WO2020184244A1 - Coloring composition, cured film, pattern forming method, color filter, solid-state image sensor, and image display apparatus - Google Patents
Coloring composition, cured film, pattern forming method, color filter, solid-state image sensor, and image display apparatus Download PDFInfo
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- WO2020184244A1 WO2020184244A1 PCT/JP2020/008604 JP2020008604W WO2020184244A1 WO 2020184244 A1 WO2020184244 A1 WO 2020184244A1 JP 2020008604 W JP2020008604 W JP 2020008604W WO 2020184244 A1 WO2020184244 A1 WO 2020184244A1
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- coloring composition
- pigment
- compound
- mass
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Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
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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
- G03F7/004—Photosensitive materials
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
Definitions
- the present invention relates to a coloring composition containing a diketopyrrolopyrrole pigment.
- the present invention also relates to a cured film using a coloring composition, a pattern forming method, a color filter, a solid-state image sensor, and an image display device.
- a color filter usually includes pixels (coloring patterns) of the three primary colors of red, green, and blue, and plays a role of decomposing transmitted light into the three primary colors.
- the color filter is formed by using a coloring composition containing a coloring material such as a pigment. Further, in the coloring composition for forming red pixels, a diketopyrrolopyrrole pigment or the like is used as a coloring material.
- Color Index Pigment Red 254 (a compound in which R 1 and R 2 in the following structural formula are chlorine atoms) and Color Index Pigment Red 264 (A compound in which R 1 and R 2 in the following structural formula are phenyl groups) or a coloring composition using a compound in which R 1 and R 2 in the following structural formula are bromine atoms is described.
- an object of the present invention is to provide a coloring composition capable of forming a cured film having excellent heat resistance.
- Another object of the present invention is to provide a cured film using a coloring composition, a pattern forming method, a color filter, a solid-state image sensor, and an image display device.
- the present invention provides the following.
- ⁇ 1> Contains a diketopyrrolopyrrole pigment, a magenta color dye, and a compound having a curable group.
- the diketopyrrolopyrrole pigment is a coloring composition containing a pigment A having a structure in which an aromatic ring group in which an electron-donating group is introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton.
- the electron-donating group of the pigment A is an alkyl group having 1 to 3 carbon atoms.
- ⁇ 4> The coloring composition according to any one of ⁇ 1> to ⁇ 3>, wherein the aromatic ring group contained in the pigment A is a group represented by the following formula (AR-1); In the formula, R 1 represents a substituent, R 2 represents an electron donating group, n represents an integer from 0 to 4, and the wavy line represents the binding site with the diketopyrrolopyrrole skeleton.
- AR-1 aromatic ring group contained in the pigment A
- R 1 represents a substituent
- R 2 represents an electron donating group
- n represents an integer from 0 to 4
- the wavy line represents the binding site with the diketopyrrolopyrrole skeleton.
- ⁇ 5> The coloring composition according to any one of ⁇ 1> to ⁇ 4>, wherein the pigment A is a compound represented by the following formula (1); In the formula, R 11 and R 12 each independently represent a substituent, R 21 and R 22 each independently represent an electron donating group, and n 11 and n 12
- the magenta color dye is any of ⁇ 1> to ⁇ 7>, which comprises at least one selected from the group consisting of a quinacridone compound, a xanthene compound, a triarylmethane compound, a cyanine compound, an anthraquinone compound and a dipyrromethene compound.
- the coloring composition according to one.
- ⁇ 9> The coloring composition according to any one of ⁇ 1> to ⁇ 7>, wherein the magenta color dye contains a salt of a cationic cyanine chromophore and an imide anion.
- the coloring composition according to any one of ⁇ 1> to ⁇ 9> which contains 1 to 50 parts by mass of the magenta color dye with respect to 100 parts by mass of the pigment A.
- the coloring composition according to any one of ⁇ 1> to ⁇ 10> further comprising a yellow colorant.
- the compound having a curable group includes a compound having an ethylenically unsaturated group, and the coloring composition further contains a photopolymerization initiator, according to any one of ⁇ 1> to ⁇ 11>.
- Coloring composition. ⁇ 13> The coloring composition according to any one of ⁇ 1> to ⁇ 12>, wherein the content of the pigment A in the total solid content of the coloring composition is 40% by mass or more.
- ⁇ 14> The coloring composition according to any one of ⁇ 1> to ⁇ 13>, wherein the diketopyrrolopyrrole pigment contains two or more of the pigments A.
- ⁇ 15> The coloring composition according to any one of ⁇ 1> to ⁇ 14>, wherein the diketopyrrolopyrrole pigment further contains a diketopyrrolopyrrole pigment other than the pigment A.
- ⁇ 16> The coloring composition according to any one of ⁇ 1> to ⁇ 15>, which is used for a solid-state image sensor.
- ⁇ 17> The coloring composition according to any one of ⁇ 1> to ⁇ 16>, which is used for a color filter.
- ⁇ 18> A cured film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 17>.
- ⁇ 19> A step of forming a coloring composition layer on a support using the coloring composition according to any one of ⁇ 1> to ⁇ 17>, and a coloring composition layer by a photolithography method or a dry etching method.
- a pattern forming method comprising a step of forming a pattern with respect to a pattern.
- ⁇ 20> A color filter having the cured film according to ⁇ 18>.
- ⁇ 21> A solid-state image sensor having the cured film according to ⁇ 18>.
- ⁇ 22> An image display device having the cured film according to ⁇ 18>.
- the present invention it is possible to provide a coloring composition capable of forming a cured film having excellent heat resistance. Further, the present invention can provide a cured film using a coloring composition, a pattern forming method, a color filter, a solid-state image sensor, and an image display device.
- the contents of the present invention will be described in detail below.
- "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- (meth) acrylate represents both acrylate and methacrylate, or either, and "(meth) acrylic” represents both acrylic and methacrylic, or “(meth) acrylate.”
- Acryloyl "represents both acryloyl and / or methacryloyl.
- the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the term pigment means a compound that is difficult to dissolve in a solvent. For example, the pigment has a solubility in 100 g of water at 23 ° C.
- the term dye means a compound that is easily soluble in a solvent.
- the dye has a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., preferably 0.1 g or more, and more preferably 1 g or more.
- the total solid content refers to the total mass of components excluding the solvent from all components of the composition.
- the term "process" is included in this term not only as an independent process but also as long as the desired action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
- the coloring composition of the present invention contains a diketopyrrolopyrrole pigment, a magenta color dye, and a compound having a curable group, and the diketopyrrolopyrrole pigment has an electron donating group introduced into the aromatic ring. It is characterized by containing a pigment A having a structure in which an aromatic ring group is bonded to a diketopyrrolopyrrole skeleton.
- the coloring composition of the present invention By using the coloring composition of the present invention, a cured film having excellent heat resistance can be formed. In general, the higher the pigment concentration in the film, the more easily the heat resistance tends to decrease. However, the coloring composition of the present invention has heat resistance even if the content of the pigment A in the total solid content is increased. A cured film having excellent properties can be formed. Although the detailed mechanism is unknown, by using the pigment A and the magenta color dye together, the magenta color dye is adsorbed on the surface of the pigment A, so that the crystal growth accompanying the heating of the pigment A is suppressed, and the heat resistance is excellent. It is presumed that a cured film can be formed.
- a red pigment when used as the pigment A, by using the pigment A and the magenta color dye in combination, it is possible to enhance the light blocking property of light having a wavelength near 500 nm (for example, a wavelength of 500 to 550 nm), and the green color. It is possible to form a cured film suitable for red pixels having spectral characteristics excellent in color separation from magenta and blue. Further, since the pigment A has a higher red color value than the conventional red pigment, it is possible to form a cured film having desired spectral characteristics even if it is a thin film.
- the transition moment is increased by increasing the HOMO (Highest Occupied Molecular Orbital) -LUMO (Lowest Unellad Molecular Orbital) transition.
- the color value of red is high because the molar absorption coefficient ⁇ in the red wavelength region (for example, 450 to 600 nm) of the pigment A is increased.
- the desired spectroscopy can be performed with a blending amount smaller than the blending amount required to achieve the same spectral characteristics as the conventional red pigment. Since it can be achieved, the amount of ingredients other than pigments can be increased, and the degree of freedom in formulation design is high.
- the coloring composition of the present invention can be preferably used as a coloring composition for a solid-state image sensor. Moreover, the coloring composition of the present invention can be preferably used as a coloring composition for a color filter. Specifically, it can be preferably used as a coloring composition for forming pixels of a color filter, and more preferably used as a coloring composition for forming red pixels. Further, the coloring composition of the present invention can be more preferably used as a coloring composition for forming pixels of a color filter used in a solid-state image sensor.
- the colored composition of the present invention has a transmittance of light having a wavelength of 650 to 700 nm at least one of the above-mentioned film thicknesses when a film having a film thickness of 0.5 to 1.0 ⁇ m after drying is formed. It is preferably 85% or more, more preferably 90% or more, and further preferably 95% or more. Further, at least one of the above-mentioned film thicknesses, the transmittance of light having a wavelength of 400 to 550 nm is preferably 10% or less, more preferably 5% or less, still more preferably 2% or less. ..
- the coloring composition of the present invention contains a diketopyrrolopyrrole pigment.
- the diketopyrrolopyrrole pigment used in the coloring composition of the present invention is preferably a red pigment.
- the diketopyrrolopyrrole pigment preferably has a solubility in 100 g of water at 23 ° C. and a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., preferably less than 0.1 g, and more preferably 0.01 g or less. preferable.
- the coloring composition of the present invention is a pigment A (hereinafter, pigment A) having a structure in which an aromatic ring group having an electron donating group introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton as a diketopyrrolopyrrole pigment. ) Is contained.
- pigment A having a structure in which an aromatic ring group having an electron donating group introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton as a diketopyrrolopyrrole pigment.
- An electron-donating group is an atomic group that donates an electron to an atomic group substituted by an inductive effect or a resonance effect in organic electron theory.
- Examples of the electron-donating group include those having a negative value as the substituent constant ( ⁇ p (para)) of Hammett's law.
- the Hammett equation substituent constant ( ⁇ p (para)) can be quoted from the 5th edition of the Basics of Chemistry Handbook (page II-380).
- Specific examples of the electron donating group include a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group and an amino group.
- the number of carbon atoms of the alkyl group, the alkoxy group and the alkylthio group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. These groups may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
- the aryloxy group preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms. Examples of the amino group include a group represented by ⁇ NRa 1 Ra 2 .
- Ra 1 and Ra 2 independently represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, respectively. Ra 1 and Ra 2 may be combined to form a ring.
- the alkyl group represented by Ra 1 and Ra 2 has a preferably 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 8 carbon atoms.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the number of carbon atoms of the aryl group represented by Ra 1 and Ra 2 is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
- the heterocyclic group represented by Ra 1 and Ra 2 may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a fused ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- an alkyl group, an alkoxy group, and an amino group are preferable because the effect of the present invention can be obtained more remarkably, and in addition to the above reasons, the spectral characteristics suitable for red color are further adjusted.
- Alkyl groups and alkoxy groups are more preferable because they are easy to use, alkyl groups are more preferable, and alkyl groups having 1 to 3 carbon atoms are particularly preferable.
- the aromatic ring group is preferably a group represented by the formula (AR-1).
- R 1 represents a substituent
- R 2 represents an electron donating group
- n represents an integer from 0 to 4
- the wavy line represents the binding site with the diketopyrrolopyrrole skeleton.
- examples of the substituent represented by R 1 include the group mentioned in Substituent T described later and the electron donating group described above, and the substituent is preferably an electron donating group.
- n pieces of R 1 may be the same or may be different from each.
- the electron-donating group represented by R 2 includes the above-mentioned electron-donating group, and the preferred range is also the same.
- n represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 0 or 1. It is particularly preferable that it is 1.
- the wavy line represents the binding site with the diketopyrrolopyrrole skeleton.
- the diketopyrrolopyrrole skeleton means the following structure.
- the wavy line represents the bonding position with a substituent such as a group represented by the equation (AR-1).
- substituent other than the group represented by the formula (AR-1) include an aryl group and the like.
- the aryl group may have a substituent. Examples of the substituent include the groups listed in Substituent T described later.
- the pigment A is preferably a compound represented by the following formula (1), and more preferably a compound represented by the following formula (2) because more excellent heat resistance can be easily obtained.
- R 11 and R 12 each independently represent a substituent.
- R 21 and R 22 each independently represent an electron donating group.
- n11 and n12 each independently represent an integer of 0 to 4.
- substituent represented by R 11 and R 12 examples include the group mentioned in Substituent T described later and the electron donating group described above, and are preferably electron donating groups. If n11 is 2 or more, n11 amino R 11 may be the same or may be different from each. Also, in the case of n12 is 2 or more, n12 amino R 12 may be the same or may be different from each.
- Examples of the electron-donating group represented by R 21 and R 22 include the above-mentioned electron-donating group, and the preferred range is also the same.
- n11 and n12 each independently represent an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 0 or 1. Is particularly preferable.
- the substituent T includes a halogen atom, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, -ORt 1 , -CORt 1 , -COORt 1 , -OCORt 1 , -NRt 1 Rt 2 , and -NHCORt 1. , -CONRt 1 Rt 2 , -NHCONRt 1 Rt 2 , -NHCOORt 1 , -SRt 1 , -SO 2 Rt 1 , -SO 2 ORt 1 , -NHSO 2 Rt 1 or -SO 2 NRt 1 Rt 2 .
- Rt 1 and Rt 2 independently represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, respectively.
- Rt 1 and Rt 2 may be combined to form a ring.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- the number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the heterocyclic group may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a fused ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- the alkyl group, aryl group and heterocyclic group may have a substituent or may be unsubstituted. Examples of the substituent include the substituent described in the above-mentioned Substituent T.
- pigment A examples include compounds having the following structures.
- the diketopyrrolopyrrole pigment used in the coloring composition of the present invention may contain only one type of pigment A, and may contain two or more types of pigment A. When only one type of pigment A is contained, it is easy to form a cured film with less color unevenness. When two or more kinds of pigments A are contained, it is easy to adjust the spectral characteristics of the cured film.
- the pigment A used in the present invention is preferably a red pigment.
- pigment A which is a red pigment, and a magenta color dye in combination, a cured film suitable for red pixels having excellent heat resistance and spectral characteristics excellent in color separation from green, blue, etc. is formed. can do.
- the coloring composition of the present invention can contain a diketopyrrolopyrrole pigment other than the pigment A described above (hereinafter, also referred to as another diketopyrrolopyrrole pigment).
- the other diketopyrrolopyrrole pigment is preferably a red pigment.
- examples of other diketopyrrolopyrrole pigments include compounds represented by the following formula (10).
- R 31 and R 32 independently represent a hydrogen atom, a halogen atom or a phenyl group, respectively.
- Examples of the halogen atom represented by R 31 and R 32 include a fluorine atom, a chlorine atom, and a bromine atom.
- the diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, described in paragraphs 0016 to 0022 of Patent No. 6248838 As another diketopyrrolopyrrole pigment, the diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, described in paragraphs 0016 to 0022 of Patent No. 6248838.
- the diketopyrrolopyrrole compound described in International Publication No. 2012/102399, the diketopyrrolopyrrole compound described in WO2012 / 117965, and the like can also be used.
- diketopyrrolopyrrole pigments include the following compounds.
- the content of the pigment A is preferably 35% by mass or more, more preferably 40% by mass or more, still more preferably 45% by mass or more, and 50% by mass, based on the total solid content of the coloring composition.
- the above is even more preferable.
- the upper limit can be 80% by mass or less.
- the diketopyrrolopyrrole pigment contained in the coloring composition may be substantially only pigment A, or may further contain other diketopyrrolopyrrole pigments.
- the diketopyrrolopyrrole pigment is substantially only pigment A, it is easy to form a cured film with less color unevenness.
- the diketopyrrolopyrrole pigment is substantially only pigment A, it means that the proportion of pigment A in the total mass of the diketopyrrolopyrrole pigment contained in the coloring composition is 99% by mass or more. This means that it is preferably 99.5% by mass or more, more preferably 99.9% by mass or more, and particularly preferably composed of only the pigment A.
- the diketopyrrolopyrrole pigment contains another diketopyrrolopyrrole pigment in addition to the pigment A, it is easy to adjust the spectral characteristics of the cured film.
- the content of the other diketopyrrolopyrrole pigment is preferably 0.1 to 50 parts by mass with respect to 100 parts by mass of the pigment A. It is more preferably 1 to 35 parts by mass, and further preferably 5 to 20 parts by mass.
- the content of the diketopyrrolopyrrole pigment (the total amount thereof when other diketopyrrolopyrrole pigments are contained in addition to the pigment A) is preferably 25% by mass or more based on the total solid content of the coloring composition. It is more preferably 30% by mass or more, further preferably 35% by mass or more, and even more preferably 40% by mass or more.
- the upper limit can be 80% by mass or less.
- magenta color dye contains a magenta dye.
- the magenta color is the hue of the complementary color of green.
- the complementary color is a combination of colors having a relationship of being located opposite to each other on the color wheel.
- the magenta color dye is a dye that exhibits a magenta hue.
- magenta dye used in the present invention examples include dyes having a high absorbance of light having a green wavelength and a low absorbance of light having a red and blue wavelength, and having a light absorbance in the wavelength range of 500 to 550 nm. It is preferable that the dye is high and has low light absorbance in the wavelength range of 400 to 480 nm and low light absorbance in the wavelength range of 600 to 700 nm.
- the magenta color dye used in the present invention preferably has ⁇ represented by the following formula (1) of 150 nm or less, more preferably 100 nm or less, and further preferably 50 nm or less.
- ⁇ 1 a wavelength on the shorter wavelength side than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance at the maximum absorption wavelength of the magenta color dye is 1
- ⁇ 2 is the maximum absorption wavelength of the magenta color dye. This is a wavelength on the longer wavelength side than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance of is 1.
- the maximum absorption wavelength of the magenta dye is preferably in the wavelength range of 450 to 600 nm, more preferably in the range of 475 to 575 nm, and even more preferably in the range of 500 to 550 nm.
- the magenta color dye used in the present invention has a ratio (A1 / A2) of 0 between the maximum value A1 of the absorbance of light in the wavelength range of 400 to 480 nm and the minimum value A2 of the absorbance of light in the wavelength range of 500 to 550 nm. It is preferably 2 to 0.8, more preferably 0.3 to 0.7, and even more preferably 0.4 to 0.6. Further, the magenta color dye has a ratio (A3 / A2) of 0.3 or less between the maximum value A3 of the absorbance of light in the wavelength range of 600 to 700 nm and the minimum value A2 of the absorbance of light in the wavelength range of 500 to 550 nm.
- magenta dye has a ratio (A3 / A1) of 0.1 or less between the maximum absorbance A3 of light in the wavelength range of 600 to 700 nm and the maximum absorbance A1 of light in the wavelength range of 400 to 480 nm. It is preferably 0.03 or less, more preferably 0.02 or less.
- Magenta dyes used in the present invention is to be from 0.001 to 0.15 It is preferably 0.005 to 0.10., More preferably 0.01 to 0.05. Further, the magenta color dye, the absorbance A 650 of the light with a wavelength of 650 nm, it is preferable that the ratio between the absorbance A 525 of wavelength 525nm of the light (A 650 / A 525) of 0.2 or less, 0.1 or less Is more preferable, and 0.05 or less is further preferable.
- magenta dye is preferably a ratio between the absorbance A 650 and wavelength 440nm absorbance A 440 of the light of the light with a wavelength of 650nm (A 650 / A 440) of 0.1 or less, 0.03 or less It is more preferably present, and more preferably 0.02 or less.
- the absorbance and maximum absorption wavelength of the magenta color dye are measured by forming a film using a composition containing the magenta color dye and a resin and measuring the spectral characteristics of the film using a spectrophotometer.
- a spectrophotometer Using the magenta color dye as a solvent.
- a dye solution can be prepared by dissolving the dye solution, and the spectral characteristics of the dye solution can be measured by a method using a spectrophotometer.
- the magenta color dye used in the present invention preferably has a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., preferably 0.1 g or more, and more preferably 1 g or more. preferable.
- the magenta color dye used in the present invention preferably contains at least one selected from the group consisting of quinacridone compounds, xanthene compounds, triarylmethane compounds, cyanine compounds, anthraquinone compounds and dipyrromethene compounds, and preferably contains xanthene compounds and cyanine compounds. It is more preferable to contain at least one selected from the group consisting of, and it is further preferable to contain a cyanine compound.
- the cyanine compound is preferably a salt of a cationic cyanine chromophore and a counter anion.
- cationic cyanine chromophore examples include a structure represented by the following formula (Cy1).
- R c1 to R c3 independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group
- ring Z 1 and ring Z 2 each independently represent a heterocycle
- p is. Represents 1 or 2. However, when p is 2, a plurality of R c1 and R c2 may be the same or different.
- the heterocycle represented by ring Z 1 and ring Z 2 may be a monocyclic ring or a condensed ring.
- the heterocycle may be an unsaturated ring or a saturated ring.
- the fused ring may have two or more heteroatoms of the same type or different types (for example, nitrogen atom, oxygen atom, sulfur atom) in the ring.
- heterocycle examples include a nitrogen-containing alicyclic heterocycle such as a pyrrolidine ring, a pyrazoline ring, a morpholin ring, a thiomorpholin ring, a piperidine ring, a piperazine ring, a homopiperazin ring, and a tetrahydropyrimidine ring, a pyridine ring, and a pyrazine ring.
- nitrogen-containing alicyclic heterocycle such as a pyrrolidine ring, a pyrazoline ring, a morpholin ring, a thiomorpholin ring, a piperidine ring, a piperazine ring, a homopiperazin ring, and a tetrahydropyrimidine ring, a pyridine ring, and a pyrazine ring.
- P represents 1 or 2, and 1 is preferable.
- Examples of the halogen atom represented by R c1 to R c3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Examples of the hydrocarbon group represented by R c1 to R c3 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.
- the term "alicyclic hydrocarbon group" as used herein is a concept excluding an aliphatic hydrocarbon group having no cyclic structure.
- the aliphatic hydrocarbon group may be saturated or unsaturated, and examples thereof include a linear or branched alkyl group, an alkenyl group, and an alkynyl group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 12.
- Specific examples of the linear or branched alkyl group include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, hexyl group, heptyl group and octyl.
- nonyl group decyl group, undecyl group, 1-methyldecyl group, dodecyl group, 1-methylundecyl group, 1-ethyldecyl group, tridecyl group, tetradecyl group, tert-dodecyl group, pentadecyl group, 1-heptyloctyl group , Hexadecyl group, octadecyl group and the like.
- linear or branched alkenyl group examples include ethenyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 1,3-butadienyl group, 1-pentenyl group, 2- Examples thereof include a penthenyl group, a 1-hexenyl group, a 2-ethyl-2-butenyl group, a 2-octenyl group, a (4-ethenyl) -5-hexenyl group, a 2-decenyl group and the like.
- linear or branched alkynyl group examples include ethynyl group, 1-propynyl group, 1-butynyl group, 1-pentynyl group, 3-pentynyl group, 1-hexynyl group and 2-ethyl-2-butynyl group.
- examples thereof include a group, a 2-octynyl group, a (4-ethynyl) -5-hexynyl group, a 2-decynyl group and the like.
- alicyclic hydrocarbon group examples include a cyclic alkyl group (cycloalkyl group), a cyclic alkenyl group (cycloalkenyl group), a condensed polycyclic hydrocarbon group, a bridging ring hydrocarbon group, and a spirohydrocarbon group. Cyclic terpene hydrocarbon groups and the like can be mentioned.
- the alicyclic hydrocarbon group preferably has 3 to 30, more preferably 3 to 20, and even more preferably 3 to 12.
- cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a t-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.
- cycloalkenyl group examples include 1 -Includes cyclohexenyl groups and the like.
- condensed polycyclic hydrocarbon group examples include a tricyclodecanyl group, a decahydro-2-naphthyl group, an adamantyl group and the like.
- bridging ring hydrocarbon group examples include tricyclo [5.2.1.0 2,6 ] decane-8-yl group, pentacyclopentadecanyl group, isobornyl group, dicyclopentenyl group, and tricyclopentenyl.
- the group etc. can be mentioned.
- Specific examples of the spiro hydrocarbon group include a spiro [3,4] heptane, a monovalent group obtained by removing one hydrogen atom from a spiro [3,4] octane, and the like.
- Specific examples of the cyclic terpene hydrocarbon group include a monovalent group obtained by removing one hydrogen atom from p-menthane, thujone, karan and the like.
- aromatic hydrocarbon group examples include an aryl group and the like.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 10.
- R c1 to R c3 are hydrogen atoms.
- the heterocycle represented by rings Z 1 and Z 2 and the hydrocarbon group represented by R c1 to R c3 may have a substituent.
- Substituents include halogen atom, hydroxy group, cyano group, formyl group, carboxyl group, nitro group, amino group, dialkylamino group, diarylamino group, alkoxy group, aryloxy group, alkoxycarbonyl group, alkylthio group and arylthio group.
- These substituents may further have a substituent.
