, but are not limited to, diarylsulfonium salts, triarylsulfonium salts, dialkylphenacylsulfonium salts, diaryliodonium salts, aryldiazonium salts, aromatic tetracarboxylic acid esters, aromatic sulfonic acid esters, Nitrobenzyl ester, oxime sulfonic acid ester (for example, aromatic oxime sulfonic acid ester), aromatic N-oxyimide sulfonate, aromatic sulfamide, haloalkyl group-containing hydrocarbon compound, haloalkyl group-containing heterocyclic compound and naphthoquinodi And azido-4-sulfonic acid ester.
- diarylsulfonium salts triarylsulfonium salts
- dialkylphenacylsulfonium salts diaryliodonium salts
- aryldiazonium salts aromatic tetracar
- These acid generators can be used in combination of two or more as required, or in combination with other sensitizers. Among them, it is preferable to use an aromatic oxime sulfonic acid ester, an aromatic N-oxide imide sulfonate, or the like because an effect of improving the sensitivity of the photosensitive resin composition can be expected.
- the content of the acid generator in the resin composition of the present invention is usually 10 parts by mass or less, preferably 1 to 5 parts by mass with respect to 100 parts by mass of the polysulfonamide compound.
- the adhesion enhancer that can be contained in the resin composition of the present invention is a compound that can improve the adhesion of the composition to the substrate. Although it does not specifically limit as an adhesion
- the silane coupling agent is not particularly limited, but 3-chloropropyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyltrimethoxysilane, vinyl tris (2-methoxyethoxy) silane, 3-methacryloxy Propyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-2- (Aminoethyl) -3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane and the like.
- adhesion enhancing agents can be used alone or in combination of two or more. Since the adhesion enhancer is unreactive with the main component, components other than those acting at the substrate interface may exist as residual components after curing. Therefore, if the adhesion enhancer is used in a large amount, there is a risk of adverse effects such as deterioration of physical properties. Depending on the type of the substrate, it is appropriate to use it within a range that does not adversely affect the effect even in a small amount.
- the use ratio is typically more than 0% by mass and 15% by mass or less, more preferably more than 0% by mass and 5% by mass or less, based on the resin composition. The preferable upper limit of the use ratio can vary depending on the type of substrate.
- thermoplastic resins examples include polyethersulfone, polystyrene, and polycarbonate.
- colorant examples include phthalocyanine blue, phthalocyanine green, iodin green, crystal violet, titanium oxide, carbon black, naphthalene black and the like.
- thickener examples include olben, benton, montmorillonite and the like.
- antifoaming agent examples include silicone-based, fluorine-based and polymer-based antifoaming agents.
- the amount of these additives used in the resin composition of the present invention is, for example, preferably from 0 to 30% by mass, but may be appropriately increased or decreased depending on the purpose of use.
- the resin composition of the present invention includes, for example, barium sulfate, barium titanate, silicon oxide, amorphous silica, talc, clay, magnesium carbonate, calcium carbonate, aluminum oxide, aluminum hydroxide, mica
- An inorganic filler such as powder can be used.
- the blending ratio of the inorganic filler is preferably 0% by mass or more and 60% by mass or less in the resin composition of the present invention.
- the number average molecular weight of the polysulfonamide compound in the examples is a value obtained by standard polystyrene conversion based on the measurement result of gel permeation chromatography (Tosoh HLC-8220 GPC column: TOSOH TSK-GEL Super AWM-H). It is.
- the “parts” indicating the following amounts mean “parts by mass” unless otherwise specified.
- Example 1 Synthesis of Polysulfonamide Compound of the Present Invention
- 8.04 parts 40 mmol of 3,4'-diaminodiphenyl ether, 2- 11.176 parts (120 mmol) of picoline and 18.9 parts of N-methyl-2-pyrrolidone were added, dissolved by stirring and then cooled to ⁇ 10 ° C.
- 14.688 parts 40 mmol of 4,4′-oxybisbenzenesulfonyl chloride and 16.0 parts of N-methyl-2-pyrrolidone were added.
