WO2018180482A1 - Composition transmettant la lumière infrarouge - Google Patents

Composition transmettant la lumière infrarouge Download PDF

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Publication number
WO2018180482A1
WO2018180482A1 PCT/JP2018/009875 JP2018009875W WO2018180482A1 WO 2018180482 A1 WO2018180482 A1 WO 2018180482A1 JP 2018009875 W JP2018009875 W JP 2018009875W WO 2018180482 A1 WO2018180482 A1 WO 2018180482A1
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group
infrared light
pigment
color material
meth
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PCT/JP2018/009875
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English (en)
Japanese (ja)
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大貴 木本
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株式会社Ｄｎｐファインケミカル
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Publication of WO2018180482A1 publication Critical patent/WO2018180482A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters

Definitions

  • the composition and type of pigments of each color can be adjusted to some extent, but the pigment has a slight absorption in the near-infrared region.
  • the transmittance in the near-infrared region is not always sufficient. As a result, the infrared ray is prevented from passing, and the sensor or the like may not function sufficiently. For this reason, there has been a strong demand for the development of an infrared light transmissive composition that has sufficient light blocking properties in the visible light region and has high light transmittance in the near infrared region.
  • an infrared light transmission type composition that hardly transmits light in the visible light region and greatly improves the transmittance in the near infrared region.
  • X 1 and X 2 are hydrogen atoms.
  • X 1 and X 2 are chlorine atoms.
  • X 1 and X 2 are phenyl groups.
  • Blue color material As the blue color material (blue pigment), C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like. These may be used individually by 1 type, and 2 or more types may be mixed and used for them.
  • an azo pigment an isoindoline pigment, or a quinophthalone pigment.
  • Pigment Orange 1 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, etc.
  • Orange materials range pigments
  • Black color materials such as carbon black
  • Examples of the dye molecule (pigment molecule) serving as a base skeleton of the acidic dye derivative include anthraquinone pigments, diketopyrrolopyrrole pigments, azo pigments, quinophthalone pigments, dioxazine pigments, and phthalocyanine pigments.
  • the acidic dye derivative include a compound represented by the following formula (8), a compound represented by the following formula (9) (a sulfonated derivative of CI Pigment Red 177), and the following formula (10):
  • Examples thereof include long-chain alkylaminosulfonates composed of anions represented by the following formula (11).
  • the red colorant is an anthraquinone pigment
  • the yellow colorant is an isoindoline pigment
  • light is easily blocked in all regions of 460 nm to 500 nm, 500 nm to 540 nm, and 600 nm to 750 nm. Is particularly preferred.
  • the yellow color material is an azo pigment
  • light in the region of 500 nm to 540 nm or 600 nm to 750 nm can be easily blocked.
  • R 1 represents a hydrogen atom or a methyl group
  • A represents a divalent linking group
  • R 2 and R 3 each independently represent a hydrogen atom or a hydrocarbon group that may contain a hetero atom.
  • R 2 and R 3 may be bonded to each other to form a ring structure.
  • the compound represented by the general formula (3) is an example of “halogen compound such as halogenated aryl, halogenated alkyl, halogenated aralkyl”.
  • R b , R b ′ and R b ′′ each independently represent a hydrogen atom; an acidic group or an ester group thereof; a linear chain having 1 to 20 carbon atoms which may have a substituent A branched or cyclic alkyl group; an optionally substituted vinyl group, a phenyl group or a benzyl group; or —O—R f , wherein R f is an optionally substituted carbon number A linear, branched or cyclic alkyl group having 1 to 20; an optionally substituted vinyl group, phenyl group or benzyl group; or a (meth) acryloyl group via an alkylene group having 1 to 4 carbon atoms
  • X represents a chlorine atom, a bromine atom or an iodine atom
  • the compound represented by the general formula (4) is an example of a phosphoric acid compound.
  • R c and R d each independently have a hydrogen atom; a hydroxyl group; a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms; and a substituent.
  • the basic block copolymer obtained by (co) polymerization of the a monomer or a salt-type dispersant thereof can be finely dispersed or dispersed and can maintain good dispersion stability.
  • the infrared light transmission composition of the present invention has a low transmittance in the visible light region and a high transmittance in the near infrared region.
  • a carboxy group-containing monomer is also preferable.
  • the carboxy group-containing monomer refers to a monomer containing a copolymerizable unsaturated double bond and a carboxy group.
  • Examples of the carboxy group-containing monomer include (meth) acrylic acid, vinyl benzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, and (meth) acrylic acid dimer. .
  • an addition reaction product of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and a cyclic anhydride such as maleic anhydride, phthalic anhydride, cyclohexanedicarboxylic acid anhydride; ⁇ -carboxy- Examples include polycaprolactone mono (meth) acrylate.
  • the carboxy group precursor include a carboxy group-containing monomer using an acid anhydride such as maleic anhydride, itaconic anhydride, and citraconic anhydride.
  • (meth) acrylic acid is particularly preferable from the viewpoints of copolymerizability, cost, solubility, and the like.
