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WO2008029594A1 - Matière pouvant absorber des rayons du proche infrarouge, composition pouvant absorber des rayons du proche infrarouge comprenant la matière et utilisation de celles-ci - Google Patents

Matière pouvant absorber des rayons du proche infrarouge, composition pouvant absorber des rayons du proche infrarouge comprenant la matière et utilisation de celles-ci Download PDF

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Publication number
WO2008029594A1
WO2008029594A1 PCT/JP2007/065767 JP2007065767W WO2008029594A1 WO 2008029594 A1 WO2008029594 A1 WO 2008029594A1 JP 2007065767 W JP2007065767 W JP 2007065767W WO 2008029594 A1 WO2008029594 A1 WO 2008029594A1
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Prior art keywords
infrared absorbing
group
absorbing material
infrared
general formula
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Ceased
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PCT/JP2007/065767
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English (en)
Japanese (ja)
Inventor
Harunori Narihiro
Marie Miyagi
Tetsuya Takagi
Toshiyuki Uemura
Masashi Koide
Hiroyuki Kobayashi
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Artience Co Ltd
Original Assignee
Toyo Ink Mfg Co Ltd
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Publication of WO2008029594A1 publication Critical patent/WO2008029594A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/24—Ablative recording, e.g. by burning marks; Spark recording
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used

Definitions

  • Near-infrared absorbing material near-infrared absorbing composition containing the same, and use thereof
  • the present invention relates to a near-infrared absorbing material comprising a novel dithiol-based polymer, a near-infrared absorbing composition containing the near-infrared absorbing material, a laminate having a layer containing the near-infrared absorbing material, and the near-infrared material.
  • the present invention relates to a near-infrared absorbing film including an infrared absorbing material and a near-infrared absorbing filter including the near-infrared absorbing material. More specifically, there are optical filters for semiconductor light receiving elements, plasma displays, liquid crystal displays, and various other near infrared absorption!
  • Near infrared cut filters near infrared absorption or near infrared cut films
  • Is an optical recording dye a near-infrared absorbing material for laser marking, a near-infrared absorbing material in laser welding, and the near-infrared absorbing material useful in various applications, a laminate having a layer containing these near-infrared absorbing materials
  • the present invention relates to a near-infrared absorbing film containing the near-infrared absorbing material and a near-infrared absorbing filter containing the near-infrared absorbing material.
  • the organic nickel complex generally has an absorption property in the near-infrared part of 950 nm to 1200 ⁇ m, and has excellent properties as a near-infrared absorbing material.
  • the main applications include optical filters for semiconductor light-receiving elements that have the function of absorbing and cutting near infrared rays, near-infrared absorbing films and near-infrared ray absorbing plates that block heat rays for energy conservation, and selective use of sunlight.
  • Near-infrared absorbing film for agricultural purposes, recording medium using near-infrared absorption heat, near-infrared cut filter for electronic equipment, near-infrared filter for photography, protective glasses, sunglasses, heat ray-blocking film, optical recording It is used for applications such as dyes, optical character reading and recording, copy protection of confidential documents, electrophotographic photoreceptors, and laser welding. It is also used for noise cut filters for CCD cameras and filters for CMOS image sensors.
  • PDP plasma display
  • a neon gas having a light emitting element of 800 to 1050 nm is used.
  • This filter requires excellent visible transmission.
  • the dyes used in this filter are required to have high thermal stability and high light resistance.
  • changes in filter chromaticity and deterioration of near infrared absorption ability due to material deterioration are problems.
  • optical elements in an optical device such as a camera or a video camera, a silicon diode element, a complementary metal oxide semiconductor (CMOS), a charge coupled device (CCD), or the like is used to convert an optical signal into an electric signal.
  • CMOS complementary metal oxide semiconductor
  • CCD charge coupled device
  • optical elements have a wide light-sensitive region of 300-00; UOOnm, so in the near-infrared region compared to the human eye's visual sensitivity of 400-700 nm. It will be very sensitive.
  • optical devices such as cameras and video cameras need to be sensitive to wavelength light in the human visibility range, and wavelength light outside this range will interfere with unfavorable photometry and color reproducibility. It will be. Therefore, in this case, an optical filter that transmits visible light and efficiently absorbs and cuts near-infrared light is required.
  • a filter for the above-mentioned CCD and CMOS As a filter for the above-mentioned CCD and CMOS, a phosphoric acid ester copper compound dispersed in a resin (for example, see Patent Documents !! to 5), a composite optical filter having a low-pass function and a visibility correction function (for example, a patent)
  • a filter made of a resin obtained by polymerizing phosphine oxide as a component of the monomer see, for example, Patent Document 7
  • it is not always satisfactory in terms of durability and transparency. Nare Nare ,.
  • Dithiol-based complexes are also known as near-infrared absorbing materials.
  • Known dithiol-based complex near-infrared absorbing materials include bis (dithiobenzyl) nickel complex compounds (see, for example, Patent Documents 8 and 9), bis (1,2 acenaphthylene dithiolato) nickel complex compounds (for example, Patent Document 10), 4 tertbutyl-1,2 benzenedithiol nickel complex (for example, see Patent Document 11), and bis (dithiobenzil) nickel complex compound having an alkoxy group (for example, see Patent Document 12).
  • a dithiolate nickel polymer complex for example, see Patent Document 13
  • a bisdithiolene complex polymer for example, see Patent Document 14
  • Bisdithiolene complex polymers have an absorption wavelength region at a relatively short wavelength of ⁇ 800 nm, It is unsuitable for use as a near-infrared absorbing material.
  • V does not have a substituent at the complex skeleton, it has poor solubility! /, And! /.
  • polynuclear thiol complexes for example, see Patent Document 15
  • quaternary phosphonium bis (cis 1,2-ethylenedithiolato) nickelate derivatives for example, see Patent Document 16
  • dithiolate metal complexes having secondary alkyl groups See, for example, Patent Document 17
  • Patent Document 17 is also known as a long-wavelength absorption material, but it has low solubility in solvents, poor compatibility with resins, is low! It was not practical, such as lack of heat.
  • phthalocyanine-based materials are known as near-infrared absorbing compounds.
  • examples of such phthalocyanine-based materials include phthalocyanine compounds or naphthalocyanine compounds having a substituent (see, for example, Patent Document 18), phthalocyanine compounds having an amino group (see, for example, Patent Documents 19 to 23), fluorine-containing phthalocyanine compounds ( For example, Patent Documents 24 and 25) are known.
  • dimonium dyes are materials that absorb a wide range of long wavelengths (950 nm to UOOnm) and have very good transparency to visible light, and various types are known (for example, , See patent documents 26-29). And this pigment
  • a dithiol nickel complex having an olefin copolymer as a substituent for example, Patent Document 30
  • Patent Document 30 a dithiol nickel complex having an olefin copolymer as a substituent
  • the near-infrared absorbing dye used for the near-infrared absorbing material is generally dissolved in a solvent, then mixed with a resin and coated on a substrate such as plastic, or heated and kneaded with a resin. It is used after being formed into a film, sheet, plate or other shape. For this reason, the near-infrared absorbing dye is required to have excellent solubility in a solvent and compatibility with a resin. Furthermore, since the near-infrared absorbing material may be used outdoors, the near-infrared absorbing dye itself is required to have high durability, thermal stability, and the like.
  • Patent Document 1 W099 / 26951
  • Patent Document 2 W099 / 26952
  • Patent Document 3 Japanese Patent Laid-Open No. 2000-7871
  • Patent Document 4 W098 / 55885
  • Patent Document 5 Japanese Patent Laid-Open No. 2000-38396
  • Patent Document 6 Japanese Patent Laid-Open No. 8-146216
  • Patent Document 7 Japanese Patent Laid-Open No. 2000-98130
  • Patent Document 8 Japanese Patent Laid-Open No. 63-227597
  • Patent Document 9 Japanese Patent Laid-Open No. 64-61492
  • Patent Document 10 Japanese Patent No. 2923084
  • Patent Document 11 Special Japanese Patent Laid-Open No. 63-307853
  • Patent Document 12 Japanese Patent Laid-Open No.
  • Patent Document 13 Japanese Patent Laid-Open No. 4 198304 Patent Document 14: US Patent No. 5089585 Patent Document 15: Japanese Patent Laid-Open No. 2005-181966 Patent Document 16: Japanese Patent Publication No. 6-72147 Patent Document 17: Japanese Patent Application Laid-Open No. 2005-232185 Patent Document 18: Japanese Patent Application Laid-Open No. 10-78509 Patent Document 19: Japanese Patent Application Laid-Open No. 2004-18561 Patent Document 20: Japanese Patent Application Laid-Open No. 2004-18561 Japanese Patent No. 2001-106689 Patent Document 21: Japanese Patent Laid-Open No. 2000-63691 Patent Document 22: Japanese Patent No. 2746293, Patent Document 23: Japan Special Patent No.
