WO2025142647A1 - 感光性樹脂組成物、硬化物および半導体装置 - Google Patents

感光性樹脂組成物、硬化物および半導体装置 Download PDF

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Publication number
WO2025142647A1
WO2025142647A1 PCT/JP2024/044654 JP2024044654W WO2025142647A1 WO 2025142647 A1 WO2025142647 A1 WO 2025142647A1 JP 2024044654 W JP2024044654 W JP 2024044654W WO 2025142647 A1 WO2025142647 A1 WO 2025142647A1
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mass
parts
resin composition
photosensitive resin
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English (en)
French (fr)
Japanese (ja)
Inventor
律也 川崎
誠 堀井
一史 佐藤
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Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Priority to JP2025529781A priority Critical patent/JP7786648B2/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029

Definitions

  • the present invention relates to a photosensitive resin composition, a cured product, and a semiconductor device.
  • Polyimides are used, for example, as protective materials in liquid crystal display elements and semiconductors, insulating materials, and thin films for electronic materials such as color filters.
  • Patent Document 1 discloses a resin composition that contains (A) a polyimide resin, characterized in that the polyimide resin (A) has an organic group with a specific structure, for the purpose of providing a resin composition that is easily soluble in an alkaline developer before exposure and becomes insoluble in an alkaline developer upon exposure, and that has little film shrinkage upon curing and can produce a highly rectangular pattern after curing.
  • the present invention provides a photosensitive resin composition and a cured product that can improve the reliability of the resulting semiconductor device, as well as a semiconductor device with improved reliability.
  • the tensile modulus of the photosensitive resin composition of this embodiment is preferably 1.0 GPa or more, more preferably 1.5 GPa or more, even more preferably 2.0 GPa or more, and even more preferably 2.3 GPa or more.
  • the upper limit of the tensile modulus of the photosensitive resin composition of this embodiment is not particularly limited, but may be, for example, 5.0 GPa or less, or 4.0 GPa or less.
  • the tensile modulus of elasticity of the photosensitive resin composition of the present embodiment can be measured, for example, by the following method.
  • the photosensitive resin composition is spin-coated on the surface of a silicon wafer so that the film thickness after drying is 10 ⁇ m, and the wafer is pre-baked at 110° C. for 3 minutes, exposed to 600 mJ/cm 2 with a high-pressure mercury lamp, and then post-baked at 230° C. for 3 hours in a nitrogen atmosphere to produce a cured product having a thickness of 100 mm ⁇ 100 mm ⁇ 10 ⁇ m.
  • the tensile modulus of the cured product is measured at 23° C. and a stretching speed of 5 mm/min using a tensile tester in accordance with JIS K 7161:2014.
  • the storage modulus of the photosensitive resin composition of this embodiment is preferably 1.0 GPa or more, more preferably 2.0 GPa or more, even more preferably 2.5 GPa or more, and even more preferably 3.0 GPa or more.
  • the upper limit of the storage modulus of the photosensitive resin composition of this embodiment is not particularly limited, and may be, for example, 6.0 GPa or less, or 5.0 GPa or less.
  • the storage modulus of the photosensitive resin composition of this embodiment is preferably 1.0 GPa or more and 6.0 GPa or less, more preferably 2.0 GPa or more and 6.0 GPa or less, even more preferably 2.5 GPa or more and 5.0 GPa or less, and even more preferably 3.0 GPa or more and 5.0 GPa or less.
  • the storage modulus of the photosensitive resin composition of the present embodiment can be measured, for example, by the following method. First, a photosensitive resin composition is spin-coated onto a silicon wafer surface so that the film thickness after drying is 10 ⁇ m, and the wafer is pre-baked at 110° C. for 3 minutes, exposed to 600 mJ/cm 2 from a high-pressure mercury lamp, and then post-baked for 3 hours at 230° C. in a nitrogen atmosphere to produce a cured product of 100 mm ⁇ 100 mm ⁇ 10 ⁇ m in thickness. Next, the storage modulus of the cured product at 30° C. is measured by dynamic mechanical analysis (DMA).
  • DMA dynamic mechanical analysis
  • the polyimide (A) of this embodiment has a double bond in the side chain.
  • the double bond in the polyimide (A) preferably contains a carbon-carbon double bond, and more preferably contains a polymerizable carbon-carbon double bond.