- An organic group having a crosslinkable group indicates a group composed of an atomic group containing a crosslinkable group, containing a carbon atom-hydrogen atom bond as a whole, and optionally containing an atom other than carbon.
- a group represented by the following formula (P-1) can be mentioned.
- P-1 a group represented by the following formula
- L p1 represents a single bond or a linking group
- R p1 represents a crosslinkable group.
- Examples of the linking group represented by L p1 include an alkylene group, an arylene group, -O-, -CO-, -NH-, -COO-, -OCO-, -CONH-, -NHCO- and a group formed by combining these. Can be mentioned.
- Examples of the crosslinkable group represented by R p1 include a (meth) acryloyl group, a vinyl group, an epoxy group, and an isocyanate group.
- the structure represented by the formula (Cy1) is preferably a structure represented by the following formula (Cy2).
- R c1 to R c3 independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group
- ring Z 1A and ring Z 2A each independently represent an aromatic hydrocarbon ring
- T 1 and T 2 independently represent -O-, -S- or -CR c6 R c7-
- R c4 to R c7 independently represent hydrocarbon groups, respectively.
- an aromatic hydrocarbon ring represented by the ring Z 1A and the ring Z 2A an aromatic hydrocarbon ring having 6 to 20 carbon atoms is preferable, an aromatic hydrocarbon ring having 6 to 10 carbon atoms is more preferable, and a benzene ring is particularly preferable. preferable.
- R c1 ⁇ R c3 of formula (Cy2) has the same meaning as R c1 ⁇ R c3 of formula (Cy1), and preferred ranges are also the same.
- T 1 and T 2 of the formula (Cy2) -O- and -CR c6 R c7- are preferable.
- the hydrocarbon group represented by R c6 and R c7 an aliphatic hydrocarbon group is preferable, a linear or branched alkyl group is more preferable, a straight chain or branched alkyl group having 1 to 8 carbon atoms is further preferable, and carbon. Linear or branched alkyl groups of numbers 1 to 4 are even more preferred, and methyl or ethyl groups are particularly preferred.
- Examples of the hydrocarbon group represented by R c4 and R c5 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. Specific examples include those similar to those exemplified as the hydrocarbon groups represented by R c1 to R c3 . Among them, as the hydrocarbon group represented by R c4 and R c5 , an aliphatic hydrocarbon group is preferable, a linear or branched alkyl group is more preferable, and a linear or branched alkyl group having 1 to 12 carbon atoms is further preferable. , A linear or branched alkyl group having 1 to 8 carbon atoms is even more preferable, and a linear or branched alkyl group having 1 to 6 carbon atoms is particularly preferable.
- the aromatic hydrocarbon ring represented by rings Z 1A and Z 2A and the hydrocarbon group represented by R c4 to R c5 may have a substituent.
- substituents include the above-mentioned substituents.
- cationic cyanine chromophore examples include a chromophore having the structure shown in Examples described later, and a chromophore having the structure described in paragraphs 0030 to 0033 of JP-A-2017-066377, JP-A-2015-232642. Examples thereof include chromophores having the structures described in paragraphs 0038 to 0047 of the publication.
- halide anions fluorine anion, chlorine anion, bromine anion, iodine anion), perhalogen acid anion (ClO 4 -, FO 4 - , BrO 4 -, IO 4 - , etc.), thiocyanate anions ( SCN - etc.), Sulfate anion, heteropolyacid, carboxylic acid anion, sulfonic acid anion, fatty acid anion, fluorine group-containing boron anion, fluorine group-containing phosphorus anion, imide anion, methide anion, resin having anionic group in the side chain, etc. Can be mentioned.
- magenta dye used in the present invention is a salt of a cationic cyanine chromophore and an imide anion, and a cationic cyanine chromophore and an anion, because a cured film having better heat resistance can be easily obtained. It is preferably a salt with a resin having a sex group in the side chain, and more preferably a salt with a cationic cyanine chromophore and an imide anion.
- imide anion examples include an anion represented by the formula (AN-1) and an anion represented by the formula (AN-2), and an anion represented by the formula (AN-2) is preferable. ..
- Equation (AN-1) In formula (AN-1), X 1 and X 2 independently represent a halogen atom, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a heterocyclic group, respectively. X 1 and X 2 may be combined to form a ring.
- Examples of the halogen atom represented by X 1 and X 2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
- Examples of the aliphatic hydrocarbon group represented by X 1 and X 2 include a linear or branched alkyl group, an alkenyl group, and an alkynyl group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 12.
- Specific examples of the linear or branched alkyl group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, tridecyl group and pentadecyl group.
- Examples thereof include a group, a hexadecyl group, an octadecyl group, a nonadecil group, a pentadecyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group and an isooctyl group.
- Examples of the alicyclic hydrocarbon group represented by X 1 and X 2 include a cyclic alkyl group (cycloalkyl group), a cyclic alkenyl group (cycloalkenyl group), a condensed polycyclic hydrocarbon group, and a bridging ring hydrocarbon group. Examples thereof include a spiro hydrocarbon group and a cyclic terpene hydrocarbon group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 12.
- the alicyclic hydrocarbon group examples include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group and the like.
- the aromatic hydrocarbon group represented by X 1 and X 2 examples include an aryl group and the like.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 10.
- Specific examples of the aromatic hydrocarbon group include a phenyl group, a biphenylyl group, a naphthyl group and the like.
- the heterocyclic group represented by X 1 and X 2 may be a monocyclic ring or a condensed ring.
- the heterocycle may be an unsaturated ring or a saturated ring.
- the fused ring may have two or more heteroatoms of the same type or different types (for example, nitrogen atom, oxygen atom, sulfur atom) in the ring.
- heterocycle examples include an indole ring group, a benzoindole ring group, an indolenin ring group, a benzoindolenin ring group, an oxazole ring group, a benzoxazole ring group, a thiazole ring group, a benzothiazole ring group, and a benzimidazole ring group.
- Quinoline ring group and the like Quinoline ring group and the like.
- the aliphatic hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group represented by X 1 and X 2 may have a substituent.
- Substituents include aliphatic groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group and tert-pentyl group.
- Hydrocarbon group such as (meth) acryloyl group, vinylaryl group, vinyloxy group, allyl group, epoxy group; phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xsilyl group, mesityl
- Aromatic hydrocarbon groups such as groups, o-cumenyl groups, m-cumenyl groups, p-cumenyl groups; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert- Alkoxy groups such as butoxy group and pentyloxy group; aryloxy groups such as phenoxy group; aralkyloxy groups such as benzyloxy group; ester bonds such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group and benzoyloxy group.
- methyl sulfamoyl group dimethyl sulfamoyl group, ethyl sulfamoyl group, diethyl sulfamoyl group, n-propyl sulfamoyl group, di-n-propyl sulfamoyl group, isopropyl sulfamoyl Alkyl sulfamoyl groups such as groups, diisopropyl sulfamoyl groups, n-butyl sulfamoyl groups, di-n-butyl sulfamoyl groups; methyl sulfonyl groups, ethyl sulfonyl groups, propyl sulfonyl groups, isopropyl sulfonyl groups, n -Alkylsulfonyl groups such as butylsulfonyl group, isobutylsulf
- X 1 may have an aliphatic hydrocarbon group which may have a substituent, an alicyclic hydrocarbon group which may have a substituent, or an aromatic which may have a substituent. It is preferably a group hydrocarbon group. Further, X 2 is preferably an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent.
- an alkyl group having 1 to 20 carbon atoms substituted with a fluorine atom or an aromatic hydrocarbon group is preferable, and an alkyl group having 1 to 20 carbon atoms substituted with a fluorine atom is preferable. More preferably, a trifluoromethyl group is particularly preferable.
- an aromatic hydrocarbon group substituted with a fluorine atom is preferable, and a p-fluorophenyl group or a pentafluorophenyl group is more preferable.
- anion represented by the formula (AN-1) include anions having the structures described in paragraphs 0074 to 0077 of JP2015-232642A.
- Y 1 represents a group having a polymerizable group.
- Y 2 represents a halogen atom, a halogenated hydrocarbon group, or a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom, a halogen-substituted alkylene group, an alkyl group, and an alicyclic hydrocarbon.
- Examples of the halogen atom represented by Y 2 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Examples of the hydrocarbon group forming the skeleton of the halogenated hydrocarbon group represented by Y 2 include (1) an aliphatic hydrocarbon group, (2) an alicyclic hydrocarbon group, and (3) an alicyclic hydrocarbon as a substituent.
- An aliphatic hydrocarbon group having a hydrogen group hereinafter referred to as "aliocyclic hydrocarbon-substituted aliphatic hydrocarbon group"
- aromatic hydrocarbon group aromatic hydrocarbon group
- (5) aliphatic hydrocarbon group as a substituent are used.
- Aromatic hydrocarbon group having (hereinafter, referred to as "aliphatic hydrocarbon substituted aromatic hydrocarbon group"), (6) an aliphatic hydrocarbon group having an aromatic hydrocarbon group as a substituent (hereinafter, “aromatic carbide”) "Hydrogen-substituted aliphatic hydrocarbon group”) and the like can be mentioned.
- the hydrocarbon group forming the skeleton of Y 2 is preferably the following characteristic group from the viewpoint of solubility in an organic solvent. That is, as the (1) aliphatic hydrocarbon group, an alkyl group is preferable, and the number of carbon atoms thereof is preferably 1 to 20, and particularly preferably 1 to 8.
- the alicyclic hydrocarbon group (2) may be a bridging alicyclic hydrocarbon group having 2 to 4 rings.
- an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms and further 3 to 12 carbon atoms is preferable.
- an alicyclic hydrocarbon-substituted aliphatic hydrocarbon group (3) an alicyclic saturated hydrocarbon-substituted alkyl group is preferable, and the total carbon number thereof is preferably 4 to 20, particularly 6 to 14. Is preferable.
- the aromatic hydrocarbon group (4) an aryl group having 6 to 14 carbon atoms and further 6 to 10 carbon atoms is preferable, and a phenyl group is more preferable.
- an alkyl-substituted phenyl group is preferable, and the total carbon number thereof is preferably 7 to 30, particularly preferably 7 to 20. Specific examples thereof include a tolyl group, a xylyl group, a mesitylene group and the like.
- an aromatic hydrocarbon-substituted aliphatic hydrocarbon group (6) an aralkyl group is preferable, and the total carbon number thereof is preferably 7 to 30, particularly preferably 7 to 20.
- the hydrocarbon groups forming the skeleton of the halogenated hydrocarbon groups include (1) aliphatic hydrocarbon groups, (3) alicyclic hydrocarbon-substituted aliphatic hydrocarbon groups, and (4) aromatic hydrocarbons.
- Groups, (5) aliphatic hydrocarbon-substituted aromatic hydrocarbon groups or (6) aromatic hydrocarbon-substituted aliphatic hydrocarbon groups are preferred, alkyl groups, alicyclic saturated hydrocarbon-substituted alkyl groups, phenyl groups, alkyl-substituted.
- a phenyl group and an aralkyl group are more preferable, and an alkyl group is particularly preferable.
- the halogen atom of the halogenated hydrocarbon group from the viewpoint of the heat resistance of the magenta color dye, a fluorine atom is preferable. That is, the halogenated hydrocarbon group is preferably one in which a part or all of the hydrogen atoms of the hydrocarbon group are substituted with fluorine atoms.
- Y 2 of the formula (AN-2) is a linking group containing an atom other than a carbon atom, a hydrogen atom or a halogen atom, a halogen-substituted alkylene group, an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group and a substituted or substituted group. It may be a group formed by combining a monovalent group selected from an unsubstituted aryl group.
- Examples of the linking group containing an atom other than a carbon atom, a hydrogen atom and a halogen atom include -O-, -S-, -CO-, -COO-, -CONH-, and -SO 2- .
- halogen-substituted alkylene group examples include a group in which a part or all of the hydrogen atom of the alkylene group is substituted with a halogen atom.
- the alkylene group preferably has 1 to 10 carbon atoms.
- a fluorine atom is preferable from the viewpoint of heat resistance.
- the above-mentioned alkyl group preferably has 1 to 20 carbon atoms, and more preferably 1 to 8 carbon atoms.
- the alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.
- heteroaryl group a group composed of a 5- to 10-membered aromatic heterocycle containing one or more heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom is preferable. Specific examples thereof include a frill group, a thienyl group, a pyrrolyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a carbazolyl group and the like.
- aryl group an aryl group having 6 to 14 carbon atoms and further 6 to 10 carbon atoms is preferable, and a phenyl group and a naphthyl group are particularly preferable.
- substituent of the aryl group examples include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen atom or a trifluoromethyl group.
- the position and number of substituents are arbitrary, and when there are two or more substituents, these substituents may be the same or different.
- Y 2 of the formula (AN-2) is a halogenated hydrocarbon group, a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom, a halogen-substituted alkylene group, and an alkyl group.
- a group composed of a combination of an alicyclic hydrocarbon group, a heteroaryl group and a monovalent group selected from a substituted or unsubstituted aryl group is preferable, and is represented by the following formula (Y2-1) or (Y2-2). Is more preferable, and the group represented by the following formula (Y2-1) is further preferable.
- R y1 is a hydrogen atom, a fluorine atom, an alkyl group, an alkyl fluoride group, an alicyclic hydrocarbon group, an alkoxy group, an alkoxy fluoride group, R y20 COOR y21 -or R y22 COOR.
- Represents y23 CFH- R y20 and R y22 each independently represent an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group.
- R y21 and R y23 each independently represent an alkylene group.
- n represents an integer greater than or equal to 1 and represents * Represents a bond.
- R y2 to R y6 independently represent a hydrogen atom, a fluorine atom, a hydroxy group, an alkyl group, an alkyl fluoride group or an alkoxy group, and * represents a bond. However, at least one of R y2 to R y6 is a fluorine atom or an alkyl fluoride group.
- Y 1 of the formula (AN-2) represents a group having a polymerizable group.
- the group having a polymerizable group represented by Y 1 is preferably a group represented by the formula (Y1-1).
- L 1 represents a single bond or a divalent linking group
- Q 1 represents a polymerizable group
- * represents a bond
- Ra represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
- Examples of the divalent hydrocarbon group include an alkylene group and an arylene group. In the divalent hydrocarbon group, at least a part of hydrogen atoms may be substituted with halogen atoms (preferably fluorine atoms).
- the divalent linking group represented by L 1 is an alkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; an arylene alkylene group having 7 to 20 carbon atoms; an alkylene group having 1 to 10 carbon atoms and a carbon number of carbon atoms.
- a group consisting of a combination of at least one selected from 6 to 20 arylene groups and at least one selected from -O-, -S-, -COO-, -CONR a- and -SO 2- is preferable.
- Examples of the polymerizable group represented by Q 1 include an ethylenically unsaturated group.
- the ethylenically unsaturated group include a vinyl group, an allyl group, a metharyl group, a (meth) acryloyl group and a styrene group, with (meth) acryloyl group and styrene group being preferable, and (meth) acryloyl group being more preferable.
- the group having a polymerizable group represented by Y 1 of the formula (AN-2) is preferably a group represented by the formula (Y1-2) from the viewpoint of heat resistance.
- L 2 represents a single bond or a divalent linking group
- Q 1 represents a polymerizable group
- * represents a bond
- Q 1 Formula (Y1-2) has the same meaning as to Q 1 Formula (Y1-1), and preferred ranges are also the same.
- Examples of the divalent linking group represented by L 2 a divalent hydrocarbon group; a divalent hydrocarbon group and -NR a -, - SO -, - SO 2 -, - CO -, - O -, - COO Examples thereof include a group formed by combining a group selected from-, -OCO-, -CONR a- , -NR a CO- and -S-.
- the divalent linking group represented by L 2 is selected from an alkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; an alkylene group having 1 to 10 carbon atoms and an arylene group having 6 to 20 carbon atoms. A group consisting of a combination of at least one type and —O— is preferable.
- anion represented by the formula (AN-2) include an anion having the structure described in Examples described later, an anion described in paragraph No. 0142 of JP-A-2017-066377, and the like.
- resin having an anionic group in the side chain examples include a resin having a repeating unit represented by the following formula (AN-10). Equation (AN-10)
- R 100 represents a hydrogen atom or an alkyl group.
- L 10 represents an alkylene group, an arylene group, -CONH-R 101- , or -COO-R 101- , and R 101 represents an alkylene group.
- P 10 represents an anionic group.
- the number of carbon atoms of the alkyl group represented by R 100 is preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 4.
- the alkyl group is preferably a straight chain alkyl group.
- the alkyl group represented by R 100 may have a substituent. Examples of the substituent include a hydroxy group and an alkoxy group.
- the R 100 is preferably a hydrogen atom or a methyl group.
- the anionic group P 10 represents, -SO 3 -, -COO - are exemplified, -SO 3 - it is preferable.
- L 10 is, -CONH-R 101 -, - is preferably, -COO-R 101 - - COO -R 101 is more preferable.
- the resin having an anionic group in the side chain may contain other repeating units in addition to the repeating unit represented by the formula (AN-10).
- Examples of other repeating units include repeating units having a polymerizable group.
- the weight average molecular weight of the resin having an anionic group in the side chain is preferably 1000 to 500,000, and more preferably 3000 to 15,000. Details of the resin having an anionic group in the side chain are described in paragraphs 0101 to 0144 of JP2015-232642A, and the contents thereof are incorporated in the present specification.
- the coloring composition of the present invention preferably contains 1 to 50 parts by mass of magenta dye with respect to 100 parts by mass of pigment A.
- the upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
- the lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more.
- the content of the magenta color dye is preferably 0.4 to 30% by mass in the total solid content of the coloring composition.
- the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and further preferably 15% by mass or less.
- the lower limit is preferably 1% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more.
- the total content of the pigment A and the magenta color dye is preferably 30 to 85% by mass in the total solid content of the coloring composition.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and further preferably 70% by mass or less.
- the lower limit is preferably 35% by mass or more, more preferably 40% by mass or more, and further preferably 45% by mass or more.
- the coloring composition of the present invention can contain a coloring agent other than the diketopyrrolopyrrole pigment and the magenta color dye (hereinafter, also referred to as other coloring agents).
- the other colorant may be a pigment or a dye. Pigments and dyes may be used in combination.
- Other colorants used in the present invention preferably contain pigments.
- the pigment may be an organic pigment or an inorganic pigment.
- an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can be used. Hue design can be facilitated by replacing inorganic pigments and organic-inorganic pigments with organic chromophores.
- the content of the pigment in the other colorants is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 80% by mass or more, and 90% by mass or more. Is particularly preferred.
- the other colorant may be only a pigment.
- the coloring composition of the present invention preferably contains a yellow colorant as another colorant, and more preferably contains a yellow pigment. According to this aspect, it is easy to form a cured film having spectral characteristics suitable for red pixels. Further, when a yellow pigment is used as another colorant, the dispersibility of the pigment A can be improved.
- yellow colorant examples include azo compounds, quinophthalone compounds, isoindoline compounds, isoindoline compounds and anthraquinone compounds, with isoindoline compounds, azo compounds and quinophthalone compounds being preferred, isoindoline compounds and azo compounds being more preferred. Isoindoline compounds are particularly preferred because they tend to form cured films with more suitable spectral properties for red.
- yellow colorants include Color Index (CI) Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24, 31, 32, 34, 35, 35: 1,36, 36: 1,37,37: 1,40,42,43,53,55,60,61,62,63,65,73,74,77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171 172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215,228,231,232
- the compounds described in JP-A-2017-201003 the compounds described in JP-A-2017-197719, and paragraph numbers 0011 to 0062,0137 of JP-A-2017-171912.
- Compounds described in JP-A-0276 compounds described in JP-A-2017-171913, paragraph numbers 0010 to 0062, 0138-0295, paragraph numbers 0011-0062, 0139-0190 of JP-A-2017-171914.
- JP-A-2018-155881 The quinophthalone compound described in JP-A-2018-11757, the quinophthalone compound described in JP-A-2018-040835, and the quinophthalone compound described in JP-A-2017-197640.
- the quinophthalone compound described in Japanese Patent Application Laid-Open No. 2019-008014, the quinophthalone compound described in JP-A-2019-008014, and the compound represented by the following formula (QP1) can also be used.
- X 1 to X 16 independently represent a hydrogen atom or a halogen atom, and Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by the formula (QP1) include the compounds described in paragraph No. 0016 of Japanese Patent No. 6443711.
- C.I. I. Pigment Yellow 138, C.I. I. Pigment Yellow 139, C.I. I. Pigment Yellow 150 and C.I. I. Pigment Yellow 185 is more preferably one or more selected from C.I. I. Pigment Yellow 139 and C.I. I. More preferably, it is one or more selected from Pigment Yellow 150, and C.I. I. Pigment Yellow 139 is particularly preferred.
- colorants other than the yellow colorant include the following.
- a halogenated zinc phthalocyanine pigment having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. Can also be used. Specific examples thereof include the compounds described in WO 2015/118720.
- a green pigment a compound described in Chinese Patent Application No. 106909027, a phthalocyanine compound having a phosphate ester described in International Publication No. 2012/10395 as a ligand, and Japanese Patent Application Laid-Open No. 2019-008014. Phthalocyanine compounds and phthalocyanine compounds described in JP-A-2018-180023 can be used.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraphs 0047 of JP2011-157478A.
- dyes other than the magenta color dyes there are no particular restrictions on the dyes other than the magenta color dyes, and known dyes can be used.
- the thiazole compound described in JP2012-158649A, the azo compound described in JP2011-184493, and the azo compound described in JP2011-145540 may be used. it can.
- the dye multimer is preferably a dye used by dissolving it in a solvent, but the dye multimer may form particles, and when the dye multimer is a particle, it is usually dispersed in a solvent. Used.
- the dye multimer in the particle state can be obtained by, for example, emulsion polymerization, and specific examples thereof include the compounds and production methods described in JP-A-2015-214682.
- the dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less.
- the plurality of dye structures contained in one molecule may have the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2000 to 50,000.
- the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
- the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
- compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742 and the like can also be used.
- the content of the other colorant is preferably 40 parts by mass or less with respect to 100 parts by mass of the pigment A.
- the lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more.
- the upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the content of the yellow colorant is preferably 40 parts by mass or less with respect to 100 parts by mass of the pigment A.
- the lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more.
- the upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the content of the yellow colorant is preferably 100 parts by mass or less with respect to 100 parts by mass of the magenta dye.
- the lower limit is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and further preferably 15 parts by mass or more.
- the upper limit is preferably 80 parts by mass or less, and more preferably 60 parts by mass or less.
- the content of the yellow colorant is preferably 50 parts by mass or less with respect to 100 parts by mass in total of the pigment A and the magenta color dye.
- the lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
- the total content of the pigment A, the magenta dye, and the other colorants is preferably 40 to 90% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 45% by mass or more, and more preferably 50% by mass or more.
- the upper limit is preferably 85% by mass or less, and more preferably 80% by mass or less.
- the total content of the pigment A, the magenta dye, and the yellow colorant is preferably 40 to 90% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 45% by mass or more, and more preferably 50% by mass or more.
- the upper limit is preferably 85% by mass or less, and more preferably 80% by mass or less.
- the coloring composition of the present invention contains a compound having a curable group.
- the reaction mechanism when the compound having a curable group is cured is not particularly limited. Examples thereof include radical polymerization reaction, cationic polymerization reaction, polycondensation reaction, nucleophilic addition reaction, and cross-linking reaction by substitution reaction.
- the compound having a curable group is preferably a compound that is cured by a radical polymerization reaction. Examples of the curable group include an ethylenically unsaturated group and an epoxy group.
- Examples of the ethylenically unsaturated group include a vinyl group, a vinyloxy group, an allyl group, a metallicyl group, a (meth) acryloyl group, a styrene group, a cinnamoyl group and a maleimide group, and a (meth) acryloyl group, a styrene group and a maleimide group.
- a (meth) acryloyl group is more preferred.
- the compound having a curable group may be a monomer or a resin such as a polymer.
- a monomer-type curable compound and a resin-type curable compound can also be used in combination.
- the compound having an ethylenically unsaturated group used as the curable compound may be a monomer or a resin. It is preferable to contain a resin type compound because it is easy to form a cured film having excellent heat resistance.
- the compound having an ethylenically unsaturated group is also referred to as a polymerizable compound.
- a monomer having an ethylenically unsaturated group is also referred to as a polymerizable monomer.
- a resin having an ethylenically unsaturated group is also referred to as a polymerizable resin.
- the molecular weight of the polymerizable monomer is preferably less than 3000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is preferably 100 or more, more preferably 150 or more, and even more preferably 250 or more.
- the polymerizable monomer is preferably a compound containing 3 or more ethylenically unsaturated groups, more preferably a compound containing 3 to 15 ethylenically unsaturated groups, and 3 to 6 ethylenically unsaturated groups. It is more preferable that the compound contains two compounds.
- the polymerizable monomer is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
- Specific examples of the polymerizable monomer include paragraph numbers 0905 to 0108 of JP2009-288705A, paragraph numbers 0227 of JP2013-209760A, and paragraph numbers 0254 to 0257 of JP2008-292970.
