WO2020017187A1 - Composition photosensible, filtre coupant la lumière infrarouge, et dispositif d'imagerie à semi-conducteurs - Google Patents

Composition photosensible, filtre coupant la lumière infrarouge, et dispositif d'imagerie à semi-conducteurs Download PDF

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Publication number
WO2020017187A1
WO2020017187A1 PCT/JP2019/022921 JP2019022921W WO2020017187A1 WO 2020017187 A1 WO2020017187 A1 WO 2020017187A1 JP 2019022921 W JP2019022921 W JP 2019022921W WO 2020017187 A1 WO2020017187 A1 WO 2020017187A1
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photosensitive composition
compound
group
mass
infrared light
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PCT/JP2019/022921
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English (en)
Japanese (ja)
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峻輔 北島
貴規 田口
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富士フイルム株式会社
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Priority to JP2020530933A priority Critical patent/JP7086193B2/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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
    • H01L27/144—Devices controlled by radiation
    • H01L27/146—Imager structures

Definitions

  • the present invention relates to a photosensitive composition, an infrared light cut filter, and a solid-state imaging device.
  • a solid-state imaging device for a color image is used in a video camera, a digital still camera, a mobile phone with a camera function, and the like. These solid-state imaging devices use silicon photodiodes that are sensitive to infrared light (infrared light) in their light-receiving parts, so it is necessary to perform visibility correction, and use infrared light cut filters. There are many.
  • Patent Document 1 discloses a photosensitive composition containing a predetermined tungsten oxide and / or a composite tungsten oxide as a composition for forming an infrared light cut filter.
  • the cross-sectional shape of the pattern be excellent in rectangularity. Further, it is required that the cured film formed using the photosensitive composition hardly change in transmittance even after being subjected to the heat treatment. In particular, even when various color filters and the cured film are arranged adjacent to each other, it is desirable that the transmittance does not easily change after the heat treatment.
  • the fact that the transmittance hardly changes after the heat treatment is referred to as being excellent in heat resistance.
  • the present inventors evaluated the above characteristics using the photosensitive composition described in Patent Document 1, and could not satisfy both characteristics in a well-balanced manner.
  • an object of the present invention is to provide a photosensitive composition which can form a pattern having excellent rectangularity in cross-sectional shape and can form a cured film having excellent heat resistance.
  • Another object of the present invention is to provide an infrared light cut filter formed using a photosensitive composition and a solid-state imaging device including the infrared light cut filter.
  • a photosensitive composition comprising metal-containing tungsten oxide particles, a polymerizable compound, a polymerization initiator, an ultraviolet absorber, and a polymerization inhibitor, A photosensitive composition, wherein the mass ratio of the content of the ultraviolet absorber to the content of the polymerization inhibitor is 0.08 to 330.
  • the photosensitive composition according to (1) wherein the surface of the metal-containing tungsten oxide particles is coated with a metal oxide.
  • the metal oxide is an oxide containing at least one or more elements selected from the group consisting of Si, Ti, Zr, and Al.
  • the ultraviolet absorber is a UV absorber having a mass reduction rate at 150 ° C.
  • the photosensitive composition according to any one of (3).
  • the polymerization inhibitor is at least two or more selected from the group consisting of a hindered phenol compound, a phenol compound other than the hindered phenol compound, a benzoquinone compound, and a hydroquinone compound.
  • the polymerization inhibitor is one or more first polymerization inhibitors selected from the group consisting of a hindered phenol compound, a benzoquinone compound, and a hydroquinone compound, and a phenol compound other than the hindered phenol compound.
  • the photosensitive composition according to (7) comprising a compound.
  • the photosensitive composition according to (8) wherein the mass ratio of the content of the phenolic compound other than the hindered phenolic compound to the total content of the first polymerization inhibitor is 0.0009 to 0.17. object.
  • (12) A solid-state imaging device including the infrared light cut filter according to (11).
  • the photosensitive composition which can form the pattern excellent in the rectangular shape of a cross-sectional shape and can form the cured film excellent in heat resistance can be provided. Further, according to the present invention, an infrared cut filter formed using the photosensitive composition and a solid-state imaging device including the infrared cut filter can be provided.
  • FIG. 1 is a schematic sectional view illustrating a configuration of an embodiment of a solid-state imaging device of the present invention.
  • FIG. 2 is a functional block diagram of an imaging device to which the solid-state imaging device of the present invention is applied. It is a figure for explaining pattern rectangularity evaluation.
  • the notation not indicating substituted or unsubstituted includes not only a group having no substituent but also a group having a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • “to” is used to mean that the numerical values described before and after it are included as the lower limit and the upper limit.
  • (meth) acrylate represents acrylate and methacrylate
  • (meth) acryl represents acryl and methacryl
  • (meth) acryloyl represents acryloyl and methacryloyl.
  • “monomer” and “monomer” have the same meaning. Monomers are compounds distinguished from oligomers and polymers and have a weight average molecular weight of 2,000 or less.
  • a polymerizable compound refers to a compound having a polymerizable functional group, and may be a monomer or a polymer.
  • the polymerizable functional group refers to a group that participates in a polymerization reaction.
  • the total solid content refers to the total mass of components excluding the solvent from the total composition of the composition.
  • the solid content in the present invention is a solid content at 25 ° C.
  • the feature of the present invention is that the mass ratio between the ultraviolet absorber and the polymerization inhibitor is adjusted. It has been found that by adjusting the mass ratio to a predetermined range, heat resistance and pattern rectangularity (rectangularity of a pattern to be formed) can be achieved in a better balance.
  • the photosensitive composition contains metal-containing tungsten oxide particles, a polymerizable compound, a polymerization initiator, an ultraviolet absorber, and a polymerization inhibitor.
  • a photosensitive composition also simply referred to as “composition”.
  • the metal-containing tungsten oxide particles are tungsten oxide particles containing metal atoms.
  • the specific particles have an effect as an infrared absorber because they selectively block infrared light (light having a wavelength of about 800 to 1200 nm) depending on the crystal structure. Therefore, the infrared light cut filter including the specific particles has a high light-shielding property in an infrared region and a high light-transmitting property in a visible light region.
  • the specific particles have a small absorption of light having a shorter wavelength than the visible region used for exposure, such as a high-pressure mercury lamp, KrF, and ArF used for image formation. Therefore, as described later, the photosensitive composition of the present invention has excellent pattern formability, and can finely control the shape of the infrared light cut filter.
  • the type of the metal atom contained in the specific particles is not particularly limited, but an alkali metal may be mentioned in that it is more excellent in shielding infrared light.
  • the specific particles are preferably represented by the following general formula (composition formula) (I).
  • Composition formula) (I) M x W y O z (I) M represents an alkali metal, W represents tungsten, and O represents oxygen. 0.001 ⁇ x / y ⁇ 1.1 2.2 ⁇ z / y ⁇ 3.0
  • the alkali metal of M may be one kind or two or more kinds.
  • Rb or Cs is preferable, and Cs is more preferable.
  • x / y is 0.001 or more, infrared light can be sufficiently shielded, and when x / y is 1.1 or less, generation of an impurity phase in specific particles can be further avoided.
  • z / y is 2.2 or more, chemical stability as a material can be further improved, and when it is 3.0 or less, infrared light can be further shielded.
  • Specific examples of the specific particles containing an alkali metal represented by the general formula (I) include Cs 0.33 WO 3 , Rb 0.33 WO 3 , K 0.33 WO 3, and the like. Cs 0.33 WO 3 or Rb 0.33 WO 3 is preferable, and Cs 0.33 WO 3 is more preferable.
  • the surface of the metal-containing tungsten oxide particles is preferably coated with a metal oxide in that the effect of the present invention is more excellent. That is, the photosensitive composition is preferably coated particles containing metal-containing tungsten oxide particles and metal oxide disposed so as to cover the surfaces of the metal-containing tungsten oxide particles.
  • the type of metal oxide is not particularly limited, and is preferably an oxide containing at least one or more elements selected from the group consisting of Si, Ti, Zr, and Al.
  • the metal oxide may be disposed so as to cover the entire surface of the metal-containing tungsten oxide particles, or may be disposed so as to cover a part thereof.
