WO2014208514A1 - Composé phtalocyanine, colorant absorbant les rayons infrarouges proches, et matériau absorbant les rayons infrarouges proches - Google Patents

Composé phtalocyanine, colorant absorbant les rayons infrarouges proches, et matériau absorbant les rayons infrarouges proches Download PDF

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WO2014208514A1
WO2014208514A1 PCT/JP2014/066604 JP2014066604W WO2014208514A1 WO 2014208514 A1 WO2014208514 A1 WO 2014208514A1 JP 2014066604 W JP2014066604 W JP 2014066604W WO 2014208514 A1 WO2014208514 A1 WO 2014208514A1
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substituent
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悟史 林
陽介 真鍋
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山田化学工業株式会社
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Priority to JP2015524045A priority Critical patent/JP6339073B2/ja
Priority to KR1020157028091A priority patent/KR102232999B1/ko
Publication of WO2014208514A1 publication Critical patent/WO2014208514A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines

Definitions

  • the present invention relates to a novel phthalocyanine compound having an absorptivity in the near infrared region and a method for producing the same.
  • Patent Document 1 discloses a phthalocyanine compound having a specific structure as a compound having an absorption maximum in the near infrared region.
  • compounds having absorption ability in the near infrared region are required to have further light resistance and solubility.
  • An object of the present invention is to provide a phthalocyanine compound having absorptivity in the near-infrared wavelength region of 750 to 1200 nm, having excellent light resistance and solubility, a production method thereof, and a use of the compound.
  • the present inventors have succeeded in developing a novel phthalocyanine compound having a specific structure, and the phthalocyanine compound has excellent light resistance and solubility, and is a problem of the present invention. I found out that it can be solved.
  • the present invention has been completed based on such findings.
  • R 1 and R 2 are the same or different and may have an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, or a substituent.
  • Alkylthio group, arylthio group optionally having substituent, heteroaryloxy group optionally having substituent, heteroarylthio group optionally having substituent, NR 3 R 4 group or halogen X 1 and X 2 are the same or different and each represents an oxygen atom or a sulfur atom, and A 1 and A 2 are the same or different and each represents an aromatic ring which may have a substituent.
  • R 1 is an NR 3 R 4 group or an aryloxy group which may have a substituent
  • R 2 is an NR 3 R 4 group, an aryloxy group which may have a substituent or an arylthio group which may have a substituent
  • R 3 and R 4 may be the same or different and each may have a hydrogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, or a substituent.
  • An arylalkyl group, X 1 and X 2 are both oxygen atoms, Item 3.
  • the compound according to Item 1 or 2 wherein A 1 and A 2 are both a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.
  • R 1 and R 2 are the same or different and may have an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, or a substituent.
  • Alkylthio group, arylthio group optionally having substituent, heteroaryloxy group optionally having substituent, heteroarylthio group optionally having substituent, NR 3 R 4 group or halogen X 1 and X 2 are the same or different and each represents an oxygen atom or a sulfur atom, and A 1 and A 2 are the same or different and each represents an aromatic ring which may have a substituent.
  • R 3 and R 4 are the same or different and each is a hydrogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, or a hetero that may have a substituent.
  • An aryl group or an ant optionally having a substituent It shows the Ruarukiru group.
  • R 1 and R 2 are the same or different and may have an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, or a substituent.
  • Alkylthio group, arylthio group optionally having substituent, heteroaryloxy group optionally having substituent, heteroarylthio group optionally having substituent, NR 3 R 4 group or halogen X 1 and X 2 are the same or different and each represents an oxygen atom or a sulfur atom, and A 1 and A 2 are the same or different and each represents an aromatic ring which may have a substituent.
  • R 3 and R 4 are the same or different and each is a hydrogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, or a hetero that may have a substituent.
  • An aryl group or an ant optionally having a substituent It shows the Ruarukiru group.
  • Item 8. A phthalocyanine compound produced by the method according to Item 5.
  • Item 12. A heat shielding material comprising the phthalocyanine compound according to any one of Items 1 to 4.
  • Item 13 Item 5. A heat ray absorbing material containing the phthalocyanine compound according to any one of Items 1 to 4.
  • the novel phthalocyanine compound of the present invention has an absorption ability in the near-infrared absorption region of 750 to 1200 nm and is excellent in light resistance and solubility. Therefore, the novel phthalocyanine compound is useful as a near-infrared absorber. In use, it can be suitably used.
  • Phthalocyanine Compound The phthalocyanine compound of the present invention is a compound represented by the following general formula (1).
  • R 1 and R 2 may be the same or different and each may have an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, or a substituent.
  • a good alkylthio group, an arylthio group which may have a substituent, a heteroaryloxy group which may have a substituent, a heteroarylthio group which may have a substituent, an NR 3 R 4 group or X 1 and X 2 are the same or different and each represents an oxygen atom or a sulfur atom, and A 1 and A 2 are the same or different and each may have a substituent.
  • the phthalocyanine compound represented by the above general formula (1) is a novel compound not described in any literature, has an absorptivity in the near infrared wavelength region of 750 to 1200 nm, and has light resistance and solubility (particularly, solubility in an organic solvent). It is a compound useful as a near-infrared absorber because of its excellent properties, solubility in resins (compatibility) and the like.
  • the phthalocyanine compound of the present invention comprises at least one kind represented by the following general formulas (1a) to (1d).
