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WO2024171839A1 - Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image - Google Patents

Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Download PDF

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Publication number
WO2024171839A1
WO2024171839A1 PCT/JP2024/003388 JP2024003388W WO2024171839A1 WO 2024171839 A1 WO2024171839 A1 WO 2024171839A1 JP 2024003388 W JP2024003388 W JP 2024003388W WO 2024171839 A1 WO2024171839 A1 WO 2024171839A1
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Prior art keywords
group
coloring composition
mass
compound
resin
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PCT/JP2024/003388
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English (en)
Japanese (ja)
Inventor
亮祐 加藤
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2025501052A priority Critical patent/JPWO2024171839A1/ja
Publication of WO2024171839A1 publication Critical patent/WO2024171839A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a coloring composition containing a diketopyrrolopyrrole compound.
  • the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device that use the coloring composition.
  • Color filters are used as key devices in displays and optical elements. Color filters usually have pixels of the three primary colors, red, green, and blue, and serve to separate transmitted light into the three primary colors.
  • the colored pixels of each color of the color filter are produced using a coloring composition containing a colorant.
  • the coloring composition for forming red pixels contains a diketopyrrolopyrrole compound as a colorant.
  • Patent Document 1 describes a coloring composition containing a brominated diketopyrrolopyrrole pigment and an alkali-soluble resin.
  • Diketopyrrolopyrrole compounds have a high cohesive force. For this reason, coloring compositions using diketopyrrolopyrrole compounds as colorants tend to have the diketopyrrolopyrrole compounds aggregate during storage, resulting in the formation of aggregated foreign matter, and there is a demand for improved storage stability.
  • Patent Document 1 The inventors have studied the coloring composition disclosed in Patent Document 1 and found that there is room for further improvement in terms of storage stability.
  • an object of the present invention is to provide a coloring composition having excellent storage stability. Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, and an image display device.
  • the present invention provides the following:
  • a coloring composition comprising a colorant, a resin, and a solvent,
  • the colorant comprises a coloring composition comprising a compound represented by formula (1);
  • R 1 and R 2 each independently represent a hydrogen atom or a substituent.
  • R3 represents a substituent;
  • Plural R 1 , R 2 and R 3 may be the same or different;
  • L1 represents an m-valent linking group;
  • m represents an integer of 2 to 6.
  • ⁇ 3> The colored composition according to ⁇ 1> or ⁇ 2>, wherein R 3 in the formula (1) is an aryl group.
  • ⁇ 4> The colored composition according to any one of ⁇ 1> to ⁇ 3>, in which L 1 in the formula (1) is a group containing an aromatic ring.
  • L 1 in the formula (1) is a group containing an aromatic ring.
  • ⁇ 5> The colored composition according to any one of ⁇ 1> to ⁇ 3>, in which L 1 in the formula (1) contains 1 to 4 benzene rings.
  • ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, further comprising a yellow colorant.
  • ⁇ 7> The coloring composition according to any one of ⁇ 1> to ⁇ 6>, in which the colorant further includes at least one selected from Color Index Pigment Red 254, Color Index Pigment Red 255, Color Index Pigment Red 264, Color Index Pigment Red 272, Color Index Pigment Red 291, Color Index Pigment Orange 71, Color Index Pigment Orange 73, and Color Index Pigment Orange 81.
  • the colorant is a compound other than the compound represented by formula (1) and includes a compound having a dye structure and at least one group selected from an acid group, a basic group, and a phthalimido group.
  • ⁇ 12> A film obtained by using the colored composition according to any one of ⁇ 1> to ⁇ 11>.
  • ⁇ 14> A solid-state imaging device having the film according to ⁇ 12>.
  • ⁇ 15> An image display device comprising the film according to ⁇ 12>.
  • the present invention can provide a coloring composition having excellent storage stability.
  • the present invention can also provide a film, an optical filter, a solid-state imaging device, and an image display device.
  • alkyl group encompasses not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups).
  • exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams.
  • Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, active rays or radiation such as electron beams.
  • (meth)acrylate refers to both or either of acrylate and methacrylate
  • (meth)acrylic refers to both or either of acrylic and methacrylic
  • (meth)acryloyl refers to both or either of acryloyl and methacryloyl.
  • Me 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 values calculated as polystyrene standards measured by GPC (gel permeation chromatography).
  • the total solids content refers to the total mass of all components of the composition excluding the solvent.
  • a pigment means a compound that is poorly soluble in a solvent.
  • the term "process” refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the process achieves its intended effect.
  • the coloring composition of the present invention is a coloring composition containing a colorant, a resin, and a solvent,
  • the colorant is characterized by containing a compound represented by formula (1).
  • the coloring composition of the present invention has excellent storage stability, and even when the coloring composition is used after long-term storage, it can form a film in which the generation of foreign matter is suppressed. It is presumed that the compound represented by formula (1) has 2 to 6 structures represented by formula (1a) in one molecule, and thus the crystallinity is reduced, thereby suppressing the generation of aggregated foreign matter during storage.
  • R 1 to R 3 in formula (1a) are synonymous with R 1 to R 3 in formula (1).
  • * in formula (1a) is a bond.
  • the coloring composition of the present invention when used to form a pattern by photolithography, the generation of development residues can also be suppressed.
  • the coloring composition of the present invention when used for forming a pattern by photolithography, it is preferable that the coloring composition of the present invention contains a polymerizable compound and a photopolymerization initiator.
  • the coloring composition of the present invention contains a polymerizable compound and a photopolymerization initiator.
  • a resin that contains a resin having an acid group as the resin.
  • the colored composition of the present invention can be preferably used as a colored composition for optical filters.
  • optical filters include color filters and infrared transmission filters. That is, the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters, and more 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 or a coloring composition for forming an infrared transmission filter, and more preferably used as a coloring composition for forming pixels of a color filter.
  • the types of pixels in a color filter include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, and the like, and red pixels are more preferable.
  • the coloring composition of the present invention contains a colorant.
  • the colorant include a yellow colorant, an orange colorant, a red colorant, a green colorant, a purple colorant, and a blue colorant.
  • the colorant may be a pigment or a dye.
  • the pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoints of a wide range of color variations, ease of dispersion, safety, and the like.
  • a pigment derivative may be used as the colorant.
  • the pigment derivative include a compound having a dye structure and at least one group selected from an acid group, a basic group, and a phthalimide group. When a colorant containing a pigment is used, it is preferable to use a colorant containing a pigment and a pigment derivative.
  • the colorant contained in the coloring composition of the present invention preferably contains a red colorant, and more preferably contains a red colorant and a yellow colorant.
  • the colorant contained in the coloring composition of the present invention preferably contains a red pigment and a yellow pigment, and more preferably contains a red pigment, a yellow pigment, and a pigment derivative.
  • the average primary particle diameter of the pigment and pigment derivative is preferably 1 to 200 nm.
  • the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
  • the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
  • the primary particle diameter of the pigment and pigment derivative can be determined from a photograph obtained by observing the primary particles of the pigment and pigment derivative with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
  • the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 primary particles of the pigment.
  • the primary particles of the pigment refer to independent particles that are not aggregated. The same applies to the average primary particle diameter of the pigment derivative.
  • the crystallite size of the pigment or pigment derivative determined from the half-width of a peak derived from any crystal plane in the X-ray diffraction spectrum when CuK ⁇ radiation is used as the X-ray source, is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
  • the specific surface area of the pigment and pigment derivative is preferably 1 to 300 m 2 /g.
  • the lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more.
  • the upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less.
  • the value of the specific surface area can be measured according to DIN 66131: determination of the specific surface area of solids by gas adsorption in accordance with the BET (Brunauer, Emmett and Teller) method.
  • the colorant contained in the colored composition of the present invention contains a compound represented by formula (1).
  • the compound represented by formula (1) is also referred to as a specific compound.
  • R 1 and R 2 each independently represent a hydrogen atom or a substituent.
  • a plurality of R 1 and R 2 may be the same or different.
  • the substituent represented by R1 and R2 include the substituent T described below and a group represented by formula (R-100) described below.
  • the substituent is preferably an alkyl group, an aryl group or a heteroaryl group, and more preferably an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent or may be unsubstituted.
  • the substituent include the substituent T described below and a group represented by formula (R-100) described below.
  • the number of carbon atoms in the aryl group is preferably 6 to 20, and more preferably 6 to 12.
  • the aryl group may have a substituent or may be unsubstituted.
  • Examples of the substituent include the substituent T described later and a group represented by formula (R-100) described later.
  • the number of carbon atoms constituting the heteroaryl ring of the heteroaryl group is preferably 1 to 30, more preferably 1 to 12. Examples of the types of heteroatoms constituting the heteroaryl ring include nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the number of heteroatoms constituting the heteroaryl ring is preferably 1 to 3, more preferably 1 to 2.
  • the heteroaryl ring is preferably a monocyclic ring or a condensed ring having 2 to 8 condensed rings, more preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings.
  • the heteroaryl ring may have a substituent or may be unsubstituted. Examples of the substituent include the substituent T described below and a group represented by the formula (R-100) described below.
  • R 1 and R 2 in formula (1) are preferably hydrogen atoms.
  • R3 represents a substituent.
  • a plurality of R3 may be the same or different.