- the polymerizable monomers are dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.) and dipentaerythritol tetraacrylate (commercially available KAYARAD D-320; Nippon Kayaku Co., Ltd.).
- Dipentaerythritol penta (meth) acrylate (commercially available KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (commercially available KAYARAD DPHA; Japanese chemical (manufactured) NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and compounds having a structure in which these (meth) acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues.
- SR454 and SR499 commercially available from Sartmer
- NK ester A-TMMT manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- KAYARAD RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- DPCA-20 manufactured by Nippon Kayaku Co., Ltd.
- trimethylolpropane tri (meth) acrylate trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanurate ethyleneoxy-modified tri (meth) acrylate.
- trifunctional (meth) acrylate compound such as pentaerythritol trimethylolpropane (meth) acrylate.
- commercially available trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305.
- M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
- a compound having an acid group can also be used.
- the colored composition layer in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
- the acid group include a carboxyl group, a sulfo group, a phosphoric acid group and the like, and a carboxyl group is preferable.
- the polymerizable monomer having an acid group include succinic acid-modified dipentaerythritol penta (meth) acrylate.
- Examples of commercially available products of the polymerizable monomer having an acid group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the preferable acid value of the polymerizable monomer having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
- the acid value of the polymerizable monomer is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.
- a compound having a caprolactone structure can also be used.
- Polymerizable monomers having a caprolactone structure are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series, and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.
- a compound having an alkyleneoxy group can also be used.
- the polymerizable monomer having an alkyleneoxy group is preferably a compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a compound having an ethyleneoxy group, and having 4 to 20 ethyleneoxy groups. More preferably, it is a 3-6 functional (meth) acrylate compound.
- Commercially available products of the polymerizable monomer having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer, and a trifunctional (meth) having three isobutyleneoxy groups. Examples thereof include KAYARAD TPA-330, which is an acrylate.
- the polymerizable monomer it is also preferable to use a compound that does not substantially contain an environmentally regulated substance such as toluene.
- an environmentally regulated substance such as toluene.
- Commercially available products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12LT (manufactured by Nippon Kayaku Co., Ltd.) and the like.
- Examples of the polymerizable monomer include urethane acrylates described in Japanese Patent Application Laid-Open No. 48-041708, Japanese Patent Application Laid-Open No. 51-0371993, Japanese Patent Application Laid-Open No. 02-032293, and Japanese Patent Application Laid-Open No. 02-016765.
- a compound having an amino structure or a sulfide structure in the molecule described in Kaisho 63-260909 and Japanese Patent Application Laid-Open No. 01-105238.
- the polymerizable monomer UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600. , T-600, AI-600, LINK-202UA (Kyoeisha Chemical Co., Ltd.) and other commercially available products can also be used.
- the weight average molecular weight of the polymerizable resin is preferably 3000 or more, more preferably 5000 or more, further preferably 7000 or more, and particularly preferably 10000 or more.
- the weight average molecular weight of the polymerizable resin is preferably 50,000 or less, more preferably 40,000 or less, and even more preferably 30,000 or less.
- the upper limit is more preferably 4.0 mmol / g or less, further preferably 3.0 mmol / g or less, further preferably 2.0 mmol / g or less, and 1.0 mmol / g or less. It is particularly preferable to have.
- the lower limit is preferably 0.1 mmol / g or more, and more preferably 0.2 mmol / g or more.
- HPLC high performance liquid chromatography
- the polymerizable resin preferably contains a repeating unit having an ethylenically unsaturated group in the side chain, and more preferably contains a repeating unit represented by the following formula (A-1-1). Further, the polymerizable resin preferably contains 10 mol% or more of the repeating units having an ethylenically unsaturated group in the side chain in all the repeating units of the polymerizable resin, and more preferably 10 to 80 mol%. , 20-70 mol% is more preferable.
- X 1 represents the main chain of the repeating unit
- L 1 represents a single bond or a divalent linking group
- Y 1 represents an ethylenically unsaturated group.
- the main chain of the repeating unit represented by X 1 is not particularly limited. There is no particular limitation as long as it is a linking group formed from a known polymerizable monomer.
- poly (meth) acrylic linking groups polyalkyleneimine-based linking groups, polyester-based linking groups, polyurethane-based linking groups, polyurea-based linking groups, polyamide-based linking groups, polyether-based linking groups, polystyrene-based linking groups, etc.
- poly (meth) acrylic-based linking groups and polyalkyleneimine-based linking groups are preferable, and poly (meth) acrylic-based linking groups are more preferable.
- the divalent linking group represented by L 1 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an alkyleneoxy group (preferably an alkylene group having 1 to 12 carbon atoms).
- Oxy group oxyalkylenecarbonyl group (preferably oxyalkylenecarbonyl group having 1 to 12 carbon atoms), arylene group (preferably arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2- , -CO-, -O-, -COO-, -OCO-, -S- and groups consisting of a combination of two or more of these.
- the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylenecarbonyl group may be linear, branched, or cyclic, and are preferably linear or branched. Further, the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylenecarbonyl group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxy group and an alkoxy group, and a hydroxy group is preferable from the viewpoint of production suitability.
- examples of the ethylenically unsaturated group represented by Y 1 include a vinyl group, a vinyloxy group, an allyl group, a metalyl group, a (meth) acryloyl group, a styrene group, a cinnamoyl group and a maleimide group.
- the (meth) acryloyl group, the styrene group, and the maleimide group are preferable, the (meth) acryloyl group is more preferable, and the acryloyl group is particularly preferable.
- repeating unit represented by the formula (A-1-1) include a repeating unit represented by the following formula (A-1-1a) and a repeating unit represented by the following formula (A-1-1b). The unit etc. can be mentioned.
- R a1 to R a3 independently represent a hydrogen atom or an alkyl group
- Q 1a is -CO-, -COO-, -OCO-, -CONH- or phenylene.
- L 1 represents a single bond or a divalent linking group
- Y 1 represents an ethylenically unsaturated group.
- the number of carbon atoms of the alkyl group represented by R a1 to Ra3 is preferably 1 to 10, more preferably 1 to 3, and even more preferably 1.
- Q 1a is preferably -COO- or -CONH-, and more preferably -COO-.
- R a10 and R a11 are each independently a hydrogen atom or an alkyl group, m1 represents an integer of 1 ⁇ 5, L 1 represents a single bond or a divalent linking of It represents a group and Y 1 represents an ethylenically unsaturated group.
- the number of carbon atoms of the alkyl group represented by R a10 and R a11 is preferably 1 to 10, and more preferably 1 to 3.
- the polymerizable resin preferably further contains a repeating unit having a graft chain.
- the polymerizable resin contains a repeating unit having a graft chain, it is possible to more effectively suppress the aggregation of the pigment A due to steric hindrance caused by the graft chain.
- the polymerizable resin can be polymerized in the vicinity of the pigment A to firmly hold the pigment A in the film, and the heat diffusion of the pigment A due to heating can be more effectively suppressed. Therefore, it is possible to form a cured film having more excellent heat resistance.
- the polymerizable resin preferably contains 1.0 to 60 mol%, more preferably 1.5 to 50 mol%, of the repeating units having a graft chain in all the repeating units of the polymerizable resin.
- a polymerizable resin containing a repeating unit having a graft chain is preferably used as a dispersant.
- the graft chain means a polymer chain that branches and extends from the main chain of a repeating unit.
- the length of the graft chain is not particularly limited, but the longer the graft chain, the higher the steric repulsion effect, and the dispersibility of the pigment A or the like can be improved.
- the graft chain preferably has 40 to 10000 atoms excluding hydrogen atoms, more preferably 50 to 2000 atoms excluding hydrogen atoms, and 60 to 60 to 2000 atoms excluding hydrogen atoms. It is more preferably 500.
- the graft chain preferably contains at least one structural repeating unit selected from polyester repeating units, polyether repeating units, poly (meth) acrylic repeating units, polyurethane repeating units, polyurea repeating units and polyamide repeating units, preferably polyester. It is more preferable to include a repeating unit of at least one structure selected from a repeating unit, a polyether repeating unit and a poly (meth) acrylic repeating unit, and even more preferably to include a polyester repeating unit.
- the polyester repeating unit include repeating units having a structure represented by the following formula (G-1), formula (G-4) or formula (G-5).
- the polyether repeating unit a repeating unit having a structure represented by the following formula (G-2) can be mentioned.
- the poly (meth) acrylic repeating unit a repeating unit having a structure represented by the following formula (G-3) can be mentioned.
- RG1 and RG2 each represent an alkylene group. It is not particularly restricted but includes alkylene groups represented by R G1 and R G2, preferably a linear or branched alkylene group of 1 to 20 carbon atoms, having 2 to 16 carbon atoms linear or branched alkylene A group is more preferable, and a linear or branched alkylene group having 3 to 12 carbon atoms is further preferable.
- RG3 represents a hydrogen atom or a methyl group.
- Q G1 represents -O- or -NH-
- LG 1 represents a single bond or a divalent linking group.
- the divalent linking group includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), and an oxyalkylenecarbonyl group (preferably 1 to 12 carbon atoms).
- alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- alkyleneoxy group preferably an alkyleneoxy group having 1 to 12 carbon atoms
- an oxyalkylenecarbonyl group preferably 1 to 12 carbon atoms.
- arylene groups preferably arylene groups with 6 to 20 carbon atoms
- RG4 represents a hydrogen atom or a substituent.
- substituents examples include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituents include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group or an alkoxy group having 5 to 24 carbon atoms is preferable, from the viewpoint of improving the dispersibility of the coloring material or the like.
- the alkyl group and the alkoxy group may be linear, branched, or cyclic, and are preferably linear or branched.
- the graft chain has a structure represented by the following formula (G-1a), formula (G-2a), formula (G-3a), formula (G-4a) or formula (G-5a). It is preferable to have.
- R G1 and R G2 each represent an alkylene group
- R G3 represents a hydrogen atom or a methyl group
- Q G1 represents -O- or -NH-
- L G1 represents a single bond or It represents a divalent linking group
- R G4 represents a hydrogen atom or a substituent
- W 100 represents a hydrogen atom or a substituent.
- n1 to n5 each independently represent an integer of 2 or more.
- Q G1 , L G1 , Formula (G1) ⁇ (G-5 ) has the same meaning as R G1 ⁇ R G4, Q G1 , L G1 described in, the preferred range is also the same is there.
- W 100 is preferably a substituent.
- the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group or an alkoxy group having 5 to 24 carbon atoms is preferable, from the viewpoint of improving the dispersibility of the coloring material or the like.
- the alkyl group and the alkoxy group may be linear, branched, or cyclic, and are preferably linear or branched.
- n1 to n5 are preferably integers of 2 to 100, more preferably integers of 2 to 80, and even more preferably integers of 8 to 60.
- R G1 each other in each repeating unit in the case of n1 is 2 or more, may be the same or may be different.
- the arrangement of each repeating unit is not particularly limited and may be random, alternating, or block. The same applies to the formulas (G-2a) to (G-5a).
- repeating unit having a graft chain examples include a repeating unit represented by the following formula (A-1-2).
- X 2 represents the main chain of the repeating unit
- L 2 represents a single bond or a divalent linking group
- W 1 represents a graft chain.
- the divalent linking group represented by L 2 in the formula (A-1-2) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an arylene group (preferably an arylene group having 6 to 20 carbon atoms).
- graft chain represented by W 1 in the formula (A-1-2) examples include the above-mentioned graft chain.
- repeating unit represented by the formula (A-1-2) include the repeating unit represented by the following formula (A-1-2a) and the repeating unit represented by the following formula (A-1-2b). The unit etc. can be mentioned.
- R b1 to R b3 independently represent a hydrogen atom or an alkyl group
- Q b1 is -CO-, -COO-, -OCO-, -CONH- or phenylene.
- L 2 represents a single bond or a divalent linking group
- W 1 represents a graft chain.
- the alkyl group represented by R b1 to R b3 preferably has 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1.
- Q b1 is preferably -COO- or -CONH-, and more preferably -COO-.
- R b10 and R b11 independently represent a hydrogen atom or an alkyl group
- m2 represents an integer of 1 to 5
- L 2 is a single bond or a divalent link.
- W 1 represents a graft chain.
- the number of carbon atoms of the alkyl group represented by R b10 and R b11 is preferably 1 to 10, and more preferably 1 to 3.
- the weight average molecular weight (Mw) of the repeating unit having a graft chain is preferably 1000 or more, more preferably 1000 to 10000, and 1000 to 7500. Is more preferable.
- the weight average molecular weight of the repeating unit having a graft chain is a value calculated from the weight average molecular weight of the raw material monomer used for the polymerization of the repeating unit.
- repeating units with graft chains can be formed by polymerizing macromonomers.
- the macromonomer means a polymer compound having a polymerizable group introduced at the polymer terminal.
- the polymerizable resin further contains a repeating unit having an acid group.
- the repeating unit having an acid group include a carboxyl group, a sulfo group, and a phosphoric acid group.
- repeating unit having an acid group examples include a repeating unit represented by the following formula (A-1-3).
- X 3 represents the main chain of the repeating unit
- L 3 represents a single bond or a divalent linking group
- a 1 represents an acid group.
- the main chain of the repeating unit represented by X 3 in the formula (A-1-3) the structure described by X 1 in the formula (A-1-1) can be mentioned, and the preferable range is also the same.
- the divalent linking group represented by L 3 in the formula (A-1-3) an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an alkenylene group (preferably an alkenylene group having 2 to 12 carbon atoms).
- An alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylenecarbonyl group (preferably an oxyalkylenecarbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms).
- the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylenecarbonyl group may be linear, branched, or cyclic, and are preferably linear or branched. Further, the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylenecarbonyl group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxy group and the like. Examples of the acid group represented by A 1 in the formula (A-1-3) include a carboxyl group, a sulfo group, and a phosphoric acid group.
- repeating unit represented by the formula (A-1-3) include the repeating unit represented by the following formula (A-1-3a) and the repeating unit represented by the following formula (A-1-3b). The unit etc. can be mentioned.
- R c1 to R c3 independently represent a hydrogen atom or an alkyl group
- Q c1 is -CO-, -COO-, -OCO-, -CONH- or phenylene.
- L 3 represents a single bond or a divalent linking group
- a 1 represents an acid group.
- the alkyl group represented by R c1 to R c3 preferably has 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1.
- Q c1 is preferably -COO- or -CONH-, more preferably -COO-.
- R c10 and R c11 independently represent a hydrogen atom or an alkyl group
- m3 represents an integer of 1 to 5
- L 3 is a single bond or a divalent link. It represents a group
- a 1 represents an acid group.
- the number of carbon atoms of the alkyl group represented by R c10 and R c11 is preferably 1 to 10, and more preferably 1 to 3.
- the content of the repeating unit having an acid group is preferably 80 mol% or less, preferably 10 to 80 mol%, based on all the repeating units of the polymerizable resin. More preferred.
- the acid value of the polymerizable resin is preferably 20 to 150 mgKOH / g.
- the upper limit is more preferably 100 mgKOH / g or less.
- the lower limit is preferably 30 mgKOH / g or more, and more preferably 35 mgKOH / g or more.
- the polymerizable resin may be referred to as another repeating unit, a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer”. It can include repeating units derived from monomeric components containing).
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms, which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. Specific examples of the compound represented by the formula (ED2) include the compounds described in JP-A-2010-168539.
- ether dimer for example, paragraph No. 0317 of JP2013-029760A can be referred to, and the contents thereof are incorporated in the present specification.
- the ether dimer may be only one type or two or more types.
- a compound represented by the following formula (SP-1) (hereinafter, also referred to as compound (SP-1)) can be used as the polymerizable resin.
- Compound (SP-1) can be preferably used as a dispersant.
- Z 1 represents a (m + n) valence linking group.
- Y 1 and Y 2 independently represent a single bond or a linking group, respectively.
- a 1 represents a group containing a pigment adsorbing portion.
- P 1 represents a polymer chain n represents 1 to 20, m represents 1 to 20, m + n represents 3 to 21, and so on.
- Each of n Y 1 and A 1 may be the same or different,
- the m Y 2 and P 1 may be the same or different, respectively.
- At least one of Z 1 , A 1 and P 1 represents an ethylenically unsaturated group. Includes sex groups.
- Examples of the ethylenically unsaturated group contained in the compound (SP-1) include a vinyl group, a vinyloxy group, an allyl group, a metallicyl group, a (meth) acryloyl group, a styrene group, a cinnamoyl group and a maleimide group, and examples thereof include (meth).
- Acryloyl group, styrene group and maleimide group are preferable, (meth) acryloyl group is more preferable, and acryloyl group is particularly preferable.
- the ethylenically unsaturated group may be contained in any one of Z 1 , A 1 and P 1 , but is preferably contained in P 1 .
- P 1 contains an ethylenically unsaturated group
- P 1 is preferably a polymer chain having a repeating unit containing an ethylenically unsaturated group in the side chain.
- a 1 represents a group containing a pigment adsorbing portion.
- the pigment adsorbing portion includes an organic dye structure, a heterocyclic structure, an acid group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, and an alkoxy.
- Examples thereof include a silyl group, an epoxy group, an isocyanate group and a hydroxy group, and a heterocyclic structure, an acid group, a group having a basic nitrogen atom, a hydrocarbon group having 4 or more carbon atoms and a hydroxy group are preferable, and the dispersibility of the coloring material is high. From the viewpoint, an acid group is more preferable. Examples of the acid group include a carboxyl group, a sulfo group, and a phosphoric acid group, and a carboxyl group is preferable.
- Pigment adsorbing part, in one of A 1, may be contained at least one, may contain two or more.
- a 1 preferably contains 1 to 10 pigment adsorbing portions, and more preferably 1 to 6 pigment adsorbing portions.
- the group containing the pigment adsorbing portion represented by A 1 includes the above-mentioned pigment adsorbing portion, 1 to 200 carbon atoms, 0 to 20 nitrogen atoms, 0 to 100 oxygen atoms, and 1 to 400 atoms. Examples thereof include a group formed by bonding a hydrogen atom of the above and a linking group consisting of 0 to 40 sulfur atoms.
- chain saturated hydrocarbon group having 1 to 10 carbon atoms examples thereof include groups formed by bonding.
- the above-mentioned chain saturated hydrocarbon group, cyclic saturated hydrocarbon group and aromatic hydrocarbon group may further have a substituent.
- the pigment adsorption unit itself can constitute a monovalent group
- the pigment adsorbing portion itself may be A 1.
- the chemical formula of A 1 is preferably 30 to 2000.
- the upper limit is preferably 1000 or less, and more preferably 800 or less.
- the lower limit is preferably 50 or more, and more preferably 100 or more.
- the chemical formula of A 1 is a value calculated from the structural formula.
- Z 1 represents a (m + n) valent linking group.
- the (m + n) -valent linking group includes 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to 20 sulfur atoms. There is a group consisting of.
- Examples of the (m + n) valent linking group include the following structural units or groups formed by combining two or more of the following structural units (may form a ring structure).
- the chemical formula of Z 1 is preferably 20 to 3000.
- the upper limit is preferably 2000 or less, and more preferably 1500 or less.
- the lower limit is preferably 50 or more, and more preferably 100 or more.
- the chemical formula of Z 1 is a value calculated from the structural formula.
- paragraph numbers 0043 to 0055 of JP-A-2014-177613 can be referred to, and the contents thereof are incorporated in the present specification.
- Y 1 and Y 2 independently represent a single bond or a linking group, respectively.
- the linking group include a group consisting of 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to 20 sulfur atoms. Be done. The above-mentioned group may further have the above-mentioned substituent.
- the linking group represented by Y 1 and Y 2 include a group composed of the following structural units or a combination of two or more of the following structural units.
- P 1 represents a polymer chain.
- the polymer chain represented by P 1 is at least selected from poly (meth) acrylic repeating units, polyether repeating units, polyester repeating units, polyamide repeating units, polyimide repeating units, polyimine repeating units and polyurethane repeating units in the main chain. It is preferably a polymer chain having one type of repeating unit. Further, the polymer chain represented by P 1 is preferably a polymer chain containing a repeating unit represented by the following formulas (P1-1) to (P1-5).
- RG1 and RG2 each represent an alkylene group.
- the alkylene group represented by R G1 and R G2 preferably a linear or branched alkylene group of 1 to 20 carbon atoms, more preferably a linear or branched alkylene group having 2 to 16 carbon atoms , A linear or branched alkylene group having 3 to 12 carbon atoms is more preferable.
- the alkylene group may have a substituent.
- substituents examples include an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, and ethylenically unsaturated groups.
- RG3 represents a hydrogen atom or a methyl group.
- Q G1 represents -O- or -NH-
- LG 1 represents a single bond or an arylene group
- LG 2 represents a single bond or a divalent linking group.
- Q G1 is preferably —O—.
- LG1 is preferably a single bond.
- Examples of the divalent linking group represented by LG2 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-.
- RG4 represents a hydrogen atom or a substituent.
- substituents examples include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, an ethylenically unsaturated group, an acid group and the like. Can be mentioned.
- the number of repetitions of the repeating units described above is preferably from 3 to 2,000.
- the upper limit is preferably 1500 or less, more preferably 1000 or less.
- the lower limit is preferably 5 or more, and more preferably 7 or more.
- P 1 is preferably a polymer chain having a repeating unit containing an ethylenically unsaturated group in the side chain.
- the ratio of the repeating unit containing an ethylenically unsaturated group in the side chain is preferably 1 mol% or more, more preferably 2 mol% or more, It is more preferably 3 mol% or more.
- the upper limit can be 100 mol%.
- P 1 when P 1 is a polymer chain having a repeating unit containing an ethylenically unsaturated group in the side chain, P 1 contains another repeating unit in addition to the repeating unit containing an ethylenically unsaturated group in the side chain. It is also preferable to include it. Examples of other repeating units include repeating units containing an acid group in the side chain.
- the ratio of the repeating unit containing an acid group in the side chain to all the repeating units constituting P 1 is preferably 50 mol% or less. It is more preferably 2 to 48 mol%, further preferably 4 to 46 mol%.
- the weight average molecular weight of the polymer chain represented by P 1 is preferably 1000 or more, and more preferably 1000 to 10000.
- the upper limit is preferably 9000 or less, more preferably 6000 or less, and even more preferably 3000 or less.
- the lower limit is preferably 1200 or more, and more preferably 1400 or more.
- the weight average molecular weight of P 1 is a value calculated from the weight average molecular weight of the raw material used for introducing the polymer chain.
- a compound having an epoxy group used as a curable compound (hereinafter, also referred to as an epoxy compound)
- a compound having two or more epoxy groups in one molecule is preferably used as a compound having an epoxy group used as a curable compound.
- the upper limit of the number of epoxy groups in the epoxy compound is preferably 100 or less, more preferably 10 or less, and further preferably 5 or less.
- the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 1000) or a high molecular weight compound (macromolecule) (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more).
- the molecular weight of the epoxy compound (in the case of a polymer, the weight average molecular weight) is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the molecular weight (in the case of a polymer, the weight average molecular weight) is preferably 3000 or less, more preferably 2000 or less, still more preferably 1500 or less.
- epoxy compound examples include, for example, bisphenol A type epoxy resins such as jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (all manufactured by Mitsubishi Chemical Corporation).
- EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055 (all manufactured by DIC Co., Ltd.), etc.
- the bisphenol F type epoxy resin examples include jER806, jER807, jER4004, jER4005, jER4007, jER4010 (all manufactured by Mitsubishi Chemical Co., Ltd.).
- EPICLON830, EPICLON835 aboveve, manufactured by DIC Co., Ltd.), LCE-21, RE-602S (above, manufactured by Nippon Kayaku Co., Ltd.), etc.
- Examples of the phenol novolac type epoxy resin are jER152, jER154, jER157S70, jER157S65.
- EPICLON N-740 As the aliphatic epoxy resin, ADEKA RESIN EP-4080S, EP-4085S, EP-4088S (above, manufactured by ADEKA Co., Ltd.), celoxide 2021P, celoxide 2081, celoxide 2083, celoxide 2085, etc.
- EHPE3150, EPOLEAD PB 3600, PB 4700 (above, manufactured by Daicel Co., Ltd.), Denacol EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (above, manufactured by Nagase ChemteX Corporation) And so on.
- ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4011S aboveve, manufactured by ADEKA Corporation
- NC-2000, NC-3000, NC-7300, XD-1000 examples thereof include EPPN-501, EPPN-502 (all manufactured by ADEKA Corporation), jER1031S (manufactured by Mitsubishi Chemical Corporation) and the like.
- the content of the curable compound is preferably 1 to 50% by mass based on the total solid content of the coloring composition.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the polymerizable monomer is preferably 0.1 to 40% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 1% by mass or more, and more preferably 2% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less, and further preferably 10% by mass or less.
- the content of the polymerizable resin is preferably 1 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the total content of the polymerizable monomer and the polymerizable resin is preferably 1 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the polymerizable resin in the total amount of the polymerizable monomer and the polymerizable resin is preferably 70% by mass or more, and more preferably 80% by mass or more.
- the content of the epoxy compound is preferably 0.1 to 40% by mass based on the total solid content of the coloring composition.
