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WO2019167876A1 - Filtre optique et dispositif utilisant le filtre optique - Google Patents

Filtre optique et dispositif utilisant le filtre optique Download PDF

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Publication number
WO2019167876A1
WO2019167876A1 PCT/JP2019/007035 JP2019007035W WO2019167876A1 WO 2019167876 A1 WO2019167876 A1 WO 2019167876A1 JP 2019007035 W JP2019007035 W JP 2019007035W WO 2019167876 A1 WO2019167876 A1 WO 2019167876A1
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WO
WIPO (PCT)
Prior art keywords
group
resin
optical filter
compound
organic pigment
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/007035
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English (en)
Japanese (ja)
Inventor
武志 茂木
嘉彦 安藤
達郎 三井
勝也 長屋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JSR Corp
Original Assignee
JSR Corp
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Filing date
Publication date
Application filed by JSR Corp filed Critical JSR Corp
Priority to KR1020207024301A priority Critical patent/KR102793514B1/ko
Priority to JP2020503489A priority patent/JP7207395B2/ja
Priority to CN201980011899.8A priority patent/CN111684320B/zh
Publication of WO2019167876A1 publication Critical patent/WO2019167876A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • 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
    • G02B5/26—Reflecting filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/28—Interference filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
    • G03B11/00—Filters or other obturators specially adapted for photographic purposes
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
    • H04N23/00—Cameras or camera modules comprising electronic image sensors; Control thereof
    • H04N23/50—Constructional details
    • H04N23/55—Optical parts specially adapted for electronic image sensors; Mounting thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/10—Integrated devices
    • H10F39/12—Image sensors

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 an organic pigment having absorption in a specific wavelength region, and a solid-state imaging device and a camera module using the optical filter.
  • a solid-state imaging 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 imaging device for color images.
  • CCD or CMOS image sensor silicon photodiodes having sensitivity to near infrared rays that cannot be sensed by human eyes at the light receiving portion 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 substrate and a near-infrared absorbing pigment is contained in the transparent resin is known (see, for example, Patent Document 1).
  • the near-infrared cut filter described in Patent Document 1 may not always have sufficient near-infrared absorption characteristics.
  • Patent Document 2 the present applicant uses a transparent resin substrate containing a near-infrared absorbing dye having an absorption maximum in a specific wavelength region, so that there is little change in optical characteristics even when the incident angle is changed, and A near-infrared cut filter having a high visible light transmittance is proposed.
  • Patent Document 3 discloses a near-infrared ray that uses a phthalocyanine dye having a specific structure to achieve both a high visible light transmittance and a long absorption maximum wavelength, both of which are conventional problems. It is described that a cut filter can be obtained.
  • the applied base material has a sufficiently strong absorption band in the vicinity of 700 nm, but in the near-infrared wavelength region of, for example, 900 to 1200 nm. Has almost no absorption. Therefore, light in the near-infrared wavelength region is cut almost only by the reflection of the dielectric multilayer film, but with such a configuration, slight stray light due to internal reflection in the optical filter and reflection between the optical filter and the lens is generated. When shooting in a dark environment, it may cause ghost and flare. In particular, in recent years, there has been a strong demand for high-quality cameras even for mobile devices such as smartphones, and conventional optical filters may not be used favorably.
  • an infrared shielding filter as in Patent Document 4 has been proposed as an optical filter using a base material having a wide absorption in the near infrared wavelength region.
  • a broad absorption in the near-infrared wavelength region is achieved mainly by applying a compound having a dithiolene structure, but the absorption intensity near 700 nm is not sufficient.
  • image degradation may occur due to color shading.
  • Patent Document 5 discloses a near-infrared cut filter having a near-infrared absorbing glass base material and a layer containing a near-infrared absorbing dye, but the color shading is sufficiently improved even with the configuration described in Patent Document 5. There was a case that could not be done.
  • FIG. 5 of Patent Document 5 shows an optical characteristic graph at 0 ° incidence and at 30 ° incidence, but the region of the skirt portion of the visible light transmission band (630 to 700 nm) even at 30 ° incidence. ) A large wavelength shift is observed.
  • the present inventors have examined the use of a dye having an absorption maximum in the near-infrared wavelength region of 900 to 1200 nm for the optical filter.
  • a dye having an absorption maximum in the near-infrared wavelength region of 900 to 1200 nm for the optical filter.
  • the above dyes sometimes have a problem of deterioration in optical properties due to low heat resistance and UV resistance.
  • the near-infrared absorptance in the 900 to 1200 nm wavelength region and the 430 to 580 nm wavelength region due to the deterioration of the pigment.
  • the desired spectral characteristics cannot be obtained. Therefore, it is important to improve heat resistance and UV resistance of a dye having an absorption maximum at 900 to 1200 nm.
  • Patent Documents 6 and 7 As a method for improving the heat resistance and UV resistance of the above-mentioned pigment, for example, a method using a pigment as a pigment (particle dispersed state) instead of a dye (dissolved state) is known (for example, Patent Documents 6 and 7). .
  • a near-infrared cut filter using a diimonium dye having a problem of heat resistance is used by dissolving the dye in a dispersion medium (toluene) and then dispersing it in a resin (dye).
  • the present invention achieves high levels of both color shading suppression and ghost suppression of camera images and transmittance characteristics in the visible light wavelength region, which could not be sufficiently achieved by conventional optical filters, and is exposed to high temperatures for a long time. It is an object of the present invention to provide an optical filter having good heat resistance that can maintain optical characteristics even in such a case.
  • the substrate has a layer containing an organic pigment having an absorption maximum in a specific wavelength region, and on at least one surface of the substrate.
  • a dielectric multilayer film By forming a dielectric multilayer film, it is possible to obtain an optical filter that can achieve near infrared cut characteristics, visible light transmittance, color shading suppression effect and ghost suppression effect while maintaining the transmittance in the visible light region. I found it.
  • the present inventors can obtain an optical filter excellent in heat resistance by maintaining the haze value at a very low level by making the organic pigment fine particles and making the average particle diameter in a specific range. I found. Examples of embodiments of the present invention completed based on these findings are shown below.
  • An optical filter having a base material satisfying the following requirement (a) and having a dielectric multilayer film on at least one surface of the base material: (A) It has a layer containing an organic pigment (S) having an absorption maximum in a wavelength region of 900 nm to 1200 nm.
  • R 1 is independently a hydrogen atom, a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a carboxy group, a phosphoric acid group, -SR i group, -SO 2 R i groups, -OSO 2 R i group or a group represented by L a ⁇
  • R 2 represents any one of R h and R 2 independently represents a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a nitro group, a carboxy group, a phosphate group, a —NR g R h group, a —SR i group, —SO 2 R i group, —OSO 2 R i group or any of the following L a to L h is represented, and R g and R h are each independently a hydrogen atom, —C (O) R i group or the following L a to L represents either e, R g
  • the substituent L is an aliphatic hydrocarbon group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms. At least one selected from the group consisting of a halogen-substituted alkyl group, an alicyclic hydrocarbon group having 3 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms and a heterocyclic group having 3 to 14 carbon atoms Yes, n represents an integer of 0 to 4, X represents an anion necessary for neutralizing the electric charge.
  • the transparent resin constituting the transparent resin layer is a cyclic polyolefin resin, an aromatic polyether resin, a polyimide resin, a fluorene polycarbonate resin, a fluorene polyester resin, a polycarbonate resin, a polyamide resin, or a polyarylate.
