WO2015025779A1 - Filtre optique et dispositif utilisant un filtre optique - Google Patents

Filtre optique et dispositif utilisant un filtre optique Download PDF

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Publication number
WO2015025779A1
WO2015025779A1 PCT/JP2014/071311 JP2014071311W WO2015025779A1 WO 2015025779 A1 WO2015025779 A1 WO 2015025779A1 JP 2014071311 W JP2014071311 W JP 2014071311W WO 2015025779 A1 WO2015025779 A1 WO 2015025779A1
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Prior art keywords
resin
group
carbon atoms
optical filter
hydrocarbon group
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PCT/JP2014/071311
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English (en)
Japanese (ja)
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勝也 長屋
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Jsr株式会社
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Priority to KR1020167004029A priority Critical patent/KR102205190B1/ko
Priority to JP2015532830A priority patent/JP6398980B2/ja
Priority to CN201480045553.7A priority patent/CN105531608B/zh
Publication of WO2015025779A1 publication Critical patent/WO2015025779A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/26—Reflecting filters
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention relates to an optical filter and an apparatus using the optical filter. Specifically, the present invention relates to an optical filter containing a specific solvent-soluble dye compound, and a solid-state imaging device and a camera module using the optical filter.
  • a solid-state image pickup device such as a video camera, a digital still camera, or a mobile phone with a camera function uses a CCD or CMOS image sensor, which is a solid-state image pickup device for a color image.
  • Silicon photodiodes that are sensitive to near infrared rays that cannot be sensed by the eyes are used. These solid-state image sensors need to be corrected for visibility so that they appear natural to the human eye.
  • Optical filters that selectively transmit or cut light in a specific wavelength region (for example, near-infrared cut) Filter) is often used.
  • a near-infrared cut filter those manufactured by various methods are conventionally used.
  • a near-infrared cut filter in which a transparent resin is used as a base material and a near-infrared absorbing dye is contained in the transparent resin is known (see, for example, Patent Document 1), and in particular, a phthalocyanine compound is used as a near-infrared absorbing dye.
  • the near-infrared cut filter used is widely known (see, for example, Patent Document 2).
  • ordinary phthalocyanine compounds often have an absorption maximum wavelength of less than 650 to 700 nm, and the absorption maximum wavelength can be shifted to a wavelength range (700 to 800 nm) that is particularly suitable for use as a solid-state imaging device.
  • a wavelength range 700 to 800 nm
  • the visible transmittance on the short wavelength side in the vicinity of 430 to 460 nm is remarkably lowered.
  • a general phthalocyanine compound is likely to be in an H association state in which rings are stacked in a resin or the like.
  • a broad waveform having a weak absorption intensity near the absorption maximum is obtained as in the spectrum described in Example 1 of JP2013-083915A (Patent Document 4).
  • Patent Document 4 the optical characteristics required for solid-state imaging device applications may not be achieved.
  • An object of the present invention is to improve the drawbacks of conventional optical filters such as near-infrared cut filters, and the near-infrared absorbing dye has sufficient absorption intensity in the wavelength region near 700 to 750 nm and is short.
  • An object of the present invention is to provide an optical filter having excellent transmittance in a visible wavelength region on the wavelength side, and an apparatus using the optical filter.
  • the present inventors have achieved a target absorption maximum wavelength and absorption strength in a resin by applying a phthalocyanine compound having a specific structure.
  • the inventors have found that an optical filter having excellent infrared absorption characteristics and visible transmittance can be obtained, and have completed the present invention. Examples of embodiments of the present invention are shown below.
  • An optical device comprising: a transparent resin substrate containing a compound (A) represented by the following formula (I); and a near-infrared reflective film formed on at least one surface of the substrate. filter.
  • M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a substituted metal atom containing a trivalent or tetravalent metal atom
  • a plurality of R a independently represents L 1
  • a plurality of R b s independently represent a hydrogen atom, a halogen atom, L 1 or —SO 2 —L 2
  • L 1 is below L a
  • L 2 represents a following L a, L b, L c , L d or L e
  • Halogen-substituted alkyl group alicyclic hydrocarbon group having 3 to 14 carbon atoms, aromatic hydrocarbon group having 6 to 14 carbon atoms, heterocyclic group having 3 to 14 carbon atoms, and alkoxy group having 1 to 12 carbon atoms It may have at least one substituent L selected from the group consisting of
  • M is a divalent transition metal, a trivalent or tetravalent metal halide belonging to groups 4 to 12 and 4th to 5th of the periodic table, or 4 R a is independently an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, or a cyclohexyl group, and R b is independently a hydrogen atom , A fluorine atom, an alkyl group having 1 to 10 carbon atoms, a cyclopentyl group, a cyclohexyl group, or —SO 2 —L 2 , and L 2 is an alkyl group having 1 to 6 carbon atoms and an aromatic carbon atom having 6 to 12 carbon atoms.
  • the transparent resin constituting the transparent resin substrate is a cyclic olefin resin, aromatic polyether resin, polyimide resin, fluorene polycarbonate resin, fluorene polyester resin, polycarbonate resin, polyamide resin, poly Allylate resin, polysulfone resin, polyethersulfone resin, polyparaphenylene resin, polyamideimide resin, polyethylene naphthalate resin, fluorinated aromatic polymer resin, (modified) acrylic resin, epoxy resin
  • a solid-state imaging device comprising the optical filter according to any one of items [1] to [5].
  • a camera module comprising the optical filter according to any one of items [1] to [5].
  • M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a substituted metal atom containing a trivalent or tetravalent metal atom
  • a plurality of R a independently represents L 1
  • a plurality of R b s independently represent a hydrogen atom, a halogen atom, L 1 or —SO 2 —L 2
  • L 1 is below L a
  • L 2 represents a following L a, L b, L c , L d or L e
  • Halogen-substituted alkyl group alicyclic hydrocarbon group having 3 to 14 carbon atoms, aromatic hydrocarbon group having 6 to 14 carbon atoms, heterocyclic group having 3 to 14 carbon atoms, and alkoxy group having 1 to 12 carbon atoms It may have at least one substituent L selected from the group consisting of
  • an optical filter that is less dependent on the incident angle, has excellent light resistance, near-infrared absorption characteristics near 700 to 750 nm, and transmittance characteristics in the visible wavelength region.