  • the average particle size of the specific particles is not particularly limited, but is preferably 800 nm or less, more preferably 400 nm or less, and further preferably 200 nm or less.
  • the average particle diameter is in the above range, the specific particles are less likely to block visible light due to light scattering, and thus the light transmittance in the visible light region is more excellent.
  • the average particle diameter is preferably as small as possible.
  • the average particle diameter of the specific particles is preferably 1 nm or more from the viewpoint of easy handling during production.
  • a known electron microscope measures the particle diameter (diameter) of at least 50 specific particles and arithmetically averages them.
  • the specific particle is not a perfect circle, the long diameter is measured as the particle diameter.
  • the content of the specific particles in the photosensitive composition is not particularly limited, but is preferably from 1 to 20% by mass, and more preferably from 3 to 15%, based on the total mass of the photosensitive composition from the viewpoint of more excellent infrared light shielding properties. % Is more preferred.
  • two or more specific particles can be used, and in that case, the total content is preferably in the above range.
  • the specific particles are commercially available, but can be obtained by a method of heat-treating a tungsten compound containing an alkali metal in an inert gas atmosphere or a reducing gas atmosphere (see Japanese Patent No. 4096205). Further, for example, it is also available as a dispersion of tungsten oxide fine particles containing an alkali metal such as YMF-02A, YMS-01A-2, and YMF-10A-1 manufactured by Sumitomo Metal Mining Co., Ltd.
  • any compound may be used as long as it has a polymerizable group (a group that reacts by at least one of an acid, a radical, and heat) in the molecule. Is preferred.
  • the polymerizable compound having a polymerizable group that reacts with at least one of an acid, a radical, and heat include an unsaturated ester functional group (for example, an acryloyl group and a methacryloyl group), an unsaturated amide group, a vinyl ether group, And an ethylenically unsaturated group-containing compound having an ethylenically unsaturated group such as an allyl group; a methylol compound; a bismaleimide compound; a benzocyclobutene compound; a bisallylnadiimide compound; a benzoxazine compound.
  • the polymerizable compound may be a monomer or a polymer.
  • a radical polymerizable compound is preferable, and a compound having an ethylenically unsaturated double bond is more preferable.
  • the polymerizable compound include unsaturated carboxylic acids (eg, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, and maleic acid), esters thereof, and amides thereof.
  • Carboxylic acid esters, esters of unsaturated carboxylic acids with aliphatic polyhydric alcohol compounds, or amides of unsaturated carboxylic acids with aliphatic polyamine compounds are preferred.
  • an ester of an unsaturated carboxylic acid and an aliphatic polyhydric alcohol compound can exhibit high hydrophobicity in an exposed portion, so that it is easy to form a pattern having a desired shape by alkali development, and a highly durable pattern.
  • the polymerizable compound include a hydroxyl group, an amino group, and an addition reaction product of an unsaturated carboxylic acid ester or amide having a nucleophilic substituent such as a mercapto group with a monofunctional or polyfunctional isocyanate or epoxy.
  • examples of the polymerizable compound include a dehydration condensation product of the unsaturated carboxylic acid ester or amide and a monofunctional or polyfunctional carboxylic acid.
  • unsaturated carboxylic esters examples include methacrylic esters, itaconic esters, crotonic esters, isocrotonic esters, and maleic esters.
  • a urethane-based addition-polymerizable compound produced by an addition reaction between an isocyanate and a hydroxyl group is also suitable, and specific examples thereof are described in, for example, JP-B-48-41708.
  • the number of ethylenically unsaturated double bonds in the radical polymerizable compound is not particularly limited, and is preferably 2 or more, more preferably 3 or more, and still more preferably 4 or more from the viewpoint of curing sensitivity.
  • the upper limit is not particularly limited, but is often 10 or less.
  • the polymerizable compound is preferably a polymerizable compound containing a modified EO (ethylene oxide). Further, from the viewpoints of curing sensitivity and exposed part strength, a compound containing a urethane bond is preferable as the polymerizable compound. Further, from the viewpoint of developability during pattern formation, a compound having an acid group is preferable as the polymerizable compound.
  • polymerizable compound examples include bisphenol A diacrylate, modified bisphenol A diacrylate EO, trimethylolpropane triacrylate, trimethylolpropane tri (acryloyloxypropyl) ether, trimethylol ethane triacrylate, tetraethylene glycol diacrylate, and pentaerythritol.
  • Diacrylate pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, tri (acryloyl) Oh Shiechiru) isocyanurate, pentaerythritol tetraacrylate EO-modified product, dipentaerythritol hexaacrylate EO-modified product, and, like tricyclodecane dimethanol diacrylate.
  • modified bisphenol A diacrylate EO modified pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, tri (acryloyloxyethyl) isocyanurate, modified pentaerythritol tetraacrylate, Alternatively, a modified dipentaerythritol hexaacrylate EO is preferable.
  • urethane oligomers UAS-10, UAB-140 (all manufactured by Sanyo Kokusaku Pulp Co., Ltd.), KAYARAD RP-1040, DPHA-40H, KAYARAD RP-1040, KAYARAD DPHA, KAYARAD DPCA-20 (more than UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, DCP-A (all manufactured by Kyoeisha Chemical Co., Ltd.), NK Ester A-BPE- 20, A-DCP, NK ester A-TMMT, NK ester A-DPH-12E (all manufactured by Shin-Nakamura Chemical Co., Ltd.), TO-756, TO-1382, M-305, Aronix M-510 (all manufactured by TOA Synthetic Co., Ltd.) and Ogzol EA-0300 (Osaka Gas Chemical Co., Ltd.) Can be
  • the content of the polymerizable compound in the photosensitive composition is not particularly limited, but is preferably 1 to 20% by mass relative to the total mass of the photosensitive composition in that the strength of the infrared cut filter is more excellent. -10% by mass is more preferred.
  • the polymerizable compound may be used alone or in combination of two or more. Above all, it is preferable to use two or more kinds in combination in that the pattern rectangularity is more excellent.
  • Polymerization initiator examples include a photopolymerization initiator and a thermal polymerization initiator, and a photopolymerization initiator is preferable.
  • the photopolymerization initiator is a compound having a capability of initiating polymerization upon exposure to light, and preferably has photosensitivity from an ultraviolet light region to a visible light region.
  • the thermal polymerization initiator is a compound having the ability to initiate polymerization by heat, and is preferably an initiator that decomposes at 150 to 250 ° C.
  • a compound having at least an aromatic group is preferable.
  • acylphosphine compounds, acetophenone compounds, ⁇ -aminoketone compounds, benzophenone compounds, benzoin ether compounds, thioxanthone compounds, oxime compounds, hexaarylbiimidazole compounds, trihalo compounds examples include methyl compounds, azo compounds, organic peroxides, diazonium compounds, iodonium compounds, sulfonium compounds, azinium compounds, benzoin ether compounds, ketal derivative compounds, onium salt compounds, organic boron salt compounds, and disulfone compounds.
  • an oxime compound a hydroxyacetophenone compound, an aminoacetophenone compound, an acylphosphine compound, an ⁇ -aminoketone compound, a trihalomethyl compound, a hexaarylbiimidazole compound, or a thiol compound is preferable, and an oxime compound is more preferable.
  • the hydroxyacetophenone compound include IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, and IRGACURE-127 (all trade names: manufactured by BASF).
  • aminoacetophenone compound examples include IRGACURE-907, IRGACURE-369, and IRGACURE-379 (trade names: all manufactured by BASF).
  • acylphosphine compound examples include IRGACURE-819 and DAROCUR-TPO (trade names: both manufactured by BASF).
  • Examples of the oxime compound include IRGACURE OXE 01 (1.2-octanedione, 1- [4- (phenylthio)-, 2- (o-benzoyloxime)]) and IRGACURE OXE 02 (ethanone, 1- [9- Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (o-acetyloxime)), IRGACUREOXE03 (trade name, manufactured by BASF) and IRGACUREOXE04 (trade name, manufactured by BASF). No.