  • Resin polysulfone resin, polyethersulfone resin, polyparaphenylene resin, polyamideimide resin, polyethylene naphthalate resin, fluorinated aromatic polymer resin, (modified) acrylic resin, epoxy resin, Item characterized by being at least one resin selected from the group consisting of an allyl ester curable resin, a silsesquioxane ultraviolet curable resin, an acrylic ultraviolet curable resin, and a vinyl ultraviolet curable resin [ [6] The optical filter according to [6].
  • the item wherein the substrate contains a dispersant having an acidic functional group and the content thereof is 5 to 300 parts by mass with respect to 100 parts by mass of the organic pigment (S).
  • the optical filter according to any one of [1] to [7].
  • optical filter according to any one of items [1] to [8], which is for a solid-state imaging device.
  • a solid-state imaging device comprising the optical filter according to any one of items [1] to [9].
  • a camera module comprising the optical filter according to any one of items [1] to [9].
  • an optical filter that has excellent near-infrared cut characteristics, little incident angle dependency, and excellent transmittance characteristics in the visible light wavelength region, color shading suppression effect, ghost suppression effect, and heat resistance. Can do.
  • FIGS. 1A and 1B are schematic views showing examples of preferable configurations of the optical filter of the present invention.
  • FIG. 2 is a spectral transmission spectrum of the optical filter obtained in Example 1. It is a schematic diagram for demonstrating the color shading evaluation of the camera image performed in the Example and the comparative example. It is a schematic diagram for demonstrating the ghost evaluation of the camera image performed in the Example and the comparative example.
  • the optical filter of the present invention has a base material that satisfies the requirement (a) described below, and has a dielectric multilayer film on at least one surface of the base material.
  • the thickness of the optical filter of the present invention is preferably thin considering the recent trend of thinning and weight reduction of solid-state imaging devices. Since the optical filter of the present invention includes the substrate, it can be thinned.
  • the thickness of the optical filter of the present invention is preferably 210 ⁇ m or less, more preferably 190 ⁇ m or less, further preferably 160 ⁇ m or less, particularly preferably 130 ⁇ m or less, and the lower limit is not particularly limited, but is preferably 20 ⁇ m or more.
  • the base material used in the present invention satisfies the following requirement (a).
  • (A) It has a layer containing an organic pigment (S) having an absorption maximum in a wavelength region of 900 nm to 1200 nm. Moreover, it is preferable that the base material further satisfies the following requirement (b).
  • (B) It has a layer containing the compound (A) having an absorption maximum in a wavelength region of 650 nm or more and 760 nm or less.
  • the component constituting the layer containing the organic pigment (S) is not particularly limited, and examples thereof include a transparent resin, a sol-gel material, a low-temperature-curing glass material, and the like.
  • a transparent resin is preferable from the viewpoint.
  • Organic pigment (S) is not particularly limited as long as it is an organic pigment having an absorption maximum in a wavelength region of 900 nm to 1200 nm.
  • the compound (S) having an absorption maximum in a wavelength region of 900 nm to 1200 nm. Can be obtained as a dispersion of the organic pigment (S) by dispersing it together with a dispersion medium and, if necessary, a dispersant and other additives by a known method.
  • the compound (S) is not particularly limited as long as the compound has an absorption maximum in a wavelength region of 900 nm or more and 1200 nm or less, but is preferably a diimonium compound, a metal dithiolate complex compound, a pyrrolopyrrole compound, or a cyanine compound. At least one compound selected from the group consisting of a compound, a croconium compound and a naphthalocyanine compound, more preferably at least one compound selected from the group consisting of a diimonium compound and a metal dithiolate complex compound, Particularly preferred are diimonium compounds represented by the following formula (I).
  • a compound (S) it is possible to impart good near infrared absorption characteristics and excellent visible light transmittance.
  • R 1 is independently a hydrogen atom, a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a carboxy group, a phosphoric acid group, -SR i group, -SO 2 R i groups, -OSO 2 R i group or a group represented by L a ⁇
  • R 2 represents any one of R h and R 2 independently represents a halogen atom, a sulfo group, a hydroxyl group, a cyano group, a nitro group, a carboxy group, a phosphate group, a —NR g R h group, a —SR i group, —SO 2 R i group, —OSO 2 R i group or any of the following L a to L h is represented, and R g and R h are each independently a hydrogen atom, —C (O) R i group or the following L a to L represents either e, R g
  • the substituent L is an aliphatic hydrocarbon group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms. At least one selected from the group consisting of a halogen-substituted alkyl group, an alicyclic hydrocarbon group having 3 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms and a heterocyclic group having 3 to 14 carbon atoms Yes, n represents an integer of 0 to 4, X represents an anion necessary for neutralizing the electric charge.
  • R 1 is preferably a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, cyclohexyl group, adamantyl group, trifluoromethyl group.
  • R 2 is preferably a chlorine atom, fluorine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, cyclohexyl group, phenyl group, hydroxyl group , Amino group, dimethylamino group, cyano group, nitro group, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, acetylamino group, propionylamino group, N-methylacetylamino group, trifluoromethanoylamino Group, pentafluoroethanoylamino group, tert-butanoylamino group, cyclohexylinoylamino group, n-butylsulfonyl group, methylthio group, ethylthio group, n-propylthio
  • X is an anion necessary for neutralizing electric charge.
  • X is a divalent anion
  • X is one
  • X is a monovalent anion
  • X is two. is there.
  • the two anions may be the same or different, but are preferably the same from the viewpoint of synthesis.
  • X will not be specifically limited if it is such an anion, As an example, the thing of following Table 1 can be mentioned.
  • X is (X-10), (X-16), (X-17), (X-21), (X-21) in Table 1 above from the viewpoint of heat resistance, light resistance and spectral properties of the diimonium compound.
  • X-22), (X-24) and (X-28) are particularly preferred.
  • Examples of the diimonium compound represented by the above formula (I) include those listed in Tables 2-1 to 2-4 below.
  • the compound (S) may be synthesized by a generally known method.
  • Japanese Patent No. 4168031 Japanese Patent No. 4225296, JP-T 2010-516823, JP-A No. 63-165392 It can be synthesized with reference to the method described in the publication.
  • the absorption maximum wavelength of the compound (S) is preferably 920 nm to 1195 nm, more preferably 950 nm to 1190 nm, and further preferably 980 nm to 1180 nm.
  • the absorption maximum wavelength of the compound (S) is in such a range, unnecessary near-infrared rays can be efficiently cut, and an excellent ghost suppression effect can be obtained.
  • the organic pigment (S) is preferably used by dispersing the compound (S) in a dispersion medium by a generally known method, for example, a method using a known disperser.
  • a dispersion medium having extremely high solubility with respect to the compound (S) is selected, the compound (S) is dissolved in the dispersion medium and becomes a dye. In this case, desired spectral characteristics cannot be obtained, and heat resistance and UV resistance are significantly reduced. Therefore, it is necessary to select a dispersion medium that has low solubility in the compound (S) and does not form a dye.
  • the dispersion medium dyes the compound (S) is determined by adding the dispersion medium to the compound (S) and dropping it into a glass plate so that the concentration of the compound (S) is 0.1% by mass. After drying, it can be confirmed by observing with a scanning electron microscope. When the compound (S) is present in the form of particles, it can be determined that it is pigmented, and when the particulate material is not confirmed, it can be determined that it is dyed.