  • the polyimide (A) of the present embodiment preferably contains a constitutional unit represented by the following general formula (1) from the viewpoint of further improving the performance balance of patterning ability, copper adhesion, mechanical strength, and reliability of the obtained semiconductor device.
  • Y represents a divalent organic group, and from the viewpoint of further improving the performance balance of patterning ability, copper adhesion, mechanical strength, and reliability of the obtained semiconductor device, Y is preferably a divalent group containing an alkylene group or a divalent group containing at least one aromatic ring.
  • the alkylene group is preferably an alkylene group having 1 to 5 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms.
  • the aromatic ring is preferably a divalent benzene ring, a divalent naphthalene ring, a divalent anthracene ring, or a divalent biphenyl group, more preferably a divalent benzene ring or a divalent biphenyl group.
  • Y is preferably selected from the group consisting of a group represented by the following general formula (1a), a group represented by the following general formula (1b), and a group represented by the following general formula (1c), from the viewpoint of further improving the balance of performance among patterning properties, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device, and is more preferably a group represented by the following general formula (1b).
  • R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and a plurality of R 1s and a plurality of R 2s may be the same or different,
  • R 3 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and a plurality of R 3s may be the same or different, and * represents a bond.
  • R 4 and R 5 each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and a plurality of R 4s and a plurality of R 5s may be the same or different, and * represents a bond.
  • Z represents an alkylene group having 1 to 5 carbon atoms or a divalent aromatic group, and * represents a bond.
  • R 1 and R 2 are preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and further preferably a hydrogen atom or a methyl group.
  • R 1 and R 2 are each independently a hydrogen atom, more preferably 0 to 2 of R 1 and R 2 are each a hydrogen atom, and further preferably 1 of R 1 and R 2 is a hydrogen atom.
  • R3 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, even more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.
  • R 4 and R 5 are preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and further preferably a hydrogen atom or a methyl group.
  • R 4 and R 5 are each independently a hydrogen atom, more preferably 0 to 2 of R 4 and R 5 are each a hydrogen atom, and further preferably 1 of R 4 and R 5 is a hydrogen atom.
  • the polyimide (A) of this embodiment preferably contains a structural unit represented by the following general formula (2) from the viewpoint of further improving the balance of performance among patterning properties, copper adhesion, mechanical strength, and the reliability of the resulting semiconductor device.
  • m1 and m2 are preferably 0 to 2, and more preferably 0 or 1, from the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and reliability of the obtained semiconductor device.
  • Q is preferably a hydroxy group or an alkyl group having 1 to 2 carbon atoms
  • Q is preferably a divalent organic group having 1 to 5 carbon atoms, more preferably a divalent organic group having 1 to 5 carbon atoms and containing a urethane bond, and even more preferably a divalent organic group having 2 to 4 carbon atoms and containing a urethane bond.
  • the polyimide (A) of this embodiment preferably contains a structural unit (a) represented by the following general formula (3), from the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and the reliability of the resulting semiconductor device.
  • the structural unit (a) of this embodiment preferably contains a structural unit (a p ) represented by general formula (3) in which at least one of m1 and m2 is 1 or more, and a structural unit (a q ) represented by general formula (3) in which both m1 and m2 are 0.
  • the content of the structural unit (a p ) in the polyimide (A) of the present embodiment is preferably 30 mol % or more, more preferably 35 mol % or more, even more preferably 40 mol % or more, even more preferably 45 mol % or more, even more preferably 50 mol % or more, even more preferably 60 mol % or more, even more preferably 70 mol % or more, even more preferably 80 mol % or more, even more preferably 90 mol % or more, and is preferably 100 mol % or less, more preferably 99 mol % or less, and even more preferably 95 mol % or less.
  • the content of the structural unit (a p ) in the polyimide (A) of the present embodiment is, when the total content of the structural unit (a p ) and the structural unit (a q ) is taken as 100 mol %, preferably 30 mol % or more and 100 mol % or less, more preferably 35 mol % or more and 100 mol % or less, even more preferably 40 mol % or more and 100 mol % or less, even more preferably 45 mol % or more and 100 mol % or less, even more preferably 50 mol % or more and 100 mol % or less, even more preferably 60 mol % or more and 100 mol % or less, even more preferably 70 mol % or more and 100 mol % or less, even more preferably 80 mol % or more and 100 mol % or less, even more preferably 80 mol
  • the imidization rate represented by ⁇ IM/(IM+AM) ⁇ 100(%) is preferably 90% or more, more preferably 95% or more, and even more preferably 98% or more, from the viewpoint of further improving the reliability of the obtained semiconductor device.
