WO2023032467A1 - Composition de résine, film de composition de résine, film durci et dispositif à semi-conducteur - Google Patents

Composition de résine, film de composition de résine, film durci et dispositif à semi-conducteur Download PDF

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Publication number
WO2023032467A1
WO2023032467A1 PCT/JP2022/026925 JP2022026925W WO2023032467A1 WO 2023032467 A1 WO2023032467 A1 WO 2023032467A1 JP 2022026925 W JP2022026925 W JP 2022026925W WO 2023032467 A1 WO2023032467 A1 WO 2023032467A1
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resin composition
component
film
group
compound
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PCT/JP2022/026925
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English (en)
Japanese (ja)
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加藤圭悟
松村和行
楯岡佳子
嶋田彰
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東レ株式会社
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Priority to JP2022542672A priority Critical patent/JPWO2023032467A1/ja
Publication of WO2023032467A1 publication Critical patent/WO2023032467A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/12—Mountings, e.g. non-detachable insulating substrates
    • H01L23/14—Mountings, e.g. non-detachable insulating substrates characterised by the material or its electrical properties

Definitions

  • the present invention relates to resin compositions, resin composition films, cured films, and semiconductor devices. More particularly, the present invention relates to resin compositions suitably used for surface protective films of semiconductor elements and inductor devices, interlayer insulating films, structures of MEMS (Micro Electro Mechanical Systems), and the like.
  • MEMS Micro Electro Mechanical Systems
  • Patent Document 1 a chemically amplified photo-cationically polymerizable photosensitive material
  • Patent Document 2 a photocationic polymerizable material intended to improve mechanical properties and thermal properties by containing an epoxy resin with a specific structure
  • Patent Document 3 a cationic photopolymerizable material having excellent heat resistance and tensile elongation is disclosed by containing a polymer compound such as polyimide and an epoxy compound having a specific structure
  • Patent Documents 2 and 3 are capable of photocationic polymerization that achieves both sufficient adhesion and sensitivity during pattern processing. No material was obtained.
  • the present invention for solving the above problems is as follows.
  • the resin composition of the present invention provides a resin composition, a resin composition film, a cured film, and a semiconductor device that exhibit sufficient adhesion to inorganic substrates and sensitivity during pattern processing.
  • the present invention is a resin composition containing a polymer compound as component (A), a cationic polymerizable compound as component (B), a cationic polymerization initiator as component (C), and a silane coupling agent as component (D).
  • the resin composition is characterized in that the component (D) has a carboxyl group and/or an acid anhydride group.
  • the resin composition of the present invention contains a polymer compound as the (A) component, so that it is excellent in film formability when formed into a film.
  • the weight average molecular weight of component (A) is not particularly limited as long as it is a polymer compound, but the weight average molecular weight is preferably 1,000 or more and 200,000 or less.
  • (A) component may be used individually or may use 2 or more types together.
  • the weight average molecular weight of component (A) in the present invention is measured by gel permeation chromatography (GPC method) and calculated in terms of polystyrene.
  • component (A) is preferably at least one compound selected from the group consisting of polyamide, polyimide, and polyamideimide. If at least one compound selected from the group consisting of polyamides, polyimides, and polyamideimides is included as the component (A), the component (A) can also include polymer compounds other than polyamides, polyimides, and polyamideimides. .
  • the polyimide precursor and the polybenzoxazole precursor each correspond to the polyamide described above.
  • the component (A) preferably has a carboxylic acid residue at the molecular chain end. Since the molecular chain end of component (A) is a carboxylic acid residue, the molecular chain end can have a molecular structure that does not possess an amine terminal structure, which can serve as an inhibitory functional group for cationic polymerization. It is preferable because sufficient cationic polymerizability can be expressed.
  • the expression that the molecular chain end of component (A) is a carboxylic acid residue means that the molecular chain end of component (A) is an organic group derived from a carboxylic acid capable of constituting polyamide, polyimide or polyamideimide.
  • the molecular chain end of component (A) is a carboxylic acid residue specifically means that the molecular chain end of component (A) is a monocarboxylic acid, a dicarboxylic acid, a monoacid chloride compound, a diacid chloride compound, It means an organic group derived from a tetracarboxylic acid, an acid anhydride, an acid dianhydride, or the like.
  • Carboxylic acids suitable for forming carboxylic acid residues at the molecular chain ends of component (A) include aromatic dicarboxylic acids, aromatic dianhydrides, alicyclic dicarboxylic acids, and alicyclic dianhydrides. compounds, aliphatic dicarboxylic acids, aliphatic dianhydrides, and the like, but are not limited to these. Moreover, these are used individually or in combination of 2 or more types.
  • the component (A) is preferably a compound having at least one structure selected from structures represented by general formula (1) and general formula (2).
  • X 1 and X 2 independently represent a divalent to 10-valent organic group
  • X 2 represents a 4- to 10-valent organic group
  • Y 1 and Y 2 each independently represents a divalent to tetravalent organic group
  • R represents a hydrogen atom or an organic group having 1 to 20 carbon atoms
  • q is an integer of 0 to 2
  • r, s, t and u are Each is independently an integer from 0 to 4.
