WO2021230122A1 - Composition de résine photosensible magenta, film, filtre coloré, capteur d'image à semi-conducteurs et unité d'affichage visuel - Google Patents

Composition de résine photosensible magenta, film, filtre coloré, capteur d'image à semi-conducteurs et unité d'affichage visuel Download PDF

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Publication number
WO2021230122A1
WO2021230122A1 PCT/JP2021/017328 JP2021017328W WO2021230122A1 WO 2021230122 A1 WO2021230122 A1 WO 2021230122A1 JP 2021017328 W JP2021017328 W JP 2021017328W WO 2021230122 A1 WO2021230122 A1 WO 2021230122A1
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WIPO (PCT)
Prior art keywords
group
magenta
photosensitive resin
resin composition
wavelength range
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PCT/JP2021/017328
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English (en)
Japanese (ja)
Inventor
裕樹 奈良
Original Assignee
富士フイルム株式会社
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Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to JP2022521853A priority Critical patent/JP7389900B2/ja
Priority to KR1020227037314A priority patent/KR20220161397A/ko
Publication of WO2021230122A1 publication Critical patent/WO2021230122A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B48/00—Quinacridones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • 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 magenta photosensitive resin composition.
  • the present invention also relates to a film, a color filter, a solid-state image pickup device, and an image display device using a magenta color photosensitive resin composition.
  • CCD charge-coupled device
  • the colored pixels of each color of the color filter are manufactured by using a photosensitive resin composition containing a coloring material (Patent Document 1 and the like).
  • a magenta color pigment and a magenta color dye are used in combination as the coloring material.
  • the coloring material contains a magenta color pigment and a magenta color dye.
  • the content of the magenta color dye in the coloring material is 20% by mass or more, and the content is 20% by mass or more.
  • a magenta-colored photosensitive resin composition in which the total amount of the magenta-colored pigment and the magenta-colored dye in the total solid content of the magenta-colored photosensitive resin composition is 30% by mass or more.
  • the magenta color photosensitive resin composition has a maximum absorbance of 0.5 or less for light in the wavelength range of 400 to 450 nm and 600 to 700 nm when the absorbance for light having a wavelength of 540 nm is 1.
  • the magenta color photosensitive resin composition according to ⁇ 1>, wherein the maximum value of the absorbance with respect to light in the wavelength range of is 0.5 or less.
  • the magenta color photosensitive resin composition has a wavelength range of 450 to 520 nm and a wavelength range of 550 to 600 nm for light having an absorbance of 0.3 when the absorbance for light having a wavelength of 540 nm is 1.
  • ⁇ 4> When a film having a thickness of 0.6 ⁇ m is formed using the magenta color photosensitive resin composition, the maximum value of the light transmittance in the wavelength range of 400 to 500 nm in the thickness direction of the film is 70%.
  • the minimum value of the transmittance of light in the wavelength range of 450 to 600 nm is 30% or less
  • the maximum value of the transmittance of light in the wavelength range of 550 to 700 nm is 70% or more.
  • the magenta photosensitive resin composition according to the above.
  • the maximum value of light transmittance in the wavelength range of 400 to 500 nm in the thickness direction of the film is 80%.
  • the minimum value of the transmittance of light in the wavelength range of 450 to 600 nm is 10% or less
  • the maximum value of the transmittance of light in the wavelength range of 550 to 700 nm is 90% or more.
  • magenta photosensitive resin composition according to the above.
  • ⁇ 6> The magenta photosensitive resin composition according to any one of ⁇ 1> to ⁇ 5>, wherein the magenta dye is a compound having a polymerizable group.
  • ⁇ 7> The magenta photosensitive resin composition according to any one of ⁇ 1> to ⁇ 6>, wherein the magenta dye is a dye multimer.
  • ⁇ 8> The magenta color photosensitive resin composition according to any one of ⁇ 1> to ⁇ 7>, wherein the magenta color dye is at least one selected from a xanthene compound, a pyrromethene compound and a triarylmethane compound. ..
  • the magenta color pigment is at least one selected from Color Index Pigment Red 122, Color Index Pigment Red 202, Color Index Pigment Red 209, and Color Index Pigment Red 269, ⁇ 1> to ⁇ 8>.
  • ⁇ 12> The magenta color photosensitive resin composition according to any one of ⁇ 1> to ⁇ 11>, which is used for a solid-state image sensor.
  • ⁇ 13> The magenta color photosensitive resin composition according to any one of ⁇ 1> to ⁇ 12>, which is used for photolithography.
  • ⁇ 14> A film obtained by using the magenta photosensitive resin composition according to any one of ⁇ 1> to ⁇ 13>.
  • ⁇ 15> A color filter having the film according to ⁇ 14>.
  • ⁇ 16> A magenta color pixel obtained by using the magenta color photosensitive resin composition according to any one of ⁇ 1> to ⁇ 13>, a cyan color pixel including a color index pigment green 7, and a color index pigment.
  • a color filter having yellow pixels including yellow 150. ⁇ 17> It has a magenta color pixel, a cyan color pixel, and a yellow pixel obtained by using the magenta color photosensitive resin composition according to any one of ⁇ 1> to ⁇ 13>.
  • the cyan pixel has a maximum transmittance of 90% or more for light in the wavelength range of 450 to 550 nm, a minimum value of 20% or less for the transmittance of light in the wavelength range of 615 to 645 nm, and a transmittance of 50.
  • the maximum value of the light transmittance in the wavelength range of 500 to 700 nm is 90% or more
  • the minimum value of the light transmittance in the wavelength range of 415 to 445 nm is 10% or less
  • the transmittance is 50%.
  • the wavelength indicating the above exists in the wavelength range of 470 to 490 nm.
  • Color filter. ⁇ 18> A solid-state image sensor having the film according to ⁇ 14>. ⁇ 19> An image display device having the film according to ⁇ 14>.
  • magenta photosensitive resin composition capable of forming magenta pixels having a small amount of development residue, excellent resolution, and a small surface roughness. Further, it is possible to provide a film, a color filter, a solid-state image pickup device, and an image display device using a magenta color photosensitive resin composition.
  • the contents of the present invention will be described in detail.
  • "to” is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
  • the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
  • 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).
  • the term "exposure” includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
  • Examples of the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
  • EUV light extreme ultraviolet rays
  • (meth) acrylate” represents both acrylate and methacrylate, or either
  • “(meth) acrylic” represents both acrylic and methacrylic, or either.
  • Acryloyl represents both acryloyl and / or methacryloyl.
  • Me in the structural formula represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
  • the total solid content means the total mass of all the components of the composition excluding the solvent.
  • the term "process" is included in this term not only as an independent process but also as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
  • the magenta color photosensitive resin composition of the present invention is a magenta color photosensitive resin composition containing a coloring material, a resin, a polymerizable compound, and a solvent.
  • the coloring material contains magenta pigments and magenta dyes.
  • the content of the magenta color dye in the coloring material is 20% by mass or more, and the content is 20% by mass or more.
  • the total amount of the magenta pigment and the magenta dye in the total solid content of the magenta photosensitive resin composition is 30% by mass or more.
  • magenta photosensitive resin composition of the present invention it is possible to form magenta pixels having a small amount of development residue, excellent resolution, and a small surface roughness.
  • the magenta color photosensitive resin composition of the present invention has a maximum absorbance of 0.5 or less and 600 to 700 nm for light in the wavelength range of 400 to 450 nm, where 1 is the absorbance for light having a wavelength of 540 nm.
  • the maximum value of the absorbance for light in the wavelength range is preferably 0.5 or less.
  • the maximum value of the absorbance for light in the wavelength range of 400 to 450 nm is more preferably 0.3 or less, and further preferably 0.2 or less.
  • the maximum value of the absorbance for light in the wavelength range of 600 to 700 nm is more preferably 0.3 or less, and further preferably 0.2 or less.
  • the magenta color photosensitive resin composition of the present invention has a wavelength range of 450 to 520 nm and a wavelength range of 550 to 600 nm for which the absorbance is 0.3 when the absorbance for light having a wavelength of 540 nm is 1. It is preferable to be present in each. It is said that the wavelength on the short wavelength side (hereinafter, also referred to as ⁇ 1) having an absorbance of 0.3 can be sufficiently color-separated from colored pixels of other colors such as cyan and yellow, and the color reproducibility of the image sensor can be improved. For this reason, it is more preferably present in the wavelength range of 460 to 510 nm, and even more preferably in the wavelength range of 470 to 500 nm.
  • the wavelength on the long wavelength side (hereinafter, also referred to as ⁇ 2) having an absorbance of 0.3 is more preferably present in the wavelength range of 560 to 595 nm for the same reason as described above, and is in the wavelength range of 570 to 590 nm. It is more preferred to be present.
  • the difference between ⁇ 2 and ⁇ 1 ( ⁇ 2- ⁇ 1) is because the amount of light incident on the photodiode can be sufficiently secured while sufficiently ensuring the performance of color separation from the colored pixels of other colors. It is preferably 60 to 120 nm, more preferably 70 to 110 nm.
  • the absorbance A ⁇ at a certain wavelength ⁇ is defined by the following equation (Ab1).
  • a ⁇ -log (T ⁇ / 100) ...
  • a ⁇ is the absorbance at the wavelength ⁇ , and T ⁇ is the transmittance (%) at the wavelength ⁇ .
  • the absorbance value may be a value measured in a solution state, or may be a value of a film formed by using a magenta color photosensitive resin composition.
  • a magenta-color photosensitive resin composition is applied onto a glass substrate by a method such as spin coating, dried at 100 ° C. for 2 minutes using a hot plate or the like, and then the light illuminance is 20 mW.
  • I-line exposure under the conditions of / cm 2 and exposure amount 1 J / cm 2 then heating on a hot plate at 100 ° C. for 20 minutes and allowing to cool to room temperature is used for measurement. Is preferable.
  • Absorbance can be measured using a conventionally known spectrophotometer.
  • the maximum value of light transmission in the wavelength range of 400 to 500 nm in the thickness direction of the film is 70% or more.
  • the minimum value of light transmission in the wavelength range of 450 to 600 nm is 30% or less, and the maximum value of light transmission in the wavelength range of 550 to 700 nm is 70% or more, and light transmission in the thickness direction of the film. It is preferable that the wavelength showing a ratio of 50% exists in each of the wavelength range of 450 to 500 nm and the wavelength range of 550 to 600 nm.
  • the maximum value of the light transmittance in the wavelength range of 400 to 500 nm is more preferably 75% or more, further preferably 80% or more.
  • the minimum value of the transmittance of light in the wavelength range of 450 to 600 nm is more preferably 20% or less, further preferably 15% or less, and particularly preferably 10% or less.
  • the maximum value of the transmittance of light in the wavelength range of 550 to 700 nm is more preferably 80% or more, further preferably 90% or more.
  • the wavelength on the short wave side showing a light transmittance of 50% in the thickness direction of the film is more preferably present in the wavelength range of 460 to 495 nm, further preferably in the range of 470 to 495 nm, and 475 to 495 nm.
  • the wavelength on the long wave side showing a light transmittance of 50% in the thickness direction of the film is more preferably present in the wavelength range of 560 to 595 nm, and further preferably present in the range of 570 to 590 nm.
  • the magenta photosensitive resin composition of the present invention can be preferably used for a solid-state image sensor. Further, the magenta color photosensitive resin composition of the present invention can be preferably used for a color filter. Specifically, it can be preferably used for forming magenta pixels of a color filter. Further, the magenta color photosensitive resin composition of the present invention can be preferably used for forming magenta color pixels of a color filter used in a solid-state image sensor. Further, the magenta color photosensitive resin composition of the present invention can also be used as a magenta color photosensitive resin composition for photolithography.
  • the magenta color photosensitive resin composition of the present invention contains a coloring material.
  • a magenta color pigment and a magenta color dye are used as the coloring material.
  • the magenta color is a complementary hue of green.
  • the complementary color is a combination of colors having a relationship of being located opposite to each other on the color wheel.
  • the magenta color pigment is a pigment exhibiting a magenta hue
  • the magenta color dye is a dye exhibiting a magenta hue.
  • the magenta color pigment refers to a magenta color pigment compound that is difficult to dissolve in a solvent.
  • the magenta color pigment preferably has a solubility of less than 1 g in 100 g of water at 23 ° C and 100 g of cyclohexanone at 23 ° C.
  • the magenta color dye refers to a magenta color dye compound dissolved in water or an organic solvent.
  • the magenta color dye preferably has a solubility of 1 g or more in 100 g of cyclohexanone at 23 ° C., and more preferably 5 g or more.
  • magenta color pigment examples include pigments having a high absorbance of light having a green wavelength and a low absorbance of light having a red and blue wavelength.
  • the maximum absorption wavelength of the magenta color pigment preferably exists in the wavelength range of 500 to 600 nm, more preferably in the wavelength range of 500 to 590 nm, further preferably in the range of 500 to 585 nm, and more preferably 500. It is particularly preferably present in the range of ⁇ 580 nm.
  • the wavelength having an absorbance of 0.5 exists at 450 nm or more on the shorter wavelength side than the maximum absorption wavelength. It is more preferable that it is present at 460 nm or more, and further preferably it is present at 470 nm or more. Further, in the magenta color pigment used in the present invention, when the absorbance of the maximum absorption wavelength in the wavelength range of 500 to 600 nm is 1, the wavelength at which the absorbance is 0.5 is 650 nm on the longer wavelength side than the maximum absorption wavelength.
  • the magenta color pigment used in the present invention has a maximum absorption wavelength and a wavelength ⁇ 1 (a wavelength shorter than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance of the maximum absorption wavelength is 1).
  • the difference between the two is preferably 110 nm or less, more preferably 100 nm or less, and further preferably 90 nm or less.
