WO2007111157A1 - Near infrared absorbing material - Google Patents

Near infrared absorbing material Download PDF

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Publication number
WO2007111157A1
WO2007111157A1 PCT/JP2007/055333 JP2007055333W WO2007111157A1 WO 2007111157 A1 WO2007111157 A1 WO 2007111157A1 JP 2007055333 W JP2007055333 W JP 2007055333W WO 2007111157 A1 WO2007111157 A1 WO 2007111157A1
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group
hydrogen atom
substituted
iii
formula
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PCT/JP2007/055333
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French (fr)
Inventor
Keizo Kimura
Katsuyoshi Yamakawa
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Fujifilm Corporation
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Publication of WO2007111157A1 publication Critical patent/WO2007111157A1/en

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/045Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/063Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having oxygen or sulfur atom(s) linked directly to the skeleton
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0675Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton

Definitions

  • the invention relates to a near infrared absorbing material.
  • the invention relates to a near infrared absorbing material that plays an important role in optoelectronics-related products such as a near infrared absorbing filter, a near infrared absorbing colored resin composition, a liquid crystal display, an optical card, an optical recording medium and a protective spectacles.
  • the near infrared absorbing material is compatible between light-fastness and other properties.
  • Near infrared absorbing pigments that do not substantially absorb visible light but absorb infrared light have been used in various optoelectronic products such as near infrared absorbing filters. Since these products are depending on their use, exposed to conditions of high temperature, high humidity and light illumination, decomposition of the material often becomes problematic.
  • Japanese Patent Application Laid-Open (JP-A) Nos. 2-4685, 2-43269 and 2-138382 have disclosed technologies for improving durability in these environments by changing the structure of the pigment, such as a naphthalocyanine pigment having a specific structure is excellent in durability.
  • absorption wavelengths of these napththalocyanine pigments are difficult to obtain at the same time as other properties such as solubility thereof.
  • JP-ANo. 11-152412 has disclosed a technology for combining permitting suppression of decomposition of phthalocyanine compounds by light with other properties.
  • JP-A Nos. 10-77360 and 2005-181966 have disclosed technologies for suppressing decomposition by light by using a near infrared absorbing dye and a UV absorbing agent together.
  • the level of suppression is insufficient in these technologies, it has been desired to further improve light fastness and durability of the material.
  • the near infrared absorbing material of the invention comprises (1) at least one compound selected from a singlet oxygen trapping agent, a radical trapping agent and / or an antioxidant and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution.
  • At least one of the compounds in (1) above is preferably represented by Formulae (1-1) or (1-2) below in the near infrared absorbing material of the invention.
  • R 11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom or a hydrolyzable protective group
  • R 12 to R 16 each independently represent a hydrogen atom or a substituent
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 11 may bind to each other to form a ring.
  • R 21 represents a hydrogen atom, an aliphatic group, an acyl group, an alky or arlysulfonyl group, an alky or arlysulfinyl group, an oxy-radical group or a hydroxy group
  • Q represents a group of non-metallic atoms necessary for forming a 5-membered, 6-membered or 7-membered ring
  • R 22 to R 25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to carbon atoms; and R 21 and R 22 , R 22 and R 23 , R 24 and R 25 , or R 21 and R 24 may bind to each other to form a ring.
  • a plurality of compounds in (1) above is preferably contained in the near infrared absorbing material of the invention.
  • At least one compound selected from the group consisting of UV absorbing compounds and fluorescent brightening compounds is also preferably contained in the near infrared absorbing material of the invention.
  • the compound in (3) preferably has a spectroscopic absorption maximum wavelength of 410 nm or shorter in the wavelength region from 270 to 1600 nm in a solution in the near infrared absorbing material of the invention.
  • the compound in (3) is preferably represented by any one of Formulae (HI-I) to (III-9) in the near infrared absorbing material of the invention.
  • R ,386 . to R ,389 and R ,391 to R >400 each independently represent a hydrogen atom or a substituent.
  • R ,3I 5 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.
  • R 379 , R 380 and R 385 each independently represent a substituent.
  • X 341 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.
  • n 379 and n 380 each independently represent an integer from 0 to 4, and plural R 379 and plural R 380 may be the same or different when n 379 and n 3 so are integers of 2 or more.
  • n 385 represents an integer from 0 to 6, and plural R 385 may be the same or different when n 385 is an integer of 2 or more.
  • Adjacent groups may bind to each other to form a ring.
  • the near infrared absorbing material of the invention preferably contains the plural compounds described in (3) above.
  • the spectroscopic absorption maximum wavelength in (2) above is preferably 780 nm or longer in the near infrared absorbing material of the invention.
  • the compound in (2) above is preferably represented by the following Formula (II- 1) in the near infrared absorbing material of the invention.
  • R Z11 to R Z1 ⁇ R ⁇ to R zz ⁇ R Zil to R Zi ⁇ and R Z41 to R /44 each independently represent a hydrogen atom or a substituent, and adjacent groups may bind to
  • M represents two atoms selected from the group consisting of a hydrogen atom and monovalent metal atoms, or M 211 represents a divalent metal atom, or a divalent substituted metal atom group comprising a trivalent or tetravalent metal atom.
  • the invention provides a near infrared absorbing material comprising (1) at least one compound selected from a singlet oxygen trapping agent, a radical trapping agent and / or an antioxidant and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution.
  • the near infrared absorbing material of the invention also preferably contains (3) at least one of UV absorbing agent and fluorescent brightening agent, and the compound preferably has a spectroscopic absorption maximum wavelength of 410 nm or shorter in the wavelength region from 270 to 1600 nm in solution.
  • the spectroscopic absorption maximum wavelength will be described below.
  • the spectroscopic absorption maximum wavelength is defined by the absorption spectrum in the solution.
  • the absorption spectrum may be measured by using any solvents so long as the compound is soluble in the solvent.
  • the solvent may be an organic or inorganic solvent, or water, or may be a mixed solvent thereof. Any solvents and temperatures are available in the invention so long as the spectroscopic absorption maximum wavelength is in the range defined in the invention under any conditions.
  • organic solvent examples include amide solvents (for example N,N-dimethylformamide, N 5 N- dimethylacetamide and l-methyl-2-pyrrolidone), sulfone solvents (for example sulfolane), sulfoxide solvents (for example dimethylsulfoxide), ureido solvents (for example tetramethylurea), ether solvents (for example dioxane, tetrahydrofuran and cyclopentylmethyl ether), ketone solvents (for example acetone and cyclohexanone), hydrocarbon solvents (for example toluene, xylene and n-decane), halogenated hydrocarbon solvents (for example tetrachloroethane, chlorobenzene and chloronaphthalene), alcohol solvents (for example methanol, ethanol, isopropyl alcohol, ethyleneglycol, cyclohexanol and phenol), pyridine solvents (for example
  • amide solvents for measuring the spectroscopic absorption maximum wavelength of the compound defined in (3) above, amide solvents, sulfone solvents, sulfoxide solvents, ureido solvents, ether solvents, ketone solvents, halogenated hydrocarbon solvents, alcohol solvents, ester solvents and nitrile solvents are preferable, and ethyl acetate and N,N-dimethylformamide are particularly preferable.
  • amide solvents, sulfone solvents, sulfoxide solvents, ureido solvents, ether solvents, hydrocarbon solvents, halogenated hydrocarbon solvents, sulfonic acid solvents and sulfuric acid are preferable, and tetrahydrofuran and sulfuric acid are particularly preferable.
  • TJtie concentration of the compound for measuring the spectroscopic absorption maximum wavelength should be a concentration capable of confirming the maximum wavelength of the spectroscopic absorption, and preferably in the range from 1 x 10 "8 to 1 x 10 "2 (mol/1). While the temperature is not particularly restricted, it is preferably in the range from 0 to 8O 0 C, and, provided that the compound is soluble without any problems, most preferably room temperature (25 0 C). [0012]
  • a conventionally used absorption spectrophotometer (for example U-4100 spectrophotometer manufactured by Hitachi High Technologies Corporation) may be used as the measuring apparatus.
  • U-4100 spectrophotometer manufactured by Hitachi High Technologies Corporation may be used as the measuring apparatus.
  • the aliphatic group in the invention refers to an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aralkyl group or a substituted aralkyl group.
  • the alkyl group may be branched, or may be in the form of rings.
  • the number of the carbon atoms in the alkyl group is preferably from 1 to 20, more preferably from 1 to 18.
  • the alkyl moiety of a substituted alkyl group may be from the same groups as the above alkyl group.
  • the alkenyl group may be branched, or may be in the form of rings.
  • the number of the carbon atoms in the alkenyl group is preferably from 2 to 20, more preferably from 2 to 18.
  • the alkenyl moiety of a substituted alkenyl group may be from the same groups as the above alkenyl group.
  • the alkynyl group may be branched or may be in the form of rings.
  • the number of the carbon atoms in the alkynyl group is preferably from 2 to 20, more preferably from 2 to 18.
  • the alkynyl moiety of a substituted alkynyl group may be from the same groups as the above alkynyl group.
  • the alkyl moieties of an aralkyl group and a substituted aralkyl group may be from the same groups as the above alkyl group.
  • the aryl moieties of an aralkyl group and a substituted aralkyl group may be from the same groups as the aryl group described below.
  • the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the alkyl moiety of the substituted aralkyl group include a halogen atom (for example chlorine, bromine or iodine atom); an alkyl group [a linear, branched or cyclic substituted or non-substituted alkyl group, including an alkyl group (preferably an alkyl group having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl or 2-ethylhexyl group); a cycloalkyl group (preferably a substituted or non-substituted cycloalkyl group having 3 to 30 carbon atoms such as cyclohexyl, cyclopentyl or
  • the alkyl group (for example an alkyl group in a thioalkyl group) in the substituents described below represents the alkyl groups of these concepts]; an alkenyl group [a linear, branched or cyclic substituted or non-substituted alkenyl group, including an alkenyl group (an alkenyl group having 2 to 30 carbon atoms; for example vinyl, allyl, prenyl, geranyl or oleyl group); a cycloalkenyl group (preferably a substituted or non-substituted cycloalkenyl group having 3 to 30 carbon atoms, or monovalent group formed by subtracting one hydrogen atom from a cycloalkene having 3 to 30 carbon atoms, for - example 2-cyclopenten-l-yl or 2-cyclohexen-l-yl group); a bicycloalkenyl group (a substituted or non-substituted bicycloalkenyl group, preferably
  • an alkynyl group preferably a substituted or non-substituted alkynyl group having 2 to 30 carbon atoms; for example ethynyl, propargyl or trimethylsilylethynyl group
  • an aryl group preferably a substituted or non-substituted aryl group having 6 to 30 carbon atoms; for example phenyl, p-tolyl, naphthyl, m-chlorophenyl or o-hexadecanoylaminophenyl group
  • a heterocyclic group preferably a 5 or 6-membered, substituted or non-substituted monovalent group formed by subtracting one hydrogen atom from an aromatic or a non-aromatic heterocyclic compound, more preferably a 5- or 6-membered heterocyclic group having 3 to 30
  • an aminocarbonylamino group (preferably a substituted or non-substituted aminocarbonyl group having 1 to 30 carbon atoms; for example carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino or morpholinocarbonylamino group); an alkoxycarbonylamino group (preferably a substituted or non-substituted alkoxycarbonylamino group having 2 to 30 carbon atoms; for example methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino or N-methyl-methoxycarbonylamino group); an aryloxycarbonylamino group (preferably a substituted or non-substituted aryloxycarbonylamino group having 7
  • N-n-octylaminosulfonylamino group an alkyl or arylsulfonylamino group (preferably a substituted or non-substituted alkylsulfonylamino group having 1 to 30 carbon atoms, or a substituted or non-substituted arylsulfonylamino group having 6 to 30 carbon atoms; for example methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3,5-trichlorophenylsulfonylamino or p-methylphenylsulfonylamino group); a mercapto group; [0017] an alkylthio group (preferably a substituted or non-substituted alkylthio group having 1 to 30 carbon atoms; for example methylthio, ethylthio or n-hexadecylthi
  • Functional groups having hydrogen atoms among the above functional groups may be substituted with any of the above groups after removing the hydrogen atoms.