  • Examples of the alkoxy group represented by R 1 and R 2 include, for example, a linear chain having 1 to 12 carbon atoms, a branched chain having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms bonded to an oxygen atom. Groups.
  • n- means normal
  • s- means secondary (sec-)
  • t- means tertiary (tert-).
  • Examples of the aryloxy group represented by R 1 and R 2 include a group in which a monocyclic or polycyclic (for example, bicyclic or tricyclic) aryl group is bonded to an oxygen atom.
  • Specific examples include a phenoxy group, a naphthoxy group, an anthryloxy group, a phenanthrenyloxy group, a fluorenyloxy group, and a pyrenyloxy group.
  • a group in which a monocyclic or bicyclic aryl group is bonded to an oxygen atom is preferable.
  • Particularly preferred are a phenoxy group, a 1-naphthoxy group (1-naphthyloxy group) and a 2-naphthoxy group (2-naphthyloxy group).
  • alkylthio group represented by R 1 and R 2 for example, a linear chain having 1 to 12 carbon atoms, a branched chain having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms is bonded to a sulfur atom. Groups.
  • Particularly preferred is a group in which a linear alkyl group having 1 to 8 carbon atoms, a branched chain having 3 to 8 carbon atoms, or a cyclic alkyl group having 3 to 8 carbon atoms is bonded to a sulfur atom.
  • Examples of the arylthio group represented by R 1 and R 2 include a group in which a monocyclic or polycyclic (for example, bicyclic or tricyclic) aryl group is bonded to a sulfur atom.
  • Specific examples include a phenylthio group, a naphthylthio group, an anthrylthio group, and a pyrenylthio group.
  • a group in which a monocyclic or bicyclic aryl group is bonded to a sulfur atom is preferable.
  • Particularly preferred are a phenylthio group and a naphthylthio group.
  • Examples of the heteroaryloxy group represented by R 1 and R 2 include a group in which a monocyclic or polycyclic (eg, bicyclic or tricyclic) heteroaryl group is bonded to an oxygen atom.
  • Specific examples include groups in which a pyridyl group, a pyrimidine group, an indolyl group, a quinoline group, a benzimidazole group, a furanyl group, a thienyl group, a benzofuran group, a 1,3,4-thiadiazole group, and the like are bonded to an oxygen atom. it can.
  • a group in which a monocyclic or bicyclic heteroaryl group is bonded to an oxygen atom is preferable.
  • heteroarylthio group represented by R 1 and R 2 examples include a group in which a monocyclic or polycyclic (for example, bicyclic or tricyclic) heteroaryl group is bonded to a sulfur atom.
  • Specific examples include groups in which a pyridyl group, a pyrimidine group, an indolyl group, a quinoline group, a benzimidazole group, a furanyl group, a thienyl group, a benzofuran group, a 1,3,4-thiadiazole group, etc. are bonded to a sulfur atom.
  • a group in which a monocyclic or bicyclic heteroaryl group is bonded to a sulfur atom is preferable.
  • R 1 and R 2 described above are the same or different and are each an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a heteroaryloxy group, or a heteroarylthio group, these groups each have a substituent. You may have.
  • Substituents on the alkyl chain, aryl ring or heteroaryl ring of the alkoxy group, aryloxy group, alkylthio group, arylthio group, heteroaryloxy group or heteroarylthio group (on the alkyl chain, aryl ring or heteroaryl ring)
  • Examples of the group that can be substituted include an alkyl group, a haloalkyl group, an alkoxy group, a hydroxyalkyl group, an alkylthio group, an alkylamino group, a dialkylamino group, a cyclic amino group, a halogen atom, an acyl group, an alkoxycarbonyl group, and a ureido group.
  • the substituent may have 1 to 5 substituents on the alkyl chain, aryl ring or heteroaryl ring in R 1 and R 2 .
  • alkyl group examples include straight chain having 1 to 12 carbon atoms, branched chain having 3 to 12 carbon atoms, and cyclic alkyl group having 3 to 12 carbon atoms.
  • Preferred is a straight chain having 1 to 8 carbon atoms, a branched chain having 3 to 8 carbon atoms, or a cyclic alkyl group having 3 to 8 carbon atoms, particularly preferably a methyl group, an ethyl group, an n-propyl group, or isopropyl.
  • haloalkyl group examples include haloalkyl groups having 1 to 6 carbon atoms. Specifically, chloromethyl group, dichloromethyl group, trichloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, trifluoroethyl group, pentafluorobutyl group, nonafluorobutyl group, undecafluoropentyl group And a tridecafluorohexyl group.
  • alkoxy group examples include an alkoxy group having 1 to 8 carbon atoms. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, n-pentoxy group, isopentoxy group, neopentoxy group, n Examples include -hexyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, t-octyloxy group and the like.
  • hydroxyalkyl group examples include hydroxyalkyl groups having 1 to 8 carbon atoms. Specifically, hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, 4-hydroxybutyl group, 5-hydroxypentyl group, 6-hydroxyhexyl group, 7-hydroxyheptyl group, 8-hydroxyoctyl group Etc.
  • alkylthio group examples include thioalkoxy groups having 1 to 8 carbon atoms. Specifically, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, s-butylthio group, t-butylthio group, n-pentylthio group, isopentylthio group, neo A pentylthio group, n-hexylthio group, cyclohexylthio group, n-heptylthio group, n-octylthio group, 2-ethylhexylthio group, t-octylthio group and the like can be mentioned.