  • Examples of the oxime compound include the formulas (OX-1), (OX-2) and (OX-2) described in paragraph 0513 of JP-A-2012-208494 ( ⁇ 0632> of the corresponding US Patent Application Publication No. 2012/235099).
  • the description of the compound represented by OX-3) can be referred to, and the contents thereof are incorporated in the present specification.
  • oxime compound examples include polymerization initiators described in paragraphs 0092 to 0096 of JP-A-2012-113104, the contents of which are incorporated herein.
  • Commercially available oxime compounds include TRONLY TR-PBG-304, TRONLY TR-PBG-309, and TRONLY TR-PBG-305 (CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO., LTD. )).
  • the content of the polymerization initiator in the photosensitive composition is not particularly limited, but is preferably from 0.1 to 10% by mass, more preferably from 0.5 to 10% by mass, based on the total mass of the photosensitive composition, from the viewpoint of excellent drying resistance. 5.0 mass% is more preferable.
  • One type of polymerization initiator may be used alone, or two or more types may be used in combination.
  • polymerization inhibitor examples include known polymerization inhibitors. It is presumed that the polymerization inhibitor has a function of capturing radicals generated when a color filter disposed adjacent to the cured layer is subjected to heat treatment.
  • a phenol compound, a hindered amine compound, a phosphorus compound, and a phenothiazine compound can be given.
  • a hindered phenol compound, a phenol compound other than the hindered phenol compound, a benzoquinone compound, or a hydroquinone compound is preferable in that the effects of the present invention are more excellent.
  • the hindered phenol compound is a phenol compound having a substituent other than a hydrogen atom at at least one of the two ortho positions of the phenolic hydroxyl group.
  • substituents include an alkyl group (preferably an alkyl group other than a methyl group), an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group, a substituted amino group, and a thioalkyl Group, thiophenyl group, and halogen atom
  • a compound represented by the formula (X) is preferable.
  • R 1 and R 2 each independently represent a substituent.
  • the definition of the substituent is as described above, and among them, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group is preferable, and an alkyl group having 4 or more carbon atoms is more preferable.
  • R 3 represents a substituent.
  • the definition of the substituent is as described above, and among them, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group is preferable, and an alkyl group is preferable.
  • n is 2 or more, a plurality of R 3 may be the same or different.
  • n represents an integer of 0 to 3. Especially, 1 is preferable.
  • a compound represented by the formula (Y) is preferable.
  • R 4 represents a substituent.
  • the definition of the substituent is as described above, and among them, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkoxy group is preferable, and an alkoxy group is more preferable.
  • m represents an integer of 0 to 3. Especially, 1 is preferable.
  • R 5 to R 8 each independently represent a hydrogen atom or a substituent.
  • the definition of the substituent is as described above, and among them, an aryl group, an amino group, a substituted amino group, or a halogen atom is preferable.
  • Examples of the benzoquinone-based compound include ortho-benzoquinone and para-benzoquinone.
  • hydroquinone-based compound a compound represented by the formula (V) is preferable.
  • R 9 represents a substituent.
  • the definition of the substituent is as described above, and among them, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or an alkoxy group is preferable, and an alkyl group is more preferable.
  • p is 2 or more, a plurality of R 9 may be the same or different.
  • p represents an integer of 0 to 4. Especially, 1 is preferable.
  • the polymerization inhibitors may be used alone or in combination of two or more.
  • the photosensitive composition preferably contains two or more polymerization inhibitors from the viewpoint that the effects of the present invention are more excellent.
  • the polymerization inhibitor comprises a hindered phenol compound, a phenol compound other than the hindered phenol compound, a benzoquinone compound, and a hydroquinone compound. It is preferable that at least two kinds selected from the group be used.
  • the polymerization inhibitor comprises one or more first polymerization inhibitors selected from the group consisting of a hindered phenol compound, a benzoquinone compound, and a hydroquinone compound; It is preferable to include a phenol compound other than the phenol compound. Further, the mass ratio of the content of the phenolic compound other than the hindered phenolic compound to the total content of the first polymerization inhibitor is not particularly limited, but from the viewpoint that the effect of the present invention is more excellent, 0.0009 to 0. .17.
  • the content of the polymerization inhibitor in the photosensitive composition is not particularly limited, but is preferably 0.0001 to 0.30% by mass based on the total mass of the photosensitive composition, in that the effect of the present invention is more excellent. 0.002 to 0.20% by mass is more preferable.
  • UV absorber refers to an agent that does not have a function of initiating polymerization of a polymerizable compound by light or heat (that is, does not correspond to a polymerization initiator).
  • “has no function of initiating the polymerization of the polymerizable compound” substantially, the ultraviolet absorber, even when receiving the energy of light or heat, for starting the polymerization of the polymerizable compound No active species are generated.
  • the ultraviolet absorber not only has no function of initiating the polymerization of the polymerizable compound but also does not have the characteristics of a sensitizer described later.
  • the property of the sensitizer means a property of starting polymerization by transferring energy obtained by absorbing light to another substance (eg, a polymerization initiator).
  • the ultraviolet absorber preferably has a maximum absorption wavelength in a wavelength range of 300 to 430 nm, and more preferably has a maximum absorption wavelength in a wavelength range of 330 to 420 nm.
  • the ultraviolet absorber has a maximum absorption wavelength in at least one of (I) a range of 340 to 380 nm, (II) a range of 380 to 420 nm, and (III) a range of 420 to 450 nm. It is more preferred to have.
  • the mass reduction rate at 150 ° C. is preferably 5% or less, more preferably 3% or less.
  • the lower limit is not particularly limited, but 0% is mentioned.
  • the mass reduction rate at 150 ° C. is within the above range, the ultraviolet absorbent is hardly decomposed at the time of exposure to be described later, and easily functions as an ultraviolet absorbent.
  • the mass reduction rate at 220 ° C. is preferably 40% or more, more preferably more than 40%, and even more preferably 70% or more.
  • the upper limit is not particularly limited, but 100% may be mentioned.
  • the conditions for measuring the thermal mass of the ultraviolet absorbent are as follows. That is, in a nitrogen gas atmosphere, the temperature of the ultraviolet absorber is raised from 25 ° C. to 100 ° C. at a rate of 10 ° C./min. After holding at 100 ° C. for 30 minutes, the temperature of the ultraviolet absorbent is increased to 220 ° C. at a rate of 10 ° C./min, and the temperature is maintained at 220 ° C. for 30 minutes. The average value of the mass of the ultraviolet absorber for 24 to 29 minutes from the start of holding when the ultraviolet absorber is held at 100 ° C.
  • the type of the ultraviolet absorber is not particularly limited, and examples thereof include a dibenzoylmethane compound, an aminobutadiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, a substituted acrylonitrile compound, and a triazi compound. Among them, a dibenzoylmethane-based compound or an aminobutadiene-based compound is preferable.
  • dibenzoylmethane-based compound examples include 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, and 2,4.
  • salicylate-based ultraviolet absorber examples include phenyl salicylate, p-octylphenyl salicylate, and pt-butylphenyl salicylate.
  • Benzophenone-based compounds include 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2 ', 4,4'- Examples include tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, and 2-hydroxy-4-octoxybenzophenone.
  • benzotriazole-based ultraviolet absorber examples include 2- (2′-hydroxy-3 ′, 5′-di-tert-butylphenyl) -5-chlorobenzotriazole and 2- (2′-hydroxy -3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-tert-amyl-5'-isobutylphenyl) -5-chlorobenzotriazole, -(2'-hydroxy-3'-isobutyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-isobutyl-5'-propylphenyl) -5-chlorobenzotriazole 2- (2'-hydroxy-3 ', 5'-di-tert-butylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methyl Phenyl) benzotriazole, and
  • substituted acrylonitrile compound substituted acrylonitrile ultraviolet absorber
  • substituted acrylonitrile ultraviolet absorber examples include ethyl 2-cyano-3,3-diphenylacrylate and 2-ethylhexyl 2-cyano-3,3-diphenylacrylate.