- Polymer I The polysulfonamide compound of the present invention.
- the number average molecular weight of the polymer I was 24,000, and the molecular weight distribution was 2.13.
- the obtained polymer I showed good solubility in a 2.38% TMAH aqueous solution.
- Comparative Example 1 Synthesis of Comparative Polyamide Compound
- a mechanical stirrer, thermometer and nitrogen introduction tube 4.013 part (20 mmol) of 3,4′-diaminodiphenyl ether, 2-picoline
- 5.588 parts (60 mmol) and 22.14 parts of N-methyl-2-pyrrolidone were charged, dissolved by stirring and then cooled to ⁇ 10 ° C.
- Example 2 Production of resin composition of the present invention 100 parts of polymer I obtained in Example 1, DML-PC-MF (manufactured by Honshu Chemical Industry Co., Ltd., 2,6-bis (hydroxyphenyl)-) as a crosslinking agent p-cresol) 20 parts, DM-BIPC-F (Asahi Organic Materials Co., Ltd., bis (2-hydroxy-3-hydroxymethyl-5-methylphenyl) methane) as a crosslinking agent and PAG- as a photoacid generator 103 parts (manufactured by BASF, 2- [2- (propylsulfonyloxyimino) thiophene-3- (2H) -ylidene] -2- (2-methylphenyl) acetonitrile) in 207 parts of ⁇ -butyrolactone were dissolved. A resin composition of the present invention was obtained.
- Comparative Example 2 Production of Comparative Resin Composition 100 parts of Polymer II obtained in Comparative Example 1, DML-PC-MF (Honshu Chemical Co., Ltd., 2,6-bis (hydroxyphenyl)-) as a crosslinking agent p-cresol) 20 parts, DM-BIPC-F (Asahi Organic Materials Co., Ltd., bis (2-hydroxy-3-hydroxymethyl-5-methylphenyl) methane) as a crosslinking agent and PAG- as a photoacid generator 103 parts (manufactured by BASF, 2- [2- (propylsulfonyloxyimino) thiophene-3- (2H) -ylidene] -2- (2-methylphenyl) acetonitrile) in 207 parts of ⁇ -butyrolactone were dissolved. A comparative resin composition was obtained.
- Example 3 Patterning evaluation The resin composition obtained in Example 2 was applied onto a silicon wafer with a spinner and dried on a hot plate at 75 ° C for 15 minutes to obtain a film having a thickness of 10 ⁇ m. A photomask for resolution evaluation was placed on this film, irradiated with ultraviolet rays of 250 mJ / cm 2 , and then heated on a hot plate at 60 ° C. for 3 minutes and on a hot plate at 100 ° C. for 2 minutes.
- the film on the obtained silicon wafer was developed with an aqueous 2.38% tetramethylammonium hydroxide solution, and further rinsed with distilled water, whereby a pattern with a resolution L & S of 6 ⁇ m and an aspect ratio of 1.58 was obtained. . No peeling or the like was observed during development on the obtained pattern, and the adhesion to the silicon wafer was good.
- Comparative Example 3 Patterning Evaluation When the resin composition obtained in Comparative Example 2 was evaluated in the same manner as in Example 3, it could not be developed with an aqueous 2.38% tetramethylammonium hydroxide solution. The pattern could not be obtained.
- a cured film of the resin composition of the present invention was produced on a Kapton film in the same procedure as the above-described patterning evaluation except that a photomask for resolution evaluation was not placed.
- the obtained cured film was peeled off from the Kapton film and heat-treated in an oven at 200 ° C. for 1 hour.
- RTG-1210 Tensilon universal testing machine
- the elongation at break was 8.8% and the break strength was 100 MPa, which was excellent.
- the glass transition temperature (Tg) evaluated by using a dynamic viscoelasticity measuring device (DMA) (RSA-G2 manufactured by TA Instruments) is 248 ° C., and has excellent heat resistance. I understood.
