WO2022230625A1 - 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 Download PDFInfo
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- C09B25/00—Quinophthalones
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/22—Monoazo compounds containing other metals
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- 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
- C09B55/00—Azomethine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- C09B57/04—Isoindoline dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Definitions
- the present invention relates to coloring compositions.
- the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition.
- the present invention also relates to squarylium compounds.
- Optical filters such as color filters are manufactured using a coloring composition containing a coloring agent and a curable compound.
- a coloring composition containing a coloring agent and a curable compound.
- the use of squarylium compounds as colorants has been investigated.
- Patent Document 1 describes a coloring composition using a specific squarylium compound as a coloring agent.
- squarylium compounds tend to have strong hydrogen bonding between compounds. Therefore, in a colored composition using a squarylium compound as a colorant, the squarylium compounds in the colored composition tend to aggregate due to hydrogen bonding or the like, and the colored composition tends to be highly thixotropic.
- the thickness of the resulting film tends to be uneven. In particular, the thinner the film to be formed, the greater the unevenness in thickness.
- the coloring composition using a squarylium compound as a coloring agent has room for improvement in coatability.
- an object of the present invention is to provide a coloring composition that is excellent in coatability and capable of forming a film with little thickness unevenness.
- Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, an image display device, and a compound.
- the present invention provides the following.
- a 1 represents a squarylium dye structure
- Y 1 represents a single bond or a (l+1)-valent linking group, and when there are multiple Y 1 s, the plurality of Y 1s may be the same or different
- M p+ represents a counter cation
- l, m, n and q each independently represents an integer of 1 or more
- p represents an integer of 2 or more
- l*m*n p*q.
- a 11 and A 12 each independently represent an aryl group, a heterocyclic group or a group represented by formula (R1), and at least one of A 11 and A 12 represents formula (I ) with Y 1 ;
- * represents a linker with the squaric acid moiety of formula (sq1)
- Rs 1 to Rs 3 each independently represent a hydrogen atom or an alkyl group
- As 3 represents a heterocyclic group
- n s1 represents an integer of 0 or more
- Rs 1 and Rs 2 may combine with each other to form a ring
- Rs 1 and As 3 may combine with each other to form a ring
- Rs 2 and Rs 3 may combine with each other to form a ring
- the plurality of Rs 2 and Rs 3 may be the same or different
- a 11 and A 12 in formula (sq1) is a group represented by formula (A1);
- * represents a linker with the squaric acid moiety of formula (sq1),
- Ra 1 to Ra 5 independently represents a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, an amino group, or a bond with Y 1 of formula (I).
- ⁇ 6> The colored composition according to ⁇ 5>, wherein -Y 2 -[COO-] l in formula (III) is a group represented by formula (Y-1);
- R Y1 represents a hydrogen atom, an alkyl group or an aryl group;
- L Y1 represents a (l+1)-valent linking group, l represents an integer of 1 or more, * represents a link with A 21 or A 22 of formula (III).
- ⁇ 7> The colored composition according to any one of ⁇ 1> to ⁇ 6>, wherein the compound represented by formula (I) is a lake dye.
- ⁇ 8> The coloring according to any one of ⁇ 1> to ⁇ 7>, wherein the compound represented by formula (I) is a green coloring agent, a magenta coloring agent, a purple coloring agent or a blue coloring agent.
- Composition. ⁇ 9> The content of the compound represented by the formula (I) in the total solid content of the coloring composition is 10 to 60% by mass, ⁇ 1> to ⁇ 8> according to any one of ⁇ 1> to ⁇ 8> coloring composition.
- ⁇ 10> The colored composition according to any one of ⁇ 1> to ⁇ 9>, wherein the curable compound comprises a polymerizable compound.
- the curable compound comprises a resin.
- ⁇ 12> The colored composition according to ⁇ 11>, wherein the resin includes a resin having an acid group.
- ⁇ 14> The colored composition according to any one of ⁇ 1> to ⁇ 13>, which is for a solid-state imaging device.
- ⁇ 15> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 14>.
- ⁇ 16> An optical filter comprising the film according to ⁇ 15>.
- ⁇ 17> A solid-state imaging device comprising the film according to ⁇ 15>.
- ⁇ 18> An image display device comprising the film according to ⁇ 15>.
- a 21 and A 22 each independently represent an aryl group, a heterocyclic group or a group represented by formula (R1), and at least one of A 21 and A 22 is Y 2 and with the proviso that at least one of A 21 and A 22 is a group represented by formula (A1);
- Y 2 represents a single bond or a (l+1)-valent linking group, and when multiple Y 2 are present, the multiple Y 2 may be the same or different;
- M p+ represents the counter cation;
- * represents a linker with the squaric acid moiety of formula (III)
- Rs 1 to Rs 3 each independently represent a hydrogen atom or an alkyl group, As 3 represents a heterocyclic group, n s1 represents an integer of
- the present invention it is possible to provide a coloring composition that is excellent in coatability and capable of forming a film with little thickness unevenness.
- the present invention can also provide films, optical filters, solid-state imaging devices, image display devices, and compounds.
- ⁇ is used to include the numerical values before and after it as lower and upper limits.
- a description that does not describe substitution or unsubstituted includes a group (atomic group) having no substituent as well as a group (atomic group) having a substituent.
- an "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).
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- EUV light extreme ultraviolet rays
- (meth)acrylate” represents both or either acrylate and methacrylate
- (meth)acryl represents both or either acrylic and methacrylic
- (meth) ) acryloyl refers to acryloyl and/or methacryloyl.
- Me in the structural formulas represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
- total solid content refers to the total mass of all components of the composition excluding the solvent.
- a pigment means a coloring agent that is difficult to dissolve in a solvent.
- the term "process” includes not only an independent process, but also when the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. .
- the coloring composition of the present invention comprises a coloring agent and a curable compound,
- the coloring agent contains a compound represented by formula (I), and the compound represented by formula (I) has a maximum absorption wavelength in a wavelength range of 500 nm or more and less than 700 nm.
- the coloring composition of the present invention it is possible to form a film with excellent applicability and small thickness unevenness.
- the compound represented by the formula (I) has a squarylium dye laked by a counter cation, so the hydrogen between the compounds in the coloring composition It is presumed that this is because aggregation due to binding or the like is suppressed, and as a result, the thixotropy of the coloring composition can be reduced.
- the thixotropy is a phenomenon in which the viscosity reversibly changes between a static state and a fluid state.
- the colored composition of the present invention can be preferably used as a colored composition for pattern formation by photolithography.
- the coloring composition of the present invention is used as a coloring composition for photolithography, it is preferable to use a resin having an acid group and a polymerizable monomer (monomer type polymerizable compound) as a curable compound, It is more preferable to use a resin having an acid group and a polymerizable monomer (monomer-type polymerizable compound) having an ethylenically unsaturated bond-containing group.
- the coloring composition further contains a photopolymerization initiator. Pixels having excellent pattern linearity can be formed by patterning the colored composition of the present invention by photolithography to form pixels.
- the coloring composition of the present invention is preferably used as a coloring composition for optical filters.
- optical filters include color filters and infrared transmission filters, and color filters are preferred. That is, the coloring composition of the present invention is preferably used as a coloring composition for color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter.
- the types of pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, and the like. Green pixels or blue pixels are preferable, and green pixels are more preferable.
- the maximum transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1100 to 1300 nm.
- Filters satisfying spectral characteristics with a value of 70% or more are preferred.
- the infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5).
- the maximum transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 800 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 900 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1000 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1100 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1200 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the colored composition of the present invention is preferably used for solid-state imaging devices. More specifically, it is preferably used as a coloring composition for optical filters used in solid-state imaging devices, and more preferably used as a coloring composition for color filters used in solid-state imaging devices.
- the solid content concentration of the coloring composition of the present invention is preferably 5 to 30% by mass.
- the lower limit is preferably 7.5% by mass or more, more preferably 10% by mass or more.
- the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less.
- the coloring composition of the present invention contains a coloring agent.
- a coloring agent containing a compound represented by formula (I) is used.
- the compound represented by (I) is also referred to as a specific colorant.
- a 1 represents a squarylium dye structure
- Y 1 represents a single bond or a (l+1)-valent linking group
- M p+ represents a counter cation
- l, m, n and q each independently represents an integer of 1 or more
- p represents an integer of 2 or more
- l*m*n p*q.
- the squarylium dye structure represented by A1 in formula ( I ) is preferably a structure represented by formula (sq1).
- a 11 and A 12 each independently represent an aryl group, a heterocyclic group or a group represented by formula (R1), and at least one of A 11 and A 12 represents formula (I ) with Y 1 ;
- * represents a linker with the squaric acid moiety of formula (sq1)
- Rs 1 to Rs 3 each independently represent a hydrogen atom or an alkyl group
- As 3 represents a heterocyclic group
- n s1 represents an integer of 0 or more
- Rs 1 and Rs 2 may combine with each other to form a ring
- Rs 1 and As 3 may combine with each other to form a ring
- Rs 2 and Rs 3 may combine with each other to form a ring
- the plurality of Rs 2 and Rs 3 may be the same or different, At least one selected from Rs 1 , Rs 2 , Rs
- the aryl group represented by A 11 and A 12 preferably has 6 to 48 carbon atoms, more preferably 6 to 22 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
- the heterocyclic group represented by A 11 and A 12 is preferably a 5- or 6-membered heterocyclic group.
- the heterocyclic group is preferably a monocyclic heterocyclic group or a condensed heterocyclic group having 2 to 8 condensed rings, and a monocyclic heterocyclic group or a condensed heterocyclic group having 2 to 4 condensed rings. is more preferred, and a monocyclic heterocyclic group or a condensed heterocyclic group having 2 or 3 condensed rings is even more preferred.
- a heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3, more preferably 1-2.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 1-30, more preferably 1-18, and even more preferably 1-12.
- the aryl group and heterocyclic group may have a substituent. Substituents include the substituent T described later.
- the aryl group and the heterocyclic group may contain a linking hand with Y 1 of formula (I).
- the aryl group is preferably a group represented by formula (A1) described later.
- * in formula (R1) represents a linker with the squaric acid site in formula (sq1).
- the squaric acid site is a site represented by the following formula (sq). That is, * in formula (R1) is a link with the wavy line part in formula (sq).
- Rs 1 to Rs 3 in formula (R1) each independently represent a hydrogen atom or an alkyl group.
- the number of carbon atoms in the alkyl group represented by Rs 1 to Rs 3 is preferably 1-20, more preferably 1-15, and still more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- Rs 1 to Rs 3 are preferably hydrogen atoms.
- the heterocyclic group represented by As 3 in formula (R1) includes the heterocyclic groups described above, and the preferred range is also the same.
- n s1 in formula (R1) represents an integer of 0 or more.
- n s1 is preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
- R1 Rs 1 and Rs 2 may be bonded together to form a ring, Rs 1 and As 3 may be bonded together to form a ring, Rs 2 and Rs 3 are , may combine with each other to form a ring.
- the linking group for forming the above ring is preferably a divalent linking group selected from the group consisting of -CO-, -O-, -NH-, an alkylene group having 1 to 10 carbon atoms and a combination thereof.
- An alkylene group as a linking group may be unsubstituted or may have a substituent. Examples of the substituent include the substituent T described later.
- n s1 when n s1 is 2 or more, a plurality of Rs 2 and Rs 3 may be the same or different.
- a 11 and A 12 are preferably an aryl group or a heterocyclic group, more preferably an aryl group.
- the aryl group is preferably an aryl group having a hydroxy group as a substituent because it can further improve the applicability of the coloring composition and the pattern linearity of pixels.
- At least one of A 11 and A 12 is preferably a group represented by formula (A1), and more preferably both A 11 and A 12 are groups represented by formula (A1).
- * represents a linker with the squaric acid moiety of formula (sq1)
- Ra 1 to Ra 5 each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, an amino group, or a linking hand with Y 1 of formula (I).
- Halogen atoms represented by Ra 1 to Ra 5 include fluorine, chlorine, bromine and iodine atoms.
- the number of carbon atoms in the alkyl groups represented by Ra 1 to Ra 5 is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkyl groups represented by Ra 1 to Ra 5 may have a substituent. Substituents include the substituent T described later.
- the alkoxy groups represented by Ra 1 to Ra 5 preferably have 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and still more preferably 1 to 8 carbon atoms. Alkoxy groups may be straight or branched.
- the alkoxy groups represented by Ra 1 to Ra 5 may have a substituent.
- Substituents include the substituent T described later.
- the aryl group represented by Ra 1 to Ra 5 preferably has 6 to 48 carbon atoms, more preferably 6 to 22 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
- the aryl groups represented by Ra 1 to Ra 5 may have a substituent.
- Substituents include the substituent T described later.
- the heterocyclic groups represented by Ra 1 to Ra 5 include the heterocyclic groups described above, and the preferred ranges are also the same.
- the heterocyclic groups represented by Ra 1 to Ra 5 may have a substituent. Substituents include the substituent T described later.
- Examples of amino groups represented by Ra 1 to Ra 5 include groups represented by —NRa 101 Ra 102 .
- Ra 101 and Ra 102 each independently represent a hydrogen atom, an alkyl group and an aryl group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, and even more preferably 1-3.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- Substituents include the substituent T described later.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- the aryl group may have a substituent. Substituents include the substituent T described later.
- At least one of Ra 1 and Ra 5 in formula (A1) is preferably a hydroxy group.
- Ra 1 and Ra 5 in formula (A1) are hydroxy groups, or an embodiment in which one of Ra 1 and Ra 5 in formula (A1) is a hydroxy group and the other is a hydrogen atom. More preferably, one of Ra 1 and Ra 5 in formula (A1) is a hydroxy group, and the other is a hydrogen atom, because of good spectroscopy, light resistance and heat resistance.
- Ra 2 , Ra 3 and Ra 4 in formula (A1) are each independently preferably a hydrogen atom, an amino group or a linker with Y 1 in formula (I), and Ra 2 and Ra It is more preferable that 4 is a hydrogen atom and Ra 3 is an amino group or a linking hand with Y 1 of formula (I).