  • Y 1 and Y 2 in general formulas (1) and (2) each represent a divalent to tetravalent organic group, and represent an organic group derived from diamine.
  • Y1 and Y2 in general formulas ( 1 ) and ( 2 ) of component (A) preferably contain a diamine residue having a phenolic hydroxyl group.
  • a diamine residue having a phenolic hydroxyl group in the component (A) moderate solubility of the resin in an alkaline developer can be obtained, so that a high contrast between the exposed and unexposed areas can be obtained. pattern can be formed.
  • diamines having a phenolic hydroxyl group include bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(3-amino- 4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, bis(3-amino-4-hydroxy)biphenyl, 2,2'- Ditrifluoromethyl-5,5'-dihydroxyl-4,4'-diaminobiphenyl, bis(3-amino-4-hydroxyphenyl)fluorene, 2,2'-bis(trifluoromethyl)-5,5'- Aromatic diamines such as dihydroxybenzidine, compounds in which some of the hydrogen atoms of these aromatic rings or hydrocarbons are substituted with alkyl groups having 1 to 10 carbon atoms, fluoroalkyl groups, halogen
  • Y 1 and Y 2 in general formulas (1) and (2) may contain a diamine residue having an aromatic group other than those mentioned above. Heat resistance can be improved by copolymerizing these.
  • aromatic diamine residues include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 3,4 '-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 1,4-bis(4-aminophenoxy)benzene, benzine, m- phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenedi
  • aromatic diamines and compounds in which some of the hydrogen atoms of these aromatic rings or hydrocarbons are substituted with an alkyl group having 1 to 10 carbon atoms, a fluoroalkyl group, a halogen atom, or the like. It is not limited to these.
  • Other diamines to be copolymerized can be used as they are or as corresponding diisocyanate compounds, trimethylsilylated diamines. Moreover, you may use combining these 2 or more types of diamine components.
  • X 1 and X 2 are preferably carboxylic acid residues independently, and X 1 is a divalent to decavalent organic is preferred, and X 2 is preferably a tetravalent to decavalent organic group.
  • the carboxylic acid residue preferably has a structure derived from an alicyclic tetracarboxylic dianhydride. That is, (A) the polymer compound is at least one compound selected from the group consisting of polyamide, polyimide, and polyamideimide, and further preferably has a structure derived from an alicyclic tetracarboxylic dianhydride. .
  • the carboxylic acid residue has a structure derived from an alicyclic tetracarboxylic dianhydride, the light transmittance of the resin composition with respect to the exposure wavelength is increased, and processing into a thick film of 20 ⁇ m or more is facilitated. .
  • the (A) polymer compound has a structure derived from an alicyclic tetracarboxylic dianhydride, so that the reactivity of cationic polymerization is higher than that of an aromatic dianhydride. It is preferable in that it increases and the chemical resistance of the cured film is improved.
  • alicyclic tetracarboxylic dianhydrides having a polycyclic structure improve chemical resistance when cured and improve ion migration resistance. is preferably
  • organic group derived from an alicyclic tetracarboxylic dianhydride having a polycyclic structure include 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3 ,4-tetrahydronaphthalene-1,2-dicarboxylic dianhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-4methyl-1,2,3,4-tetrahydronaphthalene-1,2- Dicarboxylic dianhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-7methyl-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic dianhydride, norbornane-2- Spiro-2'-cyclopentanone-5'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spir
  • the molar ratio of the structures represented by the general formulas (1) and (2) in the present invention is obtained by a method of calculating from the molar ratio of the monomers used for polymerization or by using a nuclear magnetic resonance spectrometer (NMR). It can be confirmed by a method for detecting peaks of a polyamide structure, an imide precursor structure, or an imide structure in a resin, a resin composition, or a cured film.
  • NMR nuclear magnetic resonance spectrometer
  • the component (A) having a carboxylic acid residue at the molecular chain end is, for example, in the case of a polyimide having a carboxylic acid residue at the molecular chain end, an acid anhydride content greater than that of the diamine used for polymerization.
  • a specific compound from compounds generally used as a terminal blocking agent specifically , an acid anhydride, a monocarboxylic acid, a monoacid chloride compound, or a monoactive ester compound.
  • component (A) By blocking the molecular chain ends of component (A) with a carboxylic acid or acid anhydride terminal blocker having a hydroxyl group, a carboxyl group, a sulfonic acid group, a thiol group, a vinyl group, an ethynyl group, or an allyl group,
  • a carboxylic acid or acid anhydride terminal blocker having a hydroxyl group, a carboxyl group, a sulfonic acid group, a thiol group, a vinyl group, an ethynyl group, or an allyl group.
  • the rate of dissolution of component (A) in an alkaline aqueous solution and the mechanical properties of the resulting cured film can be easily adjusted within a preferred range.
