WO2025094282A1 - 感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法 - Google Patents

感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法 Download PDF

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WO2025094282A1
WO2025094282A1 PCT/JP2023/039303 JP2023039303W WO2025094282A1 WO 2025094282 A1 WO2025094282 A1 WO 2025094282A1 JP 2023039303 W JP2023039303 W JP 2023039303W WO 2025094282 A1 WO2025094282 A1 WO 2025094282A1
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mass
photosensitive
photosensitive layer
binder polymer
meth
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English (en)
French (fr)
Japanese (ja)
Inventor
夏木 戸田
琢 澤木
謙介 吉原
陽介 賀口
博史 小野
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Resonac Corp
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Resonac Corp
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Priority to JP2025554397A priority Critical patent/JPWO2025094282A1/ja
Priority to EP23957610.1A priority patent/EP4675350A1/en
Priority to PCT/JP2023/039303 priority patent/WO2025094282A1/ja
Priority to KR1020257041999A priority patent/KR20260011754A/ko
Priority to CN202380096538.4A priority patent/CN120981769A/zh
Publication of WO2025094282A1 publication Critical patent/WO2025094282A1/ja
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor

Definitions

  • This disclosure relates to a photosensitive element, a method for forming a resist pattern, and a method for manufacturing a printed wiring board.
  • photosensitive resin compositions and photosensitive elements comprising a layer formed on a support film using the photosensitive resin composition (hereinafter also referred to as a "photosensitive layer”) are widely used as resist materials used in etching processes, plating processes, etc. (see, for example, Patent Document 1).
  • Printed wiring boards are manufactured using the above-mentioned photosensitive element, for example, in the following manner. That is, first, the photosensitive layer of the photosensitive element is laminated onto a circuit-forming substrate such as a copper-clad laminate. Next, the photosensitive layer is exposed to light through a mask film or the like to form a photocured portion. At this time, the support film is peeled off before or after exposure. After that, the areas of the photosensitive layer other than the photocured portion are removed with a developer to form a resist pattern. Next, the resist pattern is used as a resist to perform an etching process or a plating process to form a conductor pattern, and finally the photocured portion of the photosensitive layer (resist pattern) is peeled off (removed).
  • the present disclosure aims to provide a photosensitive element that has excellent developability and resolution and is capable of forming finer resist patterns, a method for forming resist patterns, and a method for manufacturing printed wiring boards.
  • a photosensitive element comprising a support and a photosensitive layer formed on the support using a photosensitive resin composition, wherein the photosensitive layer has a thickness of 10 ⁇ m or less, the photosensitive layer contains a binder polymer, a photopolymerizable compound, a photopolymerization initiator, and a sensitizer, the binder polymer has a first structural unit derived from acrylic acid, and the acid value of the binder polymer is 140 to 165 mgKOH/g.
  • a photosensitive element comprising a support and a photosensitive layer formed on the support using a photosensitive resin composition, the photosensitive layer having a thickness of 10 ⁇ m or less, the photosensitive layer containing a binder polymer, a photopolymerizable compound, a photopolymerization initiator, and a sensitizer, the binder polymer having a first structural unit derived from acrylic acid and a second structural unit derived from styrene or a styrene derivative, and the content of the first structural unit is 18.0 to 22.0 mass % and the content of the second structural unit is 60.0 mass % or more, based on the total mass of the structural units derived from the polymerizable monomers constituting the binder polymer.
  • a method for forming a resist pattern comprising the steps of: forming a photosensitive layer on a substrate using the photosensitive element according to any one of the above [1] to [6]; irradiating at least a portion of the photosensitive layer with active light to form a photocured portion; and removing an unphotocured portion of the photosensitive layer from the substrate to form a resist pattern.
  • a method for producing a printed wiring board comprising the step of etching or plating a substrate on which a resist pattern has been formed by the method for forming a resist pattern according to [7] above to form a conductor pattern.
  • the present disclosure provides a photosensitive element that has excellent developability and resolution and is capable of forming finer resist patterns, a method for forming resist patterns, and a method for manufacturing printed wiring boards.
  • FIG. 1 is a schematic cross-sectional view illustrating one embodiment of a photosensitive element.
  • the term “process” includes not only independent processes, but also processes that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved.
  • the term “layer” includes structures that are formed on the entire surface as well as structures that are formed on a portion of the surface when observed in a plan view.
  • a numerical range indicated using “ ⁇ ” indicates a range that includes the numerical values before and after " ⁇ " as the minimum and maximum values, respectively.
  • the upper or lower limit of a numerical range of a certain stage may be replaced with the upper or lower limit of a numerical range of another stage.
  • the upper or lower limit of the numerical range may be replaced with the values shown in the examples.
  • the amount of each component in a photosensitive resin composition means the total amount of the multiple substances present in the composition when the composition contains multiple substances corresponding to each component, unless otherwise specified.
  • solid content refers to the non-volatile content in the photosensitive resin composition excluding volatile substances (water, solvent, etc.).
  • solid content refers to components other than the solvent that do not volatilize and remain when the photosensitive resin composition is dried, as described below, and includes components that are liquid, syrup-like, or waxy at room temperature (25°C).
  • the photosensitive element of the present embodiment includes a support and a photosensitive layer formed on the support.
  • the photosensitive layer may be laminated on a substrate and then exposed to light without peeling off the support (support film).