  • the difference between the wavelength ⁇ 2 (the wavelength longer than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance of the maximum absorption wavelength is 1) and the maximum absorption wavelength is preferably 110 nm or less.
  • the difference ( ⁇ 2- ⁇ 1) between the wavelength ⁇ 2 and the wavelength ⁇ 1 is preferably 130 nm or less, more preferably 120 nm or less, and more preferably 115 nm or less. It is more preferably 110 nm or less, and particularly preferably 110 nm or less.
  • the magenta color pigment is preferably a compound having a pigment skeleton selected from a quinacridone skeleton, a dioxazine skeleton and a naphthol azo skeleton, and more preferably a compound having a pigment skeleton selected from the quinacridone skeleton and the dioxazine skeleton. It is more preferable that the compound has a quinacridone skeleton as the pigment skeleton for the reason of stability.
  • magenta color pigments include Color Index (CI) Pigment Red 122, C.I. I. Pigment Red 202, C.I. I. Pigment Red 209, C.I. I. Pigment Red 269, C.I. I. Pigment Violet 19, C.I. I. Pigment Violet 23, C.I. I. Pigment Red 122, C.I. I. Pigment Red 202, C.I. I. Pigment Red 209 and C.I. I. Pigment Red 269 is preferred, with C.I. I. Pigment Red 122 is more preferred.
  • CI Color Index
  • the average primary particle size of the magenta color pigment is preferably 50 nm or less, more preferably 47 nm or less, and further preferably 45 nm or less.
  • the lower limit is not particularly limited, but is preferably 10 nm or more, and more preferably 20 nm or more.
  • the average primary particle size of the magenta color pigment is 50 nm or less, fine pixels (patterns) having excellent linearity can be formed.
  • the average primary particle size of the pigment is obtained by observing the pigment using a transmission electron microscope (for example, JEM-2100F type, a device equivalent to an electric field radiation transmission electron microscope manufactured by JEOL Ltd.). It refers to the number average particle size obtained from the photographs taken.
  • the projected area of the pigment is obtained by the above apparatus, and the equivalent circle diameter of each pigment is obtained from the projected area to calculate the average primary particle size. More specifically, after measuring the equivalent circle diameters of 100 pigments, the equivalent circle diameters of 80 pigments excluding the 10 maximum side and 10 minimum side are arithmetically averaged to average the pigments. Calculate the primary particle size.
  • magenta color dye examples include dyes having a high absorbance of light having a green wavelength and a low absorbance of light having a red and blue wavelength.
  • the magenta dye is preferably a dye having a high absorbance of light in the wavelength range of 500 to 550 nm, a low absorbance of light in the wavelength range of 400 to 480 nm, and a low absorbance of light in the wavelength range of 600 to 700 nm. ..
  • the magenta color dye preferably has ⁇ represented by the following formula (A1) of 150 nm or less, more preferably 100 nm or less, and further preferably 50 nm or less.
  • ⁇ 1 a wavelength on the shorter wavelength side than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance of the maximum absorption wavelength of the magenta color dye is 1
  • ⁇ 2 is the maximum absorption wavelength of the magenta color dye.
  • the absorbance of is 1, it is a wavelength on the longer wavelength side than the maximum absorption wavelength at which the absorbance is 0.5.
  • the maximum absorption wavelength of the magenta color dye is preferably in the wavelength range of 450 to 600 nm, more preferably in the wavelength range of 475 to 575 nm, and even more preferably in the wavelength range of 500 to 550 nm.
  • the magenta color dye has a ratio (A1 / A2) of 0.2 to 0.
  • the magenta color dye has a ratio (A3 / A2) of 0.3 or less between the maximum value A3 of the absorbance of light in the wavelength range of 600 to 700 nm and the minimum value A2 of the absorbance of light in the wavelength range of 500 to 550 nm.
  • magenta color dye has a ratio (A3 / A1) of 0.1 or less between the maximum value A3 of the absorbance of light in the wavelength range of 600 to 700 nm and the maximum value A1 of the absorbance of light in the wavelength range of 400 to 480 nm. It is preferably 0.03 or less, more preferably 0.02 or less, and even more preferably 0.02 or less.
  • Magenta dye, and absorbance A 440 of wavelength 440nm of light it is preferable that the ratio between the absorbance A 525 of wavelength 525nm of the light (A 440 / A 525) is 0.001 to 0.15 0.005 It is more preferably ⁇ 0.10, and even more preferably 0.01 to 0.05. Further, the magenta color dye, the absorbance A 650 of the light with a wavelength of 650 nm, it is preferable that the ratio between the absorbance A 525 of wavelength 525nm of the light (A 650 / A 525) of 0.2 or less, 0.1 or less Is more preferable, and 0.05 or less is further preferable.
  • magenta dye is preferably a ratio between the absorbance A 650 and wavelength 440nm absorbance A 440 of the light of the light with a wavelength of 650nm (A 650 / A 440) of 0.1 or less, 0.03 or less It is more preferably present, and further preferably 0.02 or less.
  • magenta color dye examples include xanthene compounds, pyrromethene compounds, triarylmethane compounds, quinacridone compounds, cyanine compounds, anthrapyridone compounds, anthraquinone compounds and the like, and xanthene compounds, pyrromethene compounds and tria from the viewpoint of spectroscopic as magenta color.
  • a reelmethane compound is preferable, and a xanthene compound is more preferable.
  • triarylmethane compound examples include compounds represented by the following formula (TP).
  • Rtp 1 to Rtp 4 independently represent a hydrogen atom, an alkyl group or an aryl group, respectively.
  • Rtp 5 represents a hydrogen atom, an alkyl group, an aryl group or NRtp 9 Rtp 10 (Rtp 9 and Rtp 10 represent a hydrogen atom, an alkyl group or an aryl group).
  • Rtp 6 , Rtp 7 and Rtp 8 represent substituents.
  • a, b and c represent integers from 0 to 4. a, when b and c is 2 or more, Rtp 6 together, Rtp 7 together and Rtp 8 each other, may be coupled to each other to form a ring.
  • X represents an anion. In the absence of X, at least one of Rtp 1 to Rtp 8 contains anions.
  • Rtp 1 to Rtp 4 are preferably a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, and a phenyl group.
  • Rtp 5 a hydrogen atom or NRtp 9 Rtp 10 is preferable, and NRtp 9 Rtp 10 is particularly preferable.
  • Rtp 9 and Rtp 10 are preferably a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or a phenyl group.
  • Examples of the substituent represented by Rtp 6 , Rtp 7 and Rtp 8 include the group mentioned in the substituent T described later and the polymerizable group.
  • X represents a counter anion.
  • the counter anion is not particularly limited. It may be an organic anion or an inorganic anion.
  • the counter anion is preferably an organic anion.
  • the counter anion include a fluorine anion, a chlorine anion, a bromine anion, an iodine anion, a cyanide ion, a perchlorate anion, and a non-nucleophilic anion. From the viewpoint of heat resistance, it is preferably a non-nucleophilic anion.
  • Examples of counter anions include known non-nucleophilic anions described in paragraph No. 0075 of JP-A-2007-310315, the contents of which are incorporated herein.
  • the non-nucleophilic property means a property that the dye is not nucleophilically attacked by heating.
  • an imide anion for example, a bis (sulfonyl) imide anion), a tris (sulfonyl) methyl anion, and an anion having a boron atom are preferable, and a bis (sulfonyl) imide anion and a tris (sulfonyl) methyl anion are more preferable, and a bis (sulfonyl) methyl anion is preferable.
  • a sulfonyl) imide anion is more preferred.
  • anion having a boron atom examples include a tetrafluoroborate anion, a tetraphenylborate anion, and a tetraperfluorophenylborate anion.
  • the molecular weight of the counter anion is preferably 100 to 1000, more preferably 200 to 500.
  • a, b or c each independently represents an integer of 0 to 4.
  • a and c are preferably 0 or 1, respectively, and more preferably 0.
  • b is preferably an integer of 0 to 2, more preferably 0 or 2.
  • formula (TP) if it contains at least one anion of Rtp 1 ⁇ Rtp 7, as the anion, -SO 3 -, -COO -, -PO 4 -, bis (sulfonyl) imide anion, tris (sulfonyl) methide anion And tetraarylborate anions are preferred, bis (sulfonyl) imide anions, tris (sulfonyl) methide anions and tetraarylborate anions are more preferred, and bis (sulfonyl) imide anions and tris (sulfonyl) methide anions are even more preferred.
  • a structure in which at least one of Rtp 1 to Rtp 7 is replaced by the formula (P) can be mentioned.
  • L represents a single bond or a divalent linking group
  • X 1 represents an anion.
  • L represents a single bond or a divalent linking group.
  • the divalent linking group it is preferable to represent -NR 10- , -O-, -SO 2- , an alkylene group containing a fluorine atom, an arylene group containing a fluorine atom, or a group consisting of a combination thereof.
  • a group consisting of a combination of -NR 10- and -SO 2 and an alkylene group containing a fluorine atom a group consisting of a combination of -O- and an arylene group containing a fluorine atom, or -NR 10- and -SO.
  • a group consisting of a combination of 2 and an alkylene group containing a fluorine atom is preferable.
  • R 10 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and a hydrogen atom is preferable.
  • the carbon number of the alkylene group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3.
  • These alkylene groups are more preferably perfluoroalkylene groups.
  • Specific examples of the fluorine-substituted alkylene group include a difluoromethylene group, a tetrafluoroethylene group, and a hexafluoropropylene group.
  • the arylene group containing a fluorine atom preferably has 6 to 20 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.
  • Specific examples of the arylene group containing a fluorine atom include a tetrafluorophenylene group, a hexafluoro-1-naphthylene group, a hexafluoro-2-naphthylene group and the like.
  • X 1 represents an anion, -SO 3 -, -COO -, -PO 4 H -, 1 selected from bis (sulfonyl) imide anion, tris (sulfonyl) methide anion and tetraarylborate anion Species are preferred, one selected from bis (sulfonyl) imide anion, tris (sulfonyl) methide anion and tetraarylborate anion is more preferred, and bis (sulfonyl) imide anion or tris (sulfonyl) methide anion is even more preferred.
  • Rtp 1 to Rtp 8 contains an anion
  • L 1 represents a single bond or a divalent linking group, and is preferably a single bond.
  • the divalent linking group represented by L 1 include an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 12 carbon atoms, —O—, —S—, or a group composed of a combination thereof.
  • L 2 represents -SO 2- or -CO-.
  • G represents a carbon atom or a nitrogen atom.
  • n1 represents 2 when G is a carbon atom and represents 1 when G is a nitrogen atom.
  • R 6 represents an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom. If n1 is 2, the two R 6 may each be the same or different.
  • the number of carbon atoms of the alkyl group containing a fluorine atom represented by R 6 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3.
  • the number of carbon atoms of the aryl group containing a fluorine atom represented by R 6 is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 10.
  • substituent T examples include the following groups.
  • Halogen atoms eg, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms
  • alkyl groups preferably alkyl groups with 1 to 30 carbon atoms
  • alkenyl groups preferably alkenyl groups with 2 to 30 carbon atoms
  • alkynyl groups Preferably an alkynyl group having 2 to 30 carbon atoms), an aryl group (preferably an aryl group having 6 to 30 carbon atoms), an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 0 to 30 carbon atoms).
  • alkoxy groups 1 to 30 alkoxy groups
  • aryloxy groups preferably aryloxy groups having 6 to 30 carbon atoms
  • heteroaryloxy groups acyl groups (preferably acyl groups having 2 to 30 carbon atoms), alkoxycarbonyl groups (preferably 2 to 30 carbon atoms).
  • alkoxycarbonyl group having 2 to 30 carbon atoms an alkoxycarbonyl group having 2 to 30 carbon atoms
  • an aryloxycarbonyl group preferably an aryloxycarbonyl group having 7 to 30 carbon atoms
  • a heteroaryloxycarbonyl group an acyloxy group (preferably an acyloxy group having 2 to 30 carbon atoms).
  • Arylamino group preferably acylamino group having 2 to 30 carbon atoms
  • alkoxycarbonylamino group preferably alkoxycarbonylamino group having 2 to 30 carbon atoms
  • aryloxycarbonylamino group preferably 7 to 30 carbon atoms.
  • Aryloxycarbonylamino group preferably sulfamoyl group having 0 to 30 carbon atoms
  • carbamoyl group preferably carbamoyl group having 1 to 30 carbon atoms
  • alkylthio group preferably alkylthio group having 1 to 30 carbon atoms
  • Arylthio groups preferably arylthio groups having 6 to 30 carbon atoms
  • heteroarylthio groups preferably 1 to 30 carbon atoms
  • alkylsulfonyl groups preferably 1 to 30 carbon atoms
  • arylsulfonyl groups preferably 1 to 30 carbon atoms
  • heteroarylsulfonyl groups preferably 1 to 30 carbon atoms
  • alkylsulfinyl groups preferably 1 to 30 carbon atoms
  • arylsulfinyl groups preferably 6 to 30 carbon atoms
  • heteroarylsulfinyl Group preferably 1 to 30 carbon atoms
  • aryled group preferably 1 to 30 carbon atoms
  • hydroxy group carboxyl group, carboxyl group salt, sulfo group, sulfo group salt, phosphoric acid group, phosphoric acid group.
  • Salts carboxylic acid amide groups, sulfonic acid amide groups, imide acid groups, mercapto groups, cyano groups, alkylsulfino groups, arylsulfino groups, hydradino groups, imino groups, heteroaryl groups (preferably 1 to 30 carbon atoms). ..
  • the carboxyl group salt, sulfo group salt, and phosphate group salt the atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K +, etc.) and alkaline earth metal ions (Alkaline earth metal ions).
  • triarylmethane compound examples include the compounds described in JP-A-2016-102191 and the compounds described in Examples described later.