  • a plurality of terminal blocking agents may be reacted to introduce a plurality of different terminal groups.
  • Acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds suitable as terminal blocking agents include phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride, and 3-hydroxyphthalic acid.
  • Acid anhydrides such as acid anhydride, 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1 -hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, 4-carboxybenzenesulfonic acid, etc.
  • Polymer compounds into which these terminal blocking agents are introduced become component (A) with a structure in which the molecular chain ends are derived from carboxylic acid residues.
  • a terminal blocking agent that can be used to obtain the component (A) whose molecular chain terminal is a structure derived from a carboxylic acid residue can be easily detected by the following method.
  • the component (A) into which a terminal blocking agent has been introduced is dissolved in an acidic solution, decomposed into the amine component and the acid anhydride component, which are structural units, and analyzed by gas chromatography (GC) or NMR.
  • GC gas chromatography
  • the terminal blocking agent used in the present invention can be easily detected. Apart from this, it can be easily detected by directly measuring the resin component into which the end blocking agent has been introduced by pyrolysis gas chromatography (PGC), infrared spectrum and 13C-NMR spectrum.
  • PPC pyrolysis gas chromatography
  • component (A) is synthesized, for example, by the following method, but is not limited to this.
  • the polyimide structure is formed by replacing part of the diamine with a primary monoamine as a terminal blocker, or by replacing tetracarboxylic dianhydride with a dicarboxylic anhydride as a terminal blocker by a known method. synthesized.
  • a method of reacting a tetracarboxylic dianhydride, a diamine compound and a monoamine at a low temperature a method of reacting a tetracarboxylic dianhydride, a dicarboxylic anhydride and a diamine compound at a low temperature, and a method of reacting a tetracarboxylic dianhydride with a diamine compound.
  • a polyimide precursor is obtained by using a method such as a method of obtaining a diester with an alcohol, and then reacting a diamine, a monoamine, and a condensing agent. After that, a polyimide can be synthesized using a known imidization reaction method.
  • the component (A) is polymerized by the above method, then poured into a large amount of water or a mixture of methanol and water, etc., precipitated, separated by filtration and dried, and isolated.
  • the drying temperature is preferably 40-100°C, more preferably 50-80°C.
  • the imidization rate of the polyimide suitably used as a component can be easily calculated
  • the polymer was heat-treated at 350 ° C. for 1 hour , and the infrared absorption spectrum was measured as a sample with an imidization rate of 100%.
  • the imidization ratio is determined by calculating the content of imide groups in the pre-resin.
  • the imidization rate is preferably 50% or more, more preferably 80% or more, in order to suppress the change in the ring closure rate during thermosetting and obtain the effect of reducing stress.
  • the resin composition of the present invention contains a cationic polymerizable compound as the (B) component.
  • Component (B) is preferably an epoxy compound or an oxetane compound.
  • Preferred examples include cyclic ether compounds such as epoxy compounds and oxetane compounds, ethylenically unsaturated compounds such as vinyl ethers and styrenes, bicycloorthoesters, spiroorthocarbonates, and spiroorthoesters.
  • epoxy compound known ones can be used, including aromatic epoxy compounds, alicyclic epoxy compounds and aliphatic epoxy compounds.
  • aromatic epoxy compounds include glycidyl ethers of monohydric or polyhydric phenols (phenol, bisphenol A, phenol novolak, and alkylene oxide adducts thereof) having at least one aromatic ring.
  • Examples of alicyclic epoxy compounds include compounds obtained by epoxidizing a compound having at least one cyclohexene or cyclopentene ring with an oxidizing agent (3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, etc. ).
  • Aliphatic epoxy compounds include aliphatic polyhydric alcohols or polyglycidyl ethers of alkylene oxide adducts thereof (1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, etc.), aliphatic polybasic acids polyglycidyl esters (diglycidyl tetrahydrophthalate, etc.), and epoxidized long-chain unsaturated compounds (epoxidized soybean oil, epoxidized polybutadiene, etc.).
  • oxetane compound known ones can be used. -oxetanylmethyl)ether, 2-hydroxypropyl(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, oxetanylsilsesquioxetane and phenol novolac oxetane etc.
  • known cationic polymerizable monomers can be used, including aliphatic monovinyl ethers, aromatic monovinyl ethers, polyfunctional vinyl ethers, styrene and cationic polymerizable nitrogen-containing monomers.
  • the aliphatic monovinyl ethers include methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether and cyclohexyl vinyl ether.
  • Aromatic monovinyl ethers include 2-phenoxyethyl vinyl ether, phenyl vinyl ether and p-methoxyphenyl vinyl ether.
  • polyfunctional vinyl ethers examples include butanediol-1,4-divinyl ether and triethylene glycol divinyl ether.
  • Styrenes include styrene, ⁇ -methylstyrene, p-methoxystyrene and ptert-butoxystyrene.
  • Examples of cationic polymerizable nitrogen-containing monomers include N-vinylcarbazole and N-vinylpyrrolidone.