  • the dispersion medium is not particularly limited as long as it does not dye the compound (S), but a solvent having a relatively high polarity is preferable from the viewpoint of safety in the dispersion process.
  • a solvent having a relatively high polarity is preferable from the viewpoint of safety in the dispersion process.
  • alcohols such as isopropanol and ethanol
  • Ketones such as methyl ethyl ketone and methyl isobutyl ketone
  • esters such as butyl acetate and ethyl acetate
  • ethers such as propylene glycol monomethyl ether.
  • the compound (S) is a diimonium compound
  • alcohols such as isopropanol and ethanol are particularly preferable from the viewpoint of storage stability of the dispersion.
  • a halogen solvent such as methylene chloride because the compound (S) is dyed.
  • Disperser examples of the disperser used when dispersing the compound (S) in a dispersion medium include a bead mill, a ball mill, a vibrating ball mill, a planetary ball mill, a sand mill, a colloid mill, a jet mill, and a roller mill.
  • the organic pigment (S) may be prepared by refining the primary particles of the compound (S) by so-called salt milling.
  • salt milling method for example, a method disclosed in Japanese Patent Laid-Open No. 8-179111 can be employed.
  • the compound (S) may be dispersed using a known dispersant.
  • the dispersant include a urethane-based dispersant, a polyethyleneimine-based dispersant, a polyoxyethylene alkyl ether-based dispersant, a polyoxyethylene alkylphenyl ether-based dispersant, a polyethylene glycol diester-based dispersant, and a sorbitan fatty acid ester-based dispersant.
  • Examples of commercially available products include (meth) acrylic dispersants such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN22102 (manufactured by BYK (BYK)), Disperbyk-161, Disperbyk.
  • Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 manufactured by BYK Corporation
  • Solsperse 76500 manufactured by Lubrizol Co., Ltd.
  • Solsperse 24000 Polyethyleneimine-based dispersants such as Lubrizol Co., Ltd.
  • polyester dispersants such as those manufactured by Ajinomoto Fine Techno Co., Ltd., BYK-LPN21324 (manufactured by BYK Corporation), Mariarim SC series, Esliem AD series, Esliem C2093I (above, NOF Corporation) Etc.
  • Examples of the (meth) acrylic dispersant include, for example, JP 2011-232735 A, JP 2011-237769 A, JP 2012-32767 A, International Publication 2011/129078, International Publication 2012. Copolymers disclosed in the / 001945 pamphlet and the like can also be used.
  • a dispersing agent can be used 1 type or in combination of 2 or more types.
  • a dispersant having an acidic functional group in terms of good dispersion stability and small chemical action on the compound (S).
  • the dispersant having an acidic functional group is not particularly limited as long as it is a dispersant having a carboxylic acid, a sulfonic acid, a phenolic hydroxyl group, or a salt thereof.
  • an ethylenically unsaturated monomer having an acidic functional group And other copolymerizable ethylenically unsaturated monomers.
  • Examples of commercially available products include the above-mentioned Mariarim SC series, DISPERBYK-103, DISPERBYK-110, DISPERBYK-118, and the like.
  • the content of the dispersant can be appropriately selected depending on the type of the dispersant, but is preferably 5 to 300 parts by weight, more preferably 10 to 200 parts by weight, and more preferably 100 parts by weight of the organic pigment (S).
  • the amount is preferably 20 to 150 parts by mass. It is preferable for the content of the dispersant to be in the above range because the dispersion stability of the dispersion is good and the heat resistance, water resistance and adhesion of the substrate and optical filter are excellent.
  • Centrifugation treatment can remove coarse organic pigment particles that are insufficiently dispersed, thereby reducing the average particle size of the organic pigment, and as a result, haze of the optical filter can be reduced.
  • time of sputum centrifugation processing For example, it is 1 minute or more and 60 minutes or less.
  • centrifugal acceleration of the centrifuge at the time of performing sputum centrifuge For example, it can be set as 10 G or more and 50,000 G or less.
  • Average particle diameter of organic pigment (S) is preferably 200 nm or less, more preferably 5 to 190 nm, still more preferably 10 to 180 nm, and particularly preferably 15 to 150 nm.
  • the average particle diameter of the organic pigment (S) in the present invention is a value obtained by the measurement method described in Examples described later.
  • an optical filter excellent in heat resistance can be obtained while maintaining the haze value at an extremely low level.
  • the content of the entire organic pigment (S) is, for example, a base material made of a transparent resin substrate containing the organic pigment (S) or an organic pigment (S).
  • a base material in which a resin layer such as an overcoat layer made of a curable resin or the like is used on a transparent resin substrate containing S
  • it is preferably 0.01 with respect to 100 parts by mass of the transparent resin.
  • a glass support or a resin support as a base is used as the substrate.
  • a transparent resin containing the organic pigment (S) Preferably it is 0.1 with respect to 100 mass parts of resin which forms a layer. 5.0 parts by weight, more preferably 0.2 to 4.0 mass parts, and particularly preferably 0.3 to 3.0 parts by.
  • an optical filter having both good near infrared absorption characteristics and high visible light transmittance can be obtained.
  • the component constituting the layer containing the compound (A) is not particularly limited, and examples thereof include a transparent resin, a sol-gel material, a low-temperature-curing glass material, and the like.
  • a transparent resin is preferable from the viewpoint of compatibility with A).
  • the compound (A) is not particularly limited as long as it is a compound having an absorption maximum in a wavelength region of 650 nm or more and 760 nm or less, but is preferably a solvent-soluble dye compound, and is a squarylium compound, a phthalocyanine compound, and a cyanine compound. It is more preferable that it is at least one selected from the group consisting of compounds, it is more preferable that a squarylium compound is included, and it is particularly preferable that there are two or more compounds including a squarylium compound.
  • the compound (A) is two or more types including a squarylium compound, two or more types of squarylium compounds having different structures may be used, or a combination of a squarylium compound and another compound (A) may be used.
  • the other compound (A) a phthalocyanine compound and a cyanine compound are particularly preferable.
  • the squarylium-based compound has excellent visible light permeability, steep absorption characteristics, and a high molar extinction coefficient, but may generate fluorescence that causes scattered light during light absorption. In such a case, an optical filter with less scattered light and better camera image quality can be obtained by using a combination of the squarylium compound and the other compound (A).
  • the absorption maximum wavelength of the compound (A) is preferably 660 nm or more and 755 nm or less, more preferably 670 nm or more and 750 nm or less, and further preferably 680 nm or more and 745 nm or less.
  • the difference between the absorption maximum wavelengths of the compound (A) to be applied having the shortest absorption maximum wavelength and the longest absorption maximum wavelength is preferably 10 to The thickness is 60 nm, more preferably 15 to 55 nm, still more preferably 20 to 50 nm. It is preferable that the difference in absorption maximum wavelength is in the above-mentioned range because scattered light due to fluorescence can be sufficiently reduced and a wide absorption band near 700 nm and an excellent visible light transmittance can be compatible.
  • the total content of the compound (A) is, for example, a base material made of a transparent resin substrate containing the organic pigment (S) and the compound (A) or a transparent resin containing the compound (A) as the base material.
