WO2022191044A1 - 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置、赤外線センサ、カメラモジュール、化合物および赤外線吸収剤 - Google Patents
組成物、膜、光学フィルタ、固体撮像素子、画像表示装置、赤外線センサ、カメラモジュール、化合物および赤外線吸収剤 Download PDFInfo
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- WO2022191044A1 WO2022191044A1 PCT/JP2022/009246 JP2022009246W WO2022191044A1 WO 2022191044 A1 WO2022191044 A1 WO 2022191044A1 JP 2022009246 W JP2022009246 W JP 2022009246W WO 2022191044 A1 WO2022191044 A1 WO 2022191044A1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
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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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C08K5/55—Boron-containing compounds
-
- 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
-
- 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
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Definitions
- the present invention relates to compositions containing pyrrolopyrrole compounds.
- the present invention also relates to a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor and a camera module using the composition described above.
- the present invention also relates to pyrrolopyrrole compounds and infrared absorbers.
- CCDs charge-coupled devices
- CMOSs complementary metal-oxide semiconductors
- CCDs charge-coupled devices
- CMOSs complementary metal-oxide semiconductors
- These solid-state imaging devices use silicon photodiodes that are sensitive to infrared rays in their light receiving portions. For this reason, an infrared cut filter may be provided to correct visibility.
- the infrared cut filter is manufactured using a composition containing infrared absorbing pigments. Pyrrolopyrrole compounds and the like are known as infrared absorbing dyes.
- Patent Document 1 describes that a compound represented by the following formula (I) is used in a solar cell module or the like.
- the fluorescence quantum yield of the film is low. If the fluorescence quantum yield of the membrane is high, fluorescence emission from the membrane tends to be noise.
- Patent Document 2 is an invention aimed at increasing the fluorescence quantum yield. Further, when the present inventor proceeded with the study of the compound described in Patent Document 2, it was found that there is room for further improvement in terms of visible transparency as well.
- * represents a connecting portion
- R a11 to R a29 each independently represent a hydrogen atom or a substituent
- X c and X d each independently represent S, O or NR X2
- R X2 represents a hydrogen atom or a substituent
- a 1 represents an optionally substituted aromatic hydrocarbon ring, aromatic heterocyclic ring, or condensed ring thereof.
- X a and X b in formula (1) are each independently a group represented by any one of formulas (X-1-1) to (X-1-3), ⁇ 1> A composition according to In formulas (X-1-1) to (X-1-3), * represents a connecting part, R a51 to R a63 each independently represent a hydrogen atom or a substituent, two adjacent groups among R a51 to R a54 of formula (X-1-1) may be bonded to form a ring, two adjacent groups of R a55 to R a58 in formula (X-1-2) may be bonded to form a ring, Two adjacent groups among R a60 to R a63 in formula (X-1-3) may be bonded to form a ring.
- Y a and Y b in formula (1) each independently represent —BR Y1 R Y2
- R Y1 and R Y2 each independently represent a hydrogen atom, a halogen atom, an alkyl group, or an alkenyl group , represents an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group or a heteroaryloxy group, and R Y1 and R Y2 may combine with each other to form a ring
- ⁇ 6> The composition according to any one of ⁇ 1> to ⁇ 5>, wherein the dye represented by formula (1) has a maximum absorption wavelength of 650 nm or longer.
- ⁇ 7> A film obtained using the composition according to any one of ⁇ 1> to ⁇ 6>.
- ⁇ 8> An optical filter including the film according to ⁇ 7>.
- ⁇ 9> A solid-state imaging device including the film according to ⁇ 7>.
- An image display device comprising the film according to ⁇ 7>.
- An infrared sensor including the film according to ⁇ 7>.
- ⁇ 12> A camera module including the film according to ⁇ 7>.
- * represents a connecting portion
- R a11 to R a29 each independently represent a hydrogen atom or a substituent
- X c and X d each independently represent S, O or NR X2
- R X2 represents a hydrogen atom or a substituent
- a 1 represents an optionally substituted aromatic hydrocarbon ring, aromatic heterocyclic ring, or condensed ring thereof.
- a composition capable of forming a film having a low fluorescence quantum yield and excellent spectral characteristics.
- a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, a camera module, a compound, and an infrared absorber can be provided.
- FIG. 1 is a schematic diagram illustrating one embodiment of an infrared sensor
- ⁇ is used to include the numerical values before and after it as lower and upper limits.
- a description that does not describe substitution or unsubstituted includes a group (atomic group) having no substituent as well as a group (atomic group) having a substituent.
- an "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- EUV light extreme ultraviolet rays
- (meth)acrylate” represents both or either acrylate and methacrylate
- (meth)acryl represents both or either acrylic and methacrylic
- (meth) ) acryloyl refers to acryloyl and/or methacryloyl.
- the weight average molecular weight and number average molecular weight are defined as polystyrene equivalent values in gel permeation chromatography (GPC) measurement.
- GPC gel permeation chromatography
- Me in the chemical formulas represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- infrared light refers to light (electromagnetic waves) with a wavelength of 700 to 2500 nm.
- total solid content refers to the total mass of all components of the composition excluding the solvent.
- a pigment means a compound that is difficult to dissolve in a solvent.
- the term "process” includes not only an independent process, but also when the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. .
- composition of the present invention is characterized by containing a dye represented by Formula (1) and a curable compound.
- the composition of the present invention can be used as a composition for optical filters.
- Types of optical filters include infrared cut filters and infrared transmission filters. Since the dye represented by the formula (1) has excellent visible transparency, an infrared cut filter having excellent visible transparency can be formed by using the composition of the present invention. Further, in the infrared transmission filter, the dye represented by the formula (1) has a role of limiting transmitted light (infrared rays) to a longer wavelength side. Since the dye represented by the formula (1) is excellent in visible transparency, it is easy to control the spectrum in the visible region to be shielded and the spectrum in the infrared region to be transmitted within an appropriate range.
- the composition of the present invention contains a dye represented by Formula (1) (hereinafter also referred to as a specific dye).
- * represents a connecting portion
- R a11 to R a29 each independently represent a hydrogen atom or a substituent
- X c and X d each independently represent S, O or NR X2
- R X2 represents a hydrogen atom or a substituent
- a 1 represents an optionally substituted aromatic hydrocarbon ring, aromatic heterocyclic ring, or condensed ring thereof.
- X a and X b each independently represent ⁇ NR X1 or a group represented by any one of formulas (X-1) to (X-5).
- the substituent represented by R X1 is preferably an aryl group or a heteroaryl group, more preferably a heteroaryl group.
- the number of carbon atoms in the aryl group is preferably 6-40, more preferably 6-30, even more preferably 6-20.
- the aryl group may be monocyclic, but is preferably a condensed ring.
- a heteroaryl group may be a monocyclic ring, but preferably a condensed ring.
- the number of heteroatoms constituting the heteroaryl ring of the heteroaryl group is preferably 1-3.
- a heteroatom constituting the heteroaryl ring is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the heteroaryl ring is preferably 3-30, more preferably 3-18, even more preferably 3-12.
- the heteroaryl ring is preferably a 5- or 6-membered ring.
- the aryl group and heteroaryl group may have a substituent or may be unsubstituted.
- substituents include the groups listed for the substituent T described later and the groups represented by the formula (R-100) described later, and include a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an acyl group, and an alkoxycarbonyl group.
- substituents represented by R a11 to R a29 in formulas (X-1) to (X-5) include groups exemplified for substituent T described later and groups represented by formula (R-100) described later.
- a sulfo group or a group represented by the formula (R-100) is preferable, and a halogen atom, an alkyl group, an alkoxy group, an acyl group, an aryl group, an aryloxy group, a hydroxy group, a carboxyl group, a sulfonamide group, or an imide more preferably a group or a sulfo group.
- X c and X d in formulas (X-1) to (X-5) each independently represent S, O or NR X2
- R X2 represents a hydrogen atom or a substituent.
- the substituent represented by R X2 includes an alkyl group, an alkoxy group, an acyl group, an allyl group and an aryloxy group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, and even more preferably 1-3.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- R X2 is preferably a hydrogen atom or a methyl group, more preferably a methyl group.
- a 1 in formula (X-1) represents an optionally substituted aromatic hydrocarbon ring, aromatic heterocyclic ring, or condensed ring thereof.
- a benzene ring, a naphthalene ring, etc. are mentioned as said aromatic-hydrocarbon ring.
- the aromatic heterocyclic ring include imidazole ring, pyrazole ring, oxazole ring, thiazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, isothiazole ring and isoxazole ring.
- condensed ring examples include benzimidazole ring, benzopyrazole ring, benzoxazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, quinazoline ring, and quinoxaline ring.
- substituents examples include the groups listed for the substituent T described later and the groups represented by the formula (R-100) described later, and include a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an acyl group, and an alkoxycarbonyl group, an acyloxy group, an aryl group, an aryloxy group, a hydroxy group, a carboxyl group, a carboxylic acid amide group, a sulfonamide group, an imide group, a sulfo group or a group represented by the formula (R-100),
- a halogen atom, an alkyl group, an alkoxy group, an acyl group, an aryl group, an aryloxy group, a hydroxy group, a carboxyl group, a sulfonamide group, an imide group, or a sulfo group is more preferred.
- the group represented by formula (X-1) is preferably a group represented by any one of formulas (X-1-1) to (X-1-3).
- * represents a connecting part
- R a51 to R a63 each independently represent a hydrogen atom or a substituent
- two adjacent groups among R a51 to R a54 of formula (X-1-1) may be bonded to form a ring
- two adjacent groups of R a55 to R a58 in formula (X-1-2) may be bonded to form a ring
- Two adjacent groups among R a60 to R a63 in formula (X-1-3) may be bonded to form a ring.
- substituents represented by R a51 to R a63 in formulas (X-1-1) to (X-1-3) include the groups exemplified for the substituent T described later and those represented by the formula (R-100) described later. group.
- Substituents represented by R a51 to R a58 and R a60 to R a63 are halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, acyl groups, alkoxycarbonyl groups, acyloxy groups, aryl groups, aryloxy groups, hydroxy groups, and carboxyl groups.
- R a59 is preferably an alkyl group, an alkoxy group, an acyl group, an allyl group or an aryloxy group, more preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, and even more preferably 1-3.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- R a59 is preferably a hydrogen atom or a methyl group, more preferably a methyl group.
- Two adjacent groups among R a51 to R a54 of formula (X-1-1) may be bonded to form a ring, and R a55 to R a58 of formula (X-1-2) Of these, two adjacent groups may be bonded together to form a ring, and two adjacent groups among R a60 to R a63 of formula (X-1-3) are bonded together to form a ring.
- the ring formed by combining these groups is preferably a 5- or 6-membered ring.
- the formed ring examples include benzene ring, pyrrole ring, furan ring, thiophene ring, oxazole ring, thiazole ring, imidazole ring, pyridine ring, pyrimidine ring, pyran ring, isothiazole ring, isoxazole ring, pyridazine ring, A pyrazine ring, a cyclohexane ring, a cyclopentane ring, a combination thereof, and the like are included.
- is preferably a group, and for the reason that it is possible to obtain better visible transparency, it is more preferably a group represented by NR X1 or formula (X-1), visible transparency, light resistance
- a group represented by any one of formulas (X-1-1) to (X-1-3) is more preferable because it can achieve a high level of both heat resistance and heat resistance.
- R 1 and R 2 in formula (1) each independently represent an optionally substituted aliphatic hydrocarbon group.
- the aliphatic hydrocarbon group represented by R 1 and R 2 may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
- the aliphatic hydrocarbon group represented by R 1 and R 2 may be linear, branched or cyclic.
- the cyclic aliphatic hydrocarbon group may be any of a monocyclic aliphatic hydrocarbon group, a condensed-ring aliphatic hydrocarbon group, and a bridged-ring aliphatic hydrocarbon group. It is preferably a group.
- the aliphatic hydrocarbon group represented by R 1 and R 2 may have a substituent.
- substituents include the groups listed for the substituent T described later and the groups represented by the formula (R-100) described later, halogen atoms, alkoxy groups, alkylthio groups, ureido groups, acyl groups, alkoxycarbonyl groups, It is preferably an acyloxy group, a sulfamoyl group, an aryl group, an aryloxy group, a hydroxy group, a carboxyl group, a carboxylic acid amide group, a sulfonamide group, an imide group, a sulfo group or a group represented by the formula (R-100).
- R 1 in formula (1) may be the same group as R 2 , but is preferably a different group (ie asymmetric).
- aliphatic hydrocarbon groups include alkyl groups, alkenyl groups, and alkynyl groups.
- the number of carbon atoms in the alkyl group is preferably 1-30.
- the lower limit is preferably 3 or more.
- the upper limit of the number of carbon atoms in the alkyl group is preferably 15 or less, more preferably 10 or less, and even more preferably 7 or less.
- the specific colorant is a dye
- the upper limit of the number of carbon atoms in the alkyl group is preferably 25 or less, more preferably 19 or less.
- Alkyl groups may be linear, branched or cyclic.
- the alkenyl group preferably has 2 to 30 carbon atoms.
- the lower limit is preferably 3 or more.
- the upper limit of the number of carbon atoms in the alkenyl group is preferably 15 or less, more preferably 10 or less, and even more preferably 7 or less.
- the specific colorant is a dye
- the upper limit of the number of carbon atoms in the alkenyl group is preferably 25 or less, more preferably 19 or less.
- Alkenyl groups may be linear, branched or cyclic.
- the alkynyl group preferably has 2 to 30 carbon atoms.
- the lower limit is preferably 3 or more.
- the upper limit of the number of carbon atoms in the alkynyl group is preferably 15 or less, more preferably 10 or less, and even more preferably 7 or less.
- the upper limit of the number of carbon atoms in the alkynyl group is preferably 25 or less, more preferably 19 or less.
- Alkynyl groups may be linear, branched or cyclic. Alkyl groups, alkenyl groups and alkynyl groups may have a substituent or may be unsubstituted.
- substituents include the groups listed for the substituent T described later and the groups represented by the formula (R-100) described later, and include a halogen atom, an alkoxy group, an alkylthio group, a ureido group, an acyl group, an alkoxycarbonyl group, It is preferably an acyloxy group, a sulfamoyl group, an aryl group, an aryloxy group, a hydroxy group, a carboxyl group, a carboxylic acid amide group, a sulfonamide group, an imide group, a sulfo group or a group represented by the formula (R-100). .
- L R1 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -NR L1 -, -CO-, -COO-, - OCO—, —SO 2 —, or an n+1-valent linking group consisting of a combination thereof
- R L1 represents a hydrogen atom, an alkyl group or an aryl group
- X R1 represents an acid group or a basic group
- n represents an integer of 1 or more.
- L R1 may be a single bond.
- the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-20, more preferably 2-20, still more preferably 2-10, and particularly preferably 2-5.
- the aliphatic hydrocarbon group may be linear, branched or cyclic.
- the aliphatic hydrocarbon group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- the number of carbon atoms in the aromatic hydrocarbon group is preferably 6-18, more preferably 6-14, even more preferably 6-10.
- the aromatic hydrocarbon group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- the heterocyclic group is preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3.
- a heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3-30, more preferably 3-18, and more preferably 3-12.
- heterocyclic groups include piperazine ring group, pyrrolidine ring group, pyrrole ring group, piperidine ring group, pyridine ring group, imidazole ring group, pyrazole ring group, oxazole ring group, thiazole ring group, pyrazine ring group, morpholine ring group, thiazine ring group, indole ring group, isoindole ring group, benzimidazole ring group, purine ring group, quinoline ring group, isoquinoline ring group, quinoxaline ring group, cinnoline ring group, carbazole ring group and the following formula (L- 1) to groups represented by (L-7).
- * in the formula represents a connecting part.
- R represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent.
- substituents include the groups exemplified for the substituent T described later, preferably a halogen atom, more preferably a fluorine atom.
- the number of carbon atoms in the alkyl group represented by R L1 is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group represented by R L1 may further have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- the aryl group represented by R L1 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryl group represented by R L1 may further have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- Examples of the acid group represented by X R1 of the formula (R-100) include a carboxyl group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonamide group, an imidic acid group and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
- a group represented by —NHCOR XR1 is preferable.
- a group represented by —NHSO 2 R XR2 is preferable.
- the imidic acid group is preferably a group represented by —SO 2 NHSO 2 R XR3 , —CONHSO 2 R XR4 , —CONHCOR XR5 or —SO 2 NHCOR XR6 , and —CONHSO 2 R XR4 or —SO 2 NHSO 2 R.
- XR3 is more preferred.
- R XR1 to R XR6 each independently represent an alkyl group or an aryl group.
- the alkyl groups and aryl groups represented by R XR1 to R XR6 may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups represented by X R1 of formula (R-100) include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
- Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- the amino group includes groups represented by —NRx R1 Rx R2 and cyclic amino groups.
- Rx R1 and Rx R2 each independently represent a hydrogen atom, an alkyl group or an aryl group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, and even more preferably 1-3.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- the aryl group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later. Also, Rx R1 and Rx R2 may combine to form a ring. Cyclic amino groups include a pyrrolidine group, a piperidine group, a piperazine group, a morpholine group and the like. These groups may further have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later. Specific examples of substituents include alkyl groups and aryl groups.
- n in formula (R-100) represents an integer of 1 or more, preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.