  • Bicycloorthoesters include 1-phenyl-4-ethyl-2,6,7-trioxabicyclo[2.2.2]octane and 1-ethyl-4-hydroxymethyl-2,6,7-trioxabicyclo - [2.2.2] octane and the like.
  • spiro orthocarbonates examples include 1,5,7,11-tetraoxaspiro[5.5]undecane and 3,9-dibenzyl-1,5,7,11-tetraoxaspiro[5.5]undecane. be done.
  • Spiro orthoesters include 1,4,6-trioxaspiro[4.4]nonane, 2-methyl-1,4,6-trioxaspiro[4.4]nonane and 1,4,6-trioxas pyro[4.5]decane and the like.
  • epoxy compounds oxetane compounds and vinyl ethers are preferred, epoxy compounds and oxetane compounds are more preferred, and epoxy compounds are particularly preferred.
  • the component (B) may be used alone or in combination of two or more.
  • the content of component (B) is preferably 30 parts by mass or more from the viewpoint of exhibiting sufficient cationic curability and improving pattern processability when the total of components (A) is 100 parts by mass. More preferably, it is 50 parts by mass or more. On the other hand, from the viewpoint of improving resolution, it is preferably 200 parts by mass or less, more preferably 150 parts by mass or less.
  • the resin composition of the present invention contains a cationic polymerization initiator as the (C) component.
  • the cationic polymerization initiator is one that directly or indirectly generates an acid by light or heating to cause cationic polymerization.
  • known compounds can be used without particular limitation.
  • Specific examples of cationic polymerization initiators include aromatic iodonium complex salts and aromatic sulfonium complex salts.
  • aromatic iodonium complex salts include diphenyliodonium tetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, di(4-nonylphenyl)iodonium hexafluorophosphate, and the like.
  • These (C) components may be used alone or in combination of two or more.
  • the resin composition of the present invention is preferably a negative photosensitive resin composition.
  • component (C) is preferably a photocationic polymerization initiator.
  • a photocationic polymerization initiator By selecting a photocationic polymerization initiator as the component (C), it is possible to add a contrast between the progress of cationic polymerization in the light-irradiated part and the light-unirradiated part in the resin composition, and the resin composition can be developed with any developer.
  • dissolving it is preferable from the point that negative pattern formation is possible, and it is preferable as a negative photosensitive resin composition.
  • the resin composition of the present invention contains a silane coupling agent as the (D) component. It is important that component (D) has a carboxyl group and/or an acid anhydride group.
  • the silane coupling agent refers to a silane compound having two or more functional groups.
  • the (D) component having a carboxyl group and/or an acid anhydride group can improve adhesion to an inorganic substrate. Furthermore, by trapping a compound that inhibits cationic polymerization such as amines, which may be present in a very small amount in the resin composition, the carboxyl group or acid anhydride group improves the reactivity of cationic polymerization, and during patterning.
  • silane coupling agent having a carboxyl group examples include X-12-1135 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • silane coupling agent having an acid anhydride group examples include KBM-967TR-1 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • component (D) preferably has the structure of general formula (3).
  • n is an integer of 1 or more, and X is an organic group.
  • n is an integer of 1 or more, and more preferably an integer of 1 to 6.
  • X is not particularly limited as long as it is an organic group, it is more preferably an organic group having 1 to 6 carbon atoms.
  • X satisfying formula (3) include methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, n-hexyl, cyclohexyl, and phenyl groups. is preferably a methyl group or an ethyl group.
  • the component (D) has the structure of the general formula (3)
  • the sensitivity during patterning is further improved.
  • Specific examples of the silane coupling agent having the structure of general formula (3) include KBM-967TR-1 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • the resin composition of the present invention has a silane coupling agent having a carboxyl group and/or an acid anhydride group as the component (D), the silane coupling agent having a functional group other than the carboxyl group and the acid anhydride group A ring agent may be included.
  • silane coupling agents having functional groups other than carboxyl groups and acid anhydride groups include N-phenylaminoethyltrimethoxysilane, N-phenylaminoethyltriethoxysilane, N-phenylaminopropyltrimethoxysilane, N-phenylaminopropyltriethoxysilane, N-phenylaminobutyltrimethoxysilane, N-phenylaminobutyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris( ⁇ -methoxyethoxy)silane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane
  • the total amount of component (D) is preferably 1 to 10% by mass, more preferably 2 to 5% by mass. If the total amount of component (D) is less than the preferred range, adhesion will be reduced, and if it exceeds the preferred range, development residue will tend to occur.
  • the resin composition of the present invention may contain a sensitizer to absorb ultraviolet rays and provide the absorbed light energy to the photoacid generator.
  • a sensitizer for example, an anthracene compound having alkoxy groups at the 9- and 10-positions (9,10-dialkoxy-anthracene derivative) is preferable.
  • alkoxy groups include C1-C4 alkoxy groups such as methoxy, ethoxy and propoxy groups.