  • FIG. 1A is a schematic diagram showing a method for measuring the transmittance when measured from the vertical direction of the optical filter.
  • FIG. 1B is a schematic diagram illustrating a method of measuring the transmittance when measured from an angle of 30 ° with respect to the vertical direction of the optical filter.
  • An optical filter according to the present invention includes a transparent resin substrate containing a phthalocyanine compound (compound (A)) represented by a specific structure, and a near-infrared reflective film formed on at least one surface of the substrate.
  • the transparent resin substrate constituting the optical filter of the present invention may be a single layer or a multilayer (in the case of a multilayer, for example, a cured resin on a base resin substrate).
  • the transmittance at the absorption maximum wavelength is preferably 10% or less, and more preferably 8% or less.
  • the substrate can selectively and efficiently cut near infrared rays, and a near infrared reflecting film on the surface of the transparent resin substrate.
  • the film is formed, it is possible to reduce the incident angle dependency of the optical characteristics in the visible wavelength to near infrared wavelength region.
  • the average transmittance of the substrate when the thickness of the resin substrate containing the compound (A) is 100 ⁇ m is preferably 50% or more, preferably It may be necessary to be 65% or more.
  • the thickness of the resin substrate can be appropriately selected according to the desired application, and is not particularly limited. However, it is preferable to adjust the substrate so that the incident angle dependency is improved as described above, and more preferably. Is 30 to 250 ⁇ m, more preferably 40 to 200 ⁇ m, particularly preferably 50 to 150 ⁇ m.
  • the optical filter using the substrate can be reduced in size and weight, and can be suitably used for various applications such as a solid-state imaging device.
  • the resinous substrate is used in a lens unit such as a camera module, it is preferable because a low-profile lens unit can be realized.
  • the resin substrate further comprises at least one near infrared absorbing dye (X) selected from the group consisting of a squarylium compound, a phthalocyanine compound other than the compound (A), and a cyanine compound.
  • X near infrared absorbing dye
  • the incident angle dependency in the visible wavelength region to the near infrared wavelength region can be further reduced, the absorption band waveform can be further sharpened, and a wide viewing angle can be obtained.
  • a filter can be obtained.
  • the compound (A) and the near-infrared absorbing dye (X) may be contained in the same layer or in different layers.
  • a form in which both the compound (A) and the near-infrared absorbing dye (X) are included in the base resin substrate can be mentioned, and when included in separate layers, for example, the form by which the layer containing the said near-infrared absorption pigment
  • the compound (A) and the near-infrared absorbing dye (X) are more preferably contained in the same layer.
  • the compound (A) and the near-infrared absorbing dye are contained in a case where they are contained in separate layers. It becomes easier to control the content ratio of (X).
  • the compound (A) is a phthalocyanine compound represented by the following formula (I).
  • M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a substituted metal atom containing a trivalent or tetravalent metal atom
  • a plurality of R a independently represents L 1
  • a plurality of R b s independently represent a hydrogen atom, a halogen atom, L 1 or —SO 2 —L 2
  • L 1 is below L a
  • L 2 represents a following L a, L b, L c , L d or L e
  • Halogen-substituted alkyl group alicyclic hydrocarbon group having 3 to 14 carbon atoms, aromatic hydrocarbon group having 6 to 14 carbon atoms, heterocyclic group having 3 to 14 carbon atoms, and alkoxy group having 1 to 12 carbon atoms It may have at least one substituent L selected from the group consisting of
  • L a ⁇ L e is the total number of carbon atoms including the substituent is preferably respectively 50 or less, still more preferably a few 40 or less carbon atoms, and particularly preferably 30 or less carbon atoms.
  • the number of carbon atoms is larger than this range, it may be difficult to synthesize the dye, and the absorption intensity per unit weight tends to decrease.
  • the aliphatic hydrocarbon group L a and 1 to 12 carbon atoms in L such as a methyl group (Me), ethyl (Et), n-propyl group (n-Pr), isopropyl (i-Pr ), N-butyl group (n-Bu), sec-butyl group (s-Bu), tert-butyl group (t-Bu), pentyl group, hexyl group, octyl group, nonyl group, decyl group, dodecyl group, etc.
  • Me methyl group
  • Et ethyl
  • i-Pr isopropyl
  • n-Bu N-butyl group
  • s-Bu sec-butyl group
  • t-Bu tert-butyl group
  • pentyl group hexyl group
  • octyl group nonyl group
  • decyl group dodecyl
  • Alkyl groups such as vinyl group, 1-propenyl group, 2-propenyl group, butenyl group, 1,3-butadienyl group, 2-methyl-1-propenyl group, 2-pentenyl group, hexenyl group and octenyl group
  • alkynyl groups such as ethynyl group, propynyl group, butynyl group, 2-methyl-1-propynyl group, hexynyl group and octynyl group.
  • Examples of the halogen-substituted alkyl group having 1 to 12 carbon atoms in L b and L include, for example, a trichloromethyl group, a trifluoromethyl group, a 1,1-dichloroethyl group, a pentachloroethyl group, a pentafluoroethyl group, a heptachloro group. Mention may be made of propyl and heptafluoropropyl groups.
  • Examples of the alicyclic hydrocarbon group having 3 to 14 carbon atoms in L c and L include, for example, a cycloalkyl group such as a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group; a norbornane group and an adamantane group And polycyclic alicyclic groups such as
  • Examples of the aromatic hydrocarbon group having 6 to 14 carbon atoms in L d and L include, for example, phenyl group, tolyl group, xylyl group, mesityl group, cumenyl group, 1-naphthyl group, 2-naphthyl group, anthracenyl group, Mention may be made of phenanthryl, acenaphthyl, phenalenyl, tetrahydronaphthyl, indanyl and biphenylyl groups.