  • Examples of such functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group and an arylsulfonylaminocarbonyl group. Specific examples thereof include methylsulfonylaminocarbonyl group, p-methylphenylsulfonylaminocarbonyl group, acetylaminosulfonyl group and benzoylaminosulfonyl group.
  • Examples of the substituent at the aryl moiety of the substituted aralkyl group include substituents of the following substituted aryl groups.
  • the aromatic group in the invention refers to an aryl group or a substituted aryl group. These aromatic groups may be condensed with the aliphatic groups, other aromatic groups or heterocyclic groups.
  • the aromatic group preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and further preferably 6 to 20 carbon atoms. Phenyl group or naphthyl group that may have substituents is preferable, and phenyl group that may have substituents is particularly preferable among the aryl groups.
  • substituent of the substituted aryl group examples include those described as "substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group".
  • the heterocyclic group of the invention contains at least one heteroatom as ring . constituting atoms.
  • the heterocyclic group may be saturated or unsaturated, may be an aromatic ring, may form a condensed ring with other rings, or may have substituents.
  • the heterocyclic ring is preferably one of 4- to 8-membered rings.
  • the heterocyclic group of the invention preferably contains a saturated or unsaturated 5- or 6-membered heterocyclic group and may be condensed with aliphatic rings, aromatic rings or other heterocyclic rings.
  • Heteroatoms of the heterocyclic ring include B, N, O, S, Se and Te. N, O and S are preferable as the heteroatom of the heterocyclic ring.
  • the carbon atom of the heterocyclic ring preferably has free atomic valence (monovalent: the heterocyclic group is bonded at its carbon atom).
  • the heterocyclic group preferably has 1 to 40 carbon atoms, more preferably 1 to 30 carbon atoms, and further preferably 1 to 20 carbon atoms.
  • Saturated heterocyclic groups include pyrrolidine ring, morpholine ring, 2-bora-l,3-dioxolane ring and 1,3-thiazoline ring.
  • Unsaturated heterocyclic rings include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.
  • the heterocyclic ring may be substituted, and examples of the substituent include those described as "substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group".
  • the near infrared absorbing material of the invention contains at least one compound selected from the singlet oxygen trapping agent, radical trapping agent and / or antioxidant. Any compounds may be available so long as they can trap singlet oxygens or radicals, or prevent oxidation.
  • the compounds include organic nickel compounds such as Seesorb 612 NH (trade name: manufactured by Shipro Kasei Kaisha, Ltd.), Irgastab 2002 (trade name: manufactured by Ciba Specialty Chemicals), hindered amine compounds such as Tinuvin 744 (trade name: manufactured by Ciba Specialty Chemicals), phenol compounds such as irganox 1076 (trade name: manufactured by Ciba Specialty Chemicals), amine compounds such as Sumilizer 9 A (trade name: manufactured by Sumitomo Chemical Co., Ltd.), sulfur compounds such as Sumilizer TPM (trade name: manufactured by Sumitomo Chemical Co., Ltd.), and phosphor compounds such as Sumilizer TPPE (trade name: manufactured by Sumitomo Chemical Co.
  • the compound may be used alone, or a plurality of them may be used together.
  • the compound may be used in combination with a UV absorbing agent to be described below.
  • the total amount of use of the compound in (1) above is preferably from 0.01 to 10 mole relative to 1 mole of the compound defined in (2) above, more preferably from 0.05 to 7 mole, further preferably from 0.1 to 5 mole, and most preferably from 0.1 to 2 mole.
  • the compound in (1) above is preferably represented by the following Formula (1-1) or (1-2):
  • R 11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom or a hydrolyzable protective group
  • R 12 to R each independently represent a hydrogen atom or a substituent
  • R and R , R and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 11 may bind to each other to form a ring.
  • R 21 represents a hydrogen atom, an aliphatic group, an acyl group, an alkyl or aryl sulfonyl group, an alkyl or aryl sulfinyl group, an oxy-radical group or a hydroxy group
  • Q represents a group of non-metallic atoms necessary for forming a 5-, 6- or 7-membered ring
  • R 22 to R 25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom; and R 21 and R 22 , R 22 and R 23 , R 24 and R 25 , or R 21 and R 24 may bind to each other to form a ring.
  • the hydrolyzable protective group of R 11 in Formula (1-1) is preferably represented by a silyl group, a phosphoric acid ester group or a group represented by the following Formula (IV):
  • R 111 represents an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.
  • Y 111 represents a single bond, -O-, -S-, -N(R 112 )-, -C- or a group formed by linking them.
  • R 112 represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded to a carbon atom, an acyl group, or an. alkyl or aryl sulfonyl group.
  • Z 111 represents -CO- or -SO 2 -.
  • R 11 is preferably a hydrogen atom, an aliphatic group having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heterocyclic group bonded to a carbon atom having 2 to 20 carbon atoms, or a hydrolyzable protective group having 1 to 20 carbon atoms; more preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, or a hydrolyzable protective group having 1 to 10 carbon atoms; further preferably a hydrogen atom, an aliphatic group having 1 to 8 carbon atoms, a silyl group having 1 to 10 carbon atoms, a phosphate ester group having 1 to 10 carbon atoms, or a hydrolyzable protective group bonded to a carbonyl group having 1 to 10 carbon atoms; further preferably a hydrogen atom, an aliphatic group having 1 to 4 carbon atoms, a silyl group having 3 to 6 carbon atoms, a phosphate ester group having 2 to
  • Each of R 12 to R 16 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alke ⁇ yl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alky
  • R 21 is preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms, an oxy-radical group or a hydroxy group; more preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acyl group having 2 to 7 carbon atoms, an oxy-radical group or a hydroxy group; further preferably a hydrogen atom, an acetyl group, an oxy-radical group or a hydroxy group; and most preferably a hydrogen atom.
  • Each of R 22 to R 25 is preferably a hydrogen atom or an aliphatic group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, further preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and most preferably all of R 22 to R 25 are methyl groups.
  • Q is preferably a group of non-metallic atoms necessary for forming a 5- to 7-membered ring having at least one oxygen atom, sulfur atom or nitrogen atom in the constituting atoms; more preferably an oxygen atom or a nitrogen atom as a ring-constituting hetero-atom; and further preferably a nitrogen atom.
  • the ring is preferably 5- to 7-membered ring, and 6-membered ring is more preferable.
  • Q forms a piperidine ring.
  • the near infrared absorbing material of the invention comprises at least one compound having spectroscopic absorption maximum wavelength of 700 nm or longer in the range from 400 to 1600 nm in solution.
  • the compound serves as a near infrared absorbing agent and infrared light absorbing agent in the invention.
  • the spectroscopic absorption maximum wavelength is preferably 730 rim or longer, more preferably 760 nm or longer and particularly 780 nm or longer from the viewpoint of insensibility with human eyes, or "invisibility".
  • Examples of the compound having spectroscopic absorption maximum wavelength of 700 nm or longer in the range from 400 to 1600 nm in solution include phthalocyanine compounds, cyanine compounds, squalilium compounds, diimonium compounds, polymethine compounds, azomethine compounds, oxonol compounds, croconium compounds and dithiol metal complex compounds. These compounds are described in JP-A Nos. 2000-281919, 10-180947 and 2003-139946.
  • the phthalocyanine compounds, cyanine compounds, squalilium compounds, diimonium compounds, polymethine compounds, oxonol compounds and croconium compounds are preferable among them; the phthalocyanine compounds, cyanine compounds, diimonium compounds, oxonol compounds and croconium compounds are more preferable among them; the phthalocyanine compounds, diimonium compounds, oxonol compounds and croconium compounds are further preferable among them; the phthalocyanine compounds, diimonium compounds and oxonol compounds are further preferable among them; and the phthalocyanine compounds are most preferable among them. [0039]
  • R 211 to R 214 , R 221 to R 224 , R 231 to R 234 , and R 241 to R 244 each independently represent a hydrogen atom or a substituent, and adjacent groups of these groups may bind to each other to form a ring.
  • M represents two atoms selected from a hydrogen atom and monovalent metal atoms, or M represents a divalent atom or a divalent substituted metal atom group comprising a trivalent or tetravalent metal atom.
  • Examples of the substituents represented by R 211 to R 214 , R 221 to R 224 , R 231 to R 234 , and R 241 to R 244 include the substituent of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group.
  • Examples of the preferable substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonyl group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl
  • R 212 and R 213 , R 222 and R 223 , R 232 and R 233 , and R 242 and R 243 preferably may form condensed benzene rings by being linked to one another.
  • M 211 preferably represents two hydrogen atoms, two Li + , two Na + , two K + , two Rb + , two Cs + and Be 2+ , Mg 2+ , Ca 2+ , Ti 2+ , Mn 2+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Ru 2+ , Rh 2+ , Pd 2+ , Pt 2+ , Ba 2+ , Cd 2+ , Hg 2+ , Pb 2+ , Sn 2+ , Al-Cl, Al-Br, Al-F, Al-I, Ga-Cl, Ga-F, Ga-I, Ga-Br, In-Cl, In-Br, In-I, In-F, Tl-Cl, Tl-Br, Tl-I, Tl-F, Mn-OH, Fe-Cl, Ru-Cl, CrCl 2 , SiCl 2 , SiBr 2 , SiF 2
  • a phthalocyanine compound having a metal at the center can be directly synthesized from corresponding phthalic acid or its derivative (such as acid anhydride, diamide or dinitrile) in the presence of a metal compound.
  • a catalyst for example ammonium molybdate
  • urea are preferably added thereto.
  • the phthalocyanine metal complex can be synthesized using the metal compound as will be described below after the phthalocyanine compound having no metals is synthesized using a lithium compound.
  • the preferable amount of the metal compound is in the range from 0.1 to 10 mole relative to 1 mole of the phthalocyanine containing no metals, more preferably from 0.5 to 5 mole, and further preferably from 1 to 3 mole, when a phthalocyanine containing no metals and a metal compound are used. as the starting materials.
  • Inorganic and organic metal compounds may be used for the metal compound.
  • the metal compound is a halide (for example chloride or bromide), a sulfate, a nitrate, a cyanide, an acetate or an acetylacetonate of a metal, preferably a chloride, a sulfate, a cyanide or an acetate, further preferably a chloride or an acetate, and most preferably an acetate.
  • a halide for example chloride or bromide
  • a sulfate, a nitrate, a cyanide, an acetate or an acetylacetonate of a metal preferably a chloride, a sulfate, a cyanide or an acetate, further preferably a chloride or an acetate, and most preferably an acetate.