  • the 9,10-dialkoxy-anthracene derivative may further have a substituent.
  • substituents include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, C1 to C4 alkyl groups such as a methyl group, an ethyl group and a propyl group, a sulfonic acid alkyl ester group, and a carboxylic acid alkyl ester group. etc.
  • substituents include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, C1 to C4 alkyl groups such as a methyl group, an ethyl group and a propyl group, a sulfonic acid alkyl ester group, and a carboxylic acid alkyl ester group. etc.
  • alkyl in the sulfonic acid alkyl ester group and carboxylic acid alkyl ester include C1-C4 alkyl such as methyl
  • the resin composition of the present invention may contain a thermal cross-linking agent, and although the thermal cross-linking agent at that time is not particularly limited, a compound having an alkoxymethyl group or a methylol group is preferable.
  • Examples having an alkoxymethyl group or a methylol group include, for example, DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DML-BisOC-P, DMO-PC, DMO-PTBP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, HML-TPPHBA, HML
  • the resin composition of the present invention may optionally contain surfactants, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, alcohols such as ethanol, cyclohexanone and methyl for the purpose of improving the wettability with the substrate.
  • esters such as ethyl lactate and propylene glycol monomethyl ether acetate
  • alcohols such as ethanol, cyclohexanone and methyl
  • Ketones such as isobutyl ketone and ethers such as tetrahydrofuran and dioxane may be included.
  • inorganic particles such as silicon dioxide or titanium dioxide, polyimide powder, or the like may be contained.
  • the shape of the resin composition of the present invention before curing is not limited, and examples thereof include a varnish shape and a film shape.
  • the resin composition of the present invention in the form of a varnish is referred to as a resin composition varnish
  • the resin composition of the present invention in the form of a film is referred to as the resin composition film of the present invention.
  • the resin composition film of the present invention may be in the form of a film formed on a support, or may be in the form of no support.
  • the resin composition of the present invention is used in the form of a varnish, the components (A) to (D) and optional components dissolved in an organic solvent can be used.
  • the resin composition film of the present invention can be obtained, for example, by coating the resin composition of the present invention on a support and then drying it if necessary.
  • the resin composition film of the present invention is obtained by applying a solution (varnish) of the resin composition of the present invention onto a support and then drying it if necessary.
  • a resin composition varnish is obtained by adding an organic solvent to a resin composition. Any organic solvent that dissolves the resin composition may be used as the organic solvent.
  • organic solvents include ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and ethylene glycol dibutyl ether, Acetates such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate and butyl lactate , acetone, methyl ethyl ketone, acetylacetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, cyclopentanone, ketones such as 2-heptan
  • the resin composition varnish may be filtered using filter paper or a filter.
  • the filtration method is not particularly limited, but a method of filtration by pressure filtration using a filter having a retained particle size of 0.4 ⁇ m to 10 ⁇ m is preferred.
  • the resin composition film of the present invention is preferably used after being formed on a support.
  • the support is not particularly limited, but various commercially available films such as polyethylene terephthalate (sometimes called PET) film, polyphenylene sulfide film, and polyimide film can be used.
  • the bonding surface between the support and the resin composition film may be surface-treated with silicone, a silane coupling agent, an aluminum chelating agent, polyurea, or the like in order to improve adhesion and releasability.
  • the thickness of the support is not particularly limited, but from the viewpoint of workability, it is preferably in the range of 10 to 100 ⁇ m.
  • the resin composition film of the present invention may have a protective film on the film in order to protect the surface. Thereby, the surface of the resin composition film can be protected from contaminants such as dirt and dust in the air.
  • protective films include polyolefin films and polyester films.
  • the protective film preferably has a small adhesive force to the resin composition film.
  • Methods for applying the resin composition varnish to the support include spin coating using a spinner, spray coating, roll coating, screen printing, blade coater, die coater, calendar coater, meniscus coater, bar coater, roll coater, and comma roll coater. , gravure coater, screen coater, slit die coater and the like.
  • the coating film thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, etc., it is generally preferable that the film thickness after drying is 0.5 ⁇ m or more and 100 ⁇ m or less.
  • Ovens, hot plates, infrared rays, etc. can be used for drying.
  • the drying temperature and drying time may be within a range in which the organic solvent can be volatilized, and it is preferable to appropriately set a range such that the resin composition film is in an uncured or semi-cured state. Specifically, it is preferable to carry out at a temperature in the range of 40° C. to 120° C. for 1 minute to several tens of minutes. Further, these temperatures may be combined and the temperature may be raised stepwise, for example, heat treatment may be performed at 70° C., 80° C., and 90° C. for 1 minute each.
  • the varnish is first applied onto the substrate.
  • coating methods include spin coating using a spinner, spray coating, roll coating, and screen printing.
  • the coating film thickness varies depending on the coating method, the solid content concentration and viscosity of the resin composition, etc., but it is usually preferable to apply the coating so that the film thickness after drying is 0.5 ⁇ m or more and 100 ⁇ m or less.