  • heterocyclic group having 3 to 14 carbon atoms in Le and L examples include, for example, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiazole, thiadiazole, indole, indoline, indolenine, and benzofuran.
  • L a preferably a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, sec- butyl group, tert- butyl group, a pentyl group, a hexyl group, an octyl group, 4-phenylbutyl 2-cyclohexylethyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and hexyl.
  • L b is preferably a trichloromethyl group, a pentachloroethyl group, a trifluoromethyl group, a pentafluoroethyl group, or a 5-cyclohexyl-2,2,3,3-tetrafluoropentyl group, more preferably a trichloromethyl group.
  • L c is preferably a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-ethylcyclohexyl group, a cyclooctyl group, or a 4-phenylcycloheptyl group, and more preferably a cyclopentyl group, a cyclohexyl group, or a 4-ethylcyclohexyl group. It is.
  • the L d is preferably a phenyl group, 1-naphthyl group, 2-naphthyl group, tolyl group, xylyl group, mesityl group, cumenyl group, 3,5-di-tert-butylphenyl group, 4-cyclopentylphenyl group. 2,3,6-triphenylphenyl group, 2,3,4,5,6-pentaphenylphenyl group, more preferably phenyl group, tolyl group, xylyl group, mesityl group, cumenyl group, 2,3 , 4,5,6-pentaphenylphenyl group.
  • L e preferably furan, thiophene, pyrrole, indole, indoline, indolenine, benzofuran, benzothiophene, consisting morpholine group, more preferably furan, thiophene, pyrrole, consisting morpholine group.
  • L a ⁇ L e is further halogen atom, a sulfo group, a hydroxyl group, a cyano group, a nitro group, a carboxy group, have at least one atom or group selected from the group consisting of a phosphate group and an amino group May be.
  • Examples include 4-sulfobutyl, 4-cyanobutyl, 5-carboxypentyl, 5-aminopentyl, 3-hydroxypropyl, 2-phosphorylethyl, 6-amino-2,2-dichloro.
  • examples of the monovalent metal atom include Li, Na, K, Rb, and Cs.
  • the divalent metal atoms include Be, Mg, Ca, Ba, Ti, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Cu, Zn, Cd, Hg, Sn, Pb etc. are mentioned.
  • the substituted metal atom containing a trivalent metal atom includes Al—F, Al—Cl, Al—Br, Al—I, Ga—F, Ga—Cl, Ga—Br, Ga—I, In -F, In-Cl, In-Br, In-I, Tl-F, Tl-Cl, Tl-Br, Tl-I, Fe-Cl, Ru-Cl, Mn-OH and the like.
  • the substituted metal atom containing a tetravalent metal atom includes TiF 2 , TiCl 2 , TiBr 2 , TiI 2 , ZrCl 2 , HfCl 2 , CrCl 2 , SiF 2 , SiCl 2 , SiBr 2 , SiI 2 , GeF 2 , GeCl 2 , GeBr 2 , GeI 2 , SnF 2 , SnCl 2 , SnBr 2 , SnI 2 , Zr (OH) 2 , Hf (OH) 2 , Mn (OH) 2 , Si (OH) 2 , Ge ( OH) 2 , Sn (OH) 2 , TiR 2 , CrR 2 , SiR 2 , GeR 2 , SnR 2 , Ti (OR) 2 , Cr (OR) 2 , Si (OR) 2 , Ge (OR) 2 , Sn (OR) 2 (R represents an aliphatic group or an aromatic group),
  • M examples include groups 4 to 12 in the periodic table, and 4th to 5th cycles. Belongs to divalent transition metals, trivalent or Is preferably a tetravalent metal halide or a tetravalent metal oxide. Among them, Cu, Ni, Co, Zn, TiO and VO are particularly preferable because they can achieve particularly high visible light transmittance and dye stability. More preferred are Cu and VO.
  • R a is independently an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, or A cyclohexyl group is preferred, an alkyl group having 1 to 10 carbon atoms is more preferred, and an alkyl group having 3 to 8 carbon atoms is particularly preferred.
  • R b is independently a hydrogen atom, a fluorine atom, an alkyl group having 1 to 10 carbon atoms, a cyclopentyl group, a cyclohexyl group, or —SO 2 —L from the viewpoint of ease of synthesis and stability of the compound (A).
  • 2 is preferably an alkyl group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a heterocyclic ring having 3 to 6 carbon atoms), preferably a hydrogen atom or 1 to More preferred is an alkyl group of 6.
  • a method of synthesizing the compound (A) by a cyclization reaction of a phthalonitrile derivative represented by the following formula (II) is generally known.
  • the resulting phthalocyanine compound is represented by the following formula (II-1) This is a mixture of four isomers such as (II-4).
  • II-1 This is a mixture of four isomers such as (II-4).
  • II-4 isomers such as (II-4).
  • isomers can be separated and used as necessary, but in the present invention, the isomer mixture is collectively handled.
  • Specific examples of the compound (A) are not particularly limited as long as the conditions described in the above formula (I) are satisfied.
  • Table 1 which has a basic skeleton represented by the following formula (I-1) And the compounds (a-1) to (a-35) described.
  • the compound (A) may be synthesized by a generally known method.
  • Japanese Patent No. 4081149 “Phthalocyanine—Chemistry and Function” (IPC, 1997), Japanese Patent Laid-Open No. 2-138382. It can be synthesized with reference to the method described in the publication.
  • the content of the compound (A) in the resin layer is preferably from 0.01 to 5.0 parts by weight, more preferably from 0.1 to 5.0 parts by weight, based on 100 parts by weight of the transparent resin used when the resin substrate is manufactured. It is 02 to 3.5 parts by weight, particularly preferably 0.03 to 2.5 parts by weight.
  • the content of the compound (A) is within the above range, both good near infrared absorption characteristics and high visible light transmittance can be achieved.