  • alkylamino group examples include an amino group substituted with a linear chain having 1 to 12 carbon atoms, a branched chain having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms.
  • alkyl group of the alkylamino group specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2 -Methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group,
  • dialkylamino group examples include, for example, amino groups which are the same or different and are substituted by a linear chain having 1 to 12 carbon atoms, a branched chain having 3 to 12 carbon atoms, or two cyclic alkyl groups having 3 to 12 carbon atoms. It is done.
  • alkyl group of the dialkylamino group include the same alkyl groups as those described above as the alkyl group of the alkylamino group.
  • cyclic amino group examples include cyclic amines in which two substituents on the nitrogen atom form a ring structure together with the nitrogen atom and may contain N, O, and S heteroatoms as ring constituent atoms. It is done. Specific examples include pyrrolidyl group, piperidino group, piperazino group, morpholino group, thiomorpholino group and the like.
  • the cyclic amino group is preferably a 5- to 8-membered cyclic amino group.
  • halogen atom examples include fluorine, chlorine, bromine and iodine.
  • acyl group examples include an acetyl group, an ethylcarbonyl group, a pivaloyl group, and a benzoyl group.
  • the alkylcarbamoyl group is represented by —CON (R 5 ) 2 .
  • R 5 s are the same or different and each represents a hydrogen atom, a straight chain having 1 to 12 carbon atoms, a branched chain having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms.
  • Examples of the alkyl group include the same alkyl groups as those described above as the alkyl group of the alkylamino group.
  • Specific examples include a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, a dimethylcarbamoyl group, a diethylcarbamoyl group, and a dipropylcarbamoyl group.
  • arylsulfonyl group examples include a sulfonyl group substituted with an aryl group having 6 to 12 carbon atoms. Specific examples include a phenylsulfonyl group and a naphthylsulfonyl group.
  • cyclic amino group examples include the same cyclic amino groups as those exemplified as the group that can be substituted on the alkyl chain, aryl ring or heteroaryl ring in R 1 and R 2 .
  • they are a straight chain having 1 to 8 carbon atoms, a branched chain having 3 to 8 carbon atoms, or a cyclic alkyl group having 3 to 8 carbon atoms, and a cyclic amino group having 5 to 8 members.
  • Examples of the aryl group represented by R 3 and R 4 in the NR 3 R 4 group represented by R 1 and R 2 include monocyclic and polycyclic (for example, bicyclic or tricyclic) aryl groups. . Specific examples include a phenyl group, a naphthyl group, and an anthryl group. A monocyclic or bicyclic aryl group is preferable, and a phenyl group and a naphthyl group are particularly preferable.
  • it is an alkyl group in which one of hydrogen atoms of an alkyl group having 1 to 3 carbon atoms is substituted with a monocyclic or bicyclic aryl group, and particularly preferably a benzyl group, a phenylethyl group, or a naphthylethyl group. is there.
  • alkyl group having a substituent examples include 2-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,3,3,3-pentafluoropropyl group, benzyl group, phenethyl group, Examples thereof include 2-phenylethyl group, 3-phenylethyl group, 4-hydroxybutyl group, 2-methoxyethyl group, 3-methoxypropyl group, 2-isopropoxyethyl group, and butanoic acid ethyl group.
  • Examples of the NR 3 R 4 group represented by R 1 and R 2 include a secondary or tertiary amino group. Specifically, n-propylamino group, isopropylamino group, n-butylamino group, n-pentylamino group, n-hexylamino group, cyclohexylamino group, n-heptylamino group, n-octylamino group, 2 -Ethylhexylamino group, phenylamino group, 1-naphthylamino group, 2-naphthylamino group, benzylamino group, 1-phenylethylamino group, 2-phenylethylamino group, 1- (p-tolyl) ethylamino group, ⁇ , ⁇ -dimethylbenzylamino group, 1-naphthylethylamino group, 1,1-diphenylmethylamino group
  • halogen atom represented by R 1 and R 2 examples include fluorine, chlorine, bromine and iodine.
  • Examples of the aromatic ring represented by A 1 and A 2 include monocyclic and polycyclic (eg, bicyclic or tricyclic) aromatic rings. Specific examples include benzene (ring), naphthalene (ring), anthracene (ring), phenanthrene (ring), and the like. Preferably, it is a monocyclic or bicyclic aromatic ring, more preferably a benzene ring or a naphthalene ring, and particularly preferably a benzene ring. As will be described later, each of these aromatic rings may have a substituent.
  • the aromatic rings represented by A 1 and A 2 described above each may have a substituent.
  • substituents include alkyl groups, haloalkyl groups, alkoxy groups, hydroxyalkyl groups, alkylthio groups, alkylamino groups, dialkylamino groups, cyclic amino groups, halogen atoms, acyl groups, alkoxycarbonyl groups, ureido groups, and sulfamoyl groups.
  • Examples of the divalent metal represented by M include metal atoms belonging to Groups 3 to 15 of the periodic table. Specific examples include Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, and Pb.
  • Examples of the trivalent or tetravalent metal compound represented by M include halides, hydroxides and oxides of metals belonging to Groups 3 to 15 of the periodic table. Specifically, AlCl, AlOH, InCl, FeCl , MnOH, SiCl 2, SnCl 2, GeCl 2, Si (OH) 2, Si (OCH 3) 2, Si (OPh) 2, Si (OSiCH 3) 2, Sn (OH) 2 , Ge (OH) 2 , VO, TiO, etc. can be mentioned. In addition, said Ph shows a phenyl group.
