WO2016024497A1 - 着色組成物、着色硬化膜及び固体撮像素子 - Google Patents
着色組成物、着色硬化膜及び固体撮像素子 Download PDFInfo
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- WO2016024497A1 WO2016024497A1 PCT/JP2015/072086 JP2015072086W WO2016024497A1 WO 2016024497 A1 WO2016024497 A1 WO 2016024497A1 JP 2015072086 W JP2015072086 W JP 2015072086W WO 2016024497 A1 WO2016024497 A1 WO 2016024497A1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- GHJOIQFPDMIKHT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(O)CO GHJOIQFPDMIKHT-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
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- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- IWDANOJGJIFBEL-UHFFFAOYSA-N spiro[3.4]octane Chemical compound C1CCC21CCCC2 IWDANOJGJIFBEL-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 239000001043 yellow dye Substances 0.000 description 1
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Images
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- 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
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- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- 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
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- 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
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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Definitions
- the present invention relates to a colored composition, a colored cured film, and a solid-state imaging device, and more specifically, a colored composition used for forming a colored cured film used in a solid-state imaging device, and the colored composition.
- the present invention relates to a colored cured film and a solid-state imaging device including the colored cured film.
- a solid-state imaging device such as a CCD or CMOS generally disposes colors by disposing B (blue), G (green), and R (red) pixels on the light receiving element.
- B blue
- G green
- R red
- transmittance in a wavelength region of colors other than the color of the pixel is reduced and that color separation is excellent.
- red pixel there is a demand for a red pixel with reduced transmittance in the blue to green wavelength region.
- toning is performed using two or more types of pigments in order to obtain color characteristics required in each pixel.
- C.I. I. Pigment red 177, C.I. I. Pigment red 242, C.I. I. Pigment Red 254 or the like is used (see, for example, Patent Documents 1 to 3).
- JP 9-325209 A Japanese Patent Laid-Open No. 11-14824 JP 2000-89025 A
- C.I. I When Pigment Red 254 is used, it is difficult to produce a red pixel having good color reproducibility because the transition from the absorption region to the transmission region in the transmission curve is steep, and the transmittance in the wavelength region of 520 nm to 540 nm is difficult. Is slightly higher, which affects the transmission region of the green pixel.
- C.I. I When Pigment Red 177 is used, the rise from the absorption region to the transmission region in the transmission curve is C.I. I.
- an object of the present invention is to provide a coloring composition suitable for forming a red pixel having good color reproducibility and hardly affecting the transmission region of the green pixel. Furthermore, the subject of this invention is providing the solid-state image sensor which comprises the red pixel formed using the said coloring composition, and this red pixel.
- the present inventors have found that the above problem can be solved by using a red pigment having a specific structure and an isoindoline pigment as a colorant and further containing a specific solvent.
- the present invention is a colored composition containing (A) a colorant, (C) a binder resin, (D) a polymerizable compound, and (F) a solvent, (A) As a colorant, (A1) contains a pigment having a structure represented by the following formula (X) and (A2) an isoindoline pigment, and (F) as a solvent comprises (G) an alcohol, a ketone and an alkyl lactate ester.
- a coloring composition containing at least one selected from the group is provided.
- the present invention includes (A1) a pigment having a structure represented by the following formula (X) and (A2) an isoindoline pigment, and any of the following conditions (1) to (4) at a film thickness of 0.5 ⁇ m:
- a colored cured film satisfying one or more is provided.
- the transmittance at a wavelength of 400 nm is 30% or less.
- the maximum transmittance in the wavelength range of 430 to 560 nm is 15% or less.
- the transmittance at a wavelength of 580 nm is 50% or less.
- the transmittance at a wavelength of 620 nm is 80% or more.
- the present invention further provides a solid-state imaging device comprising the colored cured film.
- R a and R b each independently represent a monovalent organic group, p and q each independently represent an integer of 0 to 5.
- the coloring composition of the present invention By using the coloring composition of the present invention, it is possible to form a red pixel having good color reproducibility and hardly affecting the transmission region of the green pixel. Therefore, the colored composition of the present invention can be used very suitably for the production of a solid-state imaging device such as a CMOS image sensor.
- Coloring composition will be described in detail components of the colored composition of the present invention.
- the coloring composition of the present invention contains (A) a colorant, (A1) a pigment having a structure represented by the following formula (X) (hereinafter also referred to as “pigment X”) and (A2) an isoindoline pigment. It is essential to do.
- R a and R b each independently represent a monovalent organic group, p and q each independently represent an integer of 0 to 5.
- R a and R b examples include a hydrocarbon group and a group having a linking group containing an atom other than a carbon atom and a hydrogen atom between the C—C bonds of the hydrocarbon group. Can do. R a and R b may be the same or different.
- the hydrocarbon group include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.
- the “alicyclic hydrocarbon group” is a concept excluding an aliphatic hydrocarbon group having no cyclic structure.
- alicyclic hydrocarbon group and “aromatic hydrocarbon group” are not only a group consisting of only a ring structure, but also a divalent aliphatic hydrocarbon group substituted on the ring structure.
- the structure includes at least an alicyclic hydrocarbon or an aromatic hydrocarbon.
- the hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a hydroxyl group, an amino group, an alkoxyl group, and an aryloxy group.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the alkoxyl group may be either a straight chain or branched chain, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, and a tert-butoxy group.
- Examples of the aryloxy group include a phenoxy group and a benzyloxy group.
- the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or branched. Specific examples include an alkyl group, an alkenyl group, and an alkynyl group.
- the carbon number of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 24, and particularly preferably 1 to 20.
- the aliphatic hydrocarbon group include, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group; an ethenyl group, 1- Alkenyl groups such as propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 1,3-butadienyl group; ethynyl group, 1-propynyl group, 1-butynyl group, 1-pentynyl group, 3-pentynyl And alkynyl groups such as groups.
- an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group,
- the alicyclic hydrocarbon group may be saturated or unsaturated, and includes, for example, a cycloalkyl group, a cycloalkenyl group, a condensed polycyclic hydrocarbon group, a bridged ring hydrocarbon group, a spiro hydrocarbon group, and a cyclic terpene hydrocarbon group. Can be mentioned.
- the carbon number of the alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 12, and still more preferably 6 to 12.
- alicyclic hydrocarbon group examples include, for example, a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a t-butylcyclohexyl group; a cycloalkenyl group such as a 1-cyclohexenyl group; Condensed polycyclic hydrocarbon groups such as cyclodecanyl group, decahydro-2-naphthyl group and adamantyl group; tricyclo [5.2.1.0 2,6 ] decan-8-yl group, pentacyclopentadecanyl group, Bridged ring hydrocarbon groups such as isobonyl group, dicyclopentenyl group, tricyclopentenyl group; monovalent group obtained by removing one hydrogen atom from spiro [3,4] heptane, spiro [3,4] octan
- Spirohydrocarbon groups cyclic terpene hydrocarbon groups such as monovalent groups in which one hydrogen atom is removed from p-menthane, tujang, caran, etc. wear.
- aromatic hydrocarbon group include an aryl group.
- the “aryl group” means a monocyclic to tricyclic aromatic hydrocarbon group, and the carbon number is preferably 6 to 20, and more preferably 6 to 14.
- aromatic hydrocarbon group examples include, for example, phenyl group, benzyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, naphthyl group, anthryl group, phenanthryl group, azulenyl group, 9 -A fluorenyl group etc. can be mentioned.
- linking group In the group having a linking group containing a carbon atom and an atom other than a hydrogen atom between the C—C bonds of the hydrocarbon group, examples of the linking group include —O—, —S—, —SO 2 —, —CO—. , -COO-, -OCO-, -CONR- (R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), and -NR- (R is as defined above).
- One or more linking groups can be present. Note that the bonding position of the linking group is arbitrary.
- the linking group may have a terminal or a C—C bond, and the hydrocarbon group and the linking group may form a ring structure. May be.
- R a and R b a hydrocarbon group is preferable, an aromatic hydrocarbon group is more preferable, and a phenyl group is still more preferable.
- p and q each independently represent an integer of 0 to 5, preferably 1 or 2, and more preferably 1.
- pigment X for example, a compound classified as a pigment in a color index (CI; issued by The Society of Dyers and Colorists), that is, a color index (CI) number is attached.
- CI color index
- C.I. I. Pigment Red 264 can be mentioned as a suitable pigment.
- C.I. I. Pigment yellow 139 As isoindoline pigments, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 185.
- an isoindoline pigment together as a colorant, the transmittance in the wavelength region of 400 to 560 nm can be reduced, so that a red pixel with reduced transmittance in the blue to green wavelength region can be formed.
- C.I. I. Pigment Yellow 185 is preferable.
- the content ratio of (A1) pigment X and (A2) isoindoline pigment can be set as appropriate, a red pixel having excellent color reproducibility and high transmittance and hardly affecting the green transmission region.
- the mass ratio [(A1) / (A2)] between the component (A1) and the component (A2) is preferably 85/15 to 65/35.
- the mass ratio [(A1) / (A2)] is preferably 80/20 to 65/35, more preferably 75/25 to 65/35. 70/30 to 65/35 is more preferable.
- the mass ratio [(A1) / (A2)] is preferably 85/15 to 70/30, more preferably 85/15 to 75/25. 85/15 to 80/20 is particularly preferable.
- the mass ratio [(A1) / (A2)] is preferably 85/15 to 70/30 from the viewpoint of forming a red pixel in which the transmittance in the blue to green wavelength region is reduced in a balanced manner. / 20 to 70/30 is more preferable.
- the coloring composition of the present invention may contain a colorant other than (A1) Pigment X and (A2) Isoindoline pigment to the extent that the effects of the present invention are not affected.
- a colorant other than (A1) Pigment X and (A2) Isoindoline pigment to the extent that the effects of the present invention are not affected.
- Specific examples include pigments and dyes that are classified as pigments in the color index (CI; issued by The Society of Dyers and Colorists).
- pigments examples include those with the following color index (CI) numbers.
- Pigment red 52 1, C.I. I. Pigment red 52: 2, C.I. I. Pigment red 53: 1, C.I. I. Pigment red 54, C.I. I. Pigment red 57: 1, C.I. I. Pigment red 58, C.I. I. Pigment red 58: 1, C.I. I. Pigment red 58: 2, C.I. I. Pigment red 58: 3, C.I. I. Pigment red 58: 4, C.I. I. Pigment red 60: 1, C.I. I. Pigment red 63, C.I. I. Pigment red 63: 1, C.I. I. Pigment red 63: 2, C.I. I. Pigment red 63: 3, C.I. I.
- Pigment red 243 C.I. I. Pigment red 247, C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 262, C.I. I. Pigment Red 272, etc. I. Red pigments other than CI Pigment Red 264;
- Pigment yellow 129 C.I. I. Pigment yellow 133, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 153, C.I. I. Pigment yellow 154, C.I. I. Pigment yellow 155, C.I. I. Pigment yellow 166, C.I. I. Pigment yellow 168, C.I. I. Pigment yellow 169, C.I. I. Pigment yellow 180, C.I. I. Pigment yellow 183, C.I. I. Pigment yellow 191, C.I. I. Pigment yellow 191: 1, C.I. I. Pigment yellow 206, C.I. I. Pigment yellow 209, C.I. I. Pigment yellow 209: 1, C.I. I. Pigment yellow 211, C.I. I. Pigment yellow 212, C.I. I. Yellow pigments other than isoindoline pigments such as CI Pigment Yellow 215.
- red dyes include xanthene compounds, triarylmethane compounds, cyanine compounds, anthraquinone compounds, and dipyrromethene compounds.
- yellow dyes include anthraquinone compounds, azo compounds, azomethine compounds, and quinophthalone compounds.
- dye Diode
- CI The Society of Dyer's and Colorists company
- the content ratio of the other colorant is preferably 30% by mass or less, more preferably 10% by mass or less, and still more preferably 5% by mass or less with respect to the total content of (A) the colorant.
- (A1) Pigment X, (A2) Isoindoline pigment, and other pigments that are optionally mixed are subjected to a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof. It can also be used after purification. Further, these pigments may be used by modifying the particle surface with a resin, if desired. Examples of the resin that modifies the pigment particle surface include a vehicle resin described in JP-A No. 2001-108817, or various commercially available resins for dispersing pigments. The organic pigment may be used after the primary particles are refined by so-called salt milling. As a salt milling method, for example, a method disclosed in Japanese Patent Application Laid-Open No. 08-179111 can be employed.
- the colorant in addition to (A) pigment X and (A2) isoindoline pigment, (A) the colorant may contain other pigments that are arbitrarily mixed, but the average particle size of the pigment contained in the colorant The diameter is preferably 15 to 100 nm, more preferably 20 to 80 nm, and still more preferably 20 to 55 nm. According to such an embodiment, a colored cured film having sufficient surface smoothness can be formed.
- the “average particle diameter of the pigment” is a value obtained by measuring the long diameter of 100 primary particles existing in the observation field of the transmission electron microscope and calculating the average value thereof.
- a known dispersion aid can be further contained together with (A1) pigment X, (A2) isoindoline pigment and other colorant optionally mixed.
- the dispersion aid include pigment derivatives.
- a pigment derivative having an acidic functional group is preferable from the viewpoint of obtaining a colored composition having excellent developability.
- the acidic functional group include a sulfo group, a carboxyl group, and a phosphoric acid group. A sulfo group and a carboxyl group are more preferable, and a sulfo group is still more preferable.
- Specific examples include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.
- the content of the dispersion aid is superior to the total content of the colorant (A) because it has excellent color reproducibility and high transmittance, and forms a red pixel that hardly affects the transmission region of other colors.
- 0.1 to 10% by mass is preferable, 0.2 to 5% by mass is more preferable, and 0.5 to 3% by mass is still more preferable.
- the content ratio of the colorant has excellent color reproducibility and high transmittance, and from the point of forming a red pixel that does not easily affect the transmission region of other colors, in the solid content of the coloring composition, Usually 5 to 70% by mass, preferably 30 to 60% by mass, more preferably 40 to 55% by mass, and particularly preferably 45 to 55% by mass.
- solid content is components other than the solvent mentioned later.
- a dispersing agent can be further contained together with (A1) pigment X, (A2) isoindoline pigment and other colorant optionally used.
- the dispersant include a urethane-based dispersant, a polyethyleneimine-based dispersant, a polyoxyalkylene alkyl ether-based dispersant, a polyoxyalkylene alkylphenyl ether-based dispersant, and a dispersion containing a repeating unit having an alkylene oxide structure.
- poly (alkylene glycol) diester dispersants poly (alkylene glycol) diester dispersants, sorbitan fatty acid ester dispersants, polyester dispersants, (meth) acrylic dispersants, and the like.