  • Examples of the xanthene compound include a compound represented by the following formula (XT).
  • Rxt 1 , Rxt 2 , Rxt 3 and Rxt 4 each independently represent a hydrogen atom or a substituent, Rxt 5 represents a substituent, and m represents an integer from 0 to 5.
  • X represents a counter anion. In the absence of X, at least one of Rxt 1 to Rxt 5 contains an anion.
  • Substituents that can be taken by Rxt 1 to Rxt 5 in the formula (XT) include the group mentioned in the above-mentioned substituent T, the polymerizable group, and the group represented by the following formula (xt-1). It is preferable that Rxt 1 and Rxt 3 are independently aryl groups or alkyl groups, respectively. Further, it is preferable that Rxt 2 and Rxt 4 are independently hydrogen atoms or alkyl groups, respectively. Further, the above-mentioned alkyl group and aryl group may further have a substituent. Further examples of the substituent include the group mentioned in the above-mentioned substituent T, the polymerizable group, and the group represented by the following formula (xt-1).
  • Rxt 100 represents an alkanediyl group having 1 to 10 carbon atoms
  • -CH 2 constituting the alkanediyl group - is, -O -, - CO -, - NRs 10 -, - OCO -, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted
  • Rs 10 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • Rs 1 to Rs 3 independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
  • * Represents a bond with a nitrogen atom of the formula (XT).
  • Rxt 1 and Rxt 2 , Rxt 3 and Rxt 4 in equation (XT) , and Rxt 5 when m is 2 or more are independently coupled to each other and are 5-, 6-, or 7-membered saturated rings. , Or may form a 5-membered, 6-membered or 7-membered unsaturated ring.
  • Examples of the ring to be formed include a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, a triazole ring, an oxazole ring, a thiazole ring, a pyrrolidine ring, a piperidine ring, a cyclopentene ring, a cyclohexene ring, a benzene ring and a pyridine ring.
  • Examples thereof include a pyrazine ring and a pyridazine ring, preferably a benzene ring and a pyridine ring.
  • the ring formed may further have the group mentioned in the above-mentioned substituent T, the polymerizable group, the group represented by the above-mentioned formula (xt-1), and the like.
  • X represents a counter anion.
  • the counter anion include the counter anion described by the above formula (TP).
  • at least one of Rxt 1 to Rxt 5 contains an anion.
  • the anion when at least one of Rxt 1 to Rxt 5 contains an anion, the anion includes the anion described in the above formula (TP).
  • the xanthene compound is also preferably a compound represented by the formula (XT1) or a compound represented by the formula (XT2).
  • Rxt 11 and Rxt 12 each independently represent a hydrogen atom or an alkyl group
  • Rxt 21 to Rxt 24 each independently represent an alkyl group
  • Rxt 25 to Rxt 27 each independently represent a hydrogen atom.
  • Rxt 31 to Rxt 34 each independently represent an alkyl group
  • Rxt 35 represents a hydrogen atom or a substituent.
  • the alkyl group represented by the formula (XT1) Rxt 11 , Rxt 12 , Rxt 21 , Rxt 22 , Rxt 23 and Rxt 24 preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.
  • the above alkyl group may have a substituent.
  • Examples of the further substituent include the group mentioned in the above-mentioned substituent T, the polymerizable group, and the group represented by the above formula (xt-1), and a carboxyl group is preferable.
  • Examples of the substituent represented by Rxt 25 to Rxt 27 of the formula (XT1) include the group mentioned in the above-mentioned substituent T, the polymerizable group, and the group represented by the above formula (xt-1).
  • the alkyl group represented by the formula (XT2) Rxt 31 to Rxt 34 preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.
  • the above alkyl group may have a substituent.
  • Examples of the further substituent include the group mentioned in the above-mentioned substituent T, the polymerizable group, and the group represented by the above formula (xt-1), and a carboxyl group is preferable.
  • Examples of the substituent represented by Rxt 35 of the formula (XT2) include the group mentioned by the above-mentioned substituent T, the polymerizable group, and the group represented by the above formula (xt-1).
  • xanthene compound examples include the compound described in JP-A-2016-027075, the compound described in JP-A-2016-102191, and paragraph Nos. 0091 to 0109 of International Publication No. 2020/195962. Examples thereof include the compounds described above and the compounds described in Examples described later.
  • Examples of the pyrromethene compound include a compound represented by the formula (PM), a metal complex compound formed from a compound represented by the formula (PM) and a metal or a metal compound, and the like.
  • Rpm 1 to Rpm 6 independently represent a hydrogen atom or a substituent
  • Rpm 7 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • Alkyl groups, aryl groups and heterocyclic groups may have substituents.
  • Examples of the substituents represented by Rpm 1 to Rpm 6 and the substituents that the alkyl group, aryl group and heterocyclic group may have include the group mentioned in the above-mentioned substituent T and the polymerizable group. ..
  • the metal or the metal compound may be any metal atom or metal compound capable of forming a complex with the compound represented by the formula (PM), and is a divalent metal atom or a divalent metal oxide.
  • Examples include divalent metal hydroxides and divalent metal chlorides.
  • pyrromethene compound examples include the compounds described in JP-A-2014-132348 and the compounds described in Examples described later.
  • magenta color dye it is also preferable to use a compound having a polymerizable group.
  • the polymerizable group include an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
  • the magenta color dye is a dye multimer.
  • a dye multimer is a compound having two or more dye structures in one molecule.
  • the dye multimer is preferably a compound having 3 or more dye structures.
  • the upper limit of the number of dye structures is not particularly limited, but may be 100 or less.
  • the weight average molecular weight (Mw) of the dye multimer is preferably 2000 to 50,000.
  • the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
  • the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
  • the dye multimer includes a dye multimer having a repeating unit represented by the formula (A) (hereinafter, also referred to as a dye multimer (A)) and a dye multimer having a repeating unit represented by the formula (B) (hereinafter, also referred to as a dye multimer (A)).
  • a dye multimer also referred to as a dye multimer (B)
  • a dye multimer having a repeating unit represented by the formula (C) hereinafter, also referred to as a dye multimer (C)
  • D dye mass represented by the formula
  • Examples thereof include a body (hereinafter, also referred to as a dye multimer (D)), and a dye multimer (A) or a dye multimer (D) is preferable.
  • the dye multimer (A) contains a repeating unit represented by the formula (A).
  • the ratio of the repeating unit represented by the formula (A) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more of all the repeating units constituting the dye multimer (A). 50% by mass or more is particularly preferable.
  • the upper limit may be 100% by mass or less, or 95% by mass or less.
  • X 1 represents the backbone of the repeating unit
  • L 1 represents a single bond or a divalent linking group
  • D 1 represents the dye structure.
  • X 1 represents the backbone of the repeating unit.
  • Examples of X 1 include a linking group formed by a polymerization reaction, and a main chain derived from a compound having a (meth) acryloyl group, a styrene group, a vinyl group and an ether group is preferable. Further, an embodiment in which the main chain has a cyclic alkylene group is also preferable.
  • X 1 is not particularly limited as long as it is a linking group formed from a known polymerizable monomer.
  • the linking groups represented by the following (XX-1) to (XX-25) are preferable, and (XX-1), (XX-2), (XX-10) to (XX-17), (XX-18). , (XX-19), (XX-24) and (XX-25), more preferably selected from (XX-1), (XX-2), (XX-10) to (XX-17). , (XX-24) and (XX-25) are more preferred.
  • * is a binding site with L 1 in the formula (A).
  • Me represents a methyl group.
  • R in (XX-18) and (XX-19) represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.
  • L 1 represents a single bond or a divalent linking group.
  • -, - COO -, - NR -, - CONR -, - OCO -, - SO -, - SO 2 - is and linking group formed by linking two or more of these and the like.
  • R independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • the alkylene group preferably has 1 to 30 carbon atoms.
  • the upper limit is more preferably 25 or less, and even more preferably 20 or less.
  • the lower limit is more preferably 2 or more, and even more preferably 3 or more.
  • the alkylene group may be linear, branched or cyclic.
  • the alkylene group may have a substituent or may be unsubstituted.
  • the arylene group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the arylene group may have a substituent or may be unsubstituted.
  • the heterocyclic linking group is preferably a 5-membered ring or a 6-membered ring.
  • the hetero atom contained in the heterocyclic linking group is preferably an oxygen atom, a nitrogen atom and a sulfur atom.
  • the number of heteroatoms contained in the heterocyclic linking group is preferably 1 to 3.
  • the heterocyclic linking group may have a substituent or may be unsubstituted.
  • D 1 represents the dye structure.
  • the pigment structure represented by D 1 include a xanthene pigment structure, a pyrromethene pigment structure, a triarylmethane pigment structure, a quinacridone pigment structure, a cyanine pigment structure, an anthraquinone pigment structure, and the like, and include a xanthene pigment structure, a pyrromethene pigment structure, and a triarylmethane. It is preferably a dye structure, and more preferably a xanthene dye structure.
  • the xanthene dye structure is preferably a residue obtained by removing one or more hydrogen atoms from the compound represented by the above formula (XT).
  • the pyrromethene dye structure is preferably a residue obtained by removing one or more hydrogen atoms from the compound represented by the above formula (PM).
  • the triarylmethane dye structure is preferably a residue obtained by removing one or more hydrogen atoms from the compound represented by the above formula (TP).
  • the dye multimer (A) may contain other repeating units in addition to the repeating unit represented by the formula (A).
  • the other repeating unit include a repeating unit having a polymerizable group, a repeating unit having an acid group, and the like.
  • the polymerizable group include an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
  • the acid group include a carboxyl group, a sulfonic acid group, and a phosphoric acid group.
  • the ratio of the repeating unit having a polymerizable group is preferably 50% by mass or less of all the repeating units constituting the dye multimer (A).
  • the lower limit is preferably 1% by mass or more, more preferably 3% by mass or more.
  • the upper limit is preferably 35% by mass or less, more preferably 30% by mass or less.
  • the ratio of the repeating unit having an acid group is preferably 50% by mass or less of all the repeating units constituting the dye multimer (A).
  • the lower limit is preferably 1% by mass or more, more preferably 3% by mass or more.
  • the upper limit is preferably 35% by mass or less, more preferably 30% by mass or less.
  • the dye multimer (B) contains a repeating unit represented by the formula (B).
  • the ratio of the repeating unit represented by the formula (B) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more of all the repeating units constituting the dye multimer (B). 50% by mass or more is particularly preferable.
  • the upper limit may be 100% by mass or less, or 95% by mass or less.
  • X 2 represents the main chain of the repeating unit
  • L 2 represents a single bond or a divalent linking group
  • D 2 represents a dye structure having an ionic bond or a coordinate bond with Y 2.
  • Y 2 represents a group that can be ionic or coordinated to D 2;
  • X 2 has the same meaning as X 1 of the formula (A), and the preferred range is also the same.
  • L 2 represents a single bond or a divalent linking group.
  • R independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • the details of the divalent linking group are the same as those of L 1 of the formula (A).
  • L 2 is preferably a single bond or a alkylene group, an arylene group, -NH-, -CO-, -O-, -COO-, -OCO-, and a divalent linking group in which two or more of these are combined.
  • Y 2 may be a group capable of ionic bond or coordinate bond with D 2.
  • anionic group, cationic group and the like can be mentioned.
  • examples of the anionic group -SO 3 -, -COO -, -PO 4 2-, -PO 4 H -, bis (sulfonyl) imide anion, and tris (sulfonyl) methide anion and tetraarylborate anions.
  • the cationic group include substituted or unsubstituted onium cations (for example, ammonium, pyridinium, imidazolium, phosphonium, etc.), and ammonium cations are particularly preferable.
  • the ammonium cation, -N (R) 3 + and the like Each independently represents a hydrogen atom or an alkyl group, and at least one of R represents an alkyl group.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, and more preferably 1 to 5.
  • the alkyl group may be linear, branched or cyclic, but a linear group is preferable.
  • D 2 represents a dye structure having a group capable of ionic bond or coordinate bond with Y 2.
  • the type of dye structures particularly limited include kinds of dyes structure described in no D 1.
  • Examples of the group of D 2 capable of ionic bond or coordinate bond with Y 2 include the anionic group and the cationic group described in Y 2. Also, if the balance of charge D 2 is biased to one of the cation and anion, the cation portion or the anion portion of the D 2, can also be combined with Y 2.
  • the dye multimer (B) may contain other repeating units described in the dye multimer (A) in addition to the repeating unit represented by the formula (B). Further, the repeating unit represented by the above-mentioned formula (A) and the repeating unit represented by the formula (C) described later may be further included.
  • the dye multimer (C) contains a repeating unit represented by the formula (C).
  • the ratio of the repeating unit represented by the formula (C) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more of all the repeating units constituting the dye multimer (C). 50% by mass or more is particularly preferable.
  • the upper limit may be 100% by mass or less, or 95% by mass or less.
  • L 3 represents a single bond or a divalent linking group
  • D 3 represents a dye structure
  • m represents 0 or 1.
  • L 3 represents a single bond or a divalent linking group.
  • -, - COO -, - NR -, - CONR -, - OCO -, - SO -, - SO 2 - is and linking group formed by linking two or more of these and the like.
  • R independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • the number of carbon atoms of the alkyl group and the alkylene group is preferably 1 to 30.
  • the upper limit is more preferably 25 or less, and even more preferably 20 or less.
  • the lower limit is more preferably 2 or more, and even more preferably 3 or more.
  • the alkyl group and the alkylene group may be linear, branched or cyclic.
  • the aryl group and arylene group preferably have 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the heterocyclic linking group and the heterocyclic group are preferably a 5-membered ring or a 6-membered ring.
  • the heterocyclic linking group and the heteroatom contained in the heterocyclic group are preferably an oxygen atom, a nitrogen atom and a sulfur atom.