- the lower limit is, for example, more preferably 1% by mass or more, further preferably 2% by mass or more.
- the upper limit is, for example, more preferably 30% by mass or less, further preferably 20% by mass or less.
- the epoxy compound may be used alone or in combination of two or more.
- the coloring composition contains a monomer having an ethylenically unsaturated group (polymerizable monomer) and a resin.
- M 1 / B 1 which is the ratio of the mass M 1 of the monomer having an ethylenically unsaturated group (polymerizable monomer) contained in the coloring composition to the mass B 1 of the resin contained in the coloring composition, is 0.35.
- the embodiment is as follows, preferably 0.25 or less, and more preferably 0.21 or less. According to the coloring composition of this aspect, a cured film having more excellent heat resistance can be formed. Further, it is possible to suppress the film shrinkage at the time of forming the cured film.
- the lower limit of the value of M 1 / B 1 is preferably 0.01 or more, more preferably 0.04 or more, and further preferably 0.07 or more.
- the mass B 1 of the resin is the total amount of the above-mentioned polymerizable resin and the other resin described later.
- the mass B 1 of the resin is the mass of the above-mentioned polymerizable resin.
- the mass B 1 of the resin is the mass of another resin.
- the total content of the polymerizable monomer and the resin is preferably 1 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the coloring composition of the present invention can further contain a resin containing no curable group (hereinafter, also referred to as another resin).
- a resin containing no curable group hereinafter, also referred to as another resin.
- Other resins are blended, for example, for the purpose of dispersing particles such as pigments in the composition and for the purpose of binders.
- a resin mainly used for dispersing particles such as pigments is also referred to as a dispersant.
- such an application of the resin is an example, and the resin can be used for a purpose other than such an application.
- the weight average molecular weight (Mw) of the other resin is preferably 2000 to 2000000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
- the lower limit is preferably 3000 or more, and more preferably 5000 or more.
- resins include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, and polyamide.
- examples thereof include imide resin, polyolefin resin, cyclic olefin resin, polyester resin and styrene resin.
- One of these resins may be used alone, or two or more thereof may be mixed and used.
- resins may have an acid group.
- the acid group include a carboxyl group, a phosphoric acid group, a sulfo group, a phenolic hydroxy group and the like, and a carboxyl group is preferable. These acid groups may be only one type or two or more types.
- the resin having an acid group can also be used as an alkali-soluble resin.
- a polymer having a carboxyl group in the side chain is preferable.
- alkali-soluble methacrylic acid copolymers acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, partially esterified maleic acid copolymers, and novolak resins.
- examples thereof include a phenol resin, an acidic cellulose derivative having a carboxyl group in the side chain, and a resin in which an acid anhydride is added to a polymer having a hydroxy group.
- a copolymer of (meth) acrylic acid and another monomer copolymerizable therewith is suitable as the alkali-soluble resin.
- Examples of other monomers copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, vinyl compounds and the like.
- alkyl (meth) acrylate and aryl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, and pentyl (meth) acrylate.
- the vinyl compound include styrene, ⁇ -methylstyrene, vinyltoluene, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, polystyrene macromonomer, polymethylmethacrylate macromonomer and the like.
- N-substituted maleimide monomers described in JP-A-10-300922 for example, N-phenylmaleimide, N-cyclohexylmaleimide and the like can also be used.
- the other monomers copolymerizable with these (meth) acrylic acids may be only one kind or two or more kinds.
- Resins having an acid group are benzyl (meth) acrylate / (meth) acrylic acid copolymer, benzyl (meth) acrylate / (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate copolymer, and benzyl (meth).
- a multi-polymer copolymer composed of acrylate / (meth) acrylic acid / other monomer can be preferably used.
- the resin having an acid group is also preferably a polymer containing a repeating unit derived from the above-mentioned monomer component containing an ether dimer.
- the resin having an acid group may contain a repeating unit derived from the compound represented by the following formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents an alkylene group having 2 to 10 carbon atoms
- R 3 represents a hydrogen atom or a benzene ring and may contain 1 to 20 carbon atoms.
- n represents an integer from 1 to 15.
- the acid value of the resin having an acid group is preferably 30 to 200 mgKOH / g.
- the lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more.
- the upper limit is preferably 150 mgKOH / g or less, and more preferably 120 mgKOH / g or less.
- the coloring composition of the present invention may also contain a resin as a dispersant.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable.
- the acid group contained in the acidic dispersant (acidic resin) is preferably a carboxyl group.
- the acid value of the acidic dispersant (acidic resin) is preferably 40 to 105 mgKOH / g, more preferably 50 to 105 mgKOH / g, and even more preferably 60 to 105 mgKOH / g.
- the basic dispersant (basic resin) represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group. Since the resin used as the dispersant contains a repeating unit having an acid group, it is possible to further reduce the residue generated on the base of the pixel when forming a pattern by the photolithography method.
- the resin used as the dispersant is also preferably a graft resin.
- the graft resin include resins having a repeating unit represented by the formula (A-1-2) described in the above-mentioned section of polymerizable resin.
- the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
- the resin used as the dispersant is a polyimine dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin to have is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom that exhibits basicity.
- the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and this content is incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
- a resin include dendrimers (including star-shaped polymers).
- specific examples of the dendrimer include the polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and Solsparse series manufactured by Japan Lubrizol K.K. For example, Solsparse 76500) and the like. Further, the pigment dispersant described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification. The resin described as the dispersant can also be used for purposes other than the dispersant. For example, it can also be used as a binder.
- the content of the other resin is preferably 30% by mass or less, preferably 20% by mass or less, based on the total solid content of the coloring composition of the present invention. Is more preferable, and 10% by mass or less is further preferable.
- the total content of the above-mentioned curable compound and other resins is preferably 1 to 50% by mass in the total solid content of the coloring composition of the present invention.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the coloring composition of the present invention preferably contains a photopolymerization initiator.
- the coloring composition of the present invention preferably further contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- the photopolymerization initiator includes trihalomethyltriazine compound, benzyldimethylketal compound, ⁇ -hydroxyketone compound, ⁇ -aminoketone compound, acylphosphine compound, phosphine oxide compound, metallocene compound, oxime compound, and triarylimidazole. It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxaziazole compound and a 3-aryl substituted coumarin compound, and an oxime compound and an ⁇ -hydroxyketone compound.
- ⁇ -Aminoketone compound, and acylphosphine compound are more preferable, and an oxime compound is further preferable.
- an oxime compound is further preferable.
- the photopolymerization initiator include compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, the contents of which are incorporated in the present specification.
- Examples of commercially available ⁇ -hydroxyketone compounds include IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, and IRGACURE-127 (all manufactured by BASF).
- Commercially available ⁇ -aminoketone compounds include IRGACURE-907, IRGACURE-369, IRGACURE-379, and IRGACURE-379EG (all manufactured by BASF).
- Examples of commercially available acylphosphine compounds include IRGACURE-819 and DAROCUR-TPO (all manufactured by BASF).
- Examples of the oxime compound include the compounds described in JP 2001-233842 A, the compounds described in JP 2000-080068 A, the compounds described in JP 2006-342166 A, the compounds described in J. C. S. The compound according to Perkin II (1979, pp. 1653-1660), J. Mol. C. S. The compound described in Perkin II (1979, pp. 156-162), the compound described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), the compound described in JP-A-2000-066385.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminovtan-2-one, 2-acetoxyimiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropan-1-one.
- IRGACURE-OXE01 IRGACURE-OXE02, IRGACURE-OXE03, IRGACURE-OXE04 (above, manufactured by BASF), TR-PBG-304 (manufactured by Joshu Powerful Electronics New Materials Co., Ltd.), ADEKA PTOMER N-1919.
- Photopolymerization initiator 2 described in JP 2012-014052 manufactured by ADEKA Corporation can be used.
- the oxime compound it is also preferable to use a compound having no coloring property or a compound having high transparency and being resistant to discoloration. Examples of commercially available products include ADEKA ARKULS NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation).
- an oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
- an oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include compounds described in paragraphs 0031 to 0047 of JP2013-114249A, paragraphs 0008 to 0012 and 0070 to 0079 of JP2014-137466A. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
- an oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, further preferably 2000 to 300,000, and more preferably 5000 to 200,000, from the viewpoint of sensitivity. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the coloring composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the coloring composition of the present invention is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention can contain a pigment derivative.
- the pigment derivative include compounds having a structure in which a part of the pigment is replaced with an acid group or a basic group.
- Examples of the pigment derivative include JP-A-56-118462, JP-A-63-264674, JP-A-01-217777, JP-A-03-009961, JP-A-03-026767, and JP-A-03. -153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063 No. 10, Japanese Patent Application Laid-Open No.
- the content of the pigment derivative is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group means a substituent which is directly bonded to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable.
- the silane coupling agent is preferably a compound having an alkoxysilyl group.
- functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group, and isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- Specific examples of the silane coupling agent include the compounds described in JP-A 2009-288703, paragraphs 0018 to 0036, and the compounds described in JP-A 2009-242604, paragraphs 0056 to 0066. Are incorporated herein by reference.
- the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the upper limit is preferably 3% by mass or less, and more preferably 2% by mass or less.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the silane coupling agent may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a solvent.
- the solvent include organic solvents.
- the solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the coloring composition.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like.
- paragraph number 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-dimethylpropanamide and the like.
- aromatic hydrocarbons benzene, toluene, xylene, ethylbenzene, etc.
- aromatic hydrocarbons for environmental reasons (for example, 50 mass ppm (parts per) with respect to the total amount of the organic solvent. It can be milion) or less, can be 10 mass ppm or less, or can be 1 mass ppm or less).
- a solvent having a low metal content it is preferable to use a solvent having a low metal content, and the metal content of the solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, a solvent at the mass ppt (parts per trillion) level may be used, and such a high-purity solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015).
- Examples of the method for removing impurities such as metals from the solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore size of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, still more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the coloring composition of the present invention does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulation.
- substantially free of the environmentally regulated substance means that the content of the environmentally regulated substance in the coloring composition is 50 mass ppm or less, and preferably 30 mass ppm or less. It is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- Examples of the method for reducing the environmentally regulated substance include a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance to the boiling point or higher, and distilling off the environmentally regulated substance from the system to reduce the amount. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to improve efficiency.
- a polymerization inhibitor or the like is added and distilled under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. You may.
- These distillation methods include a raw material stage, a product obtained by reacting the raw materials (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a coloring composition stage prepared by mixing these compounds. It is possible at any stage of.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- the liquid characteristics particularly, fluidity
- the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and liquid saving property, and has good solubility in the coloring composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, JP-A-2011- The surfactants described in paragraphs 0117 to 0132 of JP 132503 are mentioned and their contents are incorporated herein by reference.
- Commercially available products of fluorine-based surfactants include, for example, Megafuck F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS.
- the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
- fluorine-based surfactants include Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Megafuck. DS-21 can be mentioned.
- the fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having an alkyl fluoride group or an alkylene ether group, and a hydrophilic vinyl ether compound.
- a fluorine-based surfactant the description in JP-A-2016-216602 can be referred to, and the content thereof is incorporated in the present specification.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the following compounds are also exemplified as the fluorine-based surfactant used in the present invention.
- the weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example, 14,000.
- % indicating the ratio of the repeating unit is mol%.
- fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated group in the side chain can also be used.
- the compounds described in paragraphs 0050 to 0090 and paragraph numbers 0289 to 0295 of JP2010-164965 for example, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation. , RS-72-K and the like.
- the fluorine-based surfactant compounds described in paragraph numbers 0015 to 0158 of JP-A-2005-117327 can also be used.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, etc.
- silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (all, Toray Dow Corning Co., Ltd.) ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, manufactured by Momentive Performance Materials), KP-341, KF-6001, KF-6002 (above, (Shin-Etsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by Big Chemie) and the like.
- the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used. Examples of such a compound include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-068814.
- Examples include the compounds described in paragraphs 0061 to 0080 of JP 2016-162946, the contents of which are incorporated herein.
- Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.).
- Examples of the benzotriazole compound include MYUA series manufactured by Miyoshi Oil & Fats (Chemical Industry Daily, February 1, 2016). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one type of ultraviolet absorber may be used, or two or more types may be used.
- the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an antioxidant.
- the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
- a phosphorus-based antioxidant can also be preferably used.
- a phosphorus-based antioxidant tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosfepine-6 -Il] oxy] ethyl] amine, tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like.
- antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like.
- the antioxidants include the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in International Publication No. 2017/006600, and the compounds described in International Publication No. 2017/164024. It can also be used.
- the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably in the above range.
- the coloring compositions of the present invention include sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, etc.). It may contain a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension modifier, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074.
- the coloring composition of the present invention may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst.
- a compound in which the protecting group is eliminated and functions as an antioxidant can be mentioned.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- ADEKA ARKULS GPA-5001 manufactured by ADEKA Corporation
- C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the coloring composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less, and further preferably 10 ppm or less, which is not bonded or coordinated with a pigment or the like. , It is particularly preferable that it is not substantially contained.
- stabilization of pigment dispersibility agglomeration suppression
- improvement of spectral characteristics due to improvement of dispersibility agglomeration suppression
- stabilization of curable components suppression of conductivity fluctuation due to elution of metal atoms / metal ions
- Effects such as improvement of characteristics can be expected.
- Japanese Patent Application Laid-Open No. 2012-1537996 Japanese Patent Application Laid-Open No.
- JP-A-2010-083997 JP-A-2017-090930, JP-A-2018-025612, JP-A-2018-025797, JP-A-2017-155228, JP-A-2018-036521 and the like. The effect is also obtained.
- Examples of the types of free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, Examples thereof include Cs, Ni, Cd, Pb and Bi.
- the content of free halogen that is not bonded or coordinated with a pigment or the like is preferably 100 ppm or less, more preferably 50 ppm or less, and more preferably 10 ppm or less. It is more preferable, and it is particularly preferable that it is not substantially contained.
- Examples of the halogen include F, Cl, Br, I and their anions.
- Examples of the method for reducing free metals and halogens in the coloring composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.
- the coloring composition of the present invention does not substantially contain terephthalic acid ester.
- the container for the colored composition of the present invention is not particularly limited, and a known container can be used.
- a storage container a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used for the purpose of suppressing impurities from being mixed into raw materials and coloring compositions. It is also preferable to use. Examples of such a container include the container described in JP-A-2015-123351.
- the inner wall of the coloring composition is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the composition, and suppressing the alteration of components.
- the storage conditions for the coloring composition of the present invention are not particularly limited, and conventionally known methods can be used. Further, the method described in JP-A-2016-180058 can also be used.
- the coloring composition of the present invention can be produced by mixing the above-mentioned components.
- all the components may be simultaneously dissolved and / or dispersed in a solvent to produce the coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to produce a coloring composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and disperser for dispersing pigments are "Dispersion Technology Taizen, published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology and industrial application centered on suspension (solid / liquid dispersion system)". The process and disperser described in Paragraph No.
- the particles may be miniaturized in the salt milling step.
- the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- a fluororesin such as polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (for example, nylon-6, nylon-6,6), and a polyolefin resin such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- a filter using a material such as (including a polyolefin resin) can be mentioned.
- polypropylene (including high-density polypropylene) and nylon are preferable.
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
- fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Loki Techno Co., Ltd.
- filters for example, a first filter and a second filter
- the filtration with each filter may be performed only once or twice or more.
- filters having different pore diameters may be combined within the above-mentioned range.
- the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter.
- the cured film of the present invention is a cured film obtained from the above-mentioned coloring composition of the present invention.
- the cured film of the present invention can be used as a color filter or the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a red colored layer (red pixel) of a color filter.
- the film thickness of the cured film of the present invention can be appropriately adjusted according to the intended purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the color filter of the present invention has the cured film of the present invention described above. More preferably, it has the cured film of the present invention as the pixels of the color filter.
- the color filter of the present invention can be used for a solid-state image sensor such as a CCD (charge coupling element) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
- the film thickness of the cured film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the color filter of the present invention preferably has a pixel width of 0.5 to 20.0 ⁇ m.
- the lower limit is preferably 1.0 ⁇ m or more, and more preferably 2.0 ⁇ m or more.
- the upper limit is preferably 15.0 ⁇ m or less, and more preferably 10.0 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- each pixel included in the color filter of the present invention has high flatness.
- the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
- the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
- the surface roughness of the pixels can be measured using, for example, AFM (Atomic Force Microscope) Measurement 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
- the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest).
- the color filter of the present invention may be provided with a protective layer on the surface of the cured film of the present invention.
- a protective layer By providing the protective layer, various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching the molded resin with an adhesive.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
- the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
- the resin composition When the resin composition is applied to form the protective layer, a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber of light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., if necessary. May be contained.
- organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
- a known absorbent can be used as the light absorber of a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer
- the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the color filter of the present invention forms a pattern on the colored composition layer by a step of forming a colored composition layer on a support using the colored composition of the present invention described above and a photolithography method or a dry etching method. It can be manufactured through the process of
- Pattern formation by the photolithography method includes a step of forming a coloring composition layer on a support using the coloring composition of the present invention, a step of exposing the coloring composition layer in a pattern, and a step of exposing the coloring composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the coloring composition layer of the present invention is used to form the coloring composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use.
- a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
- a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film and the like may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix that separates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with an undercoat layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- a known method can be used as a method for applying the coloring composition.
- a dropping method drop casting
- a slit coating method for example, a spraying method; a roll coating method; a spin coating method (spin coating); a cast coating method; a slit and spin method; a pre-wet method (for example, JP 2009-145395A).
- inkjet for example, on-demand method, piezo method, thermal method
- ejection printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, etc. Examples include various printing methods; transfer methods using molds and the like; nanoimprint methods.
- the application method for inkjet is not particularly limited, and for example, the method shown in "Expandable / Usable Inkjet-Infinite Possibilities Seen in Patents-, Published in February 2005, Sumi Betechno Research" (especially from page 115). (Page 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, regarding the method of applying the coloring composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
- the colored composition layer formed on the support may be dried (prebaked).
- prebaking may not be performed.
- the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and further preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the coloring composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing the colored composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of light having a wavelength of 300 nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm) are preferable. Also, a long-wave light source of 300 nm or more can be used.
- pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a short cycle (for example, millisecond level or less).
- the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and even more preferably 30 nanoseconds or less.
- the lower limit of the pulse width is not particularly limited, but may be 1 femtosecond (fs) or more, and may be 10 femtoseconds or more.
- the frequency is preferably 1 kHz or higher, more preferably 2 kHz or higher, and even more preferably 4 kHz or higher.
- the upper limit of the frequency is preferably 50 kHz or less, more preferably 20 kHz or less, and further preferably 10 kHz or less.
- Maximum instantaneous intensity is preferably at 50000000W / m 2 or more, more preferably 100000000W / m 2 or more, more preferably 200000000W / m 2 or more.
- the upper limit of the maximum instantaneous intensity is preferably at 1000000000W / m 2 or less, more preferably 800000000W / m 2 or less, further preferably 500000000W / m 2 or less.
- the pulse width is the time during which light is irradiated in the pulse period.
- the frequency is the number of pulse cycles per second.
- the maximum instantaneous illuminance is the average illuminance within the time during which the light is irradiated in the pulse period.
- the pulse cycle is a cycle in which light irradiation and pause in pulse exposure are one cycle.
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment) or in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure illuminance can be set appropriately, and usually selected from the range of 1000 W/m 2 to 100000 W/m 2 (for example, 5000 W/m 2 , 15000 W/m 2 , or 35000 W/m 2 ). Can be done. Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed portion of the coloring composition layer is developed and removed to form a pattern (pixel).
- Development and removal of the unexposed portion of the coloring composition layer can be performed using a developing solution.
- the colored composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developing solution is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic substances.
- alkaline compounds examples include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferable.
- the developer may be once produced as a concentrated solution and diluted to a concentration required for use.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development.
- the rinsing is performed by supplying the rinsing liquid to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed. It is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support. At this time, when moving the nozzle from the central portion of the support to the peripheral portion, the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of rinsing can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion to the peripheral portion of the support.
- Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
- Post-baking can be performed on the developed film in a continuous or batch manner by using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Laid-Open No. 10-2017-0122130.
- Pattern formation by the dry etching method includes a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer.
- the photoresist layer it is preferable to further perform a prebaking treatment.
- a prebaking treatment it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
- a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
- the description in paragraphs 0010 to 0067 of JP2013-064993A can be referred to, and this content is incorporated in the present specification.
- the solid-state imaging device of the present invention has the cured film of the present invention described above.
- the configuration of the solid-state image sensor of the present invention is not particularly limited as long as it includes the cured film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge coupling element) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the configuration has a color filter on the device protective film.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of an image pickup apparatus having such a structure are described in JP2012-227478A, Japanese Patent Application Laid-Open No. 2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the image display device of the present invention has the cured film of the present invention described above.
- Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Institute Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- the acid value of the resin was determined by neutralization titration using an aqueous sodium hydroxide solution. Specifically, the solution in which the resin is dissolved in a solvent is titrated with an aqueous solution of sodium hydroxide using a potential difference measurement method to calculate the number of millimoles of the acid contained in 1 g of the solid content of the resin, and then the value thereof. was determined by multiplying the molecular weight of potassium hydroxide (KOH) by 56.1.
- KOH potassium hydroxide
- C C value (ethylenically unsaturated base value)>
- 0.1 g of the resin was dissolved in a mixed solution of tetrahydrofuran / methanol (50 mL / 15 mL), 10 mL of a 4 mol / L sodium hydroxide aqueous solution was added, and the mixture was reacted at 40 ° C. for 2 hours.
- the reaction solution was neutralized with 10.2 mL of a 4 mol / L methanesulfonic acid aqueous solution, and then a mixed solution containing 5 mL of ion-exchanged water and 2 mL of methanol was transferred to a 100 mL volumetric flask, and the mixture was pipette-up with methanol for HPLC measurement.
- ⁇ Preparation of magenta colorant solutions CMD1 to CMD2> The raw materials listed in the table below were mixed to obtain a mixed solution.
- the obtained mixed solution was subjected to dispersion treatment using an Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulation type disperser (bead mill) to prepare magenta colorant solutions CMD1 to CMD2.
- the numerical value described in the column of the mass part of the dispersant is the value of the solid content.
- Pigments R1 to R5 Compounds with the following structure.
- Pigment R1 is C.I. I. Pigment Red 272.
- Pigments CR1 to CR4 Compounds having the following structures.
- Pigment Y1 C.I. I. Pigment Yellow 138
- Pigment Y2 C.I. I. Pigment Yellow 139
- Pigment Y3 C.I. I. Pigment Yellow 150
- Pigment Y4 C.I. I. Pigment Yellow 185
- magenta color dye Magenta Dyes M1-M32: Salts of cationic cyanine chromophores and anions listed in the table below.
- the magenta color dyes M1 to M32 have a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C. of 1 g or more.
- Et represents an ethyl group
- Pr represents a propyl group
- Bu represents a butyl group
- Hex represents a hexyl group.
- Counter anions AJ-1 to AJ-4 Resins having anionic groups (AJ-1) to (AJ-4) produced by the following methods.
- AJ-1 67.3 parts by mass of methyl ethyl ketone was charged into a 4-port separable flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to 75 ° C. under a nitrogen stream.
- 2-acrylamide-2-methylpropanesulfonic acid 20.0 parts by mass, methyl methacrylate 12.5 parts by mass, n-butyl methacrylate 20.0 parts by mass, 2-ethylhexyl methacrylate 20.0 parts by mass, methacrylic acid 3.
- AJ-2 to AJ-4 Resins (AJ-2) to (AJ-4) were obtained in the same manner as the resin (AJ-1) except that the material composition was changed to that shown in the table below.
- Magenta color dye M33 A compound having the following structure (xanthene compound).
- the magenta color dye M33 has a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C. of 1 g or more.
- magenta color pigment Magenta color pigment CM1: C.I. I. Pigment Red 122 Magenta color pigment CM2: C.I. I. Pigment Red 177 Both the magenta color pigment CM1 and the magenta color pigment CM2 have a solubility in 100 g of water at 23 ° C. and a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C. of less than 0.1 g.
- Pigment derivative Sy1 Compound with the following structure
- Dispersant D3 Resin PA-1 produced by the following method In a three-necked flask, 60.78 g (PGMEA: 30.39 g, macromonomer B-1 (30.39 g)) of a macromonomer B-1 solution having a concentration (solid content) of 50% by mass, ⁇ -carboxy-poly. 50.99 g of caprolactone monoacrylate (Aronix M-5300, manufactured by Toa Synthetic Co., Ltd.) and 159.5 g of PGMEA (propylene glycol 1-monomethyl ether 2-acetate) were introduced to obtain a mixture. The mixture was stirred while blowing nitrogen. The mixture was then warmed to 75 ° C. while flowing nitrogen into the flask.