  • a base material in which a resin layer such as an overcoat layer made of a curable resin containing an organic pigment (S) is laminated on a substrate, it is preferably 0.04 with respect to 100 parts by mass of the transparent resin. 2.0 parts by mass, more preferably 0.06 to 1.5 parts by mass, and still more preferably 0.08 to 1.0 parts by mass.
  • a glass support or a resin support as a base is used as the substrate.
  • the compound (A) 100 When using a substrate in which a transparent resin layer such as an overcoat layer made of a curable resin containing the organic pigment (S) and the compound (A) is laminated on a support such as a body, the compound (A) 100 forming a transparent resin layer containing Relative to the amount unit, preferably 0.4 to 5.0 parts by mass, more preferably in a range of 0.6 to 4.0 mass parts, more preferably 0.8 to 3.5 mass parts.
  • the substrate may be a single layer or a multilayer as long as it has a layer containing an organic pigment (S). Moreover, the compound (A) may be contained in the same layer as the organic pigment (S) or in a different layer.
  • the layer containing the organic pigment (S) and the layer containing the compound (A) are the same, for example, a base material made of a transparent resin substrate containing the organic pigment (S) and the compound (A), an organic pigment (S ) And a transparent resin substrate containing the compound (A) on a substrate such as an overcoat layer made of a curable resin or the like, a support such as a glass support or a base resin support And a substrate on which a transparent resin layer such as an overcoat layer made of a curable resin containing the organic pigment (S) and the compound (A) is laminated.
  • an overcoat made of a curable resin containing the compound (A) on a transparent resin substrate containing the organic pigment (S) A base material on which a resin layer such as a layer is laminated, or a base material on which a resin layer such as an overcoat layer made of a curable resin containing an organic pigment (S) is laminated on a transparent resin substrate containing the compound (A)
  • An overcoat layer made of a curable resin containing an organic pigment (S) on a support such as a glass support or a base resin support, and an overcoat layer made of a curable resin containing a compound (A) Can be mentioned.
  • the organic pigment (S) The average particle size is more preferably 150 nm or less, and particularly preferably 100 nm or less.
  • the average transmittance of the substrate in the wavelength region of 430 to 580 nm is preferably 75% or more, more preferably 78% or more, and particularly preferably 80% or more.
  • a substrate having such transmission characteristics is used, high light transmission characteristics can be achieved in the visible light region, and a highly sensitive camera function can be achieved.
  • the thickness of the substrate can be appropriately selected according to the desired application and is not particularly limited, but is preferably 10 to 200 ⁇ m, more preferably 20 to 180 ⁇ m, and further preferably 25 to 150 ⁇ m.
  • an optical filter using the substrate can be reduced in thickness and weight, and can be suitably used for various applications such as a solid-state imaging device.
  • a base material made of the transparent resin substrate is used in a lens unit such as a camera module, it is preferable because the lens unit can be reduced in height and weight.
  • the transparent resin used for the transparent resin layer, the transparent resin substrate and the resin support constituting the substrate is not particularly limited as long as it does not impair the effects of the present invention.
  • thermal stability and film Glass transition temperature (Tg) is preferably 110 to 380 ° C., in order to obtain a film capable of forming a dielectric multilayer film by high temperature vapor deposition performed at a vapor deposition temperature of 100 ° C. or higher while ensuring moldability to
  • a resin having a temperature of 110 to 370 ° C., more preferably 120 to 360 ° C. is used.
  • 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. %, More 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.
  • transparent resins examples include cyclic polyolefin resins, aromatic polyether resins, polyimide resins, fluorene polycarbonate resins, fluorene polyester resins, polycarbonate resins, polyamide (aramid) resins, polyarylate resins, and polysulfones.
  • ester-based curable resins examples include ester-based curable resins, silsesquioxane-based ultraviolet curable resins, acrylic-based ultraviolet curable resins, and vinyl-based ultraviolet curable resins.
  • Transparent resins may be used alone or in combination of two or more.
  • the cyclic polyolefin-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 Represents an integer of ⁇ 4.
  • 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 represent 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 an integer of 0-4.
  • 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 represents an integer of 0 to 4.
  • R 1 ⁇ R 4 and a ⁇ d independently has the same meaning as R 1 ⁇ R 4 and a ⁇ d of the formula (1)
  • Y represents a single bond
  • R 7 and R 8 each independently represent a halogen atom, a monovalent organic group having 1 to 12 carbon atoms or a nitro group
  • g and h each independently represents 0 to 4 Represents an integer
  • m represents 0 or 1.
  • R 7 is not a cyano group.
  • 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 —, — CO—, —CONH—, —COO— or a divalent organic group having 1 to 12 carbon atoms
  • e and f each independently represents 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 formula (2), and R 5 , R 6 , Z, n, e and f are each independently synonymous with 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 high molecular compound containing an imide bond in a repeating unit.
  • the method described in JP-A-2006-199945 and JP-A-2008-163107 is used. Can be synthesized.
  • 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 as long as it is a 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. Can do.
  • the fluorinated aromatic polymer resin is not particularly limited, but is selected from the group consisting of an aromatic ring having at least one fluorine atom, an ether bond, a ketone bond, a sulfone bond, an amide bond, an imide bond, and an ester bond.
  • the polymer preferably contains a repeating unit containing at least one bond, and can be synthesized, for example, by the method described in JP-A-2008-181121.
  • the acrylic ultraviolet curable resin is not particularly limited, but is synthesized from a resin composition containing a compound having one or more acrylic or methacrylic groups in the molecule and a compound that decomposes by ultraviolet rays to generate active radicals. Can be mentioned.
  • the acrylic ultraviolet curable resin is a base material in which a transparent resin layer containing a compound (A) and a curable resin is laminated on a glass support or a resin support as a base, or a compound ( When using a base material in which a resin layer such as an overcoat layer made of a curable resin or the like is used on a transparent resin substrate containing A), it can be particularly preferably used as the curable resin.
  • Epoxy resin Although it does not specifically limit as an epoxy-type resin, It can divide roughly into an ultraviolet curing type and a thermosetting type.
  • the ultraviolet curable epoxy resin for example, synthesized from a composition containing a compound having one or more epoxy groups in the molecule and a compound that generates an acid by ultraviolet rays (hereinafter also referred to as “photo acid generator”).
  • thermosetting epoxy resins include those synthesized from a composition containing one or more epoxy groups in the molecule and an acid anhydride. Can do.
  • the epoxy ultraviolet curable resin contains, as the base material, a base material obtained by laminating a transparent resin layer containing the compound (A) on a glass support or a base resin support, and the compound (A). In the case of using a base material in which a resin layer such as an overcoat layer made of a curable resin is laminated on a transparent resin substrate to be used, it can be particularly suitably used as the curable resin.
  • cyclic polyolefin resins examples include Arton manufactured by JSR Corporation, ZEONOR manufactured by Nippon Zeon Co., Ltd., APEL manufactured by Mitsui Chemicals, Inc., and TOPAS manufactured by Polyplastics Corporation.
  • polyethersulfone resins examples include Sumika Excel PES manufactured by Sumitomo Chemical Co., Ltd.
  • polyimide resins examples include Neoprim L manufactured by Mitsubishi Gas Chemical Co., Ltd.
  • 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.
  • Examples of commercially available acrylic resins include NIPPON CATALYST ACRYVIEWER.
  • Examples of commercially available silsesquioxane-based ultraviolet curable resins include Silplus manufactured by Nippon Steel Chemical Co., Ltd.