  • triazine-based ultraviolet absorber examples include 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethyl Phenyl) -1,3,5-triazine, 2- [4-[(2-hydroxy-3-tridecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl ) Mono (hydroxyphenyl) triazines such as -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine Compounds: 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2- Droxy-3-methyl-4-propyl) -6- (2,4-
  • a diethylamino-phenylsulfonyl-pentadienoate-based ultraviolet absorber manufactured by FUJIFILM Fine Chemical, trade name: DPO
  • DPO diethylamino-phenylsulfonyl-pentadienoate-based ultraviolet absorber
  • the content of the ultraviolet absorber in the photosensitive composition is not particularly limited, but is preferably 0.01 to 10.0% by mass, and more preferably 0.05 to 1.50% by mass based on the total mass of the photosensitive composition. More preferred.
  • the ultraviolet absorber may be used alone or in combination of two or more.
  • the mass ratio of the content of the ultraviolet absorber to the content of the polymerization inhibitor is from 0.08 to 330, and from 0.1 to 200 in that the effect of the present invention is more excellent. Preferably, 3 to 30 is more preferable. In addition, from the point which is excellent in rectangularity, 20 or more is more preferable.
  • the photosensitive composition may contain components other than the components described above, for example, a resin binder, a sensitizer, a solvent, a surfactant, a dispersant, a crosslinking agent, and a curing accelerator. No. Hereinafter, each component will be described in detail.
  • resin binder examples include (meth) acrylic resin, urethane resin, polyvinyl alcohol, polyvinyl butyral, polyvinyl formal, polyamide, polyester, polyimide, and polybenzoxazole, and (meth) acrylic resin, or And urethane-based resins are preferred. Further, as the resin binder, an alkali-soluble binder (alkali-soluble resin) is also preferable. When the photosensitive composition contains an alkali-soluble binder, and when a coating film obtained from the photosensitive composition is exposed, an unexposed portion can be easily removed with an alkali developing solution.
  • alkali-soluble binder examples include (meth) acrylic resin, urethane resin, polyvinyl alcohol, polyvinyl butyral, polyvinyl formal, polyamide, polyester, polyimide or a precursor thereof, and polybenzoxazole or a precursor thereof.
  • (Meth) acrylic resins or urethane resins are preferred.
  • the polyimide or its precursor and the polybenzoxazole or its precursor include polyimide resins described in paragraphs 0012 to 0046 of WO2011 / 067998 and paragraphs 0020 to 0054 of JP2013050593. And the contents thereof are incorporated in the specification of the present application.
  • the alkali-soluble binder preferably has an acid group.
  • the acid group include a carboxylic acid group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, and a sulfonamide group, and a carboxylic acid group is preferable from the viewpoint of obtaining raw materials.
  • a polymer obtained using a polymerizable compound having an acid group is preferable, and from the viewpoint of adjusting the acid value, the polymerizable compound having an acid group does not have an acid group.
  • a copolymer obtained by copolymerizing with a polymerizable compound is more preferable.
  • Examples of the polymerizable compound having an acid group include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, incrotonic acid, maleic acid, and p-carboxyl styrene, and include acrylic acid, methacrylic acid, or p-carboxylstyrene. -Carboxystyrene is preferred.
  • Examples of the polymerizable compound having no acid group include (meth) acrylic acid esters (such as alkyl esters, aryl esters, and aralkyl esters).
  • the alkyl group in the alkyl ester portion of the (meth) acrylate may be linear or branched, and is preferably an alkyl group having 1 to 10 carbon atoms, and is preferably an alkyl group having 1 to 6 carbon atoms. Groups are more preferred.
  • the aryl group in the aryl ester portion of the (meth) acrylate is preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms.
  • the aralkyl group in the aralkyl ester site of the (meth) acrylate is preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 12 carbon atoms.
  • the content of the acid group in the alkali-soluble binder is not particularly limited, but is preferably from 0.5 to 4.0 meq / g, and more preferably from 0.5 to 3.0 meq / g, from the viewpoint of alkali developability and the strength of the obtained cured film. / G is more preferred.
  • the alkali-soluble binder preferably further has a crosslinkable group.
  • the crosslinkable group is a group that crosslinks the resin binder in the course of a polymerization reaction occurring in the coating film when the coating film obtained from the photosensitive composition is exposed or heated.
  • the crosslinkable group include a polymerizable group (for example, an ethylenically unsaturated bond group as a functional group capable of undergoing an addition polymerization reaction), an amino group, and an epoxy group.
  • the crosslinkable group may be a functional group capable of forming a radical upon irradiation with light, for example, a thiol group and a halogen group. Of these, an ethylenically unsaturated double bond group is preferred as the crosslinkable group.
  • a styryl group, a (meth) acryloyl group, or an allyl group is preferable, and a (meth) acryloyl group is more preferable.
  • the content of the crosslinking group in the alkali-soluble binder is not particularly limited, but is preferably 0.5 to 3.0 meq / g, more preferably 1.0 to 3.0 meq / g, and 1.5 to 2.8 meq / g. / G is particularly preferred.
  • the content (meq / g) can be measured, for example, by iodine value titration.
  • the alkali-soluble binder having a crosslinkable group is described in detail in JP-A-2003-262958, and the compounds described herein can be used in the present invention.
  • a polymer obtained by polymerizing a monomer component containing a compound represented by the following general formula (ED) (hereinafter, also referred to as “ether dimer”). Specific polymer "). If the specific polymer is used, the pattern forming property of the infrared light cut filter is more excellent.
  • R 1 and R 2 each represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • the optionally substituted hydrocarbon group having 1 to 25 carbon atoms represented by R 1 and R 2 include a linear or branched alkyl group; an aryl group; an alicyclic group; An alkyl group substituted with an aryl group such as benzyl; and the like. Among them, a methyl group, an ethyl group, a cyclohexyl group, or a benzyl group is preferable in terms of excellent heat resistance of the substituent.
  • ether dimer examples include specific examples of the ether dimer described in paragraph 0565 of JP-A-2012-208494 (paragraph 0694 of the corresponding US Patent Application Publication No. 2012/235099). The contents are incorporated herein. Among them, dimethyl-2,2 '-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2'-[oxybis (methylene)] bis-2-propenoate, dicyclohexyl-2,2 '-[oxybis (Methylene)] bis-2-propenoate or dibenzyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate is preferred. These ether dimers may be used alone or in combination of two or more. The structure derived from the compound represented by the general formula (ED) may be copolymerized with another monomer.
  • ED general formula
  • the content of the repeating unit derived from the ether dimer in the specific polymer is preferably from 1 to 50 mol%, more preferably from 1 to 20 mol%, based on all repeating units in the alkali-soluble binder.
  • Other monomers may be copolymerized with the ether dimer.
  • a monomer for introducing an acid group for example, a monomer for introducing a radical polymerizable double bond, a monomer for introducing an epoxy group, and these And other copolymerizable monomers.
  • Such a monomer may be used alone or in combination of two or more.
  • Examples of the monomer for introducing an acid group include monomers having a carboxyl group such as (meth) acrylic acid and itaconic acid, monomers having a phenolic hydroxyl group such as N-hydroxyphenylmaleimide, and maleic anhydride. And monomers having a carboxylic anhydride group such as itaconic anhydride. Among them, (meth) acrylic acid is preferred.
  • the monomer for introducing an acid group may be a monomer capable of providing an acid group after polymerization, for example, a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate, Examples include monomers having an epoxy group such as glycidyl (meth) acrylate and monomers having an isocyanate group such as 2-isocyanatoethyl (meth) acrylate.
  • a monomer capable of providing an acid group after polymerization it is necessary to perform a treatment for providing an acid group after polymerization.
  • a treatment for providing an acid group after polymerization for example, if a monomer having a hydroxyl group is used, succinic anhydride, tetrahydrophthalic anhydride, and an acid anhydride of maleic anhydride are added. Processing.
  • the content of the monomer for introducing an acid group is determined by the monomer component. It is preferably from 5 to 70% by mass, more preferably from 10 to 60% by mass, based on the total mass.
  • Examples of the monomer for introducing a radical polymerizable double bond include a monomer having a carboxyl group such as (meth) acrylic acid and itaconic acid; and a carboxylic acid anhydride group such as maleic anhydride and itaconic anhydride.