  • Patent Literature 24 Japanese Patent No. 2907624
  • Patent Literature 25 Japanese Patent No. 3014221
  • Patent Literature 26 Japanese Patent Laid-Open No. 05-247437
  • Patent Literature 27 Japanese Patent Laid-Open No. 2005-325292
  • Patent Literature 28 Japanese Patent No. 3699464
  • Patent Document 29 Japanese Patent Laid-Open No. 2003-096040
  • Patent Document 30 US Patent No. 6489399
  • phthalocyanines are substituted with various substituents to improve solubility in solvents, but as a result, light resistance, thermal stability, etc. are inferior.
  • the absorption spectrum is sharp, the wavelength range that can absorb near infrared rays is small.
  • substituted benzenedithiol-nickel complexes are superior in that they are relatively easy to manufacture and have good durability. Solubility in solvents Force S is small and compatibility with resins There is a problem of being inferior.
  • the near-infrared absorbing material when the near-infrared absorbing material is dissolved in a solvent and has a low solubility in a solvent! /, It is used to block near-infrared rays on the surface of glass, paper or resin used as a substrate. It becomes difficult to contain a sufficient amount of the dye.
  • the film thickness is increased to include a sufficient amount of dye, a new absorption band appears in the visible light region due to the stacking of the dye molecules, causing a reduction in visible light transmittance.
  • the intermolecular interaction is increased, resulting in a decrease in near-infrared absorption characteristics.
  • the solubility of the dye in the solvent and the compatibility with the resin are low! / And it becomes difficult to contain a sufficient amount of the dye to block near infrared rays, and the transparency of visible light , Long wavelength (800 ⁇ ; UOOnm) absorption is also low and resistance is low.
  • the Hansen solubility parameter is used as a standard for evaluating the solubility between substances, that is, the compatibility.
  • a parameter (SP value) is used, and the unit is represented by (cal / cm 3 ) 172 .
  • SP value is simply abbreviated as “solubility parameter” or “SP value”.
  • SP value is simply abbreviated as “solubility parameter” or “SP value”.
  • the first solubility parameter is the dispersion force ( ⁇ ), which occurs between the permanent dipoles of the molecule d
  • the object of the present invention is easy to manufacture, good solubility in a solvent and good compatibility with a resin, and has a wide near-infrared absorption region and excellent heat resistance and durability. It is to provide an infrared absorbing material.
  • Another object of the present invention is to provide a near-infrared absorbing composition containing a near-infrared absorbing material having the above excellent characteristics.
  • Another object of the present invention is to provide a near-infrared-absorbing laminate containing at least one near-infrared absorbing material having the above-mentioned excellent characteristics, and to provide near-infrared absorption having the above-mentioned excellent characteristics. It is providing the resin film containing material.
  • Another object of the present invention is to provide an optical filter containing a near-infrared absorbing material having the above excellent characteristics.
  • the present invention relates to the following near-infrared absorbing material, near-infrared absorbing composition, laminate, resin film, and optical filter.
  • M represents a metal atom, one of 1 ⁇ to 1 ⁇ ° represents a direct bond, and the other represents a divalent group represented by the following general formula (2). And the rest each independently represents a hydrogen atom or a substituent.
  • Ar 1 and Ar 2 represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group
  • n a natural number
  • [3] in the near infrared absorbing material according to [1] is any one of the direct binding of I ⁇ to R 5, any one of R 6 to R 1Q general formula (2)
  • [4] in the near infrared absorbing material according to [1] is any one of the direct binding of I ⁇ to R 5, another of I ⁇ to R 5 have the general formula (2)
  • the near-infrared absorbing material has the general formula (
  • a near-infrared absorbing material which is a homopolymer having a repeating unit represented by 1).
  • the near-infrared absorbing material contains at least two types of repeating units represented by the general formula (1) as repeating units.
  • a near-infrared absorbing material characterized by being a copolymer.
  • the divalent group represented by the general formula (2) is bonded to! /, NA! /, And the benzene ring is substituted at the ortho position.
  • a near infrared ray absorbing material characterized by comprising:
  • a near-infrared absorbing composition comprising a non-resin resin and the near-infrared absorbing material according to any one of [1] to [9] above.
  • the dispersive force ( ⁇ ) which is a Hansen solubility parameter of each of the binder resin and the near-infrared absorbing material, between the permanent dipoles of the molecule
  • the force ( ⁇ ) generated in the molecule and the hydrogen bonding force ( ⁇ ) of the molecule are 7 ⁇ 0 ⁇ ⁇ dphd
  • a near infrared ray absorbing composition characterized by comprising:
  • the near-infrared absorbing material has a near-infrared absorption wavelength represented by the general formula (1).
  • a near-infrared absorbing composition comprising two or more different near-infrared absorbing materials.
  • the near-infrared absorbing composition according to any one of [10] to [; 16] above, wherein the near-infrared absorbing composition is further represented by the following general formula (11): A near infrared ray absorbing composition comprising a material.
  • R 5 ° to R 53 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Or a substituted or unsubstituted silyl group or a substituted or unsubstituted acyl group, and two Rs in the same ligand may be bonded to each other to form a ring, which is also a monovalent salt. Also good.
  • R 5 ° to R 53 in the general formula (11) are monovalent organic residues represented by the following general formula (12).
  • X 5 represents a direct bond or 0- ⁇ S ⁇ —CO—, a substituted or unsubstituted imino group
  • n 1 represents a natural number
  • n 2 represents 0 or a natural number
  • R 54 ⁇ R 58 represents a hydrogen atom or a substituent.
  • a resin film comprising the near-infrared absorbing material according to any one of [1] to [9] or the near-infrared absorbing composition according to any one of [10] to [20].
  • the near-infrared absorbing material having a repeating unit represented by the general formula (1) of the present invention is easy to manufacture, has excellent light resistance and heat resistance, and has a wide absorption in the near-infrared region of 800 nm to 1100 nm. It is a polymer useful as a near-infrared absorbing material.
  • the SP value of the near-infrared absorbing material of the present invention is close to the SP value of the binder resin and solvent used in the near-infrared absorbing composition! Compared with the resin and solvent, the content of the near-infrared absorbing material in the near-infrared absorbing composition can be increased as compared with the conventional one.
  • the near-infrared absorbing composition containing the near-infrared absorbing material of the present invention is thin! /, Forming a highly durable film with good near-infrared absorption even in a film and high light transmittance in the visible light region. can do.
  • the near-infrared absorbing composition of the present invention can form a resin film with a force S that can form a film by applying the composition to a substrate, itself.
  • the obtained near-infrared absorbing film, the laminate having this film, and the near-infrared absorbing resin film are used as an optical filter for plasma displays, liquid crystal displays, CCD cameras, CMOS image sensors, etc., and energy saving.
  • Near-infrared absorbing films and near-infrared absorbing plates that block heat rays used for applications, agricultural near-infrared absorbing films for selective use of sunlight, recording media and laser welding that use near-infrared absorbing heat Near-infrared cut filter for electronic equipment, near-infrared filter for photography, protective glasses, sunglass, heat ray blocking film, dye for optical recording, optical character reading recording, confidential document copy prevention, electrophotographic photoreceptor, etc. It can be preferably used.
  • the present invention provides a novel near-infrared absorption having a repeating unit represented by the general formula (1).
  • Material a near-infrared absorbing composition containing the novel near-infrared absorbing material, a laminate having the near-infrared absorbing material or a layer containing the near-infrared absorbing composition, and a near-infrared absorbing resin containing the near-infrared absorbing material
  • the present invention relates to a near-infrared absorbing filter including a film, a near-infrared absorbing laminate, and a near-infrared absorbing resin film.
  • M represents a metal atom
  • one of 1 ⁇ to 1 ⁇ ° represents a direct bond
  • the other represents a general formula (2):
  • the metal atom of ⁇ ⁇ ⁇ ⁇ in the general formula (1) is not particularly limited as long as it is a metal atom, but nickel, cobalt, platinum, palladium or copper is more preferable.
  • the "substituent" of 1 ⁇ to ° is a halogen atom such as a fluorine atom, chlorine atom, bromine atom or iodine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, Substituted or unsubstituted thioalkoxy group, cyano group, amino group, mono or disubstituted amino group, hydroxyl group, mercapto group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylothio group, substituted or unsubstituted aryl group , Replaced or not It represents a substituted heteroaryl group, and the “substituent” may form a conjugated or non-conjugated ring with or without substitution between adjacent substituents.