- acrylic dispersants such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN22102 (above, manufactured by BYK Corporation (BYK)), Disperbyk-161, Urethane dispersants such as Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above, manufactured by BYK Chemy (BYK)), Solsperse 76500 (manufactured by Lubrizol Co., Ltd.), Solsperse 24000 Polyethyleneimine dispersants such as Alusper PB821, Azisper PB822, Azisper PB880, Azisper PB88 (
- (B1) a dispersant containing (B1) a repeating unit having an alkylene oxide structure is preferable.
- (B1) As a dispersant containing a repeating unit having an alkylene oxide structure, an ethylenically unsaturated monomer represented by the following formula (1) (hereinafter also referred to as “unsaturated monomer (b1)”). And other copolymerizable ethylenically unsaturated monomers (hereinafter also referred to as “unsaturated monomer (b2)”) are more preferable.
- R 1 represents an alkanediyl group having 2 to 3 carbon atoms
- R 2 represents an alkyl group having 1 to 5 carbon atoms
- R 3 represents a hydrogen atom or a methyl group
- n represents an integer of 1 to 20. When n is 2 or more, a plurality of R 1 may be the same or different.
- R 1 examples include an ethylene group, a 1,2-propanediyl group, and a 1,3-propanediyl group. Of these, an ethylene group and a 1,2-propanediyl group are preferable.
- the alkyl group for R 2 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Of these, a methyl group, an ethyl group, a propyl group, and a butyl group are preferable.
- n is preferably 1 to 10, and more preferably 1 to 5.
- Examples of the unsaturated monomer (b2) include those similar to the unsaturated monomer (c1) and unsaturated monomer (c2) described below. Among them, the unsaturated monomer (b1) It is preferable that (meth) acrylic acid ester other than is included.
- the content ratio of the repeating unit having an alkylene oxide structure is 3 to 40% by mass in all the repeating units. From the standpoint of forming, it is preferably 5 to 35% by mass, more preferably 7 to 30% by mass, particularly preferably 10 to 27% by mass, and most preferably 13 to 27% by mass.
- a dispersant containing a repeating unit having an alkylene oxide structure has a polystyrene-reduced weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran). Usually, it is 1,000 to 50,000, preferably 5,000 to 30,000.
- the dispersant (B) can be used alone or in admixture of two or more.
- the dispersant preferably has an amine value of 10 to 200 mgKOH / g, more preferably 50 to 180 mgKOH / g, and further preferably 80 to 150 mgKOH / g.
- the “amine value” in the present invention represents the number of mg of KOH equivalent to the acid required to neutralize 1 g of the solid content of the dispersant.
- the content of the (B) dispersant is preferably 5 to 300 parts by weight, more preferably 10 to 200 parts by weight, and further 20 to 100 parts by weight with respect to 100 parts by weight of the (A) colorant. 20 to 50 parts by mass is preferable.
- the content ratio of the dispersing agent containing a repeating unit having (B1) an alkylene oxide structure is 50 with respect to the total content of (B) the dispersing agent. % By mass or more is preferable, and 80% by mass or more is more preferable.
- the (C) binder resin in the present invention is not particularly limited, but is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group.
- a polymer having a carboxyl group (hereinafter also referred to as “carboxyl group-containing polymer”) is preferable.
- an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “unsaturated monomer”).
- a copolymer of another copolymerizable ethylenically unsaturated monomer hereinafter also referred to as “unsaturated monomer (c2)”).
- unsaturated monomer (c1) examples include (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meta ) Acrylate, p-vinylbenzoic acid and the like. These unsaturated monomers (c1) can be used alone or in admixture of two or more.
- unsaturated monomer (c2) for example, N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide; aromatics such as styrene, ⁇ -methylstyrene, p-hydroxystyrene, p-hydroxy- ⁇ -methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene Vinyl compounds;
- N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide
- aromatics such as styrene, ⁇ -methylstyrene, p-hydroxystyrene, p-hydroxy- ⁇ -methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene Vinyl compounds
- Vinyl ethers such as cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) -3-ethyloxetane
- a macromonomer having a mono (meth) acryloyl group at the end of the polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane.
- These unsaturated monomers (c2) can be used alone or in admixture of two or more.
- the copolymerization ratio of the unsaturated monomer (c1) in the copolymer is preferably 5 to 50% by mass. More preferably, it is 10 to 40% by mass.
- copolymer of the unsaturated monomer (c1) and the unsaturated monomer (c2) include, for example, JP-A-7-140654, JP-A-8-259876, and JP-A-10-31308. No. 10, JP-A-10-300902, JP-A-11-174224, JP-A-11-258415, JP-A-2000-56118, JP-A-2004-101728, etc. Coalescence can be mentioned.
- a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain as the (C) binder resin from the viewpoint of the smoothness of the cured film.
- examples of such polymers include JP-A-5-19467, JP-A-6-230212, JP-A-7-207211, JP-A-9-325494, JP-A-11-140144, Those disclosed in JP 2008-181095 A can be exemplified.
- Examples of the carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain include the following polymers i) to iv). It can contain at least one selected from the group consisting of polymers.
- polybasic acid anhydride can also be made to
- Examples of the unsaturated isocyanate compound include those described in paragraph [0049] of JP-A No. 2010-044365.
- Examples of the polymerizable unsaturated compound having an oxiranyl group include those described in paragraph [0053] of JP 2010-044365 A.
- Examples of the polybasic acid anhydride include those described in paragraph [0067] of JP-A-2014-098140.
- the (C) binder resin has a polystyrene-reduced weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually from 1,000 to 100,000. 000, preferably 3,000 to 50,000.
- GPC gel permeation chromatography
- the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the (C) binder resin is preferably 1.0 to 5.0, more preferably 1. 0 to 3.0.
- Mn here says the number average molecular weight of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran).
- the (C) binder resin in the present invention can be produced by a known method. For example, it is disclosed in Japanese Patent Application Laid-Open No. 2003-222717, Japanese Patent Application Laid-Open No. 2006-259680, International Publication No. 2007/029871, etc.
- the structure, Mw, and Mw / Mn can also be controlled by the method used.
- the (C) binder resin can be used alone or in admixture of two or more.
- the content of (C) the binder resin is usually 10 to 1,000 parts by weight, preferably 15 to 500 parts by weight, more preferably 20 to 150 parts by weight with respect to 100 parts by weight of (A) the colorant. Part.
- the polymerizable compound (D) refers to a compound having two or more polymerizable groups.
- the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group.
- the polymerizable compound is preferably a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups.
- the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound and (meth) acrylic acid, a polyfunctional (meta) modified with caprolactone. ) Acrylate, alkylene oxide modified polyfunctional (meth) acrylate, polyfunctional urethane (meth) acrylate obtained by reacting hydroxyl-functional (meth) acrylate and polyfunctional isocyanate, hydroxyl-functional (meth) acrylate and acid anhydride
- the polyfunctional (meth) acrylate which has a carboxyl group obtained by making a product react can be mentioned.
- examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; and 3 such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Mention may be made of aliphatic polyhydroxy compounds having a valence higher than that.
- Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and glycerol diester. A methacrylate etc. can be mentioned.
- Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate.
- acid anhydrides examples include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid.
- acid anhydrides include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid.
- dianhydrides and tetrabasic acid dianhydrides such as benzophenone tetracarboxylic dianhydride.
- Examples of caprolactone-modified polyfunctional (meth) acrylates include compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955.
- the alkylene oxide-modified polyfunctional (meth) acrylate is at least one selected from bisphenol A di (meth) acrylate modified with at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene oxide.
- Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure.
- the melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as a basic skeleton, and is a concept including melamine, benzoguanamine or a condensate thereof.
- Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ′, N ′, N ′′, N ′′ -hexa (alkoxymethyl) melamine, N, N, N ′. , N′-tetra (alkoxymethyl) benzoguanamine, N, N, N ′, N′-tetra (alkoxymethyl) glycoluril, and the like.
- polyfunctional (meth) acrylate modified with alkylene oxide and polyfunctional (meth) acrylate having a carboxyl group are preferable from the viewpoint of forming a red pixel with little development residue, and modified with alkylene oxide.
- Polyfunctional (meth) acrylate is more preferable.
- the polyfunctional (meth) acrylates modified with alkylene oxide at least one selected from trimethylolpropane tri (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from ethylene oxide and propylene oxide.
- the polymerizable compound contains at least one selected from the group consisting of a polyfunctional (meth) acrylate modified with alkylene oxide and a polyfunctional (meth) acrylate having a carboxyl group
- the polyfunctional modified with alkylene oxide 40 mass% or more is preferable with respect to the whole quantity of (D) component, and the content rate of at least 1 sort (s) chosen from the group which consists of (meth) acrylate and the polyfunctional (meth) acrylate which has a carboxyl group is 50 mass% or more. More preferred is 70% by mass or more.
- the content of the polymerizable compound (D) in the present invention is preferably 10 to 1,000 parts by weight, more preferably 30 to 300 parts by weight, and 50 to 200 parts by weight with respect to 100 parts by weight of the (C) binder resin. Is more preferable, and 80 to 125 parts by mass is particularly preferable.
- the coloring composition of the present invention can contain (E) a photopolymerization initiator. Thereby, radiation sensitivity can be provided to a coloring composition.
- the photopolymerization initiator used in the present invention is a compound that generates an active species capable of initiating polymerization of the polymerizable compound by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray.
- photopolymerization initiators examples include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, ⁇ -diketone compounds, polynuclear quinone compounds, A diazo compound, an imide sulfonate compound, etc. can be mentioned.
- (E) photoinitiator can be used individually or in mixture of 2 or more types.
- the (E) photopolymerization initiator preferably contains at least one selected from the group of thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, and O-acyloxime compounds, and has a low surface roughness. From the viewpoint of forming a pixel, it is more preferable to contain at least one compound selected from the group consisting of (E1) O-acyloxime compounds and (E2) thioxanthone compounds and acetophenone compounds.
- (E1) O-acyloxime compounds include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl.
- E1 As commercially available O-acyloxime compounds, NCI-831, NCI-930 (manufactured by ADEKA Corporation), DFI-020, DFI-091 (manufactured by Daitokemix Corporation), etc. are used. You can also.
- 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazol-3-yl]-, 1- (O-acetyloxime), NCI-831 and NCI-930 are preferred, and 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime) is more preferable.
- thioxanthone compound examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4 -Dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and the like.
- acetophenone compounds include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2 -Dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, etc. Can be mentioned.
- the content ratio of the component (E1) and the component (E2) can be set as appropriate, but the surface roughness should be 20/80 to 80/20 as the mass ratio [(E1) / (E2)]. Is preferable from the viewpoint of forming a smaller pixel, more preferably 30/70 to 70/30.
- biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′- Bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 Examples include '5,5'-tetraphenyl-1,2'-biimidazole.
- hydrogen donor means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
- the hydrogen donor include mercaptan hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and the like. Mention may be made of amine hydrogen donors.
- hydrogen donors can be used alone or in admixture of two or more, but one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. Is preferable in that the sensitivity can be further improved.
- triazine compound examples include compounds described in paragraphs [0063] to [0065] of JP-B-57-6096 and JP-A-2003-238898.
- a sensitizer when a photopolymerization initiator other than a biimidazole compound such as an acetophenone compound is used, a sensitizer can be used in combination.
- a sensitizer include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, and 4-dimethyl.
- Ethyl aminobenzoate 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. Can be mentioned.
- the content of (E) the photopolymerization initiator is preferably 0.1 to 120 parts by weight, more preferably 1 to 100 parts by weight, with respect to 100 parts by weight of the (D) polymerizable compound. More preferred is 70 parts by weight.
- the coloring composition of this invention contains at least 1 sort (s) chosen from the group which consists of (G) alcohol, a ketone, and lactate alkylester as a (F) solvent. Thereby, the coloring composition excellent in film thickness uniformity and patterning property can be obtained.
- (G) component includes (F1) alcohol, ketone and alkyl lactate having a boiling point of less than 180 ° C. at 1 atm, and (F4) alcohol, ketone and alkyl lactate having a boiling point of at least 180 ° C. at 1 atm. Can be classified.
- the component (F1) has a boiling point at 1 atm of preferably 100 ° C. or higher and lower than 180 ° C., more preferably 110 ° C. or higher and 170 ° C. or lower.
- the component (F4) has a boiling point at 1 atm of preferably 180 ° C. or higher and 250 ° C. or lower, more preferably 180 ° C. or higher and 230 ° C. or lower, and 190 ° C. or higher and 220 ° C. or lower. More preferably, it is 200 degreeC or more and 220 degrees C or less especially.
- the component (F1) is not particularly limited as long as it is an alcohol, ketone or alkyl lactate having a boiling point of less than 180 ° C. at 1 atm.
- Ethylene glycol monomethyl ether (boiling point 124 ° C., the same shall apply hereinafter), ethylene glycol monoethyl ether (135 ° C.), ethylene glycol mono-n-propyl ether (150 ° C.), ethylene glycol mono-n-butyl ether (171 ° C.), propylene glycol (Poly) alkylene glycol monoalkyl such as monomethyl ether (120 ° C), propylene glycol monoethyl ether (133 ° C), propylene glycol mono-n-propyl ether (150 ° C), propylene glycol mono-n-butyl ether (170 ° C) ether; Methanol (65 ° C), ethanol (78 ° C), propanol (97 ° C), 1-but
- the component (F4) is not particularly limited as long as it is an alcohol, ketone, or alkyl lactate ester having a boiling point at 1 atm of 180 ° C. or higher.
- the component (G) is preferable, and alcohol is more preferable.
- alcohols ethylene glycol mono-n-butyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol monomethyl ether, propylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol Mono-n-propyl ether, diethylene glycol monoethyl ether, ethanol, 3-methoxybutanol and diacetone alcohol are preferred.
- the coloring composition of the present invention may contain a solvent other than the component (G).
- solvents include (F2) solvents other than alcohol, ketone, and alkyl lactate having a boiling point of 180 ° C. at 1 atm, and (F3) alcohols, ketones, and alkyl lactate having a boiling point of less than 180 ° C. at 1 atm. Mention may be made of solvents other than esters.
- the component (F2) has a boiling point at 1 atm of preferably 180 ° C. or higher and 250 ° C. or lower, more preferably 180 ° C. or higher and 230 ° C. or lower, further preferably 190 ° C. or higher and 220 ° C. or lower, and 200 ° C.
- the component (F3) has a boiling point at 1 atm of preferably 100 ° C. or higher and lower than 180 ° C., more preferably 130 ° C. or higher and 175 ° C. or lower, and further preferably 150 ° C. or higher and 175 ° C. or lower.
- the component (F2) is not particularly limited as long as it is a solvent other than alcohol, ketone, and alkyl lactate having a boiling point at 1 atm of 180 ° C. or more.