  • Monomers having an epoxy group such as glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, and o- (or m- or p-) vinylbenzyl glycidyl ether.
  • a treatment for imparting a radical polymerizable double bond after polymerization for example, when a monomer having a carboxyl group is used, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, and , O- (or m-, or p-) vinylbenzyl glycidyl ether and the like, and a compound having an epoxy group and a radical polymerizable double bond.
  • the monomer component for introducing a radical polymerizable double bond contains a monomer for introducing a radical polymerizable double bond
  • the monomer component for introducing a radical polymerizable double bond is The content is preferably from 5 to 70% by mass, more preferably from 10 to 60% by mass, based on the total mass of the monomer components.
  • Examples of monomers for introducing an epoxy group include glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, and o- (or m- or p-) vinylbenzyl glycidyl ether Is mentioned.
  • the monomer component containing the compound represented by the general formula (ED) contains a monomer for introducing an epoxy group
  • the content of the monomer for introducing an epoxy group is determined by the content of the monomer component. It is preferably from 5 to 70% by mass, more preferably from 10 to 60% by mass, based on the total mass.
  • a polymer obtained by polymerizing a monomer component containing a compound represented by the general formula (ED) contains another copolymerizable monomer, its content is not particularly limited, but is preferably 95% by mass. Or less, more preferably 85% by mass or less.
  • the weight average molecular weight of the specific polymer is not particularly limited, it is preferably from 2,000 to 200,000, more preferably from 5,000 to 100,000, still more preferably from 5,000 to 20,000, from the viewpoint of the heat resistance of the coating film formed from the photosensitive composition.
  • the acid value is preferably from 30 to 500 mgKOH / g, more preferably from 50 to 400 mgKOH / g.
  • a polymerization method applied to the synthesis of the specific polymer conventionally known various polymerization methods can be adopted, and a solution polymerization method is preferable. Specifically, for example, according to the method for synthesizing the polymer (a) described in JP-A-2004-300204, a polymer obtained by polymerizing a monomer component containing a compound represented by the general formula (ED) is used. Coalescence can be synthesized.
  • ED general formula
  • composition ratio of the exemplified compounds shown below is mol%.
  • examples of commercially available products include Acrycure RD-F8 (acrylic resin) (manufactured by Nippon Shokubai Co., Ltd.).
  • the content of the resin binder (especially, an alkali-soluble binder) in the photosensitive composition is not particularly limited, but the strength of the infrared light cut filter is more excellent, and the photolithography property and the residue are improved. It is preferably from 5 to 50% by mass, more preferably from 10 to 25% by mass, based on the mass.
  • solvent The type of the solvent is not particularly limited, and includes water and an organic solvent.
  • examples of the solvent include a solvent A having a boiling point of 170 to 200 ° C. at 1 atm.
  • Solvent A has a boiling point of 170 to 200 ° C, preferably 180 to 193 ° C.
  • the solvent A preferably contains three or more oxygen atoms in the molecule, more preferably 3 to 5 oxygen atoms, and still more preferably 3.
  • Preferred examples of the solvent A include a solvent represented by the following formula (X) or formula (Y).
  • Formula (Y) R 1 O— (LO) m —CO—R 2 In the formulas (X) and (Y), R 1 represents a hydrogen atom or an alkyl group. The number of carbon atoms contained in the alkyl group is not particularly limited, but is preferably 1 to 3, and more preferably 1.
  • R 2 represents an alkyl group.
  • the number of carbon atoms contained in the alkyl group is preferably from 1 to 3, and more preferably 1.
  • L represents an alkylene group.
  • the number of carbon atoms contained in the alkylene group is preferably from 3 to 5, and more preferably 3.
  • n represents an integer of 2 to 4.
  • m represents an integer of 1 to 2.
  • the solvent A examples include dipropylene glycol monomethyl ether (boiling point: 188 ° C.), cyclohexanol acetate (boiling point: 173 ° C.), dipropylene glycol dimethyl ether (boiling point: 171 ° C.), ethylene glycol monobutyl ether acetate (boiling point: 192 ° C.), diethylene glycol Diethyl ether (boiling point 189 ° C), diethylene glycol monomethyl ether (boiling point 194 ° C), propylene glycol diacetate (boiling point 190 ° C), 3-methoxybutyl acetate (boiling point 171 ° C), propylene glycol-n-butyl ether (boiling point 170 ° C), Examples thereof include diethylene glycol ethyl methyl ether (boiling point: 176 ° C) and diethylene glycol isopropyl
  • the solvent A contains the solvent represented by the formula (X) or the formula (Y) as a main component.
  • the main component means that the content of the solvent represented by the formula (X) or the formula (Y) is more than 50% by mass based on the total mass of the solvent A.
  • the solvent A for example, dipropylene glycol monomethyl ether
  • the main component is intended to mean that the content of the solvent mentioned as a specific example of the solvent A is more than 50% by mass based on the total mass of the solvent A.
  • the content of the solvent A in the photosensitive composition is preferably from 0.1 to 20% by mass, more preferably from 0.3 to 5.0% by mass, based on the total mass of the photosensitive composition.
  • the photosensitive composition preferably contains a solvent B selected from the group consisting of a solvent B1 having a boiling point of 100 to 130 ° C. at 1 atm and a solvent B2 having a boiling point at more than 130 ° C. and less than 170 ° C. at 1 atm.
  • the boiling point of the solvent B1 at 1 atm is 100 to 130 ° C, preferably 120 to 130 ° C.
  • the boiling point of the solvent B2 at 1 atm is more than 130 ° C. and less than 170 ° C., preferably 140 to 150 ° C.
  • solvent B1 examples include butyl acetate (boiling point 126 ° C.), ethylene glycol monomethyl ether (boiling point 125 ° C.), methyl-n-butyl ketone (boiling point 127 ° C.), and tetrahydrofuran (boiling point 126 ° C.).
  • propylene glycol 1-monomethyl ether 2-acetate (boiling point 145 ° C.), ethylene glycol monomethyl ether acetate (boiling point 145 ° C.), ethyl lactate (boiling point 155 ° C.), diethylene glycol dimethyl ether (boiling point 162 ° C.), 3-methoxy Butanol (boiling point 161 ° C.) and propylene glycol-n-propyl ether (boiling point 150 ° C.).
  • the content of the solvent B in the photosensitive composition is preferably from 20 to 90% by mass, more preferably from 40 to 70% by mass, based on the total mass of the photosensitive composition.
  • the mass ratio of solvent A to solvent B (mass of solvent A / mass of solvent B) in the photosensitive composition is preferably from 0.005 to 0.500, more preferably from 0.010 to 0.200.
  • the content of the solvent B1 in the photosensitive composition is preferably 0.1 to 10% by mass, and more preferably 0.5 to 5% by mass based on the total mass of the photosensitive composition. 0.0% by mass is more preferred.
  • the content of the solvent B1 in the photosensitive composition is preferably from 20 to 80% by mass, more preferably from 30 to 70% by mass, based on the total mass of the photosensitive composition.
  • the solvent B may be used alone or in combination of two or more. Above all, it is preferable to use the above-mentioned solvent B1 and the above-mentioned solvent B2 in combination in that the effect of the present invention is more excellent.
  • the mass ratio of the solvent B1 to the solvent B2 (the mass of the solvent B1 / the mass of the solvent B2) is preferably 0.005 to 0.500, and 0.010 to 0.200. More preferred.
  • the photosensitive composition may contain a surfactant from the viewpoint of further improving coatability.
  • a surfactant from the viewpoint of further improving coatability.
  • the pattern rectangularity is more excellent.
  • the surfactant include a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant, and a fluorine-based surfactant, or a silicone-based surfactant.
  • a system surfactant is preferred.
  • fluorinated surfactant examples include Megafac F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, and F479.
  • F482, F554, F780, F781, F781F (above, manufactured by DIC), Florado FC430, FC431, FC171 (above, manufactured by Sumitomo 3M Limited), Surflon S-382, SC- 101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (all manufactured by Asahi Glass Co., Ltd.) , PF636, PF656, PF6320, PF6520, PF7002 (manufactured by OMNOVA) and the like.