  • FIG. 1 is a schematic cross-sectional view of a photosensitive element according to one embodiment.
  • the photosensitive element 1 comprises a support 2, a photosensitive layer 3 formed on the support 2, and other layers such as a protective layer 4 that are provided as necessary.
  • a protective layer 4 that are provided as necessary.
  • the support 2 and the protective layer 4 may each be a polymer film having heat resistance and solvent resistance, for example, a polyester film such as a polyethylene terephthalate film, a polyethylene film, a polyolefin film such as a polypropylene film, etc.
  • the support 2 and the protective layer 4 may each be a film of a hydrocarbon-based polymer other than polyolefin.
  • the film of a hydrocarbon-based polymer containing polyolefin may have a low density, for example, a density of 1.014 g/cm 3 or less.
  • the support 2 and the protective layer 4 may each be a stretched film obtained by stretching the low-density hydrocarbon-based polymer film.
  • the type of the polymer film constituting the protective layer 4 may be the same as or different from the type of the polymer film constituting the support 2.
  • polymer films can be purchased, for example, as polyethylene terephthalate films such as the PS series (e.g., PS-25) manufactured by Teijin Limited, polyethylene films such as NF-15 manufactured by Tamapoly Co., Ltd., or polypropylene films manufactured by Oji Paper Co., Ltd. (e.g., Alphan MA-410, E-200C) and Shin-Etsu Film Co., Ltd.
  • PS series e.g., PS-25
  • polyethylene films such as NF-15 manufactured by Tamapoly Co., Ltd.
  • polypropylene films manufactured by Oji Paper Co., Ltd. e.g., Alphan MA-410, E-200C
  • the thickness of the support 2 may be 1 ⁇ m or more or 5 ⁇ m or more from the viewpoint of suppressing damage to the support 2 when peeling the support 2 from the photosensitive layer 3, and may be 100 ⁇ m or less, 50 ⁇ m or less, or 30 ⁇ m or less from the viewpoint of suitable exposure even when exposure is performed through the support 2.
  • the thickness of the protective layer 4 may be 1 ⁇ m or more, 5 ⁇ m or more, or 15 ⁇ m or more from the viewpoint of suppressing damage to the protective layer 4 when the photosensitive layer 3 and the support 2 are laminated onto the substrate while the protective layer 4 is peeled off, and may be 100 ⁇ m or less, 50 ⁇ m or less, or 30 ⁇ m or less from the viewpoint of improving productivity.
  • the thickness of the photosensitive layer 3 is 10 ⁇ m or less.
  • the thickness of the photosensitive layer 3 after drying may be 1 ⁇ m or more, 2 ⁇ m or more, 3 ⁇ m or more, 4 ⁇ m or more, or 5 ⁇ m or more, and from the viewpoint of further improving resolution, it may be 9 ⁇ m or less, 8 ⁇ m or less, or 7 ⁇ m or less.
  • the photosensitive layer 3 is a layer formed using a photosensitive resin composition described below, and contains a binder polymer, a photopolymerizable compound, a photopolymerization initiator, and a sensitizer.
  • the photosensitive layer 3 may contain a polymerization inhibitor, an ultraviolet absorber, or other components as necessary. Each component used in the photosensitive resin composition in this embodiment will be described in more detail below.
  • the photosensitive resin composition according to this embodiment contains a binder polymer having a specific structure as the component (A), and thus the developability and resolution of the photosensitive layer formed from the photosensitive resin composition can be improved.
  • the binder polymer according to this embodiment has a first structural unit derived from acrylic acid, and the acid value of the binder polymer may be 140 to 165 mg KOH/g.
  • the binder polymer according to this embodiment has a first structural unit derived from acrylic acid and a second structural unit derived from styrene or a styrene derivative, and the content of the first structural unit may be 18.0 to 22.0 mass% and the content of the second structural unit may be 60.0 mass% or more based on the total mass of the structural units derived from the polymerizable monomers constituting the binder polymer.
  • Component (A) can be produced by radical polymerization of a polymerizable monomer containing acrylic acid. By having component (A) have a first structural unit derived from acrylic acid, the alkaline developability of the photosensitive resin composition can be improved.
  • the content of the first structural unit in component (A) may be 18.0% by mass or more, 18.5% by mass or more, 19.0% by mass or more, or 19.5% by mass or more, based on the total mass of the structural units derived from the polymerizable monomers constituting the binder polymer (100% by mass), from the viewpoint of further shortening the development time.
  • the content of the first structural unit may be 22.0% by mass or less, 21.5% by mass or less, or 21.0% by mass or less, from the viewpoint of further improving the resolution.
  • the content of the first structural unit may be 18.0 to 22.0% by mass, 18.5 to 22.0% by mass, 19.0 to 21.5% by mass, or 19.5 to 21.0% by mass, from the viewpoint of improving the developability and the resolution in a well-balanced manner.
  • the (A) component has a second structural unit derived from styrene or a styrene derivative, which can improve the resolution and adhesion of the photosensitive resin composition.
  • styrene derivatives include vinyl toluene, ⁇ -methyl styrene, p-methyl styrene, and p-ethyl styrene.
  • the content of the second structural unit in component (A) may be 60.0% by mass or more, 64.0% by mass or more, 68.0% by mass or more, or 70.0% by mass or more, based on the total mass of the structural units derived from the polymerizable monomers constituting the binder interpolymer, from the viewpoint of further improving adhesion.