  • the substrate coated with the resin composition varnish is dried to obtain a resin composition film. Ovens, hot plates, infrared rays, etc. can be used for drying.
  • the drying temperature and drying time may be within a range in which the organic solvent can be volatilized, and it is preferable to appropriately set a range such that the resin composition film is in an uncured or semi-cured state. Specifically, it is preferable to carry out at a temperature in the range of 50 to 150° C. for 1 minute to several hours.
  • a resin composition film when used, if it has a protective film, it is peeled off, and the resin composition film and the substrate are opposed to each other and bonded together by thermocompression to obtain a resin composition coating.
  • Thermocompression bonding can be performed by heat press treatment, heat lamination treatment, heat vacuum lamination treatment, or the like.
  • the bonding temperature is preferably 40° C. or higher from the viewpoint of adhesion to the substrate and embedding.
  • the bonding temperature is preferably 150° C. or less in order to prevent the resin composition film from hardening during bonding and the resolution of pattern formation in the exposure and development steps from deteriorating.
  • the substrates to be used include silicon wafers, ceramics, gallium arsenide, organic circuit substrates, inorganic circuit substrates, and circuit-constituting materials arranged on these substrates. It is not limited to these.
  • organic circuit boards include glass-based copper-clad laminates such as glass cloth and epoxy copper-clad laminates, composite copper-clad laminates such as glass nonwoven fabrics and epoxy copper-clad laminates, polyetherimide resin substrates, and polyetherimide resin substrates.
  • heat-resistant/thermoplastic substrates such as etherketone resin substrates and polysulfone resin substrates, and flexible substrates such as polyester copper-clad film substrates and polyimide copper-clad film substrates.
  • inorganic circuit substrates include ceramic substrates such as alumina substrates, aluminum nitride substrates and silicon carbide substrates, and metal substrates such as aluminum base substrates and iron base substrates.
  • circuit constituent materials include conductors containing metals such as silver, gold, and copper; resistors containing inorganic oxides; low dielectric materials containing glass materials and/or resins; Examples include high dielectric materials containing dielectric inorganic particles and the like, and insulators containing glass-based materials and the like.
  • the resin composition film formed by the above method is exposed to actinic rays through a mask having a desired pattern.
  • Actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays, etc.
  • the exposure may be performed without peeling the support from the resin composition film.
  • these alkaline aqueous solutions are added with a polar solvent such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone may be contained alone or in combination. good.
  • a polar solvent such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, esters such as ethyl
  • Development can be carried out by a method such as spraying the above developer onto the film surface, heaping the developer onto the film surface, immersing in the developer, or immersing and applying ultrasonic waves.
  • Developing conditions such as the developing time and the temperature of the developer in the developing step may be any conditions as long as the exposed portion can be removed and the pattern can be formed.
  • alcohols such as ethanol and isopropyl alcohol
  • esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to water for rinsing.
  • baking may be performed before development. This may improve the resolution of the pattern after development and increase the allowable range of development conditions.
  • the baking temperature is preferably in the range of 50 to 180°C, more preferably in the range of 60 to 120°C.
  • the time is preferably 5 seconds to several hours.
  • unreacted cationic polymerizable compounds and cationic polymerization initiators remain in the resin composition film. For this reason, they may be thermally decomposed to generate gas during thermocompression bonding or curing. In order to avoid this, it is preferable to irradiate the entire surface of the resin composition film after pattern formation with the above-described exposure light to generate acid from the cationic polymerization initiator. By doing so, the reaction of the unreacted cationic polymerizable compound proceeds during thermocompression bonding or curing, and generation of gas due to thermal decomposition can be suppressed.
  • a temperature of 150°C to 500°C is applied to advance the thermal cross-linking reaction.
  • Crosslinking can improve heat resistance and chemical resistance.
  • a method for this heat treatment a method of selecting a temperature and increasing the temperature stepwise, or a method of selecting a certain temperature range and continuously increasing the temperature for 5 minutes to 5 hours can be selected.
  • the former there is a method of heat-treating at 130° C. and 200° C. for 30 minutes each.
  • An example of the latter is a method of linearly raising the temperature from room temperature to 400° C. over 2 hours.
  • the cured film of the present invention obtained by curing the resin composition of the present invention or the resin composition film of the present invention can be used for electronic parts such as semiconductor devices. That is, the semiconductor device of the present invention has the cured film of the present invention.
  • the semiconductor device in the present invention refers to all devices that can function by utilizing the characteristics of semiconductor elements.
  • An electro-optical device in which a semiconductor element is connected to a substrate, a semiconductor circuit board, a stack of a plurality of semiconductor elements, and an electronic device including these are all included in the semiconductor device.
  • Semiconductor devices also include electronic parts such as multilayer wiring boards for connecting semiconductor elements.
  • semiconductor passivation films surface protective films of semiconductor elements, interlayer insulating films between semiconductor elements and wiring, interlayer insulating films between a plurality of semiconductor elements, and interlayer insulation between wiring layers in multi-layer wiring for high-density mounting.