- Halogen atom e.g., fluorine atom, chlorine atom, bromine atom, iodine atom
- alkyl group preferably alkyl group having 1 to 30 carbon atoms
- alkenyl group preferably alkenyl group having 2 to 30 carbon atoms
- alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an aryl group having 6 to 30 carbon atoms
- a heterocyclic group preferably a heterocyclic group having 1 to 30 carbon atoms
- an amino group preferably amino group having 0 to 30 carbon atoms
- alkoxy group preferably alkoxy group having 1 to 30 carbon atoms
- aryloxy group preferably aryloxy group having 6 to 30 carbon atoms
- heterocyclic oxy group preferably carbon 1 to 30 heterocyclic oxy groups
- acyl groups preferably acyl groups having 2 to 30 carbon atoms
- alkoxy group preferably al
- Y 1 in formula (I) represents a single bond or a (l+1)-valent linking group, and when there are multiple Y 1 's, the multiple Y 1 's may be the same or different.
- the (l+1)-valent linking group represented by Y 1 in formula (I) includes an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, and -COO- , —OCO—, —SO 2 —, —NR Y —, —NR Y CO—, —CONR Y —, —NR Y SO 2 —, —SO 2 NR Y — and groups consisting of combinations thereof, RY represents a hydrogen atom, an alkyl group or an aryl group.
- the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-20, more preferably 2-20, still more preferably 2-10, and particularly preferably 2-5.
- the aliphatic hydrocarbon group may be linear, branched or cyclic.
- the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic.
- the number of carbon atoms in the aromatic hydrocarbon group is preferably 6-18, more preferably 6-14, even more preferably 6-10.
- the aromatic hydrocarbon group is preferably a monocyclic or condensed ring aromatic hydrocarbon group having 2 to 4 condensed rings.
- the heterocyclic group is preferably a 5- or 6-membered heterocyclic group.
- the heterocyclic group is preferably a monocyclic heterocyclic group or a condensed heterocyclic group having 2 to 8 condensed rings, and a monocyclic heterocyclic group or a condensed heterocyclic group having 2 to 4 condensed rings. is more preferred, and a monocyclic heterocyclic group or a condensed heterocyclic group having 2 or 3 condensed rings is even more preferred.
- a heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3, more preferably 1-2.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 1-30, more preferably 1-18, and still more preferably 1-12.
- the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent. Examples of the substituent include the substituent T described above.
- the number of carbon atoms in the alkyl group represented by R 1 Y is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- Alkyl groups may be linear, branched or cyclic.
- the alkyl group represented by RY may further have a substituent. Examples of the substituent include the substituent T described above.
- the aryl group represented by R Y preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryl group represented by RY may further have a substituent. Examples of the substituent include the substituent T described above.
- Preferred embodiments of the (l+1)-valent linking group represented by Y 1 of formula (I) include the groups shown in (1) to (15) below, and the groups shown in (7) to (12). is preferred, and groups represented by (7) or (12) are more preferred.
- Counter cations represented by M p+ in formula (I) include p-valent metal cations.
- metal cations include Mg (magnesium) cations, Ca (calcium) cations, Sr (strontium) cations, Ba (barium) cations, Ti (titanium) cations, Zr (zirconium) cations, Cr (chromium) cations, Mn (manganese ) cation, Fe (iron) cation, Co (cobalt) cation, Ni (nickel) cation, Cu (copper) cation, Zn (zinc) cation, Cd (cadmium) cation, Al (aluminum) cation, In (indium) cation , Sn (tin) cation, Pb (lead) cation and Bi (bismuth) cation.
- l, m, n and q in formula (I) each independently represent an integer of 1 or more.
- l is preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2.
- m is preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2.
- n is preferably 1-5, more preferably 1-4, even more preferably 1-3.
- p in formula (I) represents an integer of 2 or more, preferably 2 or 3.
- the specific colorant is preferably a compound represented by formula (III).
- Compounds of formula (III) are compounds of the invention.
- a 21 and A 22 each independently represent an aryl group, a heterocyclic group or a group represented by formula (R1), and at least one of A 21 and A 22 is Y 2 and with the proviso that at least one of A 21 and A 22 is a group represented by formula (A1);
- Y 2 represents a single bond or a (l+1)-valent linking group, and when multiple Y 2 are present, the multiple Y 2 may be the same or different;
- M p+ represents the counter cation;
- * represents a linker with the squaric acid moiety of formula (III)
- Rs 1 to Rs 3 each independently represent a hydrogen
- the aryl group represented by A21 and A22 in formula ( III) is synonymous with the aryl group represented by A11 and A12 in the structure represented by formula ( sq1 ).
- the heterocyclic group represented by A21 and A22 in formula ( III) has the same meaning as the heterocyclic group represented by A11 and A12 in the structure represented by formula ( sq1 ).
- Rs 1 to Rs 3 , As 3 and n s1 in the group represented by formula (R1) represented by A 21 and A 22 in formula (III) are A 11 and A 12 in the structure represented by formula (sq1) is synonymous with Rs 1 to Rs 3 , As 3 and n s1 in the group represented by formula (R1) explained as represented by .
- Ra 1 to Ra 5 in the group represented by formula (A1) represented by A 21 and A 22 in formula (III) are described as being represented by A 11 and A 12 in the structure represented by formula (sq1). They are synonymous with Ra 1 to Ra 5 in the group represented by formula (A1).
- the (l+1)-valent linking group represented by Y 2 in formula (III) is synonymous with the (l+1)-valent linking group represented by Y 1 in formula (I).
- the counter cation represented by M p+ in formula (III) is synonymous with the counter cation represented by M p+ in formula (I).
- l, m, n, p and q of formula (III) are synonymous with l, m, n, p and q of formula (I).
- a 21 and A 22 in formula (III) are each preferably a group represented by formula (A1).
- —Y 2 —[COO—] l in formula (III) is preferably a group represented by formula (Y-1).
- R Y1 represents a hydrogen atom, an alkyl group or an aryl group
- L Y1 represents a (l+1)-valent linking group
- l represents an integer of 1 or more
- * represents a link with A 21 or A 22 of formula (III).
- the number of carbon atoms in the alkyl group represented by R 1 Y1 is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- Alkyl groups may be linear, branched or cyclic.
- the alkyl group represented by R Y1 may further have a substituent. Examples of the substituent include the substituent T described above.
- the aryl group represented by R 1 Y1 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryl group represented by RY1 may further have a substituent. Examples of the substituent include the substituent T described above.
- the (l+1)-valent linking group represented by L Y1 includes an aliphatic hydrocarbon group; an aromatic hydrocarbon group; a group consisting of a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group; , -O- or -S-; a group consisting of a combination of an aromatic hydrocarbon group and -O- or -S-; an aliphatic hydrocarbon group and an aromatic hydrocarbon group; A group consisting of a combination of —O— or —S— and the like can be mentioned.
- the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-20, more preferably 2-20, still more preferably 2-10, and particularly preferably 2-5.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. Moreover, the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-18, more preferably 6-14, even more preferably 6-10.
- the aromatic hydrocarbon group is preferably a monocyclic or condensed ring aromatic hydrocarbon group having 2 to 4 condensed rings.
- An aliphatic hydrocarbon group and an aromatic hydrocarbon group may have a substituent. Examples of the substituent include the substituent T described above.
- Specific examples of the specific colorant include compound (SQ-1) to compound (SQ-27) described in Examples described later.
- the maximum absorption wavelength of the specific colorant exists in the wavelength range of 500 nm or more and less than 700 nm, preferably in the wavelength range of 550 nm or more and less than 695 nm, and more preferably in the wavelength range of 600 nm or more and less than 690 nm.
- the specific coloring agent is preferably a lake pigment.
- the lake pigment means a solvent-soluble pigment (dye) treated with a precipitant such as a metal salt to make it a solvent-insoluble pigment.
- the amount of the specific colorant dissolved in 100 g of propylene glycol monomethyl ether at 23° C. is preferably 1 g or less, more preferably 0.5 g or less.
- the specific coloring agent is preferably a green coloring agent, a magenta coloring agent, a purple coloring agent or a blue coloring agent, more preferably a green coloring agent.
- the coloring agent contained in the coloring composition of the present invention can further contain a coloring agent (another coloring agent) different from the specific coloring agent.
- Other coloring agents used in combination include chromatic coloring agents and black coloring agents.
- chromatic coloring agents include coloring agents having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. Examples include green colorants, red colorants, yellow colorants, purple colorants, blue colorants, orange colorants, and the like.
- the other coloring agent is preferably a chromatic coloring agent, preferably at least one selected from a yellow coloring agent and a green coloring agent, and more preferably a yellow coloring agent.
- Other coloring agents may be pigments or dyes, but are preferably pigments.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is more preferably 5 nm or more, and even more preferably 10 nm or more.
- the upper limit is more preferably 180 nm or less, still more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle diameter of the pigment can be determined from the image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in this specification is the arithmetic mean value of the primary particle sizes of 400 primary particles of the pigment.
- the primary particles of the pigment refer to independent particles without agglomeration.
- green colorants examples include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred.
- the green colorant is preferably a pigment.
- Specific examples of green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65 and 66 are included.
- a green colorant a halogenated zinc phthalocyanine having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720.
- the compound described in Chinese Patent Application No. 106909027 the phthalocyanine compound having a phosphoric acid ester as a ligand described in WO 2012/102395, described in JP 2019-008014.
- the phthalocyanine compound, the phthalocyanine compound described in JP-A-2018-180023, the compound described in JP-A-2019-038958, the aluminum phthalocyanine compound described in JP-A-2020-070426, JP-A-2020-076995 Core-shell type dyes described in, diarylmethane compounds described in JP-A-2020-504758, and the like can also be used.
- the green colorant is C.I. I. Pigment Green 7, 36, 58, 59, 62 and 63 are preferred, C.I. I. Pigment Green 7, 36, 58 and 59 are more preferred.
- red colorants examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, and diketopyrrolopyrrole compounds, anthraquinone compounds, azo It is preferably a compound, more preferably a diketopyrrolopyrrole compound. Also, the red colorant is preferably a pigment. Specific examples of red colorants include C.I. I.
- a red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Japanese Patent No.
- 10-2019-0140741 anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744, JP 2020 -Perylene compounds described in JP-A-079396, perylene compounds described in JP-A-2020-083982, xanthene compounds described in JP-A-2018-035345, paragraph numbers 0025 to 0041 of JP-A-2020-066702
- the described diketopyrrolopyrrole compounds and the like can also be used.
- red colorant a compound having a structure in which an aromatic ring group in which a group having an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used.
- Lumogen F Orange 240 manufactured by BASF, red pigment, perylene pigment
- red colorant can also be used as a red colorant.
- the red coloring agent is C.I. I. Pigment Red 122, 177, 179, 254, 255, 264, 269, 272 and 291 are preferred, and C.I. I. Pigment Red 254, 264, 272 are more preferred.
- yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds and perylene compounds.
- the yellow colorant is preferably a pigment, more preferably an azo pigment, an azomethine pigment, an isoindoline pigment, a pteridine pigment, a quinophthalone pigment or a perylene pigment, more preferably an azo pigment or an azomethine pigment.
- Specific examples of yellow colorants include C.I. I.
- an azobarbiturate nickel complex having the following structure can also be used.
- X 1 to X 16 each 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 formula (QP1) include compounds described in paragraph number 0016 of Japanese Patent No. 6443711 .
- Y 1 to Y 3 each independently represent a halogen atom.
- n and m are integers of 0 to 6; p is an integer of 0 to 5; (n+m) is 1 or more.
- Specific examples of the compound represented by formula (QP2) include compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- the yellow coloring agent is C.I. I. Pigment Yellow 117, 129, 138, 139, 150 and 185 are preferred.
- C.I. 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. of orange pigments.
- C.I. I. Purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61 are included.
- C.I. 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, 88, etc. be done.
- An aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant. Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A-2012-247591 and paragraph number 0047 of JP-A-2011-157478.
- Dyes can also be used as chromatic colorants.
- the dye is not particularly limited, and known dyes can be used.
- a pigment multimer can also be used as a chromatic colorant.
- the dye multimer is preferably a dye dissolved in an organic solvent. Further, the dye multimer may form particles. When the dye multimer is particles, it is usually used in a state of being dispersed in a solvent.
- the particulate dye multimer can be obtained, for example, by emulsion polymerization, and specific examples include the compounds and production methods described in JP-A-2015-214682.
- a 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.
- a plurality of dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 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.
- Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016/031442, etc. Compounds can also be used.
- the chromatic colorants include diarylmethane compounds described in JP-A-2020-504758, triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, and JP-A-2020-117638.
- Xanthene compounds described phthalocyanine compounds described in International Publication No. 2020/174991, isoindoline compounds described in JP-A-2020-160279 or salts thereof, Korean Patent Publication No. 10-2020-0069442 described in Compound represented by formula 1, compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730, represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070
- the chromatic colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, may be used in the rod-like structure, or may be used in both structures.
- Two or more chromatic colorants may be used in combination.
- black may be formed by a combination of two or more chromatic colorants.
- the black colorant is not particularly limited, and known ones can be used.
- inorganic black colorants include carbon black, titanium black, graphite, etc. Carbon black and titanium black are preferred, and titanium black is more preferred.
- Titanium black is black particles containing titanium atoms, preferably low order titanium oxide or titanium oxynitride. Titanium black can be surface-modified as necessary for the purpose of improving dispersibility, suppressing cohesion, and the like. For example, it is possible to coat the surface of titanium black with silicon oxide, titanium oxide, germanium oxide, aluminum oxide, magnesium oxide, or zirconium oxide. Further, treatment with a water-repellent substance as disclosed in Japanese Patent Laid-Open No. 2007-302836 is also possible.
- Titanium black preferably has a small primary particle size and an average primary particle size of individual particles. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles, in which the content ratio of Si atoms and Ti atoms in the dispersion is adjusted to a range of 0.20 to 0.50, may be mentioned. Regarding the dispersion, the description in paragraphs 0020 to 0105 of JP-A-2012-169556 can be referred to, and the contents thereof are incorporated herein.