  • the near-infrared absorbing dye (X) is at least one selected from the group consisting of a squarylium compound, a phthalocyanine compound, and a cyanine compound, and particularly preferably contains a squarylium compound.
  • the absorption maximum wavelength of the near-infrared absorbing dye (X) is preferably 620 nm or more, more preferably 650 nm or more, particularly preferably 670 nm or more, and preferably less than 800 nm, more preferably 750 nm or less, particularly preferably 730 nm or less.
  • the compound (A) contained at the same time has an absorption maximum on a shorter wavelength side than the absorption maximum wavelength.
  • the absorption maximum wavelength is in such a wavelength range, the waveform of the absorption band can be further sharpened, the absorption band due to the near-infrared absorbing dye can be sufficiently widened, and the incident angle dependent improvement performance and ghosting can be improved. A reduction effect can be achieved.
  • the content of the near-infrared absorbing dye (X) in the resin layer is preferably 0.01 to 5.0 parts by weight, more preferably 100 parts by weight of the transparent resin used when the resin substrate is manufactured. Is 0.02 to 3.5 parts by weight, particularly preferably 0.03 to 2.5 parts by weight. When the content of the near-infrared absorbing dye is within the above range, both good near-infrared absorption characteristics and high visible light transmittance can be achieved.
  • the squarylium-based compound preferably includes at least one selected from the group consisting of a squarylium-based compound represented by the formula (III-1) and a squarylium-based compound represented by the formula (III-2).
  • R m , R n and Y satisfy the following condition (i) or (ii).
  • Condition (i) A plurality of R m each independently represents a hydrogen atom, a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, —L 1 or —NR e R f group.
  • R e and R f each independently represents a hydrogen atom, -L a , -L b , -L c , -L d, or -L e .
  • a plurality of R n each independently represents a hydrogen atom, a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, —L 1 or —NR g R h group.
  • R g and R h are each independently a hydrogen atom, -L a , -L b , -L c , -L d , -L e or -C (O) R i group (R i is -L a , Represents -L b , -L c , -L d or -L e ).
  • a plurality of Y each independently represents a —NR j R k group.
  • R j and R k each independently represents a hydrogen atom, -L a , -L b , -L c , -L d, or -L e .
  • L 1, L a, L b , L c, L d, L e is, L 1 defined in independent to the formula (I), L a, L b, L c, L d, and L e It is synonymous.
  • At least one of two R m on one benzene ring is bonded to Y on the same benzene ring to form a heterocycle having 5 or 6 member atoms containing at least one nitrogen atom; the heterocyclic ring may have a substituent, R m which is not involved in the formation of R n and the heterocyclic ring is the same meaning as R n and R m of the independently (i).
  • X is, -O -, - S -, - Se -, - N (R c) - or -C (R d R d) - a represents; plural R c is respectively Each independently represents a hydrogen atom, -L a , -L b , -L c , -L d or -L e ; a plurality of R d s independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxyl group, a cyano group, Represents a nitro group, a carboxy group, a phosphate group, —L 1 or —NR e R f group, and adjacent R d groups may be linked to form an optionally substituted ring; L a ⁇ L e, L 1 has the same meaning as L a ⁇ L e defined by formula (I), R e and R f have the same meanings as R
  • the left and right substituents bonded to the central four-membered ring of the squarylium-based compound may be the same or different, but it is preferable that they are the same because synthesis is easier.
  • the squarylium compound may be synthesized by a generally known method, for example, a method described in JP-A-1-228960, JP-A-2001-40234, JP-A-3196383, or the like. Etc. and can be synthesized.
  • phthalocyanine compound those having an arbitrary structure other than the compound (A) can be used.
  • Japanese Patent No. 4081149 and “phthalocyanine -chemistry and function” IPC, 1997). In the year).
  • cyanine compounds a compound having a generally known structure can be used, and for example, it can be synthesized by a method described in JP-A-2009-108267.
  • the resin substrate contains a transparent resin and the compound (A).
  • the transparent resin is not particularly limited as long as it does not impair the effects of the present invention. For example, it ensures thermal stability and moldability to a film, and dielectrics are formed by high-temperature deposition performed at a deposition temperature of 100 ° C. or higher.
  • Tg glass transition temperature
  • the glass transition temperature of the resin is 140 ° C. or higher because a film capable of depositing a dielectric multilayer film at a higher temperature can be obtained.
  • the total light transmittance (JIS K7105) of the resin plate is preferably 75 to 95%, more preferably 78 to 95. %, Particularly preferably 80 to 95% of the resin can be used. If a resin having a total light transmittance in such a range is used, the resulting substrate exhibits good transparency as an optical film.
  • the weight average molecular weight (Mw) in terms of polystyrene measured by a gel permeation chromatography (GPC) method of the transparent resin is usually 15,000 to 350,000, preferably 30,000 to 250,000.
  • the average molecular weight (Mn) is usually 10,000 to 150,000, preferably 20,000 to 100,000.
  • the transparent resin examples include cyclic olefin resins, aromatic polyether resins, polyimide resins, fluorene polycarbonate resins, fluorene polyester resins, polycarbonate resins, polyamide (aramid) resins, polyarylate resins, polysulfones. Resin, polyethersulfone resin, polyparaphenylene resin, polyamideimide resin, polyethylene naphthalate (PEN) resin, fluorinated aromatic polymer resin, (modified) acrylic resin, epoxy resin, allyl Examples include ester resins and silsesquioxane resins.
  • the cyclic olefin-based resin is obtained from at least one monomer selected from the group consisting of a monomer represented by the following formula (X 0 ) and a monomer represented by the following formula (Y 0 ).
  • a resin and a resin obtained by hydrogenating the resin are preferable.
  • R x1 to R x4 each independently represents an atom or group selected from the following (i ′) to (ix ′), and k x , mx and p x are each independently 0 Or represents a positive integer.
  • a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms (v ′) a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms (vi ′) polar group (excluding (iv ′))
  • R x1 and R x2 or R x3 and R x4 are bonded to each other to form a monocyclic or polycyclic hydrocarbon ring or heterocyclic ring (provided that R x1 to R which are not involved in the bond) x4 each independently represents an atom or group selected from (i ′) to (vi ′).