  • the substituent represented by R3 include the substituent T described below and a group represented by formula (R- 100 ) described below.
  • the substituent is preferably an alkyl group, an aryl group, or a heteroaryl group, and more preferably an aryl group.
  • the alkyl group, aryl group, and heteroaryl group include the alkyl group, aryl group, and heteroaryl group described in the sections for R1 and R2 .
  • R 3 in formula (1) is preferably an aryl group.
  • the aryl group represented by R 3 may have a substituent.
  • the substituent include the substituent T described below and a group represented by formula (R-100) described below, and the substituent is preferably a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or an amino group, and more preferably a halogen atom, an alkyl group, or an alkoxy group.
  • the aryl group represented by R 3 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a ring.
  • R 3 in formula (1) is preferably a group represented by formula (R-1).
  • R 31 to R 35 each independently represent a hydrogen atom or a substituent, and adjacent two of R 31 to R 35 may be bonded to form a ring.
  • the substituents represented by R 31 to R 35 are preferably a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group or an amino group, and more preferably a halogen atom, an alkyl group or an alkoxy group.
  • R 31 to R 35 are a substituent, and the remainder are a hydrogen atom.
  • the ring formed is preferably a 5-membered or 6-membered ring.
  • the ring formed may have a substituent. Examples of the substituent include the substituent T described later and a group represented by formula (R-100) described later.
  • L 1 represents an m-valent linking group.
  • the m-valent linking group represented by L 1 include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NR L1 -, -N ⁇ , -NR L1 CO-, -CONR L1 -, -NR L1 SO 2 -, -SO 2 NR L1 -, and groups combining two or more of these groups.
  • R L1 represents a hydrogen atom, an alkyl group, or an aryl group.
  • the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be linear, branched, or cyclic.
  • the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and particularly preferably 1 to 5.
  • the aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 carbon atoms.
  • the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensed rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
  • the heteroatoms constituting the ring of the heterocyclic group are preferably nitrogen atoms, oxygen atoms, or sulfur atoms.
  • the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and more preferably 3 to 12.
  • the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent, such as an alkyl group or an aryl group.
  • the m-valent linking group represented by L 1 in formula (1) is preferably a group containing a benzene ring, and more preferably a group containing 1 to 4 benzene rings.
  • L 1 in formula (1) include groups represented by formulas (L-1) to (L-20), and are preferably groups represented by formulas (L-2), (L-7), (L-11), (L-13), (L-14) or (L-15) because they can further suppress the generation of development residues.
  • formula (L-7) it is preferable that p1 and p2 are each independently 1 or 2.
  • the molecular weight of L 1 is preferably 500 or less, more preferably 400 or less, and even more preferably 300 or less.
  • R L11 , R L12 , R L13 , R L16 to R L23 , R L26 , R L27 , and R L30 to R L50 each independently represent a substituent.
  • R L14 , R L15 , R L24 , R L25 , R L28 and R L29 each independently represent a hydrogen atom or a substituent;
  • R L14 and R L15 may be bonded to form a ring;
  • R L24 and R L25 may be bonded to form a ring;
  • R L28 and R L29 may be bonded to form a ring;
  • p1 to p4 each independently represent an integer of 0 to 4;
  • p11 represents an integer of 0 to 6;
  • p21 represents an integer of 0 to 8;
  • p31 represents an integer of 0 to 8;
  • p41 and p42 each independently represent an integer of 0 to 3;
  • r1 represents 2;
  • Each of r11 to r14
  • R L11 to R L50 are preferably an alkyl group, an aryl group or an alkoxy group, and more preferably an alkyl group.
  • m represents an integer of 2 to 6, preferably an integer of 2 to 4, and more preferably 2 or 3.
  • substituent T examples include the following groups: a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (preferably an alkyl group having 1 to 30 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 30 carbon atoms), an 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 heteroaryl group (preferably a heteroaryl group having 1 to 30 carbon atoms), an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms), a heteroaryloxy group (preferably a heteroaryloxy group (preferably a heteroaryloxy group (preferably
  • a aryl group preferably an aryloxycarbonyl group having 7 to 30 carbon atoms
  • a heteroaryloxycarbonyl group preferably a heteroaryloxycarbonyl group having 2 to 30 carbon atoms
  • an acyloxy group preferably an acyloxy group having 2 to 30 carbon atoms
  • an acylamino group preferably an acylamino group having 2 to 30 carbon atoms
  • an aminocarbonylamino group preferably an aminocarbonylamino group having 2 to 30 carbon atoms
  • an alkoxycarbonylamino group preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms
  • an aryloxycarbonylamino group preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms
  • a sulfamoyl group preferably a sulfamoyl group having 0 to 30 carbon atoms
  • a sulfamoylamino group preferably
  • L R1 represents a single bond or an (n+1)-valent linking group
  • Y R1 represents an acid group, a basic group, or a phthalimido group
  • n represents an integer of 1 to 4, and n is 1 when L 3 R1 is a single bond.
  • L 1 R1 represents a single bond or an (n+1)-valent linking group.
  • L 1 R1 is preferably an (n+1)-valent linking group.
  • n+1-valent linking group represented by L R1 examples include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NR L100 -, -N ⁇ , -NR L100 CO-, -CONR L100 -, -NR L100 SO 2 -, -SO 2 NR L100 -, and groups consisting of combinations thereof.
  • R L100 represents a hydrogen atom, an alkyl group, or an aryl group.
  • the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be linear, branched, or cyclic.
  • the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and particularly preferably 1 to 5.
  • the aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 carbon atoms.
  • the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensed rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
  • the heteroatoms constituting the ring of the heterocyclic group are preferably nitrogen atoms, oxygen atoms, or sulfur atoms.
  • the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and more preferably 3 to 12.
  • the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent, such as an alkyl group or an aryl group.
  • Y 1 R1 represents an acid group or a basic group.
  • the acid group represented by Y 1 R1 include a carboxy group, a sulfo group, a phosphate group, a boronic acid group, an imidic acid group, and salts thereof.
  • the atom or atomic group constituting the salt include an alkali metal ion (Li + , Na + , K + , etc.), an alkaline earth metal ion (Ca 2+ , Mg 2+ , etc.), an ammonium ion, an imidazolium ion, a pyridinium ion, and a phosphonium ion.
  • R X1 to R X4 each independently represent an alkyl group or an aryl group.
  • the alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
  • the substituent is preferably a halogen atom, more preferably a fluorine atom.
  • R X1 to R X4 each independently represent an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, more preferably an alkyl group containing a fluorine atom.
  • the number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.
  • the number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and still more preferably 6.
  • Examples of the basic group represented by YR1 include an amino group, a pyridinyl group and salts thereof, and an ammonium salt.
  • Examples of the atom or atomic group constituting the salt include a hydroxide ion, a halogen ion, a carboxylate ion, a sulfonate ion, and a phenoxide ion.
  • Examples of the amino group include a group represented by -NRx11Rx12 and a cyclic amino group.
  • R x11 and R x12 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent. Examples of the substituent include the above-mentioned substituent T.
  • the number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group may have a substituent. Examples of the substituent include the above-mentioned substituent T.
  • cyclic amino groups include pyrrolidine groups, piperidine groups, piperazine groups, and morpholine groups. These groups may further have a substituent. Examples of the substituent include the substituent T described above.
  • n represents an integer from 1 to 4, preferably 1 or 2, and more preferably 1.
  • the specific compound may be a pigment or a dye.
  • the specific compound may also be a pigment derivative.
  • the specific compound is a compound having a group represented by formula (R-100) as a substituent.
  • the specific compound is preferably a pigment. Also, the specific compound is preferably a red colorant. It is particularly preferable that the specific compound is a red pigment.
  • Specific examples of specific compounds include compounds (P-1) to (P-43) described in the Examples below.
  • the colorant contained in the coloring composition of the present invention may further contain a colorant other than the specific compound described above (hereinafter, also referred to as other colorant).
  • a colorant other than the specific compound described above hereinafter, also referred to as other colorant.
  • other colorants include green colorants, red colorants, yellow colorants, purple colorants, blue colorants, orange colorants, etc.
  • pigment derivatives may also be used as the other colorants.
  • the other colorant preferably includes at least one selected from a green colorant, a red colorant, a yellow colorant, and an orange colorant, more preferably includes at least one selected from a red colorant, a yellow colorant, and an orange colorant, even more preferably includes at least one selected from a red colorant and a yellow colorant, and particularly preferably includes a yellow colorant. It is also preferable that the other colorants include at least one selected from a red colorant and an orange colorant, and a yellow colorant.
  • the content of the yellow colorant is preferably 5 to 200 parts by mass per 100 parts by mass of the specific compound described above.
  • the lower limit is preferably 10 parts by mass or more, and more preferably 15 parts by mass or more.
  • the upper limit is preferably 170 parts by mass or less, and more preferably 140 parts by mass or less.
  • the content of the red colorant is preferably 10 to 900 parts by mass per 100 parts by mass of the specific compound described above.
  • the lower limit is preferably 30 parts by mass or more, and more preferably 50 parts by mass or more.
  • the upper limit is preferably 700 parts by mass or less, and more preferably 500 parts by mass or less.
  • the content of the orange colorant is preferably 10 to 900 parts by mass per 100 parts by mass of the specific compound described above.