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Abstract
Description
本発明の第二の目的は、この新規なポリスルホンアミド化合物を含む樹脂組成物、及びこれを用いて形成された硬化物を提供することである。
下記式(1)
(式(1)中、R1~R8は、それぞれ独立に水素原子又は一価の有機基を表す。Xは、結合するベンゼン環と共役しない二価の連結基を表す。Yは、二価の芳香族残基を表す。)で示される繰り返し単位を有する、ポリスルホンアミド化合物。
[2].
Yが、下記式(2)
(式(2)中、R9~R16は、それぞれ独立に水素原子又は一価の有機基を表す。Y’は、直接結合、酸素原子、カルボニル基、メチレン基、硫黄原子又はスルホニル基を表す。)で示される二価の芳香族残基である、前項[1]に記載のポリスルホンアミド化合物。
[3].
Xが、酸素原子、硫黄原子、スルホニル基、カルボニル基、メチレン基又は直接結合である、前項[1]又は[2]に記載のポリスルホンアミド化合物。
[4].
前項[1]~[3]のいずれか一項に記載のポリスルホンアミド化合物及び該ポリスルホンアミド化合物以外の成分を含有する、樹脂組成物。
[5].
有機溶剤を含有する、前項[4]に記載の樹脂組成物。
[6].
架橋剤を含有する、前項[4]又は[5]に記載の樹脂組成物。
[7].
酸発生剤を含有する、前項[4]~[6]のいずれか一項に記載の樹脂組成物。
[8].
前項[4]~[7]のいずれか一項に記載の樹脂組成物の硬化物。
また、本発明による好ましいポリスルホンアミド化合物は、閉環反応を必要としないため、該化合物を含む樹脂組成物を用いることにより、優れた解像度及び硬化膜物性を有するパターンを形成することができる。そのうえ、本発明のポリスルホンアミド化合物は、水系の現像液での現像が可能であるため、環境に優しい。
式(1)のR1~R8が表す一価の有機基であるアリールオキシ基としては、特に限定されないが、フェノキシ基及びナフトキシ基等が挙げられる。
式(1)のR1~R8が表す一価の有機基であるアルコキシカルボニル基としては、特に限定されないが、例えば炭素数1~10のアルコキシカルボニル基等が挙げられる。その具体例としてはメトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、イソプロポキシカルボニル基、n-ブトキシカルボニル基、イソブトキシカルボニル基、sec-ブトキシカルボニル基、t-ブトキシカルボニル基、n-ペントキシカルボニル基、n-ヘキシルオキシカルボニル基、n-ヘプチルオキシカルボニル基、n-ノニルオキシカルボニル基及びn-デシルオキシカルボニル基等である。
式(1)のR1~R8が表すアシル基としては、特に限定されないが、例えば炭素数1~10のアルキルカルボニル基、アリールカルボニル基等が挙げられる。好ましくは炭素数1~4のアルキルカルボニル基で、具体的にはアセチル基、プロピオニル基、トリフルオロメチルカルボニル基、ペンタフルオロエチルカルボニル基、ベンゾイル基、ナフトイル基等が挙げられる。
式(1)におけるR1~R8としては、全てが水素原子であることが好ましい。
式(1)のXが表すベンゼン環と共役しない二価の連結基としては、酸素原子、硫黄原子、スルホニル基、カルボニル基、メチレン基又は直接結合であることが好ましく、酸素原子又は硫黄原子であることがより好ましく、酸素原子であることが更に好ましい。
式(2)におけるR9~R16としては、全てが水素原子であることが好ましい。
式(2)におけるY’としては、酸素原子又は硫黄原子であることが好ましく、酸素原子であることがより好ましい。
ジハライド誘導体としてはジクロリド誘導体が好ましい。ジスルホン酸誘導体をジクロリド誘導体に変換する際に用い得るハロゲン化剤としては、通常の酸クロリド化反応に使用される塩化チオニル、塩化ホスホリル及びオキシ塩化リン等が挙げられる。
また、ジクロリド誘導体は、芳香族化合物にクロロスルホン酸を直接反応させて合成することができる。