  • a halogen atom such as a fluorine atom, chlorine atom, bromine
  • substituted or non-conjugated ring that is substituted or unsubstituted between adjacent substituents include 5- or 7-membered oxygen, nitrogen, and sulfur atoms between adjacent substituents.
  • Aliphatic, carbocyclic aromatic, heterocyclic aromatic, and heterocyclic ring may be mentioned, and these rings may further have a substituent at any position.
  • these groups will be described in more detail.
  • the substituted or unsubstituted alkyl group constituting the "substituent" of 1 ⁇ to 1 ⁇ ° is not particularly limited as long as it is a substituted or unsubstituted alkyl group.
  • the alkynole group may be linear, branched, or cyclized cycloalkyl group.
  • Specific examples of substituted or unsubstituted alkyl groups include, for example, methyl, ethyl, propyl, butyl, sec butyl, tert butyl, pentyl, hexyl, 2-ethylhexyl.
  • the substituted or unsubstituted alkoxy group constituting the "substituent" of 1 ⁇ to ° is not particularly limited as long as it is a substituted or unsubstituted alkoxy group.
  • the substituted or unsubstituted thioalkoxy group constituting the "substituent" of 1 ⁇ to ° is not particularly limited as long as it is a substituted or unsubstituted thioalkoxy group.
  • examples thereof include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a sec-butylthio group, a tert butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, and an octylthio group.
  • the mono- or di-substituted amino group constituting the "substituent" of 1 ⁇ to ° is mono- or di- It is not particularly limited as long as it is a di-substituted amino group.
  • examples of the substituted or unsubstituted aryloxy group constituting the "substituent" of 1 ⁇ to ° include a phenoxy group, p-tert-butylphenoxy group, 3-fluorophenoxy group and the like. .
  • examples of the substituted or unsubstituted arylothio group constituting the "substituent" of 1 ⁇ to o include a phenylthio group and a 3-fluorophenylthio group.
  • the substituted or unsubstituted aryl group constituting the "substituent" of 1 ⁇ to ° is, for example, a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, 3-nitrophenyl.
  • substituted or unsubstituted heteroaryl group constituting the "substituent" of 1 ⁇ to ° are, for example, thionyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyradyl group.
  • pyrimidinyl group pyridazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalajuryl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acrylidinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, flazanyl group Phenoxazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2-methylpyridyl group, 3-cyanopyridyl group and the like.
  • conjugated or non-conjugated ring having a substituted or unsubstituted group formed by the bonding of adjacent substituents constituting the "substituent" of 1 ⁇ to ° for example, substituted cyclohexyl Group, naphthyl group and the like.
  • Examples of the substituted imino group include the following.
  • Ar 1 and A in the general formula (2) represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, preferably a substituted or unsubstituted phenylylene group. is there.
  • the substituted or unsubstituted arylene group is preferably a monocyclic or condensed ring arylene group having 6 to 60 carbon atoms, more preferably 6 to 40 carbon atoms, still more preferably 6 to 30 carbon atoms.
  • Specific examples include phenylene, biphenylene, naphthalenezyl, anthracenezyl, phenanthrene lindyl, pyrenezyl, triphenylinole, benzophenanthin lindinore, perylene diole, pentaphenylene ginole, pentasensyl, etc.
  • These groups may have a substituent. Examples of these substituents include those similar to the above-described 1 ⁇ -° C substituents.
  • the substituted or unsubstituted heteroarylene group is preferably a monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms, more preferably a nitrogen atom, A monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms containing at least one of an oxygen atom or a sulfur atom, more preferably a 5 or 6 membered carbon group having 4 to 30 carbon atoms.
  • An aromatic heterocyclic group is preferably a monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms, more preferably a nitrogen atom, A monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms containing at least one of an oxygen atom or a sulfur atom, more preferably a 5 or 6 membered carbon group having 4 to 30 carbon atoms.
  • An aromatic heterocyclic group include pyrrole ', Huena
  • these groups may have a substituent.
  • substituents include the same ones as the above-mentioned 1 ⁇ -° C substituents.
  • n a natural number
  • Y a direct bond or an unsubstituted alkylene group
  • substituent of the substituted imino group a linear, branched or cyclic alkyl group is preferable.
  • the repeating unit represented by the general formula (1) is preferably (i) I ⁇ R
  • the repeating unit of the general formula (1) has a substituted or unsubstituted aryl including the substituent constituting the divalent group of the general formula (2), so that the dispersion force ( ⁇ ) is increased. Is done. Medium d
  • the force ( ⁇ ) generated between the permanent dipoles of the molecule is increased by using a group having a halogen atom or a carbonyl group as 1 ⁇ to 1 ⁇ ° of the phenyl group.
  • ⁇ ⁇ 4 of general formula (2) sulfides bond group, ether bond, urethane bond group, an amino-de-binding group, a carbonyl group, an ester group, an amino group, a substituted or unsubstituted alkylene group It is possible to increase ⁇ and ⁇ ⁇ of near-infrared absorbing materials by using
  • the near-infrared absorbing material of the present invention has the basic skeleton of the general formula (1), SP straight is 7.0 ⁇ ⁇ 9.0, 0.1 ⁇ ⁇ 5.5, 0.1 ⁇ ⁇ ⁇ 5.0. Also, the above one d p h
  • the repeating unit represented by the general formula (1) has a divalent group represented by the general formula (2).
  • the solubility in a solvent is improved.
  • Preferred examples of the substituent at the ortho position of the benzene ring include a halogen atom and an alkyl group having 1 to 20 carbon atoms such as a chlorine atom and a methyl group.
  • the divalent group represented by the general formula (2) is bonded to! / It is preferable to replace it with the place.
  • the SP of the near-infrared spring absorbing material is 7 ⁇ 0 ⁇ ⁇ 9.00, 0.1 ⁇ ⁇ 5.5, 0.1 ⁇ ⁇ 5.
  • the solubility index in the solvent is 1. Owt% or more with respect to toluene, 0.2 wt% or more with respect to ethyl acetate, and 1.
  • the polymer having the repeating unit represented by the general formula (1) may be a homopolymer or a copolymer.
  • the copolymer may be a copolymer composed of two or more kinds of repeating units represented by the general formula (1), or the repeating unit represented by the general formula (1) and the general formula (1).
  • a copolymer containing a repeating unit not corresponding to the repeating unit represented by The copolymer may be a random, block, or graph copolymer.
  • the copolysynthetic component other than the repeating unit represented by the general formula (1) is a compound having a polymerizable reaction end, for example, a small number of OH groups in the same molecule.
  • the weight-average molecular weight of the near-infrared absorbing material of the present invention is not particularly limited from the viewpoint of heat resistance and light resistance.
  • it is 1,000 to 10 in terms of polystyrene by gel permeation chromatography measurement.
  • the power is preferably about 000.
  • the near-infrared absorbing material represented by the general formula (1) of the present invention has an absorption region at 800 nm to 1, lOOnm, and therefore can be preferably used as a near-infrared absorbing material.
  • the general formula (4) and the general formula (5) are structural isomers and can be used without distinction, either one of them may be used as a near-infrared absorbing material, or the structure without separation. It may be used as a mixture of isomers. Further, units having different near infrared absorption regions may be copolymerized as necessary, or polymers having different near infrared absorption regions may be mixed.
  • the near-infrared absorbing material represented by the general formula (1) may be used in any combination of homopolymers. Further, the near-infrared absorbing material having the structure represented by the general formula (11) is used at the same time. It's okay. When using a near-infrared absorbing material having the structure represented by the general formula (11), a single structure may be used! /, Or a combination of different structures may be used.
  • Table 1 specifically shows typical structural examples of the repeating unit represented by the general formula (1) used in the polymer which is the near-infrared absorbing material of the present invention.
  • the repeating unit constituting the polymer of the material is not limited to the repeating unit shown in the following specific examples.
  • Table 1 shows only the structure of each unit monomer, and does not show its polymerization form. Further, the structural isomers of the general formula (4) and the general formula (5) are representatively described by the repeating unit of the general formula (5).
  • the near-infrared absorbing material having a repeating unit represented by the general formula (1) of the present invention can be produced, for example, according to the following synthesis scheme.
  • R 21 to R 24 are a phenyl group or a phenylene group which may be substituted with a substituent
  • Q is a part of the general formula (2),-[CH 2] -X ′ -Ar'-Y-Ar'-X 3- [CH] Equivalent to one.
