WO2017051680A1 - Composé ester d'oxime et initiateur de polymérisation contenant ledit composé - Google Patents

Composé ester d'oxime et initiateur de polymérisation contenant ledit composé Download PDF

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Publication number
WO2017051680A1
WO2017051680A1 PCT/JP2016/075660 JP2016075660W WO2017051680A1 WO 2017051680 A1 WO2017051680 A1 WO 2017051680A1 JP 2016075660 W JP2016075660 W JP 2016075660W WO 2017051680 A1 WO2017051680 A1 WO 2017051680A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
compound
represented
polymerizable composition
Prior art date
Application number
PCT/JP2016/075660
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English (en)
Japanese (ja)
Inventor
武雄 大石
貴之 伊香賀
木村 正樹
柳澤 智史
Original Assignee
株式会社Adeka
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 株式会社Adeka filed Critical 株式会社Adeka
Priority to JP2017541497A priority Critical patent/JP6799540B2/ja
Priority to CN201680033904.1A priority patent/CN107635960B/zh
Priority to KR1020177033341A priority patent/KR102604868B1/ko
Publication of WO2017051680A1 publication Critical patent/WO2017051680A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/44Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the polymerizable composition is obtained by adding a polymerization initiator to an ethylenically unsaturated compound and can be polymerized and cured by irradiating energy rays (light). Therefore, a photocurable ink, a photosensitive printing plate, Used in various photoresists.
  • Patent Documents 1 to 3 propose using an oxime ester compound as a polymerization initiator used in the polymerizable composition.
  • a highly transparent cured product obtained from a polymerizable composition has been demanded in the market.
  • an object of the present invention is to provide a novel compound that is highly soluble in a solvent and useful as a highly sensitive polymerization initiator, a polymerization initiator using the compound, a polymerizable composition containing the polymerization initiator, And it is providing the hardened
  • the present invention achieves the above object by providing a novel oxime ester compound represented by the following general formula (I) and a polymerization initiator containing the oxime ester compound.
  • R 16 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms
  • R 11 and R 12 each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms
  • the hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms represented by R 11 and R 12 is a halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl Group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group, isocyanate group or heterocyclic group-
  • the oxime ester compound of the present invention is a novel compound represented by the above general formula (I).
  • the oxime ester compound has geometric isomers due to oxime double bonds, but these are not distinguished. That is, in the present specification, the compound represented by the above general formula (I) and the exemplified compound thereof represent a mixture of both or one of them, and are not limited to structures showing isomers.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by R 11 to R 17 and R 21 to R 23 in the general formulas (I) and (II) is not particularly limited, An alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Represents an arylalkyl group or the like;
  • alkyl group having 1 to 20 carbon atoms examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, heptyl, octyl, isooctyl. 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl and the like.
  • the oxime ester compound in which at least one of R 6 , R 7 , R 8 , R 9 and R 10 in the general formula (I) is an electron-withdrawing group has high sensitivity when used as a polymerization initiator. This is preferable.
  • the oxime ester compound in which R 12 in the general formula (I) is a methyl group is preferable because it has high sensitivity when used as a polymerization initiator.
  • the polymerizable composition of the present invention contains the polymerization initiator and an ethylenically unsaturated compound as essential components.
  • an ethylenically unsaturated compound having an acid group such as a carboxyl group (hereinafter also referred to as a compound having alkali developability) can be used for the purpose of imparting alkali developability to the polymerizable composition of the present invention.
  • the compound having alkali developability is not particularly limited as long as it is soluble in an aqueous alkali solution.
  • pigments can also be used as the pigment, for example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 9 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148,
  • dyes As the above dyes, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, phthalocyanine dyes And dyes such as cyanine dyes, and a plurality of these may be used in combination.
  • sensitizer excluding oxime ester compound of the present invention
  • surfactant silane coupling agent
  • melamine leveling agent
  • latent additive ethylenically unsaturated compound
  • ethylenically unsaturated compound Monomers to be removed, antifoaming agents, thickeners, thixotropic agents, flame retardants, plasticizers, stabilizers, polymerization inhibitors, UV absorbers, organic fillers, antioxidants, antistatic agents, flow regulators and adhesion promoters
  • resin additives such as can be added.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea.
  • nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea.
  • Examples include compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other, and are methylol groups that are not alkyl etherified.
  • an ultrahigh pressure mercury lamp As a light source for energy rays used for curing the polymerizable composition or colored polymerizable composition of the present invention, an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a medium pressure mercury lamp, a low pressure mercury lamp, a mercury vapor arc lamp, Xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light-emitting diodes, CRT light sources, etc.
  • Step 1 Production of Intermediate 1a> 6.4 g of 3-acetylindole, 0.8 g (4 mmol) of copper (I) iodide, 0.9 g (8 mmol) of cyclohexanediamine (cis-trans mixture), 8.5 g (40 mmol) of tripotassium phosphate, And 18.8 g of toluene were mixed and stirred at room temperature. 8.2 g (40 mmol) of iodobenzene was added dropwise thereto. After completion of the dropping, the reaction was carried out by heating and stirring at an oil bath temperature of 135 ° C. for 18 hours. After completion of the reaction, it was cooled to room temperature.
  • reaction solution was poured into 150 g of ion-exchanged water, 200 g of toluene was added, and oil-water separation was performed with a separatory funnel. After washing the organic layer 3 times with water, white insoluble matter was observed, and it was filtered with a Kiriyama funnel. The filtrate was dried over anhydrous sodium sulfate, and then the solvent was removed to obtain 6.3 g of the following intermediate 1a in a yield of 67%.
  • the oxime ester compound of the present invention when used as a polymerization initiator of the polymerizable composition, a wide range of solvents, raw materials, and the like can be selected, so that the degree of freedom of blending is high, and precipitation of the oxime ester compound is difficult to occur during storage.
  • the polymerizable composition has excellent storage stability and is useful.
  • the oxime ester compound of the present invention is useful as a highly sensitive polymerization initiator used in the polymerizable composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)
  • Indole Compounds (AREA)
  • Optical Filters (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention concerne un composé ester d'oxime représenté par la formule générale (I) dans laquelle au moins un groupe parmi R、R、R、R、R、R、R、R、R et R10 est un groupe représenté par la formule générale (II) dans le composé ester d'oxime. Au moins un groupe parmi R、R、R et R dans la formule générale (I) est de préférence un groupe représenté par la formule générale (II) dans le composé ester d'oxime. En outre, au moins un groupe parmi R、R、R、R et R10 dans la formule générale (I) est de préférence un groupe arracheur d'électrons.
PCT/JP2016/075660 2015-09-25 2016-09-01 Composé ester d'oxime et initiateur de polymérisation contenant ledit composé WO2017051680A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2017541497A JP6799540B2 (ja) 2015-09-25 2016-09-01 オキシムエステル化合物及び該化合物を含有する重合開始剤
CN201680033904.1A CN107635960B (zh) 2015-09-25 2016-09-01 肟酯化合物及含有该化合物的聚合引发剂
KR1020177033341A KR102604868B1 (ko) 2015-09-25 2016-09-01 옥심에스테르 화합물 및 그 화합물을 함유하는 중합 개시제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-188813 2015-09-25
JP2015188813 2015-09-25