- a preferred embodiment of formula (1) is an embodiment in which at least one of R 1 and R 2 in formula (1) is an optionally substituted alkyl group having 9 or less carbon atoms.
- the dye is a pigment
- the number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 5, even more preferably 1 to 4, and preferably 1 to 3.
- the dispersibility of the pigment is improved, and the generation of foreign matter in the pigment dispersion can be suppressed.
- the pigment is a dye
- the number of carbon atoms in the alkyl group is preferably 4 to 9, more preferably 5 to 9, still more preferably 6 to 9, and preferably 7 to 9. Especially preferred.
- the alkyl group having 9 or less carbon atoms is preferably branched. According to this aspect, it is possible to obtain the effect of suppressing the generation of foreign substances in the dye solution and the effect of suppressing defects in the film formed using the dye solution.
- substituents that the alkyl group having 9 or less carbon atoms can have include a halogen atom, an alkoxy group, an alkylthio group, a ureido group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a sulfamoyl group, a hydroxy group, a carboxyl group, A carboxylic acid amide group, a sulfonamide group, an imide group, a sulfo group, or a group represented by the above formula (R-100) can be mentioned, and a halogen atom is preferred.
- the alkyl group having 9 or less carbon atoms is preferably an unsubstituted alkyl group or an alkyl group having a halogen atom as a substituent (fluoroalkyl group).
- a preferred embodiment of formula (1) is an embodiment in which at least one of R 1 and R 2 in formula (1) is a group represented by formula (R-1). According to this aspect, associations are easily formed during film formation, and the heat resistance and light resistance of the resulting film can be further improved. In this aspect, when R 1 and R 2 in formula (1) are each a group represented by formula (R-1), the above-described effects are exhibited more remarkably.
- R 1 and R 2 in formula (1) are each a group represented by formula (R-1), the above-described effects are exhibited more remarkably.
- * represents a linking moiety
- R 101 and R 102 each independently represent a hydrogen atom or a substituent
- Ar 101 represents an aryl group or a heteroaryl group
- n represents 1 or more represents an integer.
- Substituents represented by R 101 and R 102 include an alkyl group, an aryl group and a heteroaryl group, preferably an alkyl group.
- R 101 and R 102 are each independently a hydrogen atom.
- Ar 101 represents an aryl group or a heteroaryl group, preferably an aryl group.
- n in formula (1) represents an integer of 1 or more, preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and even more preferably 1 or 2.
- the number of carbon atoms in the alkyl group represented by R 101 and R 102 is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, even more preferably 1 to 5, and 1 to 3. is particularly preferred.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- the number of carbon atoms in the aryl group represented by R 101 , R 102 and Ar 101 is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- the aryl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- the number of carbon atoms constituting the heteroaryl group represented by R 101 , R 102 and Ar 101 is preferably 1-30, more preferably 1-12.
- Types of heteroatoms that constitute the heteroaryl group include, for example, a nitrogen atom, an oxygen atom and a sulfur atom.
- the number of heteroatoms constituting the heteroaryl group is preferably 1-3, more preferably 1 or 2.
- the heteroaryl group is preferably a monocyclic ring or a condensed ring, more preferably a monocyclic ring or a condensed ring with 2 to 8 condensed numbers, and still more preferably a monocyclic ring or a condensed ring with 2 to 4 condensed numbers.
- a heteroaryl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- a preferred embodiment of formula (1) is an embodiment in which R 1 in formula (1) is a group with a different structure from R 2 .
- R 1 and R 2 are each independently an optionally substituted alkyl group, and R 1 preferably has a different structure from R 2 .
- Y a and Y b in formula (1) each independently represent a hydrogen atom or a substituent, preferably a substituent.
- Substituents represented by Y a and Y b in formula (1) include an alkyl group, an aryl group, a heteroaryl group, and —BR Y1 R Y2 , with —BR Y1 R Y2 being preferred.
- the number of carbon atoms in the alkyl group represented by Y 1 and Y 2 is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, even more preferably 1 to 5, and 1 to 3. is particularly preferred.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- the aryl group represented by Y 1 and Y 2 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- the number of carbon atoms constituting the heteroaryl group represented by Y 1 and Y 2 is preferably 1-30, more preferably 1-12.
- Types of heteroatoms that make up the heteroaryl group include, for example, a nitrogen atom, an oxygen atom and a sulfur atom.
- the number of heteroatoms constituting the heteroaryl group is preferably 1-3, more preferably 1 or 2.
- the heteroaryl group is preferably a monocyclic ring or a condensed ring, more preferably a monocyclic ring or a condensed ring with 2 to 8 condensed numbers, and still more preferably a monocyclic ring or a condensed ring with 2 to 4 condensed numbers.
- a heteroaryl group may have a substituent or may be unsubstituted. Examples of the substituent include the groups exemplified for the substituent T described later.
- R Y1 and R Y2 in the group represented by -BR Y1 R Y2 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group or a heteroaryl It represents an oxy group, preferably a halogen atom, an alkyl group, an aryl group or a heteroaryl group, more preferably a halogen atom, an alkyl group or an aryl group, even more preferably an aryl group.
- Halogen atoms represented by R Y1 and R Y2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, with a fluorine atom being preferred.
- the number of carbon atoms in the alkyl group and alkoxy group represented by R 1 Y1 and R 2 Y2 is preferably 1-40, more preferably 1-30, even more preferably 1-20.
- Alkyl groups and alkoxy groups may be linear, branched or cyclic, but are preferably linear or branched. An alkyl group and an alkoxy group may have a substituent or may be unsubstituted.
- Substituents include aryl groups, heteroaryl groups, halogen atoms, and the like.
- the alkenyl group represented by R Y1 and R Y2 preferably has 2 to 40 carbon atoms, more preferably 2 to 30 carbon atoms, and still more preferably 2 to 20 carbon atoms.
- the alkenyl group may have a substituent or may be unsubstituted. Examples of substituents include alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, and halogen atoms.
- the number of carbon atoms in the aryl group and aryloxy group represented by R Y1 and R Y2 is preferably 6-20, more preferably 6-12.
- the aryl group and aryloxy group may have a substituent or may be unsubstituted. Examples of substituents include alkyl groups, alkoxy groups, and halogen atoms.
- the heteroaryl group and heteroaryloxy group represented by R Y1 and R Y2 may be monocyclic or condensed.
- the number of heteroatoms constituting the heteroaryl ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3.
- a heteroatom constituting the heteroaryl ring is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the heteroaryl ring is preferably 3-30, more preferably 3-18, even more preferably 3-12.
- the heteroaryl ring is preferably a 5- or 6-membered ring.
- a heteroaryl group and a heteroaryloxy group may have a substituent or may be unsubstituted. Examples of substituents include alkyl groups, alkoxy groups, and halogen atoms.
- R Y1 and R Y2 in the group represented by -BR Y1 R Y2 may be combined to form a ring.
- Examples of the ring to be formed include structures shown in (B-1) to (B-5) below.
- Rb represents a substituent
- Rb 1 to Rb 4 each independently represent a hydrogen atom or a substituent
- b1 to b3 each independently represent an integer of 0 to 4
- b4 is 0 to 6 represents an integer
- * represents a connecting part.
- Substituents represented by Rb and Rb 1 to Rb 4 include the groups exemplified for the substituent T described later, preferably halogen atoms, alkyl groups and alkoxy groups.
- Substituent T includes the following groups.
- Halogen atom e.g., fluorine atom, chlorine atom, bromine atom, iodine atom
- alkyl group preferably alkyl group having 1 to 30 carbon atoms
- alkenyl group preferably alkenyl group having 2 to 30 carbon atoms
- alkynyl group Preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an aryl group having 6 to 30 carbon atoms
- a heteroaryl group preferably a heteroaryl group having 1 to 30 carbon atoms
- an amino group preferably amino group having 0 to 30 carbon atoms
- alkoxy group preferably alkoxy group having 1 to 30 carbon atoms
- aryloxy group preferably aryloxy group having 6 to 30 carbon atoms
- heteroaryloxy group preferably carbon 1 to 30 heteroaryloxy groups
- acyl groups preferably acyl groups having 2 to 30 carbon
- the maximum absorption wavelength of the specific dye preferably exists at a wavelength of 650 nm or more, more preferably in a wavelength range of 650 to 1500 nm, even more preferably in a wavelength range of 660 to 1200 nm, and a wavelength of 660 to 1000 nm. is particularly preferred.
- the specific dye has an average absorbance value of 0.00 in the wavelength range of 420 to 550 nm when the absorbance value at the wavelength ( ⁇ max) showing the maximum absorbance value in the wavelength range of 400 nm to 1200 nm is 1. It is preferably less than 010, more preferably less than 0.005.
- the absorbance and maximum absorption wavelength of a specific dye can be obtained by dissolving the specific dye in a solvent to prepare a dye solution and measuring the absorbance of the dye solution.
- Solvents used for preparing the dye solution include chloroform, dimethylsulfoxide (DMSO), tetrahydrofuran (THF) and the like.
- DMSO dimethylsulfoxide
- THF tetrahydrofuran
- the specific dye is a compound that dissolves in chloroform
- chloroform is used as the solvent.
- dimethylsulfoxide (DMSO) or tetrahydrofuran (THF) dimethylsulfoxide (DMSO) or tetrahydrofuran (THF) is used as the solvent.
- the average absorbance in the wavelength range of 420 to 550 nm is calculated by taking the weighted average of the normalized absorbance values in the wavelength range of 420 to 550 nm, with the absorbance at ⁇ max being 1.
- the specific colorant may be a pigment or a dye.
- R 1 and R 2 in formula (1) are the same group, at least one of R 1 and R 2 (preferably both) is a cyclic aliphatic hydrocarbon group, at least R 1 and R 2 One (preferably both) is a linear aliphatic hydrocarbon group, or at least one of R 1 and R 2 (preferably both) is an aliphatic hydrocarbon group having 6 or less carbon atoms, a dye It is possible to increase the crystallinity of the dye and reduce the solubility in a solvent, and such a specific dye can be preferably used as a pigment.
- R 1 and R 2 are different groups
- at least one of R 1 and R 2 is a branched aliphatic hydrocarbon group
- the specific dye may be a dye derivative.
- Dye derivatives are used, for example, as dispersing aids.
- a dispersing aid is a material that enhances the dispersibility of the pigment in the composition.
- a resin such as a dispersant
- a network can be formed between the pigment, the dispersing aid and the resin to further improve the dispersibility of the pigment.
- a compound having a structure in which at least one of X a , X b , Y a , Y b , R 1 and R 2 in formula (1) has a group represented by formula (R-100) as a substituent is a dispersing aid. It can be preferably used as an agent.
- a compound having such a structure can also be used as a pigment or dye. Details of the dye derivative will be described later.
- formula (1) also includes its resonance structure. That is, the compound having the resonance structure of formula (1) is also included in the specific dye of the present invention.
- specific dyes include compounds having structures described in the examples below (PPB-A-1 to PPB-A-45, PPB-B-1 to PPB-B-13, PPB-B-15, PPB -B-16, PPB-C-1 to PPB-C-3).
- the content of the specific pigment is preferably 0.5% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, based on the total solid content of the composition.
- the upper limit of the content of the specific dye is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
- the composition may contain only one type of specific dye, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention may contain a decomposition product of a specific dye.
- the composition of the invention contains a curable compound.
- the curable compound include polymerizable compounds and resins.
- the resin may be a non-polymerizable resin (a resin having no polymerizable group) or a polymerizable resin (a resin having a polymerizable group).
- polymerizable groups include ethylenically unsaturated bond-containing groups, cyclic ether groups, methylol groups, and alkoxymethyl groups.
- Examples of ethylenically unsaturated bond-containing groups include vinyl groups, vinylphenyl groups, (meth)allyl groups, (meth)acryloyl groups, (meth)acryloyloxy groups, (meth)acryloylamide groups, and the like. Allyl group, (meth)acryloyl group and (meth)acryloyloxy group are preferred, and (meth)acryloyloxy group is more preferred.
- Examples of the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
- the curable compound it is preferable to use one containing at least a resin. Further, when the composition of the present invention is used as a composition for photolithography, it is preferable to use a resin and a polymerizable monomer (monomer-type polymerizable compound) as the curable compound. It is more preferable to use a polymerizable monomer (monomer-type polymerizable compound) having an unsaturated bond-containing group.
- polymerizable compound examples include compounds having an ethylenically unsaturated bond-containing group, compounds having a cyclic ether group, compounds having a methylol group, and compounds having an alkoxymethyl group.
- a compound having an ethylenically unsaturated bond-containing group can be preferably used as a radically polymerizable compound.
- a compound having a cyclic ether group can also be preferably used as a cationic polymerizable compound.
- resin-type polymerizable compounds include resins containing repeating units having polymerizable groups.
- the molecular weight of the monomer type polymerizable compound is preferably less than 2000, more preferably 1500 or less.
- the lower limit of the molecular weight of the polymerizable monomer is preferably 100 or more, more preferably 200 or more.
- the weight average molecular weight (Mw) of the resin-type polymerizable compound is preferably 2,000 to 2,000,000.
- the upper limit of the weight average molecular weight is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit of the weight average molecular weight is preferably 3000 or more, more preferably 5000 or more.
- the compound having an ethylenically unsaturated bond-containing group as a polymerizable monomer is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound.
- Specific examples include paragraph numbers 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraph numbers 0254-0257 of JP-A-2008-292970, and JP-A-2013-253224.
- Examples of compounds having an ethylenically unsaturated bond-containing group include dipentaerythritol tri(meth)acrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), and dipentaerythritol tetra(meth)acrylate (commercially available).
- KAYARAD D-320 manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol penta(meth)acrylate commercially available KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol hexa(meth)acrylate ) Acrylate commercially available as KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.
- the (meth)acryloyl groups of these compounds are ethylene glycol and / Or a compound having a structure linked via a propylene glycol residue (for example, SR454 and SR499 commercially available from Sartomer).
- Examples of compounds having an ethylenically unsaturated bond-containing group include diglycerin EO (ethylene oxide)-modified (meth)acrylate (commercially available as M-460; manufactured by Toagosei), pentaerythritol tetraacrylate (Shin-Nakamura Chemical Industry ( Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Nippon Kayaku Co., Ltd.) Toagosei Co., Ltd.), NK Oligo UA-7200 (Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (Taisei Fine Chemical Co., Ltd.), Light acrylate POB-A0 (Kyoeish
- Examples of compounds having an ethylenically unsaturated bond-containing group include trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, and ethylene oxide isocyanurate. It is also preferable to use trifunctional (meth)acrylate compounds such as modified tri(meth)acrylate and pentaerythritol tri(meth)acrylate. Commercial products of trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306 and M-305.
- M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
- a compound having an ethylenically unsaturated bond-containing group may further have an acid group such as a carboxyl group, a sulfo group, or a phosphoric acid group.
- an acid group such as a carboxyl group, a sulfo group, or a phosphoric acid group.
- Commercially available products of such compounds include Aronix M-305, M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- a compound having a caprolactone structure can also be used as the compound having an ethylenically unsaturated bond-containing group.
- the descriptions in paragraphs 0042 to 0045 of JP-A-2013-253224 can be referred to, the contents of which are incorporated herein.
- Compounds having a caprolactone structure include, for example, DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available as a series from Nippon Kayaku Co., Ltd.
- a compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group can also be used as the compound having an ethylenically unsaturated bond-containing group.
- Such a compound is preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group and/or a propyleneoxy group, and is a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group. More preferably, it is a tri- to hexa-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups.
- Examples of commercially available products include SR-494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups and KAYARAD TPA-330, a trifunctional (meth)acrylate having three isobutyleneoxy groups, manufactured by Sartomer. mentioned.
- a polymerizable compound having a fluorene skeleton can also be used as the compound having an ethylenically unsaturated bond-containing group.
- Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- the compound having an ethylenically unsaturated bond-containing group it is also preferable to use a compound such as toluene that does not substantially contain environmentally regulated substances.
- Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- Examples of compounds having an ethylenically unsaturated bond-containing group include UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA- 306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 ( Kyoeisha Chemical Co., Ltd.) and the like are also preferably used.
- Compounds having a cyclic ether group include compounds having an epoxy group, compounds having an oxetanyl group, and the like, and compounds having an epoxy group are preferred.
- Compounds having an epoxy group include compounds having 1 to 100 epoxy groups in one molecule.
- the upper limit of the number of epoxy groups can be, for example, 10 or less, or 5 or less.
- the lower limit of the number of epoxy groups is preferably two or more.
- the compound having a cyclic ether group may be a low-molecular-weight compound (e.g., molecular weight less than 1000) or a high-molecular-weight compound (macromolecule) (e.g., molecular weight 1000 or more, weight-average molecular weight 1000 or more in the case of polymer).
- the weight average molecular weight of the cyclic ether group is preferably from 200 to 100,000, more preferably from 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
- methylol compounds include compounds in which a methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- compounds having an alkoxymethyl group include compounds in which an alkoxymethyl group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- Compounds having an alkoxymethyl or methylol group attached to the nitrogen atom include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluril, methylolated glycoluril, alkoxymethylated Urea and methylolated urea are preferred. Further, the compounds described in paragraphs 0134 to 0147 of JP-A-2004-295116 and paragraphs 0095-0126 of JP-A-2014-089408 can also be used.
- the composition of the present invention can use a resin as a curable compound. It is preferable to use a curable compound containing at least a resin.