- titanium black examples include titanium black 10S, 12S, 13R, 13M, 13M-C, 13R-N, 13M-T (trade name: manufactured by Mitsubishi Materials Corporation), Tilac D ( Trade name: manufactured by Ako Kasei Co., Ltd.) and the like.
- organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, and bisbenzofuranone compounds and perylene compounds are preferred.
- the bisbenzofuranone compound JP-A-2010-534726, JP-A-2012-515233, JP-A-2012-515234, International Publication No. 2014/208348, JP-A-2015-525260, etc.
- perylene compounds for example, available as "Irgaphor Black” manufactured by BASF.
- a perylene compound C.I. I. Pigment Black 31, 32 and the like.
- the azomethine compound include compounds described in JP-A-01-170601, JP-A-02-034664, and the like.
- perylene black Liogen Black FK4280, etc.
- paragraphs 0016 to 0020 of JP-A-2017-226821 may be used as the organic black colorant.
- the coloring composition of the present invention further contains a yellow coloring agent in addition to the specific coloring agent described above, it is preferably used as a coloring composition for forming green pixels of color filters.
- the other coloring agent may include a green coloring agent in addition to the yellow coloring agent, or may be only a yellow coloring agent.
- the content of the green coloring agent as the other coloring agent is, with respect to 100 parts by mass of the yellow coloring agent as the other coloring agent, It is preferably 10 to 1000 parts by mass.
- the upper limit is more preferably 500 parts by mass or less, and even more preferably 300 parts by mass or less.
- the lower limit is more preferably 20 parts by mass or more, and even more preferably 30 parts by mass or more.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 10 to 75% by mass.
- the upper limit is more preferably 70% by mass or less, and even more preferably 65% by mass or less.
- the lower limit is more preferably 20% by mass or more, and even more preferably 30% by mass or more.
- the content of the specific coloring agent in the total solid content of the coloring composition is preferably 5 to 70% by mass.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the lower limit is more preferably 10% by mass or more, and even more preferably 20% by mass or more.
- the content of the specific coloring agent in the coloring agent contained in the coloring composition is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, and 50 to 100% by mass. It is even more preferable to have
- the content of the yellow colorant in the colorant is preferably 1 to 50% by mass.
- the upper limit is more preferably 45% by mass or less, and even more preferably 40% by mass or less.
- the lower limit is more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the content of the yellow colorant is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the specific colorant.
- the upper limit is more preferably 45 parts by mass or less, and even more preferably 40 parts by mass or less.
- the lower limit is more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more.
- the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a green coloring agent.
- the green colorant preferably contains a specific colorant.
- the content of the specific coloring agent in the green coloring agent is preferably 50% by mass or more, more preferably 80% by mass or more.
- the coloring composition of the present invention contains a curable compound.
- the curable compound include polymerizable compounds and resins.
- the resin may be a non-polymerizable resin (a resin having no polymerizable group) or a polymerizable resin (a resin having a polymerizable group).
- Polymerizable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
- the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
- the epoxy group may be a cycloaliphatic epoxy group.
- the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
- the curable compound it is preferable to use one containing at least a resin.
- a resin having an acid group and a polymerizable monomer can be used as a curable compound. More preferably, a resin having an acid group and a polymerizable monomer (monomer-type polymerizable compound) having an ethylenically unsaturated bond-containing group are used.
- polymerizable compound examples include compounds having an ethylenically unsaturated bond-containing group and compounds having a cyclic ether group.
- a compound having an ethylenically unsaturated bond-containing group can be preferably used as a radically polymerizable compound.
- a compound having a cyclic ether group can also be preferably used as a cationic polymerizable compound.
- resin-type polymerizable compounds include resins containing repeating units having polymerizable groups.
- the molecular weight of the monomer type polymerizable compound is preferably less than 2000, more preferably 1500 or less.
- the lower limit of the molecular weight of the polymerizable monomer is preferably 100 or more, more preferably 200 or more.
- the weight average molecular weight (Mw) of the resin-type polymerizable compound is preferably 2,000 to 2,000,000.
- the upper limit of the weight-average molecular weight is more preferably 1,000,000 or less, and even more preferably 500,000 or less.
- the lower limit of the weight-average molecular weight is more preferably 3000 or more, even more preferably 5000 or more.
- the compound having an ethylenically unsaturated bond-containing group as a polymerizable monomer is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound.
- Specific examples include paragraph numbers 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraph numbers 0254-0257 of JP-A-2008-292970, and JP-A-2013-253224.
- Examples of compounds having an ethylenically unsaturated bond-containing group include dipentaerythritol tri(meth)acrylate (commercially available as KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.), and dipentaerythritol tetra(meth)acrylate (commercially available).
- KAYARAD D-320 manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol penta(meth)acrylate commercially available KAYARAD D-310, manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol hexa(meth)acrylate ) Acrylate commercially available as KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.
- the (meth)acryloyl groups of these compounds are ethylene glycol and / Or a compound having a structure linked via a propylene glycol residue (for example, SR454 and SR499 commercially available from Sartomer).
- Examples of compounds having an ethylenically unsaturated bond-containing group include diglycerin EO (ethylene oxide)-modified (meth)acrylate (commercially available: M-460, manufactured by Toagosei), pentaerythritol tetraacrylate (Shin-Nakamura Chemical Industry ( Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Nippon Kayaku Co., Ltd.) Toagosei Co., Ltd.), NK Oligo UA-7200 (Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (Taisei Fine Chemical Co., Ltd.), Light acrylate POB-A0 (Kyoeish
- Examples of compounds having an ethylenically unsaturated bond-containing group include trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, and ethylene oxide isocyanurate. It is also preferable to use trifunctional (meth)acrylate compounds such as modified tri(meth)acrylate and pentaerythritol tri(meth)acrylate. Commercial products of trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306 and M-305.
- M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
- a compound having an ethylenically unsaturated bond-containing group may further have an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
- an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
- Commercially available products of such compounds include Aronix M-305, M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- a compound having a caprolactone structure can also be used as the compound having an ethylenically unsaturated bond-containing group.
- the descriptions in paragraphs 0042 to 0045 of JP-A-2013-253224 can be referred to, the contents of which are incorporated herein.
- Compounds having a caprolactone structure include, for example, DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available as a series from Nippon Kayaku Co., Ltd.
- a compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group can also be used.
- Such a compound is preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group and/or a propyleneoxy group, and is a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group. More preferably, it is a tri- to hexa-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups.
- a polymerizable compound having a fluorene skeleton can also be used as the compound having an ethylenically unsaturated bond-containing group.
- Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- the compound having an ethylenically unsaturated bond-containing group it is also preferable to use a compound such as toluene that does not substantially contain environmentally regulated substances.
- Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- Examples of compounds having an ethylenically unsaturated bond-containing group include UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA- 306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 ( Kyoeisha Chemical Co., Ltd.) and the like are also preferably used.
- Compounds having a cyclic ether group include compounds having an epoxy group, compounds having an oxetanyl group, and the like, and compounds having an epoxy group are preferred.
- Compounds having an epoxy group include compounds having 1 to 100 epoxy groups in one molecule.
- the upper limit of the number of epoxy groups can be, for example, 10 or less, or 5 or less.
- the lower limit of the number of epoxy groups is preferably two or more.
- the compound having a cyclic ether group 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; in the case of a polymer, a weight-average molecular weight of 1000 or more).
- the weight average molecular weight of the cyclic ether group is preferably from 200 to 100,000, more preferably from 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
- a resin can be used as a curable compound in the coloring composition of the present invention. It is preferable to use a curable compound containing at least a resin.
- the resin is blended, for example, for dispersing a pigment or the like in a coloring composition or as a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant.
- such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
- a resin having a polymerizable group also corresponds to a polymerizable compound.
- the weight average molecular weight of the resin is preferably 3,000 to 2,000,000.
- the upper limit is more preferably 1,000,000 or less, and even more preferably 500,000 or less.
- the lower limit is more preferably 4000 or more, and even more preferably 5000 or more.
- resins include (meth)acrylic resins, epoxy resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, Polyamide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, vinyl acetate resins, polyvinyl alcohol resins, polyvinyl acetal resins, polyurethane resins, polyurea resins, and the like.
- norbornene resin is preferable from the viewpoint of improving heat resistance.
- Commercially available norbornene resins include, for example, the ARTON series manufactured by JSR Corporation (for example, ARTON F4520). Further, as the resin, the resin described in the examples of International Publication No.
- a resin having a fluorene skeleton can also be preferably used.
- the description of US Patent Application Publication No. 2017/0102610 can be referred to, the content of which is incorporated herein.
- the resin the resin described in paragraphs 0199 to 0233 of JP-A-2020-186373, the alkali-soluble resin described in JP-A-2020-186325, and the Korean Patent Publication No. 10-2020-0078339.
- a resin represented by the formula 1 can also be used.
- a resin having an acid group As the resin.
- acid groups include carboxy groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups. Only one kind of these acid groups may be used, or two or more kinds thereof may be used.
- a resin having an acid group can be used, for example, as an alkali-soluble resin.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is more preferably 50 mgKOH/g or more, still more preferably 70 mgKOH/g or more.
- the upper limit is more preferably 400 mgKOH/g or less, still more preferably 200 mgKOH/g or less, even more preferably 150 mgKOH/g or less, and particularly preferably 120 mgKOH/g or less.
- a resin containing a repeating unit derived from a compound represented by the formula (ED1) and/or a compound represented by the formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferred to include
- 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.
- the description in JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP-A-2013-029760 can be referred to, the contents of which are incorporated herein.
- polymerizable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- repeating unit Ep at least one type of repeating unit selected from repeating units represented by formula (Ep-1) and repeating units represented by formula (Ep-2).
- a resin hereinafter also referred to as resin Ep
- the resin Ep may contain only one of the repeating units represented by the formula (Ep-1) and the repeating unit represented by the formula (Ep-2). -1) and the repeating unit represented by formula (Ep-2) may be included.
- the ratio of the repeating unit represented by the formula (Ep-1) to the repeating unit represented by the formula (Ep-2) is the molar ratio represented by the formula (Ep-1).
- Repeating unit: repeating unit represented by formula (Ep-2) preferably 5:95 to 95:5, more preferably 10:90 to 90:10, 20:80 to 80 :20 is more preferred.
- L 1 represents a single bond or a divalent linking group
- R 1 represents a hydrogen atom or a substituent.
- the substituent represented by R 1 includes an alkyl group and an aryl group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, more preferably 1-3.
- R 1 is preferably a hydrogen atom or a methyl group.
- the divalent linking group represented by L 1 includes 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-, -SO-, -SO 2 -, -CO-, -O-, -COO-, -OCO-, -S- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched.
- the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the content of the repeating unit Ep in the resin Ep is preferably 1 to 100 mol% of all repeating units in the resin Ep.
- the upper limit is more preferably 90 mol % or less, and even more preferably 80 mol % or less.
- the lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
- the resin Ep may have other repeating units in addition to the repeating unit Ep.
- Other repeating units include a repeating unit having an acid group, a repeating unit having an ethylenically unsaturated bond-containing group, and the like.
- the acid group includes a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxy group, more preferably a carboxy group.
- ethylenically unsaturated bond-containing groups examples include vinyl groups, styrene groups, (meth)allyl groups, and (meth)acryloyl groups.
- the content of the repeating unit having an acid group in the resin Ep is preferably 5 to 85 mol% of all repeating units in the resin Ep.
- the upper limit is more preferably 60 mol % or less, even more preferably 40 mol % or less.
- the lower limit is more preferably 8 mol % or more, still more preferably 10 mol % or more.
- the content of the repeating unit having an ethylenically unsaturated bond-containing group in the resin Ep is 1 to 65 mol% of the total repeating units of the resin Ep. is preferably The upper limit is more preferably 45 mol % or less, even more preferably 30 mol % or less. The lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
- the resin Ep preferably further contains a repeating unit having an aromatic hydrocarbon ring.
- the aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the aromatic hydrocarbon ring may have a substituent. An alkyl group etc. are mentioned as a substituent.
- the content of the repeating unit having an aromatic hydrocarbon ring is 1 to 65 in all repeating units of the resin having a cyclic ether group. Mole % is preferred. The upper limit is more preferably 45 mol % or less, even more preferably 30 mol % or less.
- the lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
- Repeating units having an aromatic hydrocarbon ring include repeating units derived from monofunctional polymerizable compounds having an aromatic hydrocarbon ring, such as vinyl toluene and benzyl (meth)acrylate.
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0-15.
- the number of carbon atoms in the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly 2 or 3.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- resin Ac a resin having an aromatic carboxy group
- the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
- the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
- an aromatic carboxy group is a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
- the number of carboxy groups bonded to the aromatic ring is preferably 1-4, more preferably 1-2.
- Resin Ac is preferably a resin containing at least one repeating unit selected from repeating units represented by formula (Ac-1) and repeating units represented by formula (Ac-2).
- Ar 1 represents a group containing an aromatic carboxyl group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- Ar 10 represents a group containing an aromatic carboxyl group
- L 11 represents -COO- or -CONH-
- L 12 represents a trivalent linking group
- P 10 represents a polymer represents a chain.
- aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) examples include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
- Aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides include compounds having the following structures.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
- the group containing an aromatic carboxyl group represented by Ar 1 may have a polymerizable group.
- the polymerizable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, more preferably an ethylenically unsaturated bond-containing group.
- Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). and the like.
- n1 represents an integer of 1 to 4, preferably 1 or 2, more preferably 2.
- n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and still more preferably 2.
- n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, preferably 1 More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- 1) or a group represented by the above formula (Q-2).
- * 1 represents the bonding position with L1.
- L 1 represents -COO- or -CONH-, preferably -COO-.
- the divalent linking group represented by L 2 in formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these A group obtained by combining two or more of The number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the alkylene group may be linear, branched or cyclic.
- the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- An alkylene group and an arylene group may have a substituent. A hydroxy group etc.
- the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
- L 2a is an alkylene group; an arylene group; a combination of an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group; Examples include groups in which at least one selected from —NH— and —S— are combined, and alkylene groups are preferred.