  • the content of the second structural unit may be 85.0% by mass or less, 84.0% by mass or less, 83.0% by mass or less, or 80% by mass or less, from the viewpoint of further shortening the peeling time.
  • the content of the styrene-based structural unit may be 60.0 to 85.0% by mass, 64.0 to 84.0% by mass, 68.0 to 83.0% by mass, or 70.0 to 80.0% by mass.
  • the (A) component has a third structural unit derived from a (meth)acrylate compound having an alicyclic structure, which makes it possible to adjust the balance between the developability and resolution of the photosensitive resin composition.
  • Examples of (meth)acrylates having an alicyclic structure include cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, cyclopentanyl (meth)acrylate, and dicyclopentanyl (meth)acrylate.
  • the content of the third structural unit may be 0.5 mass% or more, 1.0 mass% or more, 2.0 mass% or more, or 3.0 mass% or more, based on the total mass of the structural units derived from the polymerizable monomers constituting the binder polymer, from the viewpoint of further improving the resolution of the photosensitive resin composition, and may be 18.0 mass% or less, 15.0 mass% or less, 10.0 mass% or less, or 8.0 mass% or less, from the viewpoint of further improving the developability of the photosensitive resin composition.
  • Component (A) may further contain structural units derived from polymerizable monomers other than those mentioned above (hereinafter also referred to as "other monomers”).
  • other monomers include methacrylic acid, 2-ethylhexyl (meth)acrylate, hydroxyethyl (meth)acrylate, benzyl (meth)acrylate or derivatives thereof, furfuryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, ⁇ -furyl (meth)acrylic acid, ⁇ -styryl (meth)acrylic acid, maleic acid, maleic anhydride, maleic acid monoalkyl
  • the weight average molecular weight (Mw) of component (A) may be 25,000 to 50,000, 30,000 to 48,000, 32,000 to 46,000, or 35,000 to 44,000. When Mw is 50,000 or less, the resolution and developability tend to be improved, and when Mw is 25,000 or more, chipping and peeling of the resist pattern tend to be less likely to occur.
  • the dispersity (Mw/Mn) of component (A) may be 1.0 to 3.0, 1.0 to 2.5, or 1.0 to 2.3. When the dispersity is smaller, the resolution tends to be improved.
  • Mw and Mn can be measured, for example, by gel permeation chromatography (GPC) using a calibration curve of standard polystyrene. More specifically, they can be measured under the conditions described in the Examples.
  • GPC gel permeation chromatography
  • the acid value of component (A) may be 140 to 165 mgKOH/g, 144 to 163 mgKOH/g, 145 to 160 mgKOH/g, or 146 to 158 mgKOH/g from the viewpoint of achieving both developability and strippability.
  • the acid value of component (A) can be adjusted by a structural unit derived from acrylic acid.
  • the acid value of component (A) can be measured in accordance with JIS K6901:2008 5.3.2.
  • the glass transition temperature (Tg) of component (A) may be 70 to 125°C, 90 to 120°C, 94 to 110°C, or 96 to 108°C from the viewpoint of resolution or adhesion.
  • the Tg of component (A) is a value determined according to the Fox formula, and can be calculated from the mass of each polymerizable monomer constituting component (A) and the Tg of the homopolymer of each polymerizable monomer.
  • the content of the (A) component may be 20 parts by mass or more, 30 parts by mass or more, 40 parts by mass or more, or 50 parts by mass or more, relative to 100 parts by mass of the total amount of the (A) component and the (B) component, from the viewpoint of excellent formability of the film, and may be 80 parts by mass or less, 70 parts by mass or less, or 60 parts by mass or less, from the viewpoint of further improving sensitivity and resolution.
  • the component (B) component is not particularly limited as long as it has at least one ethylenically unsaturated bond and is a photopolymerizable compound. From the viewpoint of improving the alkali developability, resolution, and peelability after curing, the component (B) preferably contains at least one bisphenol type (meth)acrylate, and among the bisphenol type (meth)acrylates, it is more preferable to contain bisphenol A type (meth)acrylate.
  • bisphenol A type (meth)acrylates examples include 2,2-bis(4-((meth)acryloxypolyethoxy)phenyl)propane, 2,2-bis(4-((meth)acryloxypolypropoxy)phenyl)propane, 2,2-bis(4-((meth)acryloxypolybutoxy)phenyl)propane, and 2,2-bis(4-((meth)acryloxypolyethoxypolypropoxy)phenyl)propane.
  • 2,2-bis(4-((meth)acryloxypolyethoxy)phenyl)propane is preferred from the viewpoint of further improving resolution and release properties.
  • a compound having 10 or more oxyethylene groups may be used, or a compound having less than 10 oxyethylene groups may be used, or a compound having 10 or more oxyethylene groups may be used in combination with a compound having less than 10 oxyethylene groups.
  • bisphenol A type (meth)acrylates include, for example, BPE-200 (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.) as 2,2-bis(4-((meth)acryloxydipropoxy)phenyl)propane, BP-2EM (trade name, manufactured by Kyoeisha Chemical Co., Ltd.) as ethoxylated bisphenol A dimethacrylate, and BPE-500 (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.) and FA-321M (trade name, manufactured by Resonac Co., Ltd.) as 2,2-bis(4-(methacryloxypentaethoxy)phenyl)propane. These bisphenol A type (meth)acrylates may be used alone or in combination of two or more types.