  • X 1 and X 2 it is preferable that at least one is an oxygen atom, X 1 and X 2 are both oxygen atoms It is more preferable that As the R 1, is preferably NR 3 R 4 group or an optionally substituted aryl group, examples of R 2, NR 3 R 4 group, which may have a substituent A good aryloxy group or an arylthio group which may have a substituent is preferable. As the R 1 and R 2, it is preferable that at least one of which is NR 3 R 4 group, and more preferably R 1 is NR 3 R 4 group.
  • R 3 and R 4 groups are the same or different and each has a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • An arylalkyl group that may be present is preferable.
  • R 1 to R 4 R 1 is an NR 3 R 4 group, and one of R 3 and R 4 is a hydrogen atom, and the other is an alkyl group (for example, When R 1 is an NR 3 R 4 group, and R 3 is a hydrogen atom and R 4 is an alkyl group, the solubility is more excellent, which is particularly preferable.
  • a 1 and A 2 are each preferably a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.
  • M is preferably Cu, Zn, Co, Ni, Pd, Pb, MnOH, AlCl, FeCl, InCl, SnCl 2 , VO or TiO, and more preferably VO or Cu.
  • the phthalocyanine compound of the present invention is produced by reacting compound (2) with a metal or an inorganic or organometallic compound in the presence of a base, as shown in the following reaction formula-1. Can do.
  • the above compound (2) is also a novel compound not described in the literature, and is a useful substance that can be a raw material for producing the phthalocyanine compound of the present invention.
  • the method for producing the compound will be described in “3. Intermediate for producing phthalocyanine compound and method for producing the same” below.
  • Examples of the metal to be reacted with the compound (2) include metals belonging to Groups 3 to 15 of the periodic table. Specific examples include Al, Si, Ti, V, Mn, Fe, Co, Ni, Cu, Zn, Ge, Ru, Rh, Pd, In, Sn, Pt, and Pb.
  • Examples of the inorganic metal compound include halides, carboxylates, sulfates, nitrates, oxides and complexes of the above metals.
  • organometallic compound examples include carbonyl compounds of the above metals. Specific examples include manganese acetylacetone.
  • the amount of the metal or inorganic or organic metal compound used is usually 0.2 mol or more, preferably 0.25 to 0.5 mol, per 1 mol of compound (2).
  • Examples of the base include metal alkoxide, diazabicycloundecene, diazabicyclononene and the like.
  • metal alkoxide examples include sodium or potassium methoxide, ethoxide, propoxide, butoxide, pentoxide and the like.
  • tBuOK sodium-t-butoxide
  • tBuOK potassium-t-butoxide
  • the base is generally used in an amount of about 1 to 3 mol, preferably about 1.2 to 1.8 mol, per 1 mol of compound (2).
  • formamide ammonia, urea or the like
  • a nitrogen source if necessary.
  • it is formamide.
  • the reaction of the compound (2) with a metal or inorganic or organic metal compound is usually performed in a solvent.
  • a solvent known solvents can be widely used as long as they are inert to the reaction. Examples include aromatic hydrocarbons, halogenated hydrocarbons, ethers, alcohols, amines, amides, sulfoxides, nitriles, nitrobenzene, and the like.
  • aromatic hydrocarbons include xylene and methylnaphthalene.
  • halogenated hydrocarbons include chlorobenzene, o-dichlorobenzene, trichlorobenzene, chloronaphthalene, tetrachloroethylene, and trichloroethylene.
  • ethers include diethylene glycol dimethyl ether.
  • alcohols include n-propanol, isopropanol, n-butanol, isobutanol, s-butanol, t-butanol, n-hexanol (sometimes referred to as 1-hexanol), n-amyl alcohol, Cyclohexanol, 2-methyl-1-pentanol, 1-heptanol, 2-heptanol, 1-octanol (sometimes referred to as n-octanol), 2-ethylhexanol, benzyl alcohol, ethanediol, propylene glycol, methoxyethanol Ethoxyethanol, propoxyethanol, butoxyethanol, dimethylaminoethanol, diethylaminoethanol and the like.
  • amines include tri-n-butylamine.
  • amides include N, N-dimethylformamide (hereinafter sometimes referred to as DMF), N, N-dimethylacetamide (hereinafter also referred to as DMA), N-methylpyrrolidone (hereinafter referred to as DMA). And NMP), 1,3-dimethylimidazolidinone and the like.
  • DMF N, N-dimethylformamide
  • DMA N, N-dimethylacetamide
  • DMA N-methylpyrrolidone
  • NMP 1,3-dimethylimidazolidinone and the like.
  • sulfoxides include sulfolane and dimethyl sulfoxide (hereinafter sometimes referred to as DMSO).
  • nitriles examples include benzonitrile.
  • solvents are used singly or in combination of two or more.
  • Preferred are n-amyl alcohol, n-hexanol, 1-heptanol, and 1-octanol.
  • the amount of these solvents to be used may be appropriately set depending on the kind of the compound to be used and the like. Usually, about 1 to 100 parts by weight, preferably about 2 to 30 parts by weight is used with respect to 1 part by weight of the compound (2). Is done.
  • the reaction time varies depending on the type of raw material compound and the reaction temperature and cannot be generally specified, but is usually about 1 to 24 hours.
  • the compound obtained by the above reaction can be separated from the reaction system by a normal separation means and further purified.