  • the number of heteroatoms contained in the heterocyclic linking group and the heterocyclic group is preferably 1 to 3.
  • the alkylene group, arylene group, heterocyclic linking group, alkyl group, aryl group, and heterocyclic group may be unsubstituted or have a substituent. Examples of the substituent include a polymerizable group and an acid group.
  • L 3 represents an alkylene group, an arylene group, -NH -, - CO -, - O -, - COO -, - OCO -, - S- and linking group combining two or more.
  • D 3 represents the dye structure.
  • the type of dye structures, particularly limited include kinds of dyes structure described in no D 1.
  • m represents 0 or 1, and 1 is preferable.
  • the dye multimer (C) may contain other repeating units described in the dye multimer (A) in addition to the repeating unit represented by the general formula (C).
  • the dye multimer (D) is a compound represented by the formula (D).
  • L 4 represents a (n + k) -valent linking group
  • L 41 and L 42 independently represent a single bond or a divalent linking group
  • D 4 represents a dye structure
  • P. 4 represents a substituent
  • n represents 2 to 15, k represents 0 to 13, and n + k represents 2 to 15.
  • n-number of D 4 may be different from each other, it may be identical.
  • k is 2 or more, a plurality of P 4 may be different from each other, it may be identical.
  • N is preferably 2 to 14, more preferably 2 to 8, particularly preferably 2 to 7, and even more preferably 2 to 6.
  • k is preferably 1 to 13, more preferably 1 to 10, still more preferably 1 to 8, particularly preferably 1 to 7, and even more preferably 1 to 6.
  • L 41 and L 42 each independently represent a single bond or a divalent linking group.
  • the divalent linking group includes 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 atoms. It contains a group consisting of up to 20 sulfur atoms and may be unsubstituted or have a further substituent.
  • the divalent linking group may be a group composed of the following structural units or a combination of two or more of the following structural units. * In the following formula represents a bond.
  • the (n + k) valence linking group represented by L 4 includes 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, and 1 to 200 carbon atoms. It contains a group consisting of a hydrogen atom and 0 to 20 sulfur atoms.
  • Examples of the (n + k) -valent linking group include a group composed of the following structural units or a combination of two or more of the following structural units (which may form a ring structure). * In the following formula represents a bond.
  • (n + k) -valent linking group examples include the linking group described in paragraph numbers 0071 to 0072 of JP-A-2008-22950 and the linking group described in paragraph number 0176 of JP-A-2013-029760. Can be mentioned.
  • D 4 represents a dye structure.
  • the type of dye structures, particularly limited include kinds of dyes structure described in no D 1.
  • examples of the substituent represented by P 4 include an acid group and a polymerizable group. Further, the substituent represented by P 4 may be a monovalent polymer chain having a repeating unit.
  • the monovalent polymer chain having a repeating unit is preferably a monovalent polymer chain having a repeating unit derived from a vinyl compound. If k is 2 or more, k number of P 4 may be the same, may be different.
  • magenta dye examples include the compounds described in Examples described later; C. I. Acid Red 1,6,8,9,13,14,18,26,27,32,35,37,42,51,52,57,75,77,80,82,85,87,88,89, 92,94,97,106,111,114,115,117,118,119,129,130,131,133,134,138,143,145,154,155,158,168,180,183,184 186,194,198,209,211,215,219,249,252,254,262,265,274,282,289,303,317,320,321,322, C.I. I.
  • C. I. Food Red 7, 9, 14 and the like can be mentioned.
  • the magenta photosensitive resin composition of the present invention may contain a coloring material having a hue other than the magenta color.
  • a coloring material having a hue other than magenta examples include a green color material, a red color material, a purple color material, a blue color material, an orange color material, and a black color material.
  • the color material having a hue other than magenta may be a pigment or a dye.
  • the content of the coloring material in the total solid content of the magenta photosensitive resin composition is 30% by mass or more, preferably 35% by mass or more, and more preferably 40% by mass or more.
  • the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, from the viewpoint of suppressing development residue, resolution and surface roughness.
  • the total content of the magenta pigment and the magenta dye in the total solid content of the magenta photosensitive resin composition is 30% by mass or more, preferably 35% by mass or more, from the viewpoint of spectral characteristics. It is more preferably 40% by mass or more, and further preferably 45% by mass or more.
  • the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, from the viewpoint of suppressing development residue, resolution and surface roughness.
  • the content of the magenta color dye in the coloring material contained in the magenta color photosensitive resin composition is 20% by mass or more.
  • the content of the magenta color dye in the coloring material is preferably 30% by mass or more, more preferably 40% by mass or more, and more preferably 45% by mass from the viewpoint of spectral characteristics, resolution and suppression of surface roughness.
  • the above is more preferable, 50% by mass or more is further preferable, and 55% by mass or more is particularly preferable.
  • the content of the magenta color dye in the coloring material is preferably 97% by mass or less, more preferably 90% by mass or less, and further preferably 85% by mass or less from the viewpoint of suppressing the development residue. preferable.
  • the ratio of the magenta pigment to the magenta dye in the magenta photosensitive resin composition is magenta with respect to 100 parts by mass of the magenta dye from the viewpoints of spectral characteristics, suppression of development residue, resolution and suppression of surface roughness.
  • the color pigment is preferably 5 to 400 parts by mass.
  • the lower limit is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, further preferably 20 parts by mass or more, and more preferably 30 parts by mass or more from the viewpoint of suppressing the development residue. It is more preferably 50 parts by mass or more, and particularly preferably 50 parts by mass or more.
  • the upper limit is preferably 300 parts by mass or less, more preferably 250 parts by mass or less, still more preferably 200 parts by mass or less, and 150 parts by mass, from the viewpoint of spectral characteristics, resolution and suppression of surface roughness. It is more preferably parts by mass or less, and particularly preferably 100 parts by mass or less.
  • the magenta color photosensitive resin composition does not substantially contain a pigment other than the magenta color pigment (a pigment having a hue other than the magenta color) from the viewpoint of spectral characteristics.
  • a pigment other than the magenta color pigment a pigment having a hue other than the magenta color
  • the content of the magenta color pigment in the pigment contained in the magenta color photosensitive resin composition is 99% by mass or more. That is, it is preferably 99.9% by mass or more, and it is more preferable that the pigment contained in the magenta color photosensitive resin composition is only the magenta color pigment.
  • the magenta color photosensitive resin composition does not substantially contain a dye other than the magenta color dye (a dye having a hue other than the magenta color) from the viewpoint of spectral characteristics.
  • a dye other than the magenta color dye a dye having a hue other than the magenta color
  • the content of the magenta color dye in the dye contained in the magenta color photosensitive resin composition is 99% by mass or more. This means that the content is preferably 99.9% by mass or more, and more preferably the magenta color dye is the only dye contained in the magenta color photosensitive resin composition.
  • the total content of the magenta color pigment and the magenta color dye in the coloring material contained in the magenta color photosensitive resin composition is preferably 40% by mass or more, preferably 50% by mass or more, from the viewpoint of spectral characteristics. It is more preferably 60% by mass or more, further preferably 70% by mass or more, and even more preferably 90% by mass or more. It is particularly preferable that the coloring material contained in the magenta photosensitive resin composition is substantially only a magenta pigment and a magenta dye.
  • the total content of the magenta color pigment and the magenta color dye in the color material is It means that it is 99% by mass or more, preferably 99.9% by mass or more, and more preferably that the coloring material contained in the magenta color photosensitive resin composition is only a magenta color pigment and a magenta color dye. ..
  • the magenta photosensitive resin composition of the present invention preferably contains a pigment derivative.
  • the pigment derivative include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
  • the pigment skeletons constituting the pigment derivatives include quinoline pigment skeleton, benzoimidazolone pigment skeleton, benzoisoindole pigment skeleton, benzothiazole pigment skeleton, iminium pigment skeleton, squarylium pigment skeleton, croconium pigment skeleton, oxonol pigment skeleton, and pyrolopyrrole pigment.
  • Examples of the acid group include a sulfo group, a carboxyl group, a phosphoric acid group and salts thereof.
  • alkali metal ions Li + , Na + , K +, etc.
  • alkaline earth metal ions Ca 2+ , Mg 2+, etc.
  • ammonium ions imidazolium ions, pyridinium ions, etc.
  • Examples include phosphonium ion.
  • Examples of the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimidemethyl group.
  • Examples of the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
  • pigment derivative examples include the compounds described in Examples described later, JP-A-56-118462, JP-A-63-246674, JP-A-01-217077, and JP-A-03-009961.
  • Japanese Patent Laid-Open No. 03-026767 Japanese Patent Application Laid-Open No. 03-153780
  • Japanese Patent Application Laid-Open No. 03-045662 Japanese Patent Application Laid-Open No. 04-285669
  • Japanese Patent Application Laid-Open No. 06-145546 Japanese Patent Application Laid-Open No. 06-212088, Kaihei 06-240158
  • Japanese Patent Laid-Open No. 10-030063 Japanese Patent Laid-Open No. 10-195326
  • Paragraph Nos Japanese Patent Laid-Open Nos.
  • the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the magenta color pigment.
  • the total content of the magenta color pigment and the pigment derivative is preferably 5.1 to 520 parts by mass, more preferably 20 to 300 parts by mass with respect to 100 parts by mass of the magenta color dye. It is preferably 50 to 130 parts by mass, and more preferably 50 to 130 parts by mass.
  • the magenta photosensitive resin composition of the present invention contains a resin.
  • the resin is blended, for example, for the purpose of dispersing a pigment or the like in a magenta-color photosensitive resin composition or for a binder.
  • a resin mainly used for dispersing a pigment or the like in a magenta photosensitive resin composition is also referred to as a dispersant.
  • such an application of the resin is an example, and the resin can be used for purposes other than such an application.
  • the weight average molecular weight (Mw) of the resin is preferably 2000 to 2000000.
  • the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
  • the lower limit is preferably 3000 or more, and more preferably 5000 or more.
  • the resin examples include (meth) acrylic resin, epoxy resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide resin.
  • examples thereof include polyamide imide resin, polyolefin resin, cyclic olefin resin, polyester resin, and styrene resin. One of these resins may be used alone, or two or more thereof may be mixed and used.
  • the magenta photosensitive resin composition of the present invention preferably contains a resin having an acid group.
  • the acid group include a carboxyl group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. These acid groups may be only one kind or two or more kinds.
  • the resin having an acid group can also be used as a dispersant. Further, as the resin having an acid group, the alkali-soluble resin described in JP-A-2017-173787 can also be used.
  • the acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g.
  • the lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more.
  • the upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, further preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
  • the magenta photosensitive resin composition of the present invention preferably contains a resin having a basic group.
  • the resin having a basic group is preferably a resin containing a repeating unit having a basic group in the side chain, and has both a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group.
  • a polymer is more preferable, and a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group is further preferable.
  • a resin having a basic group can also be used as a dispersant.
  • the amine value of the resin having a basic group is preferably 5 to 300 mgKOH / g.
  • the lower limit is preferably 10 mgKOH / g or more, and more preferably 20 mgKOH / g or more.
  • the upper limit is preferably 200 mgKOH / g or less, and more preferably 100 mgKOH / g or less.
  • Examples of the basic group contained in the resin having a basic group include a group represented by the following formula (a-1) and a group represented by the following formula (a-2).
  • Ra1 and Ra2 each independently represent a hydrogen atom, an alkyl group or an aryl group, and Ra1 and Ra2 may be bonded to each other to form a ring;
  • R a11 represents a hydrogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxy radical
  • R a12 ⁇ R a19 are each independently , Hydrogen atom, alkyl group or aryl group.
  • R a1, R a2, R a11 number of carbon atoms of the alkyl group represented by ⁇ R a19 is 1-30, more preferably 1-15, more preferably 1-8, particularly preferably 1-5.
  • the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
  • the alkyl group may have a substituent.
  • R a1, R a2, R a11 ⁇ number of carbon atoms of the aryl group R a19 represents is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
  • the aryl group may have a substituent.
  • the number of carbon atoms of the alkoxy group R a11 represents 1 to 30, more preferably 1 to 15, more preferably 1-8, particularly preferably 1-5.
  • the alkoxy group may have a substituent.
  • the aryloxy group represented by R a11 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
  • the aryloxy group may have a substituent.
  • the number of carbon atoms of the acyl group represented by R a11 is preferably 2 to 30, more preferably 2 to 20, and even more preferably 2 to 12.
  • the acyl group may have a substituent.
  • the resin having a basic group is described in the block copolymers (B) described in paragraphs 0063 to 0112 of JP2014-219665A and paragraphs 0046 to 0076 of JP-A-2018-156021.
  • the block copolymer A1 which has been prepared can also be used, and the contents thereof are incorporated in the present specification.
  • the magenta photosensitive resin composition of the present invention contains a resin having an acid group and a resin having a basic group, respectively. According to this aspect, the storage stability of the magenta photosensitive resin composition can be further improved.
  • the content of the resin having a basic group may be 20 to 500 parts by mass with respect to 100 parts by mass of the resin having an acid group. It is preferably 30 to 300 parts by mass, more preferably 50 to 200 parts by mass.
  • the resin contains a repeating unit derived from a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as “ether dimer”). It is also preferable to contain a resin.
  • R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
  • R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
  • the description in JP-A-2010-168539 can be referred to.
  • paragraph number 0317 of JP2013-209760A can be referred to, and this content is incorporated in the present specification.
  • the resin contains a resin containing a repeating unit having a polymerizable group.
  • the resin preferably contains a resin containing a repeating unit derived from the compound represented by the formula (X).
  • R 1 represents a hydrogen atom or a methyl group
  • R 21 and R 22 each independently represent an alkylene group
  • n represents an integer of 0 to 15.