  • the polymer represented by the general formula (6) or the general formula (7) is also exemplified by, for example, a compound It can be produced in the same manner by using a compound in which one Br or one OH group of A or B is substituted with R 21 and R 22 or R 21 which is the same group.
  • These synthesis schemes show only a part of the scheme for synthesizing the near-infrared absorbing material of the present invention, and the synthesis scheme of the near-infrared absorbing material of the present invention is limited to the following! Of course.
  • a base such as NaOH, KOH, KCO, NaCO, or triethylamine in a polar solvent such as dimethylformamide, dimethylsulfoxide, or methylethylketone
  • a polar solvent such as dimethylformamide, dimethylsulfoxide, or methylethylketone
  • near-infrared absorbing materials can be used as necessary together with the near-infrared absorbing material having the repeating unit represented by the general formula (1).
  • a near infrared ray absorbing material that can be particularly preferably used in the present invention there is a near infrared ray absorbing material represented by the following general formula (11).
  • M 2 represents a metal atom, R 5 ° to R 5 substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, Or a substituted or unsubstituted silyl group or a substituted or unsubstituted acyl group;
  • the two Rs in the ligand may be bonded to each other to form a ring or may be a monovalent salt.
  • the metal atom of M 2 is not particularly limited as long as it is a metal atom, but nickel, cobalt, platinum, noradium or copper is preferable. More preferred is nickel.
  • substituted or unsubstituted alkyl group of R 5 ° to R 53 in the general formula (11) substituted or is not intended to be Yogu particularly limited as long as it is an alkyl group unsubstituted.
  • the alkyl group may be linear, branched or cyclized cycloalkyl group.
  • Specific examples of substituted or unsubstituted alkyl groups include methyl, ethyl, propyl, butyl, sec butyl, tert butyl, pentyl, hexyl, and 2-ethynole hexyl groups.
  • the substituted or unsubstituted aryl group of R 5 ° to R 53 in the general formula (11) includes, for example, a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, and 3-nitrophenyl.
  • the substituted or unsubstituted heteroaryl group of R 5 ° to R 53 in the general formula (11) includes, for example, thionyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyradyl group, pyrimidinyl Group, pyridazinyl group, indolyl group, quinolyl group, isoquinolinol group, phthalajur group, quinoxalinyl group, quinazolinyl group, carbazolyl group, attaridinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, furazanyl group, benzothiazyl group, phenothiazyl group Examples include a benzoxazolyl group, a benzimidazolyl group, a 2-methylpyridyl group, and a 3-cyanopyr
  • Examples of the substituted or unsubstituted silyl group of R 5 ° to R 53 in the general formula (11) include triisopropyl silyl group, trimethylsilyl group, dimethylphenylsilyl group, tert-butyldimethylsilyl group dodecyldimethylsilyl group, etc. Is mentioned.
  • the monovalent salt in the general formula (11) has a structure represented by the following general formula (13).
  • X + is preferably a quaternary ammonium cation, a pyridinium cation, and a quaternary phosphonium cation.
  • quaternary ammonium cation examples include tetraethyl ammonium ion, tetraptyl ammonium ion, benzyltrimethyl ammonium ion, and pyridinium cation includes hexadecyl pyridinium.
  • Examples include ureum cations and N-butyl-4-methylpyridinium ions, and quaternary phosphonium cations include, but are not limited to, tetrabutinorephosphonium ion, tripheninorepheptinorephosphonium ion, and tetraphenylphosphonium ion.
  • R in the same ligand is preferably a ring structure bonded to each other. Particularly preferred is CH 2 —CH 1.
  • Examples of the near infrared absorbing material represented by the general formula (11) are shown in Table 2, but the near infrared absorbing material represented by the general formula (11) is not limited to the following.
  • Near-infrared absorbing materials represented by general formula (1) and general formula (11) includes a near-infrared absorbing material represented by general formula (13)). When included at the same time, these may be included in any ratio, but a preferred ratio is a near infrared absorbing material represented by the general formula (1): a compound power represented by the general formula (11): 1 by weight ratio : 0.5-1: 5 is preferable. In this case, the near-infrared absorbing material represented by the general formula (1) “one ⁇ — [CH 2 ] -X 2
  • a co-compatibility effect occurs, and the near-infrared absorbing material represented by the general formula (1) is uniformly dispersed or dissolved in the resin. As a result, heat resistance and light resistance are improved.
  • the composition containing the near-infrared absorbing material having the repeating unit of (1) can be used in any application that requires near-infrared absorption, and its usage mode and usage mode.
  • the structure of the near infrared ray absorbing material is not limited. sand That is, the near-infrared absorbing material of the present invention is a near-infrared absorbing material (near-infrared absorbing dye) other than the near-infrared absorbing material containing the repeating unit structure of the above general formula (1), for example, the general formula It can be used together with auxiliary materials such as a near-infrared absorbing material represented by (11), other near-infrared absorbing materials, stabilizers such as ultraviolet absorbers and antioxidants.
  • auxiliary materials such as a near-infrared absorbing material represented by (11), other near-infrared absorbing materials, stabilizers such as ultraviolet absorbers and antioxidants.
  • the near-infrared absorbing material of the present invention is dissolved in a solvent together with these auxiliary components or dispersed in a solvent or water, or if necessary, dissolved in a solvent together with a binder resin or the like, or dispersed in a solvent or water.
  • the near-infrared absorbing layer can be formed by forming an absorbing composition and using it as a coating agent and applying it to a substrate or the like.
  • the binder resin is capable of forming a self-supporting film, for example, the composition is applied onto a peelable substrate to form a film, and then the film is removed from the peelable substrate. It can be peeled off and used as a near-infrared absorbing film.
  • the coating agent referred to in the present invention is a processing material having near infrared absorptivity composed of a liquid composition or a paste-like composition containing a resin and / or an organic solvent or water.
  • the coating agent of the present invention can be prepared by dissolving or dispersing the near-infrared absorbing material of the present invention in an appropriate coating agent.
  • the coating agent of the present invention may be an oily coating agent or an aqueous coating agent.
  • the near-infrared absorbing material of the present invention is applied to other functional layers such as an adhesive or an adhesive layer, an ultraviolet absorbing layer, a hard coat layer, and a substrate. You may make it contain and give a near-infrared absorption characteristic to these layers.
  • a conventional known adhesive is added to the adhesive composition.
  • This near-infrared-absorbing adhesive layer uses an adhesive to form a near-infrared-absorbing adhesive layer or adhesive layer.
  • This layer may be used as a near infrared absorption filter layer.
  • the other components may be included. Further, if necessary, it can be contained in a molding resin to form a molded product having a near-infrared absorbing film! /.
  • a laminate or a single film having a near-infrared absorbing layer containing the near-infrared absorbing material of the present invention is preferably used as an optical filter.
  • the near-infrared absorbing material of the present invention is made into a near-infrared absorbing composition together with a binder resin as necessary, and is applied onto a substrate.
  • a layer containing a near-infrared absorbing material can be formed into a laminate.
  • a laminated body can be used for an optical filter, an optical reflecting plate, an optical diffusion plate, etc., for example.
  • other light-absorbing dyes such as other near-infrared absorbing materials represented by the general formula (11), stabilizers, solvents, adhesive resins, other auxiliary components, If necessary, the laminate layer may be formed by using components that form other functional layers.
  • the binder resin when constituting an oil-based coating agent, may be an aliphatic ester resin, an acrylic resin, a melamine resin, a urethane resin, An aromatic ester resin, a polycarbonate resin, an aliphatic polyolefin resin, an aromatic polyolefin resin, a polybule resin, a polybulal alcohol resin, a polybulum modified resin, and a copolymer resin thereof can be exemplified.
  • natural polymer materials such as gelatin, casein, starch, cellulose derivatives, and alginic acid are used.
  • an appropriate resin or copolymer may be selected depending on whether the coating agent is oily or aqueous.
  • the glass transition temperature of these resins is preferably 80 ° C. or higher in view of the durability of the formed coating layer.
  • a glass transition temperature of room temperature or lower for example, 0 ° C. or lower is desirable from the viewpoint of adhesive physical properties.
  • examples of the organic solvent constituting the oil-based coating agent include halogen-based, alcohol-based, keton-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, Eutel-based solvents, and the like. Can be mentioned.
  • the near-infrared absorbing material of the present invention is pulverized to obtain fine particles of several micrometers or less, and the fine particles are placed in an uncolored acrylic polymer emulsion. A method of dispersal.