  • the introduction rate of the macromonomer is not particularly limited, but it is preferably introduced in an average ratio of 0.1 to 20 in 100 repeating units of the main chain, and 0.3 to 10 It is particularly preferable to introduce them in proportions.
  • Trialkylene glycol ethers ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, alkylene glycol monoalkyl ether acetates such as propylene glycol monoethyl ether acetate; dipropylene glycol monomethyl ether acetate Dialkylene glycol monoalkyl ether acetates such as tate and dipropylene glycol monoethyl ether acetate; Trialkylene glycol monoalkyl ether acetates such as tripropylene glycol monomethyl ether acetate and tripropylene glycol monoethyl ether acetate; Toluene, xylene and the like Aromatic hydrocarbons; ketones such as methyl ethyl ketone, methyl propyl ketone, methyl amyl ketone, cyclopentanone, cyclohexanone, 4-hydroxy-4-methyl-2-
  • the curable resin for example, a photosensitive resin that can be polymerized and cured by visible light, ultraviolet rays, an electron beam, or the like; a thermosetting resin that can be polymerized and cured by heating; a mixture thereof, or the like can be used.
  • the alkali-soluble resin in the present invention in which a radical polymerizable double bond is introduced, is improved in sensitivity, the infrared light transmitting composition is exposed and photocured, and an unexposed portion is developed. As a result, it is preferable because a strong coating film can be formed.
  • a “radical polymerizable double bond” for example, after (co) polymerizing a monomer capable of introducing a radical polymerizable double bond after (co) polymerization, a “radical polymerizable double bond The compound used for introduction is reacted to introduce a radical polymerizable double bond into the side chain.
  • styrene monomers such as styrene and ⁇ -methylstyrene; methyl (meth) acrylate, ethyl (meth) acrylate (n-propyl acrylate), (meth) (Meth) such as isopropyl acrylate, butyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, glycidyl (meth) acrylate, benzyl (meth) acrylate, hydroxyethyl (meth) acrylate, etc.
  • substituents examples include an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, a hydroxyl group, a ketone group, a nitro group, an amine group, and a halogen atom.
  • the lower limit of the number of carbon atoms in the crosslinked cycloaliphatic group is preferably 5 or more, and particularly preferably 7 or more, from the viewpoint of compatibility with other materials and solubility in an alkali developer.
  • the upper limit is preferably 12 or less, and particularly preferably 10 or less.
  • Alkali-soluble resins include maleimides having aliphatic rings such as N-cyclopentylmaleimide, N-cyclohexylmaleimide, N-cyclooctylmaleimide; N-phenylmaleimide, N-methylphenylmaleimide, N-ethylphenylmaleimide, N- Maleimide having an aromatic ring such as dimethylphenylmaleimide, N-diethylphenylmaleimide, N-methoxyphenylmaleimide, N-benzylmaleimide, N-hydroxyphenylmaleimide, N-naphthylmaleimide; Also good.
  • maleimides having aliphatic rings such as N-cyclopentylmaleimide, N-cyclohexylmaleimide, N-cyclooctylmaleimide; N-phenylmaleimide, N-methylphenylmaleimide, N-ethylphenylmaleimide, N- Maleimide
  • the alkali-soluble resin used in the present invention it is easy to adjust the amount of each constituent unit by using an acrylic copolymer having a constituent unit having a hydrocarbon ring separately from the constituent unit having a carboxyl group. This is preferable because the amount of the structural unit having a hydrocarbon ring is increased to easily improve the function of the structural unit.
  • An acrylic copolymer having a carboxyl-containing structural unit and the hydrocarbon ring is prepared by using an ethylenically unsaturated monomer having a hydrocarbon ring as the aforementioned “other copolymerizable monomer”. Can do.
  • Polymerizable polyfunctional compound When the infrared light transmissive composition of the present invention contains an alkali-soluble resin, only the polymerizable functional group of the alkali-soluble resin may be polymerized. It is also preferred that a functional compound is contained. There is no limitation in particular as a polymerizable polyfunctional compound, A well-known polymerizable polyfunctional compound is used. The “polymerizable polyfunctional compound” is not particularly limited as long as it has two or more polymerizable functional groups in one molecule.
  • Trivalent or higher alcohol partial (meth) acrylic acid ester Trivalent or higher alcohol partial (meth) acrylic acid ester; bisphenol-based di (meth) acrylates such as bisphenol A di (meth) acrylate and bisphenol F di (meth) acrylate; neopentyl Rikoruji (meth) acrylate; and the like.
  • PO-modified tri (meth) acrylate isocyanuric acid EO-modified tri (meth) acrylate, isocyanuric acid EO-modified ⁇ -caprolactone-modified tri (meth) acrylate, 1,3,5-triacryloylhexahydro-s-triazine, pentaerythritol tri (Meth) acrylate, dipentaerythritol tri (meth) acrylate tripropionate, etc. are mentioned.
  • Examples include succinic acid-modified products, dipentaerythritol penta (meth) acrylate monopropionate, dipentaerythritol hexa (meth) acrylate, tetramethylolethane tetra (meth) acrylate, oligoester tetra (meth) acrylate and the like.
  • the infrared light transmission type composition of the present invention may contain a polymerization initiator.
  • the polymerization initiator include a thermal polymerization initiator and a photopolymerization initiator.
  • a polymerization initiator may be used individually by 1 type, and may use 2 or more types together.
  • photopolymerization initiators of xanthone derivatives or thioxanthone derivatives include, for example, xanthone, 2,4-isopropylthioxanthone, 2,4-diethylthioxanthone, 1-chloro-4-propoxythioxanthone, 2,4-dichlorothioxanthone, and the like. Can be mentioned.
  • the obtained optical filter was visually observed and judged according to the following criteria. If it is AA or A, it can be used practically. The results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Materials For Photolithography (AREA)