  • the base material may further contain other pigment (X) not corresponding to the organic pigment (S) and the compound (A).
  • the other dye (X) is not particularly limited as long as the absorption maximum wavelength is in the region of wavelength less than 650 nm or more than 760 nm and less than 900 nm, but the dye having the absorption maximum wavelength in the region of more than 760 nm and less than 900 nm is preferable.
  • examples of such dyes include squarylium compounds, phthalocyanine compounds, cyanine compounds, naphthalocyanine compounds, croconium compounds, octaphyrin compounds, diimonium compounds, pyrrolopyrrole compounds, and boron dipyrromethene (BODIPY). And at least one compound selected from the group consisting of a compound, a perylene compound, and a metal dithiolate compound.
  • the content of the other dye (X) is, for example, when a base material made of a transparent resin substrate containing the other dye (X) is used as the base material, with respect to 100 parts by mass of the transparent resin.
  • the amount is preferably 0.005 to 1.0 part by mass, more preferably 0.01 to 0.9 part by mass, particularly preferably 0.02 to 0.8 part by mass.
  • a transparent material containing other dye (X) is used.
  • resin forming the resin layer Preferably 0.05 to 4.0 mass parts, more preferably 0.1 to 3.0 mass parts, and particularly preferably 0.2 to 2.0 parts by mass.
  • the base material may further contain an antioxidant, a near-ultraviolet absorber, a fluorescence quencher, and the like as other components as long as the effects of the present invention are not impaired. These other components may be used alone or in combination of two or more.
  • Examples of the near ultraviolet absorber include azomethine compounds, indole compounds, benzotriazole compounds, triazine compounds, and the like.
  • antioxidants examples include 2,6-di-t-butyl-4-methylphenol, 2,2′-dioxy-3,3′-di-t-butyl-5,5′-dimethyldiphenylmethane, tetrakis [Methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, tris (2,4-di-t-butylphenyl) phosphite and the like.
  • these other components may be mixed with a resin or the like when producing a substrate, or may be added when a resin is synthesized.
  • 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 with respect to 100 parts by weight of the resin. Part.
  • the base material is a base material including a transparent resin substrate containing an organic pigment (S)
  • the transparent resin substrate can be formed by, for example, melt molding or cast molding, and further if necessary.
  • a substrate on which an overcoat layer is laminated can be produced by coating a coating agent such as an antireflection agent, a hard coat agent and / or an antistatic agent.
  • the substrate is made of a curable resin containing an organic pigment (S) on a support such as a glass support or a base resin support or a transparent resin substrate containing no organic pigment (S).
  • a transparent resin layer such as an overcoat layer is laminated
  • a resin solution containing the compound (A) on the support or the transparent resin substrate for example, preferably by melt molding or cast molding a resin solution containing the compound (A) on the support or the transparent resin substrate.
  • a method such as spin coating, slit coating, and ink jet, and then the solvent is dried and removed, and if necessary, light irradiation or heating is performed to form an organic pigment on the support or the transparent resin substrate.
  • a substrate on which a transparent resin layer containing (S) is formed can be produced.
  • melt molding a method of melt molding pellets obtained by melt-kneading a resin, an organic pigment (S) and other components as necessary; a resin and an organic pigment (S) And a method of melt-molding a resin composition containing other components as necessary; or removing the solvent from the resin composition containing the organic pigment (S), the resin, the solvent and, if necessary, the other components
  • the method of melt-molding the obtained pellet is mentioned.
  • the melt molding method include injection molding, melt extrusion molding, and blow molding.
  • ⁇ Cast molding As the cast molding, a method of removing a solvent by casting a resin composition containing an organic pigment (S), a resin, a solvent and, if necessary, other components on a suitable support; or an organic pigment (S ), A photocurable resin and / or a thermosetting resin, and if necessary, a curable composition containing other components is cast on a suitable support to remove the solvent, It can also be produced by a method of curing by an appropriate method such as heating.
  • the base material is a base material made of a transparent resin substrate containing the organic pigment (S)
  • the base material can be obtained by peeling the coating film from the support after cast molding.
  • the base material is a curable resin containing an organic pigment (S) on a support such as a glass support or a base resin support or on a transparent resin substrate containing no organic pigment (S).
  • the base material can be obtained by not peeling the coating film after cast molding.
  • a near-infrared absorbing glass plate for example, a phosphate system containing a copper component such as “BS-11” manufactured by Matsunami Glass Industrial Co., Ltd. or “NF-50T” manufactured by AGC Sakai Techno Glass Co., Ltd.) Glass plate
  • transparent glass plate for example, non-alkali glass plate such as “OA-10G” manufactured by Nippon Electric Glass Co., Ltd., “AN100” manufactured by Asahi Glass Co., Ltd.
  • steel belt for example, steel drum, and transparent resin (for example, polyester film) , Cyclic olefin resin film) support.
  • the amount of residual solvent in the transparent resin layer (transparent resin substrate) obtained by the above method should be as small as possible.
  • the amount of the residual solvent is preferably 3 parts by mass or less, more preferably 1 part by mass or less, further preferably 0.5 parts by mass with respect to 100 parts by mass of the transparent resin layer (transparent resin substrate). It is as follows. When the amount of residual solvent is in the above range, a transparent resin layer (transparent resin substrate) that can easily exhibit a desired function is obtained, which hardly causes deformation of the base material or changes in optical properties.
  • the optical filter of the present invention has a dielectric multilayer film on at least one surface of the substrate.
  • the dielectric multilayer film in the present invention is a film having the ability to reflect near-infrared light or a film having an antireflection effect in the visible light region. Infrared cut characteristics can be achieved.
  • the dielectric multilayer film may be provided on one side of the substrate or on both sides.
  • the optical filter When it is provided on one side, it is possible to obtain an optical filter that is excellent in production cost and manufacturability and has high strength and is less likely to warp or twist when provided on both sides.
  • the optical filter When the optical filter is applied to a solid-state imaging device, it is preferable that the optical filter is less warped or twisted. Therefore, it is preferable to provide a dielectric multilayer film on both surfaces of the resin substrate.
  • the dielectric multilayer film preferably has reflection characteristics over the entire wavelength range of 700 to 1100 nm, more preferably 700 to 1150 nm, and even more preferably 700 to 1200 nm.
  • the first optical layer mainly having a reflection characteristic in the vicinity of a wavelength of 700 to 950 nm when measured from an angle of 5 ° with respect to the vertical direction of the optical filter is used.
  • a configuration (see FIG. 1 (a)) having a second optical layer on one side of the material and having a reflection characteristic mainly in the vicinity of 900 nm to 1150 nm on the other side of the substrate, and the vertical direction of the optical filter
  • the form (refer FIG.1 (b)) which has on the other surface of a base material etc. are mentioned.
  • Examples of the dielectric multilayer film include those in which a high refractive index material layer and a low refractive index material layer are alternately laminated.
  • a material constituting the high refractive index material layer 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.
  • Such materials include titanium oxide, zirconium oxide, tantalum pentoxide, niobium pentoxide, lanthanum oxide, yttrium oxide, zinc oxide, zinc sulfide, or indium oxide as the main components, and titanium oxide, tin oxide, and / or Alternatively, a material containing a small amount of cerium oxide or the like (eg, 0 to 10 parts by mass with respect to 100 parts by mass of the main component) can be used.