- PGMEA polypropylene glycol 1-monomethyl ether 2-acetate
- V-601 2,2'-azobis (methyl 2-methylpropionate)
- Macromonomer B-1 Compound having the following structure (Mw: 3000)
- Dispersant D4 Resin PA-2 produced by the following method 82.76 g (PGMEA: 41.38 g, macromonomer B-1 (41.38 g)) and ⁇ -carboxy-poly of a macromonomer B-1 solution having a concentration (solid content) of 50% by mass in a three-necked flask. 44.14 g of caprolactone monoacrylate (Aronix M-5300, manufactured by Toa Synthetic Co., Ltd.) and 159.5 g of PGMEA were introduced to obtain a mixture. The mixture was stirred while blowing nitrogen. The mixture was then warmed to 75 ° C. while flowing nitrogen into the flask.
- the weight average molecular weight (Mw) of the obtained resin PA-2 was 23,300, and the acid value was 60 mgKOH / mg.
- the C C value was 0.4 mmol / g, and the amine value was 0.3 mmol / g. Met.
- Resin B1 Resin having the following structure (the numerical value added to the main chain is the molar ratio. Mw: 30000)
- Resin B2 Resin having the following structure (the numerical value added to the main chain is the molar ratio. Mw: 11000)
- Resin B3 Resin having the following structure (the numerical value added to the main chain is the molar ratio. Mw: 10000)
- Polymerizable monomer Polymerizable Monomer
- Polymerizable Monomer E1 KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
- Polymerizable Monomer E2 NK Ester A-DPH-12E (manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
- Polymerizable Monomer E3 NK Ester A-TMMT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
- Polymerizable monomer E5 Dipentaerythritol hexaacrylate
- Polymerizable monomer E6 Dipentaerythritol pentaacrylate (photopolymerization initiator)
- Photopolymerization Initiator I1 IRGACURE 369 (manufactured by BASF)
- Surfactant F1 A compound having the following structure (in the formula below,% indicating the ratio of the repeating unit is mol%. Mw: 14000).
- CT-4000 (manufactured by FUJIFILM Electronics Materials Co., Ltd.) is applied on a glass substrate by a spin coating method so that the film thickness is 0.1 ⁇ m, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum.
- Each coloring composition was applied onto the glass substrate with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a coating film.
- the obtained coating film was irradiated with light having a wavelength of 365 nm and exposed at an exposure amount of 500 mJ / cm 2 . Then, it was heated at 220 ° C.
- the light transmittance (transmittance) in the range of 400 to 700 nm was measured using MCPD-3000 manufactured by Otsuka Electronics Co., Ltd.
- the cured film prepared above was heated at 265 ° C. for 5 minutes.
- the transmittance of the cured film after heating was measured, the maximum value of the amount of change in the transmittance was determined, and the heat resistance was evaluated according to the following criteria.
- the transmittance was measured 5 times for each sample, and the average value of the results of 3 times excluding the maximum value and the minimum value was adopted.
- the maximum value of the amount of change in the transmittance means the amount of change in the cured film before and after heating at the wavelength where the amount of change in the transmittance in the wavelength range of 400 to 700 nm is the largest.
- 2 The maximum value of the amount of change in transmittance exceeds 2.0% and is 2.5% or less.
- the maximum value of the amount of change in transmittance exceeds 2.5%.
- a cured film having excellent heat resistance could be produced by using the coloring composition of the example. Further, the cured film obtained from the coloring composition of Examples had preferable spectral characteristics as a red coloring layer.
- Pigment R1 is 10.64 parts by mass
- pigment derivative Sy1 is 1.33 parts by mass
- dispersant D1 is 1.99 parts by mass
- dispersant D2 is 1.99 parts by mass
- magenta dye M1 is 2. 02 parts by mass and 82.03 parts by mass of the solvent S1 were mixed to obtain a mixed solution.
- the obtained mixed solution was subjected to dispersion treatment using an Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulating dispersion device (bead mill) to prepare a dispersion solution MRD1.
- Example 1 60.91 parts by mass of the dispersion liquid MRD1 was added instead of the pigment dispersion liquid 1 and the magenta color colorant solution, but the same procedure as in Example 1 was carried out.
- the coloring composition of Example 63 was prepared. When the heat resistance was evaluated by the same method as described above using this coloring composition, the evaluation was "2".
- Example 1001 The Green composition was applied onto a silicon wafer by a spin coating method so that the film thickness after post-baking was 1.0 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), light having a wavelength of 365 nm was irradiated (exposed) with an exposure amount of 1000 mJ / cm 2 through a mask of a 2 ⁇ m square dot pattern. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH).
- TMAH tetramethylammonium hydroxide
- the Green composition was then patterned by heating (post-baking) at 200 ° C. for 5 minutes using a hot plate.
- the Red composition and the Blue composition were sequentially patterned to form green, red and blue coloring patterns (Bayer patterns).
- the coloring composition of Example 3 was used.
- the Green composition and the Blue composition will be described later.
- the Bayer pattern includes one red (Red) element, two green (Green) elements, and one blue (Blue) element as disclosed in US Pat. No. 3,971,065. It is a pattern in which a 2 ⁇ 2 array of color filter elements is repeated.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had a suitable image recognition ability.
- Green Pigment Dispersion C. I. Pigment Green 36 at 6.4 parts by mass
- C.I. I. A mixed solution consisting of 5.3 parts by mass of Pigment Yellow 150, 5.2 parts by mass of dispersant (Disperbyk-161, manufactured by BYK Chemie), and 83.1 parts by mass of PGMEA is used in a bead mill (zirconia beads 0.3 mm diameter).
- a pigment dispersion was prepared by mixing and dispersing for 3 hours.
- a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment was repeated 10 times to prepare a Green pigment dispersion.
- Green pigment dispersion 73.7 parts by mass 40% by mass of resin
- B2 PGMEA solution 0.3 parts by mass
- Polymerizable monomer E1: 1.2 parts by mass
- Photopolymerization initiator I2 0.6 parts by mass Of the surfactant
- F1 1% by mass PGMEA solution 4.2 parts by mass UV absorber (UV-503, manufactured by Daito Kagaku Co., Ltd.): 0.5 parts by mass PGMEA: 19.5 parts by mass
- a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment was repeated 10 times to prepare a Blue pigment dispersion.
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Abstract
Description
<1> ジケトピロロピロール顔料と、マゼンタ色染料と、硬化性基を有する化合物と、を含み、
ジケトピロロピロール顔料は、芳香族環に電子供与性基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aを含む、着色組成物。
<2> 上記顔料Aが有する上記電子供与性基は、ヒドロキシ基、アルキル基、アルコキシ基、アルキルチオ基、アリールオキシ基およびアミノ基から選ばれる少なくとも1種である、<1>に記載の着色組成物。
<3> 上記顔料Aが有する上記電子供与性基が炭素数1~3のアルキル基である、<1>に記載の着色組成物。
<4> 上記顔料Aが有する上記芳香族環基は、下記式(AR-1)で表される基である、<1>~<3>のいずれか1つに記載の着色組成物;
<5> 上記顔料Aは、下記式(1)で表される化合物である、<1>~<4>のいずれか1つに記載の着色組成物;
<6> 上記顔料Aは、下記式(2)で表される化合物である、<1>~<5>のいずれか1つに記載の着色組成物;
<7> 上記顔料Aは赤色顔料である、<1>~<6>のいずれか1つに記載の着色組成物。
<8> 上記マゼンタ色染料は、キナクリドン化合物、キサンテン化合物、トリアリールメタン化合物、シアニン化合物、アントラキノン化合物およびジピロメテン化合物からなる群から選択される少なくとも1種を含む、<1>~<7>のいずれか1つに記載の着色組成物。
<9> 上記マゼンタ色染料は、カチオン性シアニン発色団とイミドアニオンとの塩を含む、<1>~<7>のいずれか1つに記載の着色組成物。
<10> 上記顔料Aの100質量部に対して、上記マゼンタ色染料を1~50質量部含む、<1>~<9>のいずれか1つに記載の着色組成物。
<11> 更に、黄色着色剤を含む、<1>~<10>のいずれか1つに記載の着色組成物。
<12> 上記硬化性基を有する化合物は、エチレン性不飽和基を有する化合物を含み、上記着色組成物は更に光重合開始剤を含む、<1>~<11>のいずれか1つに記載の着色組成物。
<13> 上記着色組成物の全固形分中における上記顔料Aの含有量が40質量%以上である、<1>~<12>のいずれか1つに記載の着色組成物。
<14> 上記ジケトピロロピロール顔料は、上記顔料Aを2種以上含む、<1>~<13>のいずれか1つに記載の着色組成物。
<15> 上記ジケトピロロピロール顔料は、更に、上記顔料A以外のジケトピロロピロール顔料を含む、<1>~<14>のいずれか1つに記載の着色組成物。
<16> 固体撮像素子用である、<1>~<15>のいずれか1つに記載の着色組成物。
<17> カラーフィルタ用である、<1>~<16>のいずれか1つに記載の着色組成物。
<18> <1>~<17>のいずれか1つに記載の着色組成物から得られる硬化膜。
<19> <1>~<17>のいずれか1つに記載の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を有するパターン形成方法。
<20> <18>に記載の硬化膜を有するカラーフィルタ。
<21> <18>に記載の硬化膜を有する固体撮像素子。
<22> <18>に記載の硬化膜を有する画像表示装置。 As a result of diligent studies by the present inventor, it has been found that the above object can be achieved by a coloring composition described later, and the present invention has been completed. Therefore, the present invention provides the following.
<1> Contains a diketopyrrolopyrrole pigment, a magenta color dye, and a compound having a curable group.
The diketopyrrolopyrrole pigment is a coloring composition containing a pigment A having a structure in which an aromatic ring group in which an electron-donating group is introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton.
<2> The coloring composition according to <1>, wherein the electron donating group contained in the pigment A is at least one selected from a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group and an amino group. Stuff.
<3> The coloring composition according to <1>, wherein the electron-donating group of the pigment A is an alkyl group having 1 to 3 carbon atoms.
<4> The coloring composition according to any one of <1> to <3>, wherein the aromatic ring group contained in the pigment A is a group represented by the following formula (AR-1);
<5> The coloring composition according to any one of <1> to <4>, wherein the pigment A is a compound represented by the following formula (1);
<6> The coloring composition according to any one of <1> to <5>, wherein the pigment A is a compound represented by the following formula (2);
<7> The coloring composition according to any one of <1> to <6>, wherein the pigment A is a red pigment.
<8> The magenta color dye is any of <1> to <7>, which comprises at least one selected from the group consisting of a quinacridone compound, a xanthene compound, a triarylmethane compound, a cyanine compound, an anthraquinone compound and a dipyrromethene compound. The coloring composition according to one.
<9> The coloring composition according to any one of <1> to <7>, wherein the magenta color dye contains a salt of a cationic cyanine chromophore and an imide anion.
<10> The coloring composition according to any one of <1> to <9>, which contains 1 to 50 parts by mass of the magenta color dye with respect to 100 parts by mass of the pigment A.
<11> The coloring composition according to any one of <1> to <10>, further comprising a yellow colorant.
<12> The compound having a curable group includes a compound having an ethylenically unsaturated group, and the coloring composition further contains a photopolymerization initiator, according to any one of <1> to <11>. Coloring composition.
<13> The coloring composition according to any one of <1> to <12>, wherein the content of the pigment A in the total solid content of the coloring composition is 40% by mass or more.
<14> The coloring composition according to any one of <1> to <13>, wherein the diketopyrrolopyrrole pigment contains two or more of the pigments A.
<15> The coloring composition according to any one of <1> to <14>, wherein the diketopyrrolopyrrole pigment further contains a diketopyrrolopyrrole pigment other than the pigment A.
<16> The coloring composition according to any one of <1> to <15>, which is used for a solid-state image sensor.
<17> The coloring composition according to any one of <1> to <16>, which is used for a color filter.
<18> A cured film obtained from the coloring composition according to any one of <1> to <17>.
<19> A step of forming a coloring composition layer on a support using the coloring composition according to any one of <1> to <17>, and a coloring composition layer by a photolithography method or a dry etching method. A pattern forming method comprising a step of forming a pattern with respect to a pattern.
<20> A color filter having the cured film according to <18>.
<21> A solid-state image sensor having the cured film according to <18>.
<22> An image display device having the cured film according to <18>.
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。例えば、顔料は、23℃の水100gに対する溶解度および23℃のプロピレングリコールモノメチルエーテルアセテート100gに対する溶解度がいずれも0.1g未満であることが好ましく、0.01g以下であることがより好ましい。
本明細書において、染料とは、溶剤に対して溶解しやすい化合物を意味する。例えば、染料は、23℃の水100gに対する溶解度、または、23℃のプロピレングリコールモノメチルエーテルアセテート100gに対する溶解度が、0.1g以上であることが好ましく、1g以上であることがより好ましい。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。 The contents of the present invention will be described in detail below.
In the present specification, "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
In the notation of a group (atomic group) in the present specification, the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group). For example, the "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
As used herein, "(meth) acrylate" represents both acrylate and methacrylate, or either, and "(meth) acrylic" represents both acrylic and methacrylic, or "(meth) acrylate." ) Acryloyl "represents both acryloyl and / or methacryloyl.
In the present specification, the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
As used herein, the term pigment means a compound that is difficult to dissolve in a solvent. For example, the pigment has a solubility in 100 g of water at 23 ° C. and a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., both of which are preferably less than 0.1 g, more preferably 0.01 g or less.
As used herein, the term dye means a compound that is easily soluble in a solvent. For example, the dye has a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., preferably 0.1 g or more, and more preferably 1 g or more.
In the present specification, the total solid content refers to the total mass of components excluding the solvent from all components of the composition.
In the present specification, the term "process" is included in this term not only as an independent process but also as long as the desired action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
本発明の着色組成物は、ジケトピロロピロール顔料と、マゼンタ色染料と、硬化性基を有する化合物と、を含み、ジケトピロロピロール顔料は、芳香族環に電子供与性基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aを含むことを特徴とする。 <Coloring composition>
The coloring composition of the present invention contains a diketopyrrolopyrrole pigment, a magenta color dye, and a compound having a curable group, and the diketopyrrolopyrrole pigment has an electron donating group introduced into the aromatic ring. It is characterized by containing a pigment A having a structure in which an aromatic ring group is bonded to a diketopyrrolopyrrole skeleton.
本発明の着色組成物はジケトピロロピロール顔料を含有する。本発明の着色組成物に用いられるジケトピロロピロール顔料は赤色顔料であることが好ましい。また、ジケトピロロピロール顔料は、23℃の水100gに対する溶解度および23℃のプロピレングリコールモノメチルエーテルアセテート100gに対する溶解度がいずれも0.1g未満であることが好ましく、0.01g以下であることがより好ましい。 << Diketopyrrolopyrrole Pigment >>
The coloring composition of the present invention contains a diketopyrrolopyrrole pigment. The diketopyrrolopyrrole pigment used in the coloring composition of the present invention is preferably a red pigment. Further, the diketopyrrolopyrrole pigment preferably has a solubility in 100 g of water at 23 ° C. and a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C., preferably less than 0.1 g, and more preferably 0.01 g or less. preferable.
本発明の着色組成物は、ジケトピロロピロール顔料として、芳香族環に電子供与性基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料A(以下、顔料Aという)を含有する。 (Pigment A)
The coloring composition of the present invention is a pigment A (hereinafter, pigment A) having a structure in which an aromatic ring group having an electron donating group introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton as a diketopyrrolopyrrole pigment. ) Is contained.
アルキル基、アルコキシ基およびアルキルチオ基の炭素数は、1~10が好ましく、1~5がより好ましく、1~3が更に好ましい。これらの基は直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましく、直鎖が更に好ましい。
アリールオキシ基の炭素数は、6~20が好ましく、6~10がより好ましい。
アミノ基としては、-NRa1Ra2で表される基が挙げられる。Ra1およびRa2は、それぞれ独立して水素原子、アルキル基、アリール基または複素環基を表す。Ra1とRa2が結合して環を形成してもよい。Ra1およびRa2が表すアルキル基の炭素数は、1~30が好ましく、1~15がより好ましく、1~8が更に好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましく、直鎖がより好ましい。Ra1およびRa2が表すアリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。Ra1およびRa2が表す複素環基は、単環であってもよく、縮合環であってもよい。複素環基は、単環または縮合数が2~4の縮合環が好ましい。複素環基の環を構成するヘテロ原子の数は1~3が好ましい。複素環基の環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。複素環基の環を構成する炭素原子の数は3~30が好ましく、3~18がより好ましく、3~12がより好ましい。 An electron-donating group is an atomic group that donates an electron to an atomic group substituted by an inductive effect or a resonance effect in organic electron theory. Examples of the electron-donating group include those having a negative value as the substituent constant (σp (para)) of Hammett's law. The Hammett equation substituent constant (σp (para)) can be quoted from the 5th edition of the Basics of Chemistry Handbook (page II-380). Specific examples of the electron donating group include a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group and an amino group.
The number of carbon atoms of the alkyl group, the alkoxy group and the alkylthio group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. These groups may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
The aryloxy group preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms.
Examples of the amino group include a group represented by −NRa 1 Ra 2 . Ra 1 and Ra 2 independently represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, respectively. Ra 1 and Ra 2 may be combined to form a ring. The alkyl group represented by Ra 1 and Ra 2 has a preferably 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 8 carbon atoms. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear. The number of carbon atoms of the aryl group represented by Ra 1 and Ra 2 is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. The heterocyclic group represented by Ra 1 and Ra 2 may be a monocyclic ring or a condensed ring. The heterocyclic group is preferably a single ring or a fused ring having 2 to 4 condensation numbers. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. The hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
R21およびR22はそれぞれ独立して電子供与性基を表し、
n11およびn12はそれぞれ独立して0~4の整数を表す。 In the above formula, R 11 and R 12 each independently represent a substituent.
R 21 and R 22 each independently represent an electron donating group.
n11 and n12 each independently represent an integer of 0 to 4.
置換基Tとしては、ハロゲン原子、シアノ基、ニトロ基、アルキル基、アリール基、複素環基、-ORt1、-CORt1、-COORt1、-OCORt1、-NRt1Rt2、-NHCORt1、-CONRt1Rt2、-NHCONRt1Rt2、-NHCOORt1、-SRt1、-SO2Rt1、-SO2ORt1、-NHSO2Rt1または-SO2NRt1Rt2が挙げられる。Rt1およびRt2は、それぞれ独立して水素原子、アルキル基、アリール基または複素環基を表す。Rt1とRt2が結合して環を形成してもよい。 (Substituent T)
The substituent T includes a halogen atom, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, -ORt 1 , -CORt 1 , -COORt 1 , -OCORt 1 , -NRt 1 Rt 2 , and -NHCORt 1. , -CONRt 1 Rt 2 , -NHCONRt 1 Rt 2 , -NHCOORt 1 , -SRt 1 , -SO 2 Rt 1 , -SO 2 ORt 1 , -NHSO 2 Rt 1 or -SO 2 NRt 1 Rt 2 . Rt 1 and Rt 2 independently represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, respectively. Rt 1 and Rt 2 may be combined to form a ring.
アルキル基の炭素数は、1~30が好ましく、1~15がより好ましく、1~8が更に好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましく、直鎖がより好ましい。
アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。
複素環基は、単環であってもよく、縮合環であってもよい。複素環基は、単環または縮合数が2~4の縮合環が好ましい。複素環基の環を構成するヘテロ原子の数は1~3が好ましい。複素環基の環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。複素環基の環を構成する炭素原子の数は3~30が好ましく、3~18がより好ましく、3~12がより好ましい。
アルキル基、アリール基および複素環基は、置換基を有していてもよく、無置換であってもよい。置換基としては、上述した置換基Tで説明した置換基が挙げられる。 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 8. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
The heterocyclic group may be a monocyclic ring or a condensed ring. The heterocyclic group is preferably a single ring or a fused ring having 2 to 4 condensation numbers. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. The hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
The alkyl group, aryl group and heterocyclic group may have a substituent or may be unsubstituted. Examples of the substituent include the substituent described in the above-mentioned Substituent T.
本発明の着色組成物は、上述した顔料A以外のジケトピロロピロール顔料(以下、他のジケトピロロピロール顔料ともいう)を含有することができる。他のジケトピロロピロール顔料は赤色顔料であることが好ましい。他のジケトピロロピロール顔料としては、下記式(10)で表される化合物などが挙げられる。
The coloring composition of the present invention can contain a diketopyrrolopyrrole pigment other than the pigment A described above (hereinafter, also referred to as another diketopyrrolopyrrole pigment). The other diketopyrrolopyrrole pigment is preferably a red pigment. Examples of other diketopyrrolopyrrole pigments include compounds represented by the following formula (10).
本発明の着色組成物はマゼンタ色染料を含有する。ここで、本明細書において、マゼンタ色とは緑色の補色の色相のことである。また、補色とは、色相環(color circle)で正反対に位置する関係の色の組合せのことである。また、マゼンタ色染料とはマゼンタ色の色相を呈する染料のことである。 << Magenta color dye >>
The coloring composition of the present invention contains a magenta dye. Here, in the present specification, the magenta color is the hue of the complementary color of green. Further, the complementary color is a combination of colors having a relationship of being located opposite to each other on the color wheel. The magenta color dye is a dye that exhibits a magenta hue.
式中、λ1はマゼンタ色染料の極大吸収波長の吸光度を1とした場合に、吸光度が0.5となる極大吸収波長よりも短波長側の波長であり、λ2はマゼンタ色染料の極大吸収波長の吸光度を1とした場合に、吸光度が0.5となる極大吸収波長よりも長波長側の波長である。 Δλ = λ2-λ1 (1)
In the formula, λ1 is a wavelength on the shorter wavelength side than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance at the maximum absorption wavelength of the magenta color dye is 1, and λ2 is the maximum absorption wavelength of the magenta color dye. This is a wavelength on the longer wavelength side than the maximum absorption wavelength at which the absorbance is 0.5 when the absorbance of is 1.
カチオン性シアニン発色団としては、下記式(Cy1)で表される構造が挙げられる。 (Cationic cyanine chromophore)
Examples of the cationic cyanine chromophore include a structure represented by the following formula (Cy1).
Rc1~Rc3が表す炭化水素基としては、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。 Examples of the halogen atom represented by R c1 to R c3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the hydrocarbon group represented by R c1 to R c3 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. Here, the term "alicyclic hydrocarbon group" as used herein is a concept excluding an aliphatic hydrocarbon group having no cyclic structure.
-Lp1-Rp1 ・・・(P-1)
式中、Lp1は単結合または連結基を表し、Rp1は架橋性基を表す。Lp1が表す連結基としては、アルキレン基、アリーレン基、-O-、-CO-、-NH-、-COO-、-OCO-、-CONH-、-NHCO-およびこれらを組み合わせてなる基が挙げられる。Rp1が表す架橋性基としては、(メタ)アクリロイル基、ビニル基、エポキシ基、イソシアネート基などが挙げられる。 An organic group having a crosslinkable group indicates a group composed of an atomic group containing a crosslinkable group, containing a carbon atom-hydrogen atom bond as a whole, and optionally containing an atom other than carbon. Specifically, a group represented by the following formula (P-1) can be mentioned.
-L p1- R p1 ... (P-1)
In the formula, L p1 represents a single bond or a linking group and R p1 represents a crosslinkable group. Examples of the linking group represented by L p1 include an alkylene group, an arylene group, -O-, -CO-, -NH-, -COO-, -OCO-, -CONH-, -NHCO- and a group formed by combining these. Can be mentioned. Examples of the crosslinkable group represented by R p1 include a (meth) acryloyl group, a vinyl group, an epoxy group, and an isocyanate group.
対アニオンとしては、ハロゲン化物アニオン(フッ素アニオン、塩素アニオン、臭素アニオン、ヨウ素アニオンなど)、過ハロゲン酸アニオン(ClO4 -、FO4 -、BrO4 -、IO4 -等)、チオシアン酸アニオン(SCN-等)、硫酸アニオン、ヘテロポリ酸、カルボン酸アニオン、スルホン酸アニオン、脂肪酸アニオン、フッ素基含有ホウ素アニオン、フッ素基含有リンアニオン、イミドアニオン、メチドアニオン、アニオン性基を側鎖に有する樹脂などが挙げられる。具体例としては、特開2015-232642号公報の段落番号0048~0144、特開2017-066377号公報の段落番号0034~0063に記載されたアニオンが挙げられる。なかでも、より優れた耐熱性を有する硬化膜を形成しやすいという理由から、アニオン性基を側鎖に有する樹脂およびイミドアニンであることが好ましく、イミドアニオンであることがより好ましい。すなわち、本発明で用いられるマゼンタ色染料は、より優れた耐熱性を有する硬化膜が得られやすいという理由から、カチオン性シアニン発色団とイミドアニオンとの塩、および、カチオン性シアニン発色団とアニオン性基を側鎖に有する樹脂との塩であることが好ましく、カチオン性シアニン発色団とイミドアニオンとの塩であることがより好ましい。 (Anion)
As the counter anion, halide anions (fluorine anion, chlorine anion, bromine anion, iodine anion), perhalogen acid anion (ClO 4 -, FO 4 - , BrO 4 -, IO 4 - , etc.), thiocyanate anions ( SCN - etc.), Sulfate anion, heteropolyacid, carboxylic acid anion, sulfonic acid anion, fatty acid anion, fluorine group-containing boron anion, fluorine group-containing phosphorus anion, imide anion, methide anion, resin having anionic group in the side chain, etc. Can be mentioned. Specific examples include the anions described in paragraphs 0048 to 0144 of JP2015-232642A and paragraphs 0034 to 0063 of JP2017-066377A. Among them, a resin having an anionic group in the side chain and an imide anion are preferable, and an imide anion is more preferable, because it is easy to form a cured film having more excellent heat resistance. That is, the magenta dye used in the present invention is a salt of a cationic cyanine chromophore and an imide anion, and a cationic cyanine chromophore and an anion, because a cured film having better heat resistance can be easily obtained. It is preferably a salt with a resin having a sex group in the side chain, and more preferably a salt with a cationic cyanine chromophore and an imide anion.