- the number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the alkylene group may be linear, branched or cyclic. An alkylene group and an arylene group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- the group containing an aromatic carboxy group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
- L 11 represents -COO- or -CONH-, preferably -COO-.
- the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and 2 of these Groups in which more than one species are combined are included.
- Hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, even more preferably 6-10.
- the hydrocarbon group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula (L12-2).
- L 12b represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12b includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, and a hydrocarbon group or a group of a combination of a hydrocarbon group and —O— is preferred.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12c includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, preferably a hydrocarbon group.
- P 10 in formula (Ac-2) represents a polymer chain.
- the polymer chain represented by P10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
- the weight average molecular weight of the polymer chain P10 is preferably 500-20,000 .
- the lower limit is more preferably 1000 or more.
- the upper limit is more preferably 10,000 or less, even more preferably 5,000 or less, and even more preferably 3,000 or less. If the weight average molecular weight of P10 is within the above range, the dispersibility of the pigment in the composition is good.
- the resin having an aromatic carboxyl group is a resin having repeating units represented by formula (Ac-2), this resin is preferably used as a dispersant.
- the polymer chain represented by P10 may contain a polymerizable group.
- Polymerizable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- the coloring composition of the present invention preferably contains a resin as a dispersant.
- Dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is greater than the amount of basic groups.
- the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol % or more is preferable when the total amount of the acid group and the basic group is 100 mol %.
- the acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10-105 mgKOH/g.
- a basic dispersant represents a resin in which the amount of basic groups is greater than the amount of acid groups.
- a resin containing more than 50 mol % of basic groups is preferable when the total amount of acid groups and basic groups is 100 mol %.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin for details of the graft resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
- the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of its main chain and side chains.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
- a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- 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.
- resins include, for example, dendrimers (including star polymers).
- dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of repeating units having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70, of the total repeating units of the resin. More preferably, it is mol %.
- resins described in JP-A-2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, Polyethyleneimine having a polyester side chain described in International Publication No. 2016/104803, a block copolymer described in International Publication No. 2019/125940, a block polymer having an acrylamide structural unit described in JP-A-2020-066687 , a block polymer having an acrylamide structural unit described in JP-A-2020-066688, a dispersant described in WO 2016/104803, and the like can also be used.
- the dispersant is also available as a commercial product, and specific examples thereof include the Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
- the product described in paragraph number 0129 of JP-A-2012-137564 and the product described in paragraph number 0235 of JP-A-2017-194662 can also be used as a dispersant.
- the content of the curable compound in the total solid content of the coloring composition is preferably 1 to 70% by mass.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the coloring composition of the present invention may contain only one kind of curable compound, or may contain two or more kinds of curable compounds. When two or more curable compounds are included, the total amount thereof is preferably within the above range.
- the content of the polymerizable compound is preferably 1 to 70% by mass based on the total solid content of the coloring composition.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the coloring composition of the present invention may contain only one polymerizable compound, or may contain two or more polymerizable compounds. When two or more polymerizable compounds are included, the total amount thereof is preferably within the above range.
- the content of the polymerizable monomer is preferably 1 to 50% by mass based on the total solid content of the coloring composition.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 35% by mass or less, even more preferably 30% by mass or less, and even more preferably 20% by mass or less.
- the coloring composition of the present invention may contain only one polymerizable monomer, or may contain two or more polymerizable monomers. When two or more polymerizable monomers are included, the total amount thereof is preferably within the above range.
- the content of the resin is preferably 1 to 70 wt% of the total solid content of the coloring composition.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the content of the resin having an acid group is preferably 1 to 70 mass% of the total solid content of the coloring composition.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the content of the alkali-soluble resin is preferably 1 to 70% by mass of the total solid content of the coloring composition.
- the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the coloring composition of the present invention contains a resin as a dispersant
- the content of the resin as a dispersant is preferably 0.1 to 30% by mass based on the total solid content of the coloring composition.
- the upper limit is more preferably 25% by mass or less, and even more preferably 20% by mass or less.
- the lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the content of the resin as a dispersant is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the specific coloring agent.
- the upper limit is more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less.
- the lower limit is more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more.
- the coloring composition of the present invention may contain only one resin, or may contain two or more resins. When two or more resins are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a photopolymerization initiator.
- the colored composition of the invention preferably contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet range to the visible range are preferred.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl-substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, more preferably oxime compounds.
- hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. are mentioned.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 1173, Irgacure 127 ( company) and the like.
- ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by Irgacure 369E, Irgacure 379EG). made), etc.
- acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, and Irgacure TPO (manufactured by BASF).
- Examples of oxime compounds include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, J. Am. C. S. Compounds described in Perkin II (1979, pp.1653-1660); C. S. Compounds described in Perkin II (1979, pp.156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232), compounds described in JP-A-2000-066385, Compounds described in JP-A-2004-534797, compounds described in JP-A-2017-019766, compounds described in Patent No.
- oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropane-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime) and the like.
- 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 compounds described in JP-A-2014-137466, compounds described in Japanese Patent No. 6636081, and compounds described in Korean Patent Publication No. 10-2016-0109444. mentioned.
- 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 oxime compounds include compounds described in WO2013/083505.
- 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 include compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. and the compound (C-3) of.
- 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 paragraph numbers 0031 to 0047 of JP-A-2013-114249 and paragraph numbers 0008-0012 and 0070-0079 of JP-A-2014-137466; Compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 and ADEKA Arkles NCI-831 (manufactured by ADEKA Corporation) can be mentioned.
- 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 WO 2015/036910.
- an oxime compound in which a substituent having a hydroxyl group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- an oxime compound having an aromatic ring group Ar 2 OX1 in which an electron-withdrawing group is introduced into the aromatic ring (hereinafter also referred to as oxime compound OX) can be used.
- the electron-withdrawing group of the aromatic ring group Ar OX1 include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group.
- a benzoyl group may have a substituent.
- substituents include halogen atoms, cyano groups, nitro groups, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclic oxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, It is preferably an acyl group or an amino group, more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group or an amino group.
- a sulfanyl group or an amino group is more preferred.
- the oxime compound OX is preferably at least one selected from the compounds represented by the formula (OX1) and the compounds represented by the formula (OX2), more preferably the compound represented by the formula (OX2). preferable.
- R X1 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl a group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphinoyl group, a carbamoyl group or a sulfamoyl group
- R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group,
- electron-withdrawing groups include acyl groups, nitro groups, trifluoromethyl groups, alkylsulfinyl groups, arylsulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, and cyano groups, with acyl groups and nitro groups being preferred.
- An acyl group is more preferred, and a benzoyl group is even more preferred, because a film having excellent properties can be easily formed.
- R X12 is an electron-withdrawing group
- R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
- oxime compound OX examples include compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited to these.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, 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 from the viewpoint of sensitivity, more preferably 1000 to 300000, further preferably 2000 to 300000, even more preferably 5000 to 200000. It is particularly preferred to have
- the molar extinction coefficient of a compound can be measured using known methods. For example, it is preferably measured at a concentration of 0.01 g/L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- Irgacure OXE01 manufactured by BASF
- Irgacure OXE02 manufactured by BASF
- Omnirad 2959 manufactured by IGM Resins B.V.
- a bifunctional or trifunctional or higher functional radical photopolymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so good sensitivity can be obtained.
- the crystallinity is reduced, the solubility in a solvent or the like is improved, and precipitation becomes difficult over time, and the stability over time of the colored composition can be improved.
- bifunctional or trifunctional or higher photoradical polymerization initiators include those described in JP-T-2010-527339, JP-T-2011-524436, WO-2015/004565, JP-T-2016-532675.
- the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 20% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 15% by mass or less, more preferably 10% 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 kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention preferably contains a solvent.
- An organic solvent is mentioned as a solvent.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- Organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For these details, reference can be made to paragraph 0223 of WO2015/166779, the content of which is incorporated herein. Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used.
- organic solvents 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, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (e.g., 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content.
- the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a ppt (parts per trillion) level by mass may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (Chemical Daily, November 13, 2015). .
- Examples of methods for removing impurities such as metals from organic solvents 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, and even more preferably 3 ⁇ m or less.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one isomer may be contained, or a plurality of isomers 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 10-95% by mass, more preferably 20-90% by mass, and even more preferably 30-90% by mass.
- the colored composition of the present invention does not substantially contain environmentally regulated substances.
- substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the colored composition is 50 ppm by mass or less, preferably 30 ppm by mass or less. , is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- Environmental control substances include, for example, benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- distillation off a small amount of environmentally regulated substances it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to increase the efficiency.
- a polymerization inhibitor or the like is added and distilled off under reduced pressure in order to suppress the radical polymerization reaction from progressing during the vacuum distillation and the intermolecular cross-linking.
- These distillation methods are the raw material stage, the reaction product of the raw materials (for example, the resin solution or polyfunctional monomer solution after polymerization), or the colored composition stage produced by mixing these compounds. It is possible at any stage such as
- the coloring composition of the present invention can contain pigment derivatives.
- Pigment derivatives are used, for example, as dispersing aids.
- Pigment derivatives include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
- Dye skeletons constituting pigment derivatives include quinoline dye skeletons, benzimidazolone dye skeletons, benzoisoindole dye skeletons, benzothiazole dye skeletons, iminium dye skeletons, squarylium dye skeletons, croconium dye skeletons, oxonol dye skeletons, and pyrrolopyrrole dye skeletons.
- diketopyrrolopyrrole dye skeleton azo dye skeleton, azomethine dye skeleton, phthalocyanine dye skeleton, naphthalocyanine dye skeleton, anthraquinone dye skeleton, quinacridone dye skeleton, dioxazine dye skeleton, perinone dye skeleton, perylene dye skeleton, thioindigo dye skeleton, Isoindoline dye skeletons, isoindolinone dye skeletons, quinophthalone dye skeletons, iminium dye skeletons, dithiol dye skeletons, triarylmethane dye skeletons, pyrromethene dye skeletons, and the like can be mentioned.
- the acid group includes a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imidic acid group and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
- the carboxylic acid amide group a group represented by —NHCOR X1 is preferable.
- sulfonic acid amide group a group represented by —NHSO 2 R X2 is preferable.
- the imidic acid group is preferably a group represented by —SO 2 NHSO 2 R X3 , —CONHSO 2 R X4 , —CONHCOR X5 or —SO 2 NHCOR X6 , more preferably —SO 2 NHSO 2 R X3 .
- R X1 to R X6 each independently represent an alkyl group or an aryl group.
- the alkyl groups and aryl groups represented by R X1 to R X6 may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
- Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can also be used as the pigment derivative.
- the maximum value ( ⁇ max) of the molar extinction coefficient of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less, and 1000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less. is more preferable, and 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less is even more preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more, and may be 10 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more.
- pigment derivatives include compounds described in JP-A-56-118462, compounds described in JP-A-63-264674, compounds described in JP-A-01-217077, JP-A-03- 009961, compounds described in JP-A-03-026767, compounds described in JP-A-03-153780, compounds described in JP-A-03-045662, JP-A-04-285669 Compounds described in publications, compounds described in JP-A-06-145546, compounds described in JP-A-06-212088, compounds described in JP-A-06-240158, JP-A-10-030063 Compounds described, compounds described in JP-A-10-195326, compounds described in paragraphs 0086 to 0098 of WO 2011/024896, WO 2012/102399 described in paragraphs 0063 to 0094 Compounds, compounds described in paragraph number 0082 of WO 2017/038252, compounds described in paragraph number 0171 of JP 2015-151530, JP 2011-25
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass, based on 100 parts by mass of the specific coloring agent. Further, the total content of the pigment derivative and the colorant is preferably 35% by mass or more, more preferably 40% by mass or more, still more preferably 45% by mass or more, in the total solid content of the coloring composition. More than % by mass is particularly preferred. The upper limit is preferably 70% by mass or less, more preferably 65% by mass or less. Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination.
- the coloring composition of the present invention can also contain a polyalkyleneimine.
- Polyalkyleneimines are used, for example, as dispersing aids for pigments.
- a dispersing aid is a material for enhancing dispersibility of a pigment in a coloring composition.
- a polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine and has at least a secondary amino group.
- the polyalkyleneimine may contain a primary amino group or a tertiary amino group in addition to the secondary amino group.
- the polyalkyleneimine is preferably a polymer having a branched structure each containing a primary amino group, a secondary amino group and a tertiary amino group.
- the alkyleneimine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, still more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
- the molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more.
- the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
- the molecular weight of the polyalkyleneimine when the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is the value calculated from the structural formula.
- the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used.
- the value of the number average molecular weight measured by the viscosity method is used.
- the value of the number average molecular weight in terms of polystyrene measured by the GPC (gel permeation chromatography) method is used.
- the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
- alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine, etc., preferably ethyleneimine or propyleneimine, more preferably ethyleneimine. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. Further, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more, of the primary amino group with respect to the total of the primary amino group, the secondary amino group and the tertiary amino group. , more preferably 30 mol % or more.
- Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by Nippon Shokubai Co., Ltd.).
- the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is more preferably 4.5% by mass or less, even more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is more preferably 0.6 parts by mass or more, still more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a curing accelerator.
- Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
- the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraph numbers 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraph numbers 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200557, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379.
- the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- the coloring composition of the present invention can further contain an infrared absorbing agent.
- an infrared absorbing agent for example, in the case of forming an infrared transmission filter using the coloring composition of the present invention, the wavelength of the light transmitted through the film obtained by containing an infrared absorbing agent in the coloring composition is shifted to the longer wavelength side.
- the infrared absorbing agent is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the wavelength range of 700 nm or more and 1800 nm or less.
- the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less.
- infrared absorbers examples include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
- pyrrolopyrrole compound compounds described in paragraph numbers 0016 to 0058 of JP-A-2009-263614, compounds described in paragraph numbers 0037-0052 of JP-A-2011-068731, International Publication No. 2015/166873 Compounds described in Paragraph Nos. 0010 to 0033 and the like.