Abstract

La présente invention aborde le problème de la production d'une composition transmettant la lumière infrarouge, présentant une transmittance améliorée destinée à la région infrarouge proche, tout en ne transmettant presque aucune lumière dans la région de lumière visible. Le problème est résolu par une composition transmettant la lumière infrarouge qui contient un colorant, un dispersant et un solvant, et qui est caractérisée en ce que : au moins un colorant rouge, un colorant bleu et un colorant jaune sont contenus dans le colorant; et le dispersant contient une unité constitutive qui est représentée par la formule générale (1). (Dans la formule générale (1), R1 représente un atome d'hydrogène ou un groupe méthyle; A représente un groupe de liaison divalent; R2 et R3 représentent indépendamment un atome d'hydrogène ou un groupe hydrocarboné qui peut contenir un hétéroatome; et R2 et R3 peuvent se combiner l'un avec l'autre pour former une structure annulaire.)
PCT/JP2018/009875 2017-03-30 2018-03-14 Composition transmettant la lumière infrarouge WO2018180482A1 (fr)

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JP2017067907A JP7137295B2 (ja) 2017-03-30 2017-03-30 赤外光透過型組成物
JP2017-067907 2017-03-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109553910A (zh) * 2018-11-28 2019-04-02 宁波力达得为高分子科技有限公司 一种红外透射黑色塑料及其制备方法和用途
CN113050212A (zh) * 2021-01-12 2021-06-29 苏州群烨新材料科技有限公司 红外带通滤光片、其制备方法及具有其的成像设备