- dipropylene glycol methyl ether acetate (213 ° C.) propylene glycol Diacetate (190 ° C), 1,3-butylene glycol diacetate (232 ° C), 1,6-hexanediol diacetate (260 ° C), ethylene glycol monobutyl ether acetate (192 ° C), diethylene glycol monoethyl ether (202 ° C) ), Esters such as diethylene glycol monoethyl ether acetate (217 ° C.), diethylene glycol monobutyl ether acetate (245 ° C.), triacetin (260 ° C.); cyclic esters such as ⁇ -butyrolactone (204 ° C.); And lactams such as N-methylpyrrolidone (202
- dipropylene glycol methyl ether acetate, propylene glycol diacetate, 1,3-butylene glycol diacetate, diethylene glycol monoethyl ether acetate, and ⁇ -butyrolactone are preferable, particularly dipropylene glycol methyl ether acetate, Diethylene glycol monoethyl ether acetate and ⁇ -butyrolactone are more preferred.
- the component (F3) is not particularly limited as long as it is a solvent other than alcohol, ketone and alkyl lactate having a boiling point of less than 180 ° C. at 1 atm.
- the component (F3) contains at least one selected from the group consisting of propylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, and ethyl 3-ethoxypropionate from the viewpoints of solubility and pigment dispersibility. It is particularly preferable to do this.
- the content of the solvent is not particularly limited, but is preferably such that the total concentration of each component excluding the solvent of the colored composition is 5 to 50% by mass, and 10 to 40% by mass. Is more preferred.
- the content of component (G) is preferably 3 to 40% by mass, more preferably 5 to 35% by mass, still more preferably 7 to 30% by mass, and particularly preferably 10 to 25% by mass in the total solvent.
- the content of the high-boiling solvent having a boiling point at 1 atm of 180 ° C. or more, that is, the content of the component (F2) and the component (F4) is preferably 1 to 40% by mass in the total solvent. % Is more preferable, 5 to 35% by mass is further preferable, and 10 to 30% by mass is particularly preferable.
- the content of the component (F3) is preferably 10 to 97% by mass, more preferably 20 to 90% by mass, still more preferably 30 to 80% by mass, and 40 to 70% by mass in the total solvent. Particularly preferred is 45 to 60% by mass.
- the coloring composition of this invention can also contain a various additive as needed.
- additives include fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); surfactants such as fluorosurfactants and silicon surfactants; vinyl Trimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxy Silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyl Dimeth
- the coloring composition of the present invention can be prepared by an appropriate method.
- the preparation method include (A1) a pigment X and (A2) an isoindoline pigment (A) a colorant, and (C) a binder.
- the resin and (D) polymerizable compound can be prepared by mixing together with the (F) solvent containing the (G) component and other components optionally added.
- the coloring composition for example, (A1) (A) a coloring agent containing pigment X, (B) a dispersing agent, (G) a solvent containing (F) solvent, and optional components (C) a first colorant dispersion containing a part of the binder resin, (A2) (A) a colorant containing an isoindoline pigment, (B) a dispersant, and (G) a component (F) solvent. And (C) a second colorant dispersion containing a part of the binder resin as an optional component, respectively, and then a first colorant dispersion, a second colorant dispersion, and (D) polymerization.
- A1 A) a coloring agent containing pigment X, (B) a dispersing agent, (G) a solvent containing (F) solvent, and optional components
- C) a first colorant dispersion containing a part of the binder resin for example, (A1) (A) a coloring agent containing pigment X, (B
- Preparation method (1) a colored composition
- (A1) pigment X and (A2) (A) a colorant containing an isoindoline pigment, (B) a dispersant, (G) a solvent (F) containing a component, and (C) one binder resin as an optional component. Part of the colorant dispersion, and the colorant dispersion and (D) the polymerizable compound, and (C) the binder resin, (E) the photopolymerization initiator, and additional (F) as necessary.
- a method of preparing a colored composition by adding and mixing a solvent and other components (hereinafter, also referred to as “preparation method (2)”) may be employed.
- the preparation method (2) is preferable from the viewpoint of obtaining a colored composition having excellent pigment dispersion stability.
- the preferred embodiment of the (G) component contained in the colorant dispersion is the same as the preferred embodiment of the (G) component described in the colored composition of the present invention.
- the colored cured film of the present invention includes (A1) pigment X and (A2) isoindoline pigment, and is any one of the following conditions (1) to (4) at a film thickness of 0.5 ⁇ m. It satisfies the above and can be formed using the colored composition of the present invention.
- the transmittance at a wavelength of 400 nm is 30% or less.
- the maximum transmittance in the wavelength range of 430 to 560 nm is 15% or less.
- the transmittance at a wavelength of 580 nm is 50% or less.
- the transmittance at a wavelength of 620 nm is 80% or more.
- the transmittance at a wavelength of 400 nm is more preferably 25% or less, and still more preferably 20% or less, from the viewpoint of efficiently blocking violet to blue light.
- the maximum transmittance in the wavelength region of 430 to 560 nm is more preferably 13% or less, further preferably 12% or less, and more preferably 10% or less from the viewpoint of efficiently blocking blue to green light. Particularly preferred.
- the transmittance at a wavelength of 580 nm is more preferably 40% or less, and still more preferably 30% or less, from the viewpoint of color reproducibility.
- fills conditions (4) it can be set as the red cured film excellent in photosensitivity.
- the transmittance at a wavelength of 620 nm is more preferably 83% or more, and still more preferably 85% or more, from the viewpoint of color reproducibility.
- the red cured film preferably satisfies any two or more of the conditions (1) to (4), depending on the required characteristics required, but preferably satisfies any three or more of the conditions (1) to (4). It is more preferable to satisfy this, and it is particularly preferable to satisfy all of the conditions (1) to (4).
- a colored cured film used for a color filter and a method for forming the same will be described.
- a method for forming the colored cured film constituting the color filter the following method is first exemplified.
- a light shielding layer black matrix
- pre-baking is performed to evaporate the solvent, thereby forming a coating film.
- post-baking is performed to form a pixel array in which red pixel patterns (colored cured films) are arranged in a predetermined arrangement.
- each radiation sensitive coloring composition of green or blue application of each radiation sensitive coloring composition, pre-baking, exposure, development, and post-baking are performed in the same manner as described above to obtain a green pixel array and blue color.
- a color filter in which pixel arrays of the three primary colors of red, green and blue are arranged on the substrate is obtained.
- the order of forming pixels of each color is not limited to the above.
- a black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithographic method. It can also be formed in the same manner as in the case of forming the above-mentioned pixel using a sexually colored composition.
- Examples of the substrate used when forming the colored cured film include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.
- these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.
- an appropriate coating method such as spraying, roll coating, spin coating (spin coating), slit die coating (slit coating), bar coating, etc.
- spin coating method spin coating method or a slit die coating method.
- Pre-baking is usually performed by a combination of vacuum drying and heat drying.
- the drying under reduced pressure is usually performed until reaching 50 to 200 Pa.
- the conditions for heat drying are usually about 70 to 110 ° C. and about 1 to 10 minutes.
- the coating thickness is usually 0.3 to 5 ⁇ m as the film thickness after drying.
- Examples of the radiation light source used when forming at least one selected from the pixel and the black matrix include, for example, a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, and a low pressure.
- Examples thereof include a lamp light source such as a mercury lamp, and a laser light source such as an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen laser.
- An ultraviolet LED can also be used as the exposure light source.
- the wavelength is preferably radiation in the range of 190 to 450 nm.
- the exposure dose of radiation is preferably 10 to 10,000 J / m 2 .
- the alkali developer include sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-.
- An aqueous solution of undecene, 1,5-diazabicyclo- [4.3.0] -5-nonene or the like is preferable.
- a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like
- a surfactant such as methanol or ethanol
- it is usually washed with water after alkali development.
- a development processing method a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
- the development conditions are preferably 5 to 300 seconds at room temperature.
- the post-baking conditions are usually 180 to 280 ° C. and about 3 to 60 minutes.
- the film thickness of the pixel thus formed is usually 0.5 to 5 ⁇ m, preferably 1.0 to 3 ⁇ m.
- a method for obtaining pixels of each color by an ink jet method disclosed in JP-A-7-318723, JP-A-2000-310706, etc. can be adopted.
- a partition having a light shielding function is formed on the surface of the substrate.
- a red liquid composition of the thermosetting coloring composition of the present invention is discharged into the formed partition wall by an inkjet apparatus, and then prebaked to evaporate the solvent.
- this coating film is exposed as necessary and then cured by post-baking to form a red pixel pattern.
- each green or blue thermosetting coloring composition using each green or blue thermosetting coloring composition, a green pixel pattern and a blue pixel pattern are sequentially formed on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns of the three primary colors of red, green and blue are arranged on the substrate is obtained.
- the order of forming pixels of each color is not limited to the above.
- the partition plays not only a light shielding function but also a function for preventing the color mixing of the thermosetting coloring compositions discharged in the respective sections, it is compared with the black matrix used in the first method described above.
- the film thickness is thick. Therefore, a partition is normally formed using a black radiation sensitive composition.
- the substrate used for forming the colored cured film, the light source of radiation, and the pre-baking and post-baking methods and conditions are the same as in the first method described above. In this way, the film thickness of the pixel formed by the ink jet method is approximately the same as the height of the partition wall.
- a protective film can also be formed on the pixel pattern obtained in this way, if necessary.
- the color filter including the colored cured film of the present invention formed in this way is suitable for forming a red pixel having good color reproducibility and hardly affecting the transmission region of the green pixel. It is extremely useful for solid-state imaging devices such as image sensors, color imaging tube devices, color sensors, and the like, and particularly useful as red pixels for color filters for solid-state imaging devices.
- the colored cured film of the present invention has good color reproducibility even when the film thickness is 0.4 to 0.8 ⁇ m, further 0.4 to 0.6 ⁇ m, particularly 0.45 to 0.55 ⁇ m, Further, it can be suitably used as a red pixel that hardly affects the transmission region of the green pixel.
- the solid-state image sensor of the present invention comprises the colored cured film of the present invention.
- red pixels formed using the colored composition of the present invention have good color reproducibility and are less likely to affect the transmission region of green pixels, and are therefore suitable for color filters of solid-state image sensors.
- the solid-state imaging device of the present invention can take an appropriate structure. For example, as one embodiment, by using the colored composition of the present invention to form a colored pixel (colored cured film) on a semiconductor substrate such as a CMOS substrate by the same operation as described above, in particular, spectral characteristics. In addition, a solid-state imaging device having excellent color separation can be manufactured.
- a red pixel, a blue pixel, and a green pixel are the following.
- the red pixel has (A1) pigment X and (A2) isoindoline pigment, and has a film thickness of 0. 0 from the viewpoint of making the red pixel having good color reproducibility and hardly affecting the transmission region of the green pixel. It is preferable to satisfy at least one of the above conditions (1) to (4) at 5 ⁇ m.
- the condition (5) is preferably 0.7 ⁇ m or less, more preferably 0.6 ⁇ m or less, still more preferably 0.55 ⁇ m or less, particularly preferably 0. .5 ⁇ m or less.
- the red pixel preferably satisfies any two or more of the conditions (1) to (4), depending on the required characteristics required, but satisfies any three or more of the conditions (1) to (4). It is more preferable that all of the conditions (1) to (4) are satisfied.
- the conditions (1) to (4) it is preferable that at least the condition (4) is satisfied, it is more preferable that at least the condition (2) and the condition (4) are satisfied, and at least the conditions (2), (3) and It is more preferable to satisfy (4), and it is particularly preferable to satisfy all of the conditions (1) to (4). It is preferable that these preferable embodiments relating to the conditions (1) to (4) and the embodiment relating to the condition (5) are simultaneously satisfied.
- the content ratio of (A1) Pigment X and (A2) Isoindoline pigment can be set as appropriate, a red pixel having excellent color reproducibility and high transmittance and hardly affecting the green transmission region is formed.
- the mass ratio [(A1) / (A2)] of (A1) pigment X and (A2) isoindoline pigment is preferably 85/15 to 65/35.
- the mass ratio [(A1) / (A2)] is preferably 80/20 to 65/35, more preferably 75/25 to 65/35, and 70 / 30 to 65/35 is more preferable.
- a red pixel that satisfies the condition (1) can be obtained.
- the mass ratio [(A1) / (A2)] is preferably 85/15 to 70/30, and 85/15 to 75 / 25 is more preferable, and 85/15 to 80/20 is particularly preferable.
- a red pixel that satisfies the condition (2) can be obtained.
- the mass ratio [(A1) / (A2)] is preferably 85/15 to 70/30, 80/20 to 70/30 is more preferable. By such an aspect, it can be set as the red pixel which satisfies the said conditions (1) and (2).
- the green pixel has a good color reproducibility even if it is a thin film, and from the viewpoint of making it a green pixel that hardly affects the transmission region of the blue pixel and the red pixel, C.I. I. Pigment green 36, C.I. I. Pigment green 58, C.I. I. Pigment Green 59 is preferably included, and C.I. I. Pigment green 58, C.I. I. More preferably, CI Pigment Green 59 is included.
- the green pixel may contain a colorant other than the green colorant, and particularly preferably contains a yellow colorant. As the yellow colorant, C.I.
- the content ratio of the colorant Is usually 5 to 70% by mass, preferably 15 to 60% by mass, more preferably 30 to 55% by mass, and particularly preferably 35 to 50% by mass in the solid content of the green coloring composition.
- the blue pixel has good color reproducibility even if it is a thin film, and from the viewpoint of forming a blue pixel that hardly affects the transmission region of the green pixel, C.I. I. Pigment blue 15: 6, C.I. I. Pigment violet 23 is preferably included.
- the content ratio of the colorant is blue.
- the solid content of the coloring composition is usually 5 to 70% by mass, preferably 15 to 60% by mass, more preferably 30 to 55% by mass, and particularly preferably 35 to 50% by mass.
- Synthesis example 1 A flask equipped with a condenser and a stirrer was charged with 100 parts by mass of propylene glycol monomethyl ether acetate and purged with nitrogen. Heat to 80 ° C., and at the same temperature, 100 parts by weight of propylene glycol monomethyl ether acetate, 25 parts by weight of benzyl methacrylate, 10 parts by weight of styrene, 20 parts by weight of N-phenylmaleimide, 5 parts by weight of glycerol monomethacrylate, 10 parts by weight of methacrylic acid A mixed solution of 30 parts by weight of ⁇ -carboxypolycaprolactone monoacrylate and 3 parts by weight of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour, and polymerization was carried out for 3 hours while maintaining this temperature.
- binder resin (C-1) solution This binder resin solution is referred to as “binder resin (C-1) solution”.