  • the content of the bisphenol type (meth)acrylate may be 40 to 98 mass%, 50 to 97 mass%, 60 to 95 mass%, or 70 to 90 mass% based on the total amount of component (B). If the content is 40 mass% or more, the resolution, adhesion, and suppression of resist tail generation will be better, and if it is 98 mass% or less, the development time will be appropriately short and development residue will be less likely to occur.
  • the (B) component other than the bisphenol type (meth)acrylate may further include at least one polyalkylene glycol di(meth)acrylate having at least one of a (poly)oxyethylene chain and a (poly)oxypropylene chain in the molecule, from the viewpoint of improving the flexibility of the cured product (cured film), and may further include a polyalkylene glycol di(meth)acrylate having both a (poly)oxyethylene chain and a (poly)oxypropylene chain in the molecule.
  • the total number of oxyethylene groups (EO groups) and/or oxypropylene groups (PO groups) in the polyalkylene glycol di(meth)acrylate may be 2 to 40, 4 to 30, or 6 to 20, from the viewpoint of further improving adhesion and resolution.
  • polyalkylene glycol di(meth)acrylates examples include FA-023M (trade name, manufactured by Resonac Corporation), FA-024M (trade name, manufactured by Resonac Corporation), and NK Ester HEMA-9P (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.). These may be used alone or in combination of two or more.
  • the content of polyalkylene glycol di(meth)acrylate may be 2 to 40 mass%, 3 to 30 mass%, or 5 to 20 mass% based on the total amount of component (B).
  • component (B) may also be used as component (B).
  • component (B) may contain at least one selected from nonylphenoxy polyethyleneoxy acrylate and phthalic acid compounds.
  • the content thereof may be 5 to 50 mass%, 5 to 40 mass%, or 10 to 30 mass% based on the total amount of component (B).
  • nonylphenoxy polyethyleneoxyacrylates include nonylphenoxy triethyleneoxyacrylate, nonylphenoxy tetraethyleneoxyacrylate, nonylphenoxy pentaethyleneoxyacrylate, nonylphenoxy hexaethyleneoxyacrylate, nonylphenoxy heptaethyleneoxyacrylate, nonylphenoxy octaethyleneoxyacrylate, nonylphenoxy nonaethyleneoxyacrylate, nonylphenoxy decaethyleneoxyacrylate, and nonylphenoxy undecaethyleneoxyacrylate.
  • phthalic acid compounds include ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ '-(meth)acryloyloxyethyl-o-phthalate, ⁇ -hydroxyethyl- ⁇ '-(meth)acryloyloxyethyl-o-phthalate, and ⁇ -hydroxypropyl- ⁇ '-(meth)acryloyloxyethyl-o-phthalate.
  • ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ '-methacryloyloxyethyl-o-phthalate is commercially available as FA-MECH (trade name, manufactured by Resonac Corporation).
  • component (B) may contain a (meth)acrylic acid polyol ester.
  • (meth)acrylic acid polyol esters include trimethylolpropane polyethoxy tri(meth)acrylate, trimethylolpropane polypropoxy tri(meth)acrylate, trimethylolpropane polybutoxy tri(meth)acrylate, trimethylolpropane polyethoxy polypropoxy tri(meth)acrylate, trimethylolethane polyethoxy tri(meth)acrylate, trimethylolethane polypropoxy tri(meth)acrylate, trimethylolethane polybut ...propoxy tri(meth)acrylate, trimethylolethane polybutoxy tri(meth)acrylate, trimethylolethane polyethoxy tri(meth)acrylate, trimethylolethane polypropoxy tri(meth)acrylate, trimethylolethane polybutoxy tri(meth)acrylate, trimethylolethane polypropoxy tri(meth)acrylate,
  • the content of component (B) is preferably 20 to 60 parts by mass, more preferably 30 to 55 parts by mass, and even more preferably 35 to 50 parts by mass, relative to 100 parts by mass of the total amount of components (A) and (B).
  • the photosensitive resin composition has better photosensitivity and coating properties in addition to better resolution and adhesion.
  • component (C) Photopolymerization initiator
  • the component (C) is not particularly limited as long as it is a component that can polymerize the component (B), and can be appropriately selected from commonly used photopolymerization initiators.
  • Examples of the (C) component include hexaarylbiimidazole compounds; aromatic ketone compounds such as benzophenone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propanone-1; alkyl aryl ketones; These include quinone compounds such as tribenzone; benzoin ether compounds such as benzoin alkyl ether; benzoin compounds such as benzoin and alkylbenzoin; benzyl derivatives such as benzyl dimethyl ketal; and phosphine oxide compounds such as bis(2,4,6-trimethylbenzo
  • Component (C) may contain a hexaarylbiimidazole compound from the viewpoint of improving the adhesion of the photosensitive layer to a smooth substrate.
  • the aryl group in the hexaarylbiimidazole compound may be a phenyl group or the like.
  • the hydrogen atom bonded to the aryl group in the hexaarylbiimidazole compound may be substituted with a halogen atom (such as a chlorine atom).
  • the hexaarylbiimidazole compound may be a 2,4,5-triarylimidazole dimer.
  • 2,4,5-triarylimidazole dimer examples include 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-bis-(m-methoxyphenyl)imidazole dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer.
  • the content of component (C) may be 1.0 to 10 parts by mass, 2.0 to 8.0 parts by mass, 3.0 to 7.0 parts by mass, or 4.0 to 6.0 parts by mass, per 100 parts by mass of the total amount of components (A) and (B). When the content of component (C) is within this range, it becomes easy to improve both photosensitivity and resolution in a well-balanced manner.