  • the lower limit is preferably 30 parts by mass or more, and more preferably 50 parts by mass or more.
  • the upper limit is preferably 700 parts by mass or less, and more preferably 500 parts by mass or less.
  • the other colorant preferably includes at least one colorant A selected from C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 272, C.I. Pigment Red 291, C.I. Pigment Orange 71, C.I. Pigment Orange 73, and C.I. Pigment Orange 81.
  • the colorant A is preferably at least one selected from C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 272, C.I. Pigment Orange 71, and C.I. Pigment Orange 73.
  • the content of the above-mentioned colorant A is preferably 10 to 900 parts by mass per 100 parts by mass of the above-mentioned specific compound.
  • the lower limit is preferably 30 parts by mass or more, and more preferably 50 parts by mass or more.
  • the upper limit is preferably 700 parts by mass or less, and more preferably 500 parts by mass or less.
  • Red colorants include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, with diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds being preferred, and diketopyrrolopyrrole compounds being more preferred.
  • the red colorant is preferably a red pigment.
  • red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149,
  • red pigments include 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, and 297.
  • red colorant a compound described in paragraph 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.
  • the red colorant is preferably at least one selected from C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 272, and C.I. Pigment Red 291, and more preferably at least one selected from C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, and C.I. Pigment Red 272, because this can suppress the generation of development residues.
  • Green colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred because they are more likely to form a film with excellent heat diffusion resistance. Also, the green colorant is preferably a green pigment.
  • green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66.
  • halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used as green colorants.
  • Specific examples include the compounds described in WO 2015/118720.
  • compounds described in paragraph 0029 of WO 2022/085485, aluminum phthalocyanine compounds described in JP 2020-070426 A, and diarylmethane compounds described in JP 2020-504758 A can also be used as green colorants.
  • Preferred green colorants are C.I. Pigment Green 7, 36, 58, 62, and 63.
  • Orange colorants include diketopyrrolopyrrole compounds and azo compounds, and are preferably diketopyrrolopyrrole compounds.
  • the orange colorant is preferably an orange pigment.
  • Specific examples of orange colorants include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, and 81.
  • the orange colorant is preferably at least one selected from C.I. Pigment Orange 71, C.I. Pigment Orange 73, and C.I. Pigment Orange 81.
  • Yellow colorants include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds.
  • the yellow colorant is preferably a yellow pigment. Specific examples of yellow colorants include C.I.
  • an azobarbituric acid nickel complex having the following structure can also be used.
  • the compounds described in paragraphs 0031 to 0033 of WO 2022/085485, the methine dyes described in JP 2019-073695 A, and the methine dyes described in JP 2019-073696 A can be used.
  • Purple colorants include dioxazine compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, and are preferably dioxazine compounds.
  • the purple colorant is preferably a purple pigment.
  • Specific examples of purple colorants include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
  • the blue colorant may be a phthalocyanine compound or a squarylium compound, and is preferably a phthalocyanine compound.
  • the blue colorant is preferably a blue pigment.
  • Specific examples of the blue colorant include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88.
  • Aluminum phthalocyanine compounds having phosphorus atoms may also be used as blue colorants. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
  • Dyes can also be used as other colorants.
  • any known dyes can be used. Examples include pyrazole azo dyes, anilino azo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, phenothiazine dyes, pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyrromethene dyes.
  • a dye polymer can also be used as the other colorant.
  • the dye polymer is preferably a dye dissolved in a solvent before use.
  • the dye polymer may form particles. When the dye polymer is in the form of particles, it is usually used in a state of being dispersed in a solvent.
  • the dye polymer in a particle state can be obtained, for example, by emulsion polymerization, and examples of the compound and manufacturing method described in JP-A-2015-214682 include the compound and manufacturing method described therein.
  • the dye polymer has two or more dye structures in one molecule, and preferably has three or more dye structures. There is no particular limit to the upper limit, but it can be 100 or less.
  • the multiple dye structures in one molecule may be the same dye structure or different dye structures.
  • the weight average molecular weight (Mw) of the dye polymer is preferably 2,000 to 50,000.
  • the lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more.
  • the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
  • the dye multimer may be a compound described in JP2011-213925A, JP2013-041097A, JP2015-028144A, JP2015-030742A, WO2016/031442, etc.
  • colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP 2020-117638 A, phthalocyanine compounds described in WO 2020/174991, isoindoline compounds or salts thereof described in JP 2020-160279 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730, and compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070.
  • 10-2020-0069062 halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP-A-2020-180176, phenothiazine compounds described in JP-A-2021-187913, halogenated zinc phthalocyanines described in WO 2022/004261, and halogenated zinc phthalocyanines described in WO 2021/250883 can be used.
  • the other 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-shaped structure, or may be used in both structures.
  • Other colorants include quinophthalone compounds represented by formula 1 in Korean Patent Publication No.
  • 10-2020-0030759 polymer dyes described in Korean Patent Publication No. 10-2020-0061793, colorants described in JP-A-2022-029701, isoindoline compounds described in WO 2022/014635, aluminum phthalocyanine compounds described in WO 2022/024926, compounds described in JP-A-2022-045895, compounds described in WO 2022/050051, compounds described in JP-A-2020-090676, compounds described in JP-A-2020-055956, compounds described in JP-A-2021-031681, compounds described in JP-A-2022-056354, and compounds described in U.S. Patent Application Publication No.
  • the colorant contained in the coloring composition may contain two or more chromatic colorants, and may form a black color by combining two or more chromatic colorants.
  • a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter.
  • Examples of the combination of chromatic colorants when forming a black color by combining two or more chromatic colorants include the following. (1) An embodiment containing a red colorant, a blue colorant, and a yellow colorant. (2) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant. (3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant. (4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. (5) An embodiment containing a yellow colorant and a purple colorant.
  • colorants include compounds having a dye structure and at least one group selected from an acid group, a basic group, and a phthalimide group. Such compounds are used as pigment derivatives.
  • the above dye structures include a quinoline dye structure, a benzimidazolone dye structure, a benzisoindole dye structure, a benzothiazole dye structure, an iminium dye structure, a squarylium dye structure, a croconium dye structure, an oxonol dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, an azo dye structure, an azomethine dye structure, a phthalocyanine dye structure, a naphthalocyanine dye structure, an anthraquinone dye structure, a quinacridone dye structure, a dioxazine dye structure, a perinone dye structure, a perylene dye structure, a thiazineindigo dye structure, a thioindigo dye structure, an isoindoline dye structure, an isoindolinone dye structure, a quinophthalone dye structure, a dithiol dye structure
  • Examples of the acid group possessed by the pigment derivative include a carboxy group, a sulfo group, a phosphate group, a boronic acid group, an imide acid group, and salts thereof.
  • Examples of the atom or atomic group constituting the salt include an alkali metal ion (Li + , Na + , K + , etc.), an alkaline earth metal ion (Ca 2+ , Mg 2+ , etc.), an ammonium ion, an imidazolium ion, a pyridinium ion, and a phosphonium ion.
  • Examples of the imide acid group include -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 , and -SO 2 NHCOR X4 , and -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , and -SO 2 NHCOR X4 are more preferable, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 are even more preferable.
  • R X1 to R X4 each independently represent an alkyl group or an aryl group.
  • the alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
  • the substituent is preferably a halogen atom, more preferably a fluorine atom.
  • R X1 to R X4 each independently represent an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, more preferably an alkyl group containing a fluorine atom.
  • the number of carbon atoms of the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the number of carbon atoms of the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.
  • Basic groups contained in pigment derivatives include amino groups, pyridinyl groups and their salts, and salts of ammonium groups.
  • Atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
  • amino group examples include a group represented by --NR.sub.x11R.sub.x12 and a cyclic amino group.
  • R x11 and R x12 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent. Examples of the substituent include the above-mentioned substituent T.
  • the number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group may have a substituent. Examples of the substituent include the above-mentioned substituent T.
  • Cyclic amino groups include pyrrolidine groups, piperidine groups, piperazine groups, and morpholine groups. These groups may further have a substituent.
  • the pigment derivative may be a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative).
  • the maximum molar absorption coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L ⁇ mol -1 ⁇ cm -1 or less, more preferably 1000 L ⁇ mol -1 ⁇ cm -1 or less, and even more preferably 100 L ⁇ mol-1 ⁇ cm -1 or less.
  • 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 the compounds described in the Examples below, the compounds described in paragraph 0124 of WO 2022/085485, the benzimidazolone compounds or salts thereof described in JP 2018-168244 A, and the compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282.
  • the content of the colorant in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more.
  • the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less.
  • the content of the pigment in the colorant is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, and even more preferably 70 to 100% by mass.
  • the total content of the pigment and pigment derivative in the colorant is preferably 25 to 100% by mass, more preferably 55 to 100% by mass, and even more preferably 75 to 100% by mass.
  • the content of the specific compound in the colorant is preferably 7% by mass or more, more preferably 9% by mass or more, and even more preferably 11% by mass or more.
  • the upper limit can be 100% by mass, or can be 95% by mass or less, or can be 90% by mass or less.
  • the colorant contained in the coloring composition of the present invention preferably contains a specific compound and a pigment derivative.