  • Nonionic surfactants include polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester, oxyethylene
  • Examples include oxypropylene block copolymers, acetylene glycol-based surfactants, and acetylene-based polyoxyethylene oxide.
  • Examples of the cationic surfactant include the cationic surfactants described in paragraph 0554 of JP-A-2012-208494 ( ⁇ 0680> of the corresponding US Patent Application Publication No. 2012/0235099). Is incorporated herein by reference.
  • Examples of the anionic surfactant include W004, W005, and W017 (manufactured by Yusho Co., Ltd.).
  • Examples of the silicone surfactant include silicone surfactants described in JP-A-2012-208494, paragraph 0556 (corresponding to U.S. Patent Application Publication No. 2012/0235099, ⁇ 0682>), and the like. These contents are incorporated in the present specification.
  • the content of the surfactant in the photosensitive composition is preferably from 0.0001 to 0.1000% by mass relative to the total mass of the photosensitive composition, from the viewpoint that the strength of the infrared light cut filter is more excellent. 0.0010 to 0.0700% by mass is more preferable.
  • the photosensitive composition may contain a dispersant.
  • a dispersant By including a dispersant, the dispersion stability of the specific particles in the photosensitive composition is improved.
  • the dispersant also functions as the binder described above.
  • a polymer dispersant eg, polyamidoamine and its salt, polycarboxylic acid and its salt, high molecular weight unsaturated acid ester, modified polyurethane, modified polyester, modified poly (meth) acrylate, (meth) acryl-based Copolymer and Naphthalenesulfonic Acid Formalin Condensate
  • polyoxyethylene alkyl phosphate polyoxyethylene alkylamine
  • alkanolamine alkanolamine.
  • the polymer dispersant include a linear polymer, a terminal-modified polymer, a graft polymer, and a block polymer.
  • terminal-modified polymer examples include a polymer having a phosphate group at a terminal, a polymer having a sulfonic acid group at a terminal, a polymer having a partial skeleton or a heterocyclic ring of an organic dye, and a hydroxyl group or a Examples include a polymer produced by modifying an oligomer or polymer having an amino group with an acid anhydride.
  • Examples of the graft polymer include a reaction product of poly (lower alkylene imine) and polyester, a reaction product of polyallylamine and polyester, an amphoteric dispersion resin having a basic group and an acidic group, a partial skeleton of an organic dye, Examples include a graft type polymer having a heterocyclic ring, and a copolymer of a macromonomer and an acid group-containing monomer.
  • Examples of the macromonomer used for producing the graft polymer by radical polymerization include known macromonomers, such as macromonomer AA-6 manufactured by Toagosei Co., Ltd. (polymethyl methacrylate having a methacryloyl group at the end group).
  • dispersant examples include “Disperbyk-101 (polyamidoamine phosphate), 107 (carboxylate), 110 (copolymer containing an acid group), 130 (polyamide), 161, 162, 163, manufactured by BYK Chemie.
  • Purse 5000 (phthalocyanine derivative), 13240 (polyesteramine), 3000, 17000, 27000 (polymer having a functional part at the terminal), 24000, 28000, 32000, 38500 (graft-type polymer) ", manufactured by Nikko Chemical Nikor T106 (polyoxyethylene sorbitan monooleate), MYS-IEX (polyoxyethylene monostearate), Hinoact T-8000E manufactured by Kawaken Fine Chemical Co., Ltd., and organosiloxane polymer KP- manufactured by Shin-Etsu Chemical Co., Ltd.
  • W001 cationic surfactant manufactured by Yusho Co., Ltd., polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether , Nonionic surfactants such as polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid ester; anionic surfactants such as "W004, W005, W017”; Morishita Sangyo Co., Ltd.
  • a dispersant When a dispersant is used, first, a dispersion composition is prepared using specific particles (and, if necessary, other infrared light shielding agents), a dispersant, and an appropriate solvent, and then mixed with the composition. Is preferred from the viewpoint of improving dispersibility.
  • the content of the dispersant in the photosensitive composition is preferably from 10 to 70% by mass, more preferably from 30 to 60% by mass, based on the total mass of the specific particles.
  • the photosensitive composition may contain a sensitizer. By including the sensitizer in the photosensitive composition, the pattern rectangularity is more excellent.
  • the sensitizer one that sensitizes the above-mentioned photopolymerization initiator by an electron transfer mechanism or an energy transfer mechanism is preferable.
  • the type of sensitizer used is not particularly limited, and examples thereof include compounds exemplified in paragraph 0202 of JP-A-2012-124545.
  • the content of the sensitizer in the photosensitive composition is preferably from 0.01 to 10.0% by mass, more preferably from 0.10 to 4.0% by mass, based on the total solids in the photosensitive composition. preferable.
  • the photosensitive composition may contain a crosslinking agent.
  • a crosslinking agent By including a crosslinking agent in the photosensitive composition, an improvement in the strength of the infrared light cut filter can be expected.
  • the crosslinking agent is preferably a compound having two or more crosslinking groups.
  • the crosslinkable group include an oxetane group, a cyanate group, and the same groups as those described for the crosslinkable group which the alkali-soluble binder may have, and an epoxy group, an oxetane group, or a cyanate group is preferable. That is, as the crosslinking agent, an epoxy compound, an oxetane compound, or a cyanate compound is preferable.
  • the type of the crosslinking agent used is not particularly limited, and examples thereof include compounds exemplified in paragraphs 0204 to 0209 of JP-A-2012-122045.
  • the photosensitive composition may contain a curing accelerator.
  • the type of curing accelerator used is not particularly limited, and examples thereof include compounds exemplified in paragraph 0211 of JP-A-2012-124545.
  • the photosensitive composition can be prepared by mixing the above components.
  • the use of the photosensitive composition is not particularly limited, it is preferably used for forming an infrared light shielding layer, and more preferably used for forming an infrared light cut filter. That is, the cured film formed using the photosensitive composition is preferably used for the infrared light shielding layer.
  • the infrared light cut filter formed using the photosensitive composition of the present invention includes, for example, an infrared light cut filter on the light receiving side of the solid-state imaging device, and a back surface side (the side opposite to the light receiving side) of the solid-state imaging device. ) Can be used for the infrared light cut filter.
  • the photosensitive composition of the present invention may be used by directly applying it on a color filter or a flattening layer to form a coating film. Since the photosensitive composition of the present invention can be supplied in a coatable state, an infrared light cut filter can be easily formed on a desired member or position of a solid-state imaging device.
  • the infrared cut filter of the present invention is formed using the above-described photosensitive composition of the present invention.
  • the thickness of the infrared light cut filter can be appropriately selected depending on the purpose, and is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and still more preferably 5 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more, in order to maintain the light-shielding ability.
  • the maximum transmittance of the infrared light cut filter at a wavelength of 400 to 1300 nm is not particularly limited, but is preferably 60% or more, and more preferably 65% or more.
  • the maximum transmittance of the infrared cut filter at a wavelength of 900 to 1300 nm is not particularly limited, but is preferably 20% or less, more preferably 10% or less, and most preferably 5% or less.
  • the infrared light cut filter has a function of absorbing or cutting infrared light (lenses for cameras such as digital cameras, mobile phones, and on-vehicle cameras, and optical lenses such as f- ⁇ lenses and pickup lenses).
  • Optical filters for semiconductor light-receiving elements infrared light cut filters for proximity illuminance sensors, infrared light cut filters or infrared light absorbing plates that block heat rays for energy saving, agriculture for the selective use of sunlight Coatings, recording media that use the absorption heat of infrared light, near-infrared light cut filters for electronic devices or photographs, protective glasses, sunglasses, heat-shielding films, optical character reading / recording, confidential document copy prevention, electronic Used for photographic photoreceptors and laser welding.
  • it is useful as a noise cut filter for a CCD (Charge Coupled Device) camera or a filter for a CMOS (Complementary Metal Oxide Semiconductor) image sensor.
  • CCD Charge Coupled Device
  • the method for producing the infrared light cut filter is not particularly limited, but it can be produced through a step of forming a coating film by applying the photosensitive composition of the present invention to a support. Further, as described later, a step of forming a pattern may be performed.