  • 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 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 thickness obtained by multiplying the refractive index (n) by the thickness (d) (n ⁇ d) by ⁇ / 4 the high refractive index material layer, and the low refractive index.
  • the thicknesses of the respective layers of the refractive index material layer are 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 stacked high refractive index material layers and low refractive index material layers in the dielectric multilayer film is preferably 16 to 70 layers, more preferably 20 to 60 layers, as a whole, 24 Particularly preferred is ⁇ 50 layers. If the thickness of each layer, the thickness of the dielectric multilayer film as a whole of the optical filter, and the total number of layers are within the above ranges, a sufficient manufacturing margin can be secured, and the warpage of the optical filter and cracks in the dielectric multilayer film can be reduced. can do.
  • the material type constituting the high refractive index material layer and the low refractive index material layer, the high refractive index material layer, and the low refractive index are adjusted in accordance with the absorption characteristics of the near-infrared absorber such as the compound (A) or the organic pigment (S).
  • the near-infrared absorber such as the compound (A) or the organic pigment (S).
  • Appropriate selection of the thickness of each refractive index material layer, the order of stacking, and the number of stacks ensure sufficient light-cutting characteristics in the near-infrared wavelength region while ensuring sufficient transmittance in the visible light region.
  • the reflectance when near-infrared rays inject from an oblique direction can be reduced.
  • optical thin film design software for example, Essential Macleod, Thin Film Center
  • both the antireflection effect in the visible light region and the light cut effect in the near infrared region are compatible.
  • the target transmittance at a wavelength of 400 to 700 nm is set to 100%
  • the target Tolerance value is set to 1
  • the target transmittance at a wavelength of 705 to 950 nm is set to 0%.
  • Parameter setting method such as setting Target Tolerance value to 0.5 can be mentioned.
  • the optical filter of the present invention is within the range not impairing the effects of the present invention, between the base material and the dielectric multilayer film, the surface opposite to the surface on which the dielectric multilayer film is provided, or the dielectric multilayer film.
  • an anti-reflection film On the opposite side of the surface of the film where the substrate is provided, an anti-reflection film, a hard layer is used for the purpose of improving the surface hardness of the substrate or the dielectric multilayer film, improving the chemical resistance, antistatic and scratching.
  • Functional films such as a coating film and an antistatic film can be provided as appropriate.
  • the optical filter of the present invention may include one layer made of the functional film or two or more layers.
  • the optical filter of the present invention may include two or more similar layers or two or more different layers.
  • the method for laminating the functional film is not particularly limited, but a coating agent containing an antireflection agent, a hard coating agent and / or an antistatic agent, etc. is melt-molded or cast in the same manner as described above on a base material or a dielectric multilayer film. Examples of the method include molding.
  • the coating agent can be produced by applying the coating agent on a base material or a dielectric multilayer film with a bar coater or the like and then curing it by ultraviolet irradiation or the like.
  • the coating agent examples include curable compositions containing ultraviolet (UV) / electron beam (EB) curable resins and thermosetting resins.
  • UV ultraviolet
  • EB electron beam
  • Specific examples of the curable resin contained in the curable composition include vinyl compounds, urethane, urethane acrylate, acrylate, epoxy, and epoxy acrylate resins.
  • the curable composition may contain a polymerization initiator.
  • a polymerization initiator a known photopolymerization initiator or a thermal polymerization initiator can be used, and a photopolymerization initiator and a thermal polymerization initiator may be used in combination.
  • a polymerization initiator may be used individually by 1 type, and may use 2 or more types together.
  • the mixing ratio of the polymerization initiator is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 10 parts by mass, when the total amount of the curable composition is 100 parts by mass. More preferably, it is 1 to 5 parts by mass.
  • the blending ratio of the polymerization initiator is within the above range, it is possible to obtain a functional film such as an antireflective film, a hard coat film or an antistatic film having excellent curing characteristics and handleability of the curable composition and having a desired hardness. it can.
  • an organic solvent may be added as a solvent to the curable composition, and known organic solvents can be used.
  • the organic solvent include alcohols such as methanol, ethanol, isopropanol, butanol and octanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethyl acetate, butyl acetate, ethyl lactate, ⁇ -butyrolactone, propylene Esters such as glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; Ethers such as ethylene glycol monomethyl ether and diethylene glycol monobutyl ether; Aromatic hydrocarbons such as benzene, toluene and xylene; Dimethylformamide, dimethylacetamide, N- Examples include amides such as methylpyrrolidone.
  • solvents may be used alone or in combination of two or more.
  • the thickness of the functional film is preferably 0.1 to 20 ⁇ m, more preferably 0.5 to 10 ⁇ m, and particularly preferably 0.7 to 5 ⁇ m.
  • the corona is applied to the surface of the base material, the functional film or the dielectric multilayer film.
  • Surface treatment such as treatment or plasma treatment may be performed.
  • 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.
  • digital still cameras, smartphone cameras, mobile phone cameras, digital video cameras, wearable device cameras, PC cameras, surveillance cameras, automotive cameras, TVs, car navigation systems, personal digital assistants, video game machines, and portable game machines It is useful for fingerprint authentication system, digital music player, etc. Furthermore, 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.
  • a digital still camera a camera for a smartphone, a camera for a mobile phone, a camera for a wearable device, a digital camera It can be used for applications such as video cameras.
  • the camera module of the present invention includes the optical filter of the present invention.
  • Part means “part by mass” unless otherwise specified.
  • 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.
  • Tg Glass transition temperature
  • DSC6200 differential scanning calorimeter
  • the average particle diameter of the organic pigment was measured by the following method.
  • the prepared dispersion liquid of the organic pigment is diluted with a solvent having the same composition as the dispersion medium until the pigment concentration becomes 0.5% by mass, dropped on a glass plate and dried, and then scanned with an electron microscope (SEM) ( Observation was performed with Hitachi High-Technologies Corporation “S4800”. SEM images were taken from a plurality of fields of view, and the particle size of 100 arbitrarily selected particles was measured on a scale and converted into a magnification to calculate an average particle size. In addition, extremely large or small particles were excluded, and when the particle shape was not spherical, the longest diameter (major axis) observed was taken as the particle diameter.
  • ⁇ Spectral transmittance> The transmittance in each wavelength region of the substrate and the optical filter was measured using a spectrophotometer (U-4100) manufactured by Hitachi High-Technologies Corporation. The transmittance is measured using the spectrophotometer under the condition that light is incident on the substrate and the filter perpendicularly.
  • ⁇ Haze> The haze of the substrate and the optical filter was measured using a haze meter (Haze Guard II) manufactured by Toyo Seiki Seisakusho Co., Ltd. Measurements were taken at three different locations and the average value was used.
  • ⁇ Camera image color shading evaluation> The color shading evaluation when the optical filter was incorporated in the camera module was performed by the following method.
  • a camera module is created in the same manner as in Japanese Patent Application Laid-Open No. 2016-110067, and a white plate having a size of 300 mm ⁇ 400 mm is formed using the created camera module as a D65 light source (standard light source device “Macbeth Judge II” manufactured by X-Rite) Images were taken below, and the difference in color between the center and edge of the white plate in the camera image was evaluated according to the following criteria.
  • the positional relationship between the white plate 112 and the camera module was adjusted so that the white plate 112 occupied 90% or more of the area in the camera image 111 when shooting.
  • Ghost evaluation when the optical filter was incorporated in the camera module was performed by the following method.