  • the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, further preferably 1 to 3 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
  • n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
  • Examples of the compound represented by the formula (X) include ethylene oxide of paracumylphenol or propylene oxide-modified (meth) acrylate.
  • Examples of commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
  • the resin contains a resin having an aromatic carboxyl group (hereinafter, also referred to as resin Ac).
  • the aromatic carboxyl group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
  • the aromatic carboxyl group is preferably contained in the main chain of the repeating unit.
  • an aromatic carboxyl group is a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring.
  • the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
  • the resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (Ac-1) and the repeating unit represented by the formula (Ac-2).
  • Ar 1 represents a group containing an aromatic carboxyl group
  • L 1 represents -COO- or -CONH-
  • L 2 represents a divalent linking group
  • Ar 10 represents a group containing an aromatic carboxyl group
  • L 11 represents -COO- or -CONH-
  • L 12 represents a trivalent linking group
  • P 10 represents a polymer. Represents a chain.
  • Examples of the group containing an aromatic carboxyl group represented by Ar 1 in the formula (Ac-1) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like.
  • Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.
  • Q 1 is represented by a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , and the following formula (Q-1). Represents a group to be used or a group represented by the following formula (Q-2).
  • the group containing an aromatic carboxyl group represented by Ar 1 may have a polymerizable group.
  • the polymerizable group is preferably an ethylenically unsaturated bond-containing group or a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group.
  • Specific examples of the group containing an aromatic carboxyl group represented by Ar 1 include a group represented by the formula (Ar-11), a group represented by the formula (Ar-12), and a group represented by the formula (Ar-13). Examples include the base.
  • n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
  • n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
  • n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
  • Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , the above formula (Q-). It represents a group represented by 1) or a group represented by the above formula (Q-2).
  • L 1 represents -COO- or -CONH-, and preferably -COO-.
  • the divalent linking group represented by L 2 in the formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these.
  • a group that combines two or more of the above can be mentioned.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched or cyclic.
  • the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
  • the alkylene group and the arylene group may have a substituent.
  • the substituent include a hydroxy group and the like.
  • the divalent linking group L 2 represents is preferably a group represented by -L 2a -O-.
  • L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group, and —O—, —CO—, —COO—, —OCO—, Examples thereof include a group in which at least one selected from —NH— and —S— is combined, and an alkylene group is preferable.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched or cyclic.
  • the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and the like.
  • the group containing the aromatic carboxyl group represented by Ar 10 in the formula (Ac-2) has the same meaning as Ar 1 in the formula (Ac-1), and the preferred range is also the same.
  • L 11 represents -COO- or -CONH-, and preferably -COO-.
  • the trivalent linking group represented by L 12 in the formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and two of these.
  • a group that combines species or more can be mentioned.
  • the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
  • the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic.
  • the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
  • the hydrocarbon group may have a substituent.
  • substituent include a hydroxy group and the like.
  • the trivalent linking group represented by L 12 is preferably a group represented by the formula (L12-1), and more preferably a group represented by the formula (L12-2).
  • L 12b represents a trivalent linking group
  • X 1 represents S
  • * 1 represents the bonding position with L 11 in the formula (Ac-2)
  • * 2 represents the bonding position with L 11 in the formula (Ac-2). It represents a bonding position to P 10 of the Ac-2).
  • the trivalent linking group represented by L 12b is a hydrocarbon group; a hydrocarbon group and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-. Examples thereof include a group in which the above is combined with, and a hydrocarbon group or a group in which a hydrocarbon group and —O— are combined is preferable.
  • L 12c represents a trivalent linking group
  • X 1 represents S
  • * 1 represents the bonding position with L 11 of the formula (Ac-2)
  • * 2 represents the binding position of the formula (L12-2). It represents a bonding position to P 10 of the Ac-2).
  • the trivalent linking group represented by L 12c is a hydrocarbon group; a hydrocarbon group and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-. Examples thereof include a group in which the above is combined, and a hydrocarbon group is preferable.
  • P 10 represents a polymer chain.
  • the polymer chain represented by P 10 preferably has at least one repeating unit selected from poly (meth) acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
  • the weight average molecular weight of the polymer chain P 10 is preferably 500 to 20000.
  • the lower limit is preferably 1000 or more.
  • the upper limit is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
  • the weight average molecular weight of P 10 is in the above range, the dispersibility of the pigment in the composition is good.
  • the resin having an aromatic carboxyl group is a resin having a repeating unit represented by the formula (Ac-2), this resin is preferably used as a dispersant.
  • the resin preferably contains a resin as a dispersant.
  • the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
  • the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
  • the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol% or more is preferable when the total amount of the acid group and the basic group is 100 mol%.
  • the acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group.
  • the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g.
  • the basic dispersant represents a resin in which the amount of basic groups is larger than the amount of acid groups.
  • a resin in which the amount of basic groups exceeds 50 mol% is preferable when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
  • the basic group contained in the basic dispersant is preferably an amino group.
  • the resin used as the dispersant is a graft resin.
  • the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the contents thereof are incorporated in the present specification.
  • the resin used as the dispersant is also preferably a resin having an aromatic carboxyl group (resin Ac).
  • resin Ac resin having an aromatic carboxyl group
  • examples of the resin having an aromatic carboxyl group include those described above.
  • the resin used as the dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
  • the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
  • the resin to have is preferable.
  • the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
  • the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
  • the resin used as the dispersant is a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
  • resins include dendrimers (including star-shaped polymers).
  • specific examples of the dendrimer include the polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
  • the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain.
  • the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and 20 to 70 in all the repeating units of the resin. It is more preferably mol%.
  • the resin described in JP-A-2018-087939 can also be used as the dispersant.
  • Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by Big Chemie Japan, SOLSPERSE series manufactured by Japan Lubrizol, Efka series manufactured by BASF, and Ajinomoto Fine Techno (Ajinomoto Fine Techno). Examples include the Ajispar series manufactured by Co., Ltd. Further, the product described in paragraph number 0129 of JP2012-137564A and the product described in paragraph number 0235 of JP2017-194662 can also be used as a dispersant.
  • the dispersant includes block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, and resins described in JP-A-2018-087939.
  • Polymers, block polymers having an acrylamide structural unit described in JP-A-2020-066688, dispersants described in International Publication No. 2016/104803, and the like can also be used.
  • the content of the resin in the total solid content of the magenta photosensitive resin composition is preferably 1 to 60% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
  • the magenta color photosensitive resin composition of the present invention may contain only one kind of resin, or may contain two or more kinds of resins. When two or more kinds of resins are contained, it is preferable that the total amount thereof is within the above range.
  • the magenta photosensitive resin composition of the present invention contains a polymerizable compound.
  • a polymerizable compound a known compound that can be crosslinked by radicals, acids or heat can be used.
  • the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond-containing group.
  • the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
  • the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
  • the polymerizable compound may be in any chemical form such as a monomer, a prepolymer or an oligomer, but a monomer is preferable.
  • the molecular weight of the polymerizable compound is preferably 100 to 3000.
  • the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
  • the lower limit is more preferably 150 or more, and even more preferably 250 or more.
  • the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and more preferably an ethylenically unsaturated bond. It is more preferable that the compound contains 3 to 6 containing groups. Further, the polymerizable compound is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
  • polymerizable compound examples include paragraph numbers 0995 to 0108 of JP2009-288705, paragraphs 0227 of JP2013-029760, paragraphs 0254 to 0257 of JP2008-292970, and JP-A.
  • the compounds described in paragraph numbers 0034 to 0038 of Japanese Patent Application Laid-Open No. 2013-253224, paragraph numbers 0477 of Japanese Patent Application Laid-Open No. 2012-208494, Japanese Patent Application Laid-Open No. 2017-048637, Japanese Patent No. 6057891 and Japanese Patent Application Laid-Open No. 6031807 are These contents are incorporated herein by reference.
  • dipentaerythritol tri (meth) acrylate commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.
  • dipentaerythritol tetra (meth) acrylate commercially available KAYARAD D-320.
  • diglycerin EO ethylene oxide modified (meth) acrylate
  • pentaerythritol tetraacrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd., NK ester A
  • 1,6-hexanediol diacrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA
  • RP-1040 manufactured by Nippon Kayaku Co., Ltd.
  • Aronix TO-2349 manufactured by Toa Synthetic Co., Ltd.
  • NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • DPHA-40H manufactured by Nippon Kayaku Co., Ltd.
  • Examples of the polymerizable compound include trimethylolpropane tri (meth) acrylate, trimethylolpropane propylene oxide modified tri (meth) acrylate, trimethylolpropane ethylene oxide modified tri (meth) acrylate, and isocyanuric acid ethylene oxide modified tri (meth) acrylate.
  • Trifunctional (meth) acrylate compounds such as pentaerythritol tri (meth) acrylate can also be used.
  • Commercially available trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
  • M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
  • a compound having an acid group can also be used as the polymerizable compound.
  • the polymerizable compound having an acid group By using a polymerizable compound having an acid group, the polymerizable compound in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
  • the acid group include a carboxyl group, a sulfo group, a phosphoric acid group and the like, and a carboxyl group is preferable.
  • Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
  • the preferable acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
  • the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when the acid value is 40 mgKOH / g or less, it is advantageous in production and handling.
  • a compound having a caprolactone structure can also be used.
  • examples of commercially available products of the polymerizable compound having a caprolactone structure include KAYARAD DPCA-20, DPCA-30, DPCA-60, DPCA-120 (all manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • a polymerizable compound having an alkyleneoxy group can also be used.
  • a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group is preferable, a polymerizable compound having an ethyleneoxy group is more preferable, and 3 to 3 having 4 to 20 ethyleneoxy groups.
  • a hexafunctional (meth) acrylate compound is more preferred.
  • Examples of the polymerizable compound having an alkyleneoxy group include compounds having the following structures.
  • SR-494 which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer, and a trifunctional (meth) having three isobutyleneoxy groups.
  • KAYARAD TPA-330 which is an acrylate and the like can be mentioned.
  • a polymerizable compound having a fluorene skeleton can also be used.
  • examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
  • the polymerizable compound it is also preferable to use a compound that does not substantially contain an environmentally regulatory substance such as toluene.
  • an environmentally regulatory substance such as toluene.
  • commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
  • the content of the polymerizable compound in the total solid content of the magenta photosensitive resin composition is preferably 0.1 to 50% by mass.
  • the lower limit is more preferably 0.5% by mass or more, further preferably 1% by mass or more.
  • the upper limit is more preferably 45% by mass or less, further preferably 40% by mass or less.
  • the polymerizable compound only one kind may be used, or two or more kinds may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the magenta photosensitive resin composition of the present invention contains a solvent.
  • the solvent include organic solvents.
  • the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
  • the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, hydrocarbon-based solvents and the like.
  • an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
  • the organic solvent include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol acetate, butylcarbi Tall acetate, propylene glycol
  • aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 parts by mass (parts) with respect to the total amount of organic solvent. Per millision) or less, 10 mass ppm or less, or 1 mass ppm or less).
  • an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per tension) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015). ..
  • Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
  • the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
  • the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
  • the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
  • the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
  • the content of the solvent in the magenta photosensitive resin composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and further preferably 30 to 90% by mass.
  • the magenta color photosensitive resin composition of the present invention does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulations.
  • substantially free of the environmentally regulated substance means that the content of the environmentally regulated substance in the magenta color photosensitive resin composition is 50 mass ppm or less, and is 30 mass ppm or less. It is preferably abundant, more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
  • the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
  • REACH Registration Evolution Analysis and Restriction of Chemicals
  • PRTR Policy Release and Transfer Register
  • VOC Volatile and Transfer Registor
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • a method for reducing the environmentally regulated substance there is a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance or higher and distilling off the environmentally regulated substance from the system to reduce the amount. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the corresponding solvent in order to improve efficiency.
  • a polymerization inhibitor or the like is added and the mixture is distilled off under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. May be.
  • distillation methods are performed at the stage of the raw material, the stage of the product obtained by reacting the raw material (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a magenta color photosensitive resin prepared by mixing these compounds. It can be done at any stage, such as at the composition stage.
  • the magenta photosensitive resin composition of the present invention preferably contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
  • the photopolymerization initiator is preferably a photoradical polymerization initiator.
  • photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
  • the photopolymerization initiator is a trihalomethyltriazine compound, a benzyldimethylketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, or a triarylimidazole.
  • It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound and a 3-aryl substituted coumarin compound, preferably an oxime compound and an ⁇ -hydroxyketone compound.
  • ⁇ -Aminoketone compound, and a compound selected from an acylphosphine compound are more preferable, and an oxime compound is further preferable.
  • the photopolymerization initiator the compound described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol. 19, No. Peroxide-based photopolymerization initiator described in 3, 2019, photopolymerization initiator described in International Publication No. 2018/221177, photopolymerization initiator described in International Publication No. 2018/110179, JP-A-2019-043864.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (above, IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure27, Irgacure29. (Manufactured by the company) and the like.
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369, Irger Made) and so on.
  • acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
  • Examples of the oxime compound include the compound described in JP-A-2001-233842, the compound described in JP-A-2000-080068, the compound described in JP-A-2006-342166, and J. Am. C. S. The compound according to Perkin II (1979, pp. 1653-1660), J. Mol. C. S. The compound described in Perkin II (1979, pp. 156-162), the compound described in Journal of Photopolisr Science and Technology (1995, pp. 202-232), the compound described in JP-A-2000-066385, the compound described in JP-A-2000-066385.
  • oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyimiminopentane-3-one, and the like.
  • an oxime compound having a fluorene ring can also be used.
  • Specific examples of the oxime compound having a fluorene ring include the compound described in JP-A-2014-137466 and the oxime compound having a fluorene ring and a nitro group described in Japanese Patent No. 6636081.
