WO2025142645A1 - 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
WO2025142645A1
WO2025142645A1 PCT/JP2024/044636 JP2024044636W WO2025142645A1 WO 2025142645 A1 WO2025142645 A1 WO 2025142645A1 JP 2024044636 W JP2024044636 W JP 2024044636W WO 2025142645 A1 WO2025142645 A1 WO 2025142645A1
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WIPO (PCT)
Prior art keywords
mass
resin composition
photosensitive resin
parts
group
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
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PCT/JP2024/044636
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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 JP2025525041A priority Critical patent/JP7736225B1/ja
Publication of WO2025142645A1 publication Critical patent/WO2025142645A1/ja
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/32—Cyanuric acid; Isocyanuric acid
    • 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
    • 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
    • C08G73/12—Unsaturated 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 cured product that can improve the performance balance between patterning properties and the reliability of the resulting semiconductor device, as well as a semiconductor device with improved reliability.
  • a photosensitive resin composition containing a polyimide (A) having a double bond in the side chain, a crosslinking agent (B) containing a (meth)acrylate compound, a polymerization initiator (C), and an antioxidant (D) having an isocyanuric acid skeleton can improve the performance balance between patterning properties and the reliability of the resulting semiconductor device, and have completed the present invention.
  • the present invention provides the following photosensitive resin composition, cured product, and semiconductor device.
  • a polyimide (A) having a double bond in a side chain; A crosslinking agent (B) containing a (meth)acrylate compound; A polymerization initiator (C); An antioxidant (D) having an isocyanuric acid skeleton; A photosensitive resin composition comprising: [2] The photosensitive resin composition according to [1], wherein the antioxidant (D) contains a compound represented by the following general formula (1): (In the general formula (1), R 11 , R 12 and R 13 each independently represent a hydrogen atom, a hydroxy group, an alkyl group or alkoxy group having 1 to 20 carbon atoms which may contain a hydroxy group, or an aryl group or aralkyl group having 6 to 30 carbon atoms which may contain at least one substituent selected from the group consisting of a hydroxy group, an alkyl group and an alkoxy group.) [3] The photosensitive resin composition according to [2], wherein at least one of R 11 , R 12 and R 13 in the general formula (1) is
  • FIG. 1 is a schematic cross-sectional view showing an example of a structure of a semiconductor device.
  • 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 (3a), a group represented by the following general formula (3b), and a group represented by the following general formula (3c), from the viewpoint of further improving the performance balance of 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 (3b).
  • 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.
  • 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.
  • the polyimide (A) of this embodiment preferably contains a structural unit represented by the following general formula (4) 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.
  • R is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.
  • X is preferably any one selected from the group consisting of a linear or branched alkylene group having 1 to 5 carbon atoms and a substituted or unsubstituted fluorene group, more preferably any one selected from the group consisting of a linear or branched alkylene group having 1 to 3 carbon atoms and an unsubstituted fluorene group, and even more preferably a linear or branched alkylene group having 1 to 3 carbon atoms.
  • the 9-position of the fluorene serves as the binding site.
  • the polyimide (A) of this embodiment preferably contains a structural unit (a) represented by the following general formula (5), 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 includes a structural unit (a p ) represented by general formula (5) in which at least one of m1 and m2 is 1 or more, and a structural unit (a q ) represented by general formula (5) 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 15 mol % or more, more preferably 20 mol % or more, even more preferably 30 mol % or more, even 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 15 mol % or more and 100 mol % or less, more preferably 20 mol % or more and 100 mol % or less, even more preferably 30 mol % or more and 100 mol % or less, even 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 %
  • 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 this embodiment is, when the total amount of the solids 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 45 parts by mass or more, even more preferably 50 parts by mass or more, and even more preferably 55 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 45 parts by mass or more and 85 parts by mass or less, even more preferably 50 parts by mass or more and 80 parts by mass or less, and even more preferably 55 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 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 crosslinking agent (B) of this embodiment preferably contains a polyfunctional (meth)acrylate compound having 3 to 20 (meth)acryloyloxy groups or (meth)acryloyl groups in the molecule, more preferably contains a polyfunctional (meth)acrylate compound having 4 to 15 (meth)acryloyloxy groups or (meth)acryloyl groups in the molecule, and even more preferably contains a polyfunctional (meth)acrylate compound having 5 to 10 (meth)acryloyloxy groups or (meth)acryloyl groups in the molecule, from the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device.
  • the crosslinking agent (B) of the present embodiment may contain a (meth)acrylate compound having an isocyanuric acid skeleton.
  • the number of (meth)acryloyloxy groups or (meth)acryloyl groups contained in the molecule of the (meth)acrylate compound having an isocyanuric acid skeleton of this embodiment is preferably 1 to 6, more preferably 2 to 3.
  • the crosslinking agent (B) of this embodiment preferably contains an epoxy compound from the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and reliability of the resulting semiconductor device.
  • the epoxy compound of the present embodiment preferably contains an epoxy compound having a (meth)acryloyloxy group or a (meth)acryloyl group, from the viewpoint of further improving the performance balance of patterning properties, copper adhesion, mechanical strength, and reliability of the obtained semiconductor device.
  • the number of glycidyl groups contained in the molecule of the epoxy compound having a (meth)acryloyloxy group or a (meth)acryloyl group of this embodiment is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1.
  • the number of (meth)acryloyloxy groups or (meth)acryloyl groups contained in the molecule of the epoxy compound having a (meth)acryloyloxy group or a (meth)acryloyl group of the present embodiment is preferably 0 or more and 6 or less, more preferably 0 or more and 2 or less, and even more preferably 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
PCT/JP2024/044636 2023-12-26 2024-12-17 感光性樹脂組成物、硬化物および半導体装置 Pending WO2025142645A1 (ja)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021152634A (ja) * 2020-03-19 2021-09-30 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及びその用途
JP2022135427A (ja) * 2021-03-05 2022-09-15 住友ベークライト株式会社 ネガ型感光性樹脂組成物およびその用途
WO2022202098A1 (ja) * 2021-03-22 2022-09-29 日産化学株式会社 感光性樹脂組成物
WO2022210225A1 (ja) * 2021-03-30 2022-10-06 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、及び、半導体デバイス
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
WO2023032820A1 (ja) * 2021-08-31 2023-03-09 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、並びに、化合物
WO2023106101A1 (ja) * 2021-12-09 2023-06-15 日産化学株式会社 樹脂組成物
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

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021152634A (ja) * 2020-03-19 2021-09-30 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及びその用途
JP2022135427A (ja) * 2021-03-05 2022-09-15 住友ベークライト株式会社 ネガ型感光性樹脂組成物およびその用途
WO2022202098A1 (ja) * 2021-03-22 2022-09-29 日産化学株式会社 感光性樹脂組成物
WO2022210225A1 (ja) * 2021-03-30 2022-10-06 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、及び、半導体デバイス
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
WO2023032820A1 (ja) * 2021-08-31 2023-03-09 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、並びに、化合物
WO2023106101A1 (ja) * 2021-12-09 2023-06-15 日産化学株式会社 樹脂組成物
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

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JP7736225B1 (ja) 2025-09-09

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