イミドアニオンとしては、式(AN-1)で表されるアニオン、および、式(AN-2)で表されるアニオンが挙げられ、式(AN-2)で表されるアニオンであることが好ましい。 [Imid anion]
Examples of the imide anion include an anion represented by the formula (AN-1) and an anion represented by the formula (AN-2), and an anion represented by the formula (AN-2) is preferable. ..
X1およびX2が表す芳香族炭化水素基としては、アリール基等を挙げることができる。芳香族炭化水素基の炭素数は、好ましくは6~20、より好ましくは6~14、更に好ましくは6~10である。芳香族炭化水素基の具体例としては、フェニル基、ビフェニリル基、ナフチル基等が挙げられる。 Examples of the alicyclic hydrocarbon group represented by X 1 and X 2 include a cyclic alkyl group (cycloalkyl group), a cyclic alkenyl group (cycloalkenyl group), a condensed polycyclic hydrocarbon group, and a bridging ring hydrocarbon group. Examples thereof include a spiro hydrocarbon group and a cyclic terpene hydrocarbon group. The number of carbon atoms of the aliphatic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 12. Specific examples of the alicyclic hydrocarbon group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group and the like.
Examples of the aromatic hydrocarbon group represented by X 1 and X 2 include an aryl group and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 10. Specific examples of the aromatic hydrocarbon group include a phenyl group, a biphenylyl group, a naphthyl group and the like.
Y2は、ハロゲン原子を表すか、ハロゲン化炭化水素基を表すか、又は炭素原子、水素原子若しくはハロゲン原子以外の原子を含む連結基と、ハロゲン置換アルキレン基と、アルキル基、脂環式炭化水素基、ヘテロアリール基及びアリール基から選ばれる1価の基とを組み合わせてなる基を表す。 In formula (AN-2), Y 1 represents a group having a polymerizable group.
Y 2 represents a halogen atom, a halogenated hydrocarbon group, or a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom, a halogen-substituted alkylene group, an alkyl group, and an alicyclic hydrocarbon. Represents a group formed by combining a monovalent group selected from a hydrogen group, a heteroaryl group and an aryl group.
Ry20及びRy22は、それぞれ独立して、アルキル基、脂環式炭化水素基、ヘテロアリール基又は置換若しくは非置換のアリール基を表し、
Ry21及びRy23は、それぞれ独立してアルキレン基を表し、
nは1以上の整数を表し、
*は結合手を表す。 In the formula (Y2-1), R y1 is a hydrogen atom, a fluorine atom, an alkyl group, an alkyl fluoride group, an alicyclic hydrocarbon group, an alkoxy group, an alkoxy fluoride group, R y20 COOR y21 -or R y22 COOR. Represents y23 CFH-
R y20 and R y22 each independently represent an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group.
R y21 and R y23 each independently represent an alkylene group.
n represents an integer greater than or equal to 1 and represents
* Represents a bond.
Q1-L1-* ・・・(Y1-1) Y 1 of the formula (AN-2) represents a group having a polymerizable group. The group having a polymerizable group represented by Y 1 is preferably a group represented by the formula (Y1-1).
Q 1- L 1- * ・ ・ ・ (Y1-1)
L1が表す2価の連結基は、炭素数1~10のアルキレン基;炭素数6~20のアリーレン基;炭素数7~20のアリーレンアルキレン基;炭素数1~10のアルキレン基及び炭素数6~20のアリーレン基から選ばれる少なくとも1種と、-O-、-S-、-COO-、-CONRa-及び-SO2-から選ばれる少なくとも1種とを組み合わせてなる基が好ましい。 Examples of the divalent linking group represented by L 1, a divalent hydrocarbon group; a divalent hydrocarbon group and -NR a -, - SO -, - SO 2 -, - CO -, - O -, - COO Examples thereof include a group formed by combining a group selected from-, -OCO-, -CONR a- , -NR a CO- and -S-. Ra represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Examples of the divalent hydrocarbon group include an alkylene group and an arylene group. In the divalent hydrocarbon group, at least a part of hydrogen atoms may be substituted with halogen atoms (preferably fluorine atoms).
The divalent linking group represented by L 1 is an alkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; an arylene alkylene group having 7 to 20 carbon atoms; an alkylene group having 1 to 10 carbon atoms and a carbon number of carbon atoms. A group consisting of a combination of at least one selected from 6 to 20 arylene groups and at least one selected from -O-, -S-, -COO-, -CONR a- and -SO 2- is preferable.
Q1-L2-SO2-* ・・・(Y1-2) The group having a polymerizable group represented by Y 1 of the formula (AN-2) is preferably a group represented by the formula (Y1-2) from the viewpoint of heat resistance.
Q 1- L 2- SO 2- * ・ ・ ・ (Y1-2)
アニオン性基を側鎖に有する樹脂としては、下記式(AN-10)で表される繰り返し単位を有する樹脂が挙げられる。
式(AN-10)
Examples of the resin having an anionic group in the side chain include a resin having a repeating unit represented by the following formula (AN-10).
Equation (AN-10)
本発明の着色組成物はジケトピロロピロール顔料およびマゼンタ色染料以外の着色剤(以下、他の着色剤ともいう)を含有することができる。他の着色剤は、顔料であってもよく、染料であってもよい。顔料と染料とを併用してもよい。本発明で用いられる他の着色剤は、顔料を含むことが好ましい。また、顔料は有機顔料であってもよく、無機顔料であってもよい。また、顔料には、無機顔料または有機‐無機顔料の一部を有機発色団で置換した材料を用いることもできる。無機顔料や有機‐無機顔料を有機発色団で置換することで、色相設計をしやすくできる。
他の着色剤中における顔料の含有量は、50質量%以上であることが好ましく、70質量%以上であることがより好ましく、80質量%以上であることが更に好ましく、90質量%以上であることが特に好ましい。また、他の着色剤は顔料のみであってもよい。 << Other colorants >>
The coloring composition of the present invention can contain a coloring agent other than the diketopyrrolopyrrole pigment and the magenta color dye (hereinafter, also referred to as other coloring agents). The other colorant may be a pigment or a dye. Pigments and dyes may be used in combination. Other colorants used in the present invention preferably contain pigments. Further, the pigment may be an organic pigment or an inorganic pigment. Further, as the pigment, an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can be used. Hue design can be facilitated by replacing inorganic pigments and organic-inorganic pigments with organic chromophores.
The content of the pigment in the other colorants is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 80% by mass or more, and 90% by mass or more. Is particularly preferred. Moreover, the other colorant may be only a pigment.
C.I.ピグメントグリーン7,10,36,37,58,59,62,63等、
C.I.ピグメントバイオレット1,19,23,27,32,37,42,60(トリアリールメタン系),61(キサンテン系)等、
C.I.ピグメントブルー1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87(モノアゾ系),88(メチン/ポリメチン系)等、
C.I.ピグメントレッド1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,270,279,294(キサンテン系、Organo Ultramarine、Bluish Red),295(モノアゾ系),296(ジアゾ系)等。 C. I. Pigment Orange 2,5,13,16,17: 1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73, etc. ,
C. I. Pigment Green 7,10,36,37,58,59,62,63, etc.
C. I. Pigment Violet 1,19,23,27,32,37,42,60 (triarylmethane type), 61 (xanthene type), etc.
C. I. Pigment Blue 1,2,15,15: 1,15: 2,15: 3,15: 4,15: 6,16,22,29,60,64,66,79,80,87 (monoazo system), 88 (methine / polymethine type), etc.
C. I. Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48: 1,48: 2,48: 3,48: 4, 49,49: 1,49: 2,52: 1,52: 2,53: 1,57: 1,60: 1,63: 1,66,67,81: 1,81: 2,81: 3, 83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184 185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,270,279,294 (xanthene, Organo Ultramarine, Bluesh Red), 295 (monoazo system), 296 (diazo system), etc.
また、黄色着色剤の含有量は、顔料Aの100質量部に対して40質量部以下であることが好ましい。下限は、1質量部以上であることが好ましく、3質量部以上であることがより好ましく、5質量部以上であることが更に好ましい。上限は、30質量部以下であることが好ましく、20質量部以下であることがより好ましい。
また、黄色着色剤の含有量は、マゼンタ色染料の100質量部に対して100質量部以下であることが好ましい。下限は、5質量部以上であることが好ましく、10質量部以上であることがより好ましく、15質量部以上であることが更に好ましい。上限は、80質量部以下であることが好ましく、60質量部以下であることがより好ましい。
また、黄色着色剤の含有量は、顔料Aとマゼンタ色染料との合計100質量部に対して50質量部以下であることが好ましい。下限は、1質量部以上であることが好ましく、3質量部以上であることがより好ましく、5質量部以上であることが更に好ましい。上限は、40質量部以下であることが好ましく、30質量部以下であることがより好ましい。
また、顔料Aとマゼンタ色染料と他の着色剤との合計の含有量は着色組成物の全固形分中40~90質量%であることが好ましい。下限は、45質量%以上であることが好ましく、50質量%以上であることがより好ましい。上限は、85質量%以下であることが好ましく、80質量%以下であることがより好ましい。
また、顔料Aとマゼンタ色染料と黄色着色剤との合計の含有量は着色組成物の全固形分中40~90質量%であることが好ましい。下限は、45質量%以上であることが好ましく、50質量%以上であることがより好ましい。上限は、85質量%以下であることが好ましく、80質量%以下であることがより好ましい。 The content of the other colorant is preferably 40 parts by mass or less with respect to 100 parts by mass of the pigment A. The lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more. The upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
The content of the yellow colorant is preferably 40 parts by mass or less with respect to 100 parts by mass of the pigment A. The lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more. The upper limit is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
The content of the yellow colorant is preferably 100 parts by mass or less with respect to 100 parts by mass of the magenta dye. The lower limit is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and further preferably 15 parts by mass or more. The upper limit is preferably 80 parts by mass or less, and more preferably 60 parts by mass or less.
The content of the yellow colorant is preferably 50 parts by mass or less with respect to 100 parts by mass in total of the pigment A and the magenta color dye. The lower limit is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more. The upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
The total content of the pigment A, the magenta dye, and the other colorants is preferably 40 to 90% by mass in the total solid content of the coloring composition. The lower limit is preferably 45% by mass or more, and more preferably 50% by mass or more. The upper limit is preferably 85% by mass or less, and more preferably 80% by mass or less.
The total content of the pigment A, the magenta dye, and the yellow colorant is preferably 40 to 90% by mass in the total solid content of the coloring composition. The lower limit is preferably 45% by mass or more, and more preferably 50% by mass or more. The upper limit is preferably 85% by mass or less, and more preferably 80% by mass or less.
本発明の着色組成物は、硬化性基を有する化合物を含有する。硬化性基を有する化合物が硬化する際の反応機構については特に限定されない。ラジカル重合反応、カチオン重合反応、縮重合反応、求核付加反応、置換反応による架橋反応等が挙げられる。硬化性基を有する化合物は、ラジカル重合反応により硬化する化合物であることが好ましい。硬化性基としては、エチレン性不飽和基、エポキシ基などが挙げられる。エチレン性不飽和基としては、ビニル基、ビニロキシ基、アリル基、メタリル基、(メタ)アクリロイル基、スチレン基、シンナモイル基およびマレイミド基が挙げられ、(メタ)アクリロイル基、スチレン基、マレイミド基が好ましく、(メタ)アクリロイル基がより好ましい。 << Compound with curable group >>
The coloring composition of the present invention contains a compound having a curable group. The reaction mechanism when the compound having a curable group is cured is not particularly limited. Examples thereof include radical polymerization reaction, cationic polymerization reaction, polycondensation reaction, nucleophilic addition reaction, and cross-linking reaction by substitution reaction. The compound having a curable group is preferably a compound that is cured by a radical polymerization reaction. Examples of the curable group include an ethylenically unsaturated group and an epoxy group. Examples of the ethylenically unsaturated group include a vinyl group, a vinyloxy group, an allyl group, a metallicyl group, a (meth) acryloyl group, a styrene group, a cinnamoyl group and a maleimide group, and a (meth) acryloyl group, a styrene group and a maleimide group. Preferably, a (meth) acryloyl group is more preferred.
本発明において、硬化性化合物として用いられるエチレン性不飽和基を有する化合物としては、モノマーであってもよく、樹脂であってもよい。耐熱性に優れた硬化膜を形成しやすいという理由から樹脂タイプの化合物を含むことが好ましい。以下、エチレン性不飽和基を有する化合物を重合性化合物ともいう。また、エチレン性不飽和基を有するモノマーを重合性モノマーともいう。また、エチレン性不飽和基を有する樹脂を重合性樹脂ともいう。 (Compound having an ethylenically unsaturated group)
In the present invention, the compound having an ethylenically unsaturated group used as the curable compound may be a monomer or a resin. It is preferable to contain a resin type compound because it is easy to form a cured film having excellent heat resistance. Hereinafter, the compound having an ethylenically unsaturated group is also referred to as a polymerizable compound. Further, a monomer having an ethylenically unsaturated group is also referred to as a polymerizable monomer. Further, a resin having an ethylenically unsaturated group is also referred to as a polymerizable resin.
重合性樹脂のC=C価[mmol/g]=(低分子成分(a)の含有量[ppm]/低分子成分(a)の分子量[g/mol])/(重合性樹脂の秤量値[g]×(重合性樹脂液の固形分濃度[質量%]/100)×10) The ethylenically unsaturated base value (hereinafter, also referred to as C = C value) of the polymerizable resin is preferably 0.05 to 5.0 mmol / g. The upper limit is more preferably 4.0 mmol / g or less, further preferably 3.0 mmol / g or less, further preferably 2.0 mmol / g or less, and 1.0 mmol / g or less. It is particularly preferable to have. The lower limit is preferably 0.1 mmol / g or more, and more preferably 0.2 mmol / g or more. The C = C value of the polymerizable resin is a numerical value representing the molar amount of ethylenically unsaturated groups per 1 g of the solid content of the polymerizable resin. The C = C value of the polymerizable resin is determined by extracting the low molecular weight component (a) of the ethylenically unsaturated group moiety from the polymerizable resin by alkaline treatment and measuring the content thereof by high performance liquid chromatography (HPLC). It can be calculated from. When the ethylenically unsaturated group site cannot be extracted from the polymerizable resin by alkaline treatment, the value measured by the NMR method (nuclear magnetic resonance) is used.
C = C value [mmol / g] = (content of low molecular weight component (a) [ppm] / molecular weight of low molecular weight component (a) [g / mol]) / (weighed value of polymerizable resin) [G] x (solid content concentration of the polymerizable resin solution [mass%] / 100) x 10)
上記式において、RG3は、水素原子またはメチル基を表す。
上記式において、QG1は、-O-または-NH-を表し、LG1は、単結合または2価の連結基を表す。2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アルキレンオキシ基(好ましくは炭素数1~12のアルキレンオキシ基)、オキシアルキレンカルボニル基(好ましくは炭素数1~12のオキシアルキレンカルボニル基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、OCO-、-S-およびこれらの2以上を組み合わせてなる基が挙げられる。
RG4は、水素原子または置換基を表す。置換基としては、アルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルキルチオエーテル基、アリールチオエーテル基、ヘテロアリールチオエーテル基等が挙げられる。 In the above formula, RG1 and RG2 each represent an alkylene group. It is not particularly restricted but includes alkylene groups represented by R G1 and R G2, preferably a linear or branched alkylene group of 1 to 20 carbon atoms, having 2 to 16 carbon atoms linear or branched alkylene A group is more preferable, and a linear or branched alkylene group having 3 to 12 carbon atoms is further preferable.
In the above formula, RG3 represents a hydrogen atom or a methyl group.
In the above formula, Q G1 represents -O- or -NH-, and LG 1 represents a single bond or a divalent linking group. The divalent linking group includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), and an oxyalkylenecarbonyl group (preferably 1 to 12 carbon atoms). ~ 12 oxyalkylene carbonyl groups), arylene groups (preferably arylene groups with 6 to 20 carbon atoms), -NH-, -SO-, -SO 2- , -CO-, -O-, -COO-, OCO -, -S- and groups consisting of a combination of two or more of these can be mentioned.
RG4 represents a hydrogen atom or a substituent. Examples of the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
Y1およびY2は、それぞれ独立して単結合または連結基を表し、
A1は顔料吸着部を含む基を表し、
P1はポリマー鎖を表し、
nは1~20を表し、mは1~20を表し、m+nは3~21であり、
n個のY1およびA1はそれぞれ同一であってもよく、異なっていてもよく、
m個のY2およびP1はそれぞれ同一であってもよく、異なっていてもよく、
Z1、A1およびP1の少なくとも一つはエチレン性不飽和基を表す。
性基を含む。 In the present invention, as the polymerizable resin, a compound represented by the following formula (SP-1) (hereinafter, also referred to as compound (SP-1)) can be used. Compound (SP-1) can be preferably used as a dispersant.
Y 1 and Y 2 independently represent a single bond or a linking group, respectively.
A 1 represents a group containing a pigment adsorbing portion.
P 1 represents a polymer chain
n represents 1 to 20, m represents 1 to 20, m + n represents 3 to 21, and so on.
Each of n Y 1 and A 1 may be the same or different,
The m Y 2 and P 1 may be the same or different, respectively.
At least one of Z 1 , A 1 and P 1 represents an ethylenically unsaturated group.
Includes sex groups.
上記式において、RG3は、水素原子またはメチル基を表す。
上記式において、QG1は、-O-または-NH-を表し、LG1は、単結合またはアリーレン基を表し、LG2は、単結合または2価の連結基を表す。QG1は、-O-であることが好ましい。LG1は、単結合であることが好ましい。LG2が表す2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、-OCO-、-S-、-NHCO-、-CONH-、およびこれらの2以上を組み合わせてなる基が挙げられる。
RG4は、水素原子または置換基を表す。置換基としては、アルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルキルチオエーテル基、アリールチオエーテル基、ヘテロアリールチオエーテル基、エチレン性不飽和基、酸基等が挙げられる。 In the above formula, RG1 and RG2 each represent an alkylene group. The alkylene group represented by R G1 and R G2, preferably a linear or branched alkylene group of 1 to 20 carbon atoms, more preferably a linear or branched alkylene group having 2 to 16 carbon atoms , A linear or branched alkylene group having 3 to 12 carbon atoms is more preferable. The alkylene group may have a substituent. Examples of the substituent include an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, and ethylenically unsaturated groups.
In the above formula, RG3 represents a hydrogen atom or a methyl group.
In the above formula, Q G1 represents -O- or -NH-, LG 1 represents a single bond or an arylene group, and LG 2 represents a single bond or a divalent linking group. Q G1 is preferably —O—. LG1 is preferably a single bond. Examples of the divalent linking group represented by LG2 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-. -SO 2 -, - CO -, - O -, - COO -, - OCO -, - S -, - NHCO -, - CONH-, and include a group formed by combining two or more of these.
RG4 represents a hydrogen atom or a substituent. Examples of the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, an ethylenically unsaturated group, an acid group and the like. Can be mentioned.
本発明において、硬化性化合物として用いられるエポキシ基を有する化合物(以下、エポキシ化合物ともいう)としては、1分子内にエポキシ基を2個以上有する化合物が好ましく用いられる。エポキシ化合物のエポキシ基の数の上限は、100個以下であることが好ましく、10個以下であることがより好ましく、5個以下であることが更に好ましい。 (Compound with epoxy group)
In the present invention, as a compound having an epoxy group used as a curable compound (hereinafter, also referred to as an epoxy compound), a compound having two or more epoxy groups in one molecule is preferably used. The upper limit of the number of epoxy groups in the epoxy compound is preferably 100 or less, more preferably 10 or less, and further preferably 5 or less.
また、硬化性化合物として重合性モノマーを用いる場合、重合性モノマーの含有量は、着色組成物の全固形分中0.1~40質量%であることが好ましい。下限は1質量%以上であることが好ましく、2質量%以上であることがより好ましい。上限は、30質量%以下であることが好ましく、20質量%以下であることがより好ましく、10質量%以下であることが更に好ましい。
また、硬化性化合物として重合性樹脂を用いる場合、重合性樹脂の含有量は、着色組成物の全固形分中1~50質量%であることが好ましい。下限は3質量%以上であることが好ましく、5質量%以上であることがより好ましく、10質量%以上であることが更に好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。
また、重合性モノマーと重合性樹脂との合計の含有量は着色組成物の全固形分中1~50質量%であることが好ましい。下限は3質量%以上であることが好ましく、5質量%以上であることがより好ましく、10質量%以上であることが更に好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。また、重合性モノマーと重合性樹脂との合計量中における、重合性樹脂の含有量は70質量%以上であることが好ましく、80質量%以上であることがより好ましい。
また、硬化性化合物としてエポキシ化合物を用いる場合、エポキシ化合物の含有量は、着色組成物の全固形分中0.1~40質量%が好ましい。下限は、例えば1質量%以上がより好ましく、2質量%以上が更に好ましい。上限は、例えば、30質量%以下がより好ましく、20質量%以下が更に好ましい。エポキシ化合物は、1種単独であってもよいし、2種以上を併用してもよい。また、重合性化合物と、エポキシ基を有する化合物とを併用する場合、両者の割合(質量比)は、重合性化合物の質量:エポキシ基を有する化合物の質量=100:1~100:400が好ましく、100:1~100:100がより好ましく、100:1~100:50がさらに好ましい。 The content of the curable compound is preferably 1 to 50% by mass based on the total solid content of the coloring composition. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
When a polymerizable monomer is used as the curable compound, the content of the polymerizable monomer is preferably 0.1 to 40% by mass in the total solid content of the coloring composition. The lower limit is preferably 1% by mass or more, and more preferably 2% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 20% by mass or less, and further preferably 10% by mass or less.
When a polymerizable resin is used as the curable compound, the content of the polymerizable resin is preferably 1 to 50% by mass in the total solid content of the coloring composition. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
The total content of the polymerizable monomer and the polymerizable resin is preferably 1 to 50% by mass in the total solid content of the coloring composition. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less. Further, the content of the polymerizable resin in the total amount of the polymerizable monomer and the polymerizable resin is preferably 70% by mass or more, and more preferably 80% by mass or more.
When an epoxy compound is used as the curable compound, the content of the epoxy compound is preferably 0.1 to 40% by mass based on the total solid content of the coloring composition. The lower limit is, for example, more preferably 1% by mass or more, further preferably 2% by mass or more. The upper limit is, for example, more preferably 30% by mass or less, further preferably 20% by mass or less. The epoxy compound may be used alone or in combination of two or more. When the polymerizable compound and the compound having an epoxy group are used in combination, the ratio (mass ratio) of the two is preferably mass of the polymerizable compound: mass of the compound having an epoxy group = 100: 1 to 100: 400. , 100: 1 to 100: 100 is more preferable, and 100: 1 to 100: 50 is even more preferable.
着色組成物が、エチレン性不飽和基を有するモノマー(重合性モノマー)と、樹脂とを含み、
着色組成物に含まれるエチレン性不飽和基を有するモノマー(重合性モノマー)の質量M1と、着色組成物に含まれる樹脂の質量B1との比であるM1/B1が0.35以下であり、好ましくは0.25以下であり、より好ましくは0.21以下である態様。この態様の着色組成物によれば、より耐熱性に優れた硬化膜を形成することができる。更には硬化膜形成時における膜収縮を抑制することもできる。特に、樹脂として重合性樹脂を含む用いた場合においては上記の効果がより顕著に得られる。上記のM1/B1の値の下限は0.01以上であることが好ましく、0.04以上であることがより好ましく、0.07以上であることが更に好ましい。なお、樹脂の質量B1とは、上述した重合性樹脂と後述する他の樹脂との合計量である。着色組成物が他の樹脂を含まない場合、樹脂の質量B1は上述した重合性樹脂の質量である。また、着色組成物が重合性樹脂を含まない場合、樹脂の質量B1は他の樹脂の質量である。
また、上記の態様において、重合性モノマーと樹脂との合計の含有量は着色組成物の全固形分中1~50質量%であることが好ましい。下限は3質量%以上であることが好ましく、5質量%以上であることがより好ましく、10質量%以上であることが更に好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。 The following is mentioned as a preferable aspect of the coloring composition of this invention.
The coloring composition contains a monomer having an ethylenically unsaturated group (polymerizable monomer) and a resin.