  • the photosensitive resin composition according to this embodiment contains the component (D), so that the absorption wavelength of the actinic radiation used for exposure can be effectively utilized.
  • component (D) examples include dialkylaminobenzophenone compounds, pyrazoline compounds, anthracene compounds, coumarin compounds, xanthone compounds, thioxanthone compounds, oxazole compounds, benzoxazole compounds, thiazole compounds, benzothiazole compounds, triazole compounds, stilbene compounds, triazine compounds, thiophene compounds, naphthalimide compounds, triarylamine compounds, and aminoacridine compounds.
  • Component (D) may contain a pyrazoline compound or a dialkylaminobenzophenone compound from the viewpoint of further improving resolution and adhesion.
  • Examples of pyrazoline compounds include 1-(4-methoxyphenyl)-3-styryl-5-phenyl-pyrazoline, 1-phenyl-3-(4-methoxystyryl)-5-(4-methoxyphenyl)-pyrazoline, 1,5-bis-(4-methoxyphenyl)-3-(4-methoxystyryl)-pyrazoline, 1-(4-isopropylphenyl)-3-styryl-5-phenyl-pyrazoline, 1-phenyl-3-(4-isopropylstyryl)-5-(4-isopropylphenyl)-pyrazoline, 1,5-bis-(4-isopropylphenyl)-3-(4-isopropylphenyl)-pyrazoline, 1-(4-isopropyl-phenyl)-3-(4-tert-butyl-styryl)-5-(4-tert-butyl-phenyl)-pyrazoline
  • dialkylaminobenzophenone compounds examples include 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, and 4-benzoyl-4'-methyldiphenyl sulfide.
  • the content of the (D) component may be 1.60 parts by mass or less, 1.50 parts by mass or less, 1.40 parts by mass or less, or 1.35 parts by mass or less, per 100 parts by mass of the (C) component, from the viewpoint of further improving adhesion.
  • the content of the (D) component may be 0.15 to 1.60 parts by mass, 0.20 to 1.50 parts by mass, 0.25 to 1.40 parts by mass, or 0.30 to 1.35 parts by mass, per 100 parts by mass of the (C) component, from the viewpoint of improving developability, adhesion, and peelability in a balanced manner.
  • the content of component (D) may be 0.01 to 0.10 parts by mass, 0.01 to 0.09 parts by mass, or 0.01 to 0.08 parts by mass per 100 parts by mass of the total amount of components (A) and (B).
  • the photosensitive resin composition may further contain a polymerization inhibitor as component (E) from the viewpoint of suppressing polymerization in unexposed areas during resist pattern formation and further improving resolution.
  • a polymerization inhibitor examples include 4-tert-butylcatechol and 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl.
  • the content of component (E) may be 0.001 to 0.10 parts by mass, 0.005 to 0.08 parts by mass, or 0.01 to 0.06 parts by mass per 100 parts by mass of the total amount of components (A) and (B).
  • the photosensitive resin composition may contain an ultraviolet absorber as the component (F).
  • Component (F) may be a compound that absorbs light in the range of 340 to 430 nm, or may be a compound that efficiently absorbs light with a wavelength of 365 nm.
  • the molar absorption coefficient of component (F) for light with a wavelength of 365 nm is in the range of 500 to 50,000 L/(mol cm).
  • the molar absorption coefficient is an index of the ease of light absorption.
  • component (F) effectively absorbs light of the exposure wavelength, and may contain at least one selected from the group consisting of benzophenone compounds, benzotriazole compounds, and triazine compounds, or may contain a benzophenone compound.
  • the benzophenone compound may be a benzophenone compound in which some of the hydrogen atoms are replaced with groups having oxygen atoms, or may be a benzophenone compound having a hydroxyl group.
  • benzophenone compounds include 4,4'-dimethoxybenzophenone, 4,4'-bis(trimethylacetoxy)benzophenone, 2,4,4'-trihydroxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,2',3,4,4'-pentahydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone, and 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid.
  • benzotriazole compounds include 2,2-methylenebis[6-(2H-benzotriazol-2-yl)-4-tert-octylphenol], 2-(2'-hydroxy-5'-methacryloxyethylphenyl)-2H-benzotriazole, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol, and 2-(5-chloro-2H-benzotriazol-2-yl)-6-tert-butyl-4-methylphenol.
  • triazine compounds examples include 2-[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol, and 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine.
  • the content of component (F) may be 0.05 to 5.0 parts by mass, 0.1 to 4.0 parts by mass, or 0.2 to 2.0 parts by mass per 100 parts by mass of the total amount of components (A) and (B).
  • the photosensitive resin composition may further contain one or more other components other than the above-mentioned components.
  • the other components include hydrogen donors (bis[4-(dimethylamino)phenyl]methane, bis[4-(diethylamino)phenyl]methane, leuco crystal violet, N-phenylglycine, etc.), dyes (malachite green, etc.), tribromophenyl sulfone, photocoloring agents, thermal coloring inhibitors, plasticizers (p-toluenesulfonamide, etc.), pigments, fillers, defoamers, flame retardants, stabilizers, adhesion agents, leveling agents, peeling promoters, antioxidants, fragrances, imaging agents, and thermal crosslinking agents.