  • known separation and purification means can be widely used, and examples thereof include a recrystallization method, a solvent extraction method, column chromatography, gel chromatography, preparative chromatography, etc.
  • a phthalocyanine compound can be obtained efficiently and with high purity also by a conventionally known method such as filtration, washing or drying.
  • reaction formula-2 As shown in the above reaction formula-2, first, compound (5) (tetrafluorophthalonitrile) is reacted with compound (a) to produce compound (4) (step 1). Next, the compound (4) obtained in the step 1 is reacted with the compound (b) to be converted into the compound (3) (step 2). Furthermore, the compound (2) can be produced by reacting the obtained compound (3) with the compound (c) (step 3).
  • Compound (4) is usually produced by reacting compound (5) with compound (a) in the presence of a base in a solvent.
  • a base for example, known methods disclosed in Japanese Patent Application Laid-Open Nos. 01-045474 and 08-120186 can be used, and the details are as follows.
  • Examples of the compound (a) include alcohols, phenols, naphthols, thiols, thiophenols, amines (primary amines or secondary amines), and the like. Specifically, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-pentanol, n-hexanol, cyclohexanol, n-heptanol, n-octanol, 2-ethylhexanol , T-octanol, phenol, 2-methylphenol (o-cresol), 3-methylphenol, 4-methylphenol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2, 6-dimethylphenol, 2,3,5-trimethylphenol, 2,3,6-trimethylphenol, 2,4,5-trimethylphenol, 2,4,6-trimethylphenol, 2-ethyl
  • the amount of compound (a) to be used is generally about 0.9 to 2 equivalents, preferably about 0.9 to 1.5 equivalents, more preferably about 0.95 to 1.1 equivalents relative to compound (5). is there.
  • Examples of the base used in this reaction include alkaline substances. Specific examples include potassium fluoride, potassium carbonate, potassium hydroxide, sodium hydroxide and the like. These bases are used individually by 1 type or in mixture of 2 or more types. Preferred are potassium fluoride and potassium carbonate.
  • the amount of such base used is appropriately set according to the type of base used and the amount used, but is generally 0.9 to 3 equivalents, preferably 1 with respect to compound (5). It may be about 2 equivalents, more preferably about 1 to 1.3 equivalents.
  • MEK methyl ethyl ketone
  • the amount of these solvents to be used may be appropriately set depending on the kind of base to be used and the like, but is usually about 1 to 50 parts by weight, preferably about 1 to 20 parts by weight with respect to 1 part by weight of compound (5) More preferably, about 1.5 to 15 parts by weight may be used.
  • This reaction is usually performed at ⁇ 10 to 40 ° C., preferably ⁇ 5 to 15 ° C.
  • reaction time varies depending on the type of base used, reaction temperature, etc., and cannot be generally stated, but the reaction is usually completed in about 1 to 12 hours.
  • Examples of the compound (b) include biphenols, binaphthols, and bianthracenols. Specifically, 2,2′-biphenol, 1,1′-bi-2-naphthol (2,2′-dihydroxy-1,1′-binaphthyl), 3,3 ′, 5,5′-tetra- tert-butyl-2,2′-biphenol, 5,5 ′, 6,6 ′, 7,7 ′, 8,8′-octahydro-1,1′-bi-2-naphthol, 3,3 ′, 5 , 5′-tetramethyl-2,2′-dihydroxybiphenyl, and the like.
  • 2,2'-biphenol 3,3 ', 5,5'-tetramethyl-2,2'-dihydroxybiphenyl, and 2,2'-dihydroxy-1,1'-binaphthyl At least one of them.
  • the amount of such a base used is appropriately set according to the type of compound used and the amount used, but is usually 1 to 10 equivalents, preferably 1 to 8 with respect to compound (4). Equivalent, more preferably about 1.2 to 3.5 equivalents.
  • solvents can be widely used as long as they are inert to the reaction, but acetone, acetonitrile, DMSO, DMA, DMF, MEK, etc. are used. Is desirable.
  • the amount of the solvent used may be appropriately set depending on the type of the compound used and the like, but is usually about 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 1 part by weight of the compound (4). About 1 to 20 parts by weight, more preferably about 1 to 20 parts by weight.
  • This reaction is usually carried out at about 20 to 100 ° C, preferably 20 to 85 ° C.
  • the compound obtained by the above reaction can be separated from the reaction system by a normal separation means and further purified.
  • a normal separation means for example, the means described above in “2. Method for producing phthalocyanine compound” can be applied.
  • Process 3 Compound (2) is usually produced by reacting compound (3) with compound (c) in a solvent in the presence of a base.
  • Examples of the compound (c) include alcohols, phenols, naphthols, thiols, thiophenols, amines (primary amines or secondary amines), and the like. Specifically, the same compounds as the compounds mentioned as the compound (a) can be mentioned.
  • the amount of compound (c) to be used is generally about 1 to 5 equivalents, preferably about 1 to 3.5 equivalents, more preferably about 1.05 to 3 equivalents relative to compound (3).
  • the inorganic base examples include alkali metal carbonates, alkali metal hydroxides, alkali metal hydrides and the like.
  • an organic base examples include an amine etc. are mentioned, for example.
  • alkali metal carbonate examples include sodium carbonate, potassium carbonate, and sodium bicarbonate.
  • alkali metal hydroxide examples include sodium hydroxide and potassium hydroxide.
  • alkali metal hydride examples include sodium hydride and potassium hydride.
  • bases are used singly or in combination of two or more.