- the resin is blended, for example, for dispersing a pigment or the like in the composition or for a binder.
- a resin that is mainly used to disperse a pigment or the like in a composition is also called a dispersant.
- such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
- a resin having a polymerizable group also corresponds to a polymerizable compound.
- the weight average molecular weight of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- resins include (meth)acrylic resins, epoxy resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, Polyamide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, vinyl acetate resins, polyvinyl alcohol resins, polyvinyl acetal resins, polyurethane resins, polyurea resins, and the like.
- norbornene resin is preferable from the viewpoint of improving heat resistance.
- Commercially available norbornene resins include, for example, the ARTON series manufactured by JSR Corporation (for example, ARTON F4520). Further, as the resin, the resin described in the examples of International Publication No.
- a resin having a fluorene skeleton can also be preferably used.
- the description of US Patent Application Publication No. 2017/0102610 can be referred to, the content of which is incorporated herein.
- a resin having an acid group As the resin.
- acid groups include carboxyl groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups. Only one kind of these acid groups may be used, or two or more kinds thereof may be used. Resins with acid groups can also be used as dispersants.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is preferably 50 mgKOH/g or more, more preferably 70 mgKOH/g or more.
- the upper limit is preferably 400 mgKOH/g or less, more preferably 200 mgKOH/g or less, still more preferably 150 mgKOH/g or less, and most preferably 120 mgKOH/g or less.
- a resin containing a repeating unit derived from a compound represented by the formula (ED1) and/or a compound represented by the formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferred to include
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP-A-2013-029760 can be referred to, the content of which is incorporated herein.
- the resin it is also preferable to use a resin having a polymerizable group.
- the polymerizable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, more preferably an ethylenically unsaturated bond-containing group.
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0-15.
- the number of carbon atoms in the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly 2 or 3.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- the resin preferably contains a resin as a dispersant.
- Dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is greater than the amount of basic groups.
- the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol % or more is preferable when the total amount of the acid group and the basic group is 100 mol %.
- the acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxyl group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10-105 mgKOH/g.
- a basic dispersant represents a resin in which the amount of basic groups is greater than the amount of acid groups.
- a resin containing more than 50 mol % of basic groups is preferable when the total amount of acid groups and basic groups is 100 mol %.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin for details of the graft resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
- the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of its main chain and side chains.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
- a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core.
- resins include, for example, dendrimers (including star polymers). Further, specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of repeating units having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70, of the total repeating units of the resin. More preferably, it is mol %.
- resins described in JP-A-2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, Polyethyleneimine having a polyester side chain described in International Publication No. 2016/104803, a block copolymer described in International Publication No. 2019/125940, a block polymer having an acrylamide structural unit described in JP-A-2020-066687 , a block polymer having an acrylamide structural unit described in JP-A-2020-066688 can also be used.
- Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie, SOLSPERSE series manufactured by Lubrizol Japan, Efka series manufactured by BASF, and Ajinomoto Fine-Techno Co., Ltd. Ajisper series manufactured by.
- the product described in paragraph number 0129 of JP-A-2012-137564 and the product described in paragraph number 0235 of JP-A-2017-194662 can also be used as a dispersant.
- the content of the curable compound is preferably 1 to 95% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, still more preferably 7% by mass or more, and particularly preferably 10% by mass or more.
- the upper limit is preferably 94% by mass or less, more preferably 90% by mass or less, still more preferably 85% by mass or less, and particularly preferably 80% by mass or less.
- the content of the polymerizable compound is preferably 1 to 85% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less.
- the content of the polymerizable monomer is preferably 1 to 50% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
- the content of the compound having an ethylenically unsaturated bond-containing group is 1 to 70 mass in the total solid content of the composition. % is preferred.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
- the content of the resin is preferably 1 to 85% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, still more preferably 7% by mass or more, and particularly preferably 10% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and particularly preferably 40% by mass or less.
- the content of the resin as a dispersant is preferably 0.1 to 40% by mass based on the total solid content of the composition.
- the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the content of the resin as a dispersant is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the above specific dye.
- the upper limit is preferably 80 parts by mass or less, more preferably 75 parts by mass or less.
- the lower limit is preferably 2.5 parts by mass or more, more preferably 5 parts by mass or more.
- composition of the present invention may contain only one type of curable compound, or may contain two or more types. When two or more curable compounds are included, the total amount thereof is preferably within the above range.
- the composition of the present invention can contain infrared absorbing agents (other infrared absorbing agents) other than the specific dyes described above. Furthermore, by containing other infrared absorbing agents, it is possible to form a film capable of shielding infrared rays in a wider wavelength range.
- Other infrared absorbers may be dyes or pigments (particles).
- infrared absorbers 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, and pyrromethene compounds. , azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
- pyrrolopyrrole compound compounds described in paragraph numbers 0016 to 0058 of JP-A-2009-263614, compounds described in paragraph numbers 0037-0052 of JP-A-2011-068731, WO 2015/166873 Compounds described in Paragraph Nos. 0010 to 0033 and the like.
- examples of the squarylium compound include compounds described in paragraph numbers 0044 to 0049 of JP-A-2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of WO 2016/181987.
- Examples of croconium compounds include compounds described in JP-A-2017-082029.
- As the iminium compound for example, compounds described in JP-A-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, International Publication No. 2018/043564 and the compounds described in paragraphs 0048 to 0063 of.
- phthalocyanine compound examples include compounds described in paragraph number 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, and paragraph numbers 0013 to 0029 of JP-A-2013-195480. compounds, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, and compounds described in International Publication No. 2020/071470. Examples of naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A-2012-077153. Dithiolene metal complexes include compounds described in Japanese Patent No. 5733804.
- metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- metal borides include lanthanum boride.
- Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.).
- a metal boride the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the infrared absorbing agent the squarylium compound described in JP-A-2017-197437, the squarylium compound described in JP-A-2017-025311, the squarylium compound described in WO 2016/154782, and the patent No. 5884953. No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No.
- the content of the other infrared absorbing agent is preferably 1 to 100 parts by mass, more preferably 3 to 60 parts by mass, and 5 to 40 parts by mass with respect to 100 parts by mass of the specific dye described above. is more preferred.
- the total content of the specific dye and other infrared absorbing agent described above is preferably 1% by mass or more, more preferably 3% by mass or more, based on the total solid content of the composition, and 5% by mass % or more is more preferable.
- the upper limit of the total content is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
- the specific dye itself may be a dye derivative (hereinafter also referred to as "derivative") as described above, but in addition to the above-described specific dye, it may further contain a dye derivative.
- Dye derivatives are used as dispersing aids. Examples of dye derivatives include compounds having a structure in which an acid group or a basic group is bonded to a dye skeleton.
- dye skeletons constituting dye derivatives include squarylium dye skeleton, pyrrolopyrrole dye skeleton, diketopyrrolopyrrole dye skeleton, quinacridone dye skeleton, anthraquinone dye skeleton, dianthraquinone dye skeleton, benzoisoindole dye skeleton, and thiazineindigo dye skeleton.
- a squarylium dye skeleton, a pyrrolopyrrole dye skeleton, a diketopyrrolopyrrole dye skeleton, a phthalocyanine dye skeleton, a quinacridone dye skeleton and a benzimidazolone dye skeleton are preferred, and a squarylium dye skeleton and a pyrrolopyrrole dye skeleton are more preferred.
- the acid group includes a carboxyl group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonamide group, an imidic acid group and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
- the carboxylic acid amide group a group represented by —NHCOR A1 is preferable.
- a group represented by —NHSO 2 R A2 is preferable.
- the imidic acid group is preferably a group represented by -SO 2 NHSO 2 R A3 , -CONHSO 2 R A4 , -CONHCOR A5 or -SO 2 NHCOR A6 , more preferably -SO 2 NHSO 2 R A3 .
- R A1 to R A6 each independently represent an alkyl group or an aryl group.
- the alkyl groups and aryl groups represented by R A1 to R A6 may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
- Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions. Specific examples and preferred examples of each group are the same as the basic group represented by X R1 in formula (R-100) described above.
- X a , X b , Ya , Y b , R 1 and At least one of R 2 may also include a dye having a group represented by formula (R-100) as a substituent.
- the dye derivative is more preferably a dye in which at least one of R 1 and R 2 in formula (1) has a group represented by formula (R-100) as a substituent. It is also preferable that the dye derivative is a compound in which at least one of R 1 and R 2 in formula (1) has a group represented by formulas (A-1) to (B-2) described below.
- the dye derivative include the compounds described in Examples described later.
- JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, JP-A-03-009961, JP-A-03-026767, JP-A-03-153780 Publications, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraph numbers 0086 to 0098 of International Publication No. 2011/024896, and compounds described in paragraph numbers 0063 to 0094 of International Publication No. 2012/102399, the contents of which are herein incorporated into.
- the content of the dye derivative is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the specific dye described above.
- the lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less. Only one dye derivative may be used, or two or more dye derivatives may be used. When two or more kinds are used, the total amount is preferably within the above range.
- the composition of the invention preferably contains a solvent.
- the solvent include water and organic solvents, and organic solvents are preferred.
- Organic solvents 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 cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used.
- organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (e.g., 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent with a ppt (parts per trillion) mass level may be used, and such an organic solvent is provided by, for example, Toyo Gosei Co., Ltd. (Chemical Daily, November 13, 2015).
- Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore size of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one isomer may be contained, or a plurality of isomers may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the composition is preferably 10-97% by mass.
- the lower limit is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, even more preferably 60% by mass or more, and 70% by mass. It is particularly preferable that it is above.
- the upper limit is preferably 96% by mass or less, more preferably 95% by mass or less.
- the composition may contain only one type of solvent, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the composition of the invention preferably further contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet region to the visible region are preferred.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl-substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, more preferably oxime compounds.
- hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. is mentioned.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (above company) and the like.
- ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by Irgacure 369E, Irgacure 379EG). made), etc.
- acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819 and Irgacure TPO (manufactured by BASF).
- Examples of oxime compounds include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, J. Am. C. S. Compounds described in Perkin II (1979, pp.1653-1660); C. S. Compounds described in Perkin II (1979, pp.156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232), compounds described in JP-A-2000-066385, Compounds described in JP-A-2004-534797, compounds described in JP-A-2017-019766, compounds described in Patent No.
- oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, and 2-ethoxycarbonyloxy and imino-1-phenylpropan-1-one.
- An oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include compounds described in JP-A-2014-137466, compounds described in Japanese Patent No. 6636081, and compounds described in Korean Patent Publication No. 10-2016-0109444. be done.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such oxime compounds include compounds described in WO2013/083505.
- An oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom include compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. and the compound (C-3) of.
- An oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraph numbers 0031 to 0047 of JP-A-2013-114249 and paragraph numbers 0008-0012 and 0070-0079 of JP-A-2014-137466; Compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 and ADEKA Arkles NCI-831 (manufactured by ADEKA Corporation) can be mentioned.
- An oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in WO 2015/036910.
- an oxime compound in which a substituent having a hydroxyl group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited to these.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high from the viewpoint of sensitivity, more preferably 1000 to 300000, further preferably 2000 to 300000, even more preferably 5000 to 200000. It is particularly preferred to have
- the molar extinction coefficient of a compound can be measured using known methods. For example, it is preferably measured at a concentration of 0.01 g/L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation becomes difficult over time, and the stability over time of the composition can be improved.
- Specific examples of bifunctional or trifunctional or higher photoradical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- the content of the photopolymerization initiator is preferably 0.1 to 40% by mass, more preferably 0.5 to 35% by mass, even more preferably 1 to 30% by mass, based on the total solid content of the composition.
- the composition may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- composition of the present invention contains a compound having a cyclic ether group, it preferably further contains a curing agent.
- curing agents include amine compounds, acid anhydride compounds, amide compounds, phenol compounds, polyvalent carboxylic acids, and thiol compounds.
- specific examples of curing agents include succinic acid, trimellitic acid, pyromellitic acid, N,N-dimethyl-4-aminopyridine, pentaerythritol tetrakis(3-mercaptopropionate) and the like.
- the content of the curing agent is preferably 0.01 to 20 parts by mass, more preferably 0.01 to 10 parts by mass, and 0.1 to 6.0 parts by mass with respect to 100 parts by mass of the compound having a cyclic ether group. is more preferred.
- the composition of the invention may contain chromatic colorants.
- a chromatic colorant means a colorant other than a white colorant and a black colorant.
- the chromatic colorant is preferably a colorant that absorbs in a wavelength range of 400 nm or more and less than 650 nm.
- the chromatic colorants include red colorants, green colorants, blue colorants, yellow colorants, purple colorants and orange colorants.
- a chromatic colorant may be a pigment or a dye.
- a pigment and a dye may be used in combination.
- the pigment may be either an inorganic pigment or an organic pigment.
- an inorganic pigment or a material in which a part of an organic-inorganic pigment is replaced with an organic chromophore can also be used. By replacing inorganic pigments or organic-inorganic pigments with organic chromophores, hue design can be facilitated.
- the average primary particle size of the pigment 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 average primary particle size of the pigment can be determined from the image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in the present invention is the arithmetic mean value of the primary particle sizes of 400 primary particles of the pigment.
- the primary particles of the pigment refer to independent particles without agglomeration.
- the chromatic colorant preferably contains a pigment.
- the content of the pigment in the chromatic colorant is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, and 90% by mass or more. is particularly preferred. Examples of pigments include those shown below.
- a halogenated zinc phthalocyanine pigment having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule.
- Specific examples include compounds described in International Publication No. 2015/118720.
- a phthalocyanine compound a phthalocyanine compound described in JP-A-2018-180023, a compound described in JP-A-2019-038958, a core-shell type dye described in JP-A-2020-076995, and the like can also be used.
- An aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue pigment.
- Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A-2012-247591 and paragraph number 0047 of JP-A-2011-157478.
- red pigments diketopyrrolopyrrole compounds in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, diketopyrrolopyrrole compounds described in paragraphs 0016 to 0022 of Japanese Patent No. 6248838, Diketopyrrolopyrrole compounds described in WO 2012/102399, diketopyrrolopyrrole compounds described in WO 2012/117965, naphthol azo compounds described in JP 2012-229344, Patent No. 6516119 Red pigment described in the publication, red pigment described in Patent No. 6525101, brominated diketopyrrolopyrrole compounds described in paragraph number 0229 of JP 2020-090632, Korean Patent No.
- 10-2019-0140741 Anthraquinone compounds described in publications, anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744, perylene compounds described in JP-A-2020-079396, and the like can also be used. Also, as a red pigment, a compound having a structure in which an aromatic ring group in which a group having an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton may be used. can.
- the pyrrolopyrrole-based pigment has a crystallite size of 140 ⁇ or less in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the eight planes of ( ⁇ 1 ⁇ 1 ⁇ 1) among the crystal lattice planes. It is also preferred to use one. Further, the physical properties of the pyrrolopyrrole pigment are preferably set as described in paragraphs 0028 to 0073 of JP-A-2020-097744.
- Dyes can also be used as chromatic colorants.
- the dye is not particularly limited, and known dyes can be used.
- pyrazole azo dyes anilinoazo 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, pyrromethene dyes, and the like.
- a pigment multimer can also be used as a chromatic colorant.
- the dye multimer is preferably a dye dissolved in a solvent and used. Further, the dye multimer may form particles. When the dye multimer is particles, it is usually used in a state of being dispersed in a solvent.
- the particulate dye multimer can be obtained, for example, by emulsion polymerization, and specific examples include the compounds and production methods described in JP-A-2015-214682.
- a dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less.
- a plurality of dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
- the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
- Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016/031442, etc. Compounds can also be used.
- the chromatic colorant the thiazole compound described in JP-A-2012-158649, the azo compound described in JP-A-2011-184493, the azo compound described in JP-A-2011-145540, published in Korea Triarylmethane dye polymer described in Patent No. 10-2020-0028160, xanthene compound described in JP-A-2020-117638, phthalocyanine compound described in WO2020/174991, JP-A-2020-160279
- An isoindoline compound or a salt thereof described in the publication can be used.
- the content of the chromatic colorant is preferably 1 to 50% by mass based on the total solid content of the composition of the present invention.
- the total amount thereof is preferably within the above range.
- the composition of the present invention can also contain a coloring material that transmits infrared rays and blocks visible light (hereinafter also referred to as a coloring material that blocks visible light).
- a composition containing a coloring material that blocks visible light is preferably used as a composition for forming an infrared transmission filter.
- the colorant that blocks visible light is preferably a colorant that absorbs light in the wavelength range from violet to red. Further, the coloring material that blocks visible light is preferably a coloring material that blocks light in the wavelength range of 450 to 650 nm. Further, the coloring material that blocks visible light is preferably a coloring material that transmits light with a wavelength of 900 to 1500 nm.
- the colorant that blocks visible light preferably satisfies at least one of the following requirements (A) and (B).
- B Contains an organic black colorant.
- organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred.
- bisbenzofuranone compounds include compounds described in Japanese Patent Application Publication No. 2010-534726, Japanese Patent Application Publication No. 2012-515233, Japanese Patent Application Publication No. 2012-515234, etc.
- perylene compounds include compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like.
- the azomethine compound include compounds described in JP-A-01-170601, JP-A-02-034664, and the like.
- examples of the combination of chromatic colorants include the following aspects (1) to (8).
- the content of the coloring material that blocks visible light is preferably 1 to 50 mass% of the total solid content of the composition.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, and particularly preferably 30% by mass or more.