  • solvent used in the reaction examples include amide solvents (for example N, N-dimethylformamide, N, N-dimethylacetamide or l-methyl-2-pyrrolidone), sulfone solvents (for example sulfolane), sulfoxide solvent (for example dimethylsulfoxide), ether solvents (for example dioxane or cyclopentylmethyl ether), ketone solvents (for example acetone or cyclohexanone), hydrocarbon solvents (for example toluene or xylene), halogenated hydrocarbon solvents (for example tetrachloroethane or chlorobenzene), alcohol solvents (for example 1-butanol, ethyleneglycol or cyclohexanol) and pyridine solvents (for example pyridine, ⁇ -picoline or 2,6-lutidine).
  • amide solvents for example N, N-dimethylformamide, N, N-dimethylacetamide or l
  • the reaction temperature may be from -30 to 250°C, preferably from 0 to 200°C, more preferably from 20 to 150°C, and further preferably from 50 to 100 0 C.
  • the reaction time may be in the range from 5 minutes to 30 hours.
  • the near infrared absorbing material of the invention preferably contains (3) at least one compound selected from the group consisting of UV absorbing compounds and fluorescent brightening compounds. These compounds preferably have a spectroscopic absorption maximum wavelength of 470 nm or shorter in the wavelength range from 270 to 1600 nm in solution, more preferably 430 nm or shorter, further preferably 410 nm or shorter, and most preferably 380 nm or shorter.
  • the chemical formula is preferably represented by the following Formulae (III-l) to (III-9): [0056]
  • R 311 to R 314 , R 321 to R 366 , R 371 to R 378 , R 381 to R 384 , R 386 to R 389 and R 391 to R 400 each independently represent a hydrogen atom or a substituent.
  • R 315 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.
  • R 379 , R 380 and R 385 each represent a substituent.
  • X 341 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.
  • n 379 and n 38 o each independently represents an integer from 0 to 4, and plural R 379 and R 380 may be the same or different when n. 379 and n 380 are integers of 2 or more. n 38 s represents an integer from 0 to 6, and plural R 385 may be the same or different when n 385 is an integer of 2 or more.
  • the adjacent groups may bind to each other to form a ring.
  • Each ofR 311 to R 314 , R 321 to R 366 , R 371 to R 378 , R 381 to R 384 , R 386 to R 389 and R 391 to R 400 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a
  • Each of R 311 to R 314 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, alkoxy group, an aryloxy group, a silyloxy group, an amino group, an alkylthio group, an arylthio group, an imide group or a silyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a silyloxy group or an amino group; further preferably a hydrogen atom, a halogen atom or an alkyl group; and most preferably a hydrogen atom or a halogen atom.
  • R 315 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group; more preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms; further preferably a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms; further preferably an alkyl group having 1 to 22 carbon atoms or an aryl group having 6 to 22 carbon atoms; further preferably an aryl group having 6 to 20 carbon atoms; and most preferably a 2-hydroxyphenyl group having 6 to 20 carbon atoms.
  • Each of R 321 to R 330 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbam
  • Each of R 331 to R 340 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbam
  • Each of R 341 to R 350 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an alkylthio group, an arylthio group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group or a silyl group; more preferably a hydrogen
  • X 341 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group; further preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; further preferably a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms; further preferably an alkyl group having 1 to 22 carbon atoms or an aryl group having 6 to 22 carbon atoms; and most preferably an alkyl group having 1 to 18 carbon atoms.
  • Each of R 351 to R 360 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a silyl group; and more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an acyloxy group, an amino group, an acylamino group, an arylthio group, an acy
  • Each of R 361 to R 366 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cya ⁇ o group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an alkoxycarbonyl group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group or an.imide group;
  • Each of R 362 , R 363 , R 364 and R 366 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group or a silyl group; more preferably a hydrogen atom, a halogen atom or an alkyl group; and most preferably a hydrogen atom.
  • R 365 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, a
  • Each of R 371 , R 374 , R 375 and R 378 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an amino group or a mercapto group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group or an amino group; and most preferably a hydrogen atom.
  • Each of R 372 , R 373 , R 376 and R 377 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group or a sulfamoyl group; further preferably a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an amino group, a mercapto group or an alkylthio group; and further preferably a hydrogen atom, an alkyl group, an aryl group or an alkoxy group.
  • Each of R 379 and R 380 is more preferably a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; further preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or a heterocyclic thio group; and further preferably a halogen atom, an alkyl group, an aryl group or an alkoxy group.
  • n 379 and n 3 g 0 is preferably from 0 to 3, further preferably from 0 to 2, further preferably 0 or 1, and most preferably 0.
  • R 381 , R 384 , R 386 and R 389 are the same as the range of R 371 .
  • the preferable ranges of R 382 , R 383 R 387 and R 388 are the same as the range of R 372 .
  • R 385 is preferably a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; more preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an amino group, an alkylthio group or an arylthio group; further preferably a halogen atom, an alkyl group, an alkoxy group, an amino group or an alkylthio group; and further preferably a halogen atom or an alkyl group.
  • n 385 is preferably from 0 to 4, further
  • the preferable ranges of R 391 , R 394 , R 397 and R 400 are the same as the range of R 371 .
  • the preferable ranges of R 392 , R 393 R 398 and R 399 are the same as the range of R 372 .
  • R 395 and R 396 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, a hydroxy group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, an amino group, an acylamino group, an alkylthio group or an arylthio group; further preferably a hydrogen atom, a
  • the compound represented by Formulae (DI-I), (III-2), (III-3), (III-4), (111-6), (III-7) or (III-9) is preferable; the compound represented by Formulae (III-l), (III-2), (III-3), (III-6) and (III-7) is further preferable; the compound represented by Formulae (III-l), (III-2), (III-3) or (III-6) is further preferable; the compound represented by Formulae (III-l), (III-2) or (III-6) is further preferable; and the compound represented by Formula (III-l) is most preferable.
  • the compounds can be also appropriately selected from the products such as TINUVIN 109 (trade name) manufactured by Ciba Specialty Chemicals, products such as Whitwefuluor (trade name) manufactured by Sumitomo Chemical Co., Ltd., products such as Hakkol (trade name) manufactured by SHOWA KAGAKU KOGYO CO., LTD., products such as Hostalux (trade name) manufactured by Hoechst, and products such as Kayalight (trade name) manufactured by Nippon Kayaku Co., Ltd.
  • the compounds defined in (1) above in the invention is preferably used in a total amount of 0.1 mole or more relative to 1 mole of the compounds defined in (2) above, more preferably in the range from 0.1 to 2.0 mole, further preferably from 0.1 to 1.0 mole, and most preferably from 0.1 to 0.5 mole.
  • the compounds defined in (3) above in the invention is preferably used in a total amount of 0.1 mole or more relative to 1 mole of the compounds defined in (2) above, more preferably in the range from 0.1 to 2.0 mole, further preferably from 0.1 to 1.0 mole, and most preferably from 0.1 to 0.5 mole.
  • the near infrared absorbing material of the invention can be produced, for example, by the following methods.
  • the near infrared absorbing material of the invention can be used for various applications.
  • the applications include a recording medium for long wavelength laser, a recording medium for invisible printing, an optical filter, a construction and agricultural filter, and painting materials. Applications for the optical filter, construction and agricultural filter, and painting materials are preferable, and applications for the optical filter are more preferable.
  • Example 2 Production of near-infrared absorption filter 100 ml of chloroform was added to 1Og of polystyrene, compound (I) of the structure and the amount shown in Tables 3 to 5, compound (III) of the structure and the amount shown in Tables 31 to 5, and 0.1 g of compound (II) of the structure shown in Tables 3 to 5, and they were dissolved by heating at 4O 0 C with stirring for 15 minutes. The solution was applied onto a glass plate, and was dried in an air stream at room temperature to prepare samples [0108] (Light fastness test)

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Abstract

The invention provides a near infrared absorbing material by which light fastness and other properties are obtainable at the same time. The near infrared absorbing material includes (1) at least one compound selected from a singlet oxygen trapping agent, a radical trapping agent and / or an antioxidant, and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution. In Formula (I-1) and (I-2) of the compound (1), R11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom, or a hydrolyzable protective group; R12 to R16 each independently represent a hydrogen atom or a substituent; R21 represents a hydrogen atom, an aliphatic group, an acyl group, a sulfonyl group, a sulfinyl group, an oxyradical group or a hydroxy group; Q represents a group of non-metallic atoms necessary for forming a 5-, 6- or 7-membered ring; and R22 to R25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom.

Description

DESCRIPTION NEAR INFRARED ABSORBING MATERIAL
Technical Field [0001]
The invention relates to a near infrared absorbing material. In particular, the invention relates to a near infrared absorbing material that plays an important role in optoelectronics-related products such as a near infrared absorbing filter, a near infrared absorbing colored resin composition, a liquid crystal display, an optical card, an optical recording medium and a protective spectacles. The near infrared absorbing material is compatible between light-fastness and other properties.
Background Art [0002]
Near infrared absorbing pigments that do not substantially absorb visible light but absorb infrared light have been used in various optoelectronic products such as near infrared absorbing filters. Since these products are depending on their use, exposed to conditions of high temperature, high humidity and light illumination, decomposition of the material often becomes problematic. Japanese Patent Application Laid-Open (JP-A) Nos. 2-4685, 2-43269 and 2-138382 have disclosed technologies for improving durability in these environments by changing the structure of the pigment, such as a naphthalocyanine pigment having a specific structure is excellent in durability. However, there has been difficulties in that absorption wavelengths of these napththalocyanine pigments are difficult to obtain at the same time as other properties such as solubility thereof. Among these technologies, JP-ANo. 11-152412 has disclosed a technology for combining permitting suppression of decomposition of phthalocyanine compounds by light with other properties. JP-A Nos. 10-77360 and 2005-181966 have disclosed technologies for suppressing decomposition by light by using a near infrared absorbing dye and a UV absorbing agent together. However, since the level of suppression is insufficient in these technologies, it has been desired to further improve light fastness and durability of the material.
Disclosure of Invention [0003]
The near infrared absorbing material of the invention comprises (1) at least one compound selected from a singlet oxygen trapping agent, a radical trapping agent and / or an antioxidant and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution.
At least one of the compounds in (1) above is preferably represented by Formulae (1-1) or (1-2) below in the near infrared absorbing material of the invention. [0004]
Figure imgf000003_0001
Fomula (1-1) Fomula (I-2)
In Formula (1-1), R11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom or a hydrolyzable protective group; R12 to R16 each independently represent a hydrogen atom or a substituent; and R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, or R16 and R11 may bind to each other to form a ring. In Formula (1-2), R21 represents a hydrogen atom, an aliphatic group, an acyl group, an alky or arlysulfonyl group, an alky or arlysulfinyl group, an oxy-radical group or a hydroxy group; Q represents a group of non-metallic atoms necessary for forming a 5-membered, 6-membered or 7-membered ring; R22 to R25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to carbon atoms; and R21 and R22, R22 and R23, R24 and R25, or R21 and R24 may bind to each other to form a ring.
A plurality of compounds in (1) above is preferably contained in the near infrared absorbing material of the invention.
(3) at least one compound selected from the group consisting of UV absorbing compounds and fluorescent brightening compounds is also preferably contained in the near infrared absorbing material of the invention.