  • the upper limit of the imidization rate of the polyimide (A) of this embodiment is not particularly limited, but may be, for example, 100% or less.
  • the imidization rate of the polyimide (A) of the present embodiment is preferably 90% or more and 100% or less, more preferably 95% or more and 100% or less, and even more preferably 98% or more and 100% or less.
  • the content of polyimide (A) in the photosensitive resin composition of the present embodiment is, when the total amount of the solid contents in the photosensitive resin composition is taken as 100 parts by mass, preferably 30 parts by mass or more, more preferably 40 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, even more preferably 60 parts by mass or more, and is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, even more preferably 85 parts by mass or less, even more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less.
  • the content of polyimide (A) in the photosensitive resin composition of this embodiment is preferably 30 parts by mass or more and 95 parts by mass or less, more preferably 40 parts by mass or more and 90 parts by mass or less, even more preferably 50 parts by mass or more and 85 parts by mass or less, even more preferably 55 parts by mass or more and 80 parts by mass or less, and even more preferably 60 parts by mass or more and 75 parts by mass or less, when the total amount of the solid contents in the photosensitive resin composition is taken as 100 parts by mass.
  • the term "solid content in the photosensitive resin composition” refers to non-volatile components, and more specifically, to components other than the organic solvent.
  • the crosslinking agent (B) of the present embodiment contains a (meth)acrylate compound.
  • the crosslinking agent (B) of the present embodiment preferably contains a polyfunctional (meth)acrylate compound from the viewpoint of further improving the balance of performance among patterning properties, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device.
  • polyfunctional (meth)acrylate compound of this embodiment examples include bifunctional (meth)acrylates such as diethylene glycol di(meth)acrylate, polyethylene glycol #200 di(meth)acrylate, and polyethylene glycol #400 di(meth)acrylate; trifunctional (meth)acrylates such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and ethoxylated isocyanuric acid triacrylate; pentaerythritol tetra(meth)acrylate;
  • functional (meth)acrylates include tetrafunctional (meth)acrylates such as dipentaerythritol hexa(meth)acrylate, dipentaerythritol octa(meth)acrylate, and decafunctional (meth)acrylates such as tetrapentaerythritol deca(meth)acrylate.
  • the photosensitive resin composition of the present embodiment preferably further contains an antioxidant, more preferably an antioxidant having an isocyanuric acid skeleton.
  • an antioxidant having an isocyanuric acid skeleton By including an antioxidant having an isocyanuric acid skeleton, the oxygen permeability coefficient of the photosensitive resin composition can be easily adjusted to a more appropriate range.
  • the antioxidant of the present embodiment includes at least one selected from the group consisting of, for example, a phenol-based antioxidant, a phosphite-based antioxidant, and a thioether-based antioxidant, and preferably includes a phenol-based antioxidant, and more preferably includes a hindered phenol-based antioxidant.
  • the content of the antioxidant in the photosensitive resin composition of the present embodiment is, when the total amount of the solid contents in the photosensitive resin composition is taken as 100 parts by mass, preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, even more preferably 0.1 parts by mass or more, even more preferably 0.3 parts by mass or more, even more preferably 0.5 parts by mass or more, and even more preferably 0.6 parts by mass or more, and is preferably 10.0 parts by mass or less, more preferably 7.0 parts by mass or less, even more preferably 5.0 parts by mass or less, even more preferably 4.0 parts by mass or less, even more preferably 3.5 parts by mass or less, and even more preferably 3.0 parts by mass or less.
  • the photosensitive resin composition of the present embodiment preferably further contains a surfactant.
  • the surfactant of the present embodiment include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene aryl ethers such as polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether; nonionic surfactants such as polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; EFTOP EF301, EFTOP EF303, and EFTOP EF352 (manufactured by Shin-Akita Chemical Industry Co., Ltd.), Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F444, and Megafac F445; Fluorine-based surfactants commercially available under the names of Gafa
  • silicone-based surfactants such as polyether-modified dimethylsiloxane
  • the surfactant of the present embodiment may contain one or more of these.