  • the content of the other components may be 0.005 parts by mass or more or 0.01 parts by mass or more, or may be 20 parts by mass or less, relative to 100 parts by mass of the total amount of the components (A) and
  • the photosensitive resin composition may contain an organic solvent to improve the handling properties of the photosensitive composition and to adjust the viscosity and storage stability.
  • an organic solvent any commonly used organic solvent may be used without any particular restrictions. Examples of the organic solvent include methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N,N-dimethylformamide, propylene glycol monomethyl ether, and mixed solvents thereof. These may be used alone or in combination of two or more.
  • the photosensitive element 1 can be obtained, for example, as follows. First, a photosensitive layer 3 is formed on a support 2. The photosensitive layer 3 can be formed, for example, by applying a photosensitive resin composition containing an organic solvent to form a coating layer, and then drying this coating layer. Next, a protective layer 4 is formed on the surface of the photosensitive layer 3 opposite the support 2.
  • the coating layer is formed by a known method such as roll coating, comma coating, gravure coating, air knife coating, die coating, bar coating, etc.
  • the coating layer is dried so that the amount of organic solvent remaining in the photosensitive layer 3 is, for example, 2 mass% or less, and specifically, for example, at 70 to 150°C for about 5 to 30 minutes.
  • the photosensitive element may further include an intermediate layer between the support 2 and the photosensitive layer 3.
  • the intermediate layer may be a layer containing a water-soluble resin.
  • An example of the water-soluble resin is a resin containing polyvinyl alcohol as a main component.
  • the photosensitive element may not include a protective layer, and may further include other layers, such as a cushion layer, an adhesive layer, a light absorbing layer, a gas barrier layer, etc.
  • the photosensitive element 1 may be, for example, in the form of a sheet, or may be in the form of a photosensitive element roll wound around a core. In the photosensitive element roll, the photosensitive element 1 is preferably wound with the support 2 on the outside.
  • the core is formed of, for example, polyethylene, polypropylene, polystyrene, polyvinyl chloride, acrylonitrile-butadiene-styrene copolymer, or the like.
  • An end separator may be provided on the end surface of the photosensitive element roll from the viewpoint of end surface protection, and a moisture-proof end surface separator may be provided from the viewpoint of edge fusion resistance.
  • the photosensitive element 1 may be wrapped, for example, in a black sheet with low moisture permeability.
  • the photosensitive element 1 can be suitably used to form a resist pattern, and can be particularly suitably used in the method for manufacturing a printed wiring board described below.
  • the method for forming a resist pattern of this embodiment includes a step of forming a photosensitive layer on a substrate using the photosensitive element (photosensitive layer forming step), a step of irradiating at least a part (predetermined part) of the photosensitive layer with active light rays to form a photocured part (exposure step), and a step of removing at least a part of the uncured part from the substrate (development step), and may include other steps as necessary.
  • the resist pattern can be said to be a photocured product pattern of a photosensitive resin composition or a relief pattern.
  • the method for forming a resist pattern can also be said to be a method for manufacturing a substrate with a resist pattern.
  • the protective layer may be removed from the photosensitive element, and then the photosensitive layer of the photosensitive element may be pressed onto the substrate while being heated.
  • a photosensitive element is used, a laminate consisting of a substrate, a photosensitive layer, and a support, which are laminated in order, is obtained.
  • the substrate is not particularly limited, but is usually a circuit-forming substrate having an insulating layer and a conductor layer formed on the insulating layer, or a die pad (substrate for lead frame) such as an alloy substrate.
  • the photosensitive layer forming step is preferably performed under reduced pressure.
  • the photosensitive layer and/or the substrate may be heated at a temperature of 70 to 130° C. during pressure bonding.
  • the pressure bonding may be performed at a pressure of about 0.1 to 1.0 MPa (about 1 to 10 kgf/cm 2 ), and these conditions are appropriately selected as necessary. If the photosensitive layer is heated to 70 to 130° C., it is not necessary to preheat the substrate in advance, but the substrate may be preheated in order to further improve adhesion and followability.
  • the exposure step at least a part of the photosensitive layer formed on the substrate is irradiated with active light rays, whereby the part irradiated with the active light rays is photocured to form a latent image.
  • the active light rays can be irradiated through the support, but if the support is light-shielding, the support is removed before the photosensitive layer is irradiated with the active light rays.
  • Examples of exposure methods include a method of irradiating active light rays in an image-wise manner through a negative or positive mask pattern called artwork (mask exposure method).
  • a method of irradiating active light rays in an image-wise manner by a projection exposure method may also be used.
  • a method of irradiating active light rays in an image-wise manner by a direct imaging exposure method such as LDI (Laser Direct Imaging) exposure method or DLP (Digital Light Processing) exposure method may also be used.
  • the light source for the actinic rays can be any known light source, including, for example, carbon arc lamps, mercury vapor arc lamps, high pressure mercury lamps, xenon lamps, gas lasers such as argon lasers, solid-state lasers such as YAG lasers, and semiconductor lasers that effectively emit ultraviolet light and visible light.
  • (Developing process) In the development process, at least a part of the uncured portion (other than the photocured portion) of the photosensitive layer is removed from the substrate, thereby forming a resist pattern on the substrate. If a support is present on the photosensitive layer, the support is removed, and then the area other than the photocured portion (also called the unexposed portion) is removed (developed).
  • development methods wet development and dry development, and wet development is widely used.