  • a camera module is created in the same manner as in Japanese Patent Application Laid-Open No. 2016-110067, and the camera module is used to take a picture under a halogen lamp light source (“Luminer Ace LA-150TX” manufactured by Hayashi Watch Industry Co., Ltd.) in a dark room.
  • a halogen lamp light source (“Luminer Ace LA-150TX” manufactured by Hayashi Watch Industry Co., Ltd.) in a dark room.
  • the degree of ghost generation around the light source in the image was evaluated according to the following criteria.
  • DCM dodec-3-ene
  • the temperature was raised to ° C. After confirming that 3-hydroxy-1-adamantyl acrylate was dissolved and the solution was clarified, 27.047 g of 3-hydroxy-1-adamantyl acrylate was additionally charged, and the reaction was continued at 70 ° C. The reaction was completed after confirming that the absorption spectrum of the isocyanate group (2280 cm ⁇ 1 ) almost disappeared in the infrared absorption spectrum.
  • the reaction mixture was purified by silica gel column chromatography using ethyl acetate / hexane as an eluent, and then diluted with isopropyl alcohol to obtain urethane acrylate compound (I) (50% by mass solution).
  • ⁇ Preparation Example 2> In a 0.25 L plastic container, 5 g of the compound (s-15) shown in Table 2-4 above, 95 g of methyl isobutyl ketone (MIBK) as a dispersion medium, 0.05 mm diameter zirconia beads (“YTZ-0. 05 ”) 175 g was charged and dispersed for 1 hr with a paint shaker. Thereafter, the mixture was cooled to room temperature, and zirconia beads were filtered off with a metal mesh to obtain an organic pigment dispersion (S-2).
  • MIBK methyl isobutyl ketone
  • ⁇ Preparation Example 3> In a 0.25 L plastic container, 5 g of the compound (s-4) shown in Table 2-4 (maximum absorption wavelength 1100 nm in dichloromethane), 95 g of methyl isobutyl ketone (MIBK) as a dispersion medium, zirconia having a diameter of 0.05 mm 175 g of beads (“YTZ-0.05” manufactured by Nikkato Co., Ltd.) was added and dispersed for 1 hr using a paint shaker. Thereafter, the mixture was cooled to room temperature, and zirconia beads were filtered off with a metal mesh to obtain an organic pigment dispersion (S-3).
  • MIBK methyl isobutyl ketone
  • ⁇ Preparation Example 4> In a 0.25 L plastic container, 5 g of the compound (s-6) shown in Table 2-4 (maximum absorption wavelength 1093 nm in dichloromethane), 95 g of methyl isobutyl ketone (MIBK) as a dispersion medium, zirconia having a diameter of 0.05 mm 175 g of beads (“YTZ-0.05” manufactured by Nikkato Co., Ltd.) was added and dispersed for 1 hr using a paint shaker. Thereafter, the mixture was cooled to room temperature, and zirconia beads were filtered off with a metal mesh to obtain an organic pigment dispersion (S-4).
  • MIBK methyl isobutyl ketone
  • Preparation Example 5 The organic pigment dispersion (S-1) obtained in Preparation Example 1 was centrifuged at a centrifugal acceleration of 36000 G for 10 minutes in a centrifuge (“cooled centrifuge CR-22N” manufactured by himac), and the dispersion after the treatment The liquid was filtered through a polypropylene filter (pore size: 3 ⁇ m) to obtain an organic pigment dispersion (S-5).
  • Example 1 an optical filter having a substrate formed by forming a transparent resin layer containing an organic pigment (S) on both surfaces of a transparent resin substrate containing a compound (A) was prepared according to the following procedure and conditions.
  • i-Pr represents an isopropyl group.
  • a resin composition (1) having the following composition was applied to one side of the obtained transparent resin substrate with a bar coater and heated in an oven at 70 ° C. for 3 minutes to volatilize and remove the solvent. At this time, the coating conditions of the bar coater were adjusted so that the thickness after drying was 3 ⁇ m. Next, it exposed using the conveyor type exposure machine (exposure amount 500mJ / cm ⁇ 2 >, 200mW), the resin composition (1) was hardened, and the transparent resin layer was formed on the substrate made from transparent resin. Similarly, a transparent resin layer made of the resin composition (1) is formed on the other surface of the transparent resin substrate, and the organic pigment (S) is transparent on both surfaces of the transparent resin substrate containing the compound (A). A substrate having a resin layer was obtained.
  • Resin composition (1) 100 g of tricyclodecane dimethanol acrylate, 3 g of 1-hydroxycyclohexyl phenyl ketone, 50 g of pigment dispersion (S-1) obtained in Preparation Example 1 (2.5 g in terms of organic pigment (S)) ), 117 g of isopropyl alcohol.
  • a dielectric multilayer film (I) is formed as a first optical layer on one side of the obtained base material, and a dielectric multilayer film (II) is formed as a second optical layer on the other side of the base material.
  • an optical filter having a thickness of about 0.105 mm was obtained.
  • the dielectric multilayer film (I) is formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers at a deposition temperature of 100 ° C. (26 layers in total).
  • the dielectric multilayer film (II) is formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers at a deposition temperature of 100 ° C. (20 layers in total).
  • the silica layer and the titania layer are in order of the titania layer, the silica layer, the titania layer,..., The silica layer, the titania layer, and the silica layer from the substrate side.
  • the outermost layer of the optical filter was a silica layer.
  • the dielectric multilayer films (I) and (II) were designed as follows. Regarding the thickness and the number of layers of each layer, the wavelength-dependent characteristics of the base material refractive index and the applied organic pigment (S) and the anti-reflection effect in the visible light region and the selective transmission / reflection performance in the near-infrared region can be achieved. Optimization was performed using optical thin film design software (Essential Macleod, manufactured by Thin Film Center) in accordance with the absorption characteristics of the compound (A). When performing optimization, in this example, the input parameters (Target values) to the software are as shown in Table 3 below.
  • the dielectric multilayer film (I) is formed by alternately stacking a silica layer having a film thickness of 31 to 157 nm and a titania layer having a film thickness of 10 to 95 nm.
  • the dielectric multi-layer film (II) is a multi-layer vapor-deposited film having 20 layers, in which a silica layer having a thickness of 37 to 194 nm and a titania layer having a thickness of 12 to 114 nm are alternately stacked. It was.
  • An example of the optimized film configuration is shown in Table 4 below.
  • the spectral transmittance and haze measured from the vertical direction of the obtained optical filter were measured to evaluate the optical characteristics in each wavelength region and the heat resistance described above. The results are shown in FIG.
  • Example 2 An optical filter was obtained and evaluated in the same manner as in Example 1 except that the resin composition (2) shown below was used instead of the resin composition (1). The results are shown in Table 5.
  • Resin composition (2) 50 g of urethane acrylate compound (1) obtained in Synthesis Example 2 (converted to solid content), 50 g of tricyclodecane dimethanol acrylate, 3 g of 1-hydroxycyclohexyl phenyl ketone, obtained in Preparation Example 1 50 g of pigment dispersion (S-1) (2.5 g in terms of organic pigment (S)), 117 g of isopropyl alcohol.
  • Example 3 An optical filter was obtained in the same manner as in Example 1 except that the resin composition (3) shown below was used instead of the resin composition (1), and the same evaluation was performed. The results are shown in Table 5.