  • they are triethylamine and potassium carbonate.
  • the amount of the base used is appropriately set according to the type of compound to be used and the amount used, but is usually 1 to 10 equivalents, preferably 1 to 8 equivalents, relative to compound (3). More preferably, it may be about 1.1 to 3.5 equivalents.
  • the amount of the solvent used may be appropriately set depending on the type of the compound to be used and the like, but is usually about 0.5 to 50 parts by weight, preferably 0.5 to 30 parts per 1 part by weight of the compound (3). About part by weight, more preferably about 0.8 to 20 parts by weight may be used.
  • the compound obtained by the above reaction can be separated from the reaction system by a normal separation means and further purified.
  • a normal separation means for example, the means described above in “2. Method for producing phthalocyanine compound” can be applied.
  • intermediate compound (2 ′) for producing a phthalocyanine compound obtained by the above reaction (in the above compound (2), R 1 is NR 3 R 4 , and R 3 is a hydrogen atom) Can be converted into the intermediate compound (2 ′′) by the method shown in the following reaction scheme-3.
  • R 6 has an alkyl group which may have a substituent and a substituent.
  • Compound (2 ′′) is usually produced by reacting compound (2 ′) with compound (d) in a solvent in the presence of a base.
  • R 6 in the compound (d) is an alkyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or a substituent.
  • arylalkyl group which may have an alkyl group which may have a substituent in the above R 3 and R 4, an aryl group which may have a substituent, and a substituent, respectively. Examples thereof include the same heteroaryl group which may be substituted, and the same arylalkyl group which may have a substituent.
  • Examples of the leaving group for Y in the compound (d) include a halogen atom, a p-toluenesulfonyl group, a methanesulfonyl group, and a trifluoromethanesulfonyl group.
  • halogen atoms include chlorine, bromine and iodine.
  • the compound (d) include benzyl chloride, bromomethane, bromoethane, 1-bromopropane, 2-bromopropane, 1-bromobutane (hereinafter sometimes referred to as n-BuBr), 2-bromobutane, -Bromo-2-methylpropane, t-butylbromide, 1-bromopentane, 1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, bromocyclopentane, 1-bromohexane 2-bromohexane, 3-bromohexane, 1-bromo-4-methylpentane, 1-bromo-2-ethylbutane, bromocyclohexane, 1-bromoheptane, 2-bromoheptane, 3-bromoheptane, 1-bromooctane , 2-bromooctane
  • the amount of compound (d) to be used is generally about 0.9 to 3 equivalents, preferably about 1 to 2.5 equivalents, more preferably about 1.2 to 2 equivalents, relative to compound (2 ').
  • the base used in this reaction known inorganic bases and organic bases can be used.
  • the same base as mentioned in the above (Step 2) can be used.
  • the amount of the base used is appropriately set according to the type of compound used and the amount used, but is usually 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to compound (2 ′). More preferably, it may be about 1.2 to 2.5 equivalents.
  • aprotic polar solvents that are inert to the reaction can be widely used.
  • DMF, DMA, DMSO, etc. can be mentioned.
  • the amount of the solvent used may be appropriately set depending on the kind of the compound to be used and the like, but is usually about 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 1 part by weight of the compound (2 ′). About 1 part, more preferably about 1 to 20 parts by weight may be used.
  • This reaction is usually performed at about 50 to 140 ° C., preferably 60 to 120 ° C.
  • the reaction time varies depending on the type of compound used, the reaction temperature, and the like, and cannot be generally specified, but the reaction is usually completed in about 1 to 12 hours.
  • the compound obtained by the above reaction can be separated from the reaction system by a normal separation means and further purified.
  • a normal separation means for example, the means described above in “2. Method for producing phthalocyanine compound” can be applied.
  • the phthalocyanine compound of the present invention has an absorption ability in the near-infrared wavelength region of 750 to 1200 nm, it can be used as a near-infrared absorbing dye. That is, the near-infrared absorbing dye of the present invention comprises the phthalocyanine compound of the present invention.
  • the phthalocyanine compound of the present invention has an absorptivity in the near-infrared wavelength region of 750 to 1200 nm, it is a near-infrared absorbing material, more specifically, a near-infrared absorbing filter, protective glasses, agricultural film, heat ray It can be used for blocking filters, light receiving elements, long wavelength laser compatible optical recording media, anti-counterfeiting printing inks, camouflage coatings, and the like. That is, the near-infrared absorbing material of the present invention contains the phthalocyanine compound of the present invention.
  • the phthalocyanine compound of the present invention is applied as it is or together with a binder resin or additive to paper, a plastic sheet, a plastic film, glass, a resin, or the like, hard-coated, or mixed with a monomer to be polymerized. Therefore, it can be used for various applications as a near-infrared absorbing material.
  • the binder resin is not particularly limited, and examples thereof include a homopolymer or copolymer of an acrylic acid monomer, a cellulose polymer, a vinyl polymer, a condensation polymer, a rubber thermoplastic polymer, and a photopolymerizable compound. Examples include coalescence.
  • acrylic monomer examples include acrylic acid, methacrylic acid, acrylic ester, and methacrylic ester.
  • vinyl polymer examples include polystyrene, vinyl chloride-vinyl acetate copolymer, polyvinyl pyrrolidone, polyvinyl butyral, and polyvinyl alcohol.
  • condensation polymer examples include polyester and polyamide.
  • rubber-based thermoplastic polymers include butadiene-styrene copolymers.