  • a developer suitable for the photosensitive resin composition is used and development is carried out by a known development method.
  • development methods include the dip method, paddle method, spray method, brushing, scrubbing, and rocking immersion. From the viewpoint of improving resolution, a high-pressure spray method may be used as a development method. Development may be carried out by combining two or more of these methods.
  • the composition of the developer is appropriately selected depending on the composition of the photosensitive resin composition.
  • the developer include an alkaline aqueous solution and an organic solvent developer.
  • an alkaline aqueous solution may be used as the developer.
  • bases for alkaline aqueous solutions include alkali hydroxides such as lithium, sodium, or potassium hydroxide; alkali carbonates such as lithium, sodium, potassium, or ammonium carbonates or bicarbonates; alkali metal phosphates such as potassium phosphate and sodium phosphate; alkali metal pyrophosphates such as sodium pyrophosphate and potassium pyrophosphate; borax, sodium metasilicate, tetramethylammonium hydroxide, ethanolamine, ethylenediamine, diethylenetriamine, 2-amino-2-hydroxymethyl-1,3-propanediol, 1,3-diaminopropanol-2, and morpholine.
  • the alkaline aqueous solution used for development may be a dilute solution of 0.1 to 5% by mass sodium carbonate, a dilute solution of 0.1 to 5% by mass potassium carbonate, a dilute solution of 0.1 to 5% by mass sodium hydroxide, or a dilute solution of 0.1 to 5% by mass sodium tetraborate.
  • the pH of the alkaline aqueous solution may be in the range of 9 to 11, and the temperature can be adjusted according to the alkaline developability of the photosensitive layer.
  • a surfactant, an antifoaming agent, or a small amount of an organic solvent to promote development may be mixed into the alkaline aqueous solution.
  • organic solvents used in alkaline aqueous solutions include acetone, ethyl acetate, alkoxyethanols with an alkoxy group having 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monobutyl ether.
  • organic solvents used in organic solvent developers include 1,1,1-trichloroethane, N-methyl-2-pyrrolidone, N,N-dimethylformamide, cyclohexanone, methyl isobutyl ketone, and ⁇ -butyrolactone.
  • water may be added to these organic solvents in a range of 1 to 20% by weight to form an organic solvent developer.
  • the method for forming a resist pattern in this embodiment may include a step of further curing the resist pattern by heating at about 60 to 250° C. or exposing to light at about 0.2 to 10 J/cm 2 , as necessary, after removing the uncured portions in the development step.
  • the method for manufacturing a printed wiring board of this embodiment includes a step of forming a conductor pattern by etching or plating a substrate on which a resist pattern has been formed using the above-mentioned resist pattern forming method, and may also include other steps, such as a resist pattern removal step, as necessary.
  • the conductor layer provided on the substrate is plated using the resist pattern formed on the substrate as a mask.
  • the resist is removed by removing the resist pattern as described below, and the conductor layer covered by the resist may be etched to form a conductor pattern.
  • the plating method may be electrolytic plating or electroless plating, or may be electroless plating.
  • the resist pattern formed on the substrate is used as a mask to etch away the conductive layer provided on the substrate, forming a conductive pattern.
  • the etching method is appropriately selected depending on the conductive layer to be removed. Examples of etching solutions include cupric chloride solution, ferric chloride solution, alkaline etching solution, and hydrogen peroxide-based etching solution.
  • the resist pattern on the substrate may be removed.
  • the resist pattern can be removed, for example, by stripping with an aqueous solution that is more strongly alkaline than the aqueous solution used in the development process.
  • the aqueous solution that can be used are a 1 to 10% by mass sodium hydroxide aqueous solution, a 1 to 10% by mass potassium hydroxide aqueous solution, etc.
  • the conductor layer covered by the resist can be etched by etching to form a conductor pattern, thereby producing the desired printed wiring board.
  • the method of etching in this case is appropriately selected depending on the conductor layer to be removed.
  • the etching solution described above can be used.
  • the method for manufacturing a printed wiring board according to this embodiment can be applied to the manufacture of not only single-layer printed wiring boards, but also multi-layer printed wiring boards, and can also be applied to the manufacture of printed wiring boards with small-diameter through holes.
  • acrylic acid (AA) methacrylic acid (MAA), styrene (ST), and dicyclopentanyl methacrylate (TCDMA) were prepared, and solutions of binder polymers (A-1) to (A-7) shown in Table 1 were prepared by the following procedure.
  • the binder polymer solution was dissolved in tetrahydrofuran (THF) to prepare a 0.2 mass% THF solution.
  • Mw was measured by gel permeation chromatography (GPC) and calculated using a calibration curve of standard polystyrene. The GPC conditions are shown below.
  • Measuring device Showdex GPC-101 (manufactured by Resonac Co., Ltd.) Detector: Differential refractometer Shodex RI-71S (manufactured by Resonac Co., Ltd.) Column: Shodex LF-804 + LF-804 (manufactured by Resonac Co., Ltd.) Column temperature: 40°C Eluent: tetrahydrofuran (THF) Flow rate: 1 mL/min
  • the acid value of the binder polymer was measured by neutralization titration method in accordance with JIS K6901:2008 5.3.2.
  • Photosensitive resin compositions of the examples and comparative examples were prepared by mixing each component in the blending amount (parts by mass) shown in Table 2 with respect to a binder polymer solution having a solid content of 57 parts by mass. Details of each component shown in Table 2 are as follows.