  • the photosensitive composition is dropped on a support (drop casting), a spin coater method, a slit spin coater method, a slit coater method, a screen printing method, and an applicator coating. Law.
  • the support on which the photosensitive composition of the present invention is applied may be a transparent substrate made of glass or the like.
  • each substrate in the solid-state imaging device may be used.
  • another substrate provided on the light receiving side of the solid-state imaging device may be used.
  • it may be a layer such as a flattening layer provided on the light receiving side of the solid-state imaging device.
  • a method for producing a patterned infrared light cut filter for example, a step of forming a coating film by applying the photosensitive composition of the present invention on a support, and a step of exposing the coating film in a pattern Forming a pattern by developing and removing an unexposed portion.
  • Exposure is used to include not only light of various wavelengths but also irradiation of radiation such as an electron beam and X-rays. Exposure is preferably performed by irradiation with radiation. Examples of the radiation include ultraviolet light, visible light, and an electron beam, and more specifically, KrF, ArF, g-line, h-line, and i-line. No. Examples of the exposure method include a stepper exposure and an exposure using a high-pressure mercury lamp. Exposure is preferably 5 ⁇ 3000mJ / cm 2, more preferably 10 ⁇ 2000mJ / cm 2.
  • a pattern may be formed by a dry etching method.
  • Other steps may be included in the method for manufacturing an infrared light cut filter.
  • Other steps include, for example, a surface treatment step of the support, a pre-heating step (pre-baking step), and a post-heating step (post-baking step).
  • the heating temperature in the preheating step is preferably from 80 to 200 ° C, more preferably from 90 to 150 ° C.
  • the heating time in the preheating step is preferably 30 to 240 seconds when a hot plate is used.
  • the heating temperature in the post-heating step is preferably from 120 to 250 ° C, more preferably from 160 to 220 ° C.
  • the heating time in the post-heating step is preferably 3 minutes to 180 minutes when using a hot plate.
  • the infrared light cut filter can be suitably applied to a solid-state imaging device.
  • reference numeral 110 denotes a solid-state imaging device substrate.
  • an infrared light cut filter 111 and a color filter 112 are arranged on the solid-state imaging element substrate 110.
  • An area 114 is provided between the infrared light transmitting filter (color filter transmitting infrared light) 113 and the solid-state imaging device substrate 110.
  • a resin layer for example, a transparent resin layer or the like that can transmit light having a wavelength transmitted through the infrared light transmission filter 113 is disposed.
  • An infrared light transmitting filter 113 may be formed in the region 114. That is, the infrared light transmitting filter 113 may be formed on the solid-state imaging device substrate 110.
  • a micro lens 115 is arranged on the incident light h ⁇ side of the color filter 112 and the infrared light transmission filter 113.
  • a flattening layer 116 is formed so as to cover the microlenses 115.
  • the film thickness of the color filter 112 and the film thickness of the infrared light transmitting filter 113 are the same, but the film thicknesses of both may be different.
  • the color filter 112 is provided closer to the incident light h ⁇ than the infrared light cut filter 111.
  • the order of the infrared light cut filter 111 and the color filter 112 is changed so that the infrared light cut filter 111 is cut off.
  • the filter 111 may be provided closer to the incident light h ⁇ than the color filter 112.
  • Another layer may be formed between the infrared light cut filter 111 and the color filter 112.
  • the color filter 112 is selected from the group consisting of a color filter that transmits light in a red wavelength region, a color filter that transmits light in a green wavelength region, and a color filter that transmits light in a blue wavelength region. Preferably, at least one is included. Note that the color filter 112 may include an infrared light absorbing substance, and the color filter 112 may have a function as an infrared light cut filter.
  • the solid-state imaging device of the present invention includes the infrared light cut filter inside, the infrared light cut filter as a member of the camera module is not required, the number of parts of the camera module can be reduced, and the camera module can be downsized. Can be achieved.
  • the color filter 112 is not particularly limited, and a conventionally known color filter for forming a pixel can be used.
  • paragraphs 0214 to 0263 of JP-A-2014-043556 can be referred to.
  • the contents are incorporated herein.
  • the characteristics of the infrared light transmitting filter 113 are selected according to the emission wavelength of the light source.
  • One preferred embodiment of the solid-state imaging device is a color filter that transmits light in a red wavelength region (red color filter), a color filter that transmits light in a green wavelength region (green color filter), and a blue wavelength region.
  • a filter layer including at least one selected from the group consisting of a color filter transmitting blue light (blue color filter) and a color filter transmitting infrared light (infrared light transmission filter); It is preferable to include an infrared light cut filter arranged on the light incident side.
  • a filter layer having a red color filter, a green color filter, a blue color filter, and an infrared light transmission filter on the same plane, and an infrared light cutoff arranged on the light incident side of the filter layer and arranged on the entire filter layer
  • a solid-state imaging device including a filter.
  • the infrared light cut filter may be disposed on the light incident side of the substrate 110.
  • an infrared light cut filter may be arranged on a red color filter, a green color filter, and a blue color filter, and an infrared light cut filter may be arranged on an infrared light transmission filter.
  • a flattening layer may be arranged between the filter layer and the infrared light cut filter.
  • FIG. 2 is a functional block diagram of the imaging apparatus.
  • the imaging apparatus includes a lens optical system 1, a solid-state imaging device 10, a signal processing unit 20, a signal switching unit 30, a control unit 40, a signal storage unit 50, a light emission control unit 60, and a device that emits infrared light.
  • An infrared LED (light emitting diode) 70 serving as a light emitting element, and image output units 80 and 81 are provided.
  • the solid-state imaging device 100 described above can be used as the solid-state imaging device 10.
  • all or a part of the configuration other than the solid-state imaging device 10 and the lens optical system 1 can be formed on the same semiconductor substrate.
  • paragraphs 0032 to 0036 of JP-A-2011-233983 can be referred to, and the contents thereof are incorporated in the specification of the present application.
  • the imaging device include a motion sensor, a proximity sensor, a gesture sensor, and the like.
  • composition (photosensitive composition)> The components shown in Table 1 below were dissolved in the solvents shown in Table 1 to prepare photosensitive compositions.
  • Resin binder Acrycure RD-F8 manufactured by Nippon Shokubai (corresponding to an alkali-soluble binder having a double bond group) (Polymerizable compound) DPHA: KAYARAD DPHA (Nippon Kayaku Co., Ltd.) (Polymerization initiator) IRGACURE 369: IRGACURE 369 (manufactured by BASF) (Sensitizer) DETX-S: Gayacure DETX-S (2,4-diethylthioxanthone) (manufactured by Shoji Sangyo Co., Ltd.) (solvent) PGMEA: 1-methoxy-2-propanol acetate (Surfactant) Megafac F-781-F (manufactured by DIC)
  • UV absorber UV absorber
  • Table 2 below shows the results of the thermal mass measurement of UV1 to UV-6.
  • Specific particles 1 were produced according to the following procedure. A mixture of tungsten fine particles (composition: Cs 0.33 WO 3 , average particle diameter: 20 nm) (100 parts by mass), ethyl silicate (10 parts by mass), and methanol (90 parts by mass) was stirred at 0 ° C. for 10 hours. Thereafter, the mixture was stirred at 20 ° C. for 20 hours. The solid content was collected by filtration from the obtained mixture, and the collected solid content was dried at 25 ° C. for 24 hours, 100 ° C. for 10 hours, and 200 ° C. for 1 hour, and then pulverized to obtain specific particles 1 (coated with SiO 2 Tungsten fine particles).
  • specific particles 2 to 4 were produced according to the same procedure as above except that the type of the coupling agent was changed.
  • the specific particles 2 were tungsten fine particles coated with TiO 2
  • the specific particles 3 were tungsten fine particles coated with Al 2 O 3
  • the specific particles 4 were tungsten fine particles coated with ZrO 2 .
  • the tungsten fine particles that were not coated were designated as specific particles 5.
  • the composition further contains a dispersant.
  • the dispersant has a function of dispersing the specific particles.