  • the pigment derivative preferably contains a compound having a dye structure and at least one group selected from an acid group, a basic group, and a phthalimide group, and more preferably contains a compound having a diketopyrrolopyrrole dye structure and at least one group selected from an acid group, a basic group, and a phthalimide group.
  • the content of the pigment derivative is preferably 1 to 30 parts by mass relative to 100 parts by mass of the specific compound.
  • the lower limit is preferably 3 parts by mass or more.
  • the upper limit is preferably 20 parts by mass or less.
  • the content of the compound having a diketopyrrolopyrrole dye structure and at least one group selected from an acid group, a basic group, and a phthalimide group is preferably 1 to 30 parts by mass relative to 100 parts by mass of the specific compound.
  • the lower limit is preferably 3 parts by mass or more.
  • the upper limit is preferably 20 parts by mass or less.
  • the pigment derivatives may be used alone or in combination of two or more kinds.
  • the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, it is preferable to use a colorant containing a yellow colorant and a red colorant.
  • the red colorant contains a specific compound.
  • the content of the specific compound in the red colorant is preferably 15% by mass or more, more preferably 20% by mass or more.
  • the upper limit can be 100% by mass or less, or 95% by mass or less.
  • the coloring composition of the present invention contains a resin.
  • the resin is blended, for example, for dispersing pigments in the coloring composition or for use as a binder.
  • a resin used mainly for dispersing pigments in the coloring composition is also called a dispersant.
  • such uses of the resin are merely examples, and the resin can also be used for purposes other than such uses.
  • the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
  • the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
  • the lower limit is preferably 4,000 or more, and more preferably 5,000 or more.
  • resins examples include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and siloxane resins.
  • the resin there are resins described in paragraphs 0091 to 0099 of WO 2022/065215, block polyisocyanate resins described in JP 2016-222891 A, resins described in JP 2020-122052 A, resins described in JP 2020-111656 A, resins described in JP 2020-139021 A, and structural units having a ring structure in the main chain and side chains described in JP 2017-138503 A and a structural unit having a biphenyl group, the resin described in paragraphs 0199 to 0233 of JP 2020-186373 A, the alkali-soluble resin described in JP 2020-186325 A, the resin represented by formula 1 described in Korean Patent Publication No. 10-2020-0078339 A, the copolymer containing an epoxy group and an acid group described in WO 2022/030445 A, and the compound described in JP 2018-135514 A can also be used.
  • the resin it is preferable to use a resin having an acid group.
  • the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group.
  • the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
  • the lower limit is more preferably 40 mgKOH/g or more, and particularly preferably 50 mgKOH/g or more.
  • the upper limit is more preferably 400 mgKOH/g or less, even more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
  • the weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, and more preferably 5,000 to 50,000.
  • the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
  • the resin having an acid group preferably contains a repeating unit having an acid group on the side chain, and more preferably contains 5 to 70 mol% of the repeating units having an acid group on the side chain out of all the repeating units of the resin.
  • the upper limit of the content of repeating units having an acid group on the side chain is preferably 50 mol% or less, and more preferably 30 mol% or less.
  • the lower limit of the content of repeating units having an acid group on the side chain is preferably 10 mol% or more, and more preferably 20 mol% or more.
  • the coloring composition of the present invention also preferably contains a resin having a basic group.
  • the resin having a basic group is preferably a resin containing a repeating unit having a basic group in the side chain, more preferably a copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group, and even more preferably a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group.
  • the resin having a basic group can also be used as a dispersant.
  • the amine value of the resin having a basic group is preferably 5 to 300 mgKOH/g.
  • the lower limit is preferably 10 mgKOH/g or more, and more preferably 20 mgKOH/g or more.
  • the upper limit is preferably 200 mgKOH/g or less, and more preferably 100 mgKOH/g or less.
  • resins with basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (all manufactured by BYK-Chemie), Solsperse 11200, 13240, 13650, 13940, 24 000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
  • the resin having a basic group may be a block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A, a block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.
  • the coloring composition of the present invention contains both a resin having an acid group and a resin having a basic group. According to this embodiment, the storage stability of the coloring composition can be further improved.
  • the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and even more preferably 50 to 200 parts by mass, per 100 parts by mass of the resin having an acid group.
  • a resin having an aromatic carboxy group As the resin, it is also preferable to use a resin having an aromatic carboxy group.
  • the aromatic carboxy group may be included in the main chain of a repeating unit, or may be included in a side chain of the repeating unit. It is preferable that the aromatic carboxy group is included in the main chain of a repeating unit.
  • an aromatic carboxy group refers to 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 an aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
  • resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021/166858.
  • the resin it is also preferable to use a graft resin.
  • the graft resin can be used as a dispersant, but it may also be used as a binder.
  • the graft resin is a resin having a graft chain.
  • the graft chain means a polymer chain that branches off and extends from the main chain of the repeating unit.
  • the graft chain preferably has 40 to 10,000 atoms excluding hydrogen atoms, more preferably 50 to 2,000 atoms excluding hydrogen atoms, and even more preferably 60 to 500 atoms excluding hydrogen atoms.
  • the graft chain preferably contains repeating units of at least one structure selected from a polyether structure, a polyester structure, a poly(meth)acrylic structure, a polystyrene structure, a polyurethane structure, a polyurea structure, and a polyamide structure, more preferably contains repeating units of at least one structure selected from a polyether structure, a polyester structure, a poly(meth)acrylic structure, and a polystyrene structure, further preferably contains repeating units of a polyether structure or a polyester structure, and particularly preferably contains repeating units of a polyester structure because of its excellent pigment dispersibility.
  • Examples of the repeating unit of the polyester structure include a repeating unit of the structure represented by formula (G-1), formula (G-4) or formula (G-5).
  • Examples of the repeating unit of the polyether structure include a repeating unit of the structure represented by formula (G-2).
  • Examples of the repeating unit of the poly(meth)acrylic structure include a repeating unit of the structure represented by formula (G-3).
  • Examples of the repeating unit of the polystyrene structure include a repeating unit of the structure represented by formula (G-6).
  • R G1 and R G2 each independently represent an alkylene group.
  • the alkylene group represented by R G1 and R G2 is not particularly limited, but is preferably a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a linear or branched alkylene group having 2 to 16 carbon atoms, and even more preferably a linear or branched alkylene group having 3 to 12 carbon atoms.
  • R G3 represents a hydrogen atom or a methyl group
  • Q G1 represents --O-- or --NH--
  • L G1 represents a single bond or a divalent linking group
  • R G4 represents a hydrogen atom or a substituent.
  • Examples of the divalent linking group represented by L G1 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylenecarbonyl group (preferably an oxyalkylenecarbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO-, OCO-, -S-, and groups combining two or more of these.
  • an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
  • an alkyleneoxy group preferably an alkyleneoxy group having 1 to 12 carbon atoms
  • an oxyalkylenecarbonyl group preferably an oxyalkylenecarbonyl group having 1 to 12 carbon atoms
  • an arylene group preferably an arylene group having
  • Examples of the substituent represented by R G4 include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, an ethylenically unsaturated bond-containing group, an epoxy group, an oxetanyl group, and a blocked isocyanate group.
  • R G5 represents a hydrogen atom or a methyl group
  • R G6 represents an aryl group.
  • the number of carbon atoms of the aryl group represented by R G6 is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12.
  • the aryl group represented by R G6 may have a substituent.
  • substituents examples include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, an ethylenically unsaturated bond-containing group, an epoxy group, an oxetanyl group, and a blocked isocyanate group.
  • the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
  • the substituent may be a group represented by formula (W-1). -L w1 -R w1 ...(W-1)
  • L w1 represents a single bond or a divalent linking group.
  • R w1 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, or a heteroarylthioether group.
  • Examples of the divalent linking group represented by L w1 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO-, OCO-, -S-, and a group combining two or more of these.
  • the graft chain is preferably a structure represented by the following formula (G-1a), (G-2a), (G-3a), (G-4a), (G-5a) or (G-6a), and more preferably a structure represented by formula (G-1a), (G-4a) or (G-5a).
  • R G1 and R G2 each represent an alkylene group
  • R G3 represents a hydrogen atom or a methyl group
  • Q G1 represents -O- or -NH-
  • L G1 represents a single bond or a divalent linking group
  • R G4 represents a hydrogen atom or a substituent
  • R G5 represents a hydrogen atom or a methyl group
  • R G6 represents an aryl group
  • W 100 represents a hydrogen atom or a substituent
  • n1 to n6 each independently represent an integer of 2 or more.
  • R G1 to R G6 , Q G1 , and L G1 are synonymous with R G1 to R G6 , Q G1 , and L G1 described in formulas (G-1) to (G-6), and the preferred ranges are also the same.
  • W 100 is preferably a substituent.
  • substituents include the group represented by formula (W-1) above.
  • n1 to n6 are each preferably an integer from 2 to 100, more preferably an integer from 2 to 80, and even more preferably an integer from 8 to 60.
  • R G1 in each repeating unit may be the same or different.
  • R G1 contains two or more different repeating units, the arrangement of each repeating unit is not particularly limited and may be random, alternating, or block. The same applies to formulas (G-2a) to (G-6a).
  • the graft chain has a structure represented by formula (G-1a), formula (G-4a), or formula (G-5a) and contains two or more different repeating units in R G1 .
  • the graft resin is preferably a resin having a repeating unit having a graft chain.