両末端がアミノ基のポリスルホンアミド化合物は、ジクロリド誘導体とジアミン類とを反応させる際に、ジクロリド誘導体に対して過剰のモル量のジアミン類を用いることにより得ることが出来る。一方、両末端がスルホニル基のポリスルホンアミド化合物は、ジクロリド誘導体とジアミン類とを反応させる際に、ジアミン類に対して過剰のモル量のジクロリド誘導体を用いることにより得ることが出来る。尚、ポリスルホンアミド化合物の末端構造は1H-NMRによって判別することができる。
本発明のポリスルホンアミド化合物の数平均分子量は、3,000~100,000であることが好ましく、8,000~50,000であることがより好ましい。ここでいう数平均分子量は、ゲルパーミエーションクロマトグラフィー法により測定を行い、標準ポリスチレン検量線から換算して得た値である。
本発明の樹脂組成物が含有するその他成分としては、例えば有機溶剤、架橋剤、酸発生剤及びカップリング剤等の密着増強剤等が挙げられる。樹脂組成物の用途や用法に合せて、前記以外の各種成分も特に制限なく用いることができる。ハンドリングが容易であることから、有機溶剤を含有する樹脂組成物が好ましい。
本発明の樹脂組成物における有機溶剤の含有量に特に制限はないが、通常は、樹脂組成物中の溶剤の含有量が0質量%超かつ95質量%以下、好ましくは20~90質量%である。
本発明の樹脂組成物が含有し得る架橋剤としては、前記の置換基がベンゼン環に結合している化合物、N位がメチロール基及び/ 又はアルコキシメチル基で置換されたメラミン樹脂、及び尿素樹脂等が好ましい。
好ましい架橋剤の具体例としては、下記式(3)~(5)で表される化合物が挙げられる。
式(3)中、Gは一価~四価の有機基を表す。R17及びR18はそれぞれ独立に水素原子又は一価の有機基を表す。oは1~4の整数を表し、p及びqはそれぞれ独立に0~4の整数を表す。
式(3)のG、R17及びR18が表す一価の有機基としては、式(1)のR1~R8が表す一価の有機基と同じものが挙げられる。
式(3)のGが表す二価~四価の有機基としては、例えば酸素原子、硫黄原子、炭素原子、メチル基、メチレン基、イソプロピリデン基、ヘキサフルオロイソプロピリデン基、ベンザル基等が挙げられる。
式(4)中、Jは、それぞれ独立に水素原子又は炭素原子数1~10のアルキル基、アルコキシ基、アルコキシアルキル基若しくはアルコキシアルコキシアルキル基を表し、これらの置換基中の水素原子は、フッ素原子で置換されていてもよい。R19~R22は、各々独立に水素原子又は一価の有機基を表す。r及びsはそれぞれ独立に1~3の整数を表し、p及びqはそれぞれ独立に0~4の整数を表す。
式(4)のR19~R22が表す一価の有機基としては、式(1)のR1~R8が表す一価の有機基と同じものが挙げられる。
式(5)中、R23及びR24はそれぞれ独立に水素原子又は一価の有機基を表し、R24同士で結合して環構造を形成してもよい。
式(5)のR23及びR24が表す一価の有機基としては、式(1)のR1~R8が表す一価の有機基と同じものが挙げられる。
これらの架橋剤は、単独で又は2種類以上を組み合わせて使用することができる。
本発明の樹脂組成物における酸発生剤の含有量は、ポリスルホンアミド化合物100質量部に対して通常10質量部以下、好ましくは1~5質量部である。
密着増強剤は、主成分とは未反応性のものであるため、基材界面で作用する成分以外は硬化後に残存成分として存在することになり得る。従って、密着増強剤は、多量に使用すると物性低下などの悪影響を及ぼす恐れがある。基材の種類によっては、少量でも効果を発揮する点から、悪影響を及ぼさない範囲内での使用が適当である。その使用割合は、樹脂組成物に対して典型的には0質量%超かつ15質量%以下が好ましく、より好ましくは0質量%超かつ5質量%以下である。この使用割合の好ましい上限は、基材の種類によって変動し得る。
尚、実施例におけるポリスルホンアミド化合物の数平均分子量は、ゲルパーミエーションクロマトグラフィー(東ソー HLC-8220 GPC カラム:TOSOH TSK-GEL Super AWM-H)の測定結果に基づいて、標準ポリスチレン換算により求めた値である。
下記の量を示す「部」は、特に断らない限り、「質量部」を意味する。