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Publication number Priority date Publication date Assignee Title
KR102659438B1 (ko) * 2019-03-11 2024-04-23 후지필름 가부시키가이샤 착색 조성물, 경화막, 패턴 형성 방법, 컬러 필터, 고체 촬상 소자 및 화상 표시 장치
WO2021045193A1 (fr) 2019-09-06 2021-03-11 三菱ケミカル株式会社 Composition colorante photosensible, produit durci, dispositif d'affichage d'image et liquide de dispersion de pigment pour dispositifs d'affichage d'image
US20220334477A1 (en) * 2019-10-07 2022-10-20 Sumitomo Chemical Company, Limited Colored curable resin composition
US20230348748A1 (en) 2020-02-25 2023-11-02 Toray Industries, Inc. Black resin composition, near infrared ray-transmitting light-blocking membrane, decorative substrate, decorative film and colored partition wall for organic el display
JP7466040B1 (ja) 2023-03-31 2024-04-11 ａｒｔｉｅｎｃｅ株式会社 光学積層体及びその製造方法

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JP2010134419A (ja) * 2008-10-31 2010-06-17 Jsr Corp 着色層形成用感放射線性組成物、カラーフィルタ及びカラー液晶表示素子
JP2012022197A (ja) * 2010-07-15 2012-02-02 Dainippon Printing Co Ltd カラーフィルタ基板および表示装置
JP2012082280A (ja) * 2010-10-08 2012-04-26 Dnp Fine Chemicals Co Ltd 顔料分散液、その製造方法、該顔料分散液を用いた感光性着色樹脂組成物、インクジェット用インク並びに電子写真印刷用トナー、及びカラーフィルター
JP2015185096A (ja) * 2014-03-26 2015-10-22 東レ株式会社 遮光膜形成基板及びタッチパネル
JP2016122073A (ja) * 2014-12-24 2016-07-07 株式会社Ｄｎｐファインケミカル 色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置
JP2016177273A (ja) * 2015-03-19 2016-10-06 Jsr株式会社 硬化性組成物、硬化膜、赤外光透過フィルタ及び固体撮像装置
WO2016178346A1 (fr) * 2015-05-01 2016-11-10 富士フイルム株式会社 Film, procédé de production de film, dispositif d'imagerie à semi-conducteurs, et capteur infrarouge
WO2016186050A1 (fr) * 2015-05-20 2016-11-24 富士フイルム株式会社 Composition absorbant les infrarouges, filtre de coupure des infrarouges, stratification, procédé de formation de motifs, et élément de capture d'image à semi-conducteurs
JP2017053979A (ja) * 2015-09-09 2017-03-16 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090296202A1 (en) * 2008-05-30 2009-12-03 Avery Dennison Corporation Infrared light transmission film
JP2010134419A (ja) * 2008-10-31 2010-06-17 Jsr Corp 着色層形成用感放射線性組成物、カラーフィルタ及びカラー液晶表示素子
JP2012022197A (ja) * 2010-07-15 2012-02-02 Dainippon Printing Co Ltd カラーフィルタ基板および表示装置
JP2012082280A (ja) * 2010-10-08 2012-04-26 Dnp Fine Chemicals Co Ltd 顔料分散液、その製造方法、該顔料分散液を用いた感光性着色樹脂組成物、インクジェット用インク並びに電子写真印刷用トナー、及びカラーフィルター
JP2015185096A (ja) * 2014-03-26 2015-10-22 東レ株式会社 遮光膜形成基板及びタッチパネル
JP2016122073A (ja) * 2014-12-24 2016-07-07 株式会社Ｄｎｐファインケミカル 色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置
JP2016177273A (ja) * 2015-03-19 2016-10-06 Jsr株式会社 硬化性組成物、硬化膜、赤外光透過フィルタ及び固体撮像装置
WO2016178346A1 (fr) * 2015-05-01 2016-11-10 富士フイルム株式会社 Film, procédé de production de film, dispositif d'imagerie à semi-conducteurs, et capteur infrarouge
WO2016186050A1 (fr) * 2015-05-20 2016-11-24 富士フイルム株式会社 Composition absorbant les infrarouges, filtre de coupure des infrarouges, stratification, procédé de formation de motifs, et élément de capture d'image à semi-conducteurs
JP2017053979A (ja) * 2015-09-09 2017-03-16 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109553910A (zh) * 2018-11-28 2019-04-02 宁波力达得为高分子科技有限公司 一种红外透射黑色塑料及其制备方法和用途
CN113050212A (zh) * 2021-01-12 2021-06-29 苏州群烨新材料科技有限公司 红外带通滤光片、其制备方法及具有其的成像设备

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