  • FA-024M PO-EO-PO modified dimethacrylate (manufactured by Resonac Corporation, number of EO groups: 6 (average value), number of PO groups: 12 (average value))
  • BP-2EM Ethoxylated bisphenol A dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., number of EO groups: 2.6 (average value))
  • B-CIM 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (manufactured by Hodogaya Chemical Co., Ltd.)
  • Photosensitive element A polyethylene terephthalate film having a thickness of 16 ⁇ m (manufactured by Toray Industries, Inc., product name "FS-31”) was prepared as a support. The photosensitive resin composition was applied onto the support and then dried for 10 minutes in a hot air convection dryer at 90° C. to form a photosensitive layer having a thickness shown in Table 3. Subsequently, a polyethylene film (manufactured by Tamapoly Corporation, product name "NF-15A”) was laminated as a protective layer on the photosensitive layer to obtain a photosensitive element in which the support, photosensitive layer, and protective layer were laminated in this order.
  • NF-15A polyethylene film
  • a substrate formed by copper sputtering on a silicon wafer was heated to 80°C, and a photosensitive element was laminated (stacked) on the copper surface of the substrate.
  • the lamination was performed using a heat roll at 110°C, with the photosensitive layer of the photosensitive element in contact with the copper surface of the copper substrate while peeling off the protective layer, at a pressure of 0.4 MPa and a roll speed of 1.0 m/min. This resulted in a laminate in which the substrate, photosensitive layer, and support were stacked in this order.
  • the resulting laminate was used as a test piece for the following test.
  • the support was peeled off from the test piece to expose the photosensitive layer, and a 1% by mass aqueous solution of sodium carbonate at 30° C. was sprayed onto the exposed surface. The time required for the photosensitive layer to be completely removed was measured and taken as the minimum development time.
  • sensitivity After placing a Hitachi 41-step step tablet on the support of the laminate, the photosensitive layer was exposed through the support using a projection exposure apparatus (manufactured by Ushio Inc., product name "UX-44101SM”) with an ultra-high pressure mercury lamp ( 365 nm) as the light source, at an exposure amount (amount of irradiation energy) that resulted in 12 remaining steps on the Hitachi 41-step step tablet.
  • the sensitivity (photosensitivity) was evaluated based on the exposure amount (unit: mJ/cm 2 ) at this time. A smaller exposure amount means higher sensitivity.
  • a glass chrome type phototool (resolution negative: having a wiring pattern of line width/space width of x/x (x: 1 to 10, unit: ⁇ m)) was used as a negative for evaluating resolution on the support of the test piece, and the photosensitive layer was exposed with a predetermined energy amount using a projection exposure apparatus (Canon Inc., product name "FPA-3000iW”) with an ultra-high pressure mercury lamp (365 nm) as a light source. After exposure, the support was peeled off to expose the photosensitive layer, and a 1 mass % sodium carbonate aqueous solution at 30° C. was sprayed for a time twice the minimum developing time to remove the unexposed portions (development treatment).
  • the photosensitive elements of Examples 1 to 5 had improved developability and resolution, and were able to form fine resist patterns.
  • the photosensitive element of Comparative Example 1 did not have sufficient resolution, and the photosensitive elements of Comparative Examples 2 to 4 required a long time for development, and were unable to form fine resist patterns.

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PCT/JP2023/039303 2023-10-31 2023-10-31 感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法 Pending WO2025094282A1 (ja)

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EP23957610.1A EP4675350A1 (en) 2023-10-31 2023-10-31 Photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board
PCT/JP2023/039303 WO2025094282A1 (ja) 2023-10-31 2023-10-31 感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法
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CN202380096538.4A CN120981769A (zh) 2023-10-31 2023-10-31 感光性元件、抗蚀剂图案的形成方法及印刷线路板的制造方法

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JP2013195712A (ja) 2012-03-19 2013-09-30 Hitachi Chemical Co Ltd 感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JP2014010382A (ja) * 2012-07-02 2014-01-20 Fujifilm Corp 感光性転写材料、硬化膜およびその製造方法、有機ｅｌ表示装置、液晶表示装置並びに静電容量型入力装置
WO2021221025A1 (ja) * 2020-04-30 2021-11-04 富士フイルム株式会社 構造体の製造方法、及び、構造体
JP2023097347A (ja) * 2021-12-27 2023-07-07 富士フイルム株式会社 蒸着マスクの製造方法
JP2023097008A (ja) * 2021-12-27 2023-07-07 富士フイルム株式会社 蒸着マスク製造用感光性転写材料、及び、蒸着マスクの製造方法

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JP2013195712A (ja) 2012-03-19 2013-09-30 Hitachi Chemical Co Ltd 感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JP2014010382A (ja) * 2012-07-02 2014-01-20 Fujifilm Corp 感光性転写材料、硬化膜およびその製造方法、有機ｅｌ表示装置、液晶表示装置並びに静電容量型入力装置
WO2021221025A1 (ja) * 2020-04-30 2021-11-04 富士フイルム株式会社 構造体の製造方法、及び、構造体
JP2023097347A (ja) * 2021-12-27 2023-07-07 富士フイルム株式会社 蒸着マスクの製造方法
JP2023097008A (ja) * 2021-12-27 2023-07-07 富士フイルム株式会社 蒸着マスク製造用感光性転写材料、及び、蒸着マスクの製造方法

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