The compound in (3) preferably has a spectroscopic absorption maximum wavelength of 410 nm or shorter in the wavelength region from 270 to 1600 nm in a solution in the near infrared absorbing material of the invention.
The compound in (3) is preferably represented by any one of Formulae (HI-I) to (III-9) in the near infrared absorbing material of the invention. [0005]
Figure imgf000004_0001
Formula (HM) Formula (III-2) Formula (III-3)
Figure imgf000004_0002
Formula (III-4) Formula (III-5)
Figure imgf000004_0003
Formula (III-6) Formula (III-7)
Figure imgf000004_0004
Formula (III-8) Formula (III-9)
[0006]
In the Formulae (Ul-I) to (III-9), R ,3J1U1 R r>3i2Z1l to R ,3j66 , T R, 3i7n1 to R ,3*718*, n R3i8M1 to R ,384
R ,386 . to R ,389 and R ,391 to R >400 each independently represent a hydrogen atom or a substituent.
R ,3I5 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom. R379, R380 and R385 each independently represent a substituent. X341 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom. n379 and n380 each independently represent an integer from 0 to 4, and plural R379 and plural R380 may be the same or different when n379 and n3so are integers of 2 or more. n385 represents an integer from 0 to 6, and plural R385 may be the same or different when n385 is an integer of 2 or more. Adjacent groups may bind to each other to form a ring.
The near infrared absorbing material of the invention preferably contains the plural compounds described in (3) above.
The spectroscopic absorption maximum wavelength in (2) above is preferably 780 nm or longer in the near infrared absorbing material of the invention.
The compound in (2) above is preferably represented by the following Formula (II- 1) in the near infrared absorbing material of the invention. [0007]
Figure imgf000005_0001
Formula (11-1)
[0008]
In formula (H-I). RZ11 to RZ1\ R^ to Rzz\ RZil to RZi\ and RZ41 to R/44 each independently represent a hydrogen atom or a substituent, and adjacent groups may bind to
Oi l each other to form a ring. M represents two atoms selected from the group consisting of a hydrogen atom and monovalent metal atoms, or M211 represents a divalent metal atom, or a divalent substituted metal atom group comprising a trivalent or tetravalent metal atom.
Best Mode for Carrying Out the Invention [0009]
Embodiments of the invention will be described in detail hereinafter.
The invention provides a near infrared absorbing material comprising (1) at least one compound selected from a singlet oxygen trapping agent, a radical trapping agent and / or an antioxidant and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution.
The near infrared absorbing material of the invention also preferably contains (3) at least one of UV absorbing agent and fluorescent brightening agent, and the compound preferably has a spectroscopic absorption maximum wavelength of 410 nm or shorter in the wavelength region from 270 to 1600 nm in solution.
[0010] spectroscopic absorption maximum wavelength>
The spectroscopic absorption maximum wavelength will be described below.
The spectroscopic absorption maximum wavelength is defined by the absorption spectrum in the solution. The absorption spectrum may be measured by using any solvents so long as the compound is soluble in the solvent. The solvent may be an organic or inorganic solvent, or water, or may be a mixed solvent thereof. Any solvents and temperatures are available in the invention so long as the spectroscopic absorption maximum wavelength is in the range defined in the invention under any conditions.
Examples of the organic solvent include amide solvents (for example N,N-dimethylformamide, N5N- dimethylacetamide and l-methyl-2-pyrrolidone), sulfone solvents (for example sulfolane), sulfoxide solvents (for example dimethylsulfoxide), ureido solvents (for example tetramethylurea), ether solvents (for example dioxane, tetrahydrofuran and cyclopentylmethyl ether), ketone solvents (for example acetone and cyclohexanone), hydrocarbon solvents (for example toluene, xylene and n-decane), halogenated hydrocarbon solvents (for example tetrachloroethane, chlorobenzene and chloronaphthalene), alcohol solvents (for example methanol, ethanol, isopropyl alcohol, ethyleneglycol, cyclohexanol and phenol), pyridine solvents (for example pyridine, γ-picoline and 2,6-lutidine), ester solvents (for example ethyl acetate and butyl acetate), carboxylic acid solvents (for example acetic acid and propionic acid), nitrile solvents (for example acetonitrile), sulfonic acid solvent (for example methanesulfonic acid), and amine solvents (for example triethylamine and tributylamine). Examples of the inorganic solvent include sulfuric acid and phosphoric acid. [0011]
Among these solvents, for measuring the spectroscopic absorption maximum wavelength of the compound defined in (3) above, amide solvents, sulfone solvents, sulfoxide solvents, ureido solvents, ether solvents, ketone solvents, halogenated hydrocarbon solvents, alcohol solvents, ester solvents and nitrile solvents are preferable, and ethyl acetate and N,N-dimethylformamide are particularly preferable. On the other hand, for measuring the spectroscopic absorption maximum wavelength of the compound defined in (2) above, amide solvents, sulfone solvents, sulfoxide solvents, ureido solvents, ether solvents, hydrocarbon solvents, halogenated hydrocarbon solvents, sulfonic acid solvents and sulfuric acid are preferable, and tetrahydrofuran and sulfuric acid are particularly preferable.
TJtie concentration of the compound for measuring the spectroscopic absorption maximum wavelength should be a concentration capable of confirming the maximum wavelength of the spectroscopic absorption, and preferably in the range from 1 x 10"8 to 1 x 10"2 (mol/1). While the temperature is not particularly restricted, it is preferably in the range from 0 to 8O0C, and, provided that the compound is soluble without any problems, most preferably room temperature (250C). [0012]
A conventionally used absorption spectrophotometer (for example U-4100 spectrophotometer manufactured by Hitachi High Technologies Corporation) may be used as the measuring apparatus. [0013] <Groups in the invention>
Before the descriptions of the compounds, the substituting groups of the invention will be described in detail.
The aliphatic group in the invention refers to an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aralkyl group or a substituted aralkyl group. The alkyl group may be branched, or may be in the form of rings. The number of the carbon atoms in the alkyl group is preferably from 1 to 20, more preferably from 1 to 18. The alkyl moiety of a substituted alkyl group may be from the same groups as the above alkyl group. The alkenyl group may be branched, or may be in the form of rings. The number of the carbon atoms in the alkenyl group is preferably from 2 to 20, more preferably from 2 to 18. The alkenyl moiety of a substituted alkenyl group may be from the same groups as the above alkenyl group. The alkynyl group may be branched or may be in the form of rings. The number of the carbon atoms in the alkynyl group is preferably from 2 to 20, more preferably from 2 to 18. The alkynyl moiety of a substituted alkynyl group may be from the same groups as the above alkynyl group. The alkyl moieties of an aralkyl group and a substituted aralkyl group may be from the same groups as the above alkyl group. The aryl moieties of an aralkyl group and a substituted aralkyl group may be from the same groups as the aryl group described below. [0014]
The substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the alkyl moiety of the substituted aralkyl group include a halogen atom (for example chlorine, bromine or iodine atom); an alkyl group [a linear, branched or cyclic substituted or non-substituted alkyl group, including an alkyl group (preferably an alkyl group having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl or 2-ethylhexyl group); a cycloalkyl group (preferably a substituted or non-substituted cycloalkyl group having 3 to 30 carbon atoms such as cyclohexyl, cyclopentyl or 4-n-dodecylcyclohexyl group); a bicycloalkyl group (preferably a substituted or non-substituted bicycloalkyl group having 5 to 30 carbon atoms, or a monovalent group formed by subtracting one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, for example bicyclo[2.2.1]heptan-2-yl arid bicyclo[2.2.2]octan-3-yl); and a multicyclic alkyl group having three or more cyclic structures, such as tricycloalkyl group. The alkyl group (for example an alkyl group in a thioalkyl group) in the substituents described below represents the alkyl groups of these concepts]; an alkenyl group [a linear, branched or cyclic substituted or non-substituted alkenyl group, including an alkenyl group (an alkenyl group having 2 to 30 carbon atoms; for example vinyl, allyl, prenyl, geranyl or oleyl group); a cycloalkenyl group (preferably a substituted or non-substituted cycloalkenyl group having 3 to 30 carbon atoms, or monovalent group formed by subtracting one hydrogen atom from a cycloalkene having 3 to 30 carbon atoms, for - example 2-cyclopenten-l-yl or 2-cyclohexen-l-yl group); a bicycloalkenyl group (a substituted or non-substituted bicycloalkenyl group, preferably a substituted or non-substituted bicycloalkenly group having 5 to 30 carbon atoms; or a group formed by subtracting one hydrogen atom from a bicycloalkene having one double bond, for example bicyclo[2.2. l]hept-2-en-l-yl or bicyclo[2.2.2]oct-2-en-4-yl group)]; an alkynyl group (preferably a substituted or non-substituted alkynyl group having 2 to 30 carbon atoms; for example ethynyl, propargyl or trimethylsilylethynyl group); [0015] an aryl group (preferably a substituted or non-substituted aryl group having 6 to 30 carbon atoms; for example phenyl, p-tolyl, naphthyl, m-chlorophenyl or o-hexadecanoylaminophenyl group); a heterocyclic group (preferably a 5 or 6-membered, substituted or non-substituted monovalent group formed by subtracting one hydrogen atom from an aromatic or a non-aromatic heterocyclic compound, more preferably a 5- or 6-membered heterocyclic group having 3 to 30 carbon atoms; for example 2-furyl, 2-thienyl, 2-pirimidyl or 2-benzothiazoryl group); a cyano group; a hydroxy group; a nitro group; a carboxy group; an alkoxy group (preferably a substituted or non-substituted alkoxy group having 1 to 30 carbon atoms; for example methoxy, ethoxy, isopropoxy, t-butoxy, n-octyloxy or 2-methoxyethoxy group); an aryloxy group (preferably a substituted or non-substituted aryloxy group having 6 to 30 carbon atoms; for example phenoxy, 2-methylphenoxy, 4-t-butylphenoxy, 3-nitrophenoxy or 2-tetradecanoylaminophenoxy group); a silyoxy group (preferably a silyloxy group having 3 to 20 carbon atoms; for example trimethylsilyoxy or t-butyldimethylsilyloxy group); a heterocyclic oxy group (preferably a substituted or non-substituted heterocyclic oxy group having 2 to 30 carbon atoms; for example l-phenyltetrazol-5-oxy or 2-tetrahydropyranyloxy group); an acyloxy group (preferably a formyloxy group, a substituted or non-substituted alkylcarbonyloxy group having 2 to 30 carbon atoms or a substituted or non-substituted arylcarbonyloxy group having 6 to 30 carbon atoms; for example formyloxy, acetyloxy, pivaloyloxy, stearoyloxy, benzoyloxy or p-methoxyphenylcarbonyloxy group); a carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms; for example N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy, morpholinocarbonyloxy, N,N-di-n-octylaminocarbonyloxy or N-n-octylcarbamoyloxy group); an alkoxycarbonyloxy group (preferably a substituted or non-substituted alkoxycarbonyloxy group having 2 to 30 carbon atoms; for example methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy or n-octylcarbonyloxy group); an aryloxycarbonyloxy group (preferably a substituted or non-substituted aryloxycarbonyloxy group having 7 to 30 carbon atoms; for example phenoxycarbonyloxy, p-methoxyphenoxycarbonyloxy or p-n-hexadecyloxyphenoxycarbonyloxy group) ; [0016] an amino group (preferably amino group, a substituted or non-substituted alkyl amino group having 1 to 30 carbon atoms, or a substituted or non-substituted anilino group having 6 to 30 carbon atoms; for example amino, methylamino, dimethylamino, anilino, N-methylanilino or diphenylamino group); an acylamino group (preferably formylamino group, a substituted or non-substituted alkylcarbonylamino group having 1 to 30 carbon atoms, or an arylcarbonylamino group having 6 to 30 carbon atoms; for example formylamino, acetylamino, pivaloylamino, lauroylamino, benzoylamino or