M 1 / B 1, which is the ratio of the mass M 1 of the monomer having an ethylenically unsaturated group (polymerizable monomer) contained in the coloring composition to the mass B 1 of the resin contained in the coloring composition, is 0.35. The embodiment is as follows, preferably 0.25 or less, and more preferably 0.21 or less. According to the coloring composition of this aspect, a cured film having more excellent heat resistance can be formed. Further, it is possible to suppress the film shrinkage at the time of forming the cured film. In particular, when a polymerizable resin is used as the resin, the above effect can be obtained more remarkably. The lower limit of the value of M 1 / B 1 is preferably 0.01 or more, more preferably 0.04 or more, and further preferably 0.07 or more. The mass B 1 of the resin is the total amount of the above-mentioned polymerizable resin and the other resin described later. When the coloring composition does not contain other resins, the mass B 1 of the resin is the mass of the above-mentioned polymerizable resin. When the coloring composition does not contain a polymerizable resin, the mass B 1 of the resin is the mass of another resin.
Further, in the above aspect, the total content of the polymerizable monomer and the resin is preferably 1 to 50% by mass in the total solid content of the coloring composition. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
本発明の着色組成物は、硬化性基を含まない樹脂(以下、他の樹脂ともいう)をさらに含有することができる。他の樹脂は、例えば、顔料などの粒子を組成物中で分散させる用途やバインダーの用途で配合される。なお、主に顔料などの粒子を分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外の目的で樹脂を使用することもできる。 << Other resins >>
The coloring composition of the present invention can further contain a resin containing no curable group (hereinafter, also referred to as another resin). Other resins are blended, for example, for the purpose of dispersing particles such as pigments in the composition and for the purpose of binders. A resin mainly used for dispersing particles such as pigments is also referred to as a dispersant. However, such an application of the resin is an example, and the resin can be used for a purpose other than such an application.
また、上述した硬化性化合物と他の樹脂との合計の含有量は、本発明の着色組成物の全固形分中1~50質量%であることが好ましい。下限は3質量%以上であることが好ましく、5質量%以上であることがより好ましく、10質量%以上であることが更に好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。 When the coloring composition of the present invention contains another resin, the content of the other resin is preferably 30% by mass or less, preferably 20% by mass or less, based on the total solid content of the coloring composition of the present invention. Is more preferable, and 10% by mass or less is further preferable.
Moreover, the total content of the above-mentioned curable compound and other resins is preferably 1 to 50% by mass in the total solid content of the coloring composition of the present invention. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
本発明の着色組成物は光重合開始剤を含むことが好ましい。特に、硬化性化合物としてエチレン性不飽和基を有する化合物を用いた場合には、本発明の着色組成物はさらに光重合開始剤を含むことが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。 << Photopolymerization Initiator >>
The coloring composition of the present invention preferably contains a photopolymerization initiator. In particular, when a compound having an ethylenically unsaturated group is used as the curable compound, the coloring composition of the present invention preferably further contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable. The photopolymerization initiator is preferably a photoradical polymerization initiator.
本発明の着色組成物は顔料誘導体を含有することができる。顔料誘導体としては、顔料の一部を、酸基、または塩基性基で置換した構造を有する化合物が挙げられる。顔料誘導体としては、特開昭56-118462号公報、特開昭63-264674号公報、特開平01-217077号公報、特開平03-009961号公報、特開平03-026767号公報、特開平03-153780号公報、特開平03-045662号公報、特開平04-285669号公報、特開平06-145546号公報、特開平06-212088号公報、特開平06-240158号公報、特開平10-030063号公報、特開平10-195326号公報、国際公開第2011/024896号の段落番号0086~0098、国際公開第2012/102399号の段落番号0063~0094、国際公開第2017/038252号の段落番号0082、特開2015-151530号公報の段落番号0171等に記載の化合物、特開2015-172732号公報に記載の化合物、特開2014-199308号公報に記載の化合物、特開2014-085562号公報に記載の化合物、特開2014-035351号公報に記載の化合物、特開2008-081565号公報に記載の化合物を用いることができ、この内容は本明細書に組み込まれる。 << Pigment derivative >>
The coloring composition of the present invention can contain a pigment derivative. Examples of the pigment derivative include compounds having a structure in which a part of the pigment is replaced with an acid group or a basic group. Examples of the pigment derivative include JP-A-56-118462, JP-A-63-264674, JP-A-01-217777, JP-A-03-009961, JP-A-03-026767, and JP-A-03. -153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063 No. 10, Japanese Patent Application Laid-Open No. 10-195326, paragraph numbers 0083 to 0998 of International Publication No. 2011/024896, paragraph numbers 0063 to 0094 of International Publication No. 2012/102399, paragraph number 0082 of International Publication No. 2017/038252. , The compound described in paragraph No. 0171 of JP-A-2015-151530, the compound described in JP-A-2015-172732, the compound described in JP-A-2014-199308, and JP-A-2014-0855662. The compound described, the compound described in JP-A-2014-035351, and the compound described in JP-A-2008-081565 can be used, and the contents thereof are incorporated in the present specification.
本発明の着色組成物はシランカップリング剤を含有することができる。この態様によれば、得られる硬化膜の支持体との密着性を向上させることができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。 << Silane Coupling Agent >>
The coloring composition of the present invention can contain a silane coupling agent. According to this aspect, the adhesion of the obtained cured film to the support can be improved. In the present invention, the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups. Further, the hydrolyzable group means a substituent which is directly bonded to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group, and isocyanate group. , A phenyl group and the like, preferably an amino group, a (meth) acryloyl group and an epoxy group. Specific examples of the silane coupling agent include the compounds described in JP-A 2009-288703, paragraphs 0018 to 0036, and the compounds described in JP-A 2009-242604, paragraphs 0056 to 0066. Are incorporated herein by reference.
本発明の着色組成物は、溶剤を含有することができる。溶剤としては、有機溶剤が挙げられる。溶剤は、各成分の溶解性や着色組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤を好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、シクロヘキサノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミドなどが挙げられる。ただし溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。 << Solvent >>
The coloring composition of the present invention can contain a solvent. Examples of the solvent include organic solvents. The solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the coloring composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like. For these details, paragraph number 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein. Further, an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-dimethylpropanamide and the like. However, it may be better to reduce aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as a solvent for environmental reasons (for example, 50 mass ppm (parts per) with respect to the total amount of the organic solvent. It can be milion) or less, can be 10 mass ppm or less, or can be 1 mass ppm or less).
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。 << Polymerization inhibitor >>
The coloring composition of the present invention can contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。 << Surfactant >>
The coloring composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used. As for the surfactant, the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤は、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などを用いることができる。このような化合物としては、特開2009-217221号公報の段落番号0038~0052、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤として特許第6268967号公報の段落番号0049~0059に記載の化合物も使用できる。 << UV absorber >>
The coloring composition of the present invention can contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used. Examples of such a compound include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-068814. Examples include the compounds described in paragraphs 0061 to 0080 of JP 2016-162946, the contents of which are incorporated herein. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.). Examples of the benzotriazole compound include MYUA series manufactured by Miyoshi Oil & Fats (Chemical Industry Daily, February 1, 2016). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物を使用することもできる。 << Antioxidant >>
The coloring composition of the present invention can contain an antioxidant. Examples of the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like. As the phenol compound, any phenol compound known as a phenolic antioxidant can be used. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable. As the above-mentioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable. Further, as the antioxidant, a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used. As a phosphorus-based antioxidant, tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosfepine-6 -Il] oxy] ethyl] amine, tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like. Commercially available antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like. The antioxidants include the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in International Publication No. 2017/006600, and the compounds described in International Publication No. 2017/164024. It can also be used.
本発明の着色組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本発明の着色組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。また、特開2018-155881号公報に記載されているように、C.I.ピグメントイエロー129を耐候性改良の目的で添加しても良い。 << Other ingredients >>
The coloring compositions of the present invention, as required, include sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, etc.). It may contain a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension modifier, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074. The description such as the numbers 0101 to 0104 and 0107 to 0109 can be referred to, and the contents thereof are incorporated in the present specification. In addition, the coloring composition of the present invention may contain a latent antioxidant, if necessary. The latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. As a result, a compound in which the protecting group is eliminated and functions as an antioxidant can be mentioned. Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219. Commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like. Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
本発明の着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や着色組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、着色組成物の内壁は、容器内壁からの金属溶出を防ぎ、組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。本発明の着色組成物の保存条件としては特に限定はなく、従来公知の方法を用いることができる。また、特開2016-180058号公報に記載された方法を用いることもできる。 <Container>
The container for the colored composition of the present invention is not particularly limited, and a known container can be used. In addition, as a storage container, a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used for the purpose of suppressing impurities from being mixed into raw materials and coloring compositions. It is also preferable to use. Examples of such a container include the container described in JP-A-2015-123351. Further, the inner wall of the coloring composition is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the composition, and suppressing the alteration of components. The storage conditions for the coloring composition of the present invention are not particularly limited, and conventionally known methods can be used. Further, the method described in JP-A-2016-180058 can also be used.
本発明の着色組成物は、前述の成分を混合して製造できる。着色組成物の製造に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を製造してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を製造してもよい。 <Manufacturing method of coloring composition>
The coloring composition of the present invention can be produced by mixing the above-mentioned components. In the production of the coloring composition, all the components may be simultaneously dissolved and / or dispersed in a solvent to produce the coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to produce a coloring composition.
本発明の硬化膜は、上述した本発明の着色組成物から得られる硬化膜である。本発明の硬化膜は、カラーフィルタなどに用いることができる。具体的には、カラーフィルタの着色層(画素)として好ましく用いることができ、より具体的には、カラーフィルタの赤色着色層(赤色画素)として好ましく用いることができる。本発明の硬化膜の膜厚は、目的に応じて適宜調整できる。例えば、膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下がさらに好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上がさらに好ましい。 <Cured film>
The cured film of the present invention is a cured film obtained from the above-mentioned coloring composition of the present invention. The cured film of the present invention can be used as a color filter or the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a red colored layer (red pixel) of a color filter. The film thickness of the cured film of the present invention can be appropriately adjusted according to the intended purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and further preferably 0.3 μm or more.
次に、本発明のカラーフィルタについて説明する。本発明のカラーフィルタは、上述した本発明の硬化膜を有する。より好ましくは、カラーフィルタの画素として、本発明の硬化膜を有する。本発明のカラーフィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。 <Color filter>
Next, the color filter of the present invention will be described. The color filter of the present invention has the cured film of the present invention described above. More preferably, it has the cured film of the present invention as the pixels of the color filter. The color filter of the present invention can be used for a solid-state image sensor such as a CCD (charge coupling element) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
次に、本発明のカラーフィルタの製造方法について説明する。本発明のカラーフィルタは、上述した本発明の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を経て製造できる。 <Method of manufacturing color filter>
Next, a method for manufacturing the color filter of the present invention will be described. The color filter of the present invention forms a pattern on the colored composition layer by a step of forming a colored composition layer on a support using the colored composition of the present invention described above and a photolithography method or a dry etching method. It can be manufactured through the process of
まず、フォトリソグラフィ法によりパターンを形成してカラーフィルタを製造する場合について説明する。フォトリソグラフィ法によるパターン形成は、本発明の着色組成物を用いて支持体上に着色組成物層を形成する工程と、着色組成物層をパターン状に露光する工程と、着色組成物層の未露光部を現像除去してパターン(画素)を形成する工程と、を含むことが好ましい。必要に応じて、着色組成物層をベークする工程(プリベーク工程)、および、現像されたパターン(画素)をベークする工程(ポストベーク工程)を設けてもよい。 (Photolithography method)
First, a case where a pattern is formed by a photolithography method to manufacture a color filter will be described. Pattern formation by the photolithography method includes a step of forming a coloring composition layer on a support using the coloring composition of the present invention, a step of exposing the coloring composition layer in a pattern, and a step of exposing the coloring composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
次に、着色組成物層をパターン状に露光する(露光工程)。例えば、着色組成物層に対し、ステッパー露光機やスキャナ露光機などを用いて、所定のマスクパターンを有するマスクを介して露光することで、パターン状に露光することができる。これにより、露光部分を硬化することができる。 << Exposure process >>
Next, the coloring composition layer is exposed in a pattern (exposure step). For example, the colored composition layer can be exposed in a pattern by exposing the colored composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
次に、ドライエッチング法によりパターンを形成してカラーフィルタを製造する場合について説明する。ドライエッチング法でのパターン形成は、本発明の着色組成物を用いて支持体上に着色組成物層を形成し、この着色組成物層の全体を硬化させて硬化物層を形成する工程と、この硬化物層上にフォトレジスト層を形成する工程と、フォトレジスト層をパターン状に露光したのち、現像してレジストパターンを形成する工程と、このレジストパターンをマスクとして硬化物層に対してエッチングガスを用いてドライエッチングする工程と、を含むことが好ましい。フォトレジスト層の形成においては、更にプリベーク処理を施すことが好ましい。特に、フォトレジスト層の形成プロセスとしては、露光後の加熱処理、現像後の加熱処理(ポストベーク処理)を実施する形態が望ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落番号0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。 (Dry etching method)
Next, a case where a pattern is formed by a dry etching method to manufacture a color filter will be described. Pattern formation by the dry etching method includes a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer. A step of forming a photoresist layer on the cured product layer, a step of exposing the photoresist layer in a pattern and then developing to form a resist pattern, and etching the cured product layer using this resist pattern as a mask. It is preferable to include a step of dry etching with a gas. In forming the photoresist layer, it is preferable to further perform a prebaking treatment. In particular, as the process for forming the photoresist layer, it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development. Regarding the pattern formation by the dry etching method, the description in paragraphs 0010 to 0067 of JP2013-064993A can be referred to, and this content is incorporated in the present specification.
本発明の固体撮像素子は、上述した本発明の硬化膜を有する。本発明の固体撮像素子の構成としては、本発明の硬化膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。 <Solid image sensor>
The solid-state imaging device of the present invention has the cured film of the present invention described above. The configuration of the solid-state image sensor of the present invention is not particularly limited as long as it includes the cured film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
本発明の画像表示装置は、上述した本発明の硬化膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。 <Image display device>
The image display device of the present invention has the cured film of the present invention described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. For details on the definition of image display devices and the details of each image display device, see, for example, "Electronic Display Device (Akio Sasaki, Kogyo Chosakai Co., Ltd., published in 1990)", "Display Device (by Junaki Ibuki, Industrial Books)" Co., Ltd. (issued in 1989) ”. The liquid crystal display device is described in, for example, "Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Institute Co., Ltd., published in 1994)". The liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
樹脂およびマクロモノマーの重量平均分子量(Mw)および数平均分子量(Mn)は、下記測定条件の下、GPC(ゲルパーミエーションクロマトグラフィ)測定により算出した。
装置:HLC-8220GPC(東ソー(株)製)
検出器:示差屈折計(RI検出器)
プレカラム TSKGUARDCOLUMN MP(XL)6mm×40mm(東ソー(株)製)
サンプル側カラム:以下4本を直結〔全て東ソー(株)製〕
TSK-GEL Multipore-HXL-M 7.8mm×300mm
リファレンス側カラム:サンプル側カラムに同じ
恒温槽温度:40℃
移動相:テトラヒドロフラン
サンプル側移動相流量:1.0mL/分
リファレンス側移動相流量:0.3mL/分
試料濃度:0.1質量%
試料注入量:100μL
データ採取時間:試料注入後16分~46分
サンプリングピッチ:300ms(ミリ秒) <Measurement method of weight average molecular weight (Mw) and number average molecular weight (Mn)>
The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin and the macromonomer were calculated by GPC (gel permeation chromatography) measurement under the following measurement conditions.
Equipment: HLC-8220GPC (manufactured by Tosoh Corporation)
Detector: Differential refractometer (RI detector)
Pre-column TSKGUARD COLUMN MP (XL) 6 mm x 40 mm (manufactured by Tosoh Corporation)
Sample side column: The following 4 columns are directly connected [all manufactured by Tosoh Corporation]
TSK-GEL Multipore-HXL-M 7.8mm x 300mm
Reference side column: Same as sample side column Constant temperature bath temperature: 40 ° C
Mobile phase: tetrahydrofuran Sample side mobile phase flow rate: 1.0 mL / min Reference side mobile phase flow rate: 0.3 mL / min Sample concentration: 0.1% by mass
Sample injection volume: 100 μL
Data collection time: 16 to 46 minutes after sample injection Sampling pitch: 300 ms (milliseconds)
樹脂の酸価は水酸化ナトリウム水溶液を用いた中和滴定により求めた。具体的には、樹脂を溶媒に溶解させた溶液に、電位差測定法を用いて水酸化ナトリウム水溶液で滴定し、樹脂の固形分1gに含まれる酸のミリモル数を算出し、次に、その値を水酸化カリウム(KOH)の分子量56.1をかけることにより求めた。 <Measurement method of acid value>
The acid value of the resin was determined by neutralization titration using an aqueous sodium hydroxide solution. Specifically, the solution in which the resin is dissolved in a solvent is titrated with an aqueous solution of sodium hydroxide using a potential difference measurement method to calculate the number of millimoles of the acid contained in 1 g of the solid content of the resin, and then the value thereof. Was determined by multiplying the molecular weight of potassium hydroxide (KOH) by 56.1.
下記方法により、樹脂のC=C価を測定した。
アルカリ処理によって樹脂からエチレン性不飽和基部位の低分子成分(a)を取り出し、その含有量を高速液体クロマトグラフィー(HPLC)により測定し、その測定値に基づいて下記式からC=C価を算出した。
具体的には、樹脂0.1gをテトラヒドロフラン/メタノール混合液(50mL/15mL)に溶解させ、4mol/L水酸化ナトリウム水溶液10mLを加え、40℃で2時間反応させた。反応液を4mol/Lメタンスルホン酸水溶液10.2mLで中和し、その後、イオン交換水5mLとメタノール2mLを加えた混合液を100mLメスフラスコに移液し、メタノールでメスアップすることでHPLC測定サンプルを調製し、以下の条件で測定する。なお、低分子成分(a)の含有量は別途作成した低分子成分(a)の検量線から算出し、C=C価は下記式より算出した。 <Measurement method of C = C value (ethylenically unsaturated base value)>
The C = C valence of the resin was measured by the following method.
The low molecular weight component (a) of the ethylenically unsaturated group moiety is extracted from the resin by alkaline treatment, the content thereof is measured by high performance liquid chromatography (HPLC), and the C = C value is calculated from the following formula based on the measured value. Calculated.
Specifically, 0.1 g of the resin was dissolved in a mixed solution of tetrahydrofuran / methanol (50 mL / 15 mL), 10 mL of a 4 mol / L sodium hydroxide aqueous solution was added, and the mixture was reacted at 40 ° C. for 2 hours. The reaction solution was neutralized with 10.2 mL of a 4 mol / L methanesulfonic acid aqueous solution, and then a mixed solution containing 5 mL of ion-exchanged water and 2 mL of methanol was transferred to a 100 mL volumetric flask, and the mixture was pipette-up with methanol for HPLC measurement. Prepare a sample and measure under the following conditions. The content of the low molecular weight component (a) was calculated from the calibration curve of the low molecular weight component (a) prepared separately, and the C = C valence was calculated by the following formula.
測定機器: Agilent-1200(アジレント・テクノロジー(株)製)
カラム: Phenomenex社製 Synergi 4u Polar-RP 80A,250mm×4.60mm(内径)+ガードカラム
カラム温度:40℃
分析時間:15分
流速:1.0mL/min(最大送液圧力:182bar(18.2MPa))
注入量:5μl
検出波長:210nm
溶離液:テトラヒドロフラン(安定剤不含HPLC用)/バッファー溶液(リン酸0.2体積%及びトリエチルアミン0.2体積%を含有するイオン交換水溶液)=55/45(体積%)
なお、本明細書において、体積%は25℃における値である。 -HPLC measurement conditions-
Measuring equipment: Agilent-1200 (manufactured by Agilent Technologies)
Column: Synergy 4u Polar-RP 80A manufactured by Phenomenex, 250 mm x 4.60 mm (inner diameter) + guard column Column temperature: 40 ° C.
Analysis time: 15 minutes Flow rate: 1.0 mL / min (maximum liquid delivery pressure: 182 bar (18.2 MPa))
Injection volume: 5 μl
Detection wavelength: 210 nm
Eluent: Tetrahydrofuran (for HPLC without stabilizer) / buffer solution (ion exchange aqueous solution containing 0.2% by volume of phosphoric acid and 0.2% by volume of triethylamine) = 55/45 (% by volume)
In addition, in this specification, volume% is a value at 25 degreeC.
樹脂約0.5gを精密に量り、酢酸(100質量%)50mLを加えて溶かし、0.1 mol/L 過塩素酸で電気滴定法(電位差滴定)電位差自動滴定装置(AT-710M;京都電子工業(株)製)を用いて滴定した。また、同様の方法で空試験を行って補正した。
アミン価=a×5.611/c
a:0.1mol/L 過塩素酸の消費量(mL)
c:樹脂の量(g) <Measuring method of amine value>
Weigh accurately about 0.5 g of resin, add 50 mL of acetic acid (100% by mass) to dissolve it, and use 0.1 mol / L perchloric acid for electric titration (potentiometric titration). Potentiometric titration device (AT-710M; Kyoto Electronics) Titrated using (manufactured by Kogyo Co., Ltd.). In addition, a blank test was performed in the same manner to make corrections.
Amine value = a × 5.611 / c
a: 0.1 mol / L Perchloric acid consumption (mL)
c: Amount of resin (g)
下記の表に記載の原料を混合して混合液を得た。得られた混合液を、循環型分散装置(ビーズミル)として寿工業株式会社製のウルトラアペックスミル(商品名)を用いて分散処理を行い、各顔料分散液を調製した。下記表に記載の成分のうち、分散剤1および分散剤2の質量部の欄に記載の数値は、固形分の値である。
The raw materials listed in the table below were mixed to obtain a mixed solution. The obtained mixed solution was subjected to dispersion treatment using an Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulating dispersion device (bead mill) to prepare each pigment dispersion. Among the components listed in the table below, the numerical values described in the column of parts by mass of the dispersant 1 and the dispersant 2 are the values of the solid content.
下記の表に記載の原料を混合してマゼンタ色着色剤溶液MD1~MD33を得た。
The raw materials listed in the table below were mixed to obtain magenta colorant solutions MD1 to MD33.
下記の表に記載の原料を混合して混合液を得た。得られた混合液を、循環型分散装置(ビーズミル)として寿工業株式会社製のウルトラアペックスミル(商品名)を用いて分散処理を行い、マゼンタ色着色剤溶液CMD1~CMD2を調製した。下記表に記載の成分のうち、分散剤の質量部の欄に記載の数値は、固形分の値である。
The raw materials listed in the table below were mixed to obtain a mixed solution. The obtained mixed solution was subjected to dispersion treatment using an Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulation type disperser (bead mill) to prepare magenta colorant solutions CMD1 to CMD2. Among the components listed in the table below, the numerical value described in the column of the mass part of the dispersant is the value of the solid content.
(顔料)
顔料R1~R5:下記構造の化合物。顔料R1はC.I.ピグメントレッド272である。
顔料Y2:C.I.ピグメントイエロー139
顔料Y3:C.I.ピグメントイエロー150
顔料Y4:C.I.ピグメントイエロー185 The materials listed in the above table are as follows.
(Pigment)
Pigments R1 to R5: Compounds with the following structure. Pigment R1 is C.I. I. Pigment Red 272.
Pigment Y2: C.I. I. Pigment Yellow 139
Pigment Y3: C.I. I. Pigment Yellow 150
Pigment Y4: C.I. I. Pigment Yellow 185
マゼンタ色染料M1~M32:下記表に記載のカチオン性シアニン発色団とアニオンとの塩。マゼンタ色染料M1~M32は、いずれも23℃の水100gに対する溶解度、または、23℃のプロピレングリコールモノメチルエーテルアセテート100gに対する溶解度が、1g以上である。
Magenta Dyes M1-M32: Salts of cationic cyanine chromophores and anions listed in the table below. The magenta color dyes M1 to M32 have a solubility in 100 g of water at 23 ° C. or a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C. of 1 g or more.
以下の構造式中、Etはエチル基を表し、Prはプロピル基を表し、Buはブチル基を表し、Hexはヘキシル基を表す。
In the following structural formula, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, and Hex represents a hexyl group.
マゼンタ色顔料CM1:C.I.ピグメントレッド122
マゼンタ色顔料CM2:C.I.ピグメントレッド177
マゼンタ色顔料CM1およびマゼンタ色顔料CM2は、いずれも23℃の水100gに対する溶解度および23℃のプロピレングリコールモノメチルエーテルアセテート100gに対する溶解度がいずれも0.1g未満である。 (Magenta color pigment)
Magenta color pigment CM1: C.I. I. Pigment Red 122
Magenta color pigment CM2: C.I. I. Pigment Red 177
Both the magenta color pigment CM1 and the magenta color pigment CM2 have a solubility in 100 g of water at 23 ° C. and a solubility in 100 g of propylene glycol monomethyl ether acetate at 23 ° C. of less than 0.1 g.