- the squarylium compound include compounds described in paragraph numbers 0044 to 0049 of JP-A-2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of WO 2016/181987.
- Examples of croconium compounds include compounds described in JP-A-2017-082029.
- As the iminium compound for example, compounds described in JP-A-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, International Publication No. 2018/043564 and the compounds described in paragraphs 0048 to 0063 of.
- Examples of the phthalocyanine compound include compounds described in paragraph number 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, and paragraph numbers 0013 to 0029 of JP-A-2013-195480. compounds, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, vanadium phthalocyanine compounds described in International Publication No. 2020/071486, and phthalocyanine compounds described in International Publication No. 2020/071470. Examples of naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A-2012-077153. Dithiolene metal complexes include compounds described in Japanese Patent No. 5733804.
- metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- metal borides include lanthanum boride.
- Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.).
- a metal boride the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the infrared absorbing agent the squarylium compound described in JP-A-2017-197437, the squarylium compound described in JP-A-2017-025311, the squarylium compound described in WO 2016/154782, and the patent No. 5884953. No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No.
- the content of the infrared absorbing agent in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is more preferably 2% by mass or more, still more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the upper limit is more preferably 30% by mass or less, and even more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one type of infrared absorbing agent, or may contain two or more types thereof. When two or more kinds of infrared absorbing agents are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, and triazine compounds. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, and paragraph numbers 0317-0317 of JP-A-2013-068814.
- UV absorbers examples include UV-503 (manufactured by Daito Chemical Co., Ltd.), Tinuvin series and Uvinul series manufactured by BASF, and Sumisorb series manufactured by Sumika Chemtex Co., Ltd. .
- Benzotriazole compounds include the MYUA series manufactured by Miyoshi Oil (Kagaku Kogyo Nippo, February 1, 2016).
- the ultraviolet absorber is a compound described in paragraph numbers 0049 to 0059 of Japanese Patent No.
- a thioaryl group-substituted benzotriazole-type ultraviolet absorber described in 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. When two or more kinds 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 polymerization inhibitor.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis(3-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. Only one kind of polymerization inhibitor may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a silane coupling agent.
- a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and capable of forming a siloxane bond by at least one of hydrolysis reaction and condensation reaction.
- Hydrolyzable groups include, for example, halogen atoms, alkoxy groups, acyloxy groups and the like, with alkoxy groups being preferred. 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. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred.
- silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM
- silane coupling agent examples include compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703 and compounds described in paragraph numbers 0056-0066 of JP-A-2009-242604. , the contents of which are incorporated herein.
- the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. Only one type of silane coupling agent may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants and silicone surfactants can be used.
- the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant.
- surfactants reference can be made to surfactants described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
- the fluorine content in the fluorine-based surfactant is preferably 3-40% by mass, more preferably 5-30% by mass, and particularly preferably 7-25% by mass.
- a fluorosurfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and saving liquid, and has good solubility in the coloring composition.
- JP 2014-041318 Paragraph Nos. 0060 to 0064 (corresponding International Publication No. 2014/017669 Paragraph Nos. 0060 to 0064) surfactants described in, JP 2011- Examples include surfactants described in paragraphs 0117 to 0132 of JP-A-132503 and surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
- Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143 and F-144.
- the fluorine-based surfactant has a molecular structure with a functional group containing a fluorine atom, and an acrylic compound in which the functional group containing a fluorine atom is cleaved and the fluorine atom volatilizes when heat is applied is also suitable.
- fluorine-based surfactants include Megafac DS series manufactured by DIC Corporation (Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega Fac DS-21.
- fluorosurfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorosurfactant.
- fluorosurfactants include fluorosurfactants described in JP-A-2016-216602, the contents of which are incorporated herein.
- a block polymer can also be used as the fluorosurfactant.
- the fluorosurfactant has 2 or more (preferably 5 or more) repeating units derived from a (meth)acrylate compound having a fluorine atom and an alkyleneoxy group (preferably an ethyleneoxy group or a propyleneoxy group) (meta).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compound is preferably 3000-50000, for example 14000. In the above compounds, % indicating the ratio of repeating units is mol%.
- a fluoropolymer having an ethylenically unsaturated bond-containing group in a side chain can also be used as the fluorosurfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K.
- compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
- a fluorine-containing imide salt compound represented by formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a+ is an a-valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + .
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF company), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (Fuji
- Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie) and the like.
- a compound having the following structure can also be used as the silicone-based surfactant.
- 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% by mass to 3.0% by mass. Only one type of surfactant may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain an antioxidant.
- Antioxidants include phenol compounds, phosphite ester compounds, thioether compounds and the like. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
- the antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule.
- Phosphorus-based antioxidants can also be suitably used as antioxidants.
- a phosphorus antioxidant tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl ) oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, 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 (manufactured by ADEKA Corporation) and the like.
- antioxidants are compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 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 kind of antioxidant may be used, or two or more kinds thereof may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). Properties such as film physical properties can be adjusted by appropriately containing these components. These components are described, for example, from paragraph number 0183 of JP-A-2012-003225 (paragraph number 0237 of corresponding US Patent Application Publication No. 2013/0034812), paragraph of JP-A-2008-250074 The descriptions of numbers 0101 to 0104, 0107 to 0109, etc.
- auxiliaries e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.
- the colored composition of the present invention may contain a latent antioxidant, if desired.
- the latent antioxidant is a compound in which the site functioning as an antioxidant is protected by a protective group, and is heated at 100 to 250°C, or heated at 80 to 200°C in the presence of an acid/base catalyst.
- a compound that functions as an antioxidant by removing the protecting group by the reaction is exemplified.
- Examples of latent antioxidants include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Commercially available latent antioxidants include ADEKA Arkles GPA-5001 (manufactured by ADEKA Co., Ltd.).
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
- metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 and SiO 2 .
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, even more preferably 5 to 50 nm.
- Metal oxides may have a core-shell structure. Moreover, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improver.
- a light resistance improver compounds described in paragraph numbers 0036 to 0037 of JP-A-2017-198787, compounds described in paragraph numbers 0029-0034 of JP-A-2017-146350, JP-A-2017-129774 Compounds described in paragraph numbers 0036 to 0037, 0049 to 0052 of JP 2017-129674 JP 2017-129674 paragraph numbers 0031 to 0034, 0058 to 0059 compounds described in JP 2017-122803 paragraph numbers 0036 to 0037 , compounds described in 0051 to 0054, compounds described in paragraph numbers 0025 to 0039 of WO 2017/164127, compounds described in paragraph numbers 0034 to 0047 of JP 2017-186546, JP 2015-025116 Compounds described in paragraph numbers 0019 to 0041 of JP-A-2012-145604, compounds described in paragraph numbers 0101-0125 of JP-A-2012-103475, compounds
- the coloring composition of the present invention preferably does not substantially contain terephthalic acid ester.
- substantially free means that the content of terephthalic acid ester is 1000 mass ppb or less in the total amount of the coloring composition, and more preferably 100 mass ppb or less, Zero is particularly preferred.
- perfluoroalkylsulfonic acid and its salts may be regulated.
- perfluoroalkylsulfonic acid especially perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- fluoroalkylcarboxylic acid especially perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- its salt is 0.01ppb to 1,000ppb with respect to the total solid content of the coloring composition.
- the coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts.
- a compound that can substitute for perfluoroalkylsulfonic acid and its salt and a compound that can substitute for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and salts thereof may be selected.
- Examples of compounds that can substitute for regulated compounds include compounds that are excluded from the scope of regulation due to differences in the number of carbon atoms in perfluoroalkyl groups. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
- the coloring composition of the present invention may contain perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts within the maximum permissible range.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface state (such as flatness) and adjusting the film thickness.
- the viscosity value can be appropriately selected as necessary, but is preferably 0.3 mPa ⁇ s to 50 mPa ⁇ s, more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s at 25°C.
- a method for measuring the viscosity for example, a cone-plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25°C.
- the colored composition of the present invention preferably has a chloride ion content of 10000 ppm or less, more preferably 1000 ppm or less, from the viewpoint of environmental friendliness, suppression of foreign matter generation, suppression of equipment contamination, etc. preferable.
- a chloride ion content 10000 ppm or less, more preferably 1000 ppm or less, from the viewpoint of environmental friendliness, suppression of foreign matter generation, suppression of equipment contamination, etc. preferable.
- the use of raw materials with a low chloride ion content, washing with water, ion exchange resin, a method of removing chloride ions by filter filtration, etc. be done.
- a known method can be used as a method for measuring chloride ions, and examples thereof include ion chromatography and combustion ion chromatography.
- the storage container for the coloring composition is not particularly limited, and known storage containers can be used.
- a storage container a multi-layer bottle whose inner wall is composed of 6 types and 6 layers of resins and a bottle with a 7-layer structure of 6 types of resins for the purpose of suppressing the contamination of raw materials and coloring compositions. It is also preferred to use Examples of such a container include the container described in JP-A-2015-123351.
- the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, enhancing the storage stability of the coloring composition, and suppressing deterioration of components.
- the coloring composition of the present invention can be prepared by mixing the aforementioned ingredients.
- all components may be simultaneously dissolved and / or dispersed in a solvent to prepare a coloring composition, and if necessary, each component may be appropriately mixed as two or more solutions or dispersions. , these may be mixed at the time of use (at the time of application) to prepare a colored composition.
- a process of dispersing the pigment when preparing the coloring composition.
- mechanical forces used for dispersing pigments include 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.
- 2015-157893 can be suitably used.
- the particles may be made finer in the salt milling step.
- Materials, equipment, processing conditions, etc. used in the salt milling step can be referred to, for example, Japanese Patent Application Laid-Open Nos. 2015-194521 and 2012-046629.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
- polyamide resins such as nylon (eg nylon-6, nylon-6,6)
- polyolefin resins such as polyethylene and polypropylene (PP) (including high-density, ultra-high-molecular-weight polyolefin resin) and other materials.
- PP polypropylene
- nylon including high density polypropylene
- nylon including high density polypropylene
- the pore size of the filter is preferably 0.01-7.0 ⁇ m, more preferably 0.01-3.0 ⁇ m, and even more preferably 0.05-0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the pore size value of the filter reference can be made to the filter manufacturer's nominal value.
- Various filters provided by Nihon Pall Co., Ltd. (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as the filter. .
- fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
- Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Roki Techno.
- filters When using filters, different filters (eg, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed twice or more. Also, filters with different pore sizes within the range described above may be combined. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration with the second filter may be performed. In addition, the filter can be appropriately selected according to the hydrophilicity/hydrophobicity of the composition.
- the film of the present invention is a film obtained from the coloring composition of the present invention described above.
- the film of the present invention can be used for optical filters such as color filters and infrared transmission filters. Specifically, it can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Green pixels and blue pixels are preferred, and green pixels are more preferred.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose, but is preferably 0.1 to 20 ⁇ m.
- the upper limit of the film thickness is more preferably 10 ⁇ m or less, still more preferably 5 ⁇ m or less, even more preferably 3 ⁇ m or less, and particularly preferably 1.5 ⁇ m or less.
- the lower limit of the film thickness is more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
- the film of the invention can be produced through a step of coating the coloring composition of the invention on a support.
- the film manufacturing method further includes a step of forming a pattern (pixels).
- a method for forming the pattern (pixels) includes a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by photolithography includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, a step of patternwise exposing the colored composition layer, and a step of exposing the colored composition layer. forming a pattern (pixels) by developing and removing the exposed portion. 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 colored composition layer of the present invention is used to form the colored composition layer on the support.
- the support is not particularly limited and can be appropriately selected depending on the application. Examples thereof include glass substrates and silicon substrates, and silicon substrates are preferred. Also, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CCD charge-coupled device
- CMOS complementary metal oxide semiconductor
- the silicon substrate is formed with a black matrix that isolates each pixel.
- the silicon substrate may be provided with an underlying layer for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.
- the underlayer may be formed using a composition obtained by removing the coloring agent from the colored composition described herein, or a composition containing the resin, polymerizable compound, surfactant, etc. described herein. good.
- the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferably 30 to 80° when measured with water.
- a known method can be used as a method for applying the coloring composition.
- dropping method drop cast
- slit coating method spray method
- roll coating method spin coating
- methods described in publications inkjet
- ejection system printing ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc. various printing methods; a transfer method using a mold or the like; and a nanoimprint method.
- the application method for inkjet is not particularly limited.
- the colored composition layer formed on the support may be dried (pre-baked). Pre-baking may not be performed when the film is manufactured by a low-temperature process.
- the pre-baking 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, and can also be 80° C. or higher.
- the pre-bake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Pre-baking can be performed using a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
- Radiation (light) that can be used for exposure includes g-line, i-line, and the like.
- Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
- Light having a wavelength of 300 nm or less includes KrF rays (wavelength: 248 nm), ArF rays (wavelength: 193 nm), etc., and KrF rays (wavelength: 248 nm) are preferable.
- a long-wave light source of 300 nm or more can also be used.
- the light when exposing, the light may be continuously irradiated and exposed, or may be irradiated and exposed in pulses (pulse exposure).
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and rest in short-time (for example, millisecond level or less) cycles.
- the dose is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration at the time of exposure can be selected as appropriate.
- the exposure may be in an oxygen-free atmosphere, or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W/m 2 to 100000 W/m 2 (eg, 5000 W/m 2 , 15000 W/m 2 or 35000 W/m 2 ). can be done.
- the oxygen concentration and exposure illuminance may be appropriately combined.
- the illuminance may be 10000 W/m 2 at an oxygen concentration of 10% by volume and 20000 W/m 2 at an oxygen concentration of 35% by volume.
- the unexposed areas of the colored composition layer are removed by development to form a pattern (pixels).
- the development and removal of the unexposed portion of the colored composition layer can be performed using a developer.
- the unexposed portion of the colored composition layer in the exposure step is eluted into the developer, leaving only the photocured portion.
- the temperature of the developer is preferably 20 to 30° C., for example.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the step of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
- the developer includes an organic solvent, an alkaline developer, etc., and an alkaline developer is preferably used.
- an alkaline developer an alkaline aqueous solution (alkali developer) obtained by diluting an alkaline agent with pure water is preferable.
- alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, 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
- examples include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate and sodium metasilicate.
- a compound having a large molecular weight is preferable for the alkaline agent from the standpoint of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant. From the viewpoint of transportation and storage convenience, the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it can be set, for example, in the range of 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Rinsing is preferably carried out by supplying a rinsing solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinsing liquid from the central portion of the support to the peripheral portion of the support.
- the moving speed of the nozzle may be gradually decreased.
- Additional exposure processing and post-baking are post-development curing treatments for complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 240.degree. C., more preferably 200 to 240.degree.
- Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulating dryer), or a high-frequency heater so that the developed film satisfies the above conditions. .
- the light used for exposure preferably has a wavelength of 400 nm or less.
- the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by a dry etching method is 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 layer; a step of patternwise exposing the photoresist layer and then developing it to form a resist pattern; and etching the cured layer using the resist pattern as a mask. and dry etching using a gas.
- a mode in which heat treatment after exposure and heat treatment (post-baking treatment) after development are performed is desirable.
- pattern formation by a dry etching method descriptions in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and the contents thereof are incorporated herein.
- optical filter of the present invention has the film of the present invention as described above.
- Types of optical filters include color filters and infrared transmission filters, and color filters are preferred.
- a color filter preferably has the film of the present invention as its colored pixels.
- the film thickness of the 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, 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 even more preferably 0.3 ⁇ m or more.
- the width of pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
- the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and even more preferably 0.6 ⁇ m or more.
- the upper limit is more preferably 5.0 ⁇ m or less, still more preferably 2.0 ⁇ m or less, even more preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- Each pixel included in the optical filter preferably has high flatness.
- the pixel surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example.
- the surface roughness of a pixel can be measured using, for example, AFM (Atomic Force Microscope) Dimension 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.).
- the volume resistance value of the pixel is high.
- the volume resistance value of the pixel is preferably 10 9 ⁇ cm or more, more preferably 10 11 ⁇ cm or more.
- the upper limit is not specified, it is preferably 10 14 ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- a protective layer may be provided on the surface of the film of the present invention.
- the protective layer By providing the protective layer, it is possible to impart various functions such as blocking oxygen, reducing reflection, making the film hydrophilic and hydrophobic, and blocking light of a specific wavelength (ultraviolet rays, near-infrared rays, etc.).
- the thickness of the protective layer is preferably 0.01-10 ⁇ m, more preferably 0.1-5 ⁇ m.
- Examples of the method of forming the protective layer include a method of applying a protective layer-forming composition, a chemical vapor deposition method, and a method of adhering a molded resin with an adhesive.
- Components constituting the protective layer include (meth)acrylic resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, and polyimides.
- 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 protective layer contains organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index modifiers, antioxidants, adhesion agents, additives such as surfactants. may contain.
- organic/inorganic fine particles include polymeric fine particles (eg, 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 absorber can be used as the absorber for light of a specific wavelength.
- the content of these additives can be appropriately adjusted, 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 the protective layers described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the solid-state imaging device of the present invention includes the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it functions as a solid-state imaging device.
- a plurality of photodiodes and transfer electrodes made of polysilicon or the like are provided on the substrate, forming the light-receiving area of a solid-state imaging device (CCD (charge-coupled device) image sensor, CMOS (complementary metal-oxide semiconductor) image sensor, etc.). and a device protective film made of silicon nitride or the like formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion. and a color filter on the device protective film.
- CCD charge-coupled device
- CMOS complementary metal-oxide semiconductor
- the color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each color pixel. Examples of imaging devices having such a structure include devices described in JP-A-2012-227478, JP-A-2014-179577, and International Publication No. 2018/043654.
- an ultraviolet absorption layer may be provided in the structure of the solid-state imaging device to improve light resistance.
- An imaging device equipped with the solid-state imaging device of the present invention can be used not only for digital cameras and electronic devices having an imaging function (mobile phones, etc.), but also for vehicle-mounted cameras and monitoring cameras.
- the image display device of the present invention includes the film of the present invention described above.
- image display devices include liquid crystal display devices and organic electroluminescence display devices.
- electroluminescence display devices For a definition of an image display device and details of each image display device, see, for example, “Electronic Display Device (by Akio Sasaki, Industrial Research Institute, 1990)", “Display Device (by Junsho Ibuki, Sangyo Tosho ( Co., Ltd.) issued in 1989).
- Liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied.
- the metal chloride is used in an amount of 1 molar equivalent relative to the squarylium compound, and in the case of compounds (SQ-22) to (SQ-26), 0.5 molar equivalents were used with respect to the squarylium compound, and in the case of compound (SQ-27), 0.33 molar equivalents were used with respect to the squarylium compound for synthesis.
- the squarylium compounds (A-1) to (A-14) used in each synthesis example have the following structures.
- the structures, maximum absorption wavelengths ( ⁇ max) and (M+H) (posi) values of compounds (SQ-1) to (SQ-27) obtained in Synthesis Examples 1 to 27 are as follows.
- dispersion liquid A mixed liquid obtained by mixing raw materials shown in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.1 mm). Then, dispersion treatment was carried out using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a pressure reduction mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersing treatment was repeated 10 times to obtain a dispersion. Numerical values indicating compounding amounts in the table below are parts by mass. In addition, the numerical value of the compounding quantity of a dispersing agent is a numerical value by solid content conversion.
- (dispersant) B-1 Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 24000, acid value: 47 mgKOH/g)
- B-2 Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 16000, acid value: 67 mgKOH/g)
- B-3 Resin having the following structure (the numerical value attached to the main chain is the mass ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 13000, acid value: 65 mgKOH/g)
- Resin B-4 synthesized by the following method A reactor was charged with 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of t-butyl methacrylate, and 45.4 parts by mass of PGMEA (propylene glycol monomethyl ether acetate), and the atmospheric gas was replaced with nitrogen gas. Heat the inside of the reaction vessel to 70° C., add 6 parts by mass of 3-mercapto-1,2-propanediol, add 0.12 parts by mass of AIBN (azobisisobutyronitrile), and react for 12 hours. let me Solid content measurement confirmed that 95% had reacted.
- PGMEA propylene glycol monomethyl ether acetate
- B-6 Resin having the following structure (block copolymer. Numerical values attached to the main chain are mass ratios. Amine value 71 mgKOH/g, weight average molecular weight 9900)
- Surfactant 1 1% by mass PGMEA solution of KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd.).
- (resin) b1 resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 30,000)
- b2 Resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 11,000)
- b3 Resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 10,000)
- ⁇ Evaluation> (Applicability) The coloring composition was applied by spin coating onto an 8 inch (20.32 cm) diameter silicon wafer. Then, using a hot plate, it was heated at 100° C. for 2 minutes. The film thickness of the pre-baked film was measured using a non-contact film thickness meter (FILMMETRICSF-50, manufactured by Matsushita Techno Trading Co., Ltd.). The film thickness was measured at 10 points, the difference ( ⁇ value) between the maximum value and the minimum value of the film thickness was obtained, and the applicability was evaluated according to the following criteria. 4: ⁇ value is less than 20 nm 3: ⁇ value is 20 nm or more and less than 30 nm 2: ⁇ value is 30 nm or more and less than 50 nm 1: ⁇ value is 50 nm or more
- a composition for forming a base layer (CT-4000L, manufactured by FUJIFILM Electronic Materials Co., Ltd.) is applied so that the dry film thickness is 0.1 ⁇ m, After drying, heat treatment was performed at 220° C. for 5 minutes to form an underlayer.
- each coloring composition is applied using a spin coater so that the film thickness after prebaking is 0.6 ⁇ m, and heated using a hot plate at 100 ° C. for 120 seconds. Processing (pre-baking) was performed.
- the silicon wafer after the paddle development is fixed on a horizontal rotary table by a vacuum chuck method, and while the silicon wafer is rotated at a rotation speed of 50 rpm by a rotating device, pure water is sprayed from above the center of rotation in the form of a shower.
- Supply and rinse treatment 23 seconds ⁇ 2 times
- spin drying and then heat treatment (post-baking) using a hot plate at 200 ° C. for 300 seconds to form a colored pattern (pixel). formed.
- the silicon wafer on which the colored pattern (pixels) was formed was observed from above the silicon wafer at a magnification of 30,000 using a critical dimension SEM (scanning electron microscope) (S-7800H, manufactured by Hitachi, Ltd.).
- the distance from the reference line where the edge should be is measured by a length measurement SEM (Hitachi Ltd. S-8840), and any 30 points are measured from 50 ⁇ m in the length direction, the standard deviation is obtained, and 3 ⁇ is calculated. Calculated. A smaller 3 ⁇ value indicates better performance.
- 3 ⁇ is less than 25 nm 4: 3 ⁇ is 25 nm or more and less than 50 nm 3: 3 ⁇ is 50 nm or more and less than 75 nm 2: 3 ⁇ is 75 nm or more and less than 100 nm 1: 3 ⁇ is 100 nm or more
- the examples had less unevenness in thickness than the comparative examples and were superior in coatability. Furthermore, the pattern linearity was also excellent.
- a colorant a structure represented by formula (a-4), formula (a-7), formula (a-8), formula (a-11) or formula (a-12) (with a hydroxy group squarylium dye structure) and the counter cation is Ba cation, Ca cation, Zn cation, Mg cation or Fe cation, coating properties and pattern linearity can be further improved.
- compound (SQ-7) or compound (SQ-8), which is a compound having a structure of formula (a-7) or formula (a-8) as a colorant and having a counter cation of Ba cation, and the oxime compounds ((I-1) to (I-6), (I-11)) as photopolymerization initiators. was excellent.
- the chloride ion content in the coloring composition measured by combustion ion chromatography was 10000 ppm or less.
- dispersion liquid A mixed liquid obtained by mixing raw materials shown in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.1 mm). Then, dispersion treatment was carried out using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a decompression mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersing treatment was repeated 10 times to obtain a dispersion. Numerical values indicating compounding amounts in the following table are parts by mass. In addition, the numerical value of the compounding quantity of a dispersing agent is a numerical value in solid content conversion.
- PY185 C.I. I. Pigment Yellow 185 (isoindoline compound, yellow pigment)
- PY117 C.I. I. Pigment Yellow 117 (azomethine copper complex, yellow pigment)
- PY129 C.I. I. Pigment Yellow 129 (azomethine copper complex, yellow pigment)
- PY138 C.I. I. Pigment Yellow 138 (quinophthalone compound, yellow pigment)
- PY139 C.I. I. Pigment Yellow 139 (isoindoline compound, yellow pigment) PY150: C.I. I.
- Pigment Yellow 150 (azo nickel complex, yellow pigment) Y-1: compound having the following structure (quinophthalone compound, yellow pigment)
- Y-2 compound having the following structure (quinophthalone compound, yellow pigment)
- Y-3 compound having the following structure (azomethine zinc complex, yellow pigment)
- PG7 C.I. I. Pigment Green 7 (copper phthalocyanine complex, green pigment)
- PG36 C.I. I. Pigment Green 36 (copper phthalocyanine complex, green pigment)
- PG58 C.I. I. Pigment Green 58 (zinc phthalocyanine complex, green pigment)
- PG59 C.I. I. Pigment Green 59 (zinc phthalocyanine complex, green pigment)
- PG62 C.I. I.
- Pigment Green 62 (aluminum phthalocyanine complex, green pigment)
- PG63 C.I. I. Pigment Green 63 (aluminum phthalocyanine complex, green pigment)
- PR254 C.I. I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
- PR264 C.I. I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
- PR272 C.I. I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
- PR122 C.I. I. Pigment Red 122 (quinacridone compound, red pigment)
- PV23 C.I. I. Pigment Violet 23 (dioxane compound, purple pigment)
- PB15:6 C.I. I. Pigment Blue 15:6 (copper phthalocyanine complex, blue pigment)
- Example 1001 was prepared in the same manner as in Example 7, except that 560 parts by mass of Dispersion D-7 was changed to 460 parts by mass of Dispersion D-7 and 100 parts by mass of Dispersion d-1. to produce a coloring composition. The resulting colored composition was evaluated for applicability and pattern linearity in the same manner as described above.
- Example 1002-1021 Coloring of Examples 1002 to 1021 in the same manner as in Example 1001 except that 100 parts by mass of dispersion d-1 was changed to 100 parts by mass of dispersions d-2 to d-21 in Example 1001. A composition was produced. The resulting colored composition was evaluated for applicability and pattern linearity in the same manner as described above.
- Example 1022 100 parts by weight of the coloring composition of Example 1001 and 100 parts by weight of the coloring composition of Example 1011 were mixed to prepare the coloring composition of Example 1022.
- the resulting colored composition was evaluated for applicability and pattern linearity in the same manner as described above.