  • Examples of other light-absorbing dyes other than the near-infrared absorbing material represented by the general formula (11) include cyanine-based, quinoline-based, coumarin-based, thiazole-based, oxonol-based, azulene-based, squarylium. , Azomethine, azo, benzylidene, xanthene, lid opening Examples include cyanine-based, naphthalocyanine-based, naphthoquinone-based, anthroquinone-based, triphenylmethane-based, dimonium-based, and dithiol metal complex-based compounds.
  • the other light-absorbing dyes nickel complex dyes and / or phthalocyanine dyes and / or dimonium dyes, which are near-infrared absorbing materials, are preferable.
  • the addition amount of these other light-absorbing dyes to the near-infrared absorbing material of the present invention is preferably 20 to 500 parts by weight, more preferably 50 to 200 parts by weight with respect to 100 parts by weight of the near-infrared absorbing material of the present invention. It is. In view of the absorption spectrum, it is preferable that the film has a visible light transmittance of 70 to 80% or more and a transmittance in the near infrared region of 10% or less.
  • the nickel complex dye is preferably represented by the following general formula (8). Furthermore, the nickel complex dye may be an ionized compound with a monovalent cation.
  • R represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group
  • R 6 ° to R 63 represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and the substituents in the same ligand are bonded to each other to form a conjugated or non-conjugated ring. It may be formed.
  • the nickel complex dyes having the structure of the general formula (8) are specifically the following: American Dye Source, Ink (Laser Dyes & Near Infrared Dyes) d ADS845MC, ADS870MC, ADS880MC, ADS890MC, Examples include, but are not limited to, ADS920MC and A DS990MC.
  • near infrared absorptivity in which R 29 to R 32 are all S, and R 6 ° to R 63 are substituted phenyl groups An example of a dye Table 3 shows.
  • These near-infrared absorbing dyes in Table 3 are dyes that may be formed as a by-product when synthesizing a near-infrared absorbing material having a repeating unit of the general formula (1) of the present invention.
  • M 1 represents a metal atom
  • R 33 to R 48 each represents a hydrogen atom or a substituent
  • M 1 may further have a substituent.
  • Specific examples include, but are not limited to, IETC Color IR-10, IR-12, IR-14 manufactured by Nippon Shokubai Co., Ltd.
  • the dye having a structure represented by the following general formula (10) is preferable as the dimonium dye.
  • X— represents a halogen ion, an inorganic acid ion or an organic acid ion.
  • examples of the X- halogen ion include iodine ion, chlorine ion, chlorine ion, and fluorine ion.
  • examples of inorganic acid ions include hexafluoroantimonate ion, perchlorate ion, tetrafluoroborate ion, hexafluorophosphate ion, and nitrate ion.
  • organic acid ion examples include acetate ion, trifluoroacetate ion, methanesulfonate ion, trifluoromethanesulfonate ion, benzenesulfonate ion, toluenesulfonate ion and the like.
  • examples of commercially available products include IRG-022, IRG-023, IRG-0 manufactured by Nippon Kayaku Co., Ltd. 40 and the like, but are not limited thereto.
  • Examples of the various stabilizers used for the purpose of stabilizing the near-infrared absorbing material of the present invention and the other light-absorbing dyes with respect to light or heat include, for example, hydride quinone derivatives. (See U.S. Pat. No. 3,935,016 and U.S. Pat. No. 3,982,944), Hydone quinone diether derivative (see U.S. Pat. No. 4,254,216), phenol derivative (see JP-A 54-21004), spiroindane or Derivatives of methylenedioxybenzene (see British Patent Application Publication No. 2077455, British Patent 2062888), Chroman, Spirochroman or Coumaran derivatives (US Pat. No.
  • the optical filter of the present invention may contain an aromatic nitroso compound, an aminium compound, an iminium compound, a bisiminium compound, a transition metal chelate compound, etc. as a quencher such as singlet oxygen.
  • a quencher anion such as a bisthiolate metal complex lanion.
  • the addition amount of other light-absorbing dyes and various stabilizers to the near-infrared absorbing material of the present invention is preferably 20 to 200 parts by weight with respect to 100 parts by weight of the near-infrared absorbing material of the present invention. More preferably 50 to 150 parts by weight.
  • the ratio is preferably such that the visible light transmittance is 70 to 80% or more and the transmittance in the near infrared region is 10% or less when used as a film.
  • the near-infrared absorbing material of the present invention is not only a coating agent but also an adhesive or an adhesive. Can be used as power S.
  • the coating agent of the present invention may contain additives such as ultraviolet absorbers and antioxidants.
  • the use of the coating agent of the present invention is not particularly limited as long as it is intended for surface coating of a substrate. According to the coating agent of the present invention, a coating film having near infrared absorptivity is formed. Can do.
  • an adhesive binder may be used as a solder.
  • the adhesive binder include acrylic, urethane and rubber.
  • monomers that can be used as acrylics acrylic monomers, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, 2- Ethylhexenoyl (meth) acrylate, heptyl (meth) acrylate, hexyl (meth) acrylate, octa nolate (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undecyl ( (Meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, acryl
  • an acrylic monomer having a carbon number of ⁇ 12 for copolymerization and more preferably butyl (meth) acrylate, 2-ethylhexyl ( (Meta) Atallate, which can be used alone or in combination of two or more for the purpose of obtaining desirable physical properties as an adhesive.
  • the weight average molecular weight (Mw) of an acrylic copolymer obtained by copolymerizing an acrylic monomer, an acrylic monomer having an alkylene oxide chain, and other monomers in the above adhesive binder is 50,000 to 100.
  • a low molecular weight acrylic copolymer having a molecular weight of 50,000 to 200,000 is more preferable.
  • the pressure-sensitive adhesive comprising the pressure-sensitive adhesive binder and the near-infrared absorbing material of the present invention is coated on the base material by a known method to form a pressure-sensitive adhesive sheet as a laminate.
  • a known method to form a pressure-sensitive adhesive sheet as a laminate.
  • paper, metal, cloth, etc. are used as the base material used here.
  • Adhesive sheet that does not require a base material if the adhesive binder power can be used alone It becomes.
  • the form by which an adhesive is coated on both surfaces of a base material may be sufficient.
  • the pressure-sensitive adhesive on one side may not include the pressure-sensitive adhesive of the present invention.
  • the pressure-sensitive adhesive comprising the pressure-sensitive adhesive binder and the near-infrared absorbing material of the present invention is coated on a substrate by a known method to form a pressure-sensitive adhesive sheet as a laminate.
  • a substrate In addition to the base material described later, paper, metal, cloth, and the like are used as the base material used here.
  • the adhesive binder can form a sheet alone, it becomes an adhesive sheet that does not require a substrate.
  • the form by which an adhesive is coated on both surfaces of a base material may be sufficient. However, the case where the adhesive of one surface does not contain the adhesive of the present invention may be used.
  • the addition amount of the near-infrared absorbing material of the present invention to the binder resin is preferably 0.0 to 20 parts by weight of the near-infrared absorbing material with respect to 100 parts by weight of the resin. Or 0.;! ⁇ 15 parts by weight. If this proportion is less than 0.01 parts by weight, light in the near-infrared region cannot be efficiently absorbed, whereas if it exceeds 20 parts by weight, the dispersibility of the near-infrared absorbing material can be reduced. Decreases and transparency (visible light transmission) is impaired.
  • the adhesive in the present invention is a processed material having near infrared absorption comprising the near-infrared absorbing material and adhesive of the present invention.
  • the adhesive of the present invention can be prepared by dissolving or dispersing the near-infrared absorbing material of the present invention in an appropriate medium having adhesiveness.
  • each layer such as an undercoat layer, an antireflection layer, a hard coat layer, and a lubricating layer may be provided on the substrate as necessary.
  • the method of incorporating the near-infrared absorbing material of the present invention, the above other light-absorbing dyes and various stabilizers into the optical filter of the present invention include, for example, a method of incorporating a substrate or any arbitrary layer, a substrate Alternatively, a method for coating each arbitrary layer, a method for mixing with a polymer binder or adhesive between each layer, a pressure-sensitive adhesive, a method for providing a near-infrared absorbing layer containing the near-infrared absorbing material of the present invention separately from each of the above layers, etc. Is mentioned.
  • the near-infrared absorbing material of the present invention is suitable for a method of mixing a polymer binder, adhesive, or pressure-sensitive adhesive between layers and a method of providing a near-in
  • the amount of the near-infrared absorbing material of the present invention used per unit area of the optical filter 000 mg / m 2 , preferably 5 to 100 mg / m 2 . If the amount used is less than lmg / m 2 , the near-infrared absorption effect cannot be fully exerted, and if it is used over 1000 mg / m 2 , the color of the filter becomes too strong and the display quality etc. This is not preferable because there is a possibility that the brightness may be lowered and the brightness may be lowered.