顔料誘導体Sy1:下記構造の化合物
Pigment derivative Sy1: Compound with the following structure
分散剤D1:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw:20000、C=C価:0.0mmol/g、酸価:75mgKOH/g、アミン価:0.0mmol/g)
Dispersant D1: Resin having the following structure (the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units. Mw: 20000, C = C value: 0.0 mmol / g, Acid value: 75 mgKOH / g, amine value: 0.0 mmol / g)
三口フラスコに、濃度(固形分含有量)が50質量%のマクロモノマーB-1溶液の60.78g(PGMEA:30.39g、マクロモノマーB-1(30.39g))、ω-カルボキシ-ポリカプロラクトンモノアクリレート(アロニックスM-5300、東亞合成(株)製)の50.99g、PGMEA(プロピレングリコール1-モノメチルエーテル2-アセタートの159.5gを導入し、混合物を得た。
窒素を吹き込みながら、上記混合物を撹拌した。次に、窒素をフラスコ内に流しながら、混合物を75℃まで昇温した。次に、混合物に、ドデシルメルカプタンの0.82g、次いで、2,2’-アゾビス(2-メチルプロピオン酸メチル)(以下「V-601」ともいう。)の0.43g、を添加し、重合反応を開始した。
混合物を75℃で2時間加熱した後、更にV-601の0.43gを混合物に追加した。2時間後、更にV-601の0.43gを混合物に追加した。
更に2時間反応後、混合物を90℃に昇温し、3時間撹拌した。上記操作により、重合反応は終了した。
反応終了後、空気下でアミン化合物としてジメチルドデシルアミンの9.6gと重合禁止剤として2,2,6,6,-テトラメチルピペリジン1-オキシルの0.3gを加えた後、反応性化合物として4-ヒドロキシブチルアクリレートグリシジルエーテルの9.01gを滴下した。
滴下終了後、空気下、90℃、24時間反応を続けた後、酸価測定により反応終了を確認した。得られた混合物に30質量%溶液になるようPGMEAを追加することで樹脂PA-1を得た。
得られた樹脂PA-1の重量平均分子量(Mw)は17200、酸価は70mgKOH/mg、C=C価は0.45mmol/g、アミン価は0.45mmol/gであった。
マクロモノマーB-1:下記構造の化合物(Mw:3000)
In a three-necked flask, 60.78 g (PGMEA: 30.39 g, macromonomer B-1 (30.39 g)) of a macromonomer B-1 solution having a concentration (solid content) of 50% by mass, ω-carboxy-poly. 50.99 g of caprolactone monoacrylate (Aronix M-5300, manufactured by Toa Synthetic Co., Ltd.) and 159.5 g of PGMEA (propylene glycol 1-monomethyl ether 2-acetate) were introduced to obtain a mixture.
The mixture was stirred while blowing nitrogen. The mixture was then warmed to 75 ° C. while flowing nitrogen into the flask. Next, 0.82 g of dodecyl mercaptan and then 0.43 g of 2,2'-azobis (methyl 2-methylpropionate) (hereinafter, also referred to as "V-601") were added to the mixture for polymerization. The reaction was initiated.
After heating the mixture at 75 ° C. for 2 hours, an additional 0.43 g of V-601 was added to the mixture. After 2 hours, an additional 0.43 g of V-601 was added to the mixture.
After a further reaction for 2 hours, the mixture was heated to 90 ° C. and stirred for 3 hours. The polymerization reaction was completed by the above operation.
After completion of the reaction, 9.6 g of dimethyldodecylamine as an amine compound and 0.3 g of 2,2,6,6, -tetramethylpiperidine 1-oxyl as a polymerization inhibitor were added under air as a reactive compound. 9.01 g of 4-hydroxybutyl acrylate glycidyl ether was added dropwise.
After the completion of the dropping, the reaction was continued in air at 90 ° C. for 24 hours, and then the reaction completion was confirmed by acid value measurement. Resin PA-1 was obtained by adding PGMEA to the obtained mixture so as to form a 30% by mass solution.
The weight average molecular weight (Mw) of the obtained resin PA-1 was 17,200, the acid value was 70 mgKOH / mg, the C = C value was 0.45 mmol / g, and the amine value was 0.45 mmol / g.
Macromonomer B-1: Compound having the following structure (Mw: 3000)
三口フラスコに、濃度(固形分含有量)が50質量%のマクロモノマーB-1溶液の82.76g(PGMEA:41.38g、マクロモノマーB-1(41.38g))、ω-カルボキシ-ポリカプロラクトンモノアクリレート(アロニックスM-5300、東亞合成(株)製)の44.14g、PGMEAの159.5gを導入し、混合物を得た。
窒素を吹き込みながら、上記混合物を撹拌した。次に、窒素をフラスコ内に流しながら、混合物を75℃まで昇温した。次に、混合物に、ドデシルメルカプタンの0.82g、次いで、V-601の0.43gを添加し、重合反応を開始した。
混合物を75℃で2時間加熱した後、更にV-601の0.43gを混合物に追加した。2時間後、更にV-601の0.43gを混合物に追加した。
更に2時間反応後、混合物を90℃に昇温し、3時間撹拌した。上記操作により、重合反応は終了した。
反応終了後、空気下でアミン化合物としてジメチルドデシルアミンの6.43gと重合禁止剤として4-ヒドロキシ-2,2,6,6,-テトラメチルピペリジン2-オキシルの0.3gを加えた後、反応性化合物として4-ヒドロキシブチルアクリレートグリシジルエーテルの8.05g)を滴下した。
滴下終了後、空気下、90℃、24時間反応を続けた後、酸価測定により反応終了を確認した。得られた混合物に30質量%溶液になるようPGMEAを追加することで樹脂PA-2を得た。
得られた樹脂PA-2の重量平均分子量(Mw)は23300、酸価は60mgKOH/mg、
C=C価は0.4mmol/g、アミン価は0.3mmol/gであった。
であった。 Dispersant D4: Resin PA-2 produced by the following method
82.76 g (PGMEA: 41.38 g, macromonomer B-1 (41.38 g)) and ω-carboxy-poly of a macromonomer B-1 solution having a concentration (solid content) of 50% by mass in a three-necked flask. 44.14 g of caprolactone monoacrylate (Aronix M-5300, manufactured by Toa Synthetic Co., Ltd.) and 159.5 g of PGMEA were introduced to obtain a mixture.
The mixture was stirred while blowing nitrogen. The mixture was then warmed to 75 ° C. while flowing nitrogen into the flask. Next, 0.82 g of dodecyl mercaptan and then 0.43 g of V-601 were added to the mixture to initiate the polymerization reaction.
After heating the mixture at 75 ° C. for 2 hours, an additional 0.43 g of V-601 was added to the mixture. After 2 hours, an additional 0.43 g of V-601 was added to the mixture.
After a further reaction for 2 hours, the mixture was heated to 90 ° C. and stirred for 3 hours. The polymerization reaction was completed by the above operation.
After completion of the reaction, 6.43 g of dimethyldodecylamine as an amine compound and 0.3 g of 4-hydroxy-2,2,6,6, -tetramethylpiperidine 2-oxyl as a polymerization inhibitor were added under air, and then. As a reactive compound, 8.05 g) of 4-hydroxybutyl acrylate glycidyl ether was added dropwise.
After the completion of the dropping, the reaction was continued in air at 90 ° C. for 24 hours, and then the reaction completion was confirmed by acid value measurement. Resin PA-2 was obtained by adding PGMEA to the obtained mixture so as to form a 30% by mass solution.
The weight average molecular weight (Mw) of the obtained resin PA-2 was 23,300, and the acid value was 60 mgKOH / mg.
The C = C value was 0.4 mmol / g, and the amine value was 0.3 mmol / g.
Met.
溶剤S1:プロピレングリコールモノメチルエーテルアセテート(PGMEA) (solvent)
Solvent S1: Propylene glycol monomethyl ether acetate (PGMEA)
下記の表に記載の原料を混合して、実施例および比較例の着色組成物を調製した。
The raw materials listed in the table below were mixed to prepare coloring compositions of Examples and Comparative Examples.
(樹脂)
樹脂B1:下記構造の樹脂(主鎖に付記した数値はモル比である。Mw:30000)
(resin)
Resin B1: Resin having the following structure (the numerical value added to the main chain is the molar ratio. Mw: 30000)
重合性モノマーE1:KAYARAD DPHA(日本化薬(株)製)
重合性モノマーE2:NKエステル A-DPH-12E(新中村化学工業(株)製)
重合性モノマーE3:NKエステル A-TMMT(新中村化学工業(株)製)
重合性モノマーE4:コハク酸変性ジペンタエリスリトールペンタアクリレート
重合性モノマーE5:ジペンタエリスリトールヘキサアクリレート
重合性モノマーE6:ジペンタエリスリトールペンタアクリレート
(光重合開始剤)
光重合開始剤I1:IRGACURE 369 (BASF製)
光重合開始剤I2:IRGACURE OXE01 (BASF製)
光重合開始剤I3:IRGACURE OXE02 (BASF製)
光重合開始剤I4:下記構造の化合物
Polymerizable Monomer E1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
Polymerizable Monomer E2: NK Ester A-DPH-12E (manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
Polymerizable Monomer E3: NK Ester A-TMMT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
Polymerizable monomer E4: Succinic acid-modified dipentaerythritol pentaacrylate Polymerizable monomer E5: Dipentaerythritol hexaacrylate Polymerizable monomer E6: Dipentaerythritol pentaacrylate (photopolymerization initiator)
Photopolymerization Initiator I1: IRGACURE 369 (manufactured by BASF)
Photopolymerization Initiator I2: IRGACURE OXE01 (manufactured by BASF)
Photopolymerization Initiator I3: IRGACURE OXE02 (manufactured by BASF)
Photopolymerization Initiator I4: Compound with the following structure
界面活性剤F1:下記構造の化合物(下記の式中、繰り返し単位の割合を示す%はモル%である。Mw:14000)。
Surfactant F1: A compound having the following structure (in the formula below,% indicating the ratio of the repeating unit is mol%. Mw: 14000).
重合禁止剤H1:p-メトキシフェノール (Polymerization inhibitor)
Polymerization inhibitor H1: p-methoxyphenol
溶剤S1:プロピレングリコールモノメチルエーテルアセテート(PGMEA) (solvent)
Solvent S1: Propylene glycol monomethyl ether acetate (PGMEA)
ガラス基板上にCT-4000(富士フイルムエレクトロニクスマテリアルズ(株)製)を膜厚が0.1μmとなるようにスピンコート法で塗布し、ホットプレートを用いて220℃で1時間加熱して下地層を形成した。この下地層付きのガラス基板上に各着色組成物をスピンコート法で塗布し、その後、ホットプレートを用いて100℃で2分間加熱して塗布膜を得た。得られた塗布膜について、365nmの波長の光を照射し、露光量500mJ/cm2にて露光を行った。次いで、ホットプレートを用いて220℃で5分間加熱して、膜厚0.5μmの硬化膜を得た。得られた硬化膜について、大塚電子(株)製のMCPD-3000を用い、400~700nmの範囲の光透過率(透過率)を測定した。
次に、上記で作製した硬化膜を265℃で5分間加熱した。加熱後の硬化膜の透過率を測定し、透過率の変化量の最大値を求め、以下の基準にて耐熱性を評価した。
透過率の測定は各試料につき5回行い、最大値と最小値を除いた3回の結果の平均値を採用した。また、透過率の変化量の最大値とは、加熱前後の硬化膜の、波長400~700nmの範囲における透過率の変化量が最も大きい波長における変化量を意味する。
(評価基準)
5:透過率の変化量の最大値が1%以下である。
4:透過率の変化量の最大値が1%を超えて、1.5%以下である。
3:透過率の変化量の最大値が1.5%を超えて、2.0%以下である。
2:透過率の変化量の最大値が2.0%を超えて、2.5%以下である。
1:透過率の変化量の最大値が2.5%を超えている。 <Heat resistance evaluation>
CT-4000 (manufactured by FUJIFILM Electronics Materials Co., Ltd.) is applied on a glass substrate by a spin coating method so that the film thickness is 0.1 μm, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum. Each coloring composition was applied onto the glass substrate with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a coating film. The obtained coating film was irradiated with light having a wavelength of 365 nm and exposed at an exposure amount of 500 mJ / cm 2 . Then, it was heated at 220 ° C. for 5 minutes using a hot plate to obtain a cured film having a film thickness of 0.5 μm. With respect to the obtained cured film, the light transmittance (transmittance) in the range of 400 to 700 nm was measured using MCPD-3000 manufactured by Otsuka Electronics Co., Ltd.
Next, the cured film prepared above was heated at 265 ° C. for 5 minutes. The transmittance of the cured film after heating was measured, the maximum value of the amount of change in the transmittance was determined, and the heat resistance was evaluated according to the following criteria.
The transmittance was measured 5 times for each sample, and the average value of the results of 3 times excluding the maximum value and the minimum value was adopted. Further, the maximum value of the amount of change in the transmittance means the amount of change in the cured film before and after heating at the wavelength where the amount of change in the transmittance in the wavelength range of 400 to 700 nm is the largest.
(Evaluation criteria)
5: The maximum value of the amount of change in transmittance is 1% or less.
4: The maximum value of the amount of change in transmittance exceeds 1% and is 1.5% or less.
3: The maximum value of the amount of change in transmittance exceeds 1.5% and is 2.0% or less.
2: The maximum value of the amount of change in transmittance exceeds 2.0% and is 2.5% or less.
1: The maximum value of the amount of change in transmittance exceeds 2.5%.
顔料R1を10.64質量部と、顔料誘導体Sy1を1.33質量部と、分散剤D1を1.99質量部と、分散剤D2を1.99質量部と、マゼンタ色染料M1を2.02質量部と、溶剤S1を82.03質量部と、混合して混合液を得た。得られた混合液を、循環型分散装置(ビーズミル)として寿工業株式会社製のウルトラアペックスミル(商品名)を用いて分散処理を行い、分散液MRD1を調製した。実施例1の着色組成物において、顔料分散液1とマゼンタ色着色剤溶液のかわりに、分散液MRD1の60.91質量部を添加した以外は、実施例1の着色組成物と同様にして実施例63の着色組成物を調製した。この着色組成物を用いて、上記と同様の方法で耐熱性を評価したところ、「2」の評価であった。 (Example 63)
Pigment R1 is 10.64 parts by mass, pigment derivative Sy1 is 1.33 parts by mass, dispersant D1 is 1.99 parts by mass, dispersant D2 is 1.99 parts by mass, and magenta dye M1 is 2. 02 parts by mass and 82.03 parts by mass of the solvent S1 were mixed to obtain a mixed solution. The obtained mixed solution was subjected to dispersion treatment using an Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulating dispersion device (bead mill) to prepare a dispersion solution MRD1. In the coloring composition of Example 1, 60.91 parts by mass of the dispersion liquid MRD1 was added instead of the pigment dispersion liquid 1 and the magenta color colorant solution, but the same procedure as in Example 1 was carried out. The coloring composition of Example 63 was prepared. When the heat resistance was evaluated by the same method as described above using this coloring composition, the evaluation was "2".
シリコンウエハ上に、Green組成物をポストベーク後の膜厚が1.0μmになるようにスピンコート法で塗布した。次いで、ホットプレートを用いて、100℃で2分間加熱した。次いで、i線ステッパー露光装置FPA-3000i5+(キヤノン(株)製)を用い、365nmの波長光を1000mJ/cm2の露光量で2μm四方のドットパターンのマスクを介して照射(露光)した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにてリンスを行い、更に純水にて水洗した。次いで、ホットプレートを用いて、200℃で5分間加熱(ポストベーク)することで、Green組成物をパターニングした。同様にRed組成物、Blue組成物を順次パターニングし、緑、赤及び青の着色パターン(ベイヤーパターン)を形成した。
Red組成物としては、実施例3の着色組成物を使用した。Green組成物及びBlue組成物については後述する。なお、ベイヤーパターンとは、米国特許第3971065号明細書に開示されているような、一個の赤色(Red)素子と、二個の緑色(Green)素子と、一個の青色(Blue)素子とを有する色フィルタ素子の2×2アレイを繰り返したパターンである。得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。この固体撮像素子は好適な画像認識能を有していた。 (Example 1001)
The Green composition was applied onto a silicon wafer by a spin coating method so that the film thickness after post-baking was 1.0 μm. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), light having a wavelength of 365 nm was irradiated (exposed) with an exposure amount of 1000 mJ / cm 2 through a mask of a 2 μm square dot pattern. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and further washed with pure water. The Green composition was then patterned by heating (post-baking) at 200 ° C. for 5 minutes using a hot plate. Similarly, the Red composition and the Blue composition were sequentially patterned to form green, red and blue coloring patterns (Bayer patterns).
As the Red composition, the coloring composition of Example 3 was used. The Green composition and the Blue composition will be described later. The Bayer pattern includes one red (Red) element, two green (Green) elements, and one blue (Blue) element as disclosed in US Pat. No. 3,971,065. It is a pattern in which a 2 × 2 array of color filter elements is repeated. The obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had a suitable image recognition ability.
[Green顔料分散液の調製]
C.I.ピグメントグリーン36を6.4質量部、C.I.ピグメントイエロー150を5.3質量部、分散剤(Disperbyk-161、BYKChemie社製)を5.2質量部、PGMEAを83.1質量部からなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合及び分散して、顔料分散液を調製した。その後更に、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2,000kg/cm3の圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返し、Green顔料分散液を調製した。 -Green composition-
[Preparation of Green Pigment Dispersion]
C. I. Pigment Green 36 at 6.4 parts by mass, C.I. I. A mixed solution consisting of 5.3 parts by mass of Pigment Yellow 150, 5.2 parts by mass of dispersant (Disperbyk-161, manufactured by BYK Chemie), and 83.1 parts by mass of PGMEA is used in a bead mill (zirconia beads 0.3 mm diameter). A pigment dispersion was prepared by mixing and dispersing for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment was repeated 10 times to prepare a Green pigment dispersion.
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、Green組成物を調製した。
Green顔料分散液:73.7質量部
樹脂B2の40質量%PGMEA溶液:0.3質量部
重合性モノマーE1:1.2質量部
光重合開始剤I2:0.6質量部
界面活性剤F1の1質量%PGMEA溶液:4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製):0.5質量部
PGMEA:19.5質量部 [Preparation of Green Composition]
The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 μm to prepare a Green composition.
Green pigment dispersion: 73.7 parts by mass 40% by mass of resin B2 PGMEA solution: 0.3 parts by mass Polymerizable monomer E1: 1.2 parts by mass Photopolymerization initiator I2: 0.6 parts by mass Of the surfactant F1 1% by mass PGMEA solution: 4.2 parts by mass UV absorber (UV-503, manufactured by Daito Kagaku Co., Ltd.): 0.5 parts by mass PGMEA: 19.5 parts by mass
[Blue顔料分散液の調製]
C.I.ピグメントブルー15:6を9.7質量部、C.I.ピグメントバイオレット23を2.4質量部、分散剤(Disperbyk-161、BYKChemie社製)を5.5質量部、PGMEAを82.4質量部からなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合及び分散して、顔料分散液を調製した。その後更に、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2,000kg/cm3の圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返し、Blue顔料分散液を調製した。 -Blue composition-
[Preparation of Blue Pigment Dispersion]
C. I. Pigment Blue 15: 6 at 9.7 parts by mass, C.I. I. A mixed solution consisting of 2.4 parts by mass of Pigment Violet 23, 5.5 parts by mass of a dispersant (Disperbyk-161, manufactured by BYK Chemie), and 82.4 parts by mass of PGMEA was used as a bead mill (zirconia beads 0.3 mm diameter). A pigment dispersion was prepared by mixing and dispersing for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment was repeated 10 times to prepare a Blue pigment dispersion.
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、Blue組成物を調製した。
Blue顔料分散液:44.9質量部
樹脂B2の40質量%PGMEA溶液:2.1質量部
重合性モノマーE1:1.5質量部
下記の構造の重合性モノマー:0.7質量部
界面活性剤F1の1質量%PGMEA溶液:4.2質量部
PGMEA:45.8質量部 [Preparation of Blue composition]
The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 μm to prepare a Blue composition.
Blue pigment dispersion: 44.9 parts by mass 40% by mass of resin B2 PGMEA solution: 2.1 parts by mass Polymerizable monomer E1: 1.5 parts by mass Polymerizable monomer having the following structure: 0.7 parts by mass
Claims (22)
- ジケトピロロピロール顔料と、マゼンタ色染料と、硬化性基を有する化合物と、を含み、
前記ジケトピロロピロール顔料は、芳香族環に電子供与性基が導入された芳香族環基がジケトピロロピロール骨格に結合した構造を有する顔料Aを含む、着色組成物。 It contains a diketopyrrolopyrrole pigment, a magenta dye, and a compound having a curable group.
The diketopyrrolopyrrole pigment is a coloring composition containing a pigment A having a structure in which an aromatic ring group having an electron-donating group introduced into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton. - 前記顔料Aが有する前記電子供与性基は、ヒドロキシ基、アルキル基、アルコキシ基、アルキルチオ基、アリールオキシ基およびアミノ基から選ばれる少なくとも1種である、請求項1に記載の着色組成物。 The coloring composition according to claim 1, wherein the electron donating group contained in the pigment A is at least one selected from a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group and an amino group.
- 前記顔料Aが有する前記電子供与性基が炭素数1~3のアルキル基である、請求項1に記載の着色組成物。 The coloring composition according to claim 1, wherein the electron-donating group of the pigment A is an alkyl group having 1 to 3 carbon atoms.
- 前記顔料Aが有する前記芳香族環基は、下記式(AR-1)で表される基である、請求項1~3のいずれか1項に記載の着色組成物;
- 前記顔料Aは、下記式(1)で表される化合物である、請求項1~4のいずれか1項に記載の着色組成物;
- 前記顔料Aは、下記式(2)で表される化合物である、請求項1~5のいずれか1項に記載の着色組成物;
- 前記顔料Aは赤色顔料である、請求項1~6のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 6, wherein the pigment A is a red pigment.
- 前記マゼンタ色染料は、キナクリドン化合物、キサンテン化合物、トリアリールメタン化合物、シアニン化合物、アントラキノン化合物およびジピロメテン化合物からなる群から選択される少なくとも1種を含む、請求項1~7のいずれか1項に記載の着色組成物。 The magenta color dye according to any one of claims 1 to 7, further comprising at least one selected from the group consisting of a quinacridone compound, a xanthene compound, a triarylmethane compound, a cyanine compound, an anthraquinone compound and a dipyrromethene compound. Coloring composition.
- 前記マゼンタ色染料は、カチオン性シアニン発色団とイミドアニオンとの塩を含む、請求項1~7のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 7, wherein the magenta color dye contains a salt of a cationic cyanine chromophore and an imide anion.
- 前記顔料Aの100質量部に対して、前記マゼンタ色染料を1~50質量部含む、請求項1~9のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 9, which contains 1 to 50 parts by mass of the magenta color dye with respect to 100 parts by mass of the pigment A.
- 更に、黄色着色剤を含む、請求項1~10のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 10, further comprising a yellow colorant.
- 前記硬化性基を有する化合物は、エチレン性不飽和基を有する化合物を含み、前記着色組成物は更に光重合開始剤を含む、請求項1~11のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 11, wherein the compound having a curable group contains a compound having an ethylenically unsaturated group, and the coloring composition further contains a photopolymerization initiator.
- 前記着色組成物の全固形分中における前記顔料Aの含有量が40質量%以上である、請求項1~12のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 12, wherein the content of the pigment A in the total solid content of the coloring composition is 40% by mass or more.
- 前記ジケトピロロピロール顔料は、前記顔料Aを2種以上含む、請求項1~13のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 13, wherein the diketopyrrolopyrrole pigment contains two or more of the pigments A.
- 前記ジケトピロロピロール顔料は、更に、前記顔料A以外のジケトピロロピロール顔料を含む、請求項1~14のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 14, wherein the diketopyrrolopyrrole pigment further contains a diketopyrrolopyrrole pigment other than the pigment A.
- 固体撮像素子用である、請求項1~15のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 15, which is used for a solid-state image sensor.
- カラーフィルタ用である、請求項1~16のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 16, which is used for a color filter.
- 請求項1~17のいずれか1項に記載の着色組成物から得られる硬化膜。 A cured film obtained from the coloring composition according to any one of claims 1 to 17.
- 請求項1~17のいずれか1項に記載の着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法またはドライエッチング法により着色組成物層に対してパターンを形成する工程と、を有するパターン形成方法。 A step of forming a coloring composition layer on a support using the coloring composition according to any one of claims 1 to 17, and a pattern on the coloring composition layer by a photolithography method or a dry etching method. A pattern forming method comprising a step of forming and.
- 請求項18に記載の硬化膜を有するカラーフィルタ。 The color filter having the cured film according to claim 18.
- 請求項18に記載の硬化膜を有する固体撮像素子。 A solid-state image sensor having the cured film according to claim 18.
- 請求項18に記載の硬化膜を有する画像表示装置。 An image display device having the cured film according to claim 18.
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