3,4,5-tri-n-octyloxyphenylcarbonylamino group); an aminocarbonylamino group (preferably a substituted or non-substituted aminocarbonyl group having 1 to 30 carbon atoms; for example carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino or morpholinocarbonylamino group); an alkoxycarbonylamino group (preferably a substituted or non-substituted alkoxycarbonylamino group having 2 to 30 carbon atoms; for example methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino or N-methyl-methoxycarbonylamino group); an aryloxycarbonylamino group (preferably a substituted or non-substituted aryloxycarbonylamino group having 7 to 30 carbon atoms; for example plienoxycarbonylamino, 4-chlorophenoxycarbonylamino or 3-n-octyloxyphenoxy-carbonylamino group); a sulfamoylamino group (preferably a substituted or non-substituted sulfamoylamino group having 0 to 30 carbon atoms; for example sulfamoylamino, N,N-dimethylaminosulfonylamino or
N-n-octylaminosulfonylamino group); an alkyl or arylsulfonylamino group (preferably a substituted or non-substituted alkylsulfonylamino group having 1 to 30 carbon atoms, or a substituted or non-substituted arylsulfonylamino group having 6 to 30 carbon atoms; for example methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3,5-trichlorophenylsulfonylamino or p-methylphenylsulfonylamino group); a mercapto group; [0017] an alkylthio group (preferably a substituted or non-substituted alkylthio group having 1 to 30 carbon atoms; for example methylthio, ethylthio or n-hexadecylthio group); an arylthio group (preferably a substituted or non-substituted arylthio group having 6 to 30 carbon atoms; for example phenythio, p-chlorophenylthio or m-methoxyphenylthio group); a heterocyclic thio group (preferably a substituted or non-substituted heterocyclic thio group having 2 to 30 carbon atoms; for example 2-benzothiazolylthio or l-phenyltetrazol-5-ylthio group); a sulfamoyl group (preferably a substituted or non-substituted sulfamoyl group having 0 to 30 carbon atoms; for example N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl, N,N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl or N-(N'-phenylcarbamoyl)sulfamoyl group); a sulfo group; an alkyl or aryl sulfinyl group (preferably a substituted or non-substituted alkylsulfinyl group having 1 to 30 carbon atoms or a substituted or non-substituted arylsulfinyl group having 6 to 30 carbon atoms; for example methylsulfinyl, ethylsulfinyl, phenylsulfinyl or p-methylphenylsulfinyl group); [0018] an alkyl or arylsulfonyl group (preferably a substituted or non-substituted alkylsulfonyl group having 1 to 30 carbon atoms or a substituted or non-substituted arylsulfonyl group having 6 to 30 carbon atoms; for example methylsulfonyl, ethylsulfonyl, phenylsulfonyl or p-methylsulfonyl group); an acyl group (preferably foraiyl group, a substituted or non-substituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or non-substituted arylcarbonyl group having 7 to 30 carbon atoms, or a substituted or non-substituted heterocyclic carbonyl group having 4 to 30 carbon atoms bonded to the carbonyl group with a carbon atom; for example acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, 4,-n-octyloxyphenylcarbonyl, 2-pyridylcarbonyl or 2-furylcarbonyl group); an aryloxycarbonyl group (preferably a substituted or non-substituted aryloxycarbonyl group having 7 to 30 carbon atoms; for example phenoxycarbonyl, 2-chlorophenoxycarbonyl, 3 -nitrophenoxy carbonyl or 4-t-butylphenoxycarbonyl group); an alkbxycarbonyl group (preferably a substituted or non-substituted alkoxycarbonyl group having 2 to 30 carbon atoms; for example methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, or n-octadecyloxycarbonyl group); a carbamoyl group (preferably a substituted or non-substituted carbamoyl group having 1 to 30 carbon atoms; for example carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N,N-di-n-octylcarbamoyl or N-(methylsulfonyl)carbamoyl group); [0019] an aryl or heterocyclic azo group (preferably a substituted or non-substituted aryl azo group having 6 to 30 carbon atoms, or a substituted or non-substituted heterocyclic azo group having 3 to 30 carbon atoms; for example phenylazo, 4-chlorophenylazo or 5-ethylthio-l,3,4-thiadiazol-2-ylazo); an imide group (preferably N-succimide or N-phthalimide group); a phosphino group (preferably a substituted or non-substituted phosphino group having 2 to 30 carbon atoms; for example dimethylphosphino, diphenylphosphino or methylphenoxyphosphino group); a phosphinyl group (preferably a substituted or non-substituted phosphinyl group having 2 to 30 carbon atoms; for example phosphinyl, dioctyloxyphosphinyl or diethoxyphosphinyl group); a phosphinyloxy group (preferably a substituted or non-substituted phosphinyloxy group having 2 to 30 carbon atoms; for example diphenoxyphosphinyloxy or dioctyloxyphosphinyloxy group); a phosphinylamino group (preferably a substituted or non-substituted phosphinylamino group having 2 to 30 carbon atoms; for example dimethoxyphbsphinylamino or dimethylaminophosphinylamino group); and a silyl group (preferably a substituted or non-substituted silyl group having 3 to 30 carbon atoms; for example trimethylsily, t-butyldimethylsilyl or phenyldimethylsilyl group). [0020]
Functional groups having hydrogen atoms among the above functional groups may be substituted with any of the above groups after removing the hydrogen atoms. Examples of such functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group and an arylsulfonylaminocarbonyl group. Specific examples thereof include methylsulfonylaminocarbonyl group, p-methylphenylsulfonylaminocarbonyl group, acetylaminosulfonyl group and benzoylaminosulfonyl group.
[0021]
Examples of the substituent at the aryl moiety of the substituted aralkyl group include substituents of the following substituted aryl groups. [0022]
The aromatic group in the invention refers to an aryl group or a substituted aryl group. These aromatic groups may be condensed with the aliphatic groups, other aromatic groups or heterocyclic groups. The aromatic group preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and further preferably 6 to 20 carbon atoms. Phenyl group or naphthyl group that may have substituents is preferable, and phenyl group that may have substituents is particularly preferable among the aryl groups.
Examples of the substituent of the substituted aryl group include those described as "substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group". [0023]
The heterocyclic group of the invention contains at least one heteroatom as ring . constituting atoms. The heterocyclic group may be saturated or unsaturated, may be an aromatic ring, may form a condensed ring with other rings, or may have substituents. The heterocyclic ring is preferably one of 4- to 8-membered rings.
The heterocyclic group of the invention preferably contains a saturated or unsaturated 5- or 6-membered heterocyclic group and may be condensed with aliphatic rings, aromatic rings or other heterocyclic rings. Heteroatoms of the heterocyclic ring include B, N, O, S, Se and Te. N, O and S are preferable as the heteroatom of the heterocyclic ring. The carbon atom of the heterocyclic ring preferably has free atomic valence (monovalent: the heterocyclic group is bonded at its carbon atom). The heterocyclic group preferably has 1 to 40 carbon atoms, more preferably 1 to 30 carbon atoms, and further preferably 1 to 20 carbon atoms. Saturated heterocyclic groups include pyrrolidine ring, morpholine ring, 2-bora-l,3-dioxolane ring and 1,3-thiazoline ring. Unsaturated heterocyclic rings include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring. The heterocyclic ring may be substituted, and examples of the substituent include those described as "substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group". [0024]
<Singlet oxygen trapping agent, radical trapping agent and antioxidant
The near infrared absorbing material of the invention contains at least one compound selected from the singlet oxygen trapping agent, radical trapping agent and / or antioxidant. Any compounds may be available so long as they can trap singlet oxygens or radicals, or prevent oxidation. Examples of the compounds include organic nickel compounds such as Seesorb 612 NH (trade name: manufactured by Shipro Kasei Kaisha, Ltd.), Irgastab 2002 (trade name: manufactured by Ciba Specialty Chemicals), hindered amine compounds such as Tinuvin 744 (trade name: manufactured by Ciba Specialty Chemicals), phenol compounds such as irganox 1076 (trade name: manufactured by Ciba Specialty Chemicals), amine compounds such as Sumilizer 9 A (trade name: manufactured by Sumitomo Chemical Co., Ltd.), sulfur compounds such as Sumilizer TPM (trade name: manufactured by Sumitomo Chemical Co., Ltd.), and phosphor compounds such as Sumilizer TPPE (trade name: manufactured by Sumitomo Chemical Co., Ltd.). One of these compounds may be used alone, or a plurality of them may be used together. The compound may be used in combination with a UV absorbing agent to be described below. The total amount of use of the compound in (1) above is preferably from 0.01 to 10 mole relative to 1 mole of the compound defined in (2) above, more preferably from 0.05 to 7 mole, further preferably from 0.1 to 5 mole, and most preferably from 0.1 to 2 mole. [0025]
The compound in (1) above is preferably represented by the following Formula (1-1) or (1-2):
[0026]
Figure imgf000013_0001
Fomula (1-1) Fomula (I-2)
[0027]
In Formula (1-1), R11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom or a hydrolyzable protective group; R12 to R each independently represent a hydrogen atom or a substituent; and R and R , R and R13, R13 and R14, R14 and R15, R15 and R16, or R16 and R11 may bind to each other to form a ring.
In Formula (1-2), R21 represents a hydrogen atom, an aliphatic group, an acyl group, an alkyl or aryl sulfonyl group, an alkyl or aryl sulfinyl group, an oxy-radical group or a hydroxy group; Q represents a group of non-metallic atoms necessary for forming a 5-, 6- or 7-membered ring; R22 to R25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom; and R21 and R22, R22 and R23, R24 and R25, or R21 and R24 may bind to each other to form a ring. [0028]
The hydrolyzable protective group of R11 in Formula (1-1) is preferably represented by a silyl group, a phosphoric acid ester group or a group represented by the following Formula (IV):
Formula (IV)
Figure imgf000014_0001
In the Formula (IV), R111 represents an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom. Y111 represents a single bond, -O-, -S-, -N(R112)-, -C- or a group formed by linking them. R112 represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded to a carbon atom, an acyl group, or an. alkyl or aryl sulfonyl group. Z111 represents -CO- or -SO2-.