  • semiconductor passivation films surface protective films of semiconductor elements
  • interlayer insulating films between semiconductor elements and wiring interlayer insulating films between a plurality of semiconductor elements
  • interlayer insulation between wiring layers in multi-layer wiring for high-density mounting.
  • it is suitably used for applications such as insulating films and insulating layers of organic electroluminescence elements, it is not limited to this and can be used for various applications.
  • a mask having a pattern with a via size of 20 ⁇ m ⁇ is set in the exposure device, and an ultra-high pressure mercury lamp is used under the condition of an exposure gap of 100 ⁇ m between the mask and the resin composition film. Then, exposure was performed with an exposure amount of 100 to 1000 mJ/cm 2 (i-line conversion, full wavelength exposure). After exposure, post-exposure heating was performed on a hot plate at 80° C. for 10 minutes. After that, by dip development, the unexposed portion was removed using a 2.38% by mass aqueous solution of tetramethylammonium hydroxide, and rinsed with water.
  • the development time was twice the time required for the unexposed areas to completely dissolve.
  • the pattern thus obtained was observed with an optical microscope to confirm whether there was any abnormality such as clogging in the pattern. Further, the remaining film ratio was calculated from the film thickness of the obtained pattern before development and the film thickness after development. The obtained residual film ratio was rounded off to the first decimal place. The minimum exposure dose at which the pattern was not clogged and the residual film rate was 90% or more was determined, and the sensitivity during pattern processing was evaluated in five stages from A++ to C as follows.
  • a resin composition film was formed on a silicon wafer in the same manner as in the pattern processability evaluation method. If there was a support film, it was peeled off and then exposed to light with an exposure amount of 500 mJ/cm 2 (i-line conversion, full wavelength exposure) using an ultra-high pressure mercury lamp. After exposure, post-exposure heating was performed on a hot plate at 80° C. for 10 minutes. Then, using an inert oven (INL-60, manufactured by Koyo Thermo Systems Co., Ltd.), the temperature was raised from room temperature to 200 ° C. over 60 minutes in an N 2 atmosphere (oxygen concentration 20 ppm or less), and then 60 at 200 ° C.
  • an inert oven INL-60, manufactured by Koyo Thermo Systems Co., Ltd.
  • Synthesis Example 1 Synthesis of hydroxyl group-containing diamine compound (a) 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (hereinafter referred to as BAHF) (18.3 g, 0.05 mol) was added to 100 mL of acetone. , propylene oxide (17.4 g, 0.3 mol) and cooled to -15°C. A solution of 3-nitrobenzoyl chloride (20.4 g, 0.11 mol) dissolved in 100 mL of acetone was added dropwise thereto. After completion of the dropwise addition, the mixture was allowed to react at -15°C for 4 hours, and then returned to room temperature. The precipitated white solid was separated by filtration and vacuum dried at 50°C.
  • BAHF 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane
  • Synthesis Example 2 Synthesis of Polyimide (A-2) Under a dry nitrogen stream, BAHF (36.63 g, 0.10 mol) was added to 80 g of ⁇ -butyrolactone (hereinafter referred to as GBL), and stirred and dissolved at 120°C. Next, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione (hereinafter referred to as TDA ⁇ 100) (24.02 g, 0.08 mol) was added together with 20 g of GBL and stirred at 120° C. for 1 hour and then at 200° C.
  • TDA ⁇ 100 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione
  • reaction solution was poured into 3 L of water to collect a white precipitate. This precipitate was collected by filtration, washed with water three times, and dried in a vacuum dryer at 80° C. for 5 hours to obtain a polyimide having a structure in which the molecular chain ends are derived from amino residues.
  • Synthesis Example 2 Synthesis of polyamide (A-3) BAHF (29.30 g, 0.08 mol) was added to 100 g of N-methyl-2-pyrrolidone (hereinafter referred to as NMP) under a dry nitrogen stream, and stirred at room temperature. Dissolved. Thereafter, 4,4′-diphenyletherdicarboxylic acid dichloride (29.52, 0.1 mol) was added little by little while maintaining the temperature of the reaction solution at ⁇ 10 to 0° C. After completion of the addition, the temperature was raised to room temperature, Stirring was continued for 3 hours. Next, the reaction solution was poured into 3 L of water to collect a white precipitate. This precipitate was collected by filtration, washed with water three times, and dried in a vacuum dryer at 80° C. for 5 hours to obtain a polyamide having a structure in which the molecular chain ends were derived from carboxylic acid residues.
  • NMP N-methyl-2-pyrrolidone
  • Synthesis Example 4 Synthesis of Polyamideimide (A-5) Under a dry nitrogen stream, a hydroxyl group-containing diamine compound (a) (31.43 g, 0.08 mol) was added to 80 g of GBL and stirred at 120°C. Next, TDA-100 (30.03 g, 0.1 mol) was added together with 20 g of GBL and stirred at 120° C. for 1 hour and then at 200° C. for 4 hours to obtain a reaction solution. Next, the reaction solution was poured into 3 L of water to collect a white precipitate. This precipitate was collected by filtration, washed with water three times, and dried in a vacuum dryer at 80° C. for 5 hours to obtain a polyamideimide having a structure in which the molecular chain ends were derived from carboxylic acid residues.