  • Ix ′ A monocyclic hydrocarbon ring or heterocycle formed by bonding R x2 and R x3 to each other (provided that R x1 and R x4 not involved in the bonding are each independently the above (i Represents an atom or group selected from ') to (vi').
  • R y1 and R y2 each independently represents an atom or group selected from the above (i ′) to (vi ′), or R y1 and R y2 are bonded to each other formed monocyclic or polycyclic alicyclic hydrocarbon, an aromatic hydrocarbon or heterocyclic, k y and p y are each independently 0 or a positive integer.
  • the aromatic polyether-based resin preferably has at least one structural unit selected from the group consisting of a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2).
  • R 1 to R 4 each independently represents a monovalent organic group having 1 to 12 carbon atoms, and a to d each independently represent an integer of 0 to 4.
  • the aromatic polyether resin further has at least one structural unit selected from the group consisting of a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4). Is preferred.
  • R 5 and R 6 each independently represent a monovalent organic group having 1 to 12 carbon atoms
  • Z represents a single bond, —O—, —S—, —SO 2 —,> C ⁇ O, —CONH—, —COO— or a divalent organic group having 1 to 12 carbon atoms
  • e and f each independently represent an integer of 0 to 4, and n represents 0 or 1.
  • R 7 , R 8 , Y, m, g and h are each independently synonymous with R 7 , R 8 , Y, m, g and h in the formula (2), and R 5 , R 6 , Z, n, e and f are independently the same as R 5 , R 6 , Z, n, e and f in the formula (3).
  • the polyimide resin is not particularly limited as long as it is a polymer compound containing an imide bond in a repeating unit.
  • the polyimide resin is synthesized by a method described in JP-A-2006-199945 and JP-A-2008-163107. can do.
  • the fluorene polycarbonate resin is not particularly limited as long as it is a polycarbonate resin containing a fluorene moiety, and can be synthesized by, for example, a method described in JP-A-2008-163194.
  • the fluorene polyester resin is not particularly limited and may be any polyester resin containing a fluorene moiety.
  • the fluorene polyester resin can be synthesized by a method described in JP 2010-285505 A or JP 2011-197450 A. it can.
  • the fluorinated aromatic polymer-based resin is not particularly limited, but at least one selected from the group consisting of an aromatic ring having at least one fluorine, an ether bond, a ketone bond, a sulfone bond, an amide bond, an imide bond, and an ester bond. Any polymer containing a repeating unit containing one bond may be used, and for example, it can be synthesized by the method described in JP-A-2008-181121.
  • ⁇ Commercial product ⁇ The following commercial products etc. can be mentioned as a commercial item of transparent resin.
  • Examples of commercially available cyclic olefin-based resins include Arton manufactured by JSR Corporation, ZEONOR manufactured by Zeon Corporation, APEL manufactured by Mitsui Chemicals, Inc., and TOPAS manufactured by Polyplastics Corporation.
  • Examples of commercially available polyethersulfone resins include Sumika Excel PES manufactured by Sumitomo Chemical Co., Ltd.
  • Examples of commercially available polyimide resins include Neoprim L manufactured by Mitsubishi Gas Chemical Co., Ltd.
  • Examples of commercially available polycarbonate resins include Pure Ace manufactured by Teijin Limited.
  • Examples of commercially available fluorene polycarbonate resins include Iupizeta EP-5000 manufactured by Mitsubishi Gas Chemical Co., Ltd.
  • Examples of commercially available fluorene polyester resins include OKP4HT manufactured by Osaka Gas Chemical Co., Ltd.
  • acrylic resin there can be cited NIPPON CATALYST ACRYVIEWER Co., Ltd.
  • Examples of commercially available silsesquioxane resins include Silplus manufactured by Nippon Steel Chemical Co., Ltd.
  • the resin substrate is a dye that absorbs near infrared rays other than the antioxidant, the near ultraviolet absorber, the compound (A) and the near infrared absorbing dye (X) (hereinafter “ It may also contain additives such as “other near-infrared absorbing dyes”), fluorescence quenchers, and metal complex compounds.
  • substrate can be made easy by adding a leveling agent and an antifoamer.
  • antioxidants examples include 2,6-di-t-butyl-4-methylphenol, 2,2′-dioxy-3,3′-di-t-butyl-5,5′-dimethyldiphenylmethane, and And tetrakis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane.
  • Examples of the near ultraviolet absorber include azomethine compounds, indole compounds, benzotriazole compounds, and triazine compounds.
  • Examples of the other near infrared absorbing dyes include dithiol dyes, diimonium dyes, porphyrin dyes, and croconium dyes. The structures of these dyes are not particularly limited, and generally known ones can be used as long as the effects of the present invention are not impaired.
  • additives may be mixed with a resin or the like when a resin substrate is manufactured, or may be added when a resin is manufactured.
  • the addition amount is appropriately selected according to the desired properties, but is usually 0.01 to 5.0 parts by weight, preferably 0.05 to 2.0 parts by weight, based on 100 parts by weight of the resin. Part.
  • the resin substrate can be formed by, for example, melt molding or cast molding, and if necessary, is manufactured by a method of coating a coating agent such as an antireflection agent, a hard coating agent and / or an antistatic agent after molding. be able to.
  • a coating agent such as an antireflection agent, a hard coating agent and / or an antistatic agent after molding.
  • the resin substrate is a method of melt-molding pellets obtained by melt-kneading a resin and a near-infrared absorbing dye; a method of melt-molding a resin composition containing a resin and a near-infrared absorbing dye; or It can be produced by a method of melt-molding pellets obtained by removing a solvent from a resin composition containing a near-infrared absorbing dye, a resin and a solvent.
  • the melt molding method include injection molding, melt extrusion molding, and blow molding.