R11 is preferably a hydrogen atom, an aliphatic group having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heterocyclic group bonded to a carbon atom having 2 to 20 carbon atoms, or a hydrolyzable protective group having 1 to 20 carbon atoms; more preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, or a hydrolyzable protective group having 1 to 10 carbon atoms; further preferably a hydrogen atom, an aliphatic group having 1 to 8 carbon atoms, a silyl group having 1 to 10 carbon atoms, a phosphate ester group having 1 to 10 carbon atoms, or a hydrolyzable protective group bonded to a carbonyl group having 1 to 10 carbon atoms; further preferably a hydrogen atom, an aliphatic group having 1 to 4 carbon atoms, a silyl group having 3 to 6 carbon atoms, a phosphate ester group having 2 to 8 carbon atoms, or a hydrolyzable protective group bonded to a carbonyl group having 1 to 8 carbon atoms; and further preferably a hydrogen atom, trimethylsilyl group, dimethyl phosphate group, diethyl phosphate group, benzoyl group or acetyl group; and most preferably a hydrogen atom. [0029]
Each of R12 to R16 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkeήyl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, or a silyl group; more preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an alkylthio group, an arylthio group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, or a silyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an acyloxy group, an acylamino group, a carbamoyloxy group, or an alkylthio group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy . group, or an acylamino group; and most preferably a hydrogen atom or an alkyl group. One or both of R and R are preferably tertiary alkyl groups. [0030]
In Formula (1-2), R21 is preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms, an oxy-radical group or a hydroxy group; more preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acyl group having 2 to 7 carbon atoms, an oxy-radical group or a hydroxy group; further preferably a hydrogen atom, an acetyl group, an oxy-radical group or a hydroxy group; and most preferably a hydrogen atom.
Each of R22 to R25 is preferably a hydrogen atom or an aliphatic group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, further preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and most preferably all of R22 to R25 are methyl groups.
Q is preferably a group of non-metallic atoms necessary for forming a 5- to 7-membered ring having at least one oxygen atom, sulfur atom or nitrogen atom in the constituting atoms; more preferably an oxygen atom or a nitrogen atom as a ring-constituting hetero-atom; and further preferably a nitrogen atom. The ring is preferably 5- to 7-membered ring, and 6-membered ring is more preferable. Most preferably, Q forms a piperidine ring. [0031] ,
While specific examples of the compound defined in (1) above are shown below, the invention is by no means restricted to these examples. [0032]
Figure imgf000016_0001
(1-9) (1-1 O)
Figure imgf000016_0002
[0033] (1-1 D (1-12)
Figure imgf000017_0001
(1-13) (1-14)
Figure imgf000017_0002
(1-15) (1-16)
Figure imgf000017_0003
(1-17) (1-18)
Figure imgf000017_0004
(1-19) 1-20)
Figure imgf000017_0005
[0034]
Figure imgf000018_0001
[0035]
(1-31 (1-32)
Figure imgf000019_0001
(1-35)
Figure imgf000019_0002
(1-37) (1-38)
Figure imgf000019_0003
(1-39) (1-40)
Figure imgf000019_0004
[0036]
(1-41) (1-42)
Figure imgf000020_0001
(1-43) (1-44)
Figure imgf000020_0002
(1-45) (1-46)
Figure imgf000020_0003
(1-47) (1-48)
Figure imgf000020_0004
[0037]
These compounds may be synthesized by the methods described in British Patent Nos.1,326,889, 1,354,313 and 1,410,846; USP Nos.3,336,135, 4,268,593, 4,558,131 and 4,584,265; Japanese Patent Application Publication (JP-B) Nos.51-1420 and 52-6523; and JP-ANos.58-114036, 59-5246, 61-73152, 61-86750, 61-90155, 61-90156 and 61-172246, and by modified methods thereof.
[0038] ,
<A Compound having spectroscopic absorption maximum wavelength of 700 nm or longer in the range from 400 to 1600 nm in solution>
The near infrared absorbing material of the invention comprises at least one compound having spectroscopic absorption maximum wavelength of 700 nm or longer in the range from 400 to 1600 nm in solution. The compound serves as a near infrared absorbing agent and infrared light absorbing agent in the invention. The spectroscopic absorption maximum wavelength is preferably 730 rim or longer, more preferably 760 nm or longer and particularly 780 nm or longer from the viewpoint of insensibility with human eyes, or "invisibility".
Examples of the compound having spectroscopic absorption maximum wavelength of 700 nm or longer in the range from 400 to 1600 nm in solution include phthalocyanine compounds, cyanine compounds, squalilium compounds, diimonium compounds, polymethine compounds, azomethine compounds, oxonol compounds, croconium compounds and dithiol metal complex compounds. These compounds are described in JP-A Nos. 2000-281919, 10-180947 and 2003-139946.
The phthalocyanine compounds, cyanine compounds, squalilium compounds, diimonium compounds, polymethine compounds, oxonol compounds and croconium compounds are preferable among them; the phthalocyanine compounds, cyanine compounds, diimonium compounds, oxonol compounds and croconium compounds are more preferable among them; the phthalocyanine compounds, diimonium compounds, oxonol compounds and croconium compounds are further preferable among them; the phthalocyanine compounds, diimonium compounds and oxonol compounds are further preferable among them; and the phthalocyanine compounds are most preferable among them. [0039]
The preferable compounds of these compounds are represented by the following Formula (H-I): [0040]
Figure imgf000022_0001
Formul a ( 1 1 - 1 ) [0041]
In Formula (H-I), R211 to R214, R221 to R224, R231 to R234, and R241 to R244 each independently represent a hydrogen atom or a substituent, and adjacent groups of these groups may bind to each other to form a ring. M represents two atoms selected from a hydrogen atom and monovalent metal atoms, or M represents a divalent atom or a divalent substituted metal atom group comprising a trivalent or tetravalent metal atom. [0042]
Examples of the substituents represented by R211 to R214, R221 to R224, R231 to R234, and R241 to R244 include the substituent of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the alkyl moiety of the substituted aralkyl group. Examples of the preferable substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonyl group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group; more preferably a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonyl group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfϊnyl group, an alkyl or arylsulfonyl group, a carbamoyl group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group; further preferably a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, an amino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, and an alkyl or arylsulfonyl group; further preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, and an arylthio group; further preferably a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and an arylthio group having 6 to 20 carbon atoms; further preferably an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, and an arylthio group having 6 to 10 carbon atoms; further preferably an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 8 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an arylthio group having 6 to 8 carbon atoms; and most preferably an alkoxy group having 1 to 4 carbon atoms.
R212 and R213, R222 and R223, R232 and R233, and R242 and R243 preferably may form condensed benzene rings by being linked to one another. [0043]
M211 preferably represents two hydrogen atoms, two Li+, two Na+, two K+, two Rb+, two Cs+ and Be2+, Mg2+, Ca2+, Ti2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Ru2+, Rh2+, Pd2+, Pt2+, Ba2+, Cd2+, Hg2+, Pb2+, Sn2+, Al-Cl, Al-Br, Al-F, Al-I, Ga-Cl, Ga-F, Ga-I, Ga-Br, In-Cl, In-Br, In-I, In-F, Tl-Cl, Tl-Br, Tl-I, Tl-F, Mn-OH, Fe-Cl, Ru-Cl, CrCl2, SiCl2, SiBr2, SiF2, SiI2, ZrCl2, GeCl2, GeBr2, GeI2, GeF2, SnCl2, SnBr2, SnI2, SnF2, TiCl2, TiBr2, TiF2, Si(OH)2, Ge(OH)2, Zr(OH)2, Mn(OH)2, Sn(OH)2, TiR2, CrR2, SiR2, SnR2, GeR2, Si(OR)2, Sn(OR)2, Ge(OR)2, Ti(OR)2, Cr(OR)2, Sn(SR)2, Ge(SR)2 (R represents an aliphatic group or aromatic group), VO, MnO and TiO; more preferably two hydrogen atoms, two Li+, two Na+, two K+, two Rb+ and Be2+, Mg2+, Ca2+, Ti2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Ru2+, Rh2+, Pd2+, Pt2+, Ba2+, Sn2+, Al-Cl, Al-Br, Ga-Cl, Ga-F, Ga-I, Ga-Br, In-Cl, In-Br, Tl-Cl, Tl-Br, Mn-OH, Fe-Cl, Ru-Cl, CrCl2, SiCl2, SiBr2, ZrCl2, GeCl2, GeBr2, SnCl2, SnBr2, TiCl2, TiBr2, Si(OH)2, Ge(OH)2, Zr(OH)2, Mn(OH)2, Sn(OH)2, TiR2, CrR2, SiR2, SnR2, GeR2, Si(OR)2, Sn(OR)2, Ge(OR)2, Ti(OR)2, Cr(OR)2, Sn(SR)2, Ge(SR)2 (R represents an aliphatic group or aromatic group), VO, MnO and TiO; and further preferably two hydrogen atoms, two Li+, two Na+, two K+, and Be2+, Mg2+, Ca2+, Ti2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Ru2+, Rh2+, Pd2+, Pt2+, Ba2+, Sn2+, Al-Cl, Ga-Cl, In-Cl, Tl-Cl, Mn-OH, Fe-Cl, Ru-Cl, CrCl2, SiCl2, ZrCl2, GeCl2, TiCl2, Si(OH)2, Ge(OH)2, Zr(OH)2, Mn(OH)2, TiR2, CrR2, SiR2, GeR2, Si(OR)2, Ge(OR)2, Ti(OR)2, Cr(OR)2, (R represents an aliphatic group or aromatic group), VO, MnO and TiO. M211 further preferably represents two hydrogen atoms, Mn2+, VO, Zn2+ or Cu2+; and most preferably VO, Zn2+ or Cu2+. [0044]
While specific examples of the compound defined by (2) above are shown below, the invention is by no means restricted to these examples. [0045]
Figure imgf000025_0001
[0046]
Figure imgf000026_0001
[0047]
Figure imgf000027_0001
[0048]
Figure imgf000028_0001
R=OC2H5
Figure imgf000028_0002
[0049]
Figure imgf000029_0001
Figure imgf000030_0001
[0051]
Figure imgf000031_0001
[0052]
Figure imgf000032_0001
( H -73) ( E -74)
Figure imgf000032_0002
( E -75) ( E -76)
Figure imgf000032_0003
[0053]
The above-described compounds can be readily synthesized according to the method described in Chemistry A: European Journal, vol 9, 5123-5134 (2003), or by the modified methods of the above method. For example, a phthalocyanine compound having a metal at the center can be directly synthesized from corresponding phthalic acid or its derivative (such as acid anhydride, diamide or dinitrile) in the presence of a metal compound. When a phthalocyanine compound is synthesized, a catalyst (for example ammonium molybdate) and urea are preferably added thereto. Otherwise, the phthalocyanine metal complex can be synthesized using the metal compound as will be described below after the phthalocyanine compound having no metals is synthesized using a lithium compound. The latter method is more preferable for synthesizing the phthalocyanine metal complex. Specifically, the preferable amount of the metal compound is in the range from 0.1 to 10 mole relative to 1 mole of the phthalocyanine containing no metals, more preferably from 0.5 to 5 mole, and further preferably from 1 to 3 mole, when a phthalocyanine containing no metals and a metal compound are used. as the starting materials. Inorganic and organic metal compounds may be used for the metal compound. For example, the metal compound is a halide (for example chloride or bromide), a sulfate, a nitrate, a cyanide, an acetate or an acetylacetonate of a metal, preferably a chloride, a sulfate, a cyanide or an acetate, further preferably a chloride or an acetate, and most preferably an acetate. [0054]
Examples of the solvent used in the reaction include amide solvents (for example N, N-dimethylformamide, N, N-dimethylacetamide or l-methyl-2-pyrrolidone), sulfone solvents (for example sulfolane), sulfoxide solvent (for example dimethylsulfoxide), ether solvents (for example dioxane or cyclopentylmethyl ether), ketone solvents (for example acetone or cyclohexanone), hydrocarbon solvents (for example toluene or xylene), halogenated hydrocarbon solvents (for example tetrachloroethane or chlorobenzene), alcohol solvents (for example 1-butanol, ethyleneglycol or cyclohexanol) and pyridine solvents (for example pyridine, γ-picoline or 2,6-lutidine). One of these solvents may be used alone, or a mixture of plural of them may be used. Of these solvents, amide solvents, sulfone solvents, ether solvents, hydrocarbon solvents, halogenated hydrocarbon solvents and pyridine solvents are preferable; sulfone solvents, ether solvents, hydrocarbon solvents and halogenated hydrocarbon solvents are more preferable; ether solvents, hydrocarbon solvents and halogenated hydrocarbon solvents are further preferable; halogenated hydrocarbon solvents are further preferable; and chlorobenzene is most preferable. The reaction temperature may be from -30 to 250°C, preferably from 0 to 200°C, more preferably from 20 to 150°C, and further preferably from 50 to 1000C. The reaction time may be in the range from 5 minutes to 30 hours. [0055] <UV absorbing agents and fluorescent brightening agents>
The near infrared absorbing material of the invention preferably contains (3) at least one compound selected from the group consisting of UV absorbing compounds and fluorescent brightening compounds. These compounds preferably have a spectroscopic absorption maximum wavelength of 470 nm or shorter in the wavelength range from 270 to 1600 nm in solution, more preferably 430 nm or shorter, further preferably 410 nm or shorter, and most preferably 380 nm or shorter. The chemical formula is preferably represented by the following Formulae (III-l) to (III-9): [0056]
The compound represented by Formulae (III-l) to (III-9) will be described below: [0057]
Figure imgf000034_0001
Formula (111-1) Formula (111-2) Formula (III-3)
Figure imgf000034_0002
Formula (III-4) Formula (IM-S)
Figure imgf000034_0003
Formula (III-6) Formula (III-7)
,
,
Figure imgf000034_0004
Formula (III-8) Formula (III-9)
[0058]
R311 to R314, R321 to R366, R371 to R378, R381 to R384, R386 to R389 and R391 to R400 each independently represent a hydrogen atom or a substituent. R315 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom. R379, R380 and R385 each represent a substituent. X341 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom. n379 and n38o each independently represents an integer from 0 to 4, and plural R379 and R380 may be the same or different when n.379 and n380 are integers of 2 or more. n38s represents an integer from 0 to 6, and plural R385 may be the same or different when n385 is an integer of 2 or more.