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Abstract
Description
上記着色剤は式(I)で表される化合物を含み、上記式(I)で表される化合物の極大吸収波長が波長500nm以上700nm未満の範囲に存在する、
着色組成物;
Y1は単結合または(l+1)価の連結基を表し、Y1が複数存在する場合、複数のY1は同一であってもよく、異なっていてもよく、
Mp+は対カチオンを表し、
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである。
<2> 上記式(I)のA1が表すスクアリリウム色素構造は、式(sq1)で表される構造である、<1>に記載の着色組成物;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(I)のY1との連結手を含んでいてもよい。
<3> 上記式(sq1)のA11およびA12の少なくとも1つは、式(A1)で表される基である、<2>に記載の着色組成物;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(I)のY1との連結手を表す。
<4> 上記式(I)のMp+はCaカチオン、Baカチオン、Znカチオン、Mgカチオン又はFeカチオンである、<1>~<3>のいずれか1つに記載の着色組成物。
<5> 上記式(I)で表される化合物は、式(III)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;
Y2は単結合または(l+1)価の連結基を表し、Y2が複数存在する場合、複数のY2は同一であってもよく、異なっていてもよい;
Mp+は対カチオンを表す;
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(III)のY2との連結手を含んでいてもよい;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(III)のY2との連結手を表す。
<6> 上記式(III)の-Y2-[COO-]lは、式(Y-1)で表される基である、<5>に記載の着色組成物;
LY1は(l+1)価の連結基を表し、
lは1以上の整数を表し、
*は式(III)のA21またはA22との連結手を表す。
<7> 上記式(I)で表される化合物は、レーキ色素である、<1>~<6>のいずれか1つに記載の着色組成物。
<8> 上記式(I)で表される化合物は、緑色着色剤、マゼンタ色着色剤、紫色着色剤または青色着色剤である、<1>~<7>のいずれか1つに記載の着色組成物。
<9> 上記着色組成物の全固形分中における上記式(I)で表される化合物の含有量が10~60質量%である、<1>~<8>のいずれか1つに記載の着色組成物。
<10> 上記硬化性化合物は、重合性化合物を含む、<1>~<9>のいずれか1つに記載の着色組成物。
<11> 上記硬化性化合物は、樹脂を含む、<1>~<10>のいずれか1つに記載の着色組成物。
<12> 上記樹脂は、酸基を有する樹脂を含む、<11>に記載の着色組成物。
<13> 上記着色剤は、更に上記式(I)で表される化合物と異なる着色剤を含む、<1>~<12>のいずれか1つに記載の着色組成物。
<14> 固体撮像素子用である、<1>~<13>のいずれか1つに記載の着色組成物。
<15> <1>~<14>のいずれか1つに記載の着色組成物から得られる膜。
<16> <15>に記載の膜を有する光学フィルタ。
<17> <15>に記載の膜を有する固体撮像素子。
<18> <15>に記載の膜を有する画像表示装置。
<19> 式(III)で表される化合物;
Y2は単結合または(l+1)価の連結基を表し、Y2が複数存在する場合、複数のY2は同一であってもよく、異なっていてもよい;
Mp+は対カチオンを表す;
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(III)のY2との連結手を含んでいてもよい;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(III)のY2との連結手を表す。
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「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
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、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表す。
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、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、顔料とは、溶剤に対して溶解しにくい着色剤を意味する。
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。
本発明の着色組成物は、着色剤と、硬化性化合物とを含み、
上記着色剤は式(I)で表される化合物を含み、式(I)で表される化合物の極大吸収波長が波長500nm以上700nm未満の範囲に存在することを特徴とする。
(1):波長400~640nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長800~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(2):波長400~750nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長900~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(3):波長400~830nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(4):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(5):波長400~1050nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1200~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(特定着色剤)
本発明の着色組成物は着色剤を含有する。本発明の着色組成物において、着色剤には式(I)で表される化合物を含むものが用いられる。以下、(I)で表される化合物を特定着色剤ともいう。
Y1は単結合または(l+1)価の連結基を表し、Y1が複数存在する場合、複数のY1は同一であってもよく、異なっていてもよく、
Mp+は対カチオンを表し、
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである。
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(I)のY1との連結手を含んでいてもよい。
A11およびA12が表す複素環基は、5員環または6員環の複素環基が好ましい。また、複素環基は、単環の複素環基または縮合数が2~8の縮合環の複素環基が好ましく、単環の複素環基または縮合数が2~4の縮合環の複素環基がより好ましく、単環の複素環基または縮合数が2または3の縮合環の複素環基が更に好ましい。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ヘテロ原子の数は、1~3が好ましく、1~2がより好ましい。複素環基の環を構成する炭素原子の数は1~30が好ましく、1~18がより好ましく、1~12が更に好ましい。
アリール基および複素環基は、置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。また、アリール基および複素環基は、式(I)のY1との連結手を含んでいてもよい。アリール基は、後述する式(A1)で表される基であることが好ましい。
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(I)のY1との連結手を表す。
Ra1~Ra5が表すアルキル基の炭素数は、1~20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い。Ra1~Ra5が表すアルキル基は置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
Ra1~Ra5が表すアルコキシ基の炭素数は、1~20が好ましく、1~15がより好ましく、1~8が更に好ましい。アルコキシ基は、直鎖および分岐のいずれでもよい。Ra1~Ra5が表すアルコキシ基は置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
Ra1~Ra5が表すアリール基の炭素数は、6~48が好ましく、6~22がより好ましく、6~12が特に好ましい。Ra1~Ra5が表すアリール基は置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
Ra1~Ra5が表す複素環基としては上述した複素環基が挙げられ、好ましい範囲も同様である。Ra1~Ra5が表す複素環基は置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
Ra1~Ra5が表すアミノ基としては、-NRa101Ra102で表される基が挙げられる。-NRa101Ra102で表される基において、Ra101およびRa102は、それぞれ独立して、水素原子、アルキル基及びアリール基を表し、アルキル基であることが好ましい。アルキル基の炭素数は、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。アルキル基は、直鎖、分岐、環状のいずれでもよいが、直鎖または分岐が好ましく、直鎖がより好ましい。アルキル基は、置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。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。アリール基は、置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
また、式(A1)のRa2、Ra3、およびRa4は、それぞれ独立して、水素原子、アミノ基または式(I)のY1との連結手であることが好ましく、Ra2およびRa4が水素原子で、Ra3がアミノ基または式(I)のY1との連結手であることがより好ましい。
(1)脂肪族炭化水素基
(2)芳香族炭化水素基
(3)芳香族炭化水素基と、脂肪族炭化水素基との組み合わせからなる基
(4)脂肪族炭化水素基と、-O-または-S-との組み合わせからなる基
(5)芳香族炭化水素基と、-O-または-S-との組み合わせからなる基
(6)芳香族炭化水素基と、脂肪族炭化水素基と、-O-または-S-との組み合わせからなる基との組み合わせからなる基
(7)-NRY-と、脂肪族炭化水素基との組み合わせからなる基
(8)-NRY-と、芳香族炭化水素基との組み合わせからなる基
(9)-NRY-と、脂肪族炭化水素基と、芳香族炭化水素基との組み合わせからなる基
(10)-NRY-と、脂肪族炭化水素基と、-O-または-S-との組み合わせからなる基
(11)-NRY-と、芳香族炭化水素基と、-O-または-S-との組み合わせからなる基
(12)-NRY-と、脂肪族炭化水素基と、芳香族炭化水素基と、-O-または-S-との組み合わせからなる基
(13)-NRYCO-と、脂肪族炭化水素基との組み合わせからなる基
(14)-NRYCO-と、芳香族炭化水素基との組み合わせからなる基
(15)-NRYCO-と、脂肪族炭化水素基と、芳香族炭化水素基との組み合わせからなる基
lは1~4であることが好ましく、1~3であることがより好ましく、1または2であることが更に好ましい。
mは1~4であることが好ましく、1~3であることがより好ましく、1または2であることが更に好ましい。
nは1~5であることが好ましく、1~4であることがより好ましく、1~3であることが更に好ましい。
Y2は単結合または(l+1)価の連結基を表し、Y2が複数存在する場合、複数のY2は同一であってもよく、異なっていてもよい;
Mp+は対カチオンを表す;
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(III)のY2との連結手を含んでいてもよい;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(III)のY2との連結手を表す。
式(III)のA21およびA22が表す複素環基は、式(sq1)で表される構造におけるA11およびA12が表す複素環基と同義である。
式(III)のA21およびA22が表す式(R1)で表される基におけるRs1~Rs3、As3およびns1は、式(sq1)で表される構造におけるA11およびA12が表すものとして説明した式(R1)で表される基におけるRs1~Rs3、As3およびns1と同義である。
式(III)のA21およびA22が表す式(A1)で表される基におけるRa1~Ra5は、式(sq1)で表される構造におけるA11およびA12が表すものとして説明した式(A1)で表される基におけるRa1~Ra5と同義である。
式(III)のY2が表す(l+1)価の連結基は、式(I)のY1が表す(l+1)価の連結基と同義である。
式(III)のMp+が表す対カチオンは、式(I)のMp+が表す対カチオンと同義である。
式(III)のl、m、n、pおよびqは、式(I)のl、m、n、pおよびqと同義である。
LY1は(l+1)価の連結基を表し、
lは1以上の整数を表し、
*は式(III)のA21またはA22との連結手を表す。
本発明の着色組成物に含まれる着色剤は、上記特定着色剤とは異なる着色剤(他の着色剤)をさらに含有することができる。併用する他の着色剤としては、有彩色着色剤、および、黒色着色剤などが挙げられる。有彩色着色剤としては、波長400~700nmの範囲に極大吸収波長を有する着色剤が挙げられる。例えば、緑色着色剤、赤色着色剤、黄色着色剤、紫色着色剤、青色着色剤、オレンジ色着色剤などが挙げられる。他の着色剤は、有彩色着色剤であることが好ましく、黄色着色剤および緑色着色剤から選ばれる少なくとも1種であることが好ましく、黄色着色剤であることがより好ましい。他の着色剤は、顔料であってもよく、染料であってもよいが、顔料であることが好ましい。
また、黄色着色剤の含有量は特定着色剤の100質量部に対して1~50質量部であることが好ましい。上限は45質量部以下であることがより好ましく、40質量部以下であることが更に好ましい。下限は5質量部以上であることがより好ましく、10質量部以上であることが更に好ましい。
本発明の着色組成物は硬化性化合物を含有する。硬化性化合物としては、重合性化合物、樹脂等が挙げられる。樹脂は、非重合性の樹脂(重合性基を有さない樹脂)であってもよく、重合性の樹脂(重合性基を有する樹脂)であってもよい。重合性基としては、エチレン性不飽和結合含有基および環状エーテル基などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられ、エポキシ基が好ましい。エポキシ基は、脂環式エポキシ基であってもよい。なお、脂環式エポキシ基とは、エポキシ環と飽和炭化水素環とが縮合した環状構造を有する1価の官能基のことを意味する。
重合性化合物としては、エチレン性不飽和結合含有基を有する化合物および環状エーテル基を有する化合物等が挙げられる。エチレン性不飽和結合含有基を有する化合物はラジカル重合性化合物として好ましく用いることができる。また、環状エーテル基を有する化合物は、カチオン重合性化合物として好ましく用いることができる。
本発明の着色組成物は、硬化性化合物として樹脂を用いることができる。硬化性化合物は、樹脂を少なくとも含むものを用いることが好ましい。樹脂は、例えば、顔料等を着色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、主に顔料等を着色組成物中で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を目的として樹脂を使用することもできる。なお、重合性基を有する樹脂は、重合性化合物にも該当する。
式(Ac-2)中、Ar10は芳香族カルボキシ基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
式(Ar-11)~(Ar-13)中、*1はL1との結合位置を表す。
また、酸基を有する樹脂の含有量は、着色組成物の全固形分中1~70質量%であることが好ましい。下限は、2質量%以上であることがより好ましく、3質量%以上であることが更に好ましく、5質量%以上であることが更により好ましい。上限は、65質量%以下であることがより好ましく、60質量%以下であることが更に好ましい。
また、アルカリ可溶性樹脂の含有量は、着色組成物の全固形分中1~70質量%であることが好ましい。下限は、2質量%以上であることがより好ましく、3質量%以上であることが更に好ましく、5質量%以上であることが更により好ましい。上限は、65質量%以下であることがより好ましく、60質量%以下であることが更に好ましい。
本発明の着色組成物が分散剤としての樹脂を含有する場合、分散剤としての樹脂の含有量は、着色組成物の全固形分中0.1~30質量%が好ましい。上限は、25質量%以下がより好ましく、20質量%以下が更に好ましい。下限は、0.5質量%以上がより好ましく、1質量%以上が更に好ましい。また、分散剤としての樹脂の含有量は、上述した特定着色剤100質量部に対して、1~100質量部が好ましい。上限は、80質量部以下であることがより好ましく、70質量部以下であることが更に好ましく、60質量部以下であることが更により好ましい。下限は、5質量部以上であることがより好ましく、10質量部以上であることが更に好ましく、20質量部以上であることが更により好ましい。
本発明の着色組成物は、樹脂を、1種のみ含んでいてもよいし、2種以上含んでいてもよい。樹脂を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は光重合開始剤を含有することができる。硬化性化合物として重合性モノマーを用いた場合には、本発明の着色組成物は光重合開始剤を含有することが好ましい。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。
RX2は、アルキル基、アルケニル基、アルコキシ基、アリール基、アリールオキシ基、複素環基、複素環オキシ基、アルキルスルファニル基、アリールスルファニル基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、アシルオキシ基またはアミノ基を表し、
RX3~RX14は、それぞれ独立して水素原子または置換基を表す;
ただし、RX10~RX14のうち少なくとも一つは、電子求引性基である。
本発明の着色組成物において、光重合開始剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は、溶剤を含有することが好ましい。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や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も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、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、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、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機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)。
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。顔料誘導体は例えば分散助剤として用いられる。顔料誘導体としては、色素骨格に酸基または塩基性基が結合した構造を有する化合物が挙げられる。
本発明の着色組成物は、ポリアルキレンイミンを含有することもできる。ポリアルキレンイミンは例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。ポリアルキレンイミンとは、アルキレンイミンを開環重合したポリマーであって、2級アミノ基を少なくとも有するポリマーである。ポリアルキレンイミンは、2級アミノ基の他に、1級アミノ基や3級アミノ基を含んでいてもよい。ポリアルキレンイミンは、1級アミノ基と、2級アミノ基と、3級アミノ基とをそれぞれ含む分岐構造を有するポリマーであることが好ましい。アルキレンイミンの炭素数は2~6が好ましく、2~4がより好ましく、2または3であることが更に好ましく、2であることが特に好ましい。