メカニカルスターラー、温度計及び窒素導入管を備えた0.5リットルのフラスコに、3,4’-ジアミノジフェニルエーテル8.010部(40mmol)、2-ピコリン11.176部(120mmol)及びN―メチル-2-ピロリドン18.9部を仕込み、撹拌溶解させた後-10℃まで冷却した。得られた溶液の温度を-10~-5℃に保ちながら、4,4’-オキシビスベンゼンスルホニルクロライド14.688部(40mmol)及びN―メチル-2-ピロリドン16.0部を添加した後、溶液の温度を0~5℃に保ちながら1時間撹拌を続けた。得られた溶液を4リットルの水に投入し、析出物を回収して純水で3回洗浄した後、60℃の恒温槽で乾燥させることにより本発明のポリスルホンアミド化合物(以下、「ポリマーI」と記載する)を得た。ポリマーIの数平均分子量は24,000、分子量分布は2.13であった。
得られたポリマーIは、TMAH 2.38%水溶液に対する良好な溶解性を示した。
メカニカルスターラー、温度計及び窒素導入管を備えた0.5リットルのフラスコに、3,4’-ジアミノジフェニルエーテル4.013部(20mmol)、2-ピコリン5.588部(60mmol)及びN―メチル-2-ピロリドン22.14部を仕込み、撹拌溶解させた後-10℃まで冷却した。得られた溶液の温度を-10~-5℃に保ちながら、4,4’-オキシビスベンゾイルクロライド5.902部(20mmol)及びN―メチル-2-ピロリドン8部を添加した後、溶液の温度を0~5℃に保ちながら0.5時間撹拌を続けた。得られた溶液を4リットルの水に投入し、析出物を回収して純水で3回洗浄した後、60℃の恒温槽で乾燥させることにより比較用のポリアミド化合物(以下、「ポリマーII」と記載する)を得た。ポリマーIIの数平均分子量は13,000、分子量分布は4.82であった。
得られたポリマーIIは、TMAH 2.38%水溶液に対して不溶であった。
実施例1で得られたポリマーI 100部、架橋剤としてDML-PC-MF(本州化学工業社製、2,6-ビス(ヒドロキシフェニル)-p-クレゾール)20部、架橋剤としてDM-BIPC-F(旭有機材社製、ビス(2-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン)20部及び光酸発生剤としてPAG-103(BASF社製、2-[2-(プロピルスルホニルオキシイミノ)チオフェン-3-(2H)-イリデン]-2-(2-メチルフェニル)アセトニトリル)4部をγ―ブチロラクトン207部に溶解して本発明の樹脂組成物を得た。
比較例1で得られたポリマーII 100部、架橋剤としてDML-PC-MF(本州化学工業社製、2,6-ビス(ヒドロキシフェニル)-p-クレゾール)20部、架橋剤としてDM-BIPC-F(旭有機材社製、ビス(2-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン)20部及び光酸発生剤としてPAG-103(BASF社製、2-[2-(プロピルスルホニルオキシイミノ)チオフェン-3-(2H)-イリデン]-2-(2-メチルフェニル)アセトニトリル)4部をγ―ブチロラクトン207部に溶解して比較用の樹脂組成物を得た。
実施例2で得られた樹脂組成物をシリコンウエハー上にスピンナーで塗布し、75℃のホットプレート上で15分間乾燥し、厚さ10μmのフィルムを得た。このフィルム上に解像度評価用のフォトマスクを載置し、250mJ/cm2の紫外線を照射した後60℃のホットプレート上で3分間、及び100℃のホットプレート上で2分間加熱した。得られたシリコンウエハー上のフィルムを2.38%テトラメチルアンモニウムヒドロキシド水溶液で現像し、更に蒸留水でリンスを施すことにより、解像度L&Sで6μm、アスペクト比が1.58のパターンが得られた。得られたパターンに現像時の剥がれ等は観察されず、シリコンウエハーに対する密着性は良好であった。
比較例2で得られた樹脂組成物を実施例3と同様の方法で評価を行ったところ、2.38%テトラメチルアンモニウムヒドロキシド水溶液で現像することができず、パターンを得ることができなかった。