- the composition of the invention preferably contains a surfactant.
- a surfactant various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants and silicone surfactants can be used.
- the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant.
- Surfactants include those described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
- JP 2014-041318 Paragraph Nos. 0060 to 0064 (corresponding International Publication No. 2014/017669 Paragraph Nos. 0060 to 0064) surfactants described in, JP 2011- Examples include surfactants described in paragraphs 0117 to 0132 of JP-A-132503 and surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
- Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143 and F-144.
- fluorine-based surfactant there is also an acrylic compound that has a molecular structure with a functional group containing a fluorine atom, and when heat is applied, the portion of the functional group containing the fluorine atom is cleaved and the fluorine atom volatilizes. It can be used preferably.
- fluorine-based surfactants include Megafac DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Megafac and DS-21.
- fluorosurfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorosurfactant.
- fluorosurfactants include fluorosurfactants described in JP-A-2016-216602, the contents of which are incorporated herein.
- a block polymer can also be used as the fluorosurfactant.
- a fluorosurfactant a repeating unit derived from a (meth)acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meta)
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compound is preferably 3000-50000, for example 14000. In the above compounds, % indicating the ratio of repeating units is mol %.
- a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in a side chain can also be used as the fluorine-based surfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K. Further, compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used as the fluorosurfactant.
- a fluorine-containing imide salt compound represented by formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a+ is an a-valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + .
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF company), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (Wako Pure
- Cationic surfactants include tetraalkylammonium salts, alkylamine salts, benzalkonium salts, alkylpyridium salts, imidazolium salts, and the like. Specific examples include dihydroxyethylstearylamine, 2-heptadecenyl-hydroxyethylimidazoline, lauryldimethylbenzylammonium chloride, cetylpyridinium chloride, stearamidomethylpyridinium chloride and the like.
- Anionic surfactants include dodecylbenzenesulfonic acid, sodium dodecylbenzenesulfonate, sodium lauryl sulfate, sodium alkyldiphenyletherdisulfonate, sodium alkylnaphthalenesulfonate, sodium dialkylsulfosuccinate, sodium stearate, potassium oleate, sodium dioctyl Sulfosuccinate, sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene alkylphenyl ether sulfate, sodium dialkyl sulfosuccinate, sodium oleate, sodium t-octylphenoxyethoxy polyethoxyethyl sulfate, etc. are mentioned.
- silicone surfactants examples include SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4440, and TSF-4300. , TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (Shin-Etsu Chemical Co., Ltd. Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie) and the like.
- a compound having the following structure can also be used as the silicone-based surfactant.
- the content of the surfactant is preferably 0.001 to 1% by mass, more preferably 0.001 to 0.5% by mass, and still more preferably 0.001 to 0.2% by mass of the total solid content of the composition.
- the composition may contain only one type of surfactant, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention may contain a polymerization inhibitor.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis(3-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.), and p-methoxyphenol is preferred.
- the content of the polymerization inhibitor is preferably 0.0001 to 5% by mass based on the total solid content of the composition.
- the composition may contain only one type of polymerization inhibitor, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the composition of the invention can contain a silane coupling agent.
- a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and capable of forming a siloxane bond by at least one of hydrolysis reaction and condensation reaction.
- Hydrolyzable groups include, for example, halogen atoms, alkoxy groups, acyloxy groups and the like, with alkoxy groups being preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group, isocyanate group, and phenyl group. with (meth)acryloyl groups and epoxy groups being preferred.
- the silane coupling agent includes compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703, and compounds described in paragraph numbers 0056-0066 of JP-A-2009-242604. incorporated into the specification.
- the content of the silane coupling agent is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass, based on the total solid content of the composition.
- the composition may contain only one type of silane coupling agent, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the composition of the invention may contain an ultraviolet absorber.
- UV absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and merocyanine dyes. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, paragraph numbers 0317-0317 of JP-A-2013-068814.
- UV absorbers include Tinuvin series and Uvinul series manufactured by BASF. Moreover, as a benzotriazole compound, the MYUA series made from Miyoshi oil and fats (Chemical Daily, February 1, 2016) is mentioned. Further, as the ultraviolet absorber, compounds described in paragraph numbers 0049 to 0059 of Japanese Patent No. 6268967 and paragraph numbers 0059 to 0076 of International Publication No. 2016/181987 can also be used.
- the content of the ultraviolet absorber is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, based on the total solid content of the composition.
- the composition may contain only one type of UV absorber, or may contain two or more types. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- the compositions of the invention may contain antioxidants.
- Antioxidants include phenol compounds, phosphite ester compounds, thioether compounds and the like. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
- the antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule.
- Phosphorus-based antioxidants can also be suitably used as antioxidants.
- a phosphorus antioxidant tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl ) oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like.
- antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Corporation) and the like.
- antioxidants include compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, and compounds described in WO 2017/164024. can also be used.
- the content of the antioxidant is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass, based on the total solid content of the composition.
- the composition may contain only one kind of antioxidant, or may contain two or more kinds. When two or more kinds are included, it is preferable that the total amount thereof is within the above range.
- composition of the present invention may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliary agents (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, etc.). agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). Properties such as film physical properties can be adjusted by appropriately containing these components. These components are, for example, described in JP 2012-003225, paragraph number 0183 and later (corresponding US Patent Application Publication No. 2013/0034812, paragraph number 0237), JP 2008-250074 paragraph The descriptions of numbers 0101 to 0104, 0107 to 0109, etc.
- the composition of the present invention may also contain latent antioxidants, if desired.
- the latent antioxidant is a compound in which the site functioning as an antioxidant is protected with a protective group, and is heated at 100 to 250°C, or heated at 80 to 200°C in the presence of an acid/base catalyst.
- a compound that functions as an antioxidant by removing the protective group by the reaction is exemplified.
- Examples of latent antioxidants include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Commercially available latent antioxidants include ADEKA Arkles GPA-5001 (manufactured by ADEKA Co., Ltd.).
- the storage container for the composition of the present invention is not particularly limited, and known storage containers can be used.
- a storage container a multi-layer bottle whose inner wall is composed of 6 types and 6 layers of resin and a bottle with a 7-layer structure of 6 types of resin are used for the purpose of suppressing the contamination of raw materials and compositions with impurities. It is also preferred to use Examples of such a container include the container described in JP-A-2015-123351.
- the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, enhancing the stability of the composition over time, and suppressing deterioration of components.
- compositions of the present invention can be prepared by mixing the aforementioned ingredients.
- the composition may be prepared by dissolving or dispersing all the components in a solvent at the same time, or if necessary, two or more solutions or dispersions in which each component is appropriately blended are prepared in advance. They may be prepared and mixed at the time of use (at the time of application) to prepare a composition.
- the preparation of the composition may include a process of dispersing the pigment.
- mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like.
- pulverizing the pigment in a sand mill (bead mill) it is preferable to use beads with a small diameter or to increase the filling rate of the beads so as to increase the pulverization efficiency.
- the process and dispersing machine for dispersing pigments are described in "Dispersion Technology Complete Works, Information Organization Co., Ltd., July 15, 2005” and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial Practical Application General Documents, Published by Management Development Center Publishing Department, October 10, 1978", the process and dispersing machine described in paragraph number 0022 of Japanese Patent Application Laid-Open No. 2015-157893 can be suitably used.
- the pigment may be finely divided in the salt milling process. Materials, equipment, processing conditions, etc. used in the salt milling process can be referred to, for example, Japanese Patent Application Laid-Open Nos. 2015-194521 and 2012-046629.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluorine resin such as polytetrafluoroethylene (PTFE), polyamide resin such as nylon (eg nylon-6, nylon-6,6), polyolefin resin such as polyethylene, polypropylene (PP) (high density, ultra high molecular weight (including polyolefin resin).
- PTFE polytetrafluoroethylene
- nylon eg nylon-6, nylon-6,6)
- polyolefin resin such as polyethylene
- PP polypropylene
- polypropylene including high density polypropylene
- nylon are preferred.
- the pore size of the filter is preferably 0.01-7.0 ⁇ m, more preferably 0.01-3.0 ⁇ m, and even more preferably 0.05-0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the pore size value of the filter reference can be made to the filter manufacturer's nominal value.
- Various filters provided by Nihon Pall Co., Ltd. (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as the filter. .
- fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
- Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Roki Techno.
- filters When using filters, different filters (eg, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed twice or more. Also, filters with different pore sizes within the range described above may be combined. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration with the second filter may be performed.
- filters eg, a first filter and a second filter, etc.
- the membrane of the invention is obtained from the composition of the invention described above.
- the film of the present invention can be preferably used as an optical filter.
- Applications of the optical filter are not particularly limited, but include infrared cut filters, infrared transmission filters, and the like.
- an infrared cut filter for example, an infrared cut filter on the light receiving side of the solid-state image sensor (for example, an infrared cut filter for a wafer level lens, etc.), an infrared cut filter on the back side of the solid-state image sensor (opposite to the light receiving side) , Infrared cut filters for ambient light sensors (for example, illuminance sensors that detect the illuminance and color tone of the environment in which the information terminal device is placed and adjust the color tone of the display, and color correction sensors that adjust the color tone) be done.
- the infrared transmission filter include a filter capable of blocking visible light and selectively transmitting infrared light having a specific wavelength or higher.
- the film of the present invention may have a pattern or may be a film without a pattern (flat film). Moreover, the film of the present invention may be used by laminating it on a support, or may be used by peeling the film of the present invention from the support. Examples of the support include semiconductor substrates such as silicon substrates and transparent substrates.
- a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the semiconductor substrate used as the support. Also, a black matrix that isolates each pixel may be formed on the semiconductor substrate. Further, if necessary, an undercoat layer may be provided on the semiconductor substrate for improving adhesion to the upper layer, preventing diffusion of substances, or flattening the surface of the substrate.
- CMOS complementary metal oxide semiconductor
- a transparent conductive film or the like
- an undercoat layer may be provided on the semiconductor substrate for improving adhesion to the upper layer, preventing diffusion of substances, or flattening the surface of the substrate.
- the transparent substrate used as the support is not particularly limited as long as it is composed of a material that can transmit at least visible light.
- Examples thereof include base materials made of materials such as glass and resin.
- resins include polyester resins such as polyethylene terephthalate and polybutylene terephthalate, polyolefin resins such as polyethylene, polypropylene, and ethylene vinyl acetate copolymer, acrylic resins such as norbornene resin, polyacrylate, and polymethyl methacrylate, urethane resins, and vinyl chloride resins. , fluororesin, polycarbonate resin, polyvinyl butyral resin, polyvinyl alcohol resin, and the like.
- glass examples include soda-lime glass, borosilicate glass, alkali-free glass, quartz glass, glass containing copper, and the like.
- Glass containing copper includes phosphate glass containing copper, fluorophosphate glass containing copper, and the like.
- a commercially available glass containing copper can also be used.
- Commercially available glass containing copper includes NF-50 (manufactured by AGC Techno Glass Co., Ltd.).
- the thickness of the film of the present invention can be adjusted as appropriate according to the purpose.
- the thickness of the film 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.
- the film of the present invention When the film of the present invention is used as an infrared cut filter, the film of the present invention preferably has a maximum absorption wavelength in the wavelength range of 650 to 1500 nm (preferably 660 to 1200 nm, more preferably 660 to 1000 nm). .
- the average transmittance of light with a wavelength of 420 to 550 nm is preferably 50% or more, more preferably 70% or more, still more preferably 80% or more, and particularly 85% or more. preferable.
- the transmittance in the entire wavelength range of 420 to 550 nm is preferably 50% or more, more preferably 70% or more, and even more preferably 80% or more.
- the film of the present invention preferably has a transmittance of 15% or less at at least one point in the wavelength range of 650 to 1500 nm (preferably 660 to 1200 nm, more preferably 660 to 1000 nm). The following is more preferable, and 5% or less is even more preferable.
- the film of the present invention preferably has an average absorbance of less than 0.030, more preferably less than 0.025 in the wavelength range of 420 to 550 nm when the absorbance at the maximum absorption wavelength is 1.
- the ability to block light around a wavelength of 400 nm can be evaluated by the transmittance (ultraviolet shielding property) at a wavelength of 390 nm, and the ultraviolet shielding property is preferably 5% or less.
- the film of the present invention preferably has, for example, any one of the following spectral characteristics (i1) to (i3).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 850 nm and transmit light in the wavelength range of 950 nm or more.
- the maximum transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1100 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light in the wavelength range of 1050 nm or more.
- the maximum transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1200 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 1050 nm and transmit light in the wavelength range of 1150 nm or more.
- the ability to block light around a wavelength of 400 nm can be evaluated by the transmittance (ultraviolet shielding property) at a wavelength of 390 nm, and the ultraviolet shielding property is preferably 5% or less.
- the film of the present invention can also be used in combination with a color filter containing a chromatic colorant.
- a color filter can be produced using a coloring composition containing a chromatic colorant.
- the color filter is preferably arranged on the optical path of the film of the present invention.
- the film of the present invention may be formed on a support other than the support on which the color filter is formed.
- Other members for example, a microlens, a planarization layer, etc. constituting the solid-state imaging device may be interposed between the film and the color filter.
- the film of the present invention can be used in various devices such as solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal oxide semiconductors), infrared sensors, and image display devices.
- solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal oxide semiconductors)
- infrared sensors and image display devices.
- the film of the present invention can be produced through the step of applying the composition of the present invention.
- Examples of the support include those mentioned above.
- a method for applying the composition a known method can be used. For example, drop method (drop cast); slit coating method; spray method; roll coating method; spin coating method (spin coating); methods described in publications); inkjet (e.g., on-demand method, piezo method, thermal method), discharge system printing such as nozzle jet, flexo printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, etc. Examples include various printing methods; transfer methods using molds and the like; nanoimprinting methods and the like.
- the application method for inkjet is not particularly limited.
- the composition layer formed by applying the composition may be dried (pre-baked).
- the pre-baking temperature is preferably 150° C. or lower, more preferably 120° C. or lower, and even more preferably 110° C. or lower.
- the lower limit can be, for example, 50° C. or higher, and can also be 80° C. or higher.
- the prebaking time is preferably 10 seconds to 3000 seconds, more preferably 40 seconds to 2500 seconds, and even more preferably 80 seconds to 220 seconds. Drying can be performed using a hot plate, an oven, or the like.
- the film manufacturing method may further include a step of forming a pattern.
- the pattern forming method include a pattern forming method using a photolithographic method and a pattern forming method using a dry etching method, and the pattern forming method using the photolithographic method is preferable.
- the step of forming a pattern may not be performed. The process of forming the pattern will be described in detail below.
- the pattern formation method by photolithography comprises a step of patternwise exposing the composition layer formed by coating the composition of the present invention (exposure step), and developing and removing the unexposed portion of the composition layer. and a step of forming a pattern (development step). If necessary, a step of baking the developed pattern (post-baking step) may be provided. Each step will be described below.
- the composition layer is exposed in a pattern.
- the composition layer can be exposed in a pattern by exposing through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
- Radiation (light) that can be used for exposure includes g-line, i-line, and the like.
- Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
- Light having a wavelength of 300 nm or less includes KrF rays (wavelength: 248 nm), ArF rays (wavelength: 193 nm), etc., and KrF rays (wavelength: 248 nm) are preferable.
- a long-wave light source of 300 nm or more can also be used.
- the light when exposing, the light may be continuously irradiated and exposed, or may be irradiated and exposed in pulses (pulse exposure).
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and rest in short-time (for example, millisecond level or less) cycles.
- the dose is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration at the time of exposure can be selected as appropriate, and in addition to exposure in the atmosphere, for example, in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (e.g., 15% by volume, 5% by volume, or substantially oxygen-free) or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W/m 2 to 100000 W/m 2 (eg, 5000 W/m 2 , 15000 W/m 2 or 35000 W/m 2 ). can be done.
- the oxygen concentration and exposure illuminance may be appropriately combined.
- the illuminance may be 10000 W/m 2 at an oxygen concentration of 10% by volume and 20000 W/m 2 at an oxygen concentration of 35% by volume.
- an unexposed portion of the composition layer after exposure is removed by development to form a pattern.
- the development and removal of the composition layer in the unexposed area can be carried out using a developer.
- the unexposed portion of the composition layer in the exposure step is eluted into the developer, leaving only the photocured portion on the support.
- the temperature of the developer is preferably 20 to 30° C., for example.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the step of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
- the developer includes an organic solvent, an alkaline developer, etc., and an alkaline developer is preferably used.
- an alkaline developer an alkaline aqueous solution (alkali developer) obtained by diluting an alkaline agent with pure water is preferable.
- alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate and sodium metasilicate.
- concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- a nonionic surfactant is preferable as the surfactant.
- the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it can be set, for example, in the range of 1.5 to 100 times.
- wash (rinse) with pure water after development. Rinsing is preferably carried out by supplying a rinse liquid to the composition layer after development while rotating the support on which the composition layer after development is formed. It is also preferable to move the nozzle for discharging the rinsing liquid from the central portion of the support to the peripheral portion of the support.
- the moving speed of the nozzle may be gradually decreased.
- in-plane variations in rinsing can be suppressed.
- a similar effect can be obtained by gradually decreasing the rotation speed of the support while moving the nozzle from the center of the support to the periphery.