  • Resin composition (3) 50 g of urethane acrylate compound (1) obtained in Synthesis Example 2 (in terms of solid content), 30 g of 3-hydroxy-1-adamantyl acrylate, 20 g of tricyclodecane dimethanol acrylate, 1-hydroxycyclohexylphenyl 3 g of ketone, 50 g of pigment dispersion (S-1) obtained in Preparation Example 1 (2.5 g in terms of organic pigment (S)), 117 g of isopropyl alcohol.
  • Example 4 An optical filter was obtained and evaluated in the same manner as in Example 1 except that the resin composition (4) shown below was used instead of the resin composition (1). The results are shown in Table 5.
  • Resin composition (4) 100 g of tricyclodecane dimethanol acrylate, 3 g of 1-hydroxycyclohexyl phenyl ketone, 50 g of the pigment dispersion (S-2) obtained in Preparation Example 2 (2.5 g in terms of organic pigment (S)) ), 117 g of methyl isobutyl ketone.
  • Example 5 instead of the transparent resin substrate, a glass substrate (a transparent glass substrate “OA-10G (thickness 150 ⁇ m) cut to 60 mm length and 60 mm width)” (manufactured by Nippon Electric Glass Co., Ltd.) was used. Resin composition (1) An optical filter was obtained and evaluated in the same manner as in Example 1 except that the resin composition (5) shown below was used instead of 1. The results are shown in Table 5.
  • Resin composition (5) 100 g of tricyclodecane dimethanol acrylate, 3 g of 1-hydroxycyclohexyl phenyl ketone, 50 g of the pigment dispersion (S-2) obtained in Preparation Example 2 (2.5 g in terms of organic pigment (S)) ), Compound (a-1) 0.5 g, compound (a-2) 0.4 g, methyl isobutyl ketone 112 g.
  • Example 6 Optical in the same manner as in Example 5 except that a transparent resin film (Zeonor film ZF16 (thickness 100 ⁇ m)) (manufactured by Nippon Zeon Co., Ltd.) cut to a size of 60 mm in length and 60 mm in width was used instead of the glass substrate. A filter was obtained and evaluated, and the results are shown in Table 5.
  • a transparent resin film Zeonor film ZF16 (thickness 100 ⁇ m)
  • Example 7 An optical filter was obtained and evaluated in the same manner as in Example 3 except that the resin composition (6) shown below was used instead of the resin composition (1). The results are shown in Table 5.
  • Resin composition (6) 50 g of urethane acrylate compound (1) obtained in Synthesis Example 2 (in terms of solid content), 30 g of 3-hydroxy-1-adamantyl acrylate, 20 g of tricyclodecane dimethanol acrylate, 1-hydroxycyclohexylphenyl 3 g of ketone, 56 g of the pigment dispersion (S-3) obtained in Preparation Example 3 (2.8 g in terms of organic pigment (S)), and 117 g of isopropyl alcohol.
  • Example 8 An optical filter was obtained and evaluated in the same manner as in Example 3 except that the resin composition (7) shown below was used instead of the resin composition (1). The results are shown in Table 5.
  • Resin composition (7) 50 g of urethane acrylate compound (1) obtained in Synthesis Example 2 (converted to solid content), 30 g of 3-hydroxy-1-adamantyl acrylate, 20 g of tricyclodecane dimethanol acrylate, 1-hydroxycyclohexylphenyl 3 g of ketone, 52 g of pigment dispersion (S-4) obtained in Preparation Example 4 (2.6 g in terms of organic pigment (S)), and 117 g of isopropyl alcohol.
  • Example 9 An optical filter was obtained and evaluated in the same manner as in Example 3 except that the resin composition (8) shown below was used instead of the resin composition (1). The results are shown in Table 5.
  • Resin composition (8) 50 g of urethane acrylate compound (1) obtained in Synthesis Example 2 (converted to solid content), 30 g of 3-hydroxy-1-adamantyl acrylate, 20 g of tricyclodecane dimethanol acrylate, 1-hydroxycyclohexylphenyl 3 g of ketone, 50 g of the pigment dispersion (S-5) obtained in Preparation Example 5 (2.5 g in terms of organic pigment (S)), and 117 g of isopropyl alcohol.
  • the peeled coating film was further dried at 100 ° C. under reduced pressure for 8 hours to obtain a transparent resin substrate having a thickness of 0.1 mm, a length of 60 mm, and a width of 60 mm.
  • Resin composition (6) 100 g of tricyclodecane dimethanol acrylate, 3 g of 1-hydroxycyclohexyl phenyl ketone, 154.5 g of methyl ethyl ketone.
  • Resin composition (7) Tricyclodecane dimethanol acrylate 100 g, 1-hydroxycyclohexyl phenyl ketone 3 g, compound (s-15) 2.5 g, compound (a-1) 0.5 g, compound (a-2) 0 .4 g, methylene chloride 155 g.
  • Form (1) A transparent resin substrate containing a compound (A) has a transparent resin layer containing an organic pigment (S) on both sides.
  • Form (2) Transparent glass substrate (“OA-10G manufactured by Nippon Electric Glass Co., Ltd.) (Thickness 150 ⁇ m) ”) having a transparent resin layer containing an organic pigment (S) on both sides.
  • Form (3) Compound (A) on both sides of a resin support (“ Zeonor Film ZF16 ”manufactured by Nippon Zeon Co., Ltd.) And a transparent resin layer containing an organic pigment (S) Form (4): having a transparent resin layer containing an organic pigment (S) on both sides of a resin support Form (5): Compound (A) and Compound (S Form (6): having a transparent resin layer containing compound (S) on both sides of the transparent glass substrate Form (7): made of transparent resin containing compound (A) Has resin layers on both sides of the substrate
  • Substrate 11 First optical layer 12: Second optical layer 13: Third optical layer 14: Fourth optical layer 111: Camera image 112: White plate 113: Example of central portion of white plate 114: White plate Example 121: Camera image 122: Light source 123: Example of a ghost around the light source

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Multimedia (AREA)
  • Signal Processing (AREA)
  • Optical Filters (AREA)
  • Blocking Light For Cameras (AREA)
  • Solid State Image Pick-Up Elements (AREA)

Abstract

La présente invention aborde le problème de la fourniture d'un filtre optique qui est capable de supprimer l'ombrage de couleur et l'effet fantôme dans une image de caméra tout en présentant des caractéristiques de transmittance de lumière élevée dans la région de longueur d'onde de lumière visible, et a une résistance à la chaleur appropriée de telle sorte que ses caractéristiques optiques peuvent être maintenues même après une exposition à long terme à une température élevée. Le filtre optique selon la présente invention est caractérisé en ce qu'il comprend un matériau de base qui satisfait une exigence (a), et ayant une multicouche diélectrique formée sur au moins un côté du matériau de base. (a) : le matériau de base comprend une couche contenant un pigment organique (S) qui a une absorption maximum dans une plage de longueur d'onde comprise entre 900 nm et 1200 nm, inclus.
PCT/JP2019/007035 2018-02-27 2019-02-25 Filtre optique et dispositif utilisant le filtre optique Ceased WO2019167876A1 (fr)

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JP2020503489A JP7207395B2 (ja) 2018-02-27 2019-02-25 光学フィルターおよび光学フィルターを用いた装置
CN201980011899.8A CN111684320B (zh) 2018-02-27 2019-02-25 光学滤波器、固体摄像装置及照相机模块

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