解像度評価用のフォトマスクを載置しなかったこと以外は上記したパターニング評価と同様の手順で、カプトンフィルム上に本発明の樹脂組成物の硬化膜を作製した。得られた硬化膜をカプトンフィルム上から剥離し、200℃のオーブンで1時間加熱処理した。テンシロン万能試験機(エー・アンド・デイ社製 RTG-1210)を用いて機械物性を評価したところ、破断点伸度8.8%、破断強度100MPaと機械物性に優れていることが分かった。
また、動的粘弾性測定装置(DMA)(ティー・エイ・インスツルメント社製 RSA-G2)を用いて評価したガラス転移温度(Tg)は248℃であり、耐熱性に優れていることが分かった。
Claims (8)
- Xが、酸素原子、硫黄原子、スルホニル基、カルボニル基、メチレン基又は直接結合である、請求項1又は2に記載のポリスルホンアミド化合物。
- 請求項1~3のいずれか一項に記載のポリスルホンアミド化合物及び該ポリスルホンアミド化合物以外の成分を含有する、樹脂組成物。
- 有機溶剤を含有する、請求項4に記載の樹脂組成物。
- 架橋剤を含有する、請求項4又は5に記載の樹脂組成物。
- 酸発生剤を含有する、請求項4~6のいずれか一項に記載の樹脂組成物。
- 請求項4~7のいずれか一項に記載の樹脂組成物の硬化物。
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- 2016-10-06 KR KR1020187009136A patent/KR20180063101A/ko unknown
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- 2016-10-06 WO PCT/JP2016/079836 patent/WO2017061561A1/ja active Application Filing
- 2016-10-06 JP JP2017544229A patent/JP6860491B2/ja active Active
- 2016-10-06 TW TW105132436A patent/TWI773653B/zh active
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JP2019518981A (ja) * | 2016-05-12 | 2019-07-04 | ノーロッキー, ダニエル, ジェイ.NAWROCKI, Daniel, J. | ポリスルホンアミド再分布組成物及びその使用方法 |
TWI802540B (zh) * | 2017-05-12 | 2023-05-21 | 丹尼爾 J 納羅奇 | 聚磺醯胺重分佈組合物及其用途 |
WO2023120292A1 (ja) * | 2021-12-21 | 2023-06-29 | 国立大学法人東京工業大学 | 光スルホンアミド合成反応 |
WO2023190879A1 (ja) * | 2022-03-31 | 2023-10-05 | 太陽ホールディングス株式会社 | ネガ型感光性樹脂組成物、ドライフィルム、硬化物及び電子部品 |
Also Published As
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EP3360915A4 (en) | 2019-05-15 |
JPWO2017061561A1 (ja) | 2018-08-02 |
US20180273685A1 (en) | 2018-09-27 |
JP6860491B2 (ja) | 2021-04-14 |
TW201728629A (zh) | 2017-08-16 |
US10782612B2 (en) | 2020-09-22 |
EP3360915A1 (en) | 2018-08-15 |
CN108137809A (zh) | 2018-06-08 |
TWI773653B (zh) | 2022-08-11 |
KR20180063101A (ko) | 2018-06-11 |
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