The adjacent groups may bind to each other to form a ring. [0059]
Examples of the substituent represented by R311 to R314, R321 to R366, R371 to R378, R 3si tQ R 384 } R 386 tø R 389 ^ R 39i tø R 4oo indude substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the alkyl moiety of the aralkyl group above.
Each ofR311 to R314, R321 to R366, R371 to R378, R381 to R384, R386 to R389 and R391 to R400 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group or a silyl group. [0060]
Each of R311 to R314 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, alkoxy group, an aryloxy group, a silyloxy group, an amino group, an alkylthio group, an arylthio group, an imide group or a silyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a silyloxy group or an amino group; further preferably a hydrogen atom, a halogen atom or an alkyl group; and most preferably a hydrogen atom or a halogen atom. [0061]
R315 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group; more preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms; further preferably a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms; further preferably an alkyl group having 1 to 22 carbon atoms or an aryl group having 6 to 22 carbon atoms; further preferably an aryl group having 6 to 20 carbon atoms; and most preferably a 2-hydroxyphenyl group having 6 to 20 carbon atoms. [0062]
Each of R321 to R330 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group or a silyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an acylamino group, an alkyl or arylsulfonylamino group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a carbamoyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group, an acyloxy group, an acylamino group, an acyl group, an alkoxycarbonyl group or a carbamoyl group; and further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group, an acylamino group or an alkoxycarbonyl group. R321 is most preferably a hydroxy group. [0063]
Each of R331 to R340 is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cyano group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group or a silyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an acylamino group, an alkyl or an arylsulfonylamino group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a carbamoyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group, an acyloxy group, an acylamino group, an acyl group, an alkoxycarbonyl group or a carbamoyl group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group, an acylamino group or an alkoxycarbonyl group. R331 is most preferably a hydroxy group. [0064]
Each of R341 to R350 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an alkylthio group, an arylthio group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group or a silyl group; more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an amino group, an acylamino group, an alkylthio group or an arylthio group; further preferably a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group or an acylamino group; and most preferably a hydrogen atom, an alkoxy group or an amino group. [0065]
X341 is preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group; further preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; further preferably a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms; further preferably an alkyl group having 1 to 22 carbon atoms or an aryl group having 6 to 22 carbon atoms; and most preferably an alkyl group having 1 to 18 carbon atoms. [0066]
Each of R351 to R360 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a sulfamoyl group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a silyl group; and more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an acyloxy group, an amino group, an acylamino group, an arylthio group, an acyl group, an aryloxycarbonyl group, or an alkoxycarbonyl group. R351 is most preferably a hydroxy group. [0067]
Each of R361 to R366 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyaήo group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an alkoxycarbonyl group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group or an.imide group; more preferably a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonyl group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, or an alkyl or arylsulfonylamino group; and further preferably an alkyl group, an aryl group, a heterocyclic group, an alkoxycarbonyl group or an acylamino group. [0068]
Each of R362, R363, R364 and R366 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group or a silyl group; more preferably a hydrogen atom, a halogen atom or an alkyl group; and most preferably a hydrogen atom.
On the other hand, R365 is further preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group or a silyl group; further preferably a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, or an alkyl or arylsulfonylamino group; and further preferably a heterocyclic group, an amino group or an acylamino group. [0069]
Each of R371, R374, R375 and R378 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an amino group or a mercapto group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group or an amino group; and most preferably a hydrogen atom. [0070]
Each of R372, R373, R376 and R377 is more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group or a sulfamoyl group; further preferably a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an amino group, a mercapto group or an alkylthio group; and further preferably a hydrogen atom, an alkyl group, an aryl group or an alkoxy group. [0071]
Each of R379 and R380 is more preferably a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; further preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or a heterocyclic thio group; and further preferably a halogen atom, an alkyl group, an aryl group or an alkoxy group.
Each of n379 and n3g0 is preferably from 0 to 3, further preferably from 0 to 2, further preferably 0 or 1, and most preferably 0. [0072]
The preferable ranges of R381, R384, R386 and R389 are the same as the range of R371. The preferable ranges of R382, R383 R387 and R388 are the same as the range of R372.
R385 is preferably a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; more preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an amino group, an alkylthio group or an arylthio group; further preferably a halogen atom, an alkyl group, an alkoxy group, an amino group or an alkylthio group; and further preferably a halogen atom or an alkyl group. n385 is preferably from 0 to 4, further preferably from 0 to 2, further preferably 0 or 1, and most preferably 0. [0073]
The preferable ranges of R391, R394, R397 and R400 are the same as the range of R371. The preferable ranges of R392, R393 R398 and R399 are the same as the range of R372.
Each of R395 and R396 is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, a hydroxy group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a silyloxy group, an amino group, an acylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group or a silyl group; more preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, an amino group, an acylamino group, an alkylthio group or an arylthio group; further preferably a hydrogen atom, a halogen atom, an alkyl group, a cyano group, an alkoxy group or an amino group; and further preferably a hydrogen atom or an alkyl group. [0074]
Of the compounds represented by Formulae (III- 1 ) to (III-9), the compound represented by Formulae (DI-I), (III-2), (III-3), (III-4), (111-6), (III-7) or (III-9) is preferable; the compound represented by Formulae (III-l), (III-2), (III-3), (III-6) and (III-7) is further preferable; the compound represented by Formulae (III-l), (III-2), (III-3) or (III-6) is further preferable; the compound represented by Formulae (III-l), (III-2) or (III-6) is further preferable; and the compound represented by Formula (III-l) is most preferable. [0075]
While compounds (III-l) to (III-l 65) are shown as specific examples of the compounds defined in (3) above, the invention is by no means restricted to these examples. [0076]
Figure imgf000041_0001
[0077]
Figure imgf000042_0001
(m-15) (m-i 6)
Figure imgf000042_0002
(m-i 9) (1-20)
Figure imgf000042_0003
[0078]
Figure imgf000043_0001
[0079]
Figure imgf000044_0001
[0080]
Figure imgf000045_0001
Figure imgf000046_0001
. (πi-53) (1-54)
Figure imgf000046_0002
(πi-59) (1-60)
Figure imgf000046_0003
[0082]
Figure imgf000047_0001
[0083]
Figure imgf000048_0001
[0084]
Figure imgf000049_0001
(m-87) (m-88)
Figure imgf000049_0002
(m-89) (m-9 o)
Figure imgf000049_0003
[0085]
Figure imgf000050_0001
(m-93) (m-94)
Figure imgf000050_0002
(m-95) (m-96)
Figure imgf000050_0003
(m-97)
Figure imgf000050_0004
(m-99)
(m-i oo)
Figure imgf000050_0005
[0086]
Figure imgf000051_0001
[0087]
Figure imgf000052_0001
[0088]
Figure imgf000053_0001
[0090]
(1-131)
Figure imgf000054_0001
(IH- 132)
Figure imgf000054_0002
(1-133)
Figure imgf000054_0003
(m-134)
Figure imgf000054_0004
(BI- 135)
Figure imgf000054_0005
[0091]
(IH- 136)
Figure imgf000055_0001
Figure imgf000055_0002
(M- 138)
Figure imgf000055_0003
(M-139)
Figure imgf000055_0004
Figure imgf000055_0005
[0092]
(M-I 41)
Figure imgf000056_0001
(iπ-142)
Figure imgf000056_0002
(m-144)
Figure imgf000056_0003
(m-145)
Figure imgf000056_0004
93]
(IH- 146)
Figure imgf000057_0001
(IH- 147)
Figure imgf000057_0002
(M- 148)
Figure imgf000057_0003
(M-I 49)
Figure imgf000057_0004
Figure imgf000058_0001
(m-154)
Figure imgf000058_0002
(m-155)
Figure imgf000058_0003
[0095]
Figure imgf000059_0001
[0096]
(M- 1 6 1 )
Figure imgf000060_0001
Figure imgf000060_0002
(1- 1 6 3 )
Figure imgf000060_0003
(m- 1 6 4 )
Figure imgf000060_0004
(M- I 6 5 )
Figure imgf000060_0005
[0097]
These compounds can be readily synthesized by the methods described in JP-B No. 50-25337, USP No. 3,785,827, JP-ANo. 5-4449, JP-B No. 48-30492, JP-ANo. 2-188573, EP 0684278A1 and Journal of Organic Chemistry, Vol. 23, pl344 (1958), and by modified methods thereof. The compounds can be also appropriately selected from the products such as TINUVIN 109 (trade name) manufactured by Ciba Specialty Chemicals, products such as Whitwefuluor (trade name) manufactured by Sumitomo Chemical Co., Ltd., products such as Hakkol (trade name) manufactured by SHOWA KAGAKU KOGYO CO., LTD., products such as Hostalux (trade name) manufactured by Hoechst, and products such as Kayalight (trade name) manufactured by Nippon Kayaku Co., Ltd. [0098] <Contents of the compounds in the near infrared absorbing material of the invention> The compounds defined in (1) above in the invention is preferably used in a total amount of 0.1 mole or more relative to 1 mole of the compounds defined in (2) above, more preferably in the range from 0.1 to 2.0 mole, further preferably from 0.1 to 1.0 mole, and most preferably from 0.1 to 0.5 mole.