  • an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
  • Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
  • an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
  • Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471.
  • Compound (C-3) and the like can be mentioned.
  • an oxime compound having a nitro group can be used as the photopolymerization initiator.
  • the oxime compound having a nitro group is also preferably a dimer.
  • Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP-A-2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARCULDS NCI-831 (manufactured by ADEKA Corporation).
  • an oxime compound having a benzofuran skeleton can also be used.
  • Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
  • an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
  • Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
  • the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
  • the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, still more preferably 2000 to 300,000, and more preferably 5000 to 200,000. It is particularly preferable to have.
  • the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
  • Irgacure OXE01 manufactured by BASF
  • Irgacure OXE02 manufactured by BASF
  • Omnirad 2959 manufactured by IGM Resins BV
  • a bifunctional or trifunctional or higher photoradical polymerization initiator may be used as the photopolymerization initiator.
  • two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
  • the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the magenta photosensitive resin composition with time is improved.
  • Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No.
  • the photoinitiator described in paragraphs 0020 to 0033, the photopolymerization initiator (A) described in paragraphs 0017 to 0026 of JP-A-2017-151342, is described in Japanese Patent No. 6469669.
  • Examples include oxime ester photoinitiators.
  • the content of the photopolymerization initiator in the total solid content of the magenta photosensitive resin composition is preferably 0.1 to 30% by mass.
  • the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
  • the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. Only one kind of photopolymerization initiator may be used, or two or more kinds may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the magenta photosensitive resin composition of the present invention can contain a compound having a cyclic ether group.
  • the cyclic ether group include an epoxy group and an oxetanyl group.
  • the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound). Examples of the epoxy compound are described in paragraphs 0034 to 0036 of JP2013-011869, paragraph numbers 0147 to 0156 of JP2014-0435556, and paragraph numbers 0083 to 0092 of JP2014-089408. Compounds, compounds described in JP-A-2017-179172 can also be used. These contents are incorporated herein.
  • the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 2000, further, a molecular weight of less than 1000), or a polymer compound (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). But it may be.
  • the weight average molecular weight of the epoxy compound is preferably 200 to 100,000, more preferably 500 to 50,000.
  • the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
  • an epoxy resin can be preferably used as the epoxy compound.
  • the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenol compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, and a glycidyl ester.
  • Examples thereof include a copolymer with another polymerizable unsaturated compound.
  • the epoxy equivalent of the epoxy resin is preferably 310 to 3300 g / eq, more preferably 310 to 1700 g / eq, and even more preferably 310 to 1000 g / eq.
  • EHPE3150 manufactured by Daicel Corporation
  • EPICLON N-695 manufactured by DIC Corporation
  • Marproof G-0150M G-0105SA, G-0130SP, G. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all manufactured by NOF CORPORATION, epoxy group-containing polymer) and the like can be mentioned.
  • the content of the compound having a cyclic ether group in the total solid content of the magenta color photosensitive resin composition is preferably 0.1 to 20% by mass.
  • the lower limit is, for example, preferably 0.5% by mass or more, and more preferably 1% by mass or more.
  • the upper limit is, for example, preferably 15% by mass or less, and more preferably 10% by mass or less.
  • the compound having a cyclic ether group only one kind may be used, or two or more kinds may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the magenta photosensitive resin composition of the present invention may contain a curing accelerator.
  • the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidin salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
  • Specific examples of the curing accelerator include the compound described in paragraph Nos. 0094 to 0097 of International Publication No. 2018/056189, the compound described in paragraph numbers 0246 to 0253 of JP-A-2015-034963, and JP-A-2013-041165. Compounds described in Japanese Patent Laid-Open No.
  • the curing accelerator when the curing accelerator is contained, the content of the curing accelerator in the total solid content of the magenta photosensitive resin composition is preferably 0.3 to 8.9% by mass, preferably 0.8 to 6.4% by mass. More preferred.
  • the magenta photosensitive resin composition of the present invention can contain an ultraviolet absorber.
  • an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound and the like can be used. Examples of such compounds include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-066814.
  • the compounds described in paragraphs 0061 to 0080 of JP 2016-162946 are mentioned, the contents of which are incorporated herein by reference.
  • Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of commercially available products of the ultraviolet absorber include UV-503 (manufactured by Daito Kagaku Co., Ltd.), Tinuvin series manufactured by BASF, and Uvinul series. Examples of the benzotriazole compound include the MYUA series made of Miyoshi Oil & Fat (The Chemical Daily, February 1, 2016). Further, the ultraviolet absorber is a compound described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967, a compound described in paragraph numbers 0059 to 0076 of International Publication No. 2016/181987, and International Publication No. 2020/137819. The thioaryl group-substituted benzotriazole type ultraviolet absorber described in 1 can also be used.
  • the content of the ultraviolet absorber in the total solid content of the magenta photosensitive resin composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
  • the content of the ultraviolet absorber in the total solid content of the magenta photosensitive resin composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
  • only one kind of ultraviolet absorber may be used, or two or more kinds may be used. When two or more kinds are used, it is preferable that the total amount is within the above range.
  • the magenta photosensitive resin composition of the present invention can contain a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like.
  • examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, first cerium salt, etc.). Of these, p-methoxyphenol is preferable.
  • the content of the polymerization inhibitor in the total solid content of the magenta photosensitive resin composition is preferably 0.0001 to 5% by mass.
  • the polymerization inhibitor may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the magenta photosensitive resin composition of the present invention can contain a silane coupling agent.
  • the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
  • the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
  • the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
  • a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
  • silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino.
  • Propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -Aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxy There are propylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co
  • the silane coupling agent examples include the compounds described in paragraphs 0018 to 0036 of JP2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. , These contents are incorporated herein.
  • the content of the silane coupling agent in the total solid content of the magenta photosensitive resin composition is preferably 0.01 to 15.0% by mass, preferably 0.05 to 10.0. % By mass is more preferred.
  • the silane coupling agent may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the magenta photosensitive resin composition of the present invention can contain a surfactant.
  • a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
  • the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant.
  • the surfactant include the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/16677, and the surfactant described in JP-A-2020-008634, the contents of which are described in the present specification. Incorporated into the book.
  • the liquid characteristics can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
  • the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. Fluorine-based surfactants having a fluorine content within this range are effective in terms of uniformity of coating film thickness and liquid saving, and have good solubility in magenta-color photosensitive resin compositions. be.
  • fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, Japanese Patent Application Laid-Open No. 2011-.
  • the surfactants described in paragraphs 0117 to 0132 of the Publication No. 132503 are mentioned and their contents are incorporated herein by reference.
  • Commercially available products of fluorine-based surfactants include, for example, Megafuck F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144.
  • the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
  • a fluorine-based surfactant include the Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega. Fuck DS-21 can be mentioned.
  • fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
  • a fluorine-based surfactant include the fluorine-based surfactants described in JP-A-2016-216602, the contents of which are incorporated in the present specification.
  • the fluorine-based surfactant a block polymer can also be used.
  • the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
  • a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
  • the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
  • the weight average molecular weight of the above compounds is preferably 3000 to 50,000, for example 14000.
  • % indicating the ratio of the repeating unit is mol%.
  • a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used. Specific examples thereof include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP2010-164965, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation. RS-72-K and the like can be mentioned. Further, as the fluorine-based surfactant, the compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
  • a fluorine-containing imide salt compound represented by the formula (fi-1) is also preferable to use as a surfactant.
  • m represents 1 or 2
  • n represents an integer of 1 to 4
  • a represents 1 or 2
  • X a + represents an a-valent metal ion, a primary ammonium ion, and a first.
  • secondary ammonium ion represents a tertiary ammonium ion, a quaternary ammonium ion or NH 4 +.
  • Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, etc.
  • silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400, and FZ-2122.
  • Dow Corning Co., Ltd. TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials), KP-341, KF-6001, KF- Examples include 6002 (above, manufactured by Shin-Etsu Chemical Industry Co., Ltd.), BYK307, BYK323, BYK330 (above, manufactured by Big Chemie) and the like.
  • the content of the surfactant in the total solid content of the magenta photosensitive resin composition is preferably 0.001% by mass to 5.0% by mass, preferably 0.005 to 3.0. % By mass is more preferred.
  • the surfactant may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the magenta photosensitive resin composition of the present invention can contain an antioxidant.
  • the antioxidant include a phenol compound, a phosphite ester compound, a thioether compound and the like.
  • the phenol compound any phenol compound known as a phenolic antioxidant can be used.
  • Preferred phenolic compounds include hindered phenolic compounds.
  • a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
  • a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
  • the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used.
  • the content of the antioxidant in the total solid content of the magenta photosensitive resin composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. When containing an antioxidant, only one type of antioxidant may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount is within the above range.
  • the magenta color photosensitive resin composition of the present invention may be used as a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, a filler, etc.), if necessary. It may contain an antifoaming agent, a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension adjusting agent, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraph No. 0183 or later of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No.
  • magenta photosensitive resin composition of the present invention may contain a latent antioxidant, if necessary.
  • the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. This includes compounds in which the protecting group is desorbed and functions as an antioxidant. Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
  • magenta photosensitive resin composition of the present invention may contain an aromatic group-containing phosphonium salt described in JP-A-2020-079833.
  • the magenta photosensitive resin composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
  • the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
  • the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, still more preferably 5 to 50 nm.
  • the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
  • the magenta color photosensitive resin composition of the present invention may contain a light resistance improving agent.
  • the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
  • perfluoroalkyl sulfonic acid and its salt and perfluoroalkyl carboxylic acid and its salt may be restricted.
  • perfluoroalkyl sulfonic acid particularly, perfluoroalkyl sulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
  • perfluoroalkyl sulfonic acid thereof are used.
  • the content of the salt, the perfluoroalkylcarboxylic acid (particularly the perfluoroalkylcarboxylic acid having 6 to 8 perfluoroalkyl group carbon atoms) and the salt thereof is based on the total solid content of the magenta-color photosensitive resin composition. It is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb.
  • the magenta photosensitive resin composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and salts thereof, as well as perfluoroalkylcarboxylic acid and salts thereof.
  • the magenta photosensitive resin composition of the present invention may contain a perfluoroalkyl sulfonic acid and a salt thereof, and a perfluoroalkyl carboxylic acid and a salt thereof within the maximum allowable range.
  • the water content of the magenta photosensitive resin composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and preferably in the range of 0.1 to 1.0% by mass. More preferred.
  • the water content can be measured by the Karl Fischer method.
  • the magenta color photosensitive resin composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface (flatness, etc.), adjusting the film thickness, and the like.
  • the viscosity value can be appropriately selected as needed, but for example, at 25 ° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
  • a method for measuring the viscosity for example, a cone plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25 ° C.
  • the storage container for the magenta photosensitive resin composition of the present invention is not particularly limited, and a known storage container can be used.
  • a storage container for the purpose of suppressing impurities from being mixed into raw materials and compositions, a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used. It is also preferable to use it. Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351.
  • magenta photosensitive resin composition of the present invention can be prepared by mixing the above-mentioned components.
  • all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare a magenta-color photosensitive resin composition, or if necessary, each component may be appropriately 2
  • a magenta photosensitive resin composition may be prepared by preparing two or more solutions or dispersions and mixing them at the time of use (at the time of application).
  • the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
  • Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
  • the process and disperser for dispersing pigments are "Dispersion Technology Complete Works, Published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial”. Practical application The process and disperser described in Paragraph No.
  • JP-A-2015-157893 "Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used.
  • the particles may be miniaturized in the salt milling step.
  • the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
  • any filter that has been conventionally used for filtration or the like can be used without particular limitation.
  • fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
  • polyamide resins such as nylon (eg, nylon-6, nylon-6,6)
  • polyolefin resins such as polyethylene and polypropylene (PP)
  • PP polypropylene
  • a filter using a material such as (including a high-density, ultra-high molecular weight polyolefin resin) can be mentioned.
  • polypropylene including high-density polypropylene
  • nylon are preferable.
  • the pore diameter of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
  • the nominal value of the filter manufacturer can be referred to.
  • various filters provided by Nippon Pole Co., Ltd. DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.
  • Advantech Toyo Co., Ltd. Japan Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc.
  • KITZ Microfilter Co., Ltd. etc.
  • a fiber-like filter medium As the filter.
  • the fiber-like filter medium include polypropylene fiber, nylon fiber, glass fiber and the like.
  • examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by Roki Techno Co., Ltd.
  • filters different filters (eg, first filter and second filter, etc.) may be combined. At that time, the filtration with each filter may be performed only once or twice or more. Further, filters having different pore diameters may be combined within the above-mentioned range. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter.
  • the film of the present invention is a film obtained from the magenta color photosensitive resin composition of the present invention described above.
  • the film of the present invention can be used as a color filter. More specifically, it can be used for magenta color pixels of a color filter.
  • the film thickness of the film of the present invention can be appropriately adjusted depending on the intended purpose.
  • the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even 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, still more preferably 0.3 ⁇ m or more.
  • the maximum value of the light transmittance in the wavelength range of 400 to 500 nm of the film of the present invention is preferably 70% or more, more preferably 75% or more, still more preferably 80% or more.
  • the minimum value of the light transmittance in the wavelength range of 450 to 600 nm of the film of the present invention is preferably 30% or less, more preferably 20% or less, still more preferably 15% or less. It is particularly preferably 10% or less.
  • the maximum value of the light transmittance in the wavelength range of 550 to 700 nm of the film of the present invention is preferably 70% or more, more preferably 80% or more, still more preferably 90% or more. ..
  • the film of the present invention has a wavelength in which the light transmittance is 50% in the wavelength range of 450 to 500 nm and in the wavelength range of 550 to 600 nm.