本発明の着色組成物は、硬化促進剤を含有することができる。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2018/056189号の段落番号0094~0097に記載の化合物、特開2015-034963号公報の段落番号0246~0253に記載の化合物、特開2013-041165号公報の段落番号0186~0251に記載の化合物、特開2014-055114号公報に記載のイオン性化合物、特開2012-150180号公報の段落番号0071~0080に記載の化合物、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物、特許第5765059号公報の段落番号0085~0092に記載の化合物、特開2017-036379号公報に記載のカルボキシ基含有エポキシ硬化剤などが挙げられる。着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%であることが好ましく、0.8~6.4質量%であることがより好ましい。
本発明の着色組成物は、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。
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。紫外線吸収剤としては、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が挙げられる。このような化合物の具体例としては、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)、BASF社製のTinuvinシリーズ、Uvinul(ユビナール)シリーズ、住化ケムテックス(株)製のSumisorbシリーズなどが挙げられる。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、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物、国際公開第2016/181987号の段落番号0059~0076に記載された化合物、国際公開第2020/137819号に記載されたチオアリール基置換ベンゾトリアゾール型紫外線吸収剤を用いることもできる。着色組成物の全固形分中における紫外線吸収剤の含有量は、0.01~10質量%であることが好ましく、0.01~5質量%であることがより好ましい。紫外線吸収剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
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%であることが好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、それらの合計量が上記範囲となることが好ましい。
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。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、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-603)、N-β-アミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-903)、3-メタクリロキシプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-502)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-503)等がある。また、シランカップリング剤の具体例については、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。着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%であることが好ましく、0.05~10.0質量%であることがより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、それらの合計量が上記範囲となることが好ましい。
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。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。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を参照することができ、この内容は本明細書に組み込まれる。
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、韓国公開特許第10-2019-0059371号公報に記載された化合物を使用することもできる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
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、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。
本発明の着色組成物は、環境対応、異物発生の抑制、装置汚染の抑制などの観点から、着色組成物中の塩化物イオン量が10000ppm以下であることが好ましく、1000ppm以下であることがより好ましい。着色組成物中の塩化物イオンを上記範囲とするためには、塩化物イオン含有量が少ない原料を使用すること、水洗、イオン交換樹脂、フィルタろ過などで塩化物イオンを除去する方法などが挙げられる。塩化物イオンの測定方法としては公知の方法を使用でき、例えば、イオンクロマトグラフィー、燃焼イオンクロマトグラフィーなどが挙げられる。
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、容器内壁は、容器内壁からの金属溶出を防ぎ、着色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は、前述の成分を混合して調製できる。着色組成物の調製に際しては、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調製してもよいし、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調製してもよい。
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタや赤外線透過フィルタなどの光学フィルタなどに用いることができる。特に具体的には、カラーフィルタの着色画素として好ましく用いることができる。着色画素としては、赤色画素、緑色画素、青色画素、マゼンタ色画素、シアン色画素、黄色画素などが挙げられ、緑色画素、青色画素であることが好ましく、緑色画素であることが更に好ましい。
本発明の膜は、本発明の着色組成物を支持体に塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタなどが挙げられ、カラーフィルタであることが好ましい。カラーフィルタは、その着色画素として本発明の膜を有することが好ましい。
本発明の固体撮像素子は、上述した本発明の膜を含む。固体撮像素子の構成としては、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。
本発明の画像表示装置は、上述した本発明の膜を含む。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。
スクアリリウム化合物および金属塩化物をそれぞれ下記表に示す化合物に変更し、合成例1と同様の操作を実施し、化合物(SQ-2)~化合物(SQ-27)を合成した。なお、金属塩化物は、化合物(SQ-2)~化合物(SQ-21)の場合は、スクアリリウム化合物に対して1モル当量用い、化合物(SQ-22)~(SQ-26)の場合は、スクアリリウム化合物に対して0.5モル当量用い、化合物(SQ-27)に場合はスクアリリウム化合物に対して0.33モル当量用いて合成した。
また、化合物(SQ-1)~化合物(SQ-27)の23℃のプロピレングリコールモノメチルエーテルの100gに対する溶解量は0.5g以下であった。
また、化合物(SQ-1)~化合物(SQ-27)は緑色に近い色相を呈しており、緑色着色剤として好ましい分光特性を有していた。
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm2および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。下記表に記載の配合量を示す数値は質量部である。なお、分散剤の配合量の数値は、固形分換算での数値である。
SQ-1~SQ-27:上述した化合物(SQ-1)~化合物(SQ-27)
A-1:上述したスクアリリウム化合物(A-1)
メチルメタクリレート50質量部、n-ブチルメタクリレート30質量部、t-ブチルメタクリレート20質量部、PGMEA(プロピレングリコールモノメチルエーテルアセテート)45.4質量部を反応容器に仕込み、雰囲気ガスを窒素ガスで置換した。反応容器内を70℃に加熱して、3-メルカプト-1,2-プロパンジオール6質量部を添加して、さらにAIBN(アゾビスイソブチロニトリル)0.12質量部を加え、12時間反応させた。固形分測定により95%が反応したことを確認した。次に、ピロメリット酸無水物9.7質量部、PGMEA70.3質量部、触媒としてDBU(1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン)0.20質量部を追加し、120℃で7時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認し反応を終了した。PGMEAを加えて不揮発分(固形分濃度)を30質量%に調整し、酸価43mgKOH/g、重量平均分子量9000の下記構造の樹脂B-4の樹脂溶液を得た。
S-1: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)
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
下記表に記載の分散液と、下記表に記載の重合性化合物と、下記表に記載の光重合開始剤と、下記表に記載の樹脂と、エポキシ化合物(EHPE-3150、(株)ダイセル製)の1質量部と、紫外線吸収剤(TINUVIN326、BASF社製)の1質量部と、以下に示す界面活性剤1の1質量部と、重合禁止剤(p-メトキシフェノール)の0.1質量部とを混合して着色組成物を製造した。
D-1~D-38、DH-1:上述した分散液D-1~D-38、DH-1
M-1:KAYARAD DPHA(日本化薬(株)製)
M-2:NKエステル A-DPH-12E(新中村化学工業(株)製)
M-3:NKエステル A-TMMT(新中村化学工業(株)製)
M-4: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
M-5:ジペンタエリスリトールヘキサアクリレート
b1:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量30000)
(塗布性)
着色組成物を、直径8インチ(20.32cm)のシリコンウエハ上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。プリベークした後の膜の膜厚を、非接触式膜厚計(FILMMETRICSF-50、松下テクノトレーディング社製)を用いて測定した。膜厚は10箇所測定し、膜厚の最大値と最小値との差(Δ値)を求め、以下の基準で塗布性を評価した。
4:Δ値が20nm未満である
3:Δ値が20nm以上30nm未満である
2:Δ値が30nm以上50nm未満である
1:Δ値が50nm以上である
直径8インチ(20.32cm)のシリコンウエハ上に、乾燥膜厚が0.1μmとなるように下地層形成用組成物(CT-4000L、富士フイルムエレクトロニクスマテリアルズ(株)製)を塗布し、乾燥した後、220℃で5分間加熱処理を行い、下地層を形成した。
次に、下地層を形成したシリコンウエハ上に、各着色組成物をプリベーク後の膜厚が0.6μmとなるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間加熱処理(プリベーク)を行った。次いで、線幅2μmの1:1ラインアンドスペースに配列されたマスクパターンを介して、i線ステッパー露光装置(FPA-3000i5+、Canon(株)製)を使用して365nmの波長の光を500mJ/cm2の露光量で照射して露光した。露光後の膜を有するシリコンウエハを、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、アルカリ現像液(CD-2060、富士フイルムエレクトロニクスマテリアルズ(株)製)を用いて23℃で60秒間パドル現像した。次いで、パドル現像後のシリコンウエハを、真空チャック方式で水平回転テーブルに固定し、回転装置によってシリコンウエハを回転数50rpmで回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理(23秒×2回)を行い、次いで、スピン乾燥を行い、次いで、200℃で300秒間、ホットプレートを用いて加熱処理(ポストベーク)を行い、着色パターン(画素)を形成した。着色パターン(画素)が形成されたシリコンウエハについて、測長SEM(走査型電子顕微鏡)(S-7800H、(株)日立製作所製)を用いてシリコンウエハ上から30000倍の倍率で観察した。着色パターンのエッジについて、エッジのあるべき基準線からの距離を測長SEM((株)日立製作所S-8840)により、長さ方向50μmから任意の30ポイント測定し、標準偏差を求め、3σを算出した。3σの値が小さいほど良好な性能であることを示す。
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm2および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。下記表に記載の配合量を示す数値は質量部である。なお、分散剤の配合量の数値は、固形分換算での数値である。
PY185:C.I.ピグメントイエロー185(イソインドリン化合物、黄色顔料)
PY117:C.I.ピグメントイエロー117(アゾメチン銅錯体、黄色顔料)
PY129:C.I.ピグメントイエロー129(アゾメチン銅錯体、黄色顔料)
PY138:C.I.ピグメントイエロー138(キノフタロン化合物、黄色顔料)
PY139:C.I.ピグメントイエロー139(イソインドリン化合物、黄色顔料)
PY150:C.I.ピグメントイエロー150(アゾニッケル錯体、黄色顔料)
Y-1:下記構造の化合物(キノフタロン化合物、黄色顔料)
Y-2:下記構造の化合物(キノフタロン化合物、黄色顔料)
Y-3:下記構造の化合物(アゾメチン亜鉛錯体、黄色顔料)
PG36:C.I.ピグメントグリーン36(銅フタロシアニン錯体、緑色顔料)
PG58:C.I.ピグメントグリーン58(亜鉛フタロシアニン錯体、緑色顔料)
PG59:C.I.ピグメントグリーン59(亜鉛フタロシアニン錯体、緑色顔料)
PG62:C.I.ピグメントグリーン62(アルミニウムフタロシアニン錯体、緑色顔料)
PG63:C.I.ピグメントグリーン63(アルミニウムフタロシアニン錯体、緑色顔料)
PR254:C.I.ピグメントレッド254(ジケトピロロピロール化合物、赤色顔料)
PR264:C.I.ピグメントレッド264(ジケトピロロピロール化合物、赤色顔料)
PR272:C.I.ピグメントレッド272(ジケトピロロピロール化合物、赤色顔料)
PR122:C.I.ピグメントレッド122(キナクリドン化合物、赤色顔料)
PV23:C.I.ピグメントバイオレット23(ジオキサン化合物、紫色顔料)
PB15:6 :C.I.ピグメントブルー15:6(銅フタロシアニン錯体、青色顔料)
B-1:上述した分散剤B-1
S-1:PGMEA
実施例7において、分散液D-7の560質量部を、分散液D-7の460質量部、分散液d-1の100質量部に変更した以外は実施例7と同様にして実施例1001の着色組成物を製造した。得られた着色組成物について、上記と同様にして塗布性およびパターン直線性を評価したところ、塗布性の評価は4で、パターン直線性の評価は5であった。
実施例1001において、分散液d-1の100質量部を、分散液d-2~分散液d-21の100質量部に変更した以外は実施例1001と同様にして実施例1002~1021の着色組成物を製造した。得られた着色組成物について、上記と同様にして塗布性およびパターン直線性を評価したところ、塗布性の評価は4で、パターン直線性の評価は5であった。
実施例1001の着色組成物の100質量部と、実施例1011の着色組成物の100質量部とを混合して実施例1022の着色組成物を製造した。得られた着色組成物について、上記と同様にして塗布性およびパターン直線性を評価したところ、塗布性の評価は4で、パターン直線性の評価は5であった。
Claims (19)
- 前記式(I)のA1が表すスクアリリウム色素構造は、式(sq1)で表される構造である、請求項1に記載の着色組成物;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(I)のY1との連結手を含んでいてもよい。 - 前記式(I)のMp+はCaカチオン、Baカチオン、Znカチオン、Mgカチオン又はFeカチオンである、請求項1~3のいずれか1項に記載の着色組成物。
- 前記式(I)で表される化合物は、式(III)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;
Y2は単結合または(l+1)価の連結基を表し、Y2が複数存在する場合、複数のY2は同一であってもよく、異なっていてもよい;
Mp+は対カチオンを表す;
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(III)のY2との連結手を含んでいてもよい;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(III)のY2との連結手を表す。 - 前記式(I)で表される化合物は、レーキ色素である、請求項1~6のいずれか1項に記載の着色組成物。
- 前記式(I)で表される化合物は、緑色着色剤、マゼンタ色着色剤、紫色着色剤または青色着色剤である、請求項1~7のいずれか1項に記載の着色組成物。
- 前記着色組成物の全固形分中における前記式(I)で表される化合物の含有量が10~60質量%である、請求項1~8のいずれか1項に記載の着色組成物。
- 前記硬化性化合物は、重合性化合物を含む、請求項1~9のいずれか1項に記載の着色組成物。
- 前記硬化性化合物は、樹脂を含む、請求項1~10のいずれか1項に記載の着色組成物。
- 前記樹脂は、酸基を有する樹脂を含む、請求項11に記載の着色組成物。
- 前記着色剤は、更に前記式(I)で表される化合物と異なる着色剤を含む、請求項1~12のいずれか1項に記載の着色組成物。
- 固体撮像素子用である、請求項1~13のいずれか1項に記載の着色組成物。
- 請求項1~14のいずれか1項に記載の着色組成物から得られる膜。
- 請求項15に記載の膜を有する光学フィルタ。
- 請求項15に記載の膜を有する固体撮像素子。
- 請求項15に記載の膜を有する画像表示装置。
- 式(III)で表される化合物;
Y2は単結合または(l+1)価の連結基を表し、Y2が複数存在する場合、複数のY2は同一であってもよく、異なっていてもよい;
Mp+は対カチオンを表す;
l、m、nおよびqは、それぞれ独立して1以上の整数を表し、
pは2以上の整数を表し、
l×m×n=p×qである;
Rs1~Rs3は、それぞれ独立して水素原子またはアルキル基を表し、
As3は複素環基を表し、
ns1は、0以上の整数を表し、
Rs1とRs2は、互いに結合して環を形成してもよく、
Rs1とAs3は、互いに結合して環を形成してもよく、
Rs2とRs3は、互いに結合して環を形成してもよく、
ns1が2以上の場合、複数のRs2およびRs3はそれぞれ同一であってもよく、異なっていてもよく、
Rs1、Rs2、Rs3およびAs3から選ばれる少なくとも1つは、式(III)のY2との連結手を含んでいてもよい;
Ra1~Ra5はそれぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、複素環基、アミノ基または式(III)のY2との連結手を表す。
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JP2019163233A (ja) * | 2018-03-16 | 2019-09-26 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 化合物 |
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