- Additional exposure processing and post-baking are post-development curing treatments for complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 240.degree. C., more preferably 200 to 240.degree.
- Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulating dryer), or a high-frequency heater so that the developed film satisfies the above conditions. .
- the light used for exposure preferably has a wavelength of 400 nm or less.
- the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by a dry etching method includes curing the composition layer formed by coating the composition on a support to form a cured product layer, and then forming a photoresist layer patterned on the cured product layer. is formed, and then dry etching is performed on the cured product layer using an etching gas using the patterned photoresist layer as a mask. In forming the photoresist layer, pre-baking is preferably performed.
- description in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and the contents thereof are incorporated into this specification.
- optical filter of the present invention has the film of the present invention as described above.
- Types of optical filters include infrared cut filters and infrared transmission filters.
- the optical filter of the present invention may further have a layer containing copper, a dielectric multilayer film, an ultraviolet absorbing layer, etc., in addition to the film of the present invention described above.
- the ultraviolet absorbing layer include the absorbing layers described in paragraphs 0040 to 0070 and 0119 to 0145 of International Publication No. 2015/099060.
- Dielectric multilayer films include dielectric multilayer films described in paragraphs 0255 to 0259 of JP-A-2014-041318.
- the layer containing copper a glass substrate made of glass containing copper (copper-containing glass substrate) or a layer containing a copper complex (copper complex-containing layer) can be used.
- Copper-containing glass substrates include copper-containing phosphate glass, copper-containing fluorophosphate glass, and the like.
- Commercially available copper-containing glasses include NF-50 (manufactured by AGC Techno Glass Co., Ltd.), BG-60, BG-61 (manufactured by Schott), CD5000 (manufactured by HOYA Corporation), and the like.
- the solid-state imaging device of the present invention includes the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device. For example, the following configuration can be mentioned.
- a plurality of photodiodes constituting the light receiving area of the solid-state imaging device and transfer electrodes made of polysilicon or the like are provided on the support, and the photodiodes and the transfer electrodes are formed of tungsten or the like with openings only for the light receiving portions of the photodiodes.
- a device protective film formed of silicon nitride or the like is formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion, and the present invention is formed on the device protective film.
- the color filter may have a structure in which a film forming each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the partition in this case preferably has a lower refractive index than each pixel. Examples of imaging devices having such a structure include devices described in JP-A-2012-227478 and JP-A-2014-179577.
- the image display device of the invention comprises the film of the invention.
- image display devices include liquid crystal display devices and organic electroluminescence (organic EL) display devices.
- organic EL organic electroluminescence
- For the definition and details of the image display device see, for example, “Electronic Display Device (written by Akio Sasaki, Industrial Research Institute, 1990)", “Display Device (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd., 1989). issued)”, etc.
- Liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied.
- the image display device may have a white organic EL element.
- a white organic EL device preferably has a tandem structure. Regarding the tandem structure of organic EL elements, see Japanese Patent Application Laid-Open No. 2003-045676, supervised by Akiyoshi Mikami, "Forefront of Organic EL Technology Development -High Brightness, High Precision, Long Life, Know-how Collection-", Technical Information Association, 326-328, 2008, and others.
- the spectrum of white light emitted by the organic EL element preferably has strong maximum emission peaks in the blue region (430-485 nm), the green region (530-580 nm) and the yellow region (580-620 nm). In addition to these emission peaks, those having a maximum emission peak in the red region (650 to 700 nm) are more preferred.
- the infrared sensor of the invention comprises the membrane of the invention as described above.
- the configuration of the infrared sensor is not particularly limited as long as it functions as an infrared sensor. An embodiment of the infrared sensor of the present invention will be described below with reference to the drawings.
- reference numeral 110 is a solid-state imaging device.
- An infrared cut filter 111 and an infrared transmission filter 114 are arranged on the imaging area of the solid-state imaging device 110 .
- a color filter 112 is arranged on the infrared cut filter 111 .
- a microlens 115 is arranged on the incident light h ⁇ side of the color filter 112 and the infrared transmission filter 114 .
- a planarization layer 116 is formed to cover the microlens 115 .
- the infrared cut filter 111 can be formed using the composition of the present invention.
- the color filter 112 is a color filter formed with pixels that transmit and absorb light of a specific wavelength in the visible region, and is not particularly limited, and conventionally known color filters for forming pixels can be used. For example, a color filter having red (R), green (G), and blue (B) pixels is used. For example, paragraph numbers 0214 to 0263 of JP-A-2014-043556 can be referred to, and the contents thereof are incorporated herein.
- the characteristics of the infrared transmission filter 114 are selected according to the emission wavelength of the infrared LED used. Infrared transmission filter 114 can be formed using the composition of the present invention.
- an infrared cut filter (another infrared cut filter) different from the infrared cut filter 111 may be further arranged on the planarization layer 116 .
- Other infrared cut filters include those having copper-containing layers and/or dielectric multilayers. These details are given above.
- a dual bandpass filter may be used as another infrared cut filter.
- a camera module of the present invention includes a solid-state imaging device and the film of the present invention described above.
- the camera module further includes a lens and circuitry for processing the images obtained from the solid-state image sensor.
- the solid-state imaging device used in the camera module may be the solid-state imaging device according to the present disclosure or a known solid-state imaging device.
- the lens used in the camera module and the circuit for processing the image obtained from the solid-state imaging device known ones can be used.
- the camera modules described in JP-A-2016-006476 and JP-A-2014-197190 can be considered, the contents of which are incorporated herein.
- the compound of the present invention is a compound represented by Formula (1).
- Y a and Y b each independently represent a hydrogen atom or a substituent
- R 1 and R 2 each independently represent an optionally substituted aliphatic hydrocarbon group.
- X a , X b , Y a , Y b , R 1 and R 2 of formula (1) are X a of formula (1) shown as dyes (specific dyes) represented by formula (1) described above. , X b , Y a , Y b , R 1 and R 2 .
- the maximum absorption wavelength of the compound of the present invention preferably exists at a wavelength of 650 nm or more, more preferably in the wavelength range of 650 to 1500 nm, still more preferably in the wavelength range of 660 to 1200 nm. It is particularly preferred to be present in the range of -1000 nm.
- the compound of the present invention has an average absorbance value in the wavelength range of 420 to 550 nm when the absorbance value at the wavelength ( ⁇ max) showing the largest absorbance value in the wavelength range of 400 nm to 1200 nm is 1. It is preferably less than 0.010, more preferably less than 0.005.
- the compound of the present invention can be preferably used as an infrared absorbing agent.
- the compounds of the invention can also be used as dispersing aids.
- the infrared absorbent of the present invention contains a compound represented by formula (1).
- the infrared absorber may contain only one compound represented by Formula (1), or may contain two or more thereof.
- the infrared absorbing agent of the present invention may contain a decomposition product of the compound represented by formula (1).
- Me represents a methyl group
- Et represents an ethyl group
- Ph represents a phenyl group
- Ac represents an acetyl group.
- the resulting reaction solution was cooled to 10°C or less, and 90 mL of hexane was added dropwise while maintaining the internal temperature of the reaction solution at 0°C to 10°C, followed by 30 minutes while maintaining the internal temperature of the reaction solution at 0°C to 10°C. Stirred. Then, this reaction liquid was filtered and spray-washed with 15 mL of hexane to obtain a solid. The resulting solid was added to a three-necked flask, 75 mL of saturated aqueous sodium bicarbonate was added, and the mixture was stirred for 5 minutes, filtered, and spray-washed with 15 mL of saturated aqueous sodium bicarbonate to obtain a solid.
- Dye PPB-A-45 was synthesized according to the following scheme.
- reaction solution A was added dropwise over 30 minutes while maintaining the internal temperature of the reaction solution in the range of 90 to 95° C., and 2.16 g of phenyl dichlorophosphate was added. Stirred at 90-95° C. for 15 minutes.
- the resulting reaction solution is cooled to 10°C or less, and 44.2 g of hexane is added dropwise while maintaining the internal temperature of the reaction solution at 0°C to 10°C. Stir for 30 minutes. Then, this reaction liquid was filtered and spray-washed with 10 g of hexane to obtain a solid.
- a dye solution was prepared by dissolving the dye described in the table below in the solvent described in the table below.
- the absorbance of the obtained dye solution for light with a wavelength of 400 to 1200 nm was measured using a spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corporation).
- the wavelength ( ⁇ max) at which the absorbance is the largest is measured, and the absorbance value at ⁇ max is set to 1, and the average absorbance value in the wavelength range of 420 to 550 nm is calculated.
- the visible transparency was evaluated according to the following criteria. It can be said that the smaller the average absorbance, the higher the visible transparency.
- the average absorbance at a wavelength of 420 to 550 nm is less than 0.005
- B The average absorbance at a wavelength of 420 to 550 nm is 0.005 or more and less than 0.010
- C The average absorbance at a wavelength of 420 to 550 nm is 0.010 or more
- Dye PPB-A-1 to Dye PPB-A-45 and Dye PPB-C-1 to Dye PPB-C-3 are superior in visible transparency to Dye PPB-D-1 and Dye PPB-D-2. rice field. Details of each dye are as follows.
- PPB-A-1 to PPB-A-45 compounds having the following structures (dyes (specific dyes) represented by formula (1))
- PPB-C-1 to PPB-C-3 compounds having the following structures (dyes (specific dyes) represented by formula (1))
- PPB-D-1, PPB-D-2, PPB-E-1 Compounds with the following structures (comparative dyes)
- PPB-A-1 to PPB-A-45 compounds having the above structures (dyes (specific dyes) represented by formula (1))
- PPB-B-1 to PPB-B-16 compounds having the following structures (PPB-B-1 to PPB-13, PPB-B-15 and PPB-B-16 are represented by formula (1) It is a dye (specific dye), and PPB-B-14 is a compound different from the dye (specific dye) represented by formula (1).)
- (dispersant) D-1 A resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain represents the number of repeating units. Weight average molecular weight 38900, acid value 99.1 mgKOH/g) was added to propylene.
- D-2 resin with the following structure (numerical values attached to the main chain are molar ratios and the numerical value attached to the side chain represents the number of repeating units.Weight average molecular weight 21000, acid value 36.0 mgKOH/g, amine value 47.0 mgKOH/g)
- Propylene glycol monomethyl ether acetate: propylene glycol monomethyl ether A mixed solution of 9:1 (mass ratio) with a solid concentration of 20% by mass
- a dye solution was prepared by mixing 8.02 parts by weight of the pigment (dye) shown in the table below and 91.98 parts by weight of the solvent shown in the table below.
- PPB-C-1 to PPB-C-3 compounds having the above structures (dyes (specific dyes) represented by formula (1))
- PPB-E-1 compound with the structure described above (comparative dye)
- composition ⁇ Production of composition> Each material was mixed in the ratios of formulations 1 to 6 shown below and filtered through a nylon filter (manufactured by Nippon Pall Co., Ltd.) with a pore size of 0.45 ⁇ m to produce each composition.
- E-1 Copolymer resin of benzyl methacrylate, methacrylic acid and 2-hydroxyethyl methacrylate (weight average molecular weight 14000, acid value 77 mgKOH/g, alkali-soluble resin)
- E-2 ARTON F4520 (manufactured by JSR Corporation, cyclic polyolefin resin)
- E-3 Resin having the following structure (weight-average molecular weight: 40,000, acid value: 100 mgKOH/g, the numerical value attached to the main chain represents the mass ratio of repeating units. Alkali-soluble resin)
- M-1 Aronix M-305 (manufactured by Toagosei Co., Ltd., a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate. The content of pentaerythritol triacrylate is 55% by mass to 63% by mass.)
- M-2 KAYARAD RP-1040 (manufactured by Nippon Kayaku Co., Ltd., ethylene oxide-modified pentaerythritol tetraacrylate)
- M-3 Aronix M-510 (manufactured by Toagosei Co., Ltd., polybasic acid-modified acrylic oligomer)
- C-1 Irgacure OXE01 (manufactured by BASF, oxime ester initiator)
- C-2 Irgacure OXE02 (manufactured by BASF, oxime ester initiator)
- C-3 Omnirad 907 (manufactured by IGM Resins B.V., ⁇ -aminoalkylphenone initiator)
- F-1 Glycidyl methacrylate backbone random polymer (manufactured by NOF Corporation, Marproof G-0150M, weight average molecular weight 10000)
- F-2 EPICLON N-695 (manufactured by DIC Corporation, novolak type epoxy resin)
- F-3 JER1031S (manufactured by Mitsubishi Chemical Corporation, polyfunctional epoxy resin)
- F-4 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol)
- G-1 trimellitic acid
- G-2 pyromellitic anhydride
- G-3 N,N-dimethyl-4-aminopyridine
- G-4 pentaerythritol tetrakis (3-mercaptopropionate)
- H-1 Megafac RS-72-K (manufactured by DIC Corporation, fluorine-based surfactant)
- H-2 A compound having the following structure (weight average molecular weight: 14,000, % indicating the ratio of repeating units is mol%)
- H-3 KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., carbinol-modified polydimethylsiloxane at both ends, hydroxyl value 62 mgKOH/g)
- U-1 Uvinul 3050 (manufactured by BASF, compound with the following structure)
- U-2 Tinuvin477 (manufactured by BASF, hydroxyphenyltriazine-based UV absorber)
- U-3 Tinuvin326 (manufactured by BASF, compound with the following structure)
- the absorbance of the obtained film to light with a wavelength of 400 nm to 1200 nm was measured using a spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corporation). In the wavelength range of 400 nm to 1200 nm, the wavelength ( ⁇ max) at which the absorbance is the largest is measured, and the absorbance value at ⁇ max is set to 1, and the average absorbance value in the wavelength range of 420 to 550 nm is calculated. Then, the visible transparency was evaluated according to the following criteria.
- the average absorbance at a wavelength of 420 to 550 nm is less than 0.025
- B The average absorbance at a wavelength of 420 to 550 nm is 0.025 or more and less than 0.050
- C The average absorbance at a wavelength of 420 to 550 nm is 0.050 or more
- the obtained film was placed in a thermostat at 150° C. and heat-treated for 1000 hours.
- the absorbance of the film after the heat treatment was measured with a spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corporation) for light with a wavelength of 400 to 1200 nm.
- the wavelength ( ⁇ max) at which the absorbance is the largest is measured, and the absorbance value at ⁇ max is set to 1, and the average absorbance value in the wavelength range of 420 to 550 nm is calculated.
- the visible transparency after heating was evaluated according to the following criteria.
- the average absorbance at a wavelength of 420 to 550 nm is less than 0.025
- B The average absorbance at a wavelength of 420 to 550 nm is 0.025 or more and less than 0.050
- C The average absorbance at a wavelength of 420 to 550 nm is 0.050 or more
- ⁇ Evaluation of transmittance change after heating> The transmittance of light having a wavelength of 400 to 1200 nm was measured for the obtained film using a spectrophotometer U-4100 (manufactured by Hitachi High-Technologies Corporation). Then, the film was placed in a thermostat at 150° C. and heat-treated for 1000 hours. For the film after heat treatment, the transmittance of light with a wavelength of 400 to 1200 nm is similarly measured, and the transmittance change ( ⁇ T) at each wavelength in the wavelength range of 400 to 1200 nm before and after the heat treatment is measured. The maximum value ( ⁇ Tmax) of transmittance change was obtained, and the maximum value ( ⁇ Tmax) of transmittance change was evaluated according to the following criteria.
- ⁇ Tmax means the largest value of transmittance change ⁇ T at each wavelength of 400 to 1200 nm calculated above.
- the compositions of the examples were able to form films with low fluorescence quantum yields and excellent visible transparency.
- the films obtained using the compositions of Examples were excellent in visible transparency even after heating, and had a small change in transmittance before and after heating.
- the films obtained using the compositions of Examples 701 to 751 all had a transmittance of 5% at a wavelength of 390 nm and were excellent in ultraviolet shielding properties.
- Examples 1-19, 21, 25, 26, 27, 29-51, 401-419, 421, 425, 426, 427, 429-451, 701-719, 721, 725, 726, 727, 729- 751 was also excellent in light resistance.
- M represents Li, Na, K, Rb, Cs or a structure represented by Formula (C) or Formula (D).
- R z 1 to R z 4 each independently represent a hydrogen atom, an optionally substituted branched or linear alkyl group, or an optionally substituted aryl group. . However, R z 1 to R z 4 may be linked to each other to form a ring.
- R z 5 to R z 9 each independently represent a substituent, R z 5 and R z 6 , R z 6 and R z 7 , R z 7 and R z 8 , R z 8 and R z 9 may be linked to each other to form a ring.
- An optical filter, solid-state imaging device, image display device, infrared sensor or camera module having excellent performance can be obtained by using the film of the example in an optical filter, a solid-state imaging device, an image display device, an infrared sensor or a camera module. .
- Example 1001 to 1051 Composition IR prepared above was applied onto a glass substrate by spin coating so that the film thickness after post-baking was 7.0 ⁇ m, and then heated (pre-baked) at 100° C. for 10 minutes using a hot plate. Then, it was cured by heating at 200° C. for 8 minutes to obtain a film with a thickness of 7.0 ⁇ m.
- the compositions of Examples 401 to 451 were applied as the composition for the second layer on the glass substrate so that the film thickness of the second layer after post-baking was 1.0 ⁇ m. Then, using a hot plate, heat (pre-bake) at 100 ° C. for 10 minutes, then heat at 200 ° C. for 8 minutes to perform curing treatment, forming a second layer film with a thickness of 1.0 ⁇ m.