Publications (1)

Publication Number Publication Date
WO2017051680A1 true WO2017051680A1 (fr) 2017-03-30

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PCT/JP2016/075660 WO2017051680A1 (fr) 2015-09-25 2016-09-01 Composé ester d'oxime et initiateur de polymérisation contenant ledit composé

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JP (1) JP6799540B2 (fr)
KR (1) KR102604868B1 (fr)
CN (1) CN107635960B (fr)
TW (1) TWI702236B (fr)
WO (1) WO2017051680A1 (fr)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017170465A1 (fr) * 2016-03-29 2017-10-05 株式会社Adeka Composition photosensible
WO2019054281A1 (fr) 2017-09-15 2019-03-21 富士フイルム株式会社 Composition, film, stratifié, filtre de transmission infrarouge, dispositif d'imagerie à semi-conducteurs et capteur infrarouge
WO2020059509A1 (fr) 2018-09-20 2020-03-26 富士フイルム株式会社 Composition durcissable, film durci, filtre de transmission infrarouge, stratifié, élément d'imagerie à l'état solide, capteur, et procédé de formation de motif
WO2020209205A1 (fr) * 2019-04-08 2020-10-15 株式会社Adeka Composé de carbamoyloxime, et initiateur de polymérisation et composition polymérisable contenant ledit composé
WO2020262270A1 (fr) 2019