  • the resin substrate is formed by casting a resin composition containing a near-infrared absorbing dye, a resin and a solvent on a suitable base material to remove the solvent; and a curable resin composition containing a near-infrared absorbing dye and a resin. It can also be produced by a method of applying on a suitable substrate, drying and curing, and the like.
  • the substrate examples include a glass plate, a steel belt, a steel drum, and a transparent resin (for example, a polyester film and a cyclic olefin resin film).
  • the resin substrate can be obtained by peeling from the base material, and unless the effect of the present invention is impaired, the laminate of the base material and the coating film is not peeled from the base material. It is good.
  • the optical component such as glass plate, quartz or transparent plastic is coated with the resin composition and the solvent is dried, or the curable composition is coated and cured and dried.
  • a resin substrate can also be formed directly on the component.
  • the amount of residual solvent in the resin substrate obtained by the above method should be as small as possible.
  • the amount of the residual solvent is preferably 3% by weight or less, more preferably 1% by weight or less, and still more preferably 0.5% by weight or less with respect to the weight of the resin substrate.
  • the amount of residual solvent is in the above range, a resin substrate can be obtained in which the deformation and characteristics are hardly changed and a desired function can be easily exhibited.
  • the near-infrared reflective film constituting the optical filter of the present invention is a film having the ability to reflect near-infrared light.
  • the near-infrared reflective film may be provided on one side of the resin substrate or on both sides. When it is provided on one side, it is excellent in production cost and manufacturability, and when it is provided on both sides, an optical filter having high strength and less warpage can be obtained.
  • the optical filter is applied to a solid-state imaging device, it is preferable that the optical filter has a smaller warp. Therefore, it is preferable to provide a near-infrared reflective film on both surfaces of the resin substrate.
  • Examples of the near-infrared reflective film include an aluminum vapor-deposited film, a noble metal thin film, a resin film in which metal oxide fine particles mainly containing indium oxide and containing a small amount of tin oxide are dispersed, a high refractive index material layer, and a low refractive index material.
  • a dielectric multilayer film in which layers are alternately stacked can be mentioned.
  • a dielectric multilayer film in which high refractive index material layers and low refractive index material layers are alternately laminated is more preferable.
  • a material having a refractive index of 1.7 or more can be used, and a material having a refractive index of usually 1.7 to 2.5 is selected.
  • examples of such materials include titanium oxide, zirconium oxide, tantalum pentoxide, niobium pentoxide, lanthanum oxide, yttrium oxide, zinc oxide, zinc sulfide, or indium oxide, and the like, and titanium oxide, tin oxide. And / or those containing a small amount of cerium oxide or the like (for example, 0 to 10% by weight with respect to the main component).
  • a material having a refractive index of 1.6 or less can be used, and a material having a refractive index of usually 1.2 to 1.6 is selected.
  • examples of such materials include silica, alumina, lanthanum fluoride, magnesium fluoride, and sodium hexafluoride sodium.
  • the method for laminating the high refractive index material layer and the low refractive index material layer is not particularly limited as long as a dielectric multilayer film in which these material layers are laminated is formed.
  • a body multilayer film can be formed.
  • each of the high refractive index material layer and the low refractive index material layer is usually preferably from 0.1 ⁇ to 0.5 ⁇ , where ⁇ (nm) is the near infrared wavelength to be blocked.
  • the value of ⁇ (nm) is, for example, 700 to 1400 nm, preferably 750 to 1300 nm.
  • the optical film thickness, the high refractive index material layer, and the low refractive index, where the product (n ⁇ d) of the refractive index (n) and the film thickness (d) is calculated by ⁇ / 4.
  • the thickness of each layer of the material layer becomes almost the same value, and there is a tendency that the blocking / transmission of a specific wavelength can be easily controlled from the relationship between the optical characteristics of reflection / refraction.
  • the total number of high refractive index material layers and low refractive index material layers in the dielectric multilayer film is preferably 5 to 60 layers, and more preferably 10 to 50 layers as a whole.
  • the surface hardness of the resin substrate or near-infrared reflective film is between the resin substrate and the near-infrared reflective film such as a dielectric multilayer film within a range not impairing the effects of the present invention.
  • Functional films such as an antireflection film, a hard coat film, and an antistatic film can be provided as appropriate for the purpose of improvement, chemical resistance improvement, antistatic and scratch removal.
  • the surface of the resin substrate or functional film is subjected to corona treatment, plasma treatment, etc.
  • the surface treatment may be performed.
  • the optical filter of the present invention has the resin substrate. For this reason, the optical filter of the present invention has excellent transmittance characteristics and is not restricted when used.
  • the compound (A) contained in the resin substrate has an absorption maximum at a wavelength of 700 to 800 nm, it can efficiently absorb near-infrared light. When combined with the near-infrared reflective film, the incident angle is increased. An optical filter with less dependency can be obtained.
  • a wavelength value (Xa) at which the transmittance is 50% when measured from the vertical direction of the optical filter in the wavelength range of 560 to 800 nm By using the resin substrate for an optical filter such as a near-infrared cut filter, a wavelength value (Xa) at which the transmittance is 50% when measured from the vertical direction of the optical filter in the wavelength range of 560 to 800 nm.
  • the absolute value of the difference from the wavelength value (Xb) at which the transmittance is 50% when measured from an angle of 30 ° with respect to the vertical direction of the optical filter, and the optical filter in the wavelength range of 560 to 800 nm The wavelength value (Za) at which the transmittance is 10% when measured from the vertical direction and the wavelength value at which the transmittance is 10% when measured from an angle of 30 ° with respect to the vertical direction of the optical filter.
  • the absolute value of the difference from (Zb) becomes small, the incident angle dependence of the absorption wavelength is small, and an optical filter having a wide viewing angle can be obtained even near the bottom of the transmission wavelength region.
  • the absolute value of the difference between (Xa) and (Xb) is preferably less than 20 nm, more preferably less than 15 nm, particularly preferably less than 10 nm, and the difference between (Za) and (Zb) The absolute value is preferably 18 nm or less, particularly preferably 15 nm or less.