The compounds defined in (3) above in the invention is preferably used in a total amount of 0.1 mole or more relative to 1 mole of the compounds defined in (2) above, more preferably in the range from 0.1 to 2.0 mole, further preferably from 0.1 to 1.0 mole, and most preferably from 0.1 to 0.5 mole. [0099] <A Method for producing the near infrared absorbing material of the invention>
The near infrared absorbing material of the invention can be produced, for example, by the following methods.
[1] The compounds defined in (1) above, the compounds defined in (2) above and the compounds defined in (3) above are dissolved or dispersed in a solvent (for example chloroform, methylene chloride, toluene, acetone, methylethyl ketone, cyclohexane, ethyl acetate, dibutyl ether, tetraliydrofuran or dimethylformamide).
[2] The compounds defined in (1) above, the compounds defined in (2) above and the compounds defined in (3) above are heated and kneaded with a resin (for example ABS resin, polyethylene resin, polypropylene resin, polyvinyl chloride resin, polycarbonate resin, polystyrene resin, polyacrylonitrile resin, methacrylonitrile resin, polymethacrylate ester resin or polyester resin).
[3] The compounds defined in (1) above, the compounds defined in (2) above and the compounds defined in (3) above are dissolved or dispersed in the above solvent, the above-described resin is added to the solution and dissolved by heating, and the solution is formed into a film or directly solidified.
[4] The compounds defined in (1) above, the compounds defined in (2) above and the compounds defined in (3) above are dissolved or dispersed in the above solvent, and the solution is applied or hard-coated on a paper sheet, resin sheet, resin, film, glass or metal plate.
[5] Monomers are directly added to the mixture of the compounds defined in (1) above, the compounds defined in (2) above and the compounds defined in (3) above, or the monomers are added to a finely pulverized mixture or a solution of the compounds, and the mixture of the monomers and the compounds is polymerized. [0100] <Applications of the near infrared absorbing material of the invention>
The near infrared absorbing material of the invention can be used for various applications. The applications include a recording medium for long wavelength laser, a recording medium for invisible printing, an optical filter, a construction and agricultural filter, and painting materials. Applications for the optical filter, construction and agricultural filter, and painting materials are preferable, and applications for the optical filter are more preferable. [0101]
Since light fastness is obtained at the same time as other properties in the near infrared absorbing material, it may be used for novel application fields.
The disclosure of Japanese Patent Application No. 2006-092127 is incorporated herein by reference in its entirety. Examples [0102]
While the invention is described in more detail with reference to examples, the invention is by no means restricted to these examples.
The compound defined in (1) is referred to compound (I), the compound defined in (2) is referred to compound (II), and the compound defined in (3) is referred to compound (III) for the convenience of descriptions. [0103] Example 1 (Production of near infrared absorption filter)
100ml of chloroform was added to 1Og of polystyrene, compound (I) of the structure and the amount shown in Tables 1 and 2, compound (III) of the structure and the amount shown in Tables 1 and 2, and 0.1 g of compound (II- 1) , and they were dissolved by heating at 40°C with stirring for 15 minutes. The solution was applied onto a glass plate, and was dried in an air stream at room temperature to prepare samples. (Light fastness test)
The samples obtained above were irradiated with light from a xenon lamp at a luminous energy of 9.5 x 104 lux for three days, and to evaluate light fastness the ratio of residual compound (II- 1) relative to that before irradiating was determined by measuring the optical density at the spectroscopic absorption maximum wavelength. [0104] Table 1
Figure imgf000063_0001
[0105]
Figure imgf000064_0001
[0106]
As shown in Tables 1 and 2, the samples of the invention showed good light fastness, and the effect of the invention is remarkable. [0107] Example 2 (Production of near-infrared absorption filter) 100 ml of chloroform was added to 1Og of polystyrene, compound (I) of the structure and the amount shown in Tables 3 to 5, compound (III) of the structure and the amount shown in Tables 31 to 5, and 0.1 g of compound (II) of the structure shown in Tables 3 to 5, and they were dissolved by heating at 4O0C with stirring for 15 minutes. The solution was applied onto a glass plate, and was dried in an air stream at room temperature to prepare samples [0108] (Light fastness test)
The samples obtained above were irradiated with a xenon lamp at a luminous energy of 9.5 x lO4 lux for three days, and to evaluate light fastness the ratio of residual compound (II) relative to that before irradiated was determined by measuring the optical density at the spectroscopic absorption maximum wavelength. [0109]
Table 3
Figure imgf000066_0001
[0110]
Table 4
Figure imgf000067_0001
[OHl] Table 5
Figure imgf000068_0001
[0112]
As shown in Tables 3 to 5, the results obtained by variously changing the samples of the invention also showed good light fastness, and the effect of the invention is remarkable. [0113]
Physical properties of the compounds used in the examples of the invention are shown below: [0114] Table 6
Figure imgf000069_0001
[0115] Table 7
Figure imgf000069_0002

Claims

1. A near infrared absorbing material comprising (1) at least one compound selected from singlet oxygen trapping agents, radical trapping agents and / or antioxidants, and (2) at least one compound having a spectroscopic absorption maximum wavelength of 700 nm or longer in a wavelength region from 400 to 1600 nm in solution.
2. The near infrared absorbing material of claim 1, wherein at least one of the compounds in (1) above is a compound represented by Formulae (1-1) or (1-2):
Figure imgf000070_0001
Fomula (M) Fomula (I-2) wherein, in the Formulae (1-1) and (1-2), R11 represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded to a carbon atom, or a hydrolyzable protective group; R12 to R16 each independently represent a hydrogen atom or a substituent; R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16,or R16 and R11 may bind to each other form a ring, R21 represents a hydrogen atom, an aliphatic group, an acyl group, a sulfonyl group, a sulfinyl group, an oxyradical group or a hydroxy group; Q represents a group of non-metallic atoms necessary for forming a 5-, 6- or 7-membered ring; R22 to R25 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom; and R and R , R and R , R and R , or R and R24 may bind to each other to form a ring.
3. The near infrared absorbing material of claim 1 comprising plural compounds in (1) above.
4. The near infrared absorbing material of claim 1 further comprising (3) at least one compound selected from the group consisting of UV absorbing compounds and fluorescent brightening compounds.
5. The near infrared absorbing material of claim 4, wherein the compound in (3) above has a spectroscopic absorption maximum wavelength of 410 nm or shorter in the wavelength range from 270 to 1600 nm in solution.
6. The near infrared absorbing material of claim 4, wherein the compound in (3) above is represented by any one of Formulae (III- 1 ) to (III- 9);
Figure imgf000071_0001
Formula (111-1) Formula (III-2) Formula (III-3)
Figure imgf000071_0002
Formula (III-4) Formula (III-5)
Figure imgf000071_0003
Formula (III-6) Formula (III-7)
Figure imgf000071_0004
Formula (HI-S) Formula (III-9) wherein, in the formulae (III-l) to (III-9), R >331111 u t.o_ τ Ri3'1144, τ R>3i2Z1l to R366, R371 to R378, R38Ho R384, R386 to R389, and R391 to R400 each independently represent a hydrogen atom or a substituent; R315 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom; R379, R380 and R385 each independently represent a substituent; X represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded to a carbon atom; n379 and n380 each independently represent an integer from 0 to 4; plural R379 and R380 may be the same or different when n379 and n380 are integers of 2 or more; n385 represents an integer from 0 to 6; plural R385 may be the same or different when n385 is an integer of 2 or more; and adjacent groups may bind to each other to form a ring.
7. The near infrared absorbing material of Claim 4 comprises a plurality of compounds in (3) above.
8. The near infrared absorbing material of Claim 1, wherein the spectroscopic absorption maximum wavelength of the compound in (2) above is 780 nm or longer.
9. The near infrared absorbing material of Claim 1, wherein the compound in (2) above is represented by Formula (II- 1):
Figure imgf000072_0001
Formula (11-1) wherein, in Formula (II-l), R211 to R214, R221 to R224, R231 to R234, and R241 to R244 each independently represent a hydrogen atom or substituent; adjacent groups of these groups may bind to each other to form a ring; and M211 represents two atoms selected from a group consisting of a hydrogen atom and monovalent metal atoms, or M211 represents a divalent metal atom, or a divalent substituted metal atom group comprising a trivalent or tetravalent metal atom.
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EP2093258A3 (en) * 2008-02-13 2010-09-29 FUJIFILM Corporation Infrared dye composition, infrared ray absorbing ink and electrophotographic toner
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US11357713B2 (en) 2015-07-14 2022-06-14 Conopco, Inc. Antimicrobial composition

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07178861A (en) * 1993-12-24 1995-07-18 Mitsui Toatsu Chem Inc Near infrared-absorbing panel
JPH083870A (en) * 1994-06-13 1996-01-09 Japan Carlit Co Ltd:The Infrared-absorbing processed textile product and processing thereof
JPH0827371A (en) * 1994-05-09 1996-01-30 Japan Carlit Co Ltd:The Ultraviolet/infrared-absorbing resin composition
JPH11231126A (en) * 1997-11-18 1999-08-27 Toyobo Co Ltd Ir absorbing filter
JP2001133624A (en) * 1999-11-05 2001-05-18 Sumitomo Osaka Cement Co Ltd Near-ir shielding film
JP2003114323A (en) * 2001-10-04 2003-04-18 Bridgestone Corp Near infarared ray absorbing film
JP2003268312A (en) * 2002-03-15 2003-09-25 Shin Etsu Polymer Co Ltd Near-infrared ray schielding component and method for manufacturing the same
JP2004361525A (en) * 2003-06-03 2004-12-24 Dainippon Printing Co Ltd Optical filter and display using the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07178861A (en) * 1993-12-24 1995-07-18 Mitsui Toatsu Chem Inc Near infrared-absorbing panel
JPH0827371A (en) * 1994-05-09 1996-01-30 Japan Carlit Co Ltd:The Ultraviolet/infrared-absorbing resin composition
JPH083870A (en) * 1994-06-13 1996-01-09 Japan Carlit Co Ltd:The Infrared-absorbing processed textile product and processing thereof
JPH11231126A (en) * 1997-11-18 1999-08-27 Toyobo Co Ltd Ir absorbing filter
JP2001133624A (en) * 1999-11-05 2001-05-18 Sumitomo Osaka Cement Co Ltd Near-ir shielding film
JP2003114323A (en) * 2001-10-04 2003-04-18 Bridgestone Corp Near infarared ray absorbing film
JP2003268312A (en) * 2002-03-15 2003-09-25 Shin Etsu Polymer Co Ltd Near-infrared ray schielding component and method for manufacturing the same
JP2004361525A (en) * 2003-06-03 2004-12-24 Dainippon Printing Co Ltd Optical filter and display using the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2993197A1 (en) * 2006-11-29 2016-03-09 Sun Chemical Corporation Phthalocyanine colorants and their use as fluorescent security taggants
EP2093258A3 (en) * 2008-02-13 2010-09-29 FUJIFILM Corporation Infrared dye composition, infrared ray absorbing ink and electrophotographic toner
US11357713B2 (en) 2015-07-14 2022-06-14 Conopco, Inc. Antimicrobial composition

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