- Synthesis example 2 A flask equipped with a condenser and a stirrer was charged with 3 parts by mass of 2,2′-azobisisobutyronitrile and 100 parts by mass of propylene glycol monomethyl ether acetate, and subsequently 12 parts by mass of N-phenylmaleimide, 10 parts by mass of styrene, Methacrylic acid 20 parts by mass, 2-hydroxyethyl methacrylate 15 parts by mass, 2-ethylhexyl methacrylate 29 parts by mass, benzyl methacrylate 14 parts by mass and pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Industry Co., Ltd.) 5 A mass part was charged and the atmosphere was replaced with nitrogen.
- binder resin (C-2) solution This binder resin solution is referred to as “binder resin (C-2) solution”.
- Synthesis example 3 Place 370 parts by mass of propylene glycol monomethyl ether acetate in a reaction vessel, heat to 80 ° C. while injecting nitrogen gas into the vessel, and drop the mixture of the following monomers and thermal polymerization initiator at the same temperature over 1 hour to polymerize. Reaction was performed.
- binder resin (C-3) solution This binder resin solution is referred to as “binder resin (C-3) solution”.
- Synthesis example 4 An appropriate amount of nitrogen was flowed into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to form a nitrogen atmosphere, and 100 parts by mass of propylene glycol monomethyl ether acetate was added and heated to 85 ° C. with stirring. Next, using a dropping pump, 19 parts by mass of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate (a compound represented by the formula (I-1)) is added into the flask.
- binder resin (C-4) solution After cooling to room temperature, propylene glycol monomethyl ether acetate was added so that the solid content concentration was 40% by mass to obtain a binder resin solution (solid content concentration 40% by mass).
- This binder resin solution is referred to as “binder resin (C-4) solution”.
- Synthesis example 5 A flask equipped with a condenser and a stirrer was charged with 90 parts by mass of propylene glycol monomethyl ether acetate and purged with nitrogen, and then heated to 90 ° C.
- binder resin (C-5) solution This binder resin solution is referred to as “binder resin (C-5) solution”.
- Synthesis Example 6 A flask equipped with a condenser and a stirrer was charged with 370 parts by mass of propylene glycol monomethyl ether acetate, heated to 80 ° C., and the atmosphere in the flask was replaced with nitrogen.
- 18 parts by mass of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toa Gosei Co., Ltd.)
- 10 parts by mass of benzyl methacrylate 18.2 parts by mass of glycidyl methacrylate, 25 parts by mass of methyl methacrylate
- 2,2′-azo A mixture of 2.0 parts by mass of bisisobutyronitrile was added dropwise over 2 hours.
- binder resin (C-6) solution This binder resin solution is referred to as “binder resin (C-6) solution”.
- Synthesis example 7 560 parts by mass of propylene glycol monomethyl ether acetate is put in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomers and a thermal polymerization initiator is dropped at the same temperature over 1 hour for polymerization. Reaction was performed.
- the mixture was further reacted at 100 ° C. for 3 hours, then 1.0 part by mass of azobisisobutyronitrile dissolved in 55 parts by mass of propylene glycol monomethyl ether acetate was added, and further at 80 ° C. for 1 hour. The reaction was continued to obtain a copolymer solution. Next, the mixture of the following compound was dripped over 3 hours at 70 degreeC with respect to 338 mass parts of obtained copolymer solutions.
- binder resin (C-7) solution This binder resin solution is referred to as “binder resin (C-7) solution”.
- Synthesis example 8 67 parts by mass of propylene glycol monomethyl ether acetate and 33 parts by mass of propylene glycol monomethyl ether were placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas introduction tube. .
- 1 part by mass of perbutyl O was added to 100 parts by mass of the monomer mixture in a monomer mixture consisting of 11 parts by mass of tricyclodecanyl methacrylate, 31 parts by mass of benzyl methacrylate, and 23 parts by mass of methacrylic acid. This was dropped into the flask over 2 hours from the dropping funnel, and further stirred at 120 ° C.
- binder resin (C-8) solution This binder resin solution is referred to as “binder resin (C-8) solution”.
- Example 9 Referring to Example 1 of WO 2011/129078 pamphlet, A block having a repeating unit derived from dimethylaminoethyl methacrylate and butyl methacrylate, PME-200 (manufactured by NOF Corporation. Methoxypolyethylene glycol monomethacrylate.
- R 1 is an ethylene group
- This block copolymer is referred to as “dispersant (B-1)”.
- this resin solution was diluted with 33.3 parts by mass (containing 10 parts of polymer), methyl-3-methoxypropionate with 31.9 parts by mass, and propylene glycol monomethyl ether with 3.4 parts by mass.
- 0.3 parts by mass of trimellitic acid, 0.5 parts by mass of 3-glycidoxypropyltrimethoxysilane, and 0.005 parts by mass of the product name “FC-4432” (manufactured by Sumitomo 3M Limited) were dissolved. Then, a composition for forming a base film was prepared.
- C.I. I. Pigment Red 264 is 9.9 parts by mass and an average particle size of 42 nm is C.I. I. 1.1 parts by weight of CI Pigment Yellow 185, 0.4 parts by weight of dispersion aid ⁇ shown below, 8.45 parts by weight of dispersant (B-1) (solid content concentration 40% by weight) as a dispersant, binder A bead mill using 4.9 parts by mass of the resin (C-1) solution (solid content concentration 40% by mass), 60.25 parts by mass of propylene glycol monomethyl ether acetate and 15.0 parts by mass of propylene glycol monoethyl ether as solvents
- the pigment dispersion (R-1) was prepared by mixing and dispersing according to the above.
- the average particle diameter of the pigment is determined by measuring the long diameter of 100 primary particles of the pigment observed with a transmission electron microscope (“H-7650”, manufactured by Hitachi High-Technologies Corporation), and taking this average value as the
- each component is as follows.
- Y139 C.I. I. Pigment Yellow 139 Y150: C.I. I. Pigment Yellow 150
- Y138 C.I. I. Pigment Yellow 138
- the numerical value in parentheses after the pigment name indicates the average particle diameter of the pigment used.
- Example 1 21.8 parts by weight of the pigment dispersion (R-1), 0.55 parts by weight of the binder resin (C-2) solution (solid content concentration 40% by weight), and Kayrad DPEA-12 (Nippon Kayaku) as the polymerizable compound 0.65 parts by mass of ethylene oxide-modified dipentaerythritol hexaacrylate, manufactured by Co., Ltd., 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime) as a photopolymerization initiator ) (I manufactured by BASF, Irgacure OXE01) 0.18 parts by weight, 0.1 parts by weight of MegaFac F-554 (manufactured by DIC Corporation) as a fluorosurfactant, and 7.3 parts by weight of ⁇ -butyrolactone As a result, a colored composition (S-1) was obtained.
- R-1 pigment dispersion
- C-2 binder resin
- Viscosity immediately after preparation of the colored composition (S-1) was measured using an E-type viscometer (manufactured by Tokyo Keiki). Next, the colored composition (S-1) was filled in a light-shielding glass container, allowed to stand at 23 ° C. for 14 days in a sealed state, and then the viscosity was measured again using an E-type viscometer (manufactured by Tokyo Keiki). And the increase rate of the viscosity after 14-day storage with respect to the viscosity immediately after preparation was computed.
- the evaluation criteria are as follows, and the results are shown in Table 3.
- the composition for forming the base film is spin-coated. After coating, the substrate was baked at 250 ° C. for 2 minutes to form a base film having a thickness of 0.6 ⁇ m.
- the colored composition (S-1) was applied onto the undercoat film by spin coating, and then pre-baked at 100 ° C. for 120 seconds to form a coating film having a thickness of 0.50 ⁇ m.
- Film thickness measurement was performed with a reflection spectral film thickness meter (manufactured by Otsuka Electronics Co., Ltd., FE-3000) at the wafer center and at 1 cm intervals from the wafer center to the left and right (total of 15 locations including the wafer center).
- the difference ( ⁇ ft) between the maximum film thickness and the minimum film thickness in the wafer was calculated and evaluated according to the following criteria. The results are shown in Table 3.
- ⁇ Formation and evaluation of colored cured film Formation of colored cured film Using an automatic coating and developing apparatus (clean track manufactured by Tokyo Electron Ltd., trade name “MARK-Vz”) on a 6-inch silicon wafer, the composition for forming the underlying film was applied by spin coating. And then baked at 250 ° C. for 2 minutes to form a base film having a thickness of 0.6 ⁇ m.
- the colored composition (S-1) was applied onto the undercoat film by spin coating, and then pre-baked at 100 ° C. for 120 seconds to form a coating film having a thickness of 0.50 ⁇ m.
- the obtained substrate was cooled to room temperature, and the coating film on the substrate was subjected to pattern exposure by reduction projection exposure using an i-line stepper (NSR-2205i12D manufactured by Nikon Corporation) via a photomask.
- Pattern exposure was performed at a total of 105 locations in a pattern arranged in a matrix of 15 rows ⁇ 7 columns.
- the 15 rows of the matrix the minimum exposure amount is 50 mJ / cm 2, so that the maximum exposure is 750 mJ / cm 2, the condition of changing the amount of exposure for each line in the 50 mJ / cm 2 intervals It has become.
- the above seven columns are conditions in which the focal length is changed at intervals of 0.2 ⁇ m with the focal length optimum value (Focus 0.0 ⁇ m) as the center.
- the central row is the optimum focal length, and the focal length is changed for each row.
- the photomask a photomask in which a cured film was formed so that a 1.1 ⁇ m square pixel pattern was arranged within a range of 4 mm ⁇ 3 mm was used. The same operation was performed to produce two wafers having a cured film.
- the first wafer produced above was paddle developed for 30 seconds with a 0.3 mass% tetramethylammonium hydroxide aqueous solution in an automatic coating phenomenon apparatus, rinsed with ultrapure water, and spin-dried. Thereafter, post-baking was performed at 200 ° C. for 300 seconds on a hot plate to prepare a substrate (1) having a colored cured film pattern.
- the second wafer prepared above is paddle developed for 30 seconds with a 0.3 mass% tetramethylammonium hydroxide aqueous solution in an automatic coating phenomenon apparatus, rinsed with ultrapure water, and spin-coated. Dried.
- This wafer was subjected to paddle development for 30 seconds with an aqueous 0.3 mass% tetramethylammonium hydroxide solution in an automatic coating phenomenon apparatus, rinsed with ultrapure water, and spin-dried.
- This wafer was post-baked on a hot plate at 200 ° C. for 300 seconds to produce a substrate (2) having a colored cured film pattern.
- Evaluation Criteria A An exposure amount capable of forming a square pixel pattern of 1.1 ⁇ m square was in the range of 50 to 750 mJ / cm 2 , and the pattern cross-sectional shape formed at that time was rectangular.
- B The exposure dose capable of forming a square pixel pattern of 1.1 ⁇ m square is in the range of 50 to 750 mJ / cm 2 , but the pattern cross-sectional shape formed at that time was not rectangular.
- C The exposure dose capable of forming a square pixel pattern of 1.1 ⁇ m square was not in the range of 50 to 750 mJ / cm 2 , and none of the formed patterns had a rectangular cross-sectional shape.
- D The unexposed part was hardly dissolved and the pattern was not formed.
- the obtained substrate was cooled to room temperature, and reduced projection exposure (NSR-2005i10D manufactured by Nikon Corporation, exposure dose of 500 mJ / cm 2 at a wavelength of 365 nm) was applied to the coating film on the substrate through a photomask. Were exposed using.
- This substrate is developed in a paddle (liquid puddle) for 30 seconds with a 0.3% by mass tetramethylammonium hydroxide aqueous solution in an automatic coating phenomenon apparatus, rinsed with ultrapure water, spin-dried, and then on a hot plate.
- Post-baking was performed at 200 ° C. for 300 seconds to produce a silicon wafer having a square colored cured film with a side of 1 cm.
- the surface roughness of the upper portion of the colored cured film formed on the silicon wafer was measured using an atomic force microscope manufactured by Digital Instruments. The evaluation criteria are as follows, and the results are shown in Table 3.
- the colored composition (S-1) was applied on a glass substrate by a spin coating method and then heated at 100 ° C. for 180 seconds to form a coating film. Subsequently, the entire surface of the coating film on the substrate was exposed (exposure amount of 1,000 mJ / cm 2 at a wavelength of 365 nm). Next, the coating film was contacted with an aqueous solution containing 0.3% by mass of tetramethylammonium hydroxide for 15 seconds, and then the coating film was washed with water. Then, the glass wafer which has a colored cured film with a film thickness of 0.50 micrometer was obtained by heating for 300 second with a 200 degreeC hotplate.
- the transmittance (% T) of the glass wafer having the colored cured film was measured, and 400, 405, 410, 415, 420, 425, The transmittance at 430, 580 and 620 nm was determined. Further, the maximum transmittance in the wavelength region of 430 to 560 nm was obtained.
- Table 3 the transmittance in Table 3 is a value relative to the glass substrate, and the film thickness is a value measured with a stylus type step gauge (manufactured by Yamato Scientific Co., Ltd., Alpha Step IQ).
- the evaluation criteria for the transmittance at each wavelength are as follows, and if it is a colored cured film that satisfies all the following evaluation criteria, it has excellent color reproducibility and high transmittance and affects the transmission region of other colors. It can be said that it is a colored cured film that is difficult to give.
- the transmittance at 400 nm is 30% or less, the transmittance at 410 nm is 25% or less (more preferably 20% or less, more preferably 15% or less), and the transmittance at 420 nm is 20% or less (more) If the transmittance at 430 nm is 15% or less (more preferably 13% or less, more preferably 10% or less), the purple to blue light is efficiently used. Good light shielding. If the maximum transmittance in the wavelength range of 430 to 560 nm is 15% or less, blue to green light can be efficiently blocked. If the transmittance at 580 nm is 50% or less, the rising from the absorption region to the transmission region is gentle, and thus a solid-state imaging device with good color reproducibility can be manufactured. If the transmittance at 620 nm is 80% or more, the red color sensation signal can be sufficiently captured, so that a solid-state imaging device with good red color reproducibility can be produced.
- Example 2 coloring compositions (S-2) to (S-15) were prepared by changing the types and amounts of the respective components as shown in Table 2. Next, evaluation was performed in the same manner as in Example 1. The results are shown in Table 3.
- each component is as follows.
- D1-1 Kayrad DPEA-12 (Nippon Kayaku Co., Ltd., ethylene oxide modified dipentaerythritol hexaacrylate)
- D1-2 monoesterified product of dipentaerythritol pentaacrylate and succinic acid, dipentaerythritol hexaacrylate and a mixture of dipentaerythritol pentaacrylate (trade name TO-1382, manufactured by Toagosei Co., Ltd.)