  • the wavelength on the short wave side showing a light transmittance of 50% preferably exists in the wavelength range of 460 to 495 nm, more preferably exists in the wavelength range of 470 to 495 nm, and exists in the wavelength range of 475 to 495 nm. Is particularly preferred.
  • the wavelength on the long wave side where the light transmittance is 50% is preferably in the wavelength range of 560 to 595 nm, and more preferably in the wavelength range of 570 to 590 nm.
  • a film having such spectral characteristics is preferably used as a magenta color pixel.
  • the color filter of the present invention has the above-mentioned film of the present invention.
  • the color filter of the present invention preferably has the film of the present invention as magenta color pixels of the color filter. Further, it is also preferable that the color filter of the present invention has a magenta color pixel, a cyan color pixel, and a yellow pixel obtained by using the magenta color photosensitive resin composition of the present invention described above.
  • the cyan pixel preferably contains the color index pigment green 7.
  • the cyan pixel has a maximum transmittance of 90% or more for light in the wavelength range of 450 to 550 nm and a minimum value of 20% or less for the transmittance of light in the wavelength range of 615 to 645 nm. It is preferable that the wavelength showing 50% exists in each of the wavelength range of 395 to 415 nm and the wavelength range of 560 to 580 nm.
  • the yellow pixels preferably include the Color Index Pigment Yellow 150. Further, in the yellow pixel, the maximum value of the light transmittance in the wavelength range of 500 to 700 nm is 90% or more, and the minimum value of the light transmittance in the wavelength range of 415 to 445 nm is 10% or less, and the transmittance is 50.
  • the color filter of the present invention can be used for a solid-state image pickup device such as a CCD (charge-coupled device) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
  • a CCD charge-coupled device
  • CMOS complementary metal oxide semiconductor
  • the film thickness of the film can be appropriately adjusted according to the purpose.
  • the film thickness is preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less, and even more preferably 0.6 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
  • the width of the pixels included in the color filter is preferably 0.2 to 10.0 ⁇ m.
  • the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and further preferably 0.6 ⁇ m or more.
  • the upper limit is preferably 5.0 ⁇ m or less, more preferably 2.0 ⁇ m or less, further preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
  • the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
  • each pixel included in the color filter has high flatness.
  • the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
  • the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
  • the surface roughness of the pixel can be measured using, for example, an AFM (atomic force microscope) Measurement 3100 manufactured by Veeco.
  • the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
  • the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
  • the volume resistance value of the pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest).
  • a protective layer may be provided on the surface of the film (pixel) of the present invention.
  • various functions such as oxygen blocking, low reflection, prohydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
  • the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
  • Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
  • the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
  • Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4, and the like, and two or more of these components may be contained.
  • the protective layer for the purpose of blocking oxygen, it is preferable that the protective layer contains a polyol resin, SiO 2 , and Si 2 N 4. Further, in the case of a protective layer for the purpose of reducing reflection, it is preferable that the protective layer contains a (meth) acrylic resin and a fluororesin.
  • the resin composition When the resin composition is applied to form the protective layer, known methods such as a spin coating method, a casting method, a screen printing method, and an inkjet method can be used as the application method of the resin composition.
  • a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
  • the protective layer is formed by the chemical vapor deposition method, the known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method) is used as the chemical vapor deposition method. Can be used.
  • the protective layer may be an additive such as organic / inorganic fine particles, an absorber for light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjusting agent, an antioxidant, an adhesive, and a surfactant, if necessary. May be contained.
  • organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
  • the absorber of light having a specific wavelength a known absorber can be used.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
  • the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
  • the color filter may have a structure in which each pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
  • the pixel forming method is a step of applying the magenta color photosensitive resin composition of the present invention described above on a support to form a photosensitive resin composition layer, and a photolithography method for the photosensitive resin composition layer. It can be manufactured through the process of forming a pattern.
  • the pattern formation by the photolithography method consists of a step of applying the magenta-color photosensitive resin composition of the present invention described above on a support to form a photosensitive resin composition layer and a pattern of the photosensitive resin composition layer. It is preferable to include a step of exposing and a step of developing and removing an unexposed portion of the photosensitive resin composition layer after exposure.
  • each step will be described.
  • the magenta-colored photosensitive resin composition layer is applied onto the support to form the photosensitive resin composition layer.
  • the support is not particularly limited and may be appropriately selected depending on the intended use. Examples thereof include a glass substrate and a silicon substrate, and a silicon substrate is preferable. Further, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate. Further, a black matrix that separates each pixel may be formed on the silicon substrate. Further, the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
  • the surface contact angle of the base layer is preferably 20 to 70 ° when measured with diiodomethane. Further, it is preferably 30 to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the wettability of the magenta photosensitive resin composition layer is good.
  • the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
  • a known method can be used as a method for applying the magenta color photosensitive resin composition.
  • a drop method drop cast
  • a slit coat method for example, a spray method; a roll coat method; a spin coat method; a cast coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
  • Method Various printing methods such as inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method; Transfer method using a mold or the like; nanoimprint method or the like can be mentioned.
  • the method of application in inkjet is not particularly limited, and is, for example, the method shown in "Expandable / usable inkjet-infinite possibilities seen in patents-, published in February 2005, Sumi Betechno Research" (especially from page 115). Page 133), JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, regarding the method of applying the magenta color photosensitive resin composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
  • the photosensitive resin composition layer formed on the support may be dried (prebaked).
  • prebaking may not be performed.
  • the prebake temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, still more preferably 110 ° C. or lower.
  • the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
  • the prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, still more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
  • the photosensitive resin composition layer is exposed in a pattern (exposure step).
  • the photosensitive resin composition layer can be exposed in a pattern by using a stepper exposure machine, a scanner exposure machine, or the like to expose the photosensitive resin composition layer through a mask having a predetermined mask pattern. As a result, the exposed portion can be cured.
  • Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm) and the like, and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
  • pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a cycle of a short time (for example, a millisecond level or less).
  • Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
  • the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment), or may be exposed in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
  • the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2). Can be done.
  • the oxygen concentration and the exposure illuminance may be appropriately combined with each other.
  • the oxygen concentration may be 10% by volume and the illuminance may be 10,000 W / m 2
  • the oxygen concentration may be 35% by volume and the illuminance may be 20000 W / m 2 .
  • the unexposed portion of the photosensitive resin composition layer after exposure is developed and removed (development step).
  • the unexposed portion of the photosensitive resin composition layer can be developed and removed using a developing solution.
  • the photosensitive resin composition layer in the unexposed portion is eluted in the developing solution, and only the photocured portion remains.
  • the temperature of the developer is preferably, for example, 20 to 30 ° C.
  • the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
  • Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
  • the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
  • the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
  • Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5.4.0] -7-undecene, etc.
  • examples thereof include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
  • the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
  • the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
  • the developer may further contain a surfactant. From the viewpoint of convenience of transfer and storage, the developer may be once produced as a concentrated solution and diluted to a concentration required for use.
  • the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, the rinsing is preferably performed by supplying the rinsing solution to the developed photosensitive resin composition layer while rotating the support on which the developed photosensitive resin composition layer is formed.
  • the nozzle for discharging the rinse liquid from the central portion of the support it is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support.
  • the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of the rinse can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion of the support to the peripheral portion.
  • Additional exposure processing and post-baking are post-development curing treatments to complete the curing.
  • the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
  • Post-baking is performed by continuously or batch-type the developed film (pixels) using a heating means such as a hot plate, a convection oven (hot air circulation type dryer), or a high-frequency heater so as to meet the above conditions. be able to.
  • the additional exposure process is performed, the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
  • the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
  • the configuration of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
  • a solid-state image pickup device CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
  • a transfer electrode made of polysilicon or the like.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
  • the partition wall preferably has a low refractive index for each colored pixel. Examples of the image pickup apparatus having such a structure include the apparatus described in Japanese Patent Application Laid-Open No. 2012-227478, Japanese Patent Application Laid-Open No. 2014-179757, and International Publication No. 2018/043654.
  • an ultraviolet absorbing layer may be provided in the structure of the solid-state image sensor to improve the light resistance.
  • the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
  • the image display device of the present invention has the above-mentioned film of the present invention.
  • the image display device include a liquid crystal display device and an organic electroluminescence display device.
  • the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
  • the liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
  • P-1 C.I. I. Pigment Red 122 (magenta color pigment)
  • P-2 C.I. I. Pigment Red 202 (magenta color pigment)
  • P-3 C.I. I. Pigment Red 209 (magenta color pigment)
  • P-4 C.I. I. Pigment Red 269 (magenta pigment)
  • the raw materials shown in the table below were mixed to produce the photosensitive resin compositions of Examples 1 to 46 and Comparative Examples 1 and 2.
  • the photosensitive resin compositions of Examples 1 to 46 are magenta-colored photosensitive resin compositions.
  • the total content of the magenta color pigment and the magenta color dye in the total solid content of the photosensitive resin composition is described. Further, in the column of the content of the magenta color dye, the content of the magenta color dye in the coloring material is described.
  • Dye-1 Xanthene dye having the following structure (magenta dye, weight average molecular weight 10000)
  • Dye-2 Dipyrromethene dye with the following structure (magenta dye, weight average molecular weight 7000)
  • Dye-3 Triarylmethane dye (magenta dye) with the following structure
  • Dye-4 Xanthene dye (magenta dye) with the following structure
  • Dye-5 Xanthene dye (magenta dye) with the following structure
  • Dye-6 Xanthene dye (magenta dye) with the following structure
  • Dye-7 Xanthene dye (magenta dye) with the following structure
  • Dye-8 Xanthene dye (magenta dye) with the following structure
  • Dye-9 Xanthene dye (magenta dye) with the following structure
  • A-1 Epoxy compound (EHPE3150, manufactured by Daicel Corporation, 1,2-epoxy-4- (2-oxylanyl) cyclohexane adduct of 2,2'-bis (hydroxymethyl) -1-butanol)
  • A-2 UV absorber (UV-503, manufactured by Daito Kagaku Co., Ltd.)
  • Su-1 A compound having the following structure (weight average molecular weight: 14000, the numerical value indicating the ratio of repeating units is mol%)
  • Su-2 KF-6001 (Silicone-based surfactant, manufactured by Shin-Etsu Chemical Co., Ltd.)
  • a silicon wafer having a diameter of 8 inches (20.32 cm) was heat-treated in an oven at 200 ° C. for 30 minutes.
  • a resist solution for undercoating (CT-4000, manufactured by FUJIFILM Electronics Materials Co., Ltd.) was applied onto this silicon wafer so that the dry film thickness was 0.1 ⁇ m, and further in an oven at 220 ° C. 1
  • the undercoat layer was formed by heating and drying for an hour to obtain a silicon wafer substrate with an undercoat layer.
  • the photosensitive resin composition was applied onto the undercoat layer of the silicon wafer substrate with the undercoat layer prepared above.
  • a heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. to form a coating film (photosensitive resin composition layer).
  • the coating film was irradiated with light having a wavelength of 365 nm using an i-line stepper exposure device FPA-3000i5 + (manufactured by Canon Inc.) at an exposure amount of 500 mJ / cm 2 through a mask having a pattern. Exposed.
  • a mask having an island pattern of 1.4 ⁇ m ⁇ 1.4 ⁇ m was used.
  • the substrate on which the coated film after exposure was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and an alkaline developer CD-2060 (Fuji) was placed.
  • a colored pattern (colored pixel) was formed by paddle developing at room temperature for 60 seconds using a film electronics materials company.
  • the substrate on which the colored pixels are formed is fixed on a horizontal rotary table by a vacuum chuck method, and while the substrate is rotated at a rotation speed of 50 rpm by a rotating device, pure water is showered from above the center of rotation from the nozzle. It was supplied in a form and rinsed (23 seconds x 2 times). Then, spin-drying was performed, and then post-baking was performed on a hot plate at 200 ° C. for 300 seconds to obtain a substrate on which colored pixels were formed (hereinafter referred to as a colored pixel substrate).
  • the obtained colored pixel substrate was cut, and the cross section of the colored pixel was observed at a magnification of 20000 times using a scanning electron microscope (SEM), and evaluated according to the following criteria.
  • the photosensitive resin composition was applied onto the undercoat layer of the silicon wafer substrate with the undercoat layer prepared above. Then, a heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. to form a coating film. Then, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), the entire surface of the coating film was exposed to light having a wavelength of 365 nm at an exposure amount of 500 mJ / cm 2.
  • the substrate on which the coated film after exposure was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and an alkaline developer CD-2060 (Fuji) was placed. Paddle development was performed at room temperature for 60 seconds using Film Electronics Materials Co., Ltd.
  • the developed substrate is fixed on a horizontal rotary table by a vacuum chuck method, and while the substrate is rotated at a rotation speed of 50 rpm by a rotating device, pure water is supplied from above the center of rotation in a shower shape from above the center of rotation. Rinse treatment (23 seconds x 2 times) was performed. It was then spin dried and then post-baked on a hot plate at 200 ° C.
  • the surface of the obtained film was observed with an atomic force microscope (AFM), and the surface roughness (Ra) of the film was calculated.
  • the photosensitive resin compositions of Examples 1 to 46 had good evaluations of development residue, resolution and surface roughness.
  • the maximum value of the absorbance for light in the wavelength range of 400 to 450 nm is 0.5 or less and 600 when the absorbance for light having a wavelength of 540 nm is 1.
  • the maximum value of the absorbance for light in the wavelength range of about 700 nm was 0.5 or less.
  • the wavelength of light having an absorbance of 0.3 is in the wavelength range of 450 to 500 nm and 550 to 600 nm. It was present in each of the wavelength ranges.