  • Examples of the material for the base material include inorganic materials such as glass; or, for example, diacetylenoresolerose, triacetinolecenerose (TAC), propionylcellulose, butyrinoresenorelose, and acetylenopro.
  • Cenorelose ester such as pionorescenolose and nitrosenololose; polyamide; polycarbonate; polyethylene terephthalate, polyethylene naphthalate, polyethylene 1, 2 diphenoxetane 4, 4'-dicanoloxylate, polybutylene terephthalate, etc.
  • the substrate is preferably a transparent support.
  • the transmittance of the transparent support is 80% or more, preferably S, and more preferably 86% or more.
  • the haze is preferably 2% or less, more preferably 1% or less.
  • the refractive index is preferably 1.45-1.70.
  • a light-absorbing dye an antioxidant, a light stabilizer, an ultraviolet absorber, organic fine particles, and the like can be added.
  • the power can be applied.
  • examples of the inorganic fine particles include inorganic fine particles such as silicon dioxide, titanium dioxide, barium sulfate, calcium carbonate, talc, and kaolin.
  • Examples of the various surface treatments include chemical treatment, mechanical treatment, corona discharge treatment, flame treatment, ultraviolet irradiation treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment, mixed acid treatment. And ozone oxidation treatment.
  • the undercoat layer is a layer used between the base material and the near-infrared absorbing layer when the near-infrared absorbing layer containing the near-infrared absorbing material of the present invention is provided.
  • the undercoat layer is made of glass It is formed as a layer containing a polymer having a transition temperature of ⁇ 60 to 60 ° C., a layer having a rough surface on the near infrared absorbing layer side, or a layer containing a polymer having affinity with the polymer of the near infrared absorbing layer.
  • An undercoat layer is provided on the surface of the base material on which the near-infrared absorbing layer is not provided to improve the adhesive force between the base material and the layer provided thereon (for example, an antireflection layer or a hard coat layer).
  • the undercoat layer may be provided to improve the affinity between the optical filter and the adhesive for attaching the optical filter and the image forming apparatus.
  • the thickness of the undercoat layer is preferably 2 ⁇ to 20 ⁇ force S, more preferably 5nm to 5 ⁇ m force S, more preferably 20nm to 2 ⁇ m force, more preferably 501 111 to 1 ⁇ 111, more preferably 80nm to 300nm. Most preferred.
  • the undercoat layer containing a polymer having a glass transition temperature of ⁇ 60 to 60 ° C.
  • Polymers having a glass transition temperature of 60 to 60 ° C include, for example, butyl chloride, vinylidene chloride, butyl acetate, butadiene, neoprene, styrene, black-prene, acrylic ester, methacrylic ester, acrylonitrile or methyl butyl ether. It can be obtained by polymerization or copolymerization thereof.
  • the glass transition temperature is preferably 50 ° C or lower, more preferably 40 ° C or lower, more preferably 30 ° C or lower, and further preferably 25 ° C or lower. Further, it is most preferably 20 ° C or less.
  • the elastic modulus at 25 ° C of the undercoat layer is preferably 1 to 1 OOOMPa, more preferably 5 to 800 MPa, and even more preferably 10 to 500 MPa.
  • the undercoat layer having a rough surface adheres the base material and the near-infrared absorbing layer by forming a near-infrared absorbing layer on the rough surface.
  • the undercoat layer having a rough surface can be easily formed by applying a polymer latex.
  • the average particle size of the latex is preferably 201 111 to 3 111, and more preferably 501 111 to 1 111.
  • Examples of the polymer having an affinity for the binder polymer of the near-infrared absorbing layer include acrylic resins, cellulose derivatives, gelatin, casein, starch, polybutyl alcohol, soluble nylon, and polymer latex.
  • two or more undercoat layers may be provided.
  • a solvent that swells the substrate, a matting agent, a surfactant, an antistatic agent, a coating aid, a hardening agent, and the like may be added.
  • a low refractive index layer is essential.
  • Refractive index of the low refractive index layer Is lower than the refractive index of the transparent support.
  • the refractive index of the low-refractive index layer is 1.20 to 1.55.
  • the force S is preferable, and 1.30 to 1.50 is more preferable.
  • the thickness of the low refractive index layer is preferably 50 to 400 nm, more preferably 50 to 200 nm.
  • the low refractive index layer is a layer made of a fluorine-containing polymer having a low refractive index (Japanese Patent Laid-Open Nos. 57-34526, 3-130103, 6-115023, 8-313702, 7-168004).
  • voids can be formed in the low refractive index layer as microvoids between the fine particles or within the fine particles.
  • the layer containing fine particles preferably has a porosity of 3 to 50% by volume, more preferably 5 to 35% by volume.
  • a layer having a high refractive index (medium ′ high refractive index layer) is preferably laminated.
  • the refractive index of the high refractive index layer is preferably 1.65-2.40, more preferably 1 ⁇ 70 to 2 ⁇ 20.
  • the refractive index of the middle refractive index layer is adjusted to be an intermediate value between the refractive index of the low refractive index layer and the refractive index of the high refractive index layer.
  • the refractive index of the middle refractive index layer is 1.50 to 1.90, preferably S, more preferably 1.55 to 1.70.
  • the thickness of the medium / high refractive index layer is preferably 51 111 to 100 111, more preferably lOnm lO ⁇ m, and most preferably 301 111 to 1 111.
  • the haze of the medium / high refractive index layer should be 5% or less. S is preferable, and 3% or less is more preferable, and 1% or less is most preferable.
  • the medium'high refractive index layer can be formed using a polymer binder having a relatively high refractive index.
  • polystyrene examples include polystyrene, styrene copolymer, polycarbonate, melamine resin, phenol resin, epoxy resin, polyurethane obtained by reaction of cyclic (alicyclic or aromatic) isocyanate and polyol. It is Polymers having other cyclic (aromatic, heterocyclic, alicyclic) groups and polymers having halogen atoms other than fluorine as substituents also have a high refractive index. Use a polymer formed by the polymerization reaction of a monomer that allows radical curing by introducing a double bond That's it.
  • inorganic fine particles may be dispersed in the polymer binder.
  • the refractive index of the inorganic fine particles is 1.80-2.80.
  • the inorganic fine particles are preferably formed from metal oxides or sulfides.
  • metal oxides or sulfides include titanium oxide (eg, rutile, rutile / anatase mixed crystal, anatase, amorphous structure), tin oxide, indium oxide, zinc oxide, zirconium oxide, and zinc sulfide.
  • titanium oxide, tin oxide, and indium oxide are particularly preferable.
  • the inorganic fine particles are mainly composed of oxides or sulfides of these metals, and can further contain other elements.
  • the main component means a component having the largest content (% by weight) among the components constituting the inorganic fine particles.
  • examples of other elements include Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P, and S.
  • An active inorganic polymer or the like can be used to form a middle-high refractive index layer.
  • the surface of the antireflection layer can be provided with an antiglare function (function of scattering incident light on the surface and preventing the scenery around the film from moving to the film surface).
  • an antiglare function function of scattering incident light on the surface and preventing the scenery around the film from moving to the film surface.
  • An antireflection layer having a function can be obtained.
  • An antireflection layer having an antiglare function generally has a haze of 3 to 30%.
  • the hard coat layer has a hardness higher than that of the transparent support.
  • the hard coat layer preferably contains a crosslinked polymer.
  • the hard coat layer can be formed using an acrylic, urethane, or epoxy polymer, oligomer, or monomer (for example, an ultraviolet spring curable resin).
  • a hard coat layer is formed from a silica-based material.
  • a lubricating layer may be formed on the surface of the antireflection layer (low refractive index layer).
  • the lubricating layer has a function of imparting slipperiness to the surface of the low refractive index layer and improving scratch resistance.
  • Lubrication layer is polio It can be formed using luganosiloxane (for example, silicone oil), natural wax, petroleum wax, higher fatty acid metal salt, fluorine-based lubricant or derivative thereof.
  • the thickness of the lubricating layer is preferably 2 to 20 nm.
  • the near-infrared absorbing layer, undercoat layer, antireflection layer, hard coat layer, lubricating layer and the like can be formed by a general coating method.
  • Application methods include dip coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, and etatrusion coating using a hopper (described in US Pat. No. 2681294).
  • Etc. Two or more layers may be formed by simultaneous application.