  • the surfactant of the present embodiment preferably includes a silicone-based surfactant.
  • the content of the surfactant in the photosensitive resin composition of this embodiment is preferably 0.001 parts by mass or more and 0.5 parts by mass or less, and more preferably 0.01 parts by mass or more and 0.1 parts by mass or less, when the content of polyimide (A) is taken as 100 parts by mass.
  • the photosensitive resin composition of the present embodiment preferably further contains a curing catalyst from the viewpoint of further improving the balance of performance among patterning properties, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device.
  • the curing catalyst of the present embodiment include phosphorus atom-containing compounds such as organic phosphines, tetra-substituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, and adducts of phosphonium compounds and silane compounds; amidines, tertiary amines and derivatives thereof such as dicyandiamide, 2-phenyl-4,5-dihydroxymethylimidazole, 1,8-diazabicyclo[5.4.0]undecene-7, and benzyldimethylamine; and nitrogen atom-containing compounds such as quaternary ammonium salts of the above amidines or the above tertiary amines.
  • the curing catalyst of the present embodiment may contain one or more of these compounds. From the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and reliability of the obtained semiconductor device, the curing catalyst of the present embodiment preferably contains a phosphorus atom-containing compound, and more preferably contains a tetra-substituted phosphonium compound.
  • the content of the curing catalyst in the photosensitive resin composition of this embodiment is preferably 0.1 parts by mass or more and 5.0 parts by mass or less, and more preferably 0.5 parts by mass or more and 2.0 parts by mass or less, when the content of polyimide (A) is taken as 100 parts by mass, from the viewpoint of further improving the performance balance of patterning property, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device.
  • the photosensitive resin composition of the present embodiment may further contain other additives, such as a leveling agent, a flame retardant, and a plasticizer, as necessary.
  • the photosensitive resin composition of the present embodiment preferably further contains an organic solvent.
  • the organic solvent of the present embodiment is preferably ⁇ -butyrolactone (GBL), ⁇ -valerolactone (GVL), 2,6-lutidine, pyruvic acid N,N-dimethylacetamide, 3-methoxy-N,N-dimethylpropionamide, dimethylsulfoxide (DMSO), diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGME), or the like.
  • GBL ⁇ -butyrolactone
  • EL ethyl lactate
  • the content of the organic solvent in the photosensitive resin composition of this embodiment is, when the total amount of the solids in the photosensitive resin composition is taken as 100 parts by mass, preferably 50 parts by mass or more, more preferably 100 parts by mass or more, even more preferably 150 parts by mass or more, even more preferably 200 parts by mass or more, even more preferably 230 parts by mass or more, even more preferably 260 parts by mass or more, and is preferably 1,000 parts by mass or less, more preferably 800 parts by mass or less, even more preferably 600 parts by mass or less, even more preferably 500 parts by mass or less, even more preferably 400 parts by mass or less, and even more preferably 350 parts by mass or less.
  • the content of the organic solvent in the photosensitive resin composition of this embodiment is, when the total amount of the solid contents in the photosensitive resin composition is taken as 100 parts by mass, preferably 50 parts by mass or more and 1,000 parts by mass or less, more preferably 100 parts by mass or more and 800 parts by mass or less, even more preferably 150 parts by mass or more and 600 parts by mass or less, even more preferably 200 parts by mass or more and 500 parts by mass or less, even more preferably 230 parts by mass or more and 400 parts by mass or less, and even more preferably 260 parts by mass or more and 350 parts by mass or less.
  • the content of the fluorine atom-containing polymer in the photosensitive resin composition of this embodiment when the total amount of the solid contents in the photosensitive resin composition is taken as 100 parts by mass, is preferably 0 parts by mass or more and 30 parts by mass or less, more preferably 0 parts by mass or more and 20 parts by mass or less, even more preferably 0 parts by mass or more and 10 parts by mass or less, even more preferably 0 parts by mass or more and 5 parts by mass or less, even more preferably 0 parts by mass or more and 1 part by mass or less, even more preferably 0 parts by mass or more and 0.1 parts by mass or less, even more preferably 0 parts by mass or more and 0.05 parts by mass or less, and even more preferably 0 parts by mass or more and 0.01 parts by mass or less.