  • the visible light transmittance is higher.
  • the average transmittance at a wavelength of 430 to 460 nm is preferably 81% or more, more preferably 83% or more, and particularly preferably 85% or more.
  • the average transmittance at wavelengths of 461 to 580 nm is preferably higher, preferably 85% or more, more preferably 88% or more, and particularly preferably 90% or more.
  • the transmittance in the near infrared wavelength region is low.
  • the light receiving sensitivity of the solid-state imaging device is relatively high in the wavelength region of 800 to 1000 nm.
  • the average transmittance at a wavelength of 800 to 1000 nm is preferably 15% or less, more preferably 10% or less, and particularly preferably 5% or less.
  • the average transmittance at a wavelength of 800 to 1000 nm is in this range, it is preferable because near infrared rays can be sufficiently cut and excellent color reproducibility can be achieved.
  • the optical filter of the present invention has a wide viewing angle and has excellent near-infrared cutting ability and the like. Therefore, it is useful for correcting the visibility of a solid-state imaging device such as a CCD or CMOS image sensor of a camera module.
  • a solid-state imaging device such as a CCD or CMOS image sensor of a camera module.
  • it is also useful as a heat ray cut filter attached to a glass plate of an automobile or a building.
  • the solid-state imaging device of the present invention includes the optical filter of the present invention.
  • the solid-state imaging device is an image sensor including a solid-state imaging device such as a CCD or a CMOS image sensor, and specifically includes a digital still camera, a mobile phone camera, a digital video camera, and the like.
  • the camera module of the present invention includes the optical filter of the present invention.
  • Parts means “parts by weight” unless otherwise specified.
  • the measurement method of each physical property value and the evaluation method of the physical property are as follows.
  • the molecular weight of the resin was measured by the following method (a) or (b) in consideration of the solubility of each resin in a solvent.
  • GPC gel permeation chromatography
  • Standard polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) were measured using a GPC apparatus (HLC-8220 type, column: TSKgel ⁇ -M, developing solvent: THF) manufactured by Tosoh Corporation.
  • the logarithmic viscosity was measured by the following method (c) instead of the molecular weight measurement by the said method.
  • (C) A part of the polyimide resin solution was added to anhydrous methanol to precipitate the polyimide resin, and filtered to separate from the unreacted monomer.
  • 0.1 g of polyimide obtained by vacuum drying at 80 ° C. for 12 hours is dissolved in 20 mL of N-methyl-2-pyrrolidone, and the logarithmic viscosity ( ⁇ ) at 30 ° C. is obtained by the following formula using a Canon-Fenske viscometer. Asked.
  • ⁇ ⁇ ln (t s / t 0) ⁇ / C t 0 : Flowing time of solvent t s : Flowing time of dilute polymer solution C: 0.5 g / dL ⁇ Glass transition temperature (Tg)> Using a differential scanning calorimeter (DSC6200) manufactured by SII Nano Technologies, Inc., the rate of temperature increase was measured at 20 ° C. per minute under a nitrogen stream.
  • the transmittance at the absorption maximum wavelength and the absorption maximum wavelength of the resin substrate, the transmittance at each wavelength region of the optical filter, (Xa), (Xb), (Za) and (Zb) are spectroscopic products manufactured by Hitachi High-Technologies Corporation. Measurement was performed using a photometer (U-4100).
  • permeability was measured using this spectrophotometer on the conditions that light injects perpendicularly with respect to a board
  • (Xb) or (Zb) it is measured using the spectrophotometer under the condition that light is incident at an angle of 30 ° with respect to the vertical direction of the filter.
  • the resin substrate was exposed to an indoor fluorescent lamp (illuminance of 1000 lux) for 500 hours, and the light resistance (environmental light resistance) of the near-infrared absorbing dye contained in the resin was evaluated.
  • the light resistance is fluorescence at a wavelength with the highest absorption intensity of the resin substrate (hereinafter referred to as “ ⁇ a”.
  • ⁇ a is a wavelength with the highest absorption intensity among them.
  • the pigment residual ratio (%) was calculated from the change in absorbance before and after exposure to the lamp and evaluated.
  • the dye residual ratio after exposure with a fluorescent lamp for 500 hours is preferably 85% or more, more preferably 90% or more, and particularly preferably 95% or more.
  • Dodec-3-ene hereinafter also referred to as “DNM”) 100 parts, 1-hexene (molecular weight regulator) 18 parts, and toluene (ring-opening polymerization solvent) 300 parts nitrogen-substituted reaction The vessel was charged and the solution was heated to 80 ° C.
  • the obtained resin A had a number average molecular weight (Mn) of 32,000, a weight average molecular weight (Mw) of 137,000, and a glass transition temperature (Tg) of 165 ° C.
  • the obtained resin B had a number average molecular weight (Mn) of 75,000, a weight average molecular weight (Mw) of 188,000, and a glass transition temperature (Tg) of 285 ° C.
  • resin C A part of this polyimide resin solution was poured into 1 L of methanol to precipitate the polyimide.
  • the IR spectrum of the obtained resin C was measured, 1704 cm -1 characteristic of imido group, absorption of 1770 cm -1 were observed.
  • Resin C had a glass transition temperature (Tg) of 310 ° C. and a logarithmic viscosity of 0.87.
  • the temperature was raised to 240 ° C. at a rate of 37.5 ° C./Hr, held at 240 ° C. and 150 Torr for 10 minutes, adjusted to 120 Torr over 10 minutes, held at 240 ° C. and 120 Torr for 70 minutes, Further, the pressure was adjusted to 100 Torr over 10 minutes and held at 240 ° C. and 100 Torr for 10 minutes. Thereafter, the polymerization reaction was carried out by stirring for 10 minutes under the conditions of 240 ° C. and 1 Torr or less at 40 ° C. over 1 Torr.
  • resin D polycarbonate resin
  • the precipitated reaction product was separated by filtration, washed with distilled water and methanol, and then dried under reduced pressure to obtain a fluorinated polyether ketone (hereinafter also referred to as “resin F”).