- D2-1 Pentaerythritol tetraacrylate (Toagosei Co., Ltd., Aronix M-450)
- E1-1 Adeka Arcles NCI-930 (made by ADEKA Corporation)
- E1-2 Ethanone-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime)] (trade name IRGACURE
- Examples 10-14 Colored compositions (S-16) to (S-20) were prepared in the same manner as in Example 3, except that the amount of each component in Example 3 was changed as shown in Table 4. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 5.
- Example 3 the transmittance was evaluated in the same manner as in Example 3 except that the thickness of the coating film formed on the base film was changed as shown in Table 6. The results are shown in Table 6. Note that the evaluation results of sensitivity and pattern shape, development residue, surface roughness, film thickness uniformity, and storage stability of the colored composition in Examples 15 to 20 are the same as those in Example 3, and thus the description is omitted. .
- Preparation Examples 16-20 Pigment dispersions (R-16) to (R-20) were prepared in the same manner as in Preparation Example 3, except that the type of colorant used in Preparation Example 3 was changed as shown in Table 7.
- Examples 21-25 Colored compositions (S-21) to (S-25) were prepared in the same manner as in Example 3, except that the type of pigment dispersion used in Example 3 was changed as shown in Table 8. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 8. Note that the transmittance evaluation results in Examples 21 to 25 were the same as those in Example 3, and thus the description thereof was omitted.
- Preparation Examples 21 to 29 Pigment dispersions (R-21) to (R-29) were prepared in the same manner as in Preparation Example 3, except that the type of solvent used in Preparation Example 3 was changed as shown in Table 9.
- Examples 26-34 Colored compositions (S-26) to (S-34) were prepared in the same manner as in Example 3, except that the type of pigment dispersion used in Example 3 was changed as shown in Table 10. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 10. Note that the results of transmittance evaluation in Examples 26 to 34 are the same as those in Example 3, and thus description thereof is omitted.
- Examples 35-40 Colored compositions (S-35) to (S-40) were prepared in the same manner as in Example 3, except that the type of solvent used in Example 3 was changed as shown in Table 11. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 11. Note that the results of transmittance evaluation in Examples 35 to 40 are the same as those in Example 3, and thus description thereof is omitted.
- Preparation Examples 30 to 36 Pigment dispersions (R-30) to (R-36) were prepared in the same manner as in Preparation Example 3, except that the type of solvent used in Preparation Example 3 was changed as shown in Table 12.
- Example 3 colored compositions (S-41) to (S-49) were prepared in the same manner as in Example 3, except that the type of pigment dispersion used was changed as shown in Table 13. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 10. Note that the results of transmittance evaluation in Examples 41 to 49 are the same as those in Example 3, and thus description thereof is omitted.
- Examples 50-59 In the same manner as in Example 1 except that the type and amount of the pigment dispersion, the component (D) or the component (E) were changed as shown in Table 14, the coloring composition (S-50) to (S-59) was prepared. Next, evaluation was performed in the same manner as in Example 1. The results are shown in Table 14. Note that the results of transmittance evaluation in Examples 50 to 59 are the same as those in Example 3, and thus description thereof is omitted.
- Preparation Examples 37-50 Pigment dispersions (R-37) to (R-50) were prepared in the same manner as in Preparation Example 3, except that the types of components used in Preparation Example 3 were changed as shown in Table 15.
- Example 3 colored compositions (S-60) to (S-72) were prepared in the same manner as in Example 3 except that the type of pigment dispersion used was changed as shown in Table 15. Next, evaluation was performed in the same manner as in Example 3. The results are shown in Table 10. Note that the results of the transmittance evaluation in Examples 60 to 72 are the same as those in Example 3, and thus description thereof is omitted.
- the coloring composition of the present invention contains the pigment X and the isoindoline pigment as the colorant (A).
- the following can be said as compared with a colored composition using Pigment Red 254 or the like as a main pigment. 1) Since the transmittance at 400, 405, 410, 415, 420, 425, and 430 nm is small, purple to blue light can be efficiently blocked. 2) Since the maximum transmittance in the wavelength region of 430 to 560 nm is small, blue to green light can be shielded efficiently.
- the colored composition of the present invention it is possible to form a red pixel having good color reproducibility and hardly affecting the transmission region of the green pixel, which is extremely useful for the production of a solid-state imaging device. It can be preferably used.
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Abstract
Description
また、各画素において要求される色特性を得るために、2種類以上の顔料を用いて調色することが一般的である。例えば赤色画素では、主顔料にC.I.ピグメントレッド177、C.I.ピグメントレッド242、C.I.ピグメントレッド254等が用いられている(例えば、特許文献1~3参照)。
また、固体撮像素子に用いられるカラーフィルタにおいては、良好な色再現性を得るために、画素に対し透過曲線における吸収領域から透過領域へ移行する立ち上がりが緩やかであることも求められている。
(A)着色剤として(A1)下記式(X)で表される構造を有する顔料及び(A2)イソインドリン顔料を含み、かつ
(F)溶媒として(G)アルコール、ケトン及び乳酸アルキルエステルよりなる群から選ばれる少なくとも1種を含有する、着色組成物を提供するものである。
(1)波長400nmにおける透過率が30%以下である。
(2)波長430~560nmの波長領域の最大透過率が15%以下である。
(3)波長580nmにおける透過率が50%以下である。
(4)波長620nmにおける透過率が80%以上である。
Ra及びRbは、相互に独立に、一価の有機基を示し、
p及びqは、相互に独立に、0~5の整数を示す。〕
したがって、本発明の着色組成物は、CMOSイメージセンサ等の固体撮像素子の作製に極めて好適に使用することができる。
着色組成物
以下、本発明の着色組成物の構成成分について詳細に説明する。
Ra及びRbは、相互に独立に、一価の有機基を示し、
p及びqは、相互に独立に、0~5の整数を示す。〕
Ra及びRbにおける一価の有機基としては、例えば、炭化水素基、該炭化水素基のC-C結合間に炭素原子及び水素原子以外の原子を含む連結基を有する基等を挙げることができる。なお、Ra及びRbは、同一でも、異なっていてもよい。
炭化水素基としては、例えば、脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基を挙げることができる。ここで、本明細書において「脂環式炭化水素基」とは、環状構造を有さない脂肪族炭化水素基を除く概念である。また、本明細書において「脂環式炭化水素基」、「芳香族炭化水素基」とは、環構造のみからなる基だけでなく、当該環構造に更に2価の脂肪族炭化水素基が置換した基をも包含する概念であり、その構造中に少なくとも脂環式炭化水素又は芳香族炭化水素を含んでいればよい。炭化水素基は置換基を有してもいてもよく、置換基としては、例えば、ハロゲン原子、ニトロ基、ヒドロキシル基、アミノ基、アルコキシル基、アリールオキシ基等を挙げることができる。ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子を挙げることができる。アルコキシル基は直鎖及び分岐鎖のいずれの形態でもよく、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、tert-ブトキシ基等を挙げることができる。アリールオキシ基としては、例えば、フェノキシ基、ベンジルオキシ基等を挙げることができる。
p及びqは、相互に独立に、0~5の整数を示すが、1又は2が好ましく、1が更に好ましい。
上記分散助剤としては、顔料誘導体等が挙げられる。顔料誘導体としては、現像性に優れる着色組成物を得る観点から、酸性官能基を有する顔料誘導体が好ましい。酸性官能基としてはスルホ基、カルボキシル基、リン酸基等を挙げることができ、スルホ基、カルボキシル基がより好ましく、スルホ基が更に好ましい。具体的には、銅フタロシアニン、ジケトピロロピロール、キノフタロンのスルホン酸誘導体等を挙げることができる。
分散助剤の含有割合は、優れた色再現性及び高透過率を有し、他色の透過領域に影響を与えにくい赤色画素を形成する点から、(A)着色剤の合計含有量に対して0.1~10質量%が好ましく、0.2~5質量%がより好ましく、0.5~3質量%が更に好ましい。
本発明においては、(A1)顔料X、(A2)イソインドリン顔料及び任意に使用される他の着色剤と共に、更に(B)分散剤を含有せしめることができる。
(B)分散剤としては、例えば、ウレタン系分散剤、ポリエチレンイミン系分散剤、ポリオキシアルキレンアルキルエーテル系分散剤、ポリオキシアルキレンアルキルフェニルエーテル系分散剤、アルキレンオキサイド構造を有する繰り返し単位を含む分散剤、ポリ(アルキレングリコール)ジエステル系分散剤、ソルビタン脂肪酸エステル系分散剤、ポリエステル系分散剤、(メタ)アクリル系分散剤等が挙げられる。市販品としては、例えば、Disperbyk-2000、Disperbyk-2001、BYK-LPN6919、BYK-LPN21116、BYK-LPN22102(以上、ビックケミー(BYK)社製)等の(メタ)アクリル系分散剤、Disperbyk-161、Disperbyk-162、Disperbyk-165、Disperbyk-167、Disperbyk-170、Disperbyk-182(以上、ビックケミー(BYK)社製)、ソルスパース76500(ルーブリゾール(株)社製)等のウレタン系分散剤、ソルスパース24000(ルーブリゾール(株)社製)等のポリエチレンイミン系分散剤、アジスパーPB821、アジスパーPB822、アジスパーPB880、アジスパーPB881(以上、味の素ファインテクノ(株)社製)等のポリエステル系分散剤の他、BYK-LPN21324(ビックケミー(BYK)社製)を使用することができる。