  • the same day temple application method ⁇ KOTSULE May, U.S. Patents 2761791, 2941898, 3508947, 3526528 and Yuji Harasaki "Coating Engineering", page 253 (published by Asakura Shoten in 1973) There is a description.
  • the optical filter of the present invention can be suitably used as a visibility correction filter for a CCD (for example, a photoelectric conversion element made of a silicon photodiode) in an imaging apparatus (image input apparatus).
  • a visibility correction filter for CCD includes a lid, a lens, a protective plate, etc., in addition to a visibility correction filter arranged alone in the optical path to the CCD.
  • imaging devices equipped with CCDs include video cameras, digital cameras, board cameras, color scanners, color fax machines, color copiers, and color videophones.
  • the incident light to the CCD (silicon photodiode) can be substantially limited to light in the visible region. As a result, accurate photometry ( (Exposure operation) can be performed, and the reproduction of the red component is not hindered.
  • the optical filter according to the present invention can be suitably used as a visibility correction filter for an imaging device (image input device) equipped with a CMOS image sensor or an artificial retina.
  • an imaging device image input device
  • CMOS image sensor and artificial retina equipped with the optical filter of the present invention and an imaging device including these, the same effects as those of the above-described CCD can be obtained.
  • 3 ⁇ 4] Can play fruit.
  • the optical filter of the present invention can be suitably used as a noise cut filter in an environment where an infrared communication device (communication device using light of 850 to 950 nm as a medium) is used.
  • an infrared communication device communication device using light of 850 to 950 nm as a medium
  • the near infrared source for example, a machine using near infrared rays such as an automatic door and a remote controller
  • the infrared ray from the source is cut off, so that Generation of noise can be surely prevented.
  • the optical filter of the present invention in front of the panel of the plasma display device or the liquid crystal panel display device, it is possible to efficiently cut near infrared rays emitted from the panel. As a result, there will be no malfunction of the remote control caused by near-infrared rays around the display device!
  • resin molded products are frequently used as parts in various fields such as automobile parts from the viewpoint of weight reduction and cost reduction. Further, from the viewpoint of increasing the productivity of the resin molded product, a method is often employed in which the resin molded product is divided into a plurality of parts in advance and these divided molded products are joined to each other.
  • the resin materials are joined by overlapping a transparent resin material that is transmissive to the laser and an absorbent resin material that is permeable to the laser, and then from the transparent resin material side. This is performed by a laser welding method in which the contact surfaces of the permeable resin material and the absorbent resin material are heated and melted by irradiating a laser, and the two are integrally bonded.
  • the laser that has passed through the permeable resin material reaches the contact surface of the absorbent resin material and is absorbed, and the laser absorbed in this contact surface accumulates as energy. Is done.
  • the contact surface of the absorbent resin material is heated and melted, and this absorption is performed.
  • the heat transfer from the contact surface of the absorptive resin material heats and melts the contact surface of the permeable resin material. In this state, if the contact surfaces of the permeable resin material and the absorbent resin material are pressure-bonded to each other, they can be joined together.
  • this material Since this material has good visible light transmittance, it can reduce the color tone difference from the laser-transmissible resin material and has a large molar extinction coefficient in absorption in the near-infrared region.
  • the resin composition having sufficient bonding strength can be provided by reliably welding the contact surfaces of the permeable resin material and the absorbent resin material.
  • This marking method by laser light irradiation is such that characters or illustrations that are irradiated with laser light are discolored by heat energy, and characters and illustrations can be identified by light scattering.
  • JP-A-9-302236 laser marking is possible by irradiating a resin composition comprising a leuco dye, a color-forming auxiliary component and a thermoplastic resin with a laser beam after molding. It is disclosed.
  • Japanese Patent Application Laid-Open No. 11 92632 discloses a technique for performing laser marking on the surface of a resin molded product by irradiating an epoxy resin containing a copper compound and a nickel compound as a color former with laser light. In this case, the marking is limited to black.
  • Japanese Patent Application Laid-Open No. 8-120133 discloses a resin composition capable of chromatic laser marking in which a compound such as titanium black is blended with a rubber reinforced bull-based resin. It is limited to Bull resin and its application development is limited.
  • the near-infrared absorbing material of the present invention has high! /, Visible light transmittance and high! /, And near-infrared absorbing ability, so that it can be marked with a low-power active energy ray and is used for highly transparent marking.
  • a composition can be provided.
  • clear, high-speed and high-precision characters and illustrations can be easily and quickly marked.
  • LEDs are currently used in various fields in RGB three colors with high efficiency and high brightness. However, it generates a relatively large amount of energy but generates a heat source.
  • the diode equipment has the problem that it is always exposed to high temperatures. The cause of heat generation is due to the radiant heat and infrared generation of the diode.
  • the near-infrared absorbing material of the present invention is excellent in near-infrared absorbing ability and has high visible light transparency, so that infrared rays can be cut without changing the emission color of the LED. In addition, because it has high heat resistance and high light resistance, the near-infrared absorption ability will not deteriorate even if this material is used for LEDs for a long time. If the near-infrared absorbing material of the present invention is used, heat generation due to light emission of the diode can be suppressed.
  • the optical filter of the present invention is preferably arranged as a display filter or a filter for a CCD or CMOS image sensor, and its arrangement method is not limited at all.
  • P-21 was synthesized by the same method as in Production Example 3 except that Compound 4 and bishydroxyphenylcyclohexane were used. Yield 80%
  • P-22 was synthesized in the same manner as in Production Example 3 except that compound 8 was used instead of compound 2. Yield 85%.
  • P-23 was synthesized in the same manner as in Production Example 3 except that Compound 9 was used instead of Compound 2. Yield 82%.
  • P-24 was synthesized in the same manner as in Production Example 3 except that Compound 10 was used instead of Compound 2. Yield 85%.
  • P-25 was synthesized in the same manner as in Production Example 3 except that Compound 11 was used instead of Compound 2. Yield 80%.
  • P-26 was synthesized in the same manner as in Production Example 3 except that Compound 12 was used instead of Compound 2. Yield 81%.
  • P-28 was synthesized in the same manner as in Production Example 11 except that Compound 9 was used instead of Compound 6. Yield 79%.
  • P-29 was synthesized in the same manner as in Production Example 11 except that compound 10 was used instead of compound 6. Yield 90%.
  • P-30 was synthesized in the same manner as in Production Example 11 except that Compound 11 was used instead of Compound 6. Yield 84%.
  • P-31 was synthesized in the same manner as in Production Example 11 except that compound 12 was used instead of compound 6. Yield 81%.
  • P-56 was synthesized in the same manner as in Production Example 3 using Compound 2 (20 mmol), Compound 6 (20 mmol) and 1,3 bis [2 (4 hydroxyphenyl) 2 propyl] benzene (20 mmol). Yield 67%
  • the mixture was heated and stirred at 80 ° C in DMF under atmosphere. After completion of the reaction, filtration is performed, and the filtrate is washed with water.
  • PP-5 was synthesized in the same manner as in Production Example 47, except that 1-bromo-4 trifluorobutane was used instead of 1 bromobutane. Yield 41%.
  • PP-10 was synthesized in the same manner as in Production Example 47, except that 1-bromo-2-ethoxyethane was used instead of 1-bromobutane. Yield 31%.
  • PP-11 was synthesized in the same manner as in Production Example 47 except that trimethylsilyl chloride was used in place of 1-bromobutane. Yield 51%.
  • ⁇ -35 was synthesized in the same manner as in Production Example 71 except that ⁇ -black benzenethiol was used instead of ⁇ -methylbenzenethiol. Yield 33%.
  • the molecular weight was measured using a high-speed GPC manufactured by Tosoh Corporation; HLC8120GPC with a solvent THF and UV detection at 254 nm (polystyrene conversion).
  • the near-infrared absorption wavelength was measured with a spectrophotometer V-570 manufactured by JASCO.
  • Table 6 shows SP values in various solvents. (Hideki Yamamoto, “SP Value Fundamentals' Application and Calculation Method”, Information Organization Co., Ltd., April 3, 2006, 4th edition) No.8;! -84)
  • Comparative Compound 1 Comparative Compound 2 (see the publication of JP-A-2-264788 for the production method), Comparative Compound 3 (see US Pat. No. 5,089,585 for the production method) and some of the present invention
  • Table 7 shows the solubility of near-infrared absorbing materials in toluene and ethyl acetate. The solubility test was conducted as follows. That is, the materials and the solvent were added to the sample bottle, stirred for a whole day and night at various concentrations, and the solubility in various solvents was examined.