  • the obtained resin F had a number average molecular weight of 71,000 and a glass transition temperature (Tg) of 242 ° C.
  • Example 1 In a container, 100 parts by weight of the resin A obtained in Resin Synthesis Example 1, 0.06 parts by weight of the compound (a-12) described in Table 1 above as the compound (A) (absorption maximum wavelength 736 nm in dichloromethane), And methylene chloride was added to obtain a solution having a resin concentration of 20% by weight. Subsequently, the obtained solution was cast on a smooth glass plate, dried at 20 ° C. for 8 hours, and then peeled off from the glass plate. The peeled coating film was further dried at 100 ° C. under reduced pressure for 8 hours to obtain a substrate having a thickness of 0.1 mm, a length of 60 mm, and a width of 60 mm.
  • the spectral transmittance of this substrate was measured, and the absorption maximum wavelength of the resin substrate, the transmittance at the absorption maximum wavelength, and the dye residual ratio after the light resistance test were determined to be 736 nm, 2%, and 100%, respectively. .
  • the results are shown in Table 2.
  • a multilayer deposited film reflecting a near infrared ray at a deposition temperature of 100 ° C. [silica (SiO 2 : film thickness 83 to 199 nm) layer and titanium oxide (TiO 2 : film thickness 101 to 125 nm)
  • a multilayer deposited film [silica (SiO 2 : film thickness 77) reflecting near infrared rays at a deposition temperature of 100 ° C. is formed on the other surface of the substrate.
  • the average transmittance at wavelengths 430 to 460 nm is 87%, the average transmittance at wavelengths 461 to 580 nm is 91%, the average transmittance at wavelengths 800 to 1000 nm is 1% or less, and the absolute value
  • Table 2 The results are shown in Table 2.
  • Example 2 an optical filter having a thickness of 0.105 mm was produced in the same manner as in Example 1 except that the transparent resin, near-infrared absorbing dye, solvent, and film drying conditions shown in Table 2 were employed.
  • the evaluation results are shown in Table 2.
  • Table 2 the number of added parts of the resin is 100 parts by weight, and the concentration of the resin solution is 20% by weight.
  • the various compounds used in the examples and comparative examples are as follows.
  • Resin A Cyclic olefin resin (resin synthesis example 1)
  • Resin B Aromatic polyether resin (resin synthesis example 2)
  • Resin C Polyimide resin (resin synthesis example 3)
  • Resin D Fluorene polycarbonate resin (resin synthesis example 4)
  • Resin E Fluorene polyester resin (resin synthesis example 5)
  • Resin F Fluorinated polyether ketone (resin synthesis example 6)
  • Resin G Cyclic olefin resin “Zeonor 1420R” (manufactured by Nippon Zeon Co., Ltd.)
  • Resin H Cyclic olefin resin “APEL # 6015” (manufactured by Mitsui Chemicals, Inc.)
  • Resin I Polycarbonate resin “Pure Ace” (manufactured by Teijin Limited)
  • Resin J Polyethersulfone resin “Sumilite FS-1300” (Sumitom
  • Compound (X-2) A squarylium compound represented by the following formula (X-2) (maximum absorption wavelength in dichloromethane: 698 nm)
  • Compound (X-3) a cyanine compound represented by the following formula (X-3) (absorption maximum wavelength in dichloromethane: 681 nm)
  • Compound (X-5) phthalocyanine compound represented by the following formula (X-5) (absorption maximum wavelength in dichloromethane: 733 nm)
  • Solvent (1) Methylene chloride
  • Solvent (2) N, N-dimethylacetamide
  • Solvent (3) Ethyl acetate / toluene (weight ratio: 5/5)
  • Solvent (4) cyclohexane / xylene (weight ratio: 7/3)
  • Solvent (5) cyclohexane / methylene chloride (weight ratio: 99/1)
  • Solvent (6) N-methyl-2-pyrrolidone
  • Table 2 the film drying conditions of Examples and Comparative Examples are as follows. In addition, the coating film was peeled from the glass plate before drying under reduced pressure.
  • the optical filter of the present invention is a digital still camera, a mobile phone camera, a digital video camera, a personal computer camera, a surveillance camera, an automobile camera, a television, an in-vehicle device for a car navigation system, a portable information terminal, a video game machine, a mobile phone. It can be suitably used for game machines, fingerprint authentication system devices, digital music players, and the like. Furthermore, it can be suitably used as a heat ray cut filter or the like attached to glass or the like of automobiles and buildings.
  • Optical filter 2 Spectrophotometer 3: Light

Abstract

La présente invention concerne un filtre optique qui remédie aux inconvénients des filtres optiques conventionnels tels que les filtres bloquant les rayons infrarouges proches et qui contient un colorant absorbant les rayons infrarouges proches qui présente une intensité d'absorption suffisante dans une plage de longueurs d'onde proche de 700-750 nm, tout en présentant un excellent facteur de transmission, même dans une plage de longueurs d'onde visibles du côté des longueurs d'onde courtes ; et un dispositif qui utilise ce filtre optique. Un filtre optique selon la présente invention est caractérisé en ce qu'il comprend : un substrat en résine transparent qui contient un composé (A) représenté par la formule (I) ; et un film réfléchissant la lumière infrarouge proche qui est formé sur au moins une surface du substrat.
PCT/JP2014/071311 2013-08-20 2014-08-12 Filtre optique et dispositif utilisant un filtre optique WO2015025779A1 (fr)

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JP2015532830A JP6398980B2 (ja) 2013-08-20 2014-08-12 光学フィルターおよび光学フィルターを用いた装置
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WO2018225837A1 (fr) * 2017-06-08 2018-12-13 富士フイルム株式会社 Composition de résine, corps moulé en résine et procédé de production d'un corps moulé en résine
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JP6398980B2 (ja) 2018-10-03
KR20160045690A (ko) 2016-04-27
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CN105531608B (zh) 2020-03-06
KR102205190B1 (ko) 2021-01-20

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