R1は炭素数2~3のアルカンジイル基を示し、
R2は炭素数1~5のアルキル基を示し、
R3は水素原子又はメチル基を示し、
nは1~20の整数を示す。
nが2以上の場合、複数存在するR1は同一でも異なっていても良い。〕
R2におけるアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基等を挙げることができる。中でも、メチル基、エチル基、プロピル基、ブチル基が好ましい。
nは1~10が好ましく、1~5がより好ましい。
また、(B1)アルキレンオキサイド構造を有する繰り返し単位を含む分散剤は、ゲルパーミエーションクロマトグラフィー(以下、GPCと略す。)(溶出溶媒:テトラヒドロフラン)で測定したポリスチレン換算の重量平均分子量(Mw)が、通常1,000~50,000、好ましくは5,000~30,000である。
(B)分散剤は、アミン価が10~200mgKOH/gであるものが好ましく、更に50~180mgKOH/g、更に80~150mgKOH/gであるものが好ましい。なお、本発明における「アミン価」とは、分散剤固形分1gを中和するのに必要な酸と当量のKOHのmg数を表す。
(B1)アルキレンオキサイド構造を有する繰り返し単位を含む分散剤を用いる場合、(B1)アルキレンオキサイド構造を有する繰り返し単位を含む分散剤の含有割合は、(B)分散剤の合計含有量に対して50質量%以上が好ましく、80質量%以上がより好ましい。
本発明における(C)バインダー樹脂としては、特に限定されるものではないが、カルボキシル基、フェノール性水酸基等の酸性官能基を有する樹脂であることが好ましい。中でも、カルボキシル基を有する重合体(以下、「カルボキシル基含有重合体」とも称する。)が好ましく、例えば、1個以上のカルボキシル基を有するエチレン性不飽和単量体(以下、「不飽和単量体(c1)」とも称する。)と他の共重合可能なエチレン性不飽和単量体(以下、「不飽和単量体(c2)」とも称する。)との共重合体を挙げることができる。
これらの不飽和単量体(c1)は、単独で又は2種以上を混合して使用することができる。
N-フェニルマレイミド、N-シクロヘキシルマレイミドの如きN-位置換マレイミド;スチレン、α-メチルスチレン、p-ヒドロキシスチレン、p-ヒドロキシ-α-メチルスチレン、p-ビニルベンジルグリシジルエーテル、アセナフチレンの如き芳香族ビニル化合物;
これらの不飽和単量体(c2)は、単独で又は2種以上を混合して使用することができる。
i)不飽和単量体(c1)及び水酸基を有する重合性不飽和化合物を含有してなる単量体の重合体に、不飽和イソシアネート化合物を反応させて得られる重合体、
ii)不飽和単量体(c1)を含有してなる単量体の重合体に、オキシラニル基を有する重合性不飽和化合物を反応させて得られる重合体、
iii)オキシラニル基を有する重合性不飽和化合物及び不飽和単量体(c1)を含有してなる単量体の重合体に、不飽和単量体(c1)を反応させて得られる重合体、並びにiv)オキシラニル基を有する重合性不飽和化合物を含有してなる単量体の重合体に、不飽和単量体(c1)を反応させ、更に多塩基酸無水物を反応させて得られる重合体
なお、不飽和単量体(c1)とオキシラニル基との反応により生じる水酸基に、更に多塩基酸無水物を反応させることもできる。
上記オキシラニル基を有する重合性不飽和化合物としては、例えば、特開2010-044365号公報の段落〔0053〕に記載されているものを挙げることができる。
上記多塩基酸無水物としては、例えば、特開2014-098140号公報の段落〔0067〕に記載されているものを挙げることができる。
本発明において(D)重合性化合物とは、2個以上の重合可能な基を有する化合物をいう。重合可能な基としては、例えば、エチレン性不飽和基、オキシラニル基、オキセタニル基、N-アルコキシメチルアミノ基等を挙げることができる。本発明において、重合性化合物としては、2個以上の(メタ)アクリロイル基を有する化合物、又は2個以上のN-アルコキシメチルアミノ基を有する化合物が好ましい。
アルキレンオキサイド変性された多官能(メタ)アクリレートの中では、エチレンオキサイド及びプロピレンオキサイドから選ばれる少なくとも1種により変性されたトリメチロールプロパントリ(メタ)アクリレート、エチレンオキサイド及びプロピレンオキサイドから選ばれる少なくとも1種により変性されたペンタエリスリトールテトラ(メタ)アクリレート、エチレンオキサイド及びプロピレンオキサイドから選ばれる少なくとも1種により変性されたジペンタエリスリトールペンタ(メタ)アクリレート、エチレンオキサイド及びプロピレンオキサイドから選ばれる少なくとも1種により変性されたジペンタエリスリトールヘキサ(メタ)アクリレートが好ましい。
カルボキシル基を有する多官能(メタ)アクリレートの中では、ペンタエリスリトールトリアクリレートと無水こはく酸を反応させて得られる化合物、ジペンタエリスリトールペンタアクリレートと無水こはく酸を反応させて得られる化合物が好ましい。
本発明において、(D)重合性化合物は、単独で又は2種以上を混合して使用することができる。
本発明の着色組成物には、(E)光重合開始剤を含有せしめることができる。これにより、着色組成物に感放射線性を付与することができる。本発明に用いる光重合開始剤は、可視光線、紫外線、遠紫外線、電子線、X線等の放射線の露光により、上記重合性化合物の重合を開始しうる活性種を発生する化合物である。
本発明の着色組成物は、(F)溶媒として(G)アルコール、ケトン及び乳酸アルキルエステルよりなる群から選ばれる少なくとも1種を含有する。これにより、膜厚均一性及びパターニング性に優れた着色組成物を得ることができる。
エチレングリコールモノメチルエーテル(沸点124℃、以下同じ)、エチレングリコールモノエチルエーテル(135℃)、エチレングリコールモノ-n-プロピルエーテル(150℃)、エチレングリコールモノ-n-ブチルエーテル(171℃)、プロピレングリコールモノメチルエーテル(120℃)、プロピレングリコールモノエチルエーテル(133℃)、プロピレングリコールモノ-n-プロピルエーテル(150℃)、プロピレングリコールモノ-n-ブチルエーテル(170℃)等の(ポリ)アルキレングリコールモノアルキルエーテル;
メタノール(65℃)、エタノール(78℃)、プロパノール(97℃)、1-ブタノール(117℃)、イソプロパノール(82℃)、イソブタノール(108℃)、t-ブタノール(82℃)、3-メトキシ-1-ブタノール(161℃)、シクロヘキサノール(161℃)等の(シクロ)アルキルアルコール;
乳酸メチル(144℃)、乳酸エチル(153℃)等の乳酸アルキルエステル;
ジアセトンアルコール(166℃)等のケトアルコール;
メチルエチルケトン(80℃)、シクロヘキサノン(156℃)、2-ヘプタノン(151℃)、3-ヘプタノン(149℃)等のケトン
等を挙げることができる。
なお、(F1)成分は、それぞれ単独で又は2種以上を混合して使用することができる。
ジエチレングリコールモノメチルエーテル(194℃)、ジエチレングリコールモノエチルエーテル(202℃)、ジエチレングリコールモノ-n-ブチルエーテル(231℃)、トリエチレングリコールモノメチルエーテル(249℃)、トリエチレングリコールモノエチルエーテル(256℃)、ジプロピレングリコールモノメチルエーテル(190℃)、ジプロピレングリコールモノ-n-プロピルエーテル(212℃)、ジプロピレングリコールモノ-n-ブチルエーテル(229℃)、トリプロピレングリコールモノメチルエーテル(242℃)、トリプロピレングリコールn-ブチルエーテル(274℃)等の(ポリ)アルキレングリコールモノアルキルエーテル;
1,3-ブチレングリコール(208℃)等のグリコール;
オクタノール(195℃)、2-エチルヘキサノール(184℃)等の(シクロ)アルキルアルコール等を挙げることができる。
なお、(F4)成分は、単独で又は2種以上を混合して使用することができる。
γ-ブチロラクトン(204℃)等の環状エステル;
N-メチルピロリドン(202℃)等のラクタム等を挙げることができる。
なお、(F2)成分は、単独で又は2種以上を混合して使用することができる。
トルエン(111℃)、キシレン(139℃)等の芳香族炭化水素;
N,N-ジメチルホルムアミド(153℃)、N,N-ジメチルアセトアミド(165℃)等のアミド
等を挙げることができる。
なお、(F3)成分は、単独で又は2種以上を混合して使用することができる。
また、1気圧での沸点が180℃以上の高沸点溶媒、すなわち(F2)成分及び(F4)成分の含有割合は、全溶媒中に1~40質量%であることが好ましく、3~40質量%がより好ましく、5~35質量%が更に好ましく、10~30質量%が特に好ましい。
更に、(F3)成分の含有割合は、全溶媒中に10~97質量%であることが好ましく、20~90質量%がより好ましく、30~80質量%が更に好ましく、40~70質量%が特に好ましく、45~60質量%が最も好ましい。
本発明の着色組成物は、必要に応じて、種々の添加剤を含有することもできる。
添加剤としては、例えば、ガラス、アルミナ等の充填剤;ポリビニルアルコール、ポリ(フロオロアルキルアクリレート)類等の高分子化合物;フッ素系界面活性剤、シリコン系界面活性剤等の界面活性剤;ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリス(2-メトキシエトキシ)シラン、N-(2-アミノエチル)-3-アミノプロピルメチルジメトキシシラン、N-(2-アミノエチル)-3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルメチルジメトキシシラン、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、3-クロロプロピルメチルジメトキシシラン、3-クロロプロピルトリメトキシシラン、3-メタクリロイロキシプロピルトリメトキシシラン、3-メルカプトプロピルトリメトキシシラン等の密着促進剤;2,2-チオビス(4-メチル-6-t-ブチルフェノール)、2,6-ジ-t-ブチルフェノール、ペンタエリスリトールテトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート]、3,9-ビス[2-[3-(3-t-ブチル-4-ヒドロキシ-5-メチルフェニル)-プロピオニルオキシ]-1,1-ジメチルエチル]-2,4,8,10-テトラオキサ-スピロ[5・5]ウンデカン、チオジエチレンビス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート]等の酸化防止剤;2-(3-t-ブチル-5-メチル-2-ヒドロキシフェニル)-5-クロロベンゾトリアゾール、アルコキシベンゾフェノン類等の紫外線吸収剤;ポリアクリル酸ナトリウム等の凝集防止剤;マロン酸、アジピン酸、イタコン酸、シトラコン酸、フマル酸、メサコン酸、2-アミノエタノール、3-アミノ-1-プロパノール、5-アミノ-1-ペンタノール、3-アミノ-1,2-プロパンジオール、2-アミノ-1,3-プロパンジオール、4-アミノ-1,2-ブタンジオール等の残渣改善剤;こはく酸モノ〔2-(メタ)アクリロイロキシエチル〕、フタル酸モノ〔2-(メタ)アクリロイロキシエチル〕、ω-カルボキシポリカプロラクトンモノ(メタ)アクリレート等の現像性改善剤等を挙げることができる。
これらのうち、顔料の分散安定性に優れる着色組成物を得る観点から、調製方法(2)が好ましい。
本発明の着色硬化膜は、(A1)顔料X及び(A2)イソインドリン顔料を含み、膜厚0.5μmにおいて下記条件(1)~(4)のいずれか1つ以上を満たすものであり、本発明の着色組成物を用いて形成することができる。
(2)波長430~560nmの波長領域の最大透過率が15%以下である。
(3)波長580nmにおける透過率が50%以下である。
(4)波長620nmにおける透過率が80%以上である。
本発明の着色硬化膜が条件(3)を満たすことにより、緑色硬化膜との色分離性に優れる赤色硬化膜とすることができる。条件(3)において、波長580nmにおける透過率は、色再現性の観点から、40%以下がより好ましく、30%以下が更に好ましい。
本発明の着色硬化膜が条件(4)を満たすことにより、光感度に優れる赤色硬化膜とすることができる。条件(4)において、波長620nmにおける透過率は、色再現性の観点から、83%以上がより好ましく、85%以上が更に好ましい。
カラーフィルタを構成する着色硬化膜を形成する方法としては、第一に次の方法が挙げられる。まず、基板の表面上に、必要に応じて、画素を形成する部分を区画するように遮光層(ブラックマトリックス)を形成する。次いで、この基板上に、例えば、赤色の本発明の感放射線性着色組成物の液状組成物を塗布したのち、プレベークを行って溶媒を蒸発させ、塗膜を形成する。次いで、この塗膜にフォトマスクを介して露光したのち、アルカリ現像液を用いて現像して、塗膜の未露光部を溶解除去する。その後、ポストベークすることにより、赤色の画素パターン(着色硬化膜)が所定の配列で配置された画素アレイを形成する。
また、これらの基板には、所望により、シランカップリング剤等による薬品処理、プラズマ処理、イオンプレーティング、スパッタリング、気相反応法、真空蒸着等の適宜の前処理を施しておくこともできる。
また、上記アルカリ現像液としては、例えば、炭酸ナトリウム、炭酸水素ナトリウム、水酸化ナトリウム、水酸化カリウム、テトラメチルアンモニウムハイドロオキサイド、コリン、1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン、1,5-ジアザビシクロ-[4.3.0]-5-ノネン等の水溶液が好ましい。
現像処理法としては、シャワー現像法、スプレー現像法、ディップ(浸漬)現像法、パドル(液盛り)現像法等を適用することができる。現像条件は、常温で5~300秒が好ましい。
このようにして形成された画素の膜厚は、通常0.5~5μm、好ましくは1.0~3μmである。
着色硬化膜を形成する際に使用される基板や放射線の光源、また、プレベークやポストベークの方法や条件は、上記した第一の方法と同様である。このようにして、インクジェット方式により形成された画素の膜厚は、隔壁の高さと同程度である。
本発明の着色硬化膜は、膜厚が0.4~0.8μm、更に0.4~0.6μm、特に0.45~0.55μmであっても、良好な色再現性を有し、且つ緑色画素の透過領域に影響を与えにくい赤色画素として好適に用いることができる。
本発明の固体撮像素子は、本発明の着色硬化膜を具備するものである。とりわけ、本発明の着色組成物を用いて形成された赤色画素は、良好な色再現性を有し、且つ緑色画素の透過領域に影響を与えにくいため、固体撮像素子のカラーフィルタに好適である。また、本発明の固体撮像素子は適宜の構造を採ることができる。例えば、1つの実施の形態として、本発明の着色組成物を用いて、CMOS基板などの半導体基板上に、前述と同様の操作により着色画素(着色硬化膜)を形成することにより、特に分光特性及び色分離性に優れた固体撮像素子を作製することができる。
-赤色画素-
赤色画素は、良好な色再現性を有し、且つ緑色画素の透過領域に影響を与えにくい赤色画素とする観点から、(A1)顔料X及び(A2)イソインドリン顔料を含み、膜厚0.5μmにおいて上記条件(1)~(4)のいずれか1つ以上を満たすことが好ましい。また、近年の薄膜化に対する要求を満足する観点から、条件(5)として膜厚が、好ましくは0.7μm以下、より好ましくは0.6μm以下、更に好ましくは0.55μm以下、特に好ましくは0.5μm以下である。
条件(1)~(4)の中では、少なくとも条件(4)を満たすことが好ましく、少なくとも条件(2)及び条件(4)を満たすことがより好ましく、少なくとも条件(2)、(3)及び(4)を満たすことが更に好ましく、条件(1)~(4)を全て満たすことが特に好ましい。
条件(1)~(4)に関するこれらの好ましい態様と条件(5)に関する態様を同時に満たすことが好ましい。
波長400nmにおける透過率をより一層低下させる観点からは、上記質量比[(A1)/(A2)] は、80/20~65/35が好ましく、75/25~65/35がより好ましく、70/30~65/35が更に好ましい。このような態様により、前記条件(1)を満足する赤色画素とすることができる。
波長430~560nmの波長領域の最大透過率をより一層低下させる観点からは、上記質量比[(A1)/(A2)] は、85/15~70/30が好ましく、85/15~75/25がより好ましく、85/15~80/20が特に好ましい。このような態様により、前記条件(2)を満足する赤色画素とすることができる。
波長400nmにおける透過率及び波長430~560nmの波長領域の最大透過率をバランス良く低減させる観点からは、上記質量比[(A1)/(A2)]は、85/15~70/30が好ましく、80/20~70/30がより好ましい。このような態様により、前記条件(1)及び(2)を満足する赤色画素とすることができる。