  • the content of the alkali-soluble resin in the photosensitive resin composition of this embodiment is preferably 0 parts by mass or more and preferably 30 parts by mass or less, more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 5 parts by mass or less, even more preferably 1 part by mass or less, even more preferably 0.1 parts by mass or less, even more preferably 0.05 parts by mass or less, and even more preferably 0.01 parts by mass or less, when the total amount of the solids in the photosensitive resin composition is taken as 100 parts by mass.
  • the content of the alkali-soluble resin in the photosensitive resin composition of this embodiment is preferably 0 parts by mass or more and 30 parts by mass or less, more preferably 0 parts by mass or more and 20 parts by mass or less, even more preferably 0 parts by mass or more and 10 parts by mass or less, even more preferably 0 parts by mass or more and 5 parts by mass or less, even more preferably 0 parts by mass or more and 1 part by mass or less, even more preferably 0 parts by mass or more and 0.1 parts by mass or less, even more preferably 0 parts by mass or more and 0.05 parts by mass or less, and even more preferably 0 parts by mass or more and 0.01 parts by mass or less, when the total amount of the solids in the photosensitive resin composition is taken as 100 parts by mass.
  • the alkali-soluble resin is a resin that dissolves in an alkali developer to a sufficient
  • the method for preparing the photosensitive resin composition in this embodiment is not limited, and any known method can be used depending on the components contained in the photosensitive resin composition.
  • the above-mentioned components can be mixed and dissolved in a solvent to prepare the composition.
  • the photosensitive resin composition of the present embodiment can be suitably used in semiconductor devices because the reliability of the resulting semiconductor devices is improved.
  • the photosensitive resin composition of the present embodiment is preferably used for forming a resin film for a semiconductor device such as a permanent film, a resist, etc.
  • the photosensitive resin composition of the present embodiment is preferably used for applications using a permanent film because the reliability of the semiconductor device obtained from the composition is improved.
  • the permanent film is a resin film obtained by pre-baking, exposing, and developing a photosensitive resin composition, patterning it into a desired shape, and then curing it by heat treatment.
  • the permanent film can be used as a protective film, an interlayer film, a dam material, etc. of a semiconductor device.
  • the resist is composed of a resin film obtained by applying a photosensitive resin composition to an object to be masked by the resist by a method such as spin coating, roll coating, flow coating, dip coating, spray coating, doctor coating, or the like, and then removing the solvent from the photosensitive resin composition.
  • the cured product of this embodiment is a cured product of the photosensitive resin composition of this embodiment.
  • the cured product of the present embodiment can be produced, for example, by applying the photosensitive resin composition of the present embodiment to a substrate, pre-baking to dry and form a resin film, then exposing and developing to pattern the resin film into a desired shape, and then heat-treating the resin film to cure it.
  • the pre-baking conditions can be, for example, a heat treatment at 90° C. to 130° C. for 30 seconds to 1 hour, and the heat treatment conditions can be, for example, a heat treatment at 150° C. to 250° C. for 30 minutes to 10 hours.
  • the semiconductor device of the present embodiment includes the cured product of the present embodiment. Since the photosensitive resin composition of this embodiment improves the reliability of the resulting semiconductor device, the semiconductor device of this embodiment has improved reliability.
  • the semiconductor device of this embodiment preferably includes an interlayer insulating film, a resin film containing the cured product of this embodiment on the interlayer insulating film, and rewiring embedded in the resin film.
  • FIG. 1 is a schematic cross-sectional view showing an example of the structure of the semiconductor device according to the present embodiment.
  • the semiconductor device 100 of this embodiment can be a semiconductor device including the above-mentioned resin film.
  • one or more of the group consisting of the passivation film 32, the insulating layer 42, and the insulating layer 44 can be the resin film including the cured product of this embodiment.
  • the resin film is preferably the above-mentioned permanent film.
  • the semiconductor device 100 is, for example, a semiconductor chip.
  • the semiconductor device 100 is mounted on a wiring board via bumps 52 to obtain a semiconductor package.
  • the semiconductor device 100 includes a semiconductor substrate on which semiconductor elements such as transistors are provided, and a multi-layer wiring layer (not shown) provided on the semiconductor substrate.