  • photopolymerizable compound examples include an epoxy compound.
  • Examples of the resin on which the phthalocyanine compound of the present invention is applied or mixed include a transparent resin.
  • a transparent resin include transparent resins such as polyacrylonitrile resin, methacrylonitrile resin, polymethyl methacrylate resin, ABS resin, polystyrene resin, and polyethylene terephthalate resin.
  • Examples of the monomer mixed with the phthalocyanine compound of the present invention include, for example, hexamethylene diisocyanate, isophorone diisocyanate, tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, mesitylene triisocyanate, 1,4-bis ( ⁇ , ⁇ ′- Examples thereof include dimethyl isocyanate methyl) benzene, 1,3,5-tris (3-thiopropyl) isocyanurate, 2,2′-dimethylpropanediol bis (2-thioacetate) and the like.
  • a molded article can be obtained by polymerizing the phthalocyanine compound of the present invention after mixing with these monomers.
  • the phthalocyanine compound of the present invention Since the phthalocyanine compound of the present invention has an absorption ability in the near infrared wavelength region of 750 to 1200 nm, it is a photothermal conversion material that absorbs laser light in this region and converts it into heat, more specifically, laser direct. It can be used for an original plate for plate making (CTP), a recording material (laser thermosensitive recording material, laser thermal transfer recording material, etc.) and the like. That is, the photothermal conversion material of the present invention contains the phthalocyanine compound of the present invention.
  • the photothermal conversion material may contain a binder resin or the like in addition to the phthalocyanine compound of the present invention as a photothermal conversion agent, and examples of the binder resin include the same materials as the near infrared absorbing material.
  • the photothermal conversion material When the photothermal conversion material is used as a recording material such as a laser thermal recording material or a laser thermal transfer recording material, the material may be used with a coloring component or coloring component used, or the coloring component or coloring component may be used. You may provide the layer containing this separately.
  • the coloring component or coloring component is not particularly limited, and known components can be used. Examples thereof include a combination of a sublimable dye / pigment, an electron-donating dye precursor and an electron-accepting compound, and a substance (polymerizable polymer or the like) that forms an image by a physical or chemical change by heat.
  • the electron donating dye precursor used in the laser thermosensitive recording material include triphenylmethane compounds, fluoran compounds, phenothiazine compounds, indolylphthalide compounds, leucooramine compounds, rhodamine lactams. Compounds, triphenylmethanephthalide compounds, triazene compounds, spiropyran compounds, fluorene compounds, and the like.
  • the electron-accepting compound include a phenolic compound, an organic acid or a metal salt thereof, and an oxybenzoic acid ester.
  • coloring components used in laser thermal transfer recording materials include titanium dioxide, carbon black, zinc oxide, Prussian blue, cadmium sulfide, iron oxide, lead, zinc, barium and calcium chromates.
  • examples include inorganic pigments, azo-based, thioindigo-based, anthraquinone-based, anthanthrone-based, triphendioxazine-based, phthalocyanine-based, and quinacridone-based organic pigments.
  • the dye include acid dyes, direct dyes, disperse dyes, oil-soluble dyes, metal-containing oil-soluble dyes, and the like.
  • a photothermal conversion layer is provided on the support.
  • a silicon rubber layer may be laminated on the photothermal conversion layer, or a protective layer or the like may be further laminated.
  • the support examples include paper, paper laminated with plastic (for example, polyethylene, polypropylene, polystyrene, etc.), a metal plate such as aluminum (including aluminum alloy), zinc, copper, etc., cellulose diacetate, triacetic acid
  • plastic films such as cellulose, cellulose butyrate, polyethylene terephthalate, polyethylene, polystyrene, polypropylene, polycarbonate, and polyvinyl acetal.
  • the photothermal conversion layer contains an image forming component, a binder resin, and the like, and examples of the binder resin include the same materials as the near infrared absorbing material.
  • a layer containing an image forming component may be provided by being laminated on the photothermal conversion layer.
  • the image forming component is not particularly limited, and a known component that forms an image by a physical or chemical change by heat can be used.
  • an image part may be formed by laminating a silicon rubber layer on a light-to-heat conversion layer (photosensitive layer or heat-sensitive recording layer), and after exposure, the silicon rubber layer is adhered or peeled off.
  • a lithographic printing plate precursor for printing is prepared by dispersing or dissolving a photothermal conversion material, an image forming component, a binder resin or the like in an organic solvent or the like and applying it to a support.
  • a primer layer may be provided between the support and the light-to-heat conversion layer to improve adhesion and print characteristics, or the support itself may be surface-treated. It does not specifically limit as a primer layer to be used, A well-known component can be used.
  • a protective film may be formed on the photothermal conversion layer or the silicon rubber layer for surface protection.
  • polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polyethylene terephthalate, cellophane, or the like can be laminated, or these films can be stretched to form a protective film.
  • Heat-shielding material The phthalocyanine compound of the present invention has an absorptivity in the near-infrared wavelength region of 750 to 1200 nm and can be used as a heat-shielding material. That is, the heat shielding material of the present invention contains the phthalocyanine compound of the present invention.
  • the heat shielding material of the present invention include, for example, a heat ray absorbing material (of the present invention).
  • the heat ray absorbing material means a material having an absorptivity in a wavelength region of 800 to 2500 nm. Since the heat ray absorbing material of the present invention contains the phthalocyanine compound of the present invention, it is particularly excellent in absorption ability in the near infrared wavelength region of 800 to 1200 nm.