緑色画素は、薄膜であっても良好な色再現性を有し、且つ青色画素及び赤色画素の透過領域に影響を与えにくい緑色画素とする観点から、着色剤としてC.I.ピグメントグリーン36、C.I.ピグメントグリーン58、C.I.ピグメントグリーン59を含むことが好ましく、C.I.ピグメントグリーン58、C.I.ピグメントグリーン59を含むことがより好ましい。
緑色画素は、緑色着色剤以外の他の着色剤を含んでいても良く、特に黄色着色剤を含むことが好ましい。黄色着色剤としては、薄膜であっても良好な色再現性を有し、且つ青色画素及び赤色画素の透過領域に影響を与えにくい緑色画素とする観点から、C.I.ピグメントイエロー138、C.I.ピグメントイエロー139、C.I.ピグメントイエロー150、C.I.ピグメントイエロー185が好ましく、C.I.ピグメントイエロー185がより好ましい。
青色画素は、薄膜であっても良好な色再現性を有し、且つ緑色画素の透過領域に影響を与えにくい青色画素を形成する観点から、着色剤としてはC.I.ピグメントブルー15:6、C.I.ピグメントバイオレット23を含むことが好ましい。
合成例1
冷却管と攪拌機を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート100質量部を仕込んで窒素置換した。80℃に加熱して、同温度で、プロピレングリコールモノメチルエーテルアセテート100質量部、ベンジルメタクリレート25質量部、スチレン10質量部、N-フェニルマレイミド20質量部、グリセロールモノメタクリレート5質量部、メタクリル酸10質量部、ω-カルボキシポリカプロラクトンモノアクリレート30質量部及び2,2'-アゾビスイソブチロニトリル3質量部の混合溶液を1時間かけて滴下し、この温度を保持して3時間重合した。その後、反応溶液の温度を100℃に昇温させ、さらに1時間重合することにより、バインダー樹脂溶液(固形分濃度40質量%)を得た。得られたバインダー樹脂は、Mwが9,800、Mnが6,000であった。このバインダー樹脂溶液を「バインダー樹脂(C-1)溶液」とする。
冷却管と攪拌機を備えたフラスコに、2,2'-アゾビスイソブチロニトリル3質量部及びプロピレングリコールモノメチルエーテルアセテート100質量部を仕込み、引き続きN-フェニルマレイミド12質量部、スチレン10質量部、メタクリル酸20質量部、2-ヒドロキシエチルメタクリレート15質量部、2-エチルヘキシルメタクリレート29質量部、ベンジルメタクリレート14質量部及びペンタエリスリトールテトラキス(3-メルカプトプロピオネート)(堺化学工業(株)製)5質量部を仕込んで、窒素置換した。その後ゆるやかに撹拌して、反応溶液の温度を80℃に上昇させ、この温度を3時間保持して重合した。その後、反応溶液の温度を100℃に昇温させ、さらに1時間重合した。
室温まで冷却した後、固形分濃度が40質量%になるようにプロピレングリコールモノメチルエーテルアセテートを添加することにより、バインダー樹脂溶液(固形分濃度40質量%)を得た。得られたバインダー樹脂は、Mwが9,700、Mnが5,700であった。このバインダー樹脂溶液を「バインダー樹脂(C-2)溶液」とする。
反応容器にプロピレングリコールモノメチルエーテルアセテート370質量部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度で下記モノマーおよび熱重合開始剤の混合物を1時間かけて滴下して重合反応を行った。
・メチルメタクリレート 10.0質量部
・n-ブチルメタクリレート 35.0質量部
・2-ヒドロキシエチルメタクリレート 15.0質量部
・2,2'-アゾビスイソブチロニトリル 4.0質量部
・パラクミルフェノールエチレンオキサイド変性アクリレート 20.0質量部(東亜合成株式会社製「アロニックスM110」)
室温まで冷却した後、減圧濃縮を行うことにより固形分濃度が40質量%になるように調節した。得られたバインダー樹脂は、Mw=40,000であった。このバインダー樹脂溶液を「バインダー樹脂(C-3)溶液」とする。
還流冷却器、滴下ロート及び攪拌機を備えた1Lのフラスコ内に窒素を適量流して窒素雰囲気とし、プロピレングリコールモノメチルエーテルアセテート100質量部を入れ、攪拌しながら85℃まで加熱した。次いで、滴下ポンプを用いて、該フラスコ内に、メタクリル酸19質量部、3,4-エポキシトリシクロ[5.2.1.02.6]デシルアクリレート(式(I-1)で表される化合物及び式(II-1)で表される化合物の混合物、モル比=50:50)171質量部をプロピレングリコールモノメチルエーテルアセテート40質量部に溶解した溶液を約5時間かけて滴下した。一方、別の滴下ポンプを用いて、重合開始剤2,2'-アゾビス(2,4-ジメチルバレロ二トリル)26質量部をプロピレングリコールモノメチルエーテルアセテート120質量部に溶解した溶液を約5時間かけてフラスコ内に滴下した。重合開始剤の滴下が終了した後、約3時間同温度に保持した。
室温まで冷却した後、固形分濃度が40質量%になるようにプロピレングリコールモノメチルエーテルアセテートを添加することにより、バインダー樹脂溶液(固形分濃度40質量%)を得た。得られたバインダー樹脂は、Mwが8,000、Mw/Mn=2.0であった。このバインダー樹脂溶液を「バインダー樹脂(C-4)溶液」とする。
合成例5
冷却管と攪拌機を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート90質量部を仕込んで窒素置換した後、90℃に加熱した。ここに、プロピレングリコールモノメチルエーテルアセテート50質量部、N-フェニルマレイミド12質量部、スチレン10質量部、2-エチルヘキシルエチレンオキサイド変性アクリレート(東亜合成社製アロニックスM120)38質量部、2-ヒドロキシエチルメタクリレート10質量部、メタクリル酸30質量部及びメルカプトプロピオン酸2質量部との混合溶液と、2,2'-アゾビスブチロニトリル5質量部及びプロピレングリコールモノメチルエーテルアセテート60質量部の混合溶液とを、2時間かけて各々滴下した。その後、この温度を保持して1時間重合した。次にグリシジルメタクリレート16.5質量部及びテトラブチルアンモニウムブロミド1.15質量部、4-メトキシフェノール0.34質量部を仕込み、110℃にて5時間付加反応を行った。
室温まで冷却した後、固形分濃度が40質量%になるようにプロピレングリコールモノメチルエーテルアセテートを添加することにより、バインダー樹脂溶液(固形分濃度40質量%)を得た。得られたバインダー樹脂は、Mw=11,600、Mn=4,800であった。このバインダー樹脂溶液を「バインダー樹脂(C-5)溶液」とする。
冷却管と攪拌機を備えたフラスコにプロピレングリコールモノメチルエーテルアセテート370質量部を仕込み、80℃に昇温し、フラスコ内を窒素置換した。ここに、パラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成社製アロニックスM110)18質量部、ベンジルメタクリレート10質量部、グリシジルメタクリレート18.2質量部、メタクリル酸メチル25質量部、及び2,2'-アゾビスイソブチロニトリル2.0質量部の混合物を2時間かけて滴下した。滴下後、更に100℃で3時間反応させた後、アゾビスイソブチロニトリル1.0質量部をプロピレングリコールモノメチルエーテルアセテート50質量部で溶解させたものを添加し、更に100℃で1時間反応を続けた。次に、容器内を空気置換に替え、アクリル酸9.3質量部(グリシジル基の当量)にトリスジメチルアミノフェノール0.5質量部及びハイドロキノン0.1質量部を上記容器内に投入し、120℃に昇温し、固形分酸価が0.5となるまで反応を行った。更に、テトラヒドロ無水フタル酸19.5質量部(生成した水酸基の当量)及びトリエチルアミン0.5質量部を加え、120℃で3.5時間反応させた。
室温まで冷却した後、減圧濃縮を行うことにより固形分濃度が40質量%になるように調節した。得られたバインダー樹脂は、Mw=19,000であった。このバインダー樹脂溶液を「バインダー樹脂(C-6)溶液」とする。
反応容器にプロピレングリコールモノメチルエーテルアセテート560質量部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度で下記モノマーおよび熱重合開始剤の混合物を1時間かけて滴下して重合反応を行った。
・メチルメタクリレート 23.0質量部
・n-ブチルメタクリレート 45.0質量部
・2-ヒドロキシエチルメタクリレート 70.5質量部
・2,2'-アゾビスイソブチロニトリル 8.0質量部
次に、得られた共重合体溶液338質量部に対して、下記化合物の混合物を70℃で3時間かけて滴下した。
・ラウリン酸ジブチル錫 0.4質量部
・シクロヘキサノン 120.0質量部
攪拌装置、滴下ロート、コンデンサー、温度計、ガス導入管を備えたフラスコにプロピレングリコールモノメチルエーテルアセテート67質量部、プロピレングリコールモノメチルエーテル33質量部を取り、窒素置換しながら攪拌し120℃に昇温した。次に、トリシクロデカニルメタクリレート11質量部、ベンジルメタクリレート31質量部、メタクリル酸23質量部からなるモノマー混合物にパーブチルOをモノマー混合物100質量部に対し1質量部を添加した。これを滴下ロートから2時間かけてフラスコに滴下し、さらに、120℃で2時間攪拌し共重合体を得た。次に、フラスコ内を空気置換に替え、グリシジルメタクリレート10質量部、トリフェニルホスフィン0.46質量部、およびメチルハイドロキノン0.08質量部を上記共重合体の溶液中に投入し120℃で反応を続け固形分酸価が150KOHmg/gとなったところで反応を終了した。
室温まで冷却した後、減圧濃縮を行うことにより固形分濃度が40質量%になるように調節した。得られたバインダー樹脂は、Mw=30,000であった。このバインダー樹脂溶液を「バインダー樹脂(C-8)溶液」とする。
合成例9
国際公開第2011/129078号パンフレットの実施例1を参考にして、ジメチルアミノエチルメタクリレート由来の繰り返し単位を有するAブロックと、ブチルメタクリレート、PME-200(日油株式会社製。メトキシポリエチレングリコールモノメタクリレート。式(1)においてR1がエチレン基、R2及びR3がメチル基、n≒4)及びメタクリル酸由来の繰り返し単位を有するBブロックからなるブロック共重合体(各繰り返し単位の共重合比は、ジメチルアミノエチルメタクリレート/ブチルメタクリレート/PME-200/メタクリル酸=22/47/26/5であり、Mwが10,000である。)を合成した。このブロック共重合体を「分散剤(B-1)」とする。
調製例1
フラスコ内を窒素置換した後、2,2'-アゾビスイソブチロニトリルを0.6質量部溶解したメチル-3-メトキシプロピオネート溶液を200質量部仕込んだ。引き続きtert-ブチルメタクリレートを37.5質量部、グリシジルメタクリレート62.5質量部を仕込んだ後、撹拌し、70℃にて6時間加熱した。冷却後、重合体を含有する樹脂溶液を得た。
次に、この樹脂溶液を33.3質量部(重合体を10部含有)、メチル-3-メトキシプロピオネートを31.9質量部、プロピレングリコールモノメチルエーテルを3.4質量部で希釈したのち、トリメリット酸を0.3質量部、3-グリシドキシプロピルトリメトキシシランを0.5質量部、商品名「FC-4432」(住友スリーエム(株)製)0.005質量部を溶解し、下地膜形成用組成物を調製した。
調製例1
着色剤として平均粒子径39nmのC.I.ピグメントレッド264を9.9質量部及び平均粒子径42nmのC.I.ピグメントイエロー185を1.1質量部、下記に示す分散助剤αを0.4質量部、分散剤として分散剤(B-1)(固形分濃度40質量%)を8.45質量部、バインダー樹脂(C-1)溶液(固形分濃度40質量%)を4.9質量部、溶媒としてプロピレングリコールモノメチルエーテルアセテート60.25質量部とプロピレングリコールモノエチルエーテル15.0質量部を用いて、ビーズミルにより混合・分散して顔料分散液(R-1)を調製した。なお、顔料の平均粒子径は、透過型電子顕微鏡(「H-7650」、日立ハイテクノロジーズ社製)によって観察される顔料の一次粒子100個の長径を測定し、この平均値を平均粒子径として算出した。
調製例1において、各成分の種類及び量を表1に示すように変更して、顔料分散液(R-2)~(R-15)を調製した。
・R264:C.I.ピグメントレッド264
・R254:C.I.ピグメントレッド254
・R242:C.I.ピグメントレッド242
・R177:C.I.ピグメントレッド177
・Y185:C.I.ピグメントイエロー185
・Y139:C.I.ピグメントイエロー139
・Y150:C.I.ピグメントイエロー150
・Y138:C.I.ピグメントイエロー138
但し、顔料名の後の括弧内の数値は、用いた顔料の平均粒子径を示す。
・LPN21116:BYK-LPN21116((メタ)アクリル系分散剤、ビックケミー社製、固形分濃度=40質量%。全繰り返し単位中のアルキレンオキサイド構造を有する繰り返し単位の含有割合が7質量%。)
・byk2001:Disperbyk-2001((メタ)アクリル系分散剤、ビックケミー社製、固形分濃度=46質量%)
・分散助剤α:特開2006-265528号公報の段落〔0089〕に記載の化合物C3(スルホ基を有するキノフタロン系顔料誘導体)
・分散助剤β:特開2011-246649号公報の段落〔0210〕に記載の化合物1(スルホ基を有するジケトピロロピロール系顔料誘導体)
・分散助剤γ:特開2004-067714号公報の段落〔0060〕に記載されている化合物(D-1)(カルボキシル基を有するジケトピロロピロール系顔料誘導体)
・PGME :プロピレングリコールモノメチルエーテル
・PGEE :プロピレングリコールモノエチルエーテル
・PNP :プロピレングリコールモノ-n-プロピルエーテル
・DAA :ジアセトンアルコール
・EL :乳酸エチル
・CHN :シクロヘキサノン
・γBL :γ-ブチロラクトン
・EDGAC:ジエチレングリコールモノエチルエーテルアセテート
・DPMA :ジプロピレングリコールメチルエーテルアセテート
・PGMEA:プロピレングリコールモノメチルエーテルアセテート
・EEP :3-エトキシプロピオン酸エチル
・MBA :3-メトキシブチルアセテート
実施例1
顔料分散液(R-1)を21.8質量部、バインダー樹脂(C-2)溶液(固形分濃度40質量%)を0.55質量部、重合性化合物としてカヤラッドDPEA-12(日本化薬株式会社製、エチレンオキサイド変性ジペンタエリスリトールヘキサアクリレート)0.65質量部、光重合開始剤として1,2-オクタンジオン,1-〔4-(フェニルチオ)フェニル〕-,2-(O-ベンゾイルオキシム)(BASF社製、Irgacure OXE01)0.18質量部、フッ素系界面活性剤としてメガファックF-554(DIC株式会社製)を0.1質量部、及びγ-ブチロラクトン7.3質量部を混合して、着色組成物(S-1)を得た。
着色組成物(S-1)の調製直後の粘度をE型粘度計(東京計器製)を用いて測定した。次に着色組成物(S-1)を遮光ガラス容器に充填し、密封状態で23℃にて14日間静置した後、E型粘度計(東京計器製)を用いて再度粘度を測定した。そして調製直後の粘度に対する14日間保存後の粘度の増加率を算出した。評価基準は以下の通りであり、結果を表3に示す。
A:増加率が5%未満
B:増加率が5%以上10%未満
C:増加率が10%以上
6インチシリコンウェハー上に、自動塗布現像装置(東京エレクトロン(株)製クリーントラック、商品名「MARK-Vz」)を用いて、前記下地膜形成用組成物をスピンコート法にて塗布した後、250℃で2分間ベークを行い、膜厚0.6μmの下地膜を形成した。
この下地膜上に着色組成物(S-1)をスピンコート法にて塗布した後、100℃で120秒間プレベークを行って、膜厚0.50μmの塗膜を形成した。
反射分光膜厚計(大塚電子製、FE-3000)にて、ウェハー中心及びウェハー中心から左右に1cm間隔の箇所(ウェハー中心を含めて計15箇所)で膜厚測定を行った。ウェハー内の最大膜厚と最小膜厚の差(Δft)を算出し、以下の基準で評価した。結果を表3に示す。
A:Δftが10nm未満。
B:Δftが10nm以上30nm未満。
C:Δftが30nm以上。
着色硬化膜の形成
6インチシリコンウェハー上に、自動塗布現像装置(東京エレクトロン(株)製クリーントラック、商品名「MARK-Vz」)を用いて、前記下地膜形成用組成物をスピンコート法にて塗布した後、250℃で2分間ベークを行い、膜厚0.6μmの下地膜を形成した。