- a laminated film with a thickness of 8.0 ⁇ m was obtained.
- the laminated films of Examples 1001 to 1051 were observed under a bright field of 200x using an optical microscope for the presence of deposition of foreign matter, no deposition of foreign matter was observed in any of the films. Moreover, the laminated films of Examples 1001 to 1051 all had a light transmittance of less than 5% at a wavelength of 390 nm, and were excellent in ultraviolet shielding properties.
- An optical filter, solid-state imaging device, image display device, infrared sensor, or camera module having excellent performance can be obtained by using the laminated film of the example in an optical filter, solid-state imaging device, image display device, infrared sensor, or camera module. can.
- 110 solid-state imaging device
- 111 infrared cut filter
- 112 color filter
- 114 infrared transmission filter
- 115 microlens
- 116 flattening layer
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Abstract
Description
<1> 式(1)で表される色素と、硬化性化合物と、を含む組成物;
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す;
Ra11~Ra29はそれぞれ独立して、水素原子または置換基を表し、
XcおよびXdはそれぞれ独立して、S、OまたはNRX2を表し、RX2は水素原子または置換基を表し、
A1は、置換基を有していてもよい芳香族炭化水素環、芳香族複素環またはこれらの縮合環を表す。
<2> 上記式(1)のXaおよびXbはそれぞれ独立して、式(X-1-1)~(X-1-3)のいずれかで表される基である、<1>に記載の組成物;
Ra51~Ra63は、それぞれ独立して水素原子または置換基を表し、
式(X-1-1)のRa51~Ra54のうち隣接する2つの基同士は結合して環を形成していてもよく、
式(X-1-2)のRa55~Ra58のうち隣接する2つの基同士は結合して環を形成していてもよく、
式(X-1-3)のRa60~Ra63のうち隣接する2つの基同士は結合して環を形成していてもよい。
<3> 上記式(1)のYaおよびYbはそれぞれ独立して、-BRY1RY2を表し、RY1およびRY2は、それぞれ独立して水素原子、ハロゲン原子、アルキル基、アルケニル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基またはヘテロアリールオキシ基を表し、RY1およびRY2は互いに結合して環を形成していてもよい、
<1>または<2>に記載の組成物。
<4> 上記式(1)のR1およびR2の少なくとも一方が、置換基を有してもよい炭素数9以下のアルキル基である、<1>~<3>のいずれか1つに記載の組成物。
<5> 上記式(1)のR1およびR2の少なくとも一方が、式(R-1)で表される基である、<1>~<3>のいずれか1つに記載の組成物;
<6> 上記式(1)で表される色素が極大吸収波長を波長650nm以上に有する、<1>~<5>のいずれか1つに記載の組成物。
<7> <1>~<6>のいずれか1つに記載の組成物を用いて得られる膜。
<8> <7>に記載の膜を含む光学フィルタ。
<9> <7>に記載の膜を含む固体撮像素子。
<10> <7>に記載の膜を含む画像表示装置。
<11> <7>に記載の膜を含む赤外線センサ。
<12> <7>に記載の膜を含むカメラモジュール。
<13> 式(1)で表される化合物;
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す;
Ra11~Ra29はそれぞれ独立して、水素原子または置換基を表し、
XcおよびXdはそれぞれ独立して、S、OまたはNRX2を表し、RX2は水素原子または置換基を表し、
A1は、置換基を有していてもよい芳香族炭化水素環、芳香族複素環またはこれらの縮合環を表す。
<14> <13>に記載の化合物を含む赤外線吸収剤。
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、重量平均分子量および数平均分子量は、ゲルパーミエーションクロマトグラフィ(GPC)測定でのポリスチレン換算値として定義される。
本明細書において、化学式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表す。
本明細書において、赤外線とは、波長700~2500nmの光(電磁波)をいう。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本発明の組成物は、式(1)で表される色素と、硬化性化合物と、を含むことを特徴とする。
本発明の組成物は、式(1)で表される色素(以下、特定色素ともいう)を含む。
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す;
Ra11~Ra29はそれぞれ独立して、水素原子または置換基を表し、
XcおよびXdはそれぞれ独立して、S、OまたはNRX2を表し、RX2は水素原子または置換基を表し、
A1は、置換基を有していてもよい芳香族炭化水素環、芳香族複素環またはこれらの縮合環を表す。
ヘテロアリール基は、単環であってもよいが、縮合環であることが好ましい。ヘテロアリール基のヘテロアリール環を構成するヘテロ原子の数は1~3が好ましい。ヘテロアリール環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。ヘテロアリール環を構成する炭素原子の数は3~30が好ましく、3~18がより好ましく、3~12が更に好ましい。ヘテロアリール環は、5員環または6員環が好ましい。
アリール基およびヘテロアリール基は、置換基を有していてもよく、無置換であってもよい。置換基としては、後述する置換基Tで挙げた基および後述する式(R-100)で表される基が挙げられ、ハロゲン原子、アルキル基、アルコキシ基、アルキルチオ基、アシル基、アルコキシカルボニル基、アシルオキシ基、アリール基、アリールオキシ基、ヒドロキシ基、カルボキシル基、カルボン酸アミド基、スルホンアミド基、イミド基、スルホ基または式(R-100)で表される基であることが好ましく、ハロゲン原子、アルキル基、アルコキシ基、アシル基、アリール基、アリールオキシ基、ヒドロキシ基、カルボキシル基、スルホンアミド基、イミド基またはスルホ基であることがより好ましい。
Ra51~Ra63は、それぞれ独立して水素原子または置換基を表し、
式(X-1-1)のRa51~Ra54のうち隣接する2つの基同士は結合して環を形成していてもよく、
式(X-1-2)のRa55~Ra58のうち隣接する2つの基同士は結合して環を形成していてもよく、
式(X-1-3)のRa60~Ra63のうち隣接する2つの基同士は結合して環を形成していてもよい。
Ra51~Ra58、Ra60~Ra63が表す置換基は、ハロゲン原子、アルキル基、アルコキシ基、アルキルチオ基、アシル基、アルコキシカルボニル基、アシルオキシ基、アリール基、アリールオキシ基、ヒドロキシ基、カルボキシル基、カルボン酸アミド基、スルホンアミド基、イミド基、スルホ基または式(R-100)で表される基であることが好ましく、ハロゲン原子、アルキル基、アルコキシ基、アシル基、アリール基、アリールオキシ基、ヒドロキシ基、カルボキシル基、スルホンアミド基、イミド基またはスルホ基であることがより好ましい。
Ra59が表す置換基は、アルキル基、アルコキシ基、アシル基、アルール基またはアリールオキシ基であることが好ましく、アルキル基であることがより好ましい。アルキル基の炭素数は、1~10が好ましく、1~5がより好ましく、1~3が更に好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよいが、直鎖または分岐であることが好ましく、直鎖であることがより好ましい。
Ra59は水素原子またはメチル基であることが好ましく、メチル基であることがより好ましい。
アルキル基の炭素数は、1~30が好ましい。下限は、3以上が好ましい。特定色素が顔料の場合には、アルキル基の炭素数の上限は15以下が好ましく、10以下がより好ましく、7以下が更に好ましい。特定色素が染料の場合には、アルキル基の炭素数の上限は25以下が好ましく、19以下がより好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよい。
アルケニル基の炭素数は、2~30が好ましい。下限は、3以上が好ましい。特定色素が顔料の場合には、アルケニル基の炭素数の上限は15以下が好ましく、10以下がより好ましく、7以下が更に好ましい。特定色素が染料の場合には、アルケニル基の炭素数の上限は25以下が好ましく、19以下がより好ましい。アルケニル基は、直鎖、分岐、環状のいずれでもよい。
アルキニル基の炭素数は、2~30が好ましい。下限は、3以上が好ましい。特定色素が顔料の場合には、アルキニル基の炭素数の上限は15以下が好ましく、10以下がより好ましく、7以下が更に好ましい。特定色素が染料の場合には、アルキニル基の炭素数の上限は25以下が好ましく、19以下がより好ましい。アルキニル基は、直鎖、分岐、環状のいずれでもよい。
アルキル基、アルケニル基およびアルキニル基は、置換基を有していてもよく、無置換であってもよい。置換基としては後述する置換基Tで挙げた基および後述する式(R-100)で表される基が挙げられ、ハロゲン原子、アルコキシ基、アルキルチオ基、ウレイド基、アシル基、アルコキシカルボニル基、アシルオキシ基、スルファモイル基、アリール基、アリールオキシ基、ヒドロキシ基、カルボキシル基、カルボン酸アミド基、スルホンアミド基、イミド基、スルホ基または式(R-100)で表される基であることが好ましい。
RY1およびRY2が表すアルキル基およびアルコキシ基の炭素数は、1~40が好ましく、1~30がより好ましく、1~20が更に好ましい。アルキル基およびアルコキシ基は、直鎖、分岐、環状のいずれでもよいが、直鎖または分岐が好ましい。アルキル基およびアルコキシ基は、置換基を有していてもよく、無置換であってもよい。置換基としては、アリール基、ヘテロアリール基、ハロゲン原子などが挙げられる。
RY1およびRY2が表すアルケニル基の炭素数は、2~40が好ましく、2~30がより好ましく、2~20が更に好ましい。アルケニル基は、置換基を有していてもよく、無置換であってもよい。置換基としては、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、ハロゲン原子などが挙げられる。
RY1およびRY2が表すアリール基およびアリールオキシ基の炭素数は、6~20が好ましく、6~12がより好ましい。アリール基およびアリールオキシ基は、置換基を有していてもよく、無置換であってもよい。置換基としては、アルキル基、アルコキシ基、ハロゲン原子などが挙げられる。
RY1およびRY2が表すヘテロアリール基およびヘテロアリールオキシ基は、単環であってもよく、縮合環であってもよい。ヘテロアリール基およびヘテロアリールオキシ基のヘテロアリール環を構成するヘテロ原子の数は1~3が好ましい。ヘテロアリール環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。ヘテロアリール環を構成する炭素原子の数は3~30が好ましく、3~18がより好ましく、3~12が更に好ましい。ヘテロアリール環は、5員環または6員環が好ましい。ヘテロアリール基およびヘテロアリールオキシ基は、置換基を有していてもよく、無置換であってもよい。置換基としては、アルキル基、アルコキシ基、ハロゲン原子などが挙げられる。
置換基Tとして、次の基が挙げられる。ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、ヘテロアリール基(好ましくは炭素数1~30のヘテロアリール基)、アミノ基(好ましくは炭素数0~30のアミノ基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基(好ましくは炭素数1~30のヘテロアリールオキシ基)、アシル基(好ましくは炭素数2~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロアリールオキシカルボニル基(好ましくは炭素数2~30のヘテロアリールオキシカルボニル基)、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アミノカルボニルアミノ基(好ましくは炭素数2~30のアミノカルボニルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、スルファモイルアミノ基(好ましくは炭素数0~30のスルファモイルアミノ基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30のヘテロアリールチオ基)、アルキルスルホニル基(好ましくは炭素数1~30のアルキルスルホニル基)、アルキルスルホニルアミノ基(好ましくは炭素数1~30のアルキルスルホニルアミノ基)、アリールスルホニル基(好ましくは炭素数6~30のアリールスルホニル基)、アリールスルホニルアミノ基(好ましくは炭素数6~30のアリールスルホニルアミノ基)、ヘテロアリールスルホニル基(好ましくは炭素数1~30のヘテロアリールスルホニル基)、ヘテロアリールスルホニルアミノ基(好ましくは炭素数1~30のヘテロアリールスルホニルアミノ基)、アルキルスルフィニル基(好ましくは炭素数1~30のアルキルスルフィニル基)、アリールスルフィニル基(好ましくは炭素数6~30のアリールスルフィニル基)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30のヘテロアリールスルフィニル基)、ウレイド基(好ましくは炭素数1~30のウレイド基)、ヒドロキシ基、ニトロ基、カルボキシル基、スルホ基、リン酸基、カルボン酸アミド基、スルホン酸アミド基、イミド基、ホスフィノ基、メルカプト基、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、アリールアゾ基、ヘテロアリールアゾ基、ホスフィニル基、ホスフィニルオキシ基、ホスフィニルアミノ基、シリル基、ヒドラジノ基、イミノ基。これらの基は、更に置換可能な基である場合、更に置換基を有してもよい。置換基としては、上述した置換基Tで説明した基が挙げられる。
なお、波長420~550nmの範囲における平均吸光度の値は、λmaxにおける吸光度の値を1として波長420~550nmの範囲における各吸光度を規格化した値を加重平均して算出するものとする。
本発明の組成物は硬化性化合物を含有する。硬化性化合物としては、重合性化合物、樹脂等が挙げられる。樹脂は、非重合性の樹脂(重合性基を有さない樹脂)であってもよく、重合性の樹脂(重合性基を有する樹脂)であってもよい。重合性基としては、エチレン性不飽和結合含有基、環状エーテル基、メチロール基、アルコキシメチル基などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、ビニルフェニル基、(メタ)アリル基、(メタ)アクリロイル基、(メタ)アクリロイルオキシ基、(メタ)アクリロイルアミド基などが挙げられ、(メタ)アリル基、(メタ)アクリロイル基および(メタ)アクリロイルオキシ基が好ましく、(メタ)アクリロイルオキシ基がより好ましい。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられ、エポキシ基が好ましい。
重合性化合物としては、エチレン性不飽和結合含有基を有する化合物、環状エーテル基を有する化合物、メチロール基を有する化合物、アルコキシメチル基を有する化合物等が挙げられる。エチレン性不飽和結合含有基を有する化合物はラジカル重合性化合物として好ましく用いることができる。また、環状エーテル基を有する化合物は、カチオン重合性化合物として好ましく用いることができる。
また、アルコキシメチル基を有する化合物(以下、アルコキシメチル化合物ともいう)としては、アルコキシメチル基が窒素原子または芳香族環を形成する炭素原子に結合している化合物が挙げられる。アルコキシメチル基またはメチロール基が窒素原子に結合している化合物としては、アルコキシメチル化メラミン、メチロール化メラミン、アルコキシメチル化ベンゾグアナミン、メチロール化ベンゾグアナミン、アルコキシメチル化グリコールウリル、メチロール化グリコールウリル、アルコキシメチル化尿素およびメチロール化尿素等が好ましい。また、特開2004-295116号公報の段落0134~0147、特開2014-089408号公報の段落0095~0126に記載された化合物を用いることもできる。
本発明の組成物は、硬化性化合物として樹脂を用いることができる。硬化性化合物は、樹脂を少なくとも含むものを用いることが好ましい。樹脂は、例えば、顔料等を組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料等を組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。なお、重合性基を有する樹脂は、重合性化合物にも該当する。
本発明の組成物は、上述した特定色素以外の赤外線吸収剤(他の赤外線吸収剤)を含有することができる。更に他の赤外線吸収剤を含有することで、より幅広い波長範囲の赤外線を遮蔽できる膜を形成することができる。他の赤外線吸収剤は、染料であってもよく、顔料(粒子)であってもよい。他の赤外線吸収剤としては、ピロロピロール化合物、シアニン化合物、スクアリリウム化合物、フタロシアニン化合物、ナフタロシアニン化合物、クアテリレン化合物、メロシアニン化合物、クロコニウム化合物、オキソノール化合物、イミニウム化合物、ジチオール化合物、トリアリールメタン化合物、ピロメテン化合物、アゾメチン化合物、アントラキノン化合物、ジベンゾフラノン化合物、ジチオレン金属錯体、金属酸化物、金属ホウ化物等が挙げられる。ピロロピロール化合物としては、特開2009-263614号公報の段落番号0016~0058に記載の化合物、特開2011-068731号公報の段落番号0037~0052に記載の化合物、国際公開第2015/166873号の段落番号0010~0033に記載の化合物などが挙げられる。スクアリリウム化合物としては、特開2011-208101号公報の段落番号0044~0049に記載の化合物、特許第6065169号公報の段落番号0060~0061に記載の化合物、国際公開第2016/181987号の段落番号0040に記載の化合物、特開2015-176046号公報に記載の化合物、国際公開第2016/190162号の段落番号0072に記載の化合物、特開2016-074649号公報の段落番号0196~0228に記載の化合物、特開2017-067963号公報の段落番号0124に記載の化合物、国際公開第2017/135359号に記載の化合物、特開2017-114956号公報に記載の化合物、特許6197940号公報に記載の化合物、国際公開第2016/120166号に記載の化合物などが挙げられる。シアニン化合物としては、特開2009-108267号公報の段落番号0044~0045に記載の化合物、特開2002-194040号公報の段落番号0026~0030に記載の化合物、特開2015-172004号公報に記載の化合物、特開2015-172102号公報に記載の化合物、特開2008-088426号公報に記載の化合物、国際公開第2016/190162号の段落番号0090に記載の化合物、特開2017-031394号公報に記載の化合物などが挙げられる。クロコニウム化合物としては、特開2017-082029号公報に記載の化合物が挙げられる。イミニウム化合物としては、例えば、特表2008-528706号公報に記載の化合物、特開2012-012399号公報に記載の化合物、特開2007-092060号公報に記載の化合物、国際公開第2018/043564号の段落番号0048~0063に記載の化合物が挙げられる。フタロシアニン化合物としては、特開2012-077153号公報の段落番号0093に記載の化合物、特開2006-343631号公報に記載のオキシチタニウムフタロシアニン、特開2013-195480号公報の段落番号0013~0029に記載の化合物、特許第6081771号公報に記載のバナジウムフタロシアニン化合物、国際公開第2020/071470号に記載の化合物が挙げられる。ナフタロシアニン化合物としては、特開2012-077153号公報の段落番号0093に記載の化合物が挙げられる。ジチオレン金属錯体としては、特許第5733804号公報に記載の化合物が挙げられる。金属酸化物としては、例えば、酸化インジウムスズ、酸化アンチモンスズ、酸化亜鉛、Alドープ酸化亜鉛、フッ素ドープ二酸化スズ、ニオブドープ二酸化チタン、酸化タングステンなどが挙げられる。酸化タングステンの詳細については、特開2016-006476号公報の段落番号0080を参酌でき、この内容は本明細書に組み込まれる。金属ホウ化物としては、ホウ化ランタンなどが挙げられる。ホウ化ランタンの市販品としては、LaB6-F(日本新金属(株)製)などが挙げられる。また、金属ホウ化物としては、国際公開第2017/119394号に記載の化合物を用いることもできる。酸化インジウムスズの市販品としては、F-ITO(DOWAハイテック(株)製)などが挙げられる。