  • the heat ray absorbing material include a heat ray blocking filter (heat shielding film); an interlayer film for laminated glass (particularly window glass), and the like.
  • the laminated glass using the said intermediate film for laminated glasses is also contained in the heat ray absorbing material of this invention.
  • the use of the said heat shield film and laminated glass is not specifically limited, respectively.
  • Specific applications of laminated glass include, for example, for vehicles (trains, automobiles, etc.), buildings (buildings, houses, etc.) and the like.
  • the heat ray absorbing material uses a heat ray absorbent other than the phthalocyanine compound of the present invention.
  • the heat ray absorbent include inorganic fine particles such as tin-doped indium oxide (ITO), antimony-doped tin oxide (ATO), and tungsten oxide.
  • ITO tin-doped indium oxide
  • ATO antimony-doped tin oxide
  • tungsten oxide tungsten oxide.
  • the said heat ray absorber can be used 1 type or in combination of 2 or more types.
  • the heat ray absorbing material may contain a binder resin in addition to the phthalocyanine compound of the present invention.
  • the binder resin include those similar to the binder resin in the near-infrared absorbing material.
  • the method for producing the heat ray absorbing material of the present invention is not particularly limited.
  • the laminated film (the heat ray absorbing material of the present invention) can be obtained by sandwiching the interlayer film for glass between two or more glasses and press-bonding them under predetermined conditions (temperature, pressure, etc.). it can.
  • the first layer containing the phthalocyanine compound of the present invention and the second layer containing the heat ray absorbent may be laminated to form a multilayered intermediate film.
  • each value was measured as follows.
  • a 8.0 ⁇ 10 ⁇ 6 to 11 ⁇ 10 ⁇ 6 mol / L chloroform solution was prepared, and a quartz cell having an optical path length of 1 cm was used.
  • Test Example 1 (Light resistance evaluation) ⁇ Thin film production> 10 mg of the phthalocyanine compounds obtained in Examples 1, 2, 4, 6 to 8, and 10 to 15 were dissolved in 5 ml of a polymethacrylate 18 wt% toluene solution, applied onto a glass substrate by a spin coat method, and dried. A thin film having a thickness of 1.4 ⁇ m was prepared.
  • Dye residual ratio (%) 100 ⁇ (1 ⁇ transmittance after irradiation) / (1 ⁇ transmittance before irradiation) ⁇ : Dye remaining ratio of 65% or more ⁇ : Dye remaining ratio of 50% or more and less than 65% ⁇ : Dye remaining ratio of less than 50%
  • Test Example 2 Solubility Evaluation The compound phthalocyanine compounds obtained in Examples 1, 4, 6, 11 and 12 were weighed into a glass sample bottle, mixed with acetone, stirred and dissolved at room temperature, and the state of the solution was visually observed. Dissolvable weight concentration was evaluated according to the following criteria.
  • the phthalocyanine compound of the present invention has an absorption ability in the near infrared absorption region of 750 to 1200 nm, and is excellent in light resistance and solubility. In particular, it can be suitably used in various applications such as a heat ray absorbing material.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

L'invention porte sur un composé phtalocyanine ayant une excellente résistance à la lumière et une excellente solubilité, et qui est utile en tant qu'absorbant les rayons infrarouges proches. On a constaté qu'un composé phtalocyanine ayant une structure spécifique présente une excellente résistance à la lumière et une excellente solubilité. (Dans la formule, R1 et R2 sont identiques l'un à l'autre ou différents l'un de l'autre, et représentent chacun d'une manière indépendante un groupe alcoxy qui peut avoir un substituant, ou analogues ; X1 et X2 sont identiques l'un à l'autre ou différents l'un de l'autre et représentent chacun d'une manière indépendante un atome d'oxygène ou un atome de soufre ; A1 et A2 sont identiques l'un à l'autre ou différents l'un de l'autre et représentent chacun d'une manière indépendante un noyau aromatique qui peut avoir un substituant ; et M représente deux atomes d'hydrogène, un métal divalent, ou un composé d'un métal trivalent ou tétravalent).
PCT/JP2014/066604 2013-06-28 2014-06-24 Composé phtalocyanine, colorant absorbant les rayons infrarouges proches, et matériau absorbant les rayons infrarouges proches WO2014208514A1 (fr)

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WO2021070693A1 (fr) 2019-10-07 2021-04-15 住友化学株式会社 Composition de résine durcissable colorée
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TWI681907B (zh) * 2015-04-08 2020-01-11 日商出光統一科技股份有限公司 夾鏈帶、附夾鏈帶之袋體、及附夾鏈帶之袋體之製造方法、以及可良好接合長形構件之長形構件之接合方法、其裝置及夾鏈帶之接合裝置
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CN114402017A (zh) * 2019-10-07 2022-04-26 住友化学株式会社 着色树脂组合物
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JP7572827B2 (ja) 2019-10-07 2024-10-24 住友化学株式会社 着色硬化性樹脂組成物
WO2022013112A1 (fr) * 2020-07-16 2022-01-20 Commissariat à l'Energie Atomique et aux Energies Alternatives Composes organiques a emission de fluorescence retardee et de lumiere circulairement polarisee et leur utilisation
FR3112550A1 (fr) * 2020-07-16 2022-01-21 Commissariat A L'energie Atomique Et Aux Energies Alternatives Composes organiques a emission de fluorescence retardee et de lumiere circulairement polarisee et leur utilisation

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