  • An example of the repeating unit having a graft chain is a repeating unit represented by formula (A-1-2).
  • X2 represents a divalent linking group
  • L2 represents a single bond or a divalent linking group
  • W1 represents a graft chain.
  • Examples of the trivalent linking group represented by X2 include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, a polyamide linking group, a polyether linking group, and a polystyrene linking group.
  • a poly(meth)acrylic linking group or a polyalkyleneimine linking group is preferable, and a poly(meth)acrylic linking group is more preferable.
  • Examples of the divalent linking group represented by L2 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO-, OCO-, -S-, and groups combining two or more of these.
  • the graft chain represented by W 1 includes the graft chains described above.
  • repeating unit represented by formula (A-1-2) include a repeating unit represented by the following formula (A-1-2a) and a repeating unit represented by the following formula (A-1-2b).
  • R b1 to R b3 each independently represent a hydrogen atom or an alkyl group
  • Q b1 represents -CO-, -COO-, -OCO-, -CONH- or a phenylene group
  • L 2 represents a single bond or a divalent linking group
  • W 1 represents a graft chain.
  • the number of carbon atoms in the alkyl group represented by R b1 to R b3 is preferably 1 to 10, more preferably 1 to 3, and even more preferably 1.
  • Q b1 is preferably -COO- or -CONH-, and more preferably -COO-.
  • R b10 and R b11 each independently represent a hydrogen atom or an alkyl group
  • m2 represents an integer of 1 to 5
  • L 2 represents a single bond or a divalent linking group
  • W 1 represents a graft chain.
  • the number of carbon atoms in the alkyl group represented by R b10 and R b11 is preferably 1 to 10, and more preferably 1 to 3.
  • the weight average molecular weight of the repeating unit having a graft chain is preferably 1000 or more, more preferably 1000 to 10000, and even more preferably 1000 to 7500.
  • the weight average molecular weight of the repeating unit having a graft chain is a value calculated from the weight average molecular weight of the raw material monomer used in the polymerization of the repeating unit.
  • a repeating unit having a graft chain can be formed by polymerizing a macromonomer.
  • a macromonomer means a polymeric compound in which a polymerizable group is introduced at the polymer end.
  • the content of repeating units having graft chains is preferably 1 mol% or more, more preferably 2 mol% or more, and even more preferably 3 mol% or more, of all repeating units of the graft resin.
  • the upper limit can be 90 mol% or less, 80 mol% or less, or 70 mol% or less.
  • the graft resin may further have a repeating unit having an acid group.
  • the acid group include a carboxy group, a sulfo group, and a phosphate group, and from the viewpoint of pigment dispersibility, a carboxy group is preferred.
  • the content of repeating units having an acid group is preferably 1 mol% or more, more preferably 2 mol% or more, and even more preferably 3 mol% or more, of all repeating units of the graft resin.
  • the upper limit can be 90 mol% or less, 80 mol% or less, or 70 mol% or less.
  • the graft resin may further have a repeating unit having an ethylenically unsaturated bond-containing group.
  • the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group.
  • the content of repeating units having an ethylenically unsaturated bond-containing group is preferably 1 mol% or more, more preferably 2 mol% or more, and even more preferably 3 mol% or more, of all repeating units of the graft resin.
  • the upper limit can be 90 mol% or less, 80 mol% or less, or 70 mol% or less.
  • the weight average molecular weight of the graft resin is preferably 3,000 to 100,000.
  • the upper limit is preferably 80,000 or less, and more preferably 60,000 or less.
  • the lower limit is preferably 5,000 or more, and more preferably 8,000 or more.
  • 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) refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
  • the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol% or more when the total amount of the acid groups and the basic groups 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 to 105 mgKOH/g.
  • the basic dispersant refers to a resin in which the amount of basic groups is greater than the amount of acid groups.
  • the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups is greater than the amount of acid groups when the total amount of the acid groups and the 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 a graft resin.
  • the graft resin include those mentioned above.
  • the resin used as the dispersant is a resin having an aromatic carboxy group.
  • resins having an aromatic carboxy group include those mentioned above.
  • the resin used as the dispersant is preferably a polyimine-based dispersant containing nitrogen atoms in at least one of the main chain and side chain.
  • the polyimine-based dispersant is preferably a resin having a main chain with a partial structure having a functional group with a pKa of 14 or less, a side chain with 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and side chain.
  • the basic nitrogen atom so long as it is a nitrogen atom that exhibits basicity.
  • polyimine-based dispersants please refer to the description in paragraphs 0102 to 0166 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
  • the resin used as the dispersant is preferably one having a structure in which multiple polymer chains are bonded to a core portion.
  • resins include dendrimers (including star-shaped polymers).
  • dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962A.
  • the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain.
  • the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol % or more of the total repeating units of the resin, more preferably 10 to 80 mol %, and even more preferably 20 to 70 mol %.
  • resins described in JP 2018-087939 A, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6,432,077 A, polyethyleneimine having a polyester side chain described in WO 2016/104803 A, block copolymers described in WO 2019/125940 A, block polymers having an acrylamide structural unit described in JP 2020-066687 A, block polymers having an acrylamide structural unit described in JP 2020-066688 A, dispersants described in WO 2016/104803 A, and the like can also be used.
  • Dispersants are also available as commercially available products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Nippon, the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Ltd.
  • the products described in paragraph 0129 of JP 2012-137564 A and the products described in paragraph 0235 of JP 2017-194662 A can also be used as dispersants.
  • the content of the resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
  • the content of the resin having an acid group in the total solid content of the coloring composition is preferably 1 to 60% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
  • the content of the graft resin in the total solid content of the coloring composition is preferably 12 to 60% by mass.
  • the lower limit is preferably 15% by mass or more, and more preferably 18% by mass or more.
  • the upper limit is preferably 50% by mass or less, and more preferably 40% by mass or less.
  • the content of the dispersant is preferably 10 to 100 parts by mass relative to 100 parts by mass of the pigment.
  • the lower limit is preferably 15 parts by mass or more, and more preferably 20 parts by mass or more.
  • the upper limit is preferably 80 parts by mass or less, and more preferably 60 parts by mass or less.
  • the coloring composition of the present invention may contain only one type of resin, or may contain two or more types of resins. When two or more types of resins are contained, the total amount thereof is preferably within the above range.
  • the coloring composition of the present invention contains a solvent.
  • the solvent include organic solvents.
  • the type of solvent is not particularly limited as long as the solubility of each component and the coatability of the composition are satisfied.
  • the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents.
  • ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group 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, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol dimethyl ether, butyl acetate ...
  • Examples of the ethylene glycol monomethyl ether acetate include 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol.
  • diacetone alcohol also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone
  • 2-methoxypropyl acetate 2-methoxy-1-propanol,
  • the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons, etc. (for example, the amount can be 50 ppm (parts per million) by mass or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).
  • 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 parts per billion (ppb) by mass or less. If necessary, an organic solvent with a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).
  • Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter.
  • the filter used for filtration preferably has a pore size of 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
  • the filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.
  • the organic solvent may contain isomers (compounds with the same number of atoms but different structures).
  • the organic solvent may contain only one type of isomer, or multiple types of isomers.
  • the peroxide content in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
  • the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
  • the coloring composition of the present invention is substantially free of environmentally regulated substances.
  • substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the coloring composition is 50 ppm by mass or less, preferably 30 ppm by mass or less, more preferably 10 ppm by mass or less, and particularly preferably 1 ppm by mass or less.
  • environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
  • distillation methods can be performed at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or the stage of a colored composition prepared by mixing these compounds.
  • the coloring composition of the present invention preferably contains a polymerizable compound.
  • the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
  • the ethylenically unsaturated bond-containing group include vinyl A group, a (meth)allyl group, a (meth)acryloyl group, etc.
  • the polymerizable compound used in the present invention is preferably a radical polymerizable compound.
  • the polymerizable compound may be in any chemical form, such as a monomer, prepolymer, or oligomer, but is preferably a monomer.
  • the molecular weight of the polymerizable compound is preferably 100 to 3,000.
  • the upper limit is more preferably 2,000 or less, and even more preferably 1,500 or less.
  • the lower limit is more preferably 150 or more, and even more preferably 250 or more.
  • the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups.
  • the polymerizable compound is preferably a 3-15 functional (meth)acrylate compound, and more preferably a 3-6 functional (meth)acrylate compound.
  • Specific examples of the polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022/065215.
  • Preferred polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product is KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product is KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product is KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products are KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl groups are bonded via ethylene glycol and/or propylene glycol residues (e.g.,
  • Examples of the polymerizable compound include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
  • diglycerol EO ethylene oxide
  • methacrylate commercially available product is M-460; manufactured by Toagosei Co., Ltd.
  • NK Ester A-TMMT pentaerythritol tetraacrylate
  • KAYARAD HDDA 1,6-hexanedio
  • NK Oligo UA-7200 (Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.), etc. can also be used.
  • the content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 35% by mass.
  • the upper limit is preferably 30% by mass or less, and more preferably 25% by mass or less.
  • the lower limit is preferably 2% by mass or more, and more preferably 5% by mass or more.
  • the coloring composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, it is preferable that the total amount thereof is within the above range.
  • the coloring composition of the present invention may contain a photopolymerization initiator.