この下地膜上に着色組成物(S-1)をスピンコート法にて塗布した後、100℃で120秒間プレベークを行って、膜厚0.50μmの塗膜を形成した。その後、得られた基板を室温に冷却し、基板上の塗膜に、フォトマスクを介して、i線ステッパー((株)ニコン製NSR-2205i12D)を用いた縮小投影露光にてパターン露光した。パターン露光は、15行×7列のマトリックス状に配列されたパターンの計105箇所に行なった。このとき、マトリックスのうちの上記15行は、最小露光量が50mJ/cm2、最大露光量が750mJ/cm2となるよう、50mJ/cm2間隔で1行ごとに露光量を変化させた条件となっている。また、上記7列は、焦点距離最適値(Focus0.0μm)を中心として0.2μm間隔で焦点距離を変化させた条件となっている。すなわち、中央1列を焦点距離最適値とし、1列ごとに焦点距離を変化させた条件としてある。また、フォトマスクとしては、1.1μm角の正方形ピクセルパターンが4mm×3mmの範囲内に配列するように硬化膜が形成されるフォトマスクを用いた。
同様の操作を行い、硬化膜を有するウェハーを2枚作製した。
上記基板(1)上の着色硬化膜の大きさと断面形状を、SU8030(走査電子顕微鏡、(株)日立製作所製)で観察した。評価基準は以下の通りであり、結果を表3に示す。C~Dの場合、感放射線性着色組成物の感度が低いと言える。
A:1.1μm角の正方形ピクセルパターンを形成可能な露光量が50~750mJ/cm2の中にあり、そのとき形成されるパターン断面形状は矩形であった。
B:1.1μm角の正方形ピクセルパターンを形成可能な露光量が50~750mJ/cm2の中にあるが、そのとき形成されるパターン断面形状は矩形ではなかった。
C:1.1μm角の正方形ピクセルパターンを形成可能な露光量が50~750mJ/cm2の中に無く、形成されるいずれのパターンも断面形状は矩形ではなかった。
D:未露光部がほとんど溶解しておらず、パターンが形成されていなかった。
上記基板(1)の未露光部及び基板(2)の未露光部を、S-9220(走査電子顕微鏡、(株)日立製作所製)で観察し、現像残渣を評価した。評価基準は以下の通りであり、結果を表3に示す。
A:基板(1)の未露光部及び基板(2)の未露光部には、残渣が全く確認されなかった。
B:基板(1)の未露光部に残渣がわずかに確認されたが、実用上問題のない程度であった。また、基板(2)の未露光部には、残渣が全く確認されなかった。
C:基板(1)の未露光部に残渣が多く確認された。また、基板(2)の未露光部に残渣がわずかに確認されたが、実用上問題のない程度であった。
D:基板(1)の未露光部に残渣が著しく多く確認された。また、基板(2)の未露光部に残渣が多く確認された。
E:基板(1)の未露光部及び基板(2)の未露光部の双方に、残渣が著しく多く確認された。
6インチシリコンウェハー上に、自動塗布現像装置(東京エレクトロン(株)製クリーントラック、商品名「MARK-Vz」)を用いて、前記下地膜形成用組成物をスピンコート法にて塗布した後、250℃で2分間ベークを行い、膜厚0.6μmの下地膜を形成した。
この下地膜上に着色組成物(S-1)をスピンコート法にて塗布した後、100℃で120秒間プレベークを行って、膜厚0.50μmの塗膜を形成した。その後、得られた基板を室温に冷却し、基板上の塗膜に、フォトマスクを介して、縮小投影露光((株)ニコン製NSR-2005i10D、波長365nmにて500mJ/cm2の露光量)を用いて露光した。
この基板を、自動塗布現象装置内で、0.3質量%テトラメチルアンモニウムハイドロオキサイド水溶液により30秒間パドル(液盛り)現像し、超純水によりリンスし、スピン乾燥した後、ホットプレート上にて200℃で300秒間ポストベークを行って、一辺1cmの正方形の着色硬化膜を有するシリコンウェハーを作製した。
このシリコンウェハー上に形成された着色硬化膜の上部の表面粗度を、デジタル・インスツルメンツ社製原子間力顕微鏡を用いて測定した。評価基準は以下の通りであり、結果を表3に示す。
A:表面粗度が40Å以下
B:表面粗度が40Åより大きく60Å以下
C:表面粗度が60Åより大きく80Å以下
D:表面粗度が80Åより大きいか、又は画素パターンが形成できないため評価不可
ガラス基板上に、着色組成物(S-1)をスピンコート法にて塗布した後、100℃で180秒間加熱し、塗膜を形成した。続いて、基板上の塗膜を全面露光(波長365nmにて1,000mJ/cm2の露光量)した。次いで、塗膜を、0.3質量%テトラメチルアンモニウムハイドロオキサイドを含有する水溶液に15秒間接触させた後、塗膜を水洗した。その後、200℃のホットプレートにて300秒間加熱することにより、膜厚0.50μmの着色硬化膜を有するガラスウェハーを得た。
分光光度計(日本分光(株)製、V-7300)を用いて、上記着色硬化膜を有するガラスウェハーの透過率(%T)を測定し、400、405、410、415、420、425、430、580、620nmにおける透過率を求めた。また、430~560nmの波長領域における最大透過率を求めた。結果を表3に示す。ただし表3の透過率は、ガラス基板対比での値であり、膜厚は触針式段差計(ヤマト科学(株)製、アルファステップIQ)にて測定した値である。各波長における透過率の評価基準は以下の通りであり、以下の評価基準を全て満たす着色硬化膜であれば、優れた色再現性及び高透過率を有し、他色の透過領域に影響を与えにくい着色硬化膜であると言える。
・400nmにおける透過率が30%以下であり、410nmにおける透過率が25%以下(より好ましくは20%以下、更に好ましくは15%以下)であり、420nmにおける透過率が20%以下(より好ましくは15%以下、更に好ましくは10%以下)であり、430nmにおける透過率が15%以下(より好ましくは13%以下、更に好ましくは10%以下)であれば、紫色~青色の光を効率よく遮光することができる。
・430~560nmの波長領域における最大透過率が15%以下であれば、青色~緑色の光を効率よく遮光することができる。
・580nmにおける透過率が50%以下であれば、吸収領域から透過領域へ移行する立ち上がりが緩やかであるため、色再現性が良好な固体撮像素子を作製することができる。
・620nmにおける透過率が80%以上であれば、赤色色感信号を充分に取り込めるので、赤色の色再現性の良好な固体撮像素子を作製することができる。
実施例1において、各成分の種類及び量を表2に示すように変更して、着色組成物(S-2)~(S-15)を調製した。次いで、実施例1と同様にして評価を行った。結果を表3に示す。
・D1-1:カヤラッドDPEA-12(日本化薬株式会社製、エチレンオキサイド変性ジペンタエリスリトールヘキサアクリレート)
・D1-2:ジペンタエリスリトールペンタアクリレートとこはく酸とのモノエステル化物、ジペンタエリスリトールヘキサアクリレート並びにジペンタエリスリトールペンタアクリレートの混合物(商品名TO-1382、東亞合成株式会社製)
・D2―1:ペンタエリスリトールテトラアクリレート(東亞合成株式会社製、アロニックスM-450)
・E1-1:アデカアークルズNCI-930(株式会社ADEKA社製)
・E1-2:エタノン-1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-1-(O-アセチルオキシム)](BASF社製、商品名IRGACURE OXE02)
・E1-3:1,2-オクタンジオン,1-〔4-(フェニルチオ)フェニル〕-,2-(O-ベンゾイルオキシム)(BASF社製、Irgacure OXE01)
・E2-1:2,4-ジエチルチオキサントン
・E2-2:2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)ブタン-1-オン(商品名イルガキュア369、BASF社製)
・G-1 :メガファックF-554(DIC株式会社製)
実施例3において、各成分の量を表4に示すように変更した以外は実施例3と同様にして、着色組成物(S-16)~(S-20)を調製した。次いで、実施例3と同様にして評価を行った。結果を表5に示す。
実施例3において、下地膜上に形成する塗膜の膜厚を表6に示すように変更した以外は実施例3と同様にして、透過率の評価を行った。結果を表6に示す。なお、実施例15~20における感度及びパターン形状、現像残渣、表面粗度、膜厚均一性、並びに着色組成物の保存安定性の評価結果は実施例3と同一であるため、記載を省略した。
調製例3において、用いる着色剤の種類を表7に示すように変更した以外は調製例3と同様にして、顔料分散液(R-16)~(R-20)を調製した。
実施例3において、用いる顔料分散液の種類を表8に示すように変更した以外は実施例3と同様にして、着色組成物(S-21)~(S-25)を調製した。次いで、実施例3と同様にして評価を行った。結果を表8に示す。なお、実施例21~25における透過率の評価結果は実施例3と同一であるため、記載を省略した。
調製例3において、用いる溶媒の種類を表9に示すように変更した以外は調製例3と同様にして、顔料分散液(R-21)~(R-29)を調製した。
実施例3において、用いる顔料分散液の種類を表10に示すように変更した以外は実施例3と同様にして、着色組成物(S-26)~(S-34)を調製した。次いで、実施例3と同様にして評価を行った。結果を表10に示す。なお、実施例26~34における透過率評価の結果は実施例3と同一であるため、記載を省略した。
実施例3において、用いる溶媒の種類を表11に示すように変更した以外は実施例3と同様にして、着色組成物(S-35)~(S-40)を調製した。次いで、実施例3と同様にして評価を行った。結果を表11に示す。なお、実施例35~40における透過率評価の結果は実施例3と同一であるため、記載を省略した。
調製例3において、用いる溶媒の種類を表12に示すように変更した以外は調製例3と同様にして、顔料分散液(R-30)~(R-36)を調製した。
実施例3において、用いる顔料分散液の種類を表13に示すように変更した以外は実施例3と同様にして、着色組成物(S-41)~(S-49)を調製した。次いで、実施例3と同様にして評価を行った。結果を表10に示す。なお、実施例41~49における透過率評価の結果は実施例3と同一であるため、記載を省略した。
実施例1において、顔料分散液、(D)成分又は(E)成分の種類及び量を表14に示すように変更した以外は実施例1と同様にして、着色組成物(S-50)~(S-59)を調製した。次いで、実施例1と同様にして評価を行った。結果を表14に示す。なお、実施例50~59における透過率評価の結果は実施例3と同一であるため、記載を省略した。
調製例3において、用いる成分の種類を表15に示すように変更した以外は調製例3と同様にして、顔料分散液(R-37)~(R-50)を調製した。
実施例3において、用いる顔料分散液の種類を表15に示すように変更した以外は実施例3と同様にして、着色組成物(S-60)~(S-72)を調製した。次いで、実施例3と同様にして評価を行った。結果を表10に示す。なお、実施例60~72における透過率評価の結果は実施例3と同一であるため、記載を省略した。
1)400、405、410、415、420、425、430nmにおける透過率が小さいので、紫色~青色の光を効率よく遮光することができる。
2)430~560nmの波長領域における最大透過率が小さいので、青色~緑色の光を効率よく遮光することができる。
3)580nmにおける透過率が小さいので、吸収領域から透過領域へ移行する立ち上がりが緩やかであるため、色再現性が良好な固体撮像素子を作製することができる。
4)620nmにおける透過率が大きいので、赤色色感信号を充分に取り込めるので、赤色の色再現性の良好な固体撮像素子を作製することができる。
5)図1に示すように、比較例1の着色剤としてC.I.ピグメントレッド254/C.I.ピグメントイエロー185=80/20を含有する比較例1の赤色硬化膜は、透過曲線における吸収領域から透過領域へ移行する立ち上がりが急であるため、緑色硬化膜の透過領域との重なりが多く、緑色画素との色分離性に影響を与えやすい。これに対し、C.I.ピグメントレッド264/C.I.ピグメントイエロー185=80/20を含有する実施例3の赤色硬化膜は、透過曲線における吸収領域から透過領域へ移行する立ち上がりが緩やかであるため、緑色硬化膜の透過領域との重なりが少なく、緑色画素との色分離性に影響を与え難い。
6)顔料含有量が45質量%である実施例12の赤色硬化膜は、顔料含有量が50質量%である比較例1の赤色硬化膜に比べて580nmでの透過率に優れる点を除き、同等の透過率を有している。したがって、本発明の着色組成物は、より少ない顔料含有量でカラーフィルタにおいて要求される色分離性を達成することが可能である。
したがって、本発明の着色組成物を用いれば、良好な色再現性を有し、且つ緑色画素の透過領域に影響を与えにくい赤色画素を形成することが可能であり、固体撮像素子の作製に極めて好適に使用することができる。
Claims (15)
- (G)成分を全溶媒に対して3~40質量%含有する、請求項1に記載の着色組成物。
- (A1)成分と(A2)成分との質量比[(A1)/(A2)] が85/15~65/35である、請求項1又は2に記載の着色組成物。
- (A2)成分がC.I.ピグメントイエロー185である、請求項1~3のいずれか1項に記載の着色組成物。
- (A1)成分がC.I.ピグメントレッド264である、請求項1~4のいずれか1項に記載の着色組成物。
- (D)成分がアルキレンオキサイド変性された多官能(メタ)アクリレート及びカルボキシル基を有する多官能(メタ)アクリレートよりなる群から選ばれる少なくとも1種を含む、請求項1~5のいずれか1項に記載の着色組成物。
- 更に(E)光重合開始剤として(E1)O-アシルオキシム系化合物、並びに(E2)チオキサントン系化合物及びアセトフェノン系化合物よりなる群から選ばれる少なくとも1種の化合物を含有する、請求項1~6のいずれか1項に記載の着色組成物。
- (E1)成分と(E2)成分との質量比[(E1)/(E2)]が20/80~80/20である、請求項7に記載の着色組成物。
- 更に(B)分散剤として(B1)アルキレンオキサイド構造を有する繰り返し単位を有する分散剤を含有する、請求項1~8のいずれか1項に記載の着色組成物。
- (B1)成分を構成するアルキレンオキサイド構造を有する繰り返し単位の含有割合が全繰り返し単位中に3~40質量%である、請求項9に記載の着色組成物。
- (B1)成分を構成するアルキレンオキサイド構造を有する繰り返し単位の含有割合が全繰り返し単位中に13~27質量%である、請求項10に記載の着色組成物。
- (F)成分中の1気圧での沸点が180℃以上の溶媒の含有割合が1~40質量%である、請求項1~11のいずれか1項に記載の着色組成物。
- (A)着色剤に含まれる顔料の平均粒子径が15~100nmである、請求項1~12のいずれか1項に記載の着色組成物。
- 請求項14に記載の着色硬化膜を具備する固体撮像素子。
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JP2018105911A (ja) * | 2016-12-22 | 2018-07-05 | 東洋インキScホールディングス株式会社 | カラーフィルタ用着色組成物およびカラーフィルタ |
JP2018159749A (ja) * | 2017-03-22 | 2018-10-11 | 東洋インキScホールディングス株式会社 | 有機el表示装置用赤色着色組成物、有機el表示装置用カラーフィルタ及び有機el表示装置 |
JP2019038977A (ja) * | 2017-08-29 | 2019-03-14 | 荒川化学工業株式会社 | ワニス組成物、オフセット印刷インキ及び印刷物 |
WO2023162889A1 (ja) * | 2022-02-25 | 2023-08-31 | 株式会社日本触媒 | 重合体及びその感光性樹脂組成物 |
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KR101943340B1 (ko) * | 2014-12-25 | 2019-01-29 | 후지필름 가부시키가이샤 | 착색 조성물, 착색 조성물의 제조 방법, 컬러 필터, 패턴 형성 방법, 컬러 필터의 제조 방법, 고체 촬상 소자, 및 화상 표시 장치 |
KR102134633B1 (ko) * | 2016-11-25 | 2020-07-16 | 삼성에스디아이 주식회사 | 감광성 수지 조성물, 이를 이용한 블랙 화소 격벽층 및 디스플레이 장치 |
TWI751313B (zh) * | 2017-03-29 | 2022-01-01 | 日商住友化學股份有限公司 | 著色硬化性樹脂組成物 |
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KR20230008222A (ko) | 2023-01-13 |
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TW201614013A (en) | 2016-04-16 |
JP6583275B2 (ja) | 2019-10-02 |
KR20170041708A (ko) | 2017-04-17 |
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JPWO2016024497A1 (ja) | 2017-06-01 |
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