  • the uppermost layer of the multi-layer wiring layer includes an interlayer insulating film 30 and a top-layer wiring 34 provided on the interlayer insulating film 30.
  • the top-layer wiring 34 is made of, for example, aluminum Al.
  • a passivation film 32 is provided on the interlayer insulating film 30 and the top-layer wiring 34. An opening is provided in a part of the passivation film 32 to expose the top-layer wiring 34.
  • TMPBP-TME 4-[4-(1,3-dioxoisobenzofuran-5-ylcarbonyloxy)-2,3,5-trimethylphenyl]-2,3,6-trimethylphenyl-1,3-dioxoisobenzofuran-5-carboxylate (hereinafter also referred to as TMPBP-TME), represented by the formula below.
  • Antioxidant 1 A compound represented by the following formula (KEMINOX 179, manufactured by Chemipro Chemicals)
  • the photosensitive resin composition of each Example and Comparative Example was applied onto an 8-inch silicon wafer using a spin coater. After application, the wafer was prebaked at 110° C. for 3 minutes on a hot plate in the atmosphere to obtain a coating film with a thickness of about 5 ⁇ m.
  • This coating film was irradiated with i-rays through a mask on which via patterns of multiple widths (4 ⁇ m and 5 ⁇ m) were drawn. For irradiation, an i-ray stepper (Nikon Corporation, NSR-4425i) was used.
  • a copper wiring having a line width of 5 ⁇ m and a thickness of 2 ⁇ m was formed on an 8-inch silicon wafer.
  • the photosensitive resin composition of each Example and each Comparative Example was applied to the silicon wafer surface on which the copper wiring was formed so that the film thickness after drying was 10 ⁇ m, and after pre-baking at 110 ° C. for 3 minutes, exposure to 600 mJ / cm 2 was performed with a high-pressure mercury lamp, and then post-baking was performed for 3 hours at 230 ° C. in a nitrogen atmosphere to harden the photosensitive resin composition, and a test piece was obtained. Next, the obtained test piece was heat-treated under the conditions of 230 ° C. and 30 minutes in air.
  • test piece was cut perpendicular to the silicon wafer surface, and the cross section was observed with a scanning electron microscope (Hitachi High-Tech Corporation, S-4700), and the reliability was evaluated according to the following criteria.
  • the results are shown in Table 1.
  • Tg Glass transition temperature
  • TMA-7100 thermomechanical analyzer
  • Reference Signs List 100 Semiconductor device 30 Interlayer insulating film 32 Passivation film 34 Top layer wiring 40 Rewiring layer 42 Insulating layer 44 Insulating layer 46 Rewiring 50 UBM layer 52 Bump

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018047688A1 (ja) * 2016-09-09 2018-03-15 東レ株式会社 樹脂組成物
WO2022270541A1 (ja) * 2021-06-25 2022-12-29 住友ベークライト株式会社 ネガ型感光性樹脂組成物、ネガ型感光性ポリマー、硬化膜および半導体装置
WO2024095884A1 (ja) * 2022-10-31 2024-05-10 富士フイルム株式会社 樹脂組成物、硬化物、積層体、硬化物の製造方法、積層体の製造方法、半導体デバイスの製造方法、及び、半導体デバイス
JP2024163067A (ja) * 2023-05-10 2024-11-21 旭化成株式会社 ネガ型感光性樹脂組成物及び硬化レリーフパターンの製造方法

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JP2018070829A (ja) * 2016-11-02 2018-05-10 東レ株式会社 樹脂組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018047688A1 (ja) * 2016-09-09 2018-03-15 東レ株式会社 樹脂組成物
WO2022270541A1 (ja) * 2021-06-25 2022-12-29 住友ベークライト株式会社 ネガ型感光性樹脂組成物、ネガ型感光性ポリマー、硬化膜および半導体装置
WO2024095884A1 (ja) * 2022-10-31 2024-05-10 富士フイルム株式会社 樹脂組成物、硬化物、積層体、硬化物の製造方法、積層体の製造方法、半導体デバイスの製造方法、及び、半導体デバイス
JP2024163067A (ja) * 2023-05-10 2024-11-21 旭化成株式会社 ネガ型感光性樹脂組成物及び硬化レリーフパターンの製造方法

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