  • the coloring composition of the present invention contains a polymerizable compound, it is preferable that the coloring composition of the present invention further contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet range to the visible range is preferable.
  • 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, etc.
  • 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, etc.
  • the photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl substituted coumarin compound, more preferably a compound selected from an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
  • examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A, the compounds described in Japanese Patent No. 6301489 A, and the compounds described in MATERIAL STAGE 37 to 60p, vol. 19, No.
  • hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (all manufactured by BASF), etc.
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc.
  • Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc.
  • Examples of oxime compounds include the compound described in paragraph 0142 of WO 2022/085485, the compound described in Japanese Patent No. 5,430,746, the compound described in Japanese Patent No. 5,647,738, the compound represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of JP 2021-173858 A, the compound represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of JP 2021-170089 A, and the like.
  • oxime compound examples include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-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 an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring, an oxime compound having a fluorine atom, an oxime compound having a nitro group, an oxime compound having a benzofuran skeleton, an oxime compound in which a substituent having a hydroxyl group is bonded to a carbazole skeleton, or a compound described in paragraphs 0143 to 0149 of WO 2022/085485 can also be used.
  • oxime compounds that are 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 absorption coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably 1000 to 300,000, even more preferably 2000 to 300,000, and particularly preferably 5000 to 200,000.
  • the molar absorption coefficient of the compound can be measured using a known method. For example, it is preferable to measure using a spectrophotometer (Varian Cary-5 spectrophotometer) at a concentration of 0.01 g/L using ethyl acetate as a solvent.
  • a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
  • a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so good sensitivity can be obtained.
  • crystallinity is reduced and solubility in solvents is improved, making it less likely to precipitate over time, and the stability over time of the coloring composition can be improved.
  • Specific examples of bifunctional or trifunctional or higher functional photoradical polymerization initiators include the compounds described in paragraph 0148 of WO 2022/065215.
  • the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 30% by mass.
  • the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
  • the upper limit is preferably 20% by mass or less, and more preferably 15% by mass or less.
  • only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the coloring composition of the present invention may further contain an infrared absorbing agent.
  • an infrared transmission filter is formed using the coloring composition of the present invention, the wavelength of light transmitted through the film obtained by adding an infrared absorbing agent to the coloring composition can be shifted to a longer wavelength side.
  • the infrared absorbing agent is preferably a compound having a maximum absorption wavelength on the longer wavelength side than a wavelength of 700 nm.
  • the infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and not more than 1800 nm.
  • the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm of the infrared absorbing agent and the absorbance A 2 at the maximum absorption wavelength is preferably 0.08 or less, more preferably 0.04 or less.
  • Infrared absorbents 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, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like. Specific examples of these include the compounds described in paragraphs 0114 to 0121 of WO 2022/065215.
  • the compounds described in paragraph 0121 of WO 2022/065215, squarylium compounds described in JP 2020-075959 A, and copper complexes described in Korean Patent Publication No. 10-2019-0135217 can also be used.
  • the croconate compound described in JP 2021-195515 A, the infrared absorber described in JP 2022-022070 A, and the croconium compound described in WO 2019/021767 A can also be used.
  • tungsten oxide represented by the following formula described in paragraph 0025 of European Patent No. 3628645 can also be used.
  • M 1 and M 2 each represent an ammonium cation or a metal cation, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, d is 2.5 to 3, e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent.
  • 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 preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more.
  • the upper limit is preferably 30% by mass or less, and 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. When two or more types of infrared absorbing agents are contained, it is preferable that the total amount thereof is within the above range.
  • the coloring composition of the present invention may contain a compound having a cyclic ether group.
  • the cyclic ether group include an epoxy group and an oxetanyl group.
  • the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
  • the epoxy compound include compounds having one or more epoxy groups in one molecule, and compounds having two or more epoxy groups are preferred.
  • the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
  • the upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less.
  • the lower limit of the epoxy groups contained in the epoxy compound is preferably 2 or more.
  • Examples of compounds having a cyclic ether group include those described in paragraphs 0034 to 0036 of JP-A-2013-011869, 0147 to 0156 of JP-A-2014-043556, and 0085 to 0092 of JP-A-2014-089408.
  • Compounds described in JP-A-2017-179172, xanthene-type epoxy resins described in JP-A-2021-195421, and xanthene-type epoxy resins described in JP-A-2021-195422 can also be used.
  • the compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, or in the case of a polymer, a weight average molecular weight of 1000 or more).
  • the weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000.
  • the upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and even more preferably 3,000 or less.
  • EHPE3150 manufactured by Daicel Corporation
  • EPICLON N-695 manufactured by DIC Corporation
  • Marproof G-0150M G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
  • the content of the compound having a cyclic ether group 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, and more preferably 1% by mass or more.
  • the upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. Only one type of compound having a cyclic ether group may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the coloring composition of the present invention may also contain a polyalkyleneimine.
  • the polyalkyleneimine is used, for example, as a dispersing aid for pigments.
  • the dispersing aid is a material for enhancing the dispersibility of pigments in a coloring composition.
  • the polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine.
  • the polyalkyleneimine is a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group.
  • the number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2.
  • 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 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 number average molecular weight value measured by the boiling point elevation method is used.
  • the number average molecular weight value measured by the viscosity method is used.
  • the number average molecular weight value measured in polystyrene equivalent value by 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.
  • alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred.
  • the polyalkyleneimine is particularly preferably polyethyleneimine.
  • the polyethyleneimine preferably contains primary amino groups in an amount of 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more, based on the total of the primary amino groups, secondary amino groups, and tertiary amino groups.
  • Commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all 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 mass%.
  • the lower limit is preferably 0.2 mass% or more, more preferably 0.5 mass% or more, and even more preferably 1 mass% or more.
  • the upper limit is preferably 4.5 mass% or less, more preferably 4 mass% or less, and even more preferably 3 mass% or less.
  • the content of polyalkyleneimine is preferably 0.5 to 20 mass parts per 100 mass parts of pigment.
  • the lower limit is preferably 0.6 mass% or more, more preferably 1 mass% or more, and even more preferably 2 mass% or more.
  • the upper limit is preferably 10 mass% or less, and even more preferably 8 mass% or less. Only one type of polyalkyleneimine 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 may contain a curing accelerator.
  • the curing accelerator include a thiol compound, a methylol compound, an amine compound, a phosphonium salt compound, an amidine salt compound, an amide compound, a base generator, an isocyanate compound, an alkoxysilane compound, and an onium salt compound.
  • Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485 and the compound described in JP-A-2021-181406.
  • 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 may contain an ultraviolet absorber.
  • ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. Specific examples of such compounds include the compounds described in paragraph 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A-2021-178918, the ultraviolet absorbers described in JP-A-2022-007884, and the compounds described in Korean Patent Publication No. 10-2022-0014454.
  • 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 types are used, it is preferable that the total amount is within the above range.
  • the coloring composition of the present invention may contain a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.).
  • 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.
  • the polymerization inhibitor may be one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
  • the coloring composition of the present invention may contain a silane coupling agent.
  • the silane coupling agent include silane compounds having a hydrolyzable group, and it is preferable that the silane coupling agent is 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 can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
  • Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable.
  • the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable.
  • Specific examples of the silane coupling agent include the compounds described in paragraph 0177 of International Publication No.
  • 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.
  • the silane coupling agent may be one type or two or more types. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the coloring composition of the present invention may contain a surfactant.
  • a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant may be used.
  • the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant, and more preferably a silicone-based surfactant.
  • the surfactants described in paragraphs 0238 to 0245 of WO 2015/166779 may be referred to, the contents of which are incorporated herein by reference.
  • Nonionic surfactants include the compounds described in paragraph 0174 of WO 2022/085485.
  • Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (all manufactured by Dow Toray Co., Ltd.), TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (all manufactured by Momen Co., Ltd.).
  • Examples include BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, and BYK-UV3510 (manufactured by BYK-Chemie), etc.
  • silicone surfactant may also be a compound having the following structure:
  • 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, and more preferably 0.005% by mass to 3.0% by mass.
  • the surfactant may be one type or two or more types. When two or more types are used, it is preferable that the total amount is within the above range.
  • the coloring composition of the present invention may contain an antioxidant.
  • the antioxidant include phenolic compounds, phosphite compounds, and thioether compounds.
  • the phenolic compound any phenolic compound known as a phenolic antioxidant may be used.
  • a preferred phenolic compound is a hindered phenolic compound.
  • a compound having a substituent at the site (ortho position) adjacent to the phenolic hydroxy group is preferred.
  • a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
  • the antioxidant is also preferably a compound having a phenolic group and a phosphite group in the same molecule.
  • a phosphorus-based antioxidant may also be suitably used as the antioxidant.
  • phosphorus-based antioxidants include 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, and ethylbis(2,4-di-tert-butyl-6-methylphenyl)phosphite.
  • antioxidants include, for example, Adeka STAB AO-20, Adeka STAB AO-30, Adeka STAB AO-40, Adeka STAB AO-50, Adeka STAB AO-50F, Adeka STAB AO-60, Adeka STAB AO-60G, Adeka STAB AO-80, and Adeka STAB AO-330 (manufactured by ADEKA Corporation).
  • the antioxidant may be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. WO 2017/006600, a compound described in International Publication No. WO 2017/164024, or a compound described in Korean Patent Publication No. 10-2019-0059371.
  • the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20 mass%, more preferably 0.3 to 15 mass%. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is in the above range.
  • the coloring composition of the present invention may contain, as necessary, a sensitizer, a plasticizer, and other auxiliaries (for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.).
  • auxiliaries for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.
  • the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
  • the metal oxide 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, and even more preferably 5 to 50 nm.
  • the metal oxide may have a core-shell structure. In this case, the core may be hollow.
  • the coloring composition of the present invention may contain a light resistance improver.
  • the light resistance improver include the compounds described in paragraph 0183 of WO 2022/085485.
  • the coloring composition of the present invention is substantially free of terephthalic acid ester.
  • “substantially free of” means that the content of terephthalic acid ester in the total amount of the coloring composition is 1000 mass ppb or less, more preferably 100 mass ppb or less, and particularly preferably zero.
  • the colored composition of the present invention preferably has a melamine content of 10,000 ppm by mass or less.
  • the coloring composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less.
  • the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less.
  • Methods for reducing free metals and halogens in the coloring composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with ion-exchange resins.
  • the use of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts may be restricted.
  • the content of perfluoroalkylsulfonic acid (particularly perfluoroalkylsulfonic acid having a perfluoroalkyl group with 6 to 8 carbon atoms) and its salts, and perfluoroalkylcarboxylic acid (particularly perfluoroalkyl carboxylic acid having a perfluoroalkyl group with 6 to 8 carbon atoms) and its salts is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on 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 coloring composition that is substantially free of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts may be selected by using a compound that can be a substitute for perfluoroalkylsulfonic acid and its salts, and a compound that can be a substitute for perfluoroalkylcarboxylic acid and its salts.
  • Examples of compounds that can be a substitute for regulated compounds include compounds that are excluded from the scope of regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group. 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 allowable 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, and more preferably in the range of 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 with its viscosity adjusted for the purpose of adjusting the film surface state (flatness, etc.), adjusting the film thickness, etc.
  • the viscosity value can be appropriately selected as needed, but for example, it is preferably 0.3 mPa ⁇ s to 50 mPa ⁇ s at 25°C, and more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s.
  • the viscosity can be measured, for example, using a cone-plate type viscometer with the temperature adjusted to 25°C.
  • the container for storing the coloring composition is not particularly limited, and a known container can be used.
  • the container described in paragraph 0187 of WO 2022/085485 can be used as the container.
  • the coloring composition of the present invention can be prepared by mixing the above-mentioned components.
  • all the components may be dissolved and/or dispersed in a solvent at the same time to prepare the coloring composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to prepare the coloring composition.
  • the preparation of the coloring composition includes a process for dispersing the pigment.
  • examples of mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation. 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, and ultrasonic dispersion.
  • beads with a small diameter increase the bead packing rate, and perform the process under conditions that increase the grinding efficiency.
  • the process and dispersing machine for dispersing the pigment can be suitably used as described in "Dispersion Technology Encyclopedia, published by Joho Kika Co., Ltd., July 15, 2005” or "Dispersion Technology and Industrial Applications Focused on Suspension (Solid/Liquid Dispersion System) - Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978", and in paragraph 0022 of JP2015-157893A.
  • a salt milling process may be performed to refine the particles.
  • the descriptions in, for example, JP2015-194521A and JP2012-046629A can be referred to.
  • the coloring composition When preparing the coloring composition, it is preferable to filter the coloring composition with a filter for the purpose of removing foreign matter and reducing defects.
  • filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022/085485.
  • the film of the present invention is a film obtained from the above-mentioned coloring composition of the present invention.
  • the film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
  • the thickness of the film of the present invention can be adjusted appropriately depending on the purpose.
  • the thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
  • the film of the present invention when used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta or yellow hue, and more preferably has a red hue.
  • the film of the present invention can also 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, and red pixels are preferred.
  • the film of the present invention preferably has, for example, any one of the following spectral characteristics (1) to (4).
  • the maximum light transmittance in the thickness direction of the film 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 light transmittance in the thickness direction of the film in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light with a wavelength of more than 700 nm.
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength of more than 850 nm.
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength of more than 940 nm.
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength of more than 1040 nm.
  • the film of the present invention can be produced through a step of applying the coloring composition of the present invention.
  • Examples of the method for forming the pattern (pixel) include a photolithography method and a dry etching method, and the photolithography method is preferable.
  • Pattern formation by photolithography preferably includes a step of forming a coloring composition layer on a support using the coloring composition of the present invention, a step of exposing the coloring composition layer in a pattern, and a step of developing and removing the unexposed parts of the coloring composition layer to form a pattern (pixels). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
  • the coloring composition layer is formed on a support using the coloring composition of the present invention.
  • the support is not particularly limited and can be appropriately selected depending on the application.
  • a glass substrate, a silicon substrate, etc. can be mentioned, and a silicon substrate is preferable.
  • a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate.
  • CMOS complementary metal oxide semiconductor
  • a black matrix that isolates each pixel may be formed on the silicon substrate.
  • a base layer may be provided on the silicon substrate to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface.
  • the surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane. It is also preferable that the surface contact angle is 30 to 80° when measured with water.
  • a known method can be used to apply the coloring composition.
  • the application method described in paragraph 0207 of WO 2022/085485 can be used.
  • the colored composition layer formed on the support may be dried (prebaked).
  • prebaking may not be performed.
  • the prebaking temperature is preferably 150°C or less, more preferably 120°C or less, and even more preferably 110°C or less.
  • the lower limit can be, for example, 50°C or more, and can also be 80°C or more.
  • the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, etc.
  • the colored composition layer is exposed to light in a pattern (exposure step).
  • the colored composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed parts to be cured.
  • Radiation (light) that can be used for exposure includes g-rays and i-rays.
  • Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
  • Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred.
  • Long-wave light sources of 300 nm or more can also be used.
  • As light sources electrodeless ultraviolet lamp systems and hybrid curing of ultraviolet and infrared rays can be used.
  • Pulse exposure is an exposure method in which light is applied and paused repeatedly in short cycles (e.g., milliseconds or less).
  • the irradiation amount 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 during exposure can be appropriately selected, and in addition to being performed under air, for example, exposure may be performed under a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or under a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%).
  • the exposure illuminance can be appropriately set, and can usually be selected from the range of 1000 W/m 2 to 100,000 W/m 2 (e.g., 5,000 W/m 2 , 15,000 W/m 2 , or 35,000 W/m 2 ).
  • the oxygen concentration and exposure illuminance may be appropriately combined. For example, an oxygen concentration of 10% by volume and an illuminance of 10,000 W/m 2 , and an oxygen concentration of 35% by volume and an illuminance of 20,000 W/m 2 , can be used.
  • the unexposed parts of the coloring composition layer are developed and removed to form a pattern (pixels).
  • the unexposed parts of the coloring composition layer can be developed and removed using a developer.
  • the coloring composition layer in the unexposed parts in the exposure step dissolves into the developer, and only the photocured parts remain.
  • the temperature of the developer is preferably, for example, 20 to 30°C.
  • the development time is preferably 20 to 180 seconds.
  • the process of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
  • the developer may be an organic solvent or an alkaline developer, with an alkaline developer being preferred.
  • the developer and the washing (rinsing) method after development may be as described in paragraph 0214 of WO 2022/085485.
  • Additional exposure processing and post-baking are curing processing after development to complete curing.
  • the heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C.
  • Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • the light used for exposure has a wavelength of 400 nm or less.
  • additional exposure processing may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
  • the pattern formation by the dry etching method preferably includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, curing the entire colored composition layer to form a cured layer, forming a photoresist layer on the cured layer, exposing the photoresist layer in a pattern and developing it to form a resist pattern, and dry etching the cured layer using an etching gas with the resist pattern as a mask.
  • the process of forming the photoresist layer is preferably a form in which a heat treatment after exposure and a heat treatment after development (post-bake treatment) are performed.
  • the description in paragraphs 0010 to 0067 of JP 2013-064993 A can be referred to, and the contents of this specification are incorporated herein.
  • the optical filter of the present invention has the above-mentioned film of the present invention.
  • the types of optical filters include color filters and infrared transmission filters, and the color filter is preferable.
  • the color filter preferably has the film of the present invention as a color pixel of the color filter.
  • the optical filter may have a protective layer on the surface of the film of the present invention.
  • a protective layer By providing a protective layer, various functions such as oxygen blocking, low reflection, hydrophilicity/hydrophobicity, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
  • the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
  • Methods for forming the protective layer include a method of forming the protective layer by applying a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
  • the components constituting the protective layer include (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine resin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4 , etc., and may contain two or more of these components.
  • the protective layer in the case of a protective layer intended for oxygen blocking, preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
  • the protective layer in the case of a protective layer intended to reduce reflection, preferably contains a (meth)acrylic resin and a fluorine resin.
  • a protective layer by applying a resin composition When forming a protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as a method for applying the resin composition.
  • Known organic solvents e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
  • known chemical vapor deposition methods thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition
  • the protective layer may contain additives such as organic or inorganic fine particles, absorbents for light of specific wavelengths (e.g., ultraviolet light, near infrared light, etc.), refractive index adjusters, antioxidants, adhesion agents, and surfactants, as necessary.