本発明の組成物は、上述したように特定色素そのものが色素誘導体(以下、「誘導体」とも称する)であってもよいが、上述した特定色素の他に、更に色素誘導体を含有することもできる。色素誘導体は分散助剤として用いられる。色素誘導体としては、色素骨格に酸基または塩基性基が結合した構造を有する化合物が挙げられる。
本発明の組成物好ましい一態様として、上述した特定色素(ただし、色素誘導体ではない)に加えて、色素誘導体として、式(1)のXa、Xb、Ya、Yb、R1およびR2の少なくとも1つが、式(R-100)で表される基を置換基として有する色素を含む態様も挙げられる。このような態様の場合、色素誘導体は、式(1)のR1およびR2の少なくとも1つが、式(R-100)で表される基を置換基として有する色素であることがより好ましい。また、色素誘導体が式(1)のR1およびR2の少なくとも1つが後述する式(A-1)~(B-2)で表される基を有する化合物であることも好ましい。
本発明の組成物は、溶剤を含有することが好ましい。溶剤としては、水、有機溶剤が挙げられ、有機溶剤であることが好ましい。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、 ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の組成物が重合性化合物を含む場合、本発明の組成物は更に光重合開始剤を含有することが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。
本発明の組成物が環状エーテル基を有する化合物を含む場合、硬化剤をさらに含むことが好ましい。硬化剤としては、例えばアミン系化合物、酸無水物系化合物、アミド系化合物、フェノール系化合物、多価カルボン酸、チオール化合物などが挙げられる。硬化剤の具体例としては、コハク酸、トリメリット酸、ピロメリット酸、N,N-ジメチル-4-アミノピリジン、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)などが挙げられる。硬化剤は、特開2016-075720号公報の段落番号0072~0078に記載の化合物、特開2017-036379号公報に記載の化合物を用いることもできる。硬化剤の含有量は、環状エーテル基を有する化合物の100質量部に対し、0.01~20質量部が好ましく、0.01~10質量部がより好ましく、0.1~6.0質量部がさらに好ましい。
本発明の組成物は、有彩色着色剤を含有することができる。本発明において、有彩色着色剤とは、白色着色剤および黒色着色剤以外の着色剤を意味する。有彩色着色剤は、波長400nm以上650nm未満の範囲に吸収を有する着色剤が好ましい。
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等(以上、オレンジ色顔料)、
C.I.Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294(キサンテン系、Organo Ultramarine、Bluish Red),295(モノアゾ系),296(ジアゾ系),297(アミノケトン系)等(以上、赤色顔料)、
C.I.Pigment Green 7,10,36,37,58,59,62,63,64(フタロシアニン系),65(フタロシアニン系),66(フタロシアニン系)等(以上、緑色顔料)、
C.I.Pigment Violet 1,19,23,27,32,37,42,60(トリアリールメタン系),61(キサンテン系)等(以上、紫色顔料)、
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(モノアゾ系),88(メチン系)等(以上、青色顔料)。
本発明の組成物は、赤外線を透過させて可視光を遮光する色材(以下、可視光を遮光する色材ともいう)を含有することもできる。可視光を遮光する色材を含む組成物は、赤外線透過フィルタ形成用の組成物として好ましく用いられる。
(A):2種類以上の有彩色着色剤を含み、2種以上の有彩色着色剤の組み合わせで黒色を形成している。
(B):有機系黒色着色剤を含む。
(1)黄色着色剤、青色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(2)黄色着色剤、青色着色剤および赤色着色剤を含有する態様。
(3)黄色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(4)黄色着色剤および紫色着色剤を含有する態様。
(5)緑色着色剤、青色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(6)紫色着色剤およびオレンジ色着色剤を含有する態様。
(7)緑色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(8)緑色着色剤および赤色着色剤を含有する態様。
本発明の組成物は界面活性剤を含有することが好ましい。界面活性剤としては、フッ素系界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、アニオン性界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。
本発明の組成物は重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられ、p-メトキシフェノールが好ましい。重合禁止剤の含有量は、組成物の全固形分中、0.0001~5質量%が好ましい。組成物は重合禁止剤を1種のみ含んでいてもよく、2種以上含んでいてもよい。2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の組成物はシランカップリング剤を含有することができる。本明細書において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応および縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤は、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。シランカップリング剤の含有量は、組成物の全固形分中0.01~15.0質量%が好ましく、0.05~10.0質量%がより好ましい。組成物はシランカップリング剤を1種のみ含んでいてもよく、2種以上含んでいてもよい。2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物、メロシアニン色素などが挙げられる。このような化合物の具体例としては、特開2009-217221号公報の段落番号0038~0052、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の市販品としては、BASF社製のTinuvinシリーズ、Uvinul(ユビナール)シリーズなどが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059、国際公開第2016/181987号の段落番号0059~0076に記載された化合物を用いることもできる。紫外線吸収剤の含有量は、組成物の全固形分中0.01~30質量%が好ましく、0.05~25質量%がより好ましい。組成物は紫外線吸収剤を1種のみ含んでいてもよく、2種以上含んでいてもよい。2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物を使用することもできる。酸化防止剤の含有量は、組成物の全固形分中0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。組成物は酸化防止剤を1種のみ含んでいてもよく、2種以上含んでいてもよい。2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本発明の組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。
本発明の組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、容器内壁は、容器内壁からの金属溶出を防ぎ、組成物の経時安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。
本発明の組成物は、前述の成分を混合して調製できる。組成物の調製に際しては、全成分を同時に溶剤に溶解または分散して組成物を調製してもよいし、必要に応じては、各成分を適宜配合した2つ以上の溶液または分散液をあらかじめ調製し、使用時(塗布時)にこれらを混合して組成物として調製してもよい。
次に、本発明の膜について説明する。本発明の膜は、上述した本発明の組成物から得られるものである。本発明の膜は、光学フィルタとして好ましく用いることができる。光学フィルタの用途は、特に限定されないが、赤外線カットフィルタ、赤外線透過フィルタなどが挙げられる。赤外線カットフィルタとしては、例えば、固体撮像素子の受光側における赤外線カットフィルタ(例えば、ウエハーレベルレンズに対する赤外線カットフィルタ用など)、固体撮像素子の裏面側(受光側とは反対側)における赤外線カットフィルタ、環境光センサー用の赤外線カットフィルタ(例えば、情報端末装置が置かれた環境の照度や色調を感知してディスプレイの色調を調整する照度センサーや、色調を調整する色補正用センサー)などが挙げられる。特に、固体撮像素子の受光側における赤外線カットフィルタとして好ましく用いることができる。赤外線透過フィルタとしては、可視光を遮光し、特定の波長以上の赤外線を選択的に透過可能なフィルタが挙げられる。
また、波長400nm付近の光の遮光性能力については、波長390nmにおける透過率(紫外線遮蔽性)で評価することができ、紫外線遮蔽性が5%以下であることが好ましい。
(i1):波長400~850nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~850nmの範囲の光を遮光して、波長950nmを超える光を透過させることができる。
(i2):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1050nmを超える光を透過させることができる。
(i3):波長400~1050nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1200~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~1050nmの範囲の光を遮光して、波長1150nmを超える光を透過させることができる。
また、波長400nm付近の光の遮光性能力については、波長390nmにおける透過率(紫外線遮蔽性)で評価することができ、紫外線遮蔽性が5%以下であることが好ましい。
本発明の膜は、本発明の組成物を塗布する工程を経て製造できる。
フォトリソグラフィ法でのパターン形成方法は、本発明の組成物を塗布して形成した組成物層に対しパターン状に露光する工程(露光工程)と、未露光部の組成物層を現像除去してパターンを形成する工程(現像工程)と、を含むことが好ましい。必要に応じて、現像されたパターンをベークする工程(ポストベーク工程)を設けてもよい。以下、各工程について説明する。
ドライエッチング法でのパターン形成は、上記組成物を支持体上に塗布して形成した組成物層を硬化して硬化物層を形成し、次いで、この硬化物層上にパターニングされたフォトレジスト層を形成し、次いで、パターニングされたフォトレジスト層をマスクとして硬化物層に対してエッチングガスを用いてドライエッチングするなどの方法で行うことができる。フォトレジスト層の形成においては、プリベーク処理を施すことが好ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落番号0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、赤外線カットフィルタおよび赤外線透過フィルタなどが挙げられる。
本発明の固体撮像素子は、上述した本発明の膜を含む。固体撮像素子の構成としては、本発明の膜を有する構成であり、固体撮像素子として機能する構成であれば特に限定はない。例えば、以下のような構成が挙げられる。
本発明の画像表示装置は、本発明の膜を含む。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス(有機EL)表示装置などが挙げられる。画像表示装置の定義や詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。画像表示装置は、白色有機EL素子を有するものであってもよい。白色有機EL素子としては、タンデム構造であることが好ましい。有機EL素子のタンデム構造については、特開2003-045676号公報、三上明義監修、「有機EL技術開発の最前線-高輝度・高精度・長寿命化・ノウハウ集-」、技術情報協会、326~328ページ、2008年などに記載されている。有機EL素子が発光する白色光のスペクトルは、青色領域(430~485nm)、緑色領域(530~580nm)及び黄色領域(580~620nm)に強い極大発光ピークを有するものが好ましい。これらの発光ピークに加え更に赤色領域(650~700nm)に極大発光ピークを有するものがより好ましい。
本発明の赤外線センサは、上述した本発明の膜を含む。赤外線センサの構成としては、赤外線センサとして機能する構成であれば特に限定はない。以下、本発明の赤外線センサの一実施形態について、図面を用いて説明する。
本発明のカメラモジュールは、固体撮像素子と、上述した本発明の膜を含む。カメラモジュールは、レンズ、及び、固体撮像素子から得られる撮像を処理する回路を更に有することが好ましい。カメラモジュールに用いられる固体撮像素子としては、上記本開示に係る固体撮像素子であってもよいし、公知の固体撮像素子であってもよい。また、カメラモジュールに用いられるレンズ、及び、上記固体撮像素子から得られる撮像を処理する回路としては、公知のものを用いることができる。カメラモジュールの例としては、特開2016-006476号公報、及び、特開2014-197190号公報に記載のカメラモジュールを参酌でき、これらの内容は本明細書に組み込まれる。
本発明の化合物は、式(1)で表される化合物である。
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す。
本発明の赤外線吸収剤は、式(1)で表される化合物を含む。赤外線吸収剤は、式(1)で表される化合物を1種のみ含んでいてもよく、2種以上含んでいてもよい。また、本発明の赤外線吸収剤は、式(1)で表される化合物の分解物を含んでいてもよい。
窒素雰囲気下、三口フラスコにアセチルコハク酸ジエチル(Diethyl acetylsuccinate)を75.0g、酢酸アンモニウム267.4g、酢酸375mLを添加し、加熱還流下3時間撹拌した。この反応液を25℃まで冷却し、酢酸エチル300mL、ヘキサン300mL、蒸留水600mLを添加した後、反応液の内温を20~25℃に保った状態で30分間撹拌した。水層に対して酢酸エチル:ヘキサン=1:1の混合液600mLで3回分液操作を行った後、有機層をすべて合わせたのち、70℃で減圧濃縮し、得られた残渣に蒸留水300mLを添加して20分撹拌した。この反応液を濾過し、蒸留水300mLでかけ洗いを行い、得られた固体について50℃で12時間送風乾燥を行うことで、中間体1を18.9g(収率32.2%)得た。
1H-NMR(CDCl3):δ=1.30(t、J=7.1Hz、3H)、2.36-2.37(m、3H)、3.29-3.31(m、2H)、4.20(q、J=7.1Hz、2H)、8.06(s、1H)
窒素雰囲気下、三口フラスコにナトリウムペントキシド71.77g、t-アミルアルコール600mLを室温にて添加し、加熱還流下、t-アミルアルコールを400mL留去した。得られた反応液に、反応液の内温を105~115℃に保った状態でスルホこはく酸ビス(2-エチルヘキシル)ナトリウム158mgを添加し、続いてブチロニトチル33.54gを添加した。次いで、得られた反応液に、反応液の内温を105~115℃に保った状態で中間体1の15.0gをt-アミルアルコール50mLに懸濁した液を10分間かけて滴下し、さらに加熱還流下1時間撹拌した。得られた反応液を40℃まで冷却し、反応液の内温を40℃~70℃の範囲に保った状態でメタノール105mL、酢酸71.88gを順次滴下した後、反応液を25℃まで冷却し、さらに反応液の内温を20℃~30℃の範囲に保った状態で酢酸エチル210mL、飽和食塩水210mL、蒸留水105mLを順次添加した。次いで、この反応液を25℃で5分間撹拌した後、ろ過し、蒸留水105mLでかけ洗いを行い、未精製の固体を得た。得られた固体を三口フラスコへ添加し、蒸留水53mLを加え30分間撹拌した後、ろ過し、蒸留水53mLでかけ洗いを行い、得られた固体について50℃で12時間送風乾燥を行うことで、中間体2を3.40g(収率20.0%)得た。
1H-NMR(重DMSO(ジメチルスルホキシド)):δ=0.90(t、J=7.4Hz、3H)、1.70(sext、J=7.4Hz、2H)、2.15(s、3H)、2.45(t、J=7.4Hz、2H)、10.1-10.2(m、2H)
窒素雰囲気下、三口フラスコにマロノニトリル237.46g、酢酸201mL、メタノール1977mLを添加し、フラスコ内の液温を40℃以下に保った状態で、o-アミノチオフェノール450gをメタノール150mLで洗いこみながら滴下した。得られた反応液を30℃で2時間撹拌した後、10℃以下で30分撹拌してろ過し、冷メタノール300mLでかけ洗いをし、得られた結晶について40℃で12時間送風乾燥を行うことで中間体3を510.55g(収率81.5%)得た。
1H-NMR(CDCl3):δ=4.24(s、2H)、7.44(m、1H)、7.53(m、1H)、7.89(m、1H)、8.04(m、1H)