  • the maximum value of the light transmittance in the wavelength range of 400 to 500 nm in the thickness direction of the film is 70. % Or more, the minimum value of the light transmittance in the wavelength range of 450 to 600 nm was 30% or less, and the maximum value of the light transmittance in the wavelength range of 550 to 700 nm was 70% or more. Further, the wavelengths showing 50% of the light transmittance in the thickness direction of the film existed in each of the wavelength range of 450 to 500 nm and the wavelength range of 550 to 600 nm.
  • a wavelength range of 400 to 500 nm in the thickness direction of the film was formed.
  • the maximum value of the light transmittance is 80% or more
  • the minimum value of the light transmittance in the wavelength range of 450 to 600 nm is 10% or less
  • the maximum value of the light transmittance in the wavelength range of 550 to 700 nm is 90. It was more than%.
  • wavelengths showing a light transmittance of 50% in the thickness direction of the film existed in each of the wavelength range of 475 to 495 nm and the wavelength range of 570 to 590 nm.
  • Example 1001 A silicon wafer having a diameter of 8 inches (20.32 cm) was heat-treated in an oven at 200 ° C. for 30 minutes. Next, a resist solution for undercoating (CT-4000, manufactured by FUJIFILM Electronics Materials Co., Ltd.) was applied onto this silicon wafer so that the dry film thickness was 0.1 ⁇ m, and further in an oven at 220 ° C. 1 The undercoat layer was formed by heating and drying for an hour to obtain a silicon wafer substrate with an undercoat layer. The photosensitive resin compositions of Examples 1 to 21 were applied onto the undercoat layer of the silicon wafer substrate with the undercoat layer prepared above.
  • CT-4000 manufactured by FUJIFILM Electronics Materials Co., Ltd.
  • a heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. to form a coating film (photosensitive resin composition layer).
  • the coating film was irradiated with light having a wavelength of 365 nm using an i-line stepper exposure device FPA-3000i5 + (manufactured by Canon Inc.) at an exposure amount of 500 mJ / cm 2 through a mask having a pattern. Exposed.
  • a mask having an island pattern of 1.4 ⁇ m ⁇ 1.4 ⁇ m was used.
  • the substrate on which the coated film after exposure was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and an alkaline developer CD-2060 (Fuji) was placed.
  • a colored pattern (colored pixel) was formed by paddle developing at room temperature for 60 seconds using a film electronics materials company.
  • the substrate on which the colored pixels are formed is fixed on a horizontal rotary table by a vacuum chuck method, and while the substrate is rotated at a rotation speed of 50 rpm by a rotating device, pure water is showered from above the center of rotation from the nozzle. It was supplied in a form and rinsed (23 seconds x 2 times).
  • the transparent pixel forming composition 1 or the transparent pixel forming composition 2 is used to form transparent pixels in the missing portion of the colored pixels according to the same method as described above. Manufactured a color filter.
  • the transparent pixel forming composition 1 and the transparent pixel forming composition 2 those produced by the methods shown below were used.
  • compositions 1 and 2 for Forming Transparent Pixels The raw materials shown in the table below were mixed to produce compositions 1 and 2 for forming transparent pixels.
  • the solvent S-1, the resin D-1, the additive A-2, the surfactant Su-1, and the polymerization inhibitor In-1 are the above-mentioned raw materials, respectively. Details of raw materials other than these are as follows.
  • A-3 Compound with the following structure
  • A-4 ADEKA PLURONIC TR-702 (manufactured by ADEKA Corporation)
  • Examples 2001-2009> Manufacturing of yellow photosensitive resin composition and cyan photosensitive resin composition-
  • the raw materials shown in the table below were mixed to produce yellow photosensitive resin compositions 1 to 3 and cyan photosensitive resin compositions 1 to 4, respectively.
  • the maximum value of the transmittance is 90% or more, the minimum value of the light transmittance in the wavelength range of 415 to 445 nm is 10% or less, and the wavelength showing the light transmittance of 50% in the thickness direction of the film is 470 to.
  • the wavelength range of 490 nm it was present in the wavelength range of 490 nm.
  • the wavelength range of 450 to 550 nm in the thickness direction of the film was formed.
  • the maximum value of light transmission is 90% or more, the minimum value of light transmission in the wavelength range of 615 to 645 nm is 20% or less, and the wavelength indicating that the light transmission in the thickness direction of the film is 50%. It was present in each of the wavelength range of 395 to 415 nm and the wavelength range of 560 to 580 nm.
  • polymerizable compounds M-1, M-2, resin D-1, photopolymerization initiators I-1, I-5, additives A-1, A-2, and surfactants are the above-mentioned raw materials, respectively.
  • the activator Su-2, the polymerization inhibitor In-1 and the solvent S-1 are the above-mentioned raw materials, respectively.
  • the dispersion liquids 9 to 15 the dispersion liquids produced as follows were used.
  • D-1 Dispersant D-1 described above
  • D-2 Dispersant D-2 described above
  • the cyan-colored photosensitive resin composition shown in the table below was applied to the surface of the glass substrate. Then, a heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. to form a coating film (photosensitive resin composition layer). Next, the coating film is irradiated with light having a wavelength of 365 nm using an i-line stepper exposure device FPA-3000i5 + (manufactured by Canon Inc.) at an exposure amount of 500 mJ / cm 2 through a mask having a Bayer pattern. And exposed.
  • FPA-3000i5 + manufactured by Canon Inc.
  • the glass substrate on which the coated film after exposure was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and an alkaline developer CD-2060 ( Paddle development was performed at room temperature for 60 seconds using Fujifilm Electronics Materials Co., Ltd.
  • the glass substrate is fixed on a horizontal rotary table by a vacuum chuck method, and while the glass substrate is rotated at a rotation speed of 50 rpm by a rotating device, pure water is supplied from above the center of rotation in a shower shape from the ejection nozzle to rinse.
  • the treatment 23 seconds x 2 times) was performed. It was then spin dried and then post-baked on a hot plate at 200 ° C.
  • cyan pixels were formed in the openings of the cyan pixels on the glass substrate by the same procedure as above except that the photomask of the island pattern was used.
  • magenta photosensitive resin composition described in the table below, the magenta color was applied to the openings of the cyan and yellow pixels on the glass substrate in the same procedure as above except that the island pattern photomask was used. Pixels were formed. In this way, a color filter in which cyan pixels, yellow pixels and magenta pixels were formed was manufactured.
  • NTSC American National Television System Committee
  • NSPW300BS pseudo-white LED light source
  • Red defined by the three primary colors of the standard method, red (0.67, 0.33), green (0.21, 0.71), and blue (0.14, 0.08) to the area surrounded by blue).
  • the color reproducibility was evaluated by measuring the ratio of the area of the triangle to the area of the reference value, assuming that the area of the triangles of the three colors (R) green (G) and blue (B) was 100. The evaluation results are shown below.
  • A The ratio of the area of the triangle to the area of the standard value is 80% or more
  • B The ratio of the area of the triangle to the area of the standard value is 70% or more and less than 80%
  • C The area of the triangle to the area of the standard value The ratio is 60% or more and less than 70%
  • D The ratio of the area of the triangle to the area of the reference value is less than 60%.
  • the color filters of Examples 2001 to 2009 were excellent in color reproducibility.
  • Examples 3001 to 3009> A method similar to the method described in paragraph No. 0273 is used on the glass substrate on which the color filters of Examples 2001 to 2009 are formed, using the composition for forming red pixels, the composition for forming green pixels, and the composition for forming blue pixels.
  • a color filter was manufactured by forming red pixels, green pixels, and blue pixels in the missing portions of the colored pixels.
  • the composition for forming a red pixel, the composition for forming a green pixel, and the composition for forming a blue pixel those produced by the methods shown below were used.
  • dispersion liquid R-1, dispersion liquid G-1, and dispersion liquid B-1 The mixed solution containing the raw materials shown in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.1 mm diameter). Next, a dispersion treatment was performed using a high-pressure disperser NANO-3000-10 with a decompression mechanism (manufactured by Nippon BEE Co., Ltd.) under the conditions of a pressure of 2000 kg / cm 2 and a flow rate of 500 g / min. This dispersion treatment was repeated 10 times in total to obtain a dispersion liquid.
  • a high-pressure disperser NANO-3000-10 with a decompression mechanism manufactured by Nippon BEE Co., Ltd.
  • composition for forming red pixels >> 67.14 parts by mass of dispersion R-1, 1.142 parts by mass of polymerizable compound M-4, 1.0119 parts by mass of resin D-6, and 0.603 parts of photopolymerization initiator I-1. Parts by mass, 0.0417 parts by mass of the surfactant Su-2, 0.0006 parts by mass of the polymerization inhibitor In-1, 27.736 parts by mass of the solvent S-1, and 2 of the solvent S-2.
  • a composition for forming a red pixel was produced by mixing with 3248 parts by mass.
  • composition for forming green pixels 64.93 parts by mass of dispersion G-1, 1.809 parts by mass of polymerizable compound M-2, 0.7364 parts by mass of resin D-1, and 0.8 parts by mass of photopolymerization initiator I-1. Parts by mass, 0.51 parts by mass of additive A-2, 0.0417 parts by mass of surfactant Su-2, 0.009 parts by mass of polymerization inhibitor In-1, and solvent S-1. 31.172 parts by mass was mixed to produce a composition for forming a green pixel.
  • composition for forming blue pixels >> 33.842 parts by mass of the dispersion B-1, 1.535 parts by mass of the dye Dye-1, 1.678 parts by mass of the polymerizable compound M-5, and 0.028 parts by mass of the resin D-1. , 0.112 parts by mass of resin D-3, 0.839 parts by mass of photopolymerization initiator I-6, 0.707 parts by mass of additive A-1, and 0. 0063 parts by mass, 0.0008 parts by mass of the polymerization inhibitor In-1, 0.922 parts by mass of the solvent S-1, and 60.33 parts by mass of the solvent S-2 are mixed for forming a blue pixel. The composition was produced.
  • composition for forming a red pixel The details of each material used for producing the composition for forming a red pixel, the composition for forming a green pixel, and the composition for forming a blue pixel are as follows.
  • Dispersion R-1, Dispersion G-1, Dispersion B-1 Dispersion R-1, Dispersion G-1, Dispersion B-1 described above -Dye Dye-1: The above-mentioned dye Dye-1 Polymerizable compound M-2: NK ester A-TMMT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.) -Polymerizable compound M-4: KAYARAD DPCA (manufactured by Nippon Kayaku Co., Ltd.) -Polymerizable compound M-5: Ethylene oxide modified product of trimethyl propanetriacrylate-Resin D-1: The same resin as the above-mentioned dispersant D-1-Resin D-3: The same resin as the above-mentioned resin D-3-Resin D-6: Resin having the following structure (the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
  • Photopolymerization Initiator I-1 The above-mentioned photopolymerization initiator I-1 -Photopolymerization initiator I-6: A compound having the following structure -Additive A-1: Additive A-1 described above -Additive A-2: Additive A-2 described above -Surfactant Su-2: The above-mentioned surfactant Su-2 -Polymerization inhibitor In-1: p-methoxyphenol-Solvent S-1: Propylene glycol monomethyl ether acetate-Solvent S-2: Cyclohexanone

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Abstract

Composition de résine photosensible magenta comprenant un matériau de couleur, une résine, un composé polymérisable et un solvant. Le matériau de couleur contient un pigment magenta et un colorant magenta, la teneur en colorant magenta dans le matériau de couleur étant d'au moins 20 % en masse, la teneur totale en pigment magenta et en colorant magenta dans les solides totaux de la composition de résine photosensible magenta étant d'au moins 30 % en masse. L'invention concerne également un film, un filtre coloré, un capteur d'image à semi-conducteurs et une unité d'affichage visuel qui utilisent la composition de résine photosensible magenta.
PCT/JP2021/017328 2020-05-12 2021-05-06 Composition de résine photosensible magenta, film, filtre coloré, capteur d'image à semi-conducteurs et unité d'affichage visuel WO2021230122A1 (fr)

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KR1020227037314A KR20220161397A (ko) 2020-05-12 2021-05-06 마젠타색 감광성 수지 조성물, 막, 컬러 필터, 고체 촬상 소자 및 화상 표시 장치

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11189733A (ja) * 1997-12-26 1999-07-13 Nippon Kayaku Co Ltd 色素組成物及びそれを用いる感光性着色樹脂組成物
JP2012208452A (ja) * 2010-04-21 2012-10-25 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用赤色着色組成物、およびカラーフィルタ
KR20150105837A (ko) * 2014-03-10 2015-09-18 동우 화인켐 주식회사 컬러필터용 착색감광성 수지 조성물, 컬러필터 및 이를 구비한 액정표시장치
JP2018168365A (ja) * 2017-03-29 2018-11-01 住友化学株式会社 着色硬化性樹脂組成物
KR20190106197A (ko) * 2018-03-08 2019-09-18 동우 화인켐 주식회사 적색 감광성 수지 조성물 및 이를 포함하는 컬러필터

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017201003A (ja) 2016-04-28 2017-11-09 Jsr株式会社 着色組成物、着色硬化膜、カラーフィルタ、表示素子及び固体撮像素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11189733A (ja) * 1997-12-26 1999-07-13 Nippon Kayaku Co Ltd 色素組成物及びそれを用いる感光性着色樹脂組成物
JP2012208452A (ja) * 2010-04-21 2012-10-25 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用赤色着色組成物、およびカラーフィルタ
KR20150105837A (ko) * 2014-03-10 2015-09-18 동우 화인켐 주식회사 컬러필터용 착색감광성 수지 조성물, 컬러필터 및 이를 구비한 액정표시장치
JP2018168365A (ja) * 2017-03-29 2018-11-01 住友化学株式会社 着色硬化性樹脂組成物
KR20190106197A (ko) * 2018-03-08 2019-09-18 동우 화인켐 주식회사 적색 감광성 수지 조성물 및 이를 포함하는 컬러필터

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