  • organic or inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silica, calcium carbonate, and barium sulfate.
  • Known absorbents can be used as absorbents for light of specific wavelengths.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass, based on the total mass of the protective layer.
  • the protective layer may also be the one described in paragraphs 0073 to 0092 of JP2017-151176A.
  • the optical filter may have a structure in which each pixel is embedded in a space partitioned by partitions, for example in a grid pattern.
  • the solid-state imaging device of the present invention has the above-mentioned film of the present invention.
  • the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, and examples thereof include the following configurations.
  • the substrate has a plurality of photodiodes constituting the light receiving area of a solid-state imaging element (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light-shielding film on the photodiodes and the transfer electrodes with only the light receiving portion of the photodiodes open, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film.
  • a solid-state imaging element such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor
  • a transfer electrode made of polysilicon or the like
  • the device protection film may have a light-collecting means (e.g., a microlens, etc.; the same applies below) on the device protection film and below the color filter (the side closer to the substrate), or a light-collecting means on the color filter.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example in a lattice shape. In this case, it is preferable that the partitions have a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, and WO 2018/043654 A.
  • the image display device of the present invention has the above-mentioned film of the present invention.
  • Examples of the image display device include liquid crystal display devices and organic electroluminescence display devices.
  • the definition of the image display device and details of each image display device are described, for example, in "Electronic Display Devices” (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and “Display Devices” (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1989).
  • the liquid crystal display device is described, for example, in “Next Generation Liquid Crystal Display Technology” (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994).
  • There is no particular limitation on the liquid crystal display device to which the present invention can be applied and the present invention can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology".
  • Dispersion treatment (Dispersions R-1 to R-74, Y-1, Y-2, CR-1) A mixture of pigment 1, pigment 2, resin, pigment derivative, and solvent in the ratios shown below was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.3 mm diameter). Thereafter, a dispersion treatment was carried out at a flow rate of 500 g/min under a pressure of 2000 kg/ cm2 using a high-pressure disperser NANO-3000-10 (manufactured by Japan BEE Co., Ltd.) equipped with a pressure reducing mechanism. This dispersion treatment was repeated 10 times to obtain each dispersion.
  • the ratios shown for pigment 1 are molar ratios.
  • the ratios shown for pigment 2 and the solvent are mass ratios.
  • PR254 C.I. Pigment Red 254 PR255: C.I. Pigment Red 255 PR264: C.I. Pigment Red 264 PR272: C.I. Pigment Red 272 PR291: C.I. Pigment Red 291 PO71: C.I. Pigment Orange 71 PO73: C.I. Pigment Orange 73 PY139: C.I. Pigment Yellow 139 PY185: C.I. Pigment Yellow 185 CP-1: Compound having the following structure
  • M-1 A mixture of compounds having the following structure (a mixture of the compound on the left (a hexafunctional (meth)acrylate compound) and the compound on the right (a pentafunctional (meth)acrylate compound) in a molar ratio of 7:3)
  • M-2 Compound having the following structure
  • M-3 Compound having the following structure
  • M-4 Compound having the following structure
  • (Surfactant) K-1 A propylene glycol monomethyl ether acetate solution having a solids concentration of 1% by mass of a compound having the following structure (weight average molecular weight 3000, silicone surfactant)
  • K-2 A propylene glycol monomethyl ether acetate solution having a solids concentration of 1% by mass of a compound having the following structure (the percentage indicating the proportion of repeating units is mol %; weight average molecular weight: 14000, fluorosurfactant)
  • the obtained film was observed at a magnification of 30,000 times using a scanning electron microscope, and the storage stability was evaluated according to the following evaluation criteria.
  • This composition layer was exposed by irradiating light with a wavelength of 365 nm at an exposure amount of 200 mJ / cm 2 using an i-line stepper FPA-3000i5 + (manufactured by Canon Co., Ltd.) through a mask pattern in which square pixels with a side of 1.1 ⁇ m were arranged in an area of 4 mm ⁇ 3 mm on the substrate.
  • the composition layer after exposure was subjected to paddle development at 23 ° C. for 60 seconds using a 0.3 mass % aqueous solution of tetramethylammonium hydroxide as a developer. Thereafter, it was rinsed with water in a spin shower and further washed with pure water.
  • the water droplets were blown off with high-pressure air, the silicon wafer was naturally dried, and then post-baked for 300 seconds at 200° C. using a hot plate to form pixels.
  • the outside of the pixel formation region (unexposed area) was observed with a scanning electron microscope (magnification 10,000 times), and residues with a diameter of 0.1 ⁇ m or more per 5 ⁇ m ⁇ 5 ⁇ m area (1 area) of the unexposed area were counted, and the development residues were evaluated according to the following evaluation criteria.
  • B The number of residues per area is 1 or more and less than 10.
  • C The number of residues per area is 10 or more and less than 20.
  • D The number of residues per area is 20 or more and less than 30.
  • E Development was possible, but the number of residues per area was 30 or more.
  • F Development was not possible at all.
  • the coloring compositions of the examples had excellent storage stability. Furthermore, the generation of development residues was suppressed.
  • Example 119 A colored composition of Example 119 was produced in the same manner as in Example 89, except that the photopolymerization initiator I-1 and the polymerizable compound M-1 in Example 89 were changed to an epoxy compound (EHPE3150, manufactured by Daicel Corporation). The storage stability of the obtained colored composition was evaluated by the same method as above, and the composition was rated as A.
  • EHPE3150 an epoxy compound
  • the films formed from the colored compositions of the examples can be suitably used in optical filters, solid-state imaging devices, and image display devices.

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  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'invention concerne une composition colorante qui contient un agent colorant, une résine et un solvant, l'agent colorant contenant un composé représenté par la formule (1). Dans la formule (1), R1 et R2 représente chacun indépendamment un atome d'hydrogène ou un substituant ; R3 représente un substituant ; L1 représente un groupe de liaison m-valent ; et m représente un nombre entier compris entre 2 et 6. L'invention concerne également : un film qui fait appel à cette composition colorante ; un filtre optique ; un élément d'imagerie à semi-conducteurs ; et un dispositif d'affichage d'image.
PCT/JP2024/003388 2023-02-16 2024-02-02 Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Ceased WO2024171839A1 (fr)

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JP2025501052A JPWO2024171839A1 (fr) 2023-02-16 2024-02-02

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JP2023-022382 2023-02-16
JP2023022382 2023-02-16

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WO2024171839A1 true WO2024171839A1 (fr) 2024-08-22

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PCT/JP2024/003388 Ceased WO2024171839A1 (fr) 2023-02-16 2024-02-02 Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image

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JP (1) JPWO2024171839A1 (fr)
TW (1) TW202436528A (fr)
WO (1) WO2024171839A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009037350A2 (fr) * 2007-09-21 2009-03-26 L'oreal COLORANT THIOL/DISULFURE DICÉTOPYRROLO[3,4-c]PYRROLE, COMPOSITION COLORANTE COMPRENANT LEDIT COLORANT, PROCÉDÉ D'ÉCLAIRCISSEMENT DE MATÉRIAUX À BASE DE KÉRATINE AU MOYEN DE CE COLORANT
KR20120009706A (ko) * 2010-07-20 2012-02-02 가톨릭대학교 산학협력단 안료 화합물, 이를 포함하는 안료 분산액, 이를 이용한 컬러필터 및 이를 이용한 이미지센서
JP2012207106A (ja) * 2011-03-29 2012-10-25 Dainippon Printing Co Ltd カラーフィルター用インクジェットインク、カラーフィルターの製造方法、カラーフィルター、液晶表示装置及び有機発光表示装置
WO2021235322A1 (fr) * 2020-05-21 2021-11-25 東洋インキＳｃホールディングス株式会社 Composition de pigments destinée à des filtres colorés, composition colorante, filtre coloré, dispositif d'affichage à cristaux liquides, et élément d'imagerie à semi-conducteurs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009037350A2 (fr) * 2007-09-21 2009-03-26 L'oreal COLORANT THIOL/DISULFURE DICÉTOPYRROLO[3,4-c]PYRROLE, COMPOSITION COLORANTE COMPRENANT LEDIT COLORANT, PROCÉDÉ D'ÉCLAIRCISSEMENT DE MATÉRIAUX À BASE DE KÉRATINE AU MOYEN DE CE COLORANT
KR20120009706A (ko) * 2010-07-20 2012-02-02 가톨릭대학교 산학협력단 안료 화합물, 이를 포함하는 안료 분산액, 이를 이용한 컬러필터 및 이를 이용한 이미지센서
JP2012207106A (ja) * 2011-03-29 2012-10-25 Dainippon Printing Co Ltd カラーフィルター用インクジェットインク、カラーフィルターの製造方法、カラーフィルター、液晶表示装置及び有機発光表示装置
WO2021235322A1 (fr) * 2020-05-21 2021-11-25 東洋インキＳｃホールディングス株式会社 Composition de pigments destinée à des filtres colorés, composition colorante, filtre coloré, dispositif d'affichage à cristaux liquides, et élément d'imagerie à semi-conducteurs

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JPWO2024171839A1 (fr) 2024-08-22
TW202436528A (zh) 2024-09-16

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