窒素雰囲気下、三口フラスコに中間体2を3.0g、中間体3を13.05g、トルエン63mLを添加し、加熱還流下、トルエンを3mL留去した。得られた反応液を95℃まで冷却し、反応液の内温を90~95℃の範囲を保ちながらオキシ塩化リン7.18gを添加した後、加熱還流下にて1時間撹拌した。得られた反応液を10℃以下まで冷却し、反応液の内温を0℃~10℃に保ちながらヘキサン90mLを滴下した後、反応液の内温を0℃~10℃に保ちながら30分間撹拌した。次いで、この反応液を濾過し、ヘキサン15mLでかけ洗いをおこない、固体を得た。得られた固体を三口フラスコへ添加し、飽和重曹水75mLを加えて5分間撹拌した後、ろ過し、飽和重曹水15mLでかけ洗いを行い、固体を得た。次に、得られた固体を三口フラスコへ添加し、メタノール:蒸留水=4:1の混合液60mLを加えて5分間撹拌した後、ろ過し、メタノール:蒸留水=4:1の混合液60mLでかけ洗いを行い、固体を得た。さらに、得られた固体を三口フラスコへ添加し、メタノール:蒸留水=9:1の混合液60mLを加えて5分間撹拌した後、ろ過し、次いで、メタノール:蒸留水=9:1の混合液60mLでかけ洗いを行い、得られた固体について50℃で12時間送風乾燥を行うことで、中間体4を0.08g(収率1.0%)得た。
窒素雰囲気下、三口フラスコに中間体4の0.08g、ジフェニルボリン酸2-アミノエチルの0.29g、トルエンの2mLを添加し、90~100℃の範囲を保ちながら四塩化チタンの0.36gをトルエンの2mLで洗いこみながら添加した。この反応液を加熱還流下にて2時間撹拌した後、20℃まで冷却し、反応液の内温を20℃~30℃に保ちながらメタノールの2mLを添加した。得られた結晶をろ過してメタノールの1mLでかけ洗い、得られた粗体にメタノールの2mLを添加し、加熱還流下30分間撹拌した後、20℃まで冷却し、ろ過してメタノール1mLでかけ洗いを行い、次いで、得られた結晶について50℃で12時間送風乾燥を行うことで、色素PPB-A-13の0.06g(収率46.2%)を得た。MALDI TOF-MASS(飛行時間型質量分析法)による質量分析の結果、得られた結晶は下記構造の色素PPB-A-13であることを同定した。
MALDI TOF-MASS:Calc.for [M+H]+:833.3found:833.4
中間体5を中間体2と同様の手法にて合成した。窒素雰囲気下、三口フラスコに中間体5の0.75g、ベンゾニトリル7.5gを添加し、35℃にてジクロロリン酸フェニル2.16gを添加した。この反応液を35℃にて30分間撹拌した後、50℃まで昇温し、1時間撹拌し、さらに70℃に昇温して1時間撹拌し、反応液Aを調製した。
続いて、窒素雰囲気下、中間体3の2.85g、トルエン14.3gを添加し、加熱還流下、トルエンを3mL留去した。得られた反応液を95℃まで冷却し、反応液の内温を90~95℃の範囲を保ちながら反応液Aを30分間かけて滴下し、ジクロロリン酸フェニル2.16gを添加した後、90~95℃にて15分間撹拌した。得られた反応液を10℃以下まで冷却し、反応液の内温を0℃~10℃に保ちながらヘキサン44.2gを滴下した後、反応液の内温を0℃~10℃に保ちながら30分間撹拌した。次いで、この反応液を濾過し、ヘキサン10gでかけ洗いをおこない、固体を得た。得られた固体を三口フラスコへ添加し、飽和重曹水19mLを加えて5分間撹拌した後、さらにメタノール38mLを加えて5分間撹拌した後、ろ過し、固体を得た。さらに、得られた固体を三口フラスコへ添加し、メタノール:蒸留水=9:1の混合液20mLを加えて5分間撹拌した後、ろ過し、次いで、メタノール:蒸留水=9:1の混合液30mLでかけ洗いを行い、得られた固体について50℃で12時間送風乾燥を行うことで、中間体6を0.9g得た。
窒素雰囲気下、三口フラスコに中間体6の0.8g、ジフェニルボリン酸2-アミノエチルの2.7g、トルエンの16mLを添加し、90~100℃の範囲を保ちながら四塩化チタンの3.42gをトルエンの2mLで洗いこみながら添加した。この反応液を加熱還流下にて2時間撹拌した後、20℃まで冷却し、メタノール208mLに内温を20℃~30℃に保ちながら滴下した。この反応液を30分間撹拌した後、得られた結晶をろ過してメタノールの44mLでかけ洗いをした。得られた粗体をシリカゲルカラムクロマトグラフィー(クロロホルム)で精製し、得られた結晶について50℃で12時間送風乾燥を行うことで、色素PPB-A-45の0.09gを得た。
1H-NMR (CDCl3) δ 7.74(2H、d、J=8.2Hz)、7.73(2H、d、J=8.2Hz)、7.69-7.51(6H、m)、7.42-7.07(18H、m)、3.48(1H,m)、2.93(2H、m)、1.54(2H、m)、0.82(3H、d、J=7.4Hz)、0.78(3H、d、J=7.4Hz)、0.60(3H、t、J=7.4Hz)
下記表に記載の色素を、下記表に記載の溶媒に溶解させて色素溶液を調製した。得られた色素溶液の波長400~1200nmの光に対する吸光度を分光光度計U-4100((株)日立ハイテクノロジーズ製)を用いて測定した。波長400nm~1200nmの範囲において、吸光度が最も大きい値を示す波長(λmax)を測定し、λmaxでの吸光度の値を1とした際の、波長420~550nmの範囲における平均吸光度の値を算出して、下記基準で可視透明性を評価した。平均吸光度が小さいほど、可視透明性が高いと言える。
A:波長420~550nmの平均吸光度が0.005未満
B:波長420~550nmの平均吸光度が0.005以上0.010未満
C:波長420~550nmの平均吸光度が0.010以上
各色素の詳細は以下の通りである。
PPB-C-1~PPB-C-3:下記構造の化合物(式(1)で表される色素(特定色素)である)
PPB-D-1、PPB-D-2、PPB-E-1:下記構造の化合物(比較色素である)
下記表に記載の色素(顔料)の1.902質量部、下記表に記載の誘導体の0.36質量部、下記表に記載の分散剤の9質量部、下記表に記載の溶剤の18.74質量部、及び、直径0.3mmのジルコニアビーズ40質量部を混合し、ペイントシェーカーを用いて5時間分散処理を行い、ビーズをろ過で分離して分散液を製造した。
PPB-A-1~PPB-A-45:上述した構造の化合物(式(1)で表される色素(特定色素)である)
PPB-D-1、PPB-D-2:上述した構造の化合物(比較色素である)
PPB-B-1~PPB-B-16:下記構造の化合物(PPB-B-1~PPB-B-13、PPB-B-15、PPB-B-16は、式(1)で表される色素(特定色素)であり、PPB-B-14は、式(1)で表される色素(特定色素)とは異なる化合物である。)
D-1:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数を表す。重量平均分子量38900、酸価99.1mgKOH/g)をプロピレングリコールモノメチルエーテルアセテート:プロピレングリコールモノメチルエーテル=9:1(質量比)の混合溶液で固形分濃度を20質量%に調整した溶液
D-2:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数を表す。重量平均分子量21000、酸価36.0mgKOH/g、アミン価47.0mgKOH/g)をプロピレングリコールモノメチルエーテルアセテート:プロピレングリコールモノメチルエーテル=9:1(質量比)の混合溶液で固形分濃度を20質量%に調整した溶液
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:プロピレングリコールモノメチルエーテル
下記表に記載の色素(染料)の8.02質量部、下記表に記載の溶剤の91.98質量部を混合して色素溶液を製造した。
PPB-C-1~PPB-C-3:上述した構造の化合物(式(1)で表される色素(特定色素)である)
PPB-E-1:上述した構造の化合物(比較色素である)
S-3:シクロペンタノン
S-4:シクロヘキサノン
S-5:アニソール
各素材を、以下に示す処方1~6の割合で混合し、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して各組成物を製造した。
下記表に記載の分散液 ・・・15.873質量部
下記表に記載の樹脂 ・・・2.943質量部
下記表に記載の重合性化合物 ・・・0.45質量部
下記表に記載の光重合開始剤 ・・・0.45質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.0075質量部
下記表に記載の溶剤 :10.276質量部
下記表に記載の分散液 ・・・15.873質量部
下記表に記載の樹脂 ・・・2.943質量部
下記表に記載のエポキシ化合物 ・・・0.9質量部
下記表に記載の硬化剤(表中に記載がある場合) ・・0.045質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.0075質量部
下記表に記載の溶剤 ・・・10.276質量部
下記表に記載の色素溶液 ・・・14.921質量部
下記表に記載の樹脂 ・・・3.895質量部
下記表に記載の重合性化合物 ・・・0.45質量部
下記表に記載の光重合開始剤 ・・・0.45質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.00075質量部
下記表に記載の溶剤 ・・・10.276質量部
下記表に記載の色素溶液 ・・・14.921質量部
下記表に記載の樹脂 ・・・3.895質量部
下記表に記載のエポキシ化合物 ・・・0.9質量部
下記表に記載の硬化剤(表中に記載がある場合) ・・・0.045質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.0075質量部
下記表に記載の溶剤 ・・・10.276質量部
下記表に記載の分散液 ・・・8.333質量部
下記構造の樹脂(重量平均分子量24600、主鎖に付記した数値は繰り返し単位の質量比を表す。)の固形分濃度45質量%プロピレングリコールモノメチルエーテルアセテート溶液 ・・・4.886質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.011質量部
下記表に記載の溶剤 ・・・6.305質量部
下記表に記載の色素溶液 ・・・7.833質量部
下記構造の樹脂(重量平均分子量24600、主鎖に付記した数値は繰り返し単位の質量比を表す。)の固形分濃度45質量%プロピレングリコールモノメチルエーテルアセテート溶液 ・・・5.386質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
下記表に記載の界面活性剤 ・・・0.011質量部
下記表に記載の溶剤 ・・・6.030質量部
E-1:メタクリル酸ベンジル、メタクリル酸、メタクリル酸2-ヒドロキシエチルの共重合樹脂(重量平均分子量14000、酸価77mgKOH/g、アルカリ可溶性樹脂)
E-2:ARTON F4520(JSR(株)製、環状ポリオレフィン樹脂)
E-3:下記構造の樹脂(重量平均分子量40000、酸価100mgKOH/g、主鎖に付記した数値は繰り返し単位の質量比を表す。アルカリ可溶性樹脂)
M-1:アロニックスM-305(東亞合成(株)製、ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートとの混合物。ペンタエリスリトールトリアクリレートの含有量が55質量%~63質量%である。)
M-2:KAYARAD RP-1040(日本化薬(株)製、エチレンオキサイド変性ペンタエリスリトールテトラアクリレート)
M-3:アロニックスM-510(東亞合成(株)製、多塩基酸変性アクリルオリゴマー)
C-1:Irgacure OXE01(BASF社製、オキシムエステル系開始剤)
C-2:Irgacure OXE02(BASF社製、オキシムエステル系開始剤)
C-3:Omnirad 907(IGM Resins B.V.社製、α-アミノアルキルフェノン系開始剤)
F-1:メタクリル酸グリシジル骨格ランダムポリマー(日油(株)製、マープルーフG-0150M、重量平均分子量10000)
F-2:EPICLON N-695(DIC(株)製、ノボラック型エポキシ樹脂)
F-3:JER1031S(三菱ケミカル(株)製、多官能エポキシ樹脂)
F-4:EHPE3150((株)ダイセル製、2,2-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物)
G-1:トリメリット酸
G-2:ピロメリット酸無水物
G-3:N,N-ジメチル-4-アミノピリジン
G-4:ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)
H-1:メガファックRS-72-K(DIC(株)製、フッ素系界面活性剤)
H-2: 下記構造の化合物(重量平均分子量14000、繰り返し単位の割合を示す%の数値はモル%である)
U-1:Uvinul3050(BASF製、下記構造の化合物)
U-3:Tinuvin326(BASF製、下記構造の化合物)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロペンタノン
S-4:シクロヘキサノン
(製造例1) 実施例1~51、比較例1~3の組成物を用いた膜の製造方法
各組成物をガラス基板上にスピンコート法で塗布し、その後ホットプレートを用いて100℃で2分間加熱して組成物層を得た。得られた組成物層を、i線ステッパーを用い、500mJ/cm2の露光量にて露光した。次いで、露光後の組成物層に対してホットプレートを用いて220℃で5分間加熱して硬化処理を行い、厚さ1.5μmの膜を得た。
上記で調製した各組成物を、ガラス基板上にスピンコート法で塗布し、その後ホットプレートを用いて100℃で10分間加熱(プリベーク)し、次いで、200℃で8分間加熱して硬化処理を行い、厚さ1.5μmの膜を得た。
上記で調製した各組成物を、ガラス基板上にスピンコート法で塗布し、その後ホットプレートを用いて100℃で10分間加熱(プリベーク)し、次いで、200℃で8分間加熱して硬化処理を行い、厚さ8.0μmの膜を得た。
得られた膜について絶対PL量子収率測定装置C9920-03G(浜松ホトニクス(株)製)を用いて、蛍光量子収率を測定し、下記基準で蛍光量子収率を評価した。
A:蛍光量子収率が0.01未満
B:蛍光量子収率が0.01以上
得られた膜について波長400nm~1200nmの光に対する吸光度を分光光度計U-4100((株)日立ハイテクノロジーズ製)を用いて測定した。波長400nm~1200nmの範囲において、吸光度が最も大きい値を示す波長(λmax)を測定し、λmaxでの吸光度の値を1とした際の、波長420~550nmの範囲における平均吸光度の値を算出して、下記基準で可視透明性を評価した。
A:波長420~550nmの平均吸光度が0.025未満
B:波長420~550nmの平均吸光度が0.025以上0.050未満
C:波長420~550nmの平均吸光度が0.050以上
得られた膜を150℃の恒温器に入れて1000時間の加熱処理を行った。加熱処理後の膜について、波長400~1200nmの光に対する吸光度を分光光度計U-4100((株)日立ハイテクノロジーズ製)を用いて測定した。波長400nm~1200nmの範囲において、吸光度が最も大きい値を示す波長(λmax)を測定し、λmaxでの吸光度の値を1とした際の、波長420~550nmの範囲における平均吸光度の値を算出して、下記基準で加熱後の可視透明性を評価した。
A:波長420~550nmの平均吸光度が0.025未満
B:波長420~550nmの平均吸光度が0.025以上0.050未満
C:波長420~550nmの平均吸光度が0.050以上
得られた膜について波長400~1200nmの波長の光の透過率を分光光度計U-4100((株)日立ハイテクノロジーズ製)を用いて測定した。次いで、膜を150℃の恒温器に入れて1000時間の加熱処理を行った。加熱処理後の膜について、同様に波長400~1200nmの波長の光の透過率を測定し、加熱処理前後における波長400~1200nmの範囲の各波長での透過率変化(ΔT)を測定して透過率変化の最大値(ΔTmax)を求め、下記基準で透過率変化の最大値(ΔTmax)を評価した。
透過率変化(ΔT)=|加熱処理前の膜の透過率(%)-加熱処理後の膜の透過率(%)|
ここで、ΔTmaxとは上記で算出される波長400~1200nmの各波長での透過率変化ΔTで最も大きい値を意味する。
A:波長400~1200nmの透過率変化ΔTmaxが4%未満
B:波長400~1200nmの透過率変化ΔTmaxが4%以上10%未満
C:波長400~1200nmの透過率変化ΔTmaxが10%以上
また、実施例701~751の組成物を用いて得られた膜は、いずれも波長390nmにおける透過率が5%であり、紫外線遮蔽性にも優れていた。
さらに、実施例1~19、21、25、26、27、29~51、401~419、421、425、426、427、429~451、701~719、721、725、726、727、729~751については耐光性にも優れていた。
式(D)中、Rz 5~Rz 9はそれぞれ独立して、置換基を表し、Rz 5とRz 6、Rz 6とRz 7、Rz 7とRz 8、Rz 8とRz 9はそれぞれ互いに連結して環を形成してもよい。
各素材を、以下に示す処方の割合で混合し、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して組成物IRを製造した。
赤外線吸収剤(FDR-3、山田化学工業株式会社製) ・・・0.045質量部
下記構造の樹脂(重量平均分子量24600、主鎖に付記した数値は繰り返し単位の質量比を表す。)の固形分濃度45質量%プロピレングリコールモノメチルエーテルアセテート溶液 ・・・6.9質量部
重合禁止剤(p-メトキシフェノール) ・・・0.001質量部
プロピレングリコールモノメチルエーテルアセテート ・・・6.705質量部
(実施例1001~1051)
上記で調製した組成物IRを、ガラス基板上にポストベーク後の膜厚が7.0μmとなるようにスピンコート法で塗布し、その後ホットプレートを用いて100℃で10分間加熱(プリベーク)し、次いで、200℃で8分間加熱して硬化処理を行い、厚さ7.0μmの膜を得た。得られた膜上に2層目用の組成物として実施例401~451の組成物をポストベーク後の2層目の膜厚が1.0μmとなるようにガラス基板上にスピンコート法で塗布し、その後ホットプレートを用いて100℃で10分間加熱(プリベーク)し、次いで、200℃で8分間加熱して硬化処理を行い、厚さ1.0μmの2層目の膜を形成して厚さ8.0μmの積層膜を得た。
Claims (14)
- 式(1)で表される色素と、硬化性化合物と、を含む組成物;
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す;
Ra11~Ra29はそれぞれ独立して、水素原子または置換基を表し、
XcおよびXdはそれぞれ独立して、S、OまたはNRX2を表し、RX2は水素原子または置換基を表し、
A1は、置換基を有していてもよい芳香族炭化水素環、芳香族複素環またはこれらの縮合環を表す。 - 前記式(1)のYaおよびYbはそれぞれ独立して、-BRY1RY2を表し、RY1およびRY2は、それぞれ独立して水素原子、ハロゲン原子、アルキル基、アルケニル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基またはヘテロアリールオキシ基を表し、RY1およびRY2は互いに結合して環を形成していてもよい、
請求項1または2に記載の組成物。 - 前記式(1)のR1およびR2の少なくとも一方が、置換基を有してもよい炭素数9以下のアルキル基である、請求項1~3のいずれか1項に記載の組成物。
- 前記式(1)で表される色素が極大吸収波長を波長650nm以上に有する、請求項1~5のいずれか1項に記載の組成物。
- 請求項1~6のいずれか1項に記載の組成物を用いて得られる膜。
- 請求項7に記載の膜を含む光学フィルタ。
- 請求項7に記載の膜を含む固体撮像素子。
- 請求項7に記載の膜を含む画像表示装置。
- 請求項7に記載の膜を含む赤外線センサ。
- 請求項7に記載の膜を含むカメラモジュール。
- 式(1)で表される化合物;
YaおよびYbはそれぞれ独立して、水素原子または置換基を表し、
R1およびR2はそれぞれ独立して、置換基を有していてもよい脂肪族炭化水素基を表す;
Ra11~Ra29はそれぞれ独立して、水素原子または置換基を表し、
XcおよびXdはそれぞれ独立して、S、OまたはNRX2を表し、RX2は水素原子または置換基を表し、
A1は、置換基を有していてもよい芳香族炭化水素環、芳香族複素環またはこれらの縮合環を表す。 - 請求項13に記載の化合物を含む赤外線吸収剤。
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