  • the pigment dispersion 1 is a composition containing the following components. ⁇ C. I. Pigment Green 58 11.4 parts by mass ⁇ C. I. Pigment Yellow 185 2.3 parts by mass -Compound 1 having the following structure: 1.4 parts by mass
  • the pigment dispersion 2 is a composition containing the following components. ⁇ C. I. Pigment Red 254 ... 11.4 parts by mass ⁇ C. I. Pigment Yellow 139 ... 2.3 parts by mass -Compound 1 having the above structure: 1.4 parts by mass -Dispersant 1 ... 7.2 parts by mass ⁇ Propylene glycol methyl ether acetate: 77.77 parts by mass
  • the pigment dispersion 3 is a composition containing the following components. ⁇ C. I. Pigment Blue 15: 6 ... 11.4 parts by mass ⁇ C. I. Pigment Bio Red 23 ... 2.3 parts by mass -Compound 1 having the above structure: 1.4 parts by mass -Dispersant 1 ... 7.2 parts by mass ⁇ Propylene glycol methyl ether acetate: 81.9 parts by mass
  • the photosensitive composition of Example 1 was applied on a glass wafer by spin coating so that the thickness after film formation was 2.7 ⁇ m, and then heated at 100 ° C. for 2 minutes on a hot plate. Thereafter, using a i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), the obtained coating film was entirely exposed at 1000 mJ / cm 2 , and further heated on a hot plate at 220 ° C. for 5 minutes. A cured layer was obtained. Next, the Green composition was applied on the cured layer by a spin coating method so that the film thickness after film formation became 1.5 ⁇ m, and then heated at 100 ° C. for 2 minutes on a hot plate.
  • FPA-3000i5 + manufactured by Canon Inc.
  • the obtained coating film was entirely exposed at 1000 mJ / cm 2 , and further heated on a hot plate at 220 ° C. for 5 minutes.
  • a Green film was laminated on the cured layer to obtain a sample G1 including the cured layer and the Green film.
  • a sample R1 including a cured layer and a Red film and a sample B1 including a cured layer and a Blue film were obtained using a Red composition or a Blue composition instead of the Green composition.
  • Various samples were prepared using the photosensitive compositions of other Examples and Comparative Examples instead of the photosensitive composition of Example 1 above.
  • the light transmittance of the obtained sample was measured in the wavelength range of 400 to 1300 nm using an ultraviolet-visible-near-infrared spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corporation).
  • the obtained sample was heated on a hot plate at 240 ° C. for 300 seconds, and a change in transmittance ( ⁇ T) in a wavelength range of 400 to 1300 nm before and after the heating was measured and used as an index of heat resistance.
  • ⁇ T change in transmittance
  • the above ⁇ T represents a transmittance change at a wavelength showing the largest transmittance change in a wavelength range of 400 to 1300 nm. Practically, A or B is preferable.
  • the substrate was naturally dried, and post-baked on a hot plate at 220 ° C. for 300 seconds to form a cured film (thickness: 2.7 ⁇ m) as a line portion.
  • the rectangularity was evaluated by evaluating the cross section of the obtained line portion. Specifically, as shown in FIG. 3, the value of the angle ⁇ formed by the line portion 202 with respect to the silicon substrate 200 was obtained and evaluated according to the following criteria. Practically, A or B is preferable. “A”: ⁇ is 80 to 100 ° “B”: ⁇ is 70 ° or more and less than 80 °, or more than 100 ° and 110 ° or less “C”: ⁇ is less than 70 ° or more than 110 °
  • the photosensitive composition was prepared in the same procedure as in Example 6 except that the resin A was replaced with the resin B (the following structure) as a binder, and various evaluations were performed. Obtained.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that DPHA was changed to Aronix M-510 (manufactured by Toagosei Co., Ltd.) as a polymerizable compound, and various evaluations were made. was gotten.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that DPHA-20 (manufactured by Nippon Kayaku) was used instead of DPHA as a polymerizable compound, and various evaluations were made. was gotten.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that DPHA was replaced with Ogzol EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd.) as a polymerizable compound, and various evaluations were performed. The result was obtained.
  • the pattern rectangularity was more excellent than that of Example 6. From this result, it is considered that the use of two or more polymerizable compounds further improved the pattern shortness.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that IRGACURE369 was changed to IRGACUREOXE01 (manufactured by BASF) as an initiator, and various evaluations were performed. I was From these results, it is considered that the use of the oxime compound (oxime-based initiator) further improved the pattern rectangularity.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that IRGACURE369 was changed to IRGACUREOXE03 (manufactured by BASF) as an initiator, and various evaluations were performed. I was From these results, it is considered that the use of the oxime compound (oxime-based initiator) further improved the pattern rectangularity.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that IRGACURE369 was changed to IRGACUREOXE04 (manufactured by BASF) as an initiator, and various evaluations were performed. I was From these results, it is considered that the use of the oxime compound (oxime-based initiator) further improved the pattern rectangularity.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that the sensitizer was not used, and various evaluations were performed. The same result was obtained except that the pattern rectangularity was B. It is considered that the use of the sensitizer further improved the pattern rectangularity.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that the surfactant was not used, and various evaluations were performed. The same result was obtained except that the pattern rectangularity was B. It is considered that the use of the surfactant further improved the pattern rectangularity.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that butyl acetate was used instead of ethylene glycol monobutyl ether acetate, and various evaluations were performed. As a result, a result similar to that of Example 6 was obtained.
  • a photosensitive composition was prepared in the same manner as in Example 6 except that PGMEA was used instead of butyl acetate, and various evaluations were performed. As a result, a result similar to that of Example 6 was obtained.
  • lens optical system 10: solid-state imaging device, 20: signal processing unit, 30: signal switching unit, 40: control unit, 50: signal storage unit, 60: light emission control unit, 70: infrared LED, 80, 81 : Image output unit, 100: solid-state image sensor, 110: solid-state image sensor substrate, 111: infrared light cut filter, 112: color filter, 113: infrared light transmission filter, 114: area, 115: micro lens, 116 : Flattening layer, 200: silicon substrate, 202: line portion, h ⁇ : incident light

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Abstract

L'invention concerne : une composition photosensible qui permet de former un motif qui est excellent en termes de rectitude d'une forme de section transversale et qui permet de former un film durci ayant une excellente résistance à la chaleur ; un filtre coupant la lumière infrarouge ; et un dispositif d'imagerie à semi-conducteurs. Cette composition photosensible contient des particules d'oxyde de tungstène qui contiennent du métal, un composé polymérisable, un initiateur de polymérisation, un absorbeur de rayonnement ultraviolet et un inhibiteur de polymérisation. Le rapport en poids de la teneur en absorbeur de rayonnement ultraviolet à la teneur en inhibiteur de polymérisation est de 0,08 à 330.
PCT/JP2019/022921 2018-07-20 2019-06-10 Composition photosensible, filtre coupant la lumière infrarouge, et dispositif d'imagerie à semi-conducteurs WO2020017187A1 (fr)

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WO2017146091A1 (fr) * 2016-02-26 2017-08-31 富士フイルム株式会社 Composition sensible à un rayonnement, filtre optique, stratifié, procédé de formation de motif, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et capteur infrarouge
WO2018012440A1 (fr) * 2016-07-15 2018-01-18 富士フイルム株式会社 Corps stratifié, kit, procédé de production de corps stratifié et capteur optique
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WO2018131350A1 (fr) * 2017-01-11 2018-07-19 富士フイルム株式会社 Composition, film, filtre optique, procédé de formation de motif, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge

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JP2016006476A (ja) * 2014-01-21 2016-01-14 富士フイルム株式会社 近赤外線吸収性組成物、近赤外線カットフィルタおよびその製造方法、ならびに、カメラモジュールおよびその製造方法
WO2017146091A1 (fr) * 2016-02-26 2017-08-31 富士フイルム株式会社 Composition sensible à un rayonnement, filtre optique, stratifié, procédé de formation de motif, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et capteur infrarouge
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WO2023042447A1 (fr) * 2021-09-16 2023-03-23 ソニーセミコンダクタソリューションズ株式会社 Dispositif d'imagerie

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