  • the improvement of the solubility with the near-infrared absorbing material of the present invention is 1 — [CH] — X 2 — Ar 1 — Y— Ar 2 — X 3 — [CH] — X 4 —
  • Table 8 shows the solubility of Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and several near-infrared absorbing materials of the present invention in various solvents.
  • the solubility of near-infrared absorbing material is less than 0.01 wt%
  • X is 0.01 wt% or more and less than 0.20 wt%
  • ⁇ is 0.2 wt% or more and less than 1.0 wt% is ⁇
  • 1. 0wt% or more is marked as ⁇ .
  • MEK represents methyl ethyl ketone
  • T represents toluene
  • E represents ethyl acetate
  • Comparative Compound 1 Comparative Compound 2 and Comparative Compound 3 have SP value of 7.0 ⁇ It can be seen that ⁇ ⁇ 9.0, 0.1 ⁇ ⁇ 5.5, and 0.1 ⁇ ⁇ 5.0 are not satisfied. Dph
  • substituted or unsubstituted phenylene and alkylene groups improve solubility in nonpolar solvents, resulting in ester groups and carbonyl groups.
  • a polar group such as an imino group improves the solubility in a polar solvent! For example, in P-1, it is found that 7 ⁇ 0 ⁇ ⁇ 9.0
  • Table 9 shows the Haze value and transmittance (% T) at the near-infrared maximum absorption wavelength ( ⁇ max) of this film. The Haze value was measured with a Haze Meter NDH2000 manufactured by NIPPONN DENSHOKU.
  • Comparative compound 1, comparative compound 2, comparative compound 3, comparative compound 4, P-1, P-2, P-6, P-38, P-56, P-62 are acrylic adhesives with a solid content of 25% ( Monomer composition: 60% butyl acrylate, 30% isobutyl acrylate, 3% acrylic acid, 7% hexyl acrylate 7%, solvent composition: 80% ethyl acetate, 20% toluene) After mixing at 0%, the film was applied to a PET film with a film thickness of 20 m, dried at 90 ° C for 2 minutes, and the adhesive surface was further laminated with a PET film. Table 10 shows the Haze value, visible light, and ⁇ max transmittance for this film. The Haze value was determined by the same method as in Example 4. Visible light and ⁇ max transmittance were measured with a spectrophotometer V-570 manufactured by JASCO.
  • the visible light transmittance is the average transmittance at 450 nm to 650 nm
  • ⁇ max is the maximum absorption wavelength.
  • the adhesive film containing Comparative Compound 4 has a low Haze value, it is a structural material obtained by extending an olefin resin from a dye for a long time, so that the weight ratio of the near-infrared absorbing portion is small. Therefore, since the film containing this is further diluted with resin, the near-infrared absorption capacity of max is weak. In other cases, it can be seen from Table 10 that the higher the compatible film, the lower the Haze value, the higher the visible light transmittance, and the higher the absorption rate at ⁇ max.
  • Example 5 The film of Example 5 was tested under the conditions of humidity 95%, temperature 80 ° C., and 48 hours. Table 11 shows the Haze values before and after and the transmittance change ⁇ % H directly at the maximum absorption wavelength.
  • Example 5 The film of Example 5 was tested at a temperature of 80 ° C. for 500 hours, and Table 12 shows the before and after Haze values and the transmittance change ⁇ % T at the maximum absorption wavelength.
  • UV-absorbing PET film (Tijin Tetron Film, manufactured by Teijin DuPont Film Co., Ltd.) is mounted, and a 24-hour light resistance test is performed with xenon—100 W / m 2 , temperature 60%, humidity 60%.
  • Table 13 shows the Haze value before and after the test and the transmittance change ⁇ % T at the maximum absorption wavelength.
  • the near-infrared absorbing material of the present invention has a SP length of 7.0 ⁇ 6 ⁇ 9.0, 0.1 ⁇ by adjusting the functional group used in the near-infrared absorbing material. ⁇ ⁇ 5.5, 0.1 ⁇ dph
  • This film was subjected to a heat resistance test at 80 ° C. for 500 hours, and Table 14 shows the Haze value, transmittance change ( ⁇ % T) and color change Ay value at 850 nm and lOOOnm.
  • the Haze value and ⁇ % T were determined in the same manner as in Example 5, and the chromaticity change Ay value was measured with a MINOLTA chromaticity meter CR-300.
  • Example 10 When the film prepared in Example 10 was tested under the durability test conditions used in Example 6 and Example 8, the same results as in Example 10 were obtained.
  • Comparative Compound 1 Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, P—1, P—2, P—6, P—38, P—56, P—62 2.5%, Comparative Compound 5, Comparison Compound 6 or PP-2, PP-3, PP-5, PP-16, PP-20, PP-30, 3.0%, solid content 25% acrylic adhesive (monomer composition: butyl acrylate 60% , Isobutyl acrylate 30%, Acrylic acid 3%, Acrylic acid 2-ethylhexyl 7%, Solvent composition: Ethyl acetate 80%, Toluene 20%) After coating and drying at 90 ° C for 2 minutes, the adhesive surface was further laminated with PET film.
  • acrylic adhesive monomer composition: butyl acrylate 60% , Isobutyl acrylate 30%, Acrylic acid 3%, Acrylic acid 2-ethylhexyl 7%, Solvent composition: Ethyl acetate 80%, Toluene 20%
  • Table 15 shows the Haze value, transmittance change ( ⁇ % ⁇ ) and color change Ay value at 850 nm and lOOOnm.
  • the Haze value and ⁇ % ⁇ were determined in the same manner as in Example 5.
  • the chromaticity change Ay value was measured with a MINOLTA color chromatograph CR-300.
  • Example 12 When the film prepared in Example 12 was tested under the durability test conditions used in Example 6 and Example 8, the same results as in Example 12 were obtained.
  • P-1 and P-1 and its by-product PP-45 mixture have the same durability with no change in initial Haze value. It can be seen that when only the load of PP-45 is used, high haze is obtained and durability is also lowered. That is, P-1, P-1 and PP-45 (P-1 Mixtures of by-products) can be used without distinction.
  • Example 14 PP-44 (near infrared maximum absorption wavelength: 1, OOOnm) was further added to 2. Owt.

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Abstract

Matière pouvant absorber des rayons du proche infrarouge ayant un motif récurrent représenté par la formule générale (1) ; et composition pouvant absorber des rayons du proche infrarouge comprenant la matière. [Formule générale (1)] Dans la formule, M représente un atome de métal ; l'un de R1 à R20 représente une liaison directe, un autre de R1 à R20 représente un groupe divalent représenté par la formule générale (2) et les autres représentent indépendamment un atome d'hydrogène ou un substituant. [Formule générale 2] Dans la formule, X1 à X4 représentent indépendamment une liaison directe ou un groupe divalent tel que -O-, -S-, -COO-, -OCO-, -SO2- et -CO- ; Ar1 et Ar2 représentent indépendamment un groupe arylène ou un groupe hétéroarylène ; n représente un nombre entier naturel ; et Y représente une liaison directe ou un groupe divalent tel qu'un groupe alkylène, -O-, -S-, -NH-, -COO-, -SO2- et -CO-.
PCT/JP2007/065767 2006-09-08 2007-08-10 Matière pouvant absorber des rayons du proche infrarouge, composition pouvant absorber des rayons du proche infrarouge comprenant la matière et utilisation de celles-ci Ceased WO2008029594A1 (fr)

Applications Claiming Priority (6)

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JP2006-243716 2006-09-08
JP2006243716 2006-09-08
JP2007-030053 2007-02-09
JP2007030053 2007-02-09
JP2007161997 2007-06-20
JP2007-161997 2007-06-20

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489399B1 (en) * 2000-07-31 2002-12-03 Molecular Optoelectronics Corp. Dye-appended polymers for broadband fiber optic devices
JP2006119383A (ja) * 2004-10-21 2006-05-11 Osaka Gas Co Ltd 赤外線吸収フィルターおよび赤外線吸収パネル
WO2007018065A1 (fr) * 2005-08-10 2007-02-15 Toyo Ink Mfg. Co., Ltd. Materiau absorbant dans le proche infrarouge et son utilisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489399B1 (en) * 2000-07-31 2002-12-03 Molecular Optoelectronics Corp. Dye-appended polymers for broadband fiber optic devices
JP2006119383A (ja) * 2004-10-21 2006-05-11 Osaka Gas Co Ltd 赤外線吸収フィルターおよび赤外線吸収パネル
WO2007018065A1 (fr) * 2005-08-10 2007-02-15 Toyo Ink Mfg. Co., Ltd. Materiau absorbant dans le proche infrarouge et son utilisation

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