  • Example 1 10 g of GPH-103 (trade name, manufactured by Nippon Kayaku Co., Ltd.) as component (A), 12.5 g of TEPIC-VL (trade name, manufactured by Nissan Chemical Industries, Ltd.) as component (B), and (C) as component 1 g of CPI-310FG (trade name, manufactured by San-Apro Co., Ltd.) and 1 g of X-12-1135 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) as component (D) were dissolved in GBL. The amount of the solvent added was adjusted so that the solid content concentration was 60% by mass, with the additives other than the solvent being the solid content. Thereafter, pressure filtration was performed using a filter having a retained particle size of 1 ⁇ m to obtain a resin composition varnish.
  • GPH-103 trade name, manufactured by Nippon Kayaku Co., Ltd.
  • TEPIC-VL trade name, manufactured by Nissan Chemical Industries, Ltd.
  • C component 1 g of CPI-310FG
  • A Polymer compound A-1: GPH-103 (alkali-soluble biphenylaralkyl-type phenol compound, manufactured by Nippon Kayaku Co., Ltd.)
  • A-5 Polyimide having a carboxylic acid residue at the molecular chain end Polyamidoimide of acid residues.
  • B-1 Cationic polymerizable compound B-1: TEPIC-VL (epoxy compound, manufactured by Nissan Chemical Industries, Ltd.)
  • B-2 OXT-221 (oxetane compound, manufactured by Toagosei Co., Ltd.).
  • C Cationic polymerization initiator C-1: CPI-310FG (sulfonium salt-based photoacid generator, manufactured by San-Apro Co., Ltd.).
  • Silane coupling agent D-1 X-12-1135 (silane coupling agent having a carboxyl group, manufactured by Nissan Chemical Industries, Ltd.)
  • D-4: KBM-903 silane coupling agent having an amino group, manufactured by Shin-Etsu Chemical Co., Ltd.).
  • the above resin composition varnish was applied onto a 50 ⁇ m thick PET film using a comma roll coater, dried at 120° C. for 8 minutes, and then laminated with a 10 ⁇ m thick polypropylene film as a protective film. , to obtain a resin composition film.
  • the thickness of the resin composition film was adjusted to 20 ⁇ m.
  • sensitivity and adhesion during patterning were evaluated as described above. Table 2 shows the results.
  • the present invention it is possible to provide a resin composition, a resin composition film, a cured film, and a semiconductor device using these, which exhibit sufficient adhesion to inorganic substrates and sensitivity during patterning. It is possible.

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Abstract

L'invention concerne : une composition de résine ayant une excellente sensibilité pendant un traitement de motif et ayant une excellente adhérence à des matériaux inorganiques ; un film de composition de résine ; et un dispositif à semi-conducteur l'utilisant. La composition de résine contient un composé polymère en tant que composant (A), un composé polymérisable cationique en tant que composant (B), un amorceur de polymérisation cationique en tant que composant (C), et un agent de couplage au silane en tant que composant (D), la composition de résine étant caractérisée en ce que le composant (D) a un groupe carboxyle et/ou un groupe anhydride d'acide.
PCT/JP2022/026925 2021-08-30 2022-07-07 Composition de résine, film de composition de résine, film durci et dispositif à semi-conducteur WO2023032467A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020101650A (ja) * 2018-12-21 2020-07-02 住友ベークライト株式会社 ネガ型感光性樹脂組成物、それを用いた半導体装置および電子機器
JP2021047378A (ja) * 2019-09-20 2021-03-25 住友ベークライト株式会社 感光性樹脂組成物、電子デバイスの製造方法および電子デバイス
JP2021055055A (ja) * 2019-09-24 2021-04-08 東レ株式会社 樹脂組成物、樹脂組成物フィルム、硬化膜、およびこれらを用いた半導体装置
JP2021076728A (ja) * 2019-11-11 2021-05-20 住友ベークライト株式会社 感光性樹脂組成物、電子デバイスの製造方法および電子デバイス

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020101650A (ja) * 2018-12-21 2020-07-02 住友ベークライト株式会社 ネガ型感光性樹脂組成物、それを用いた半導体装置および電子機器
JP2021047378A (ja) * 2019-09-20 2021-03-25 住友ベークライト株式会社 感光性樹脂組成物、電子デバイスの製造方法および電子デバイス
JP2021055055A (ja) * 2019-09-24 2021-04-08 東レ株式会社 樹脂組成物、樹脂組成物フィルム、硬化膜、およびこれらを用いた半導体装置
JP2021076728A (ja) * 2019-11-11 2021-05-20 住友ベークライト株式会社 感光性樹脂組成物、電子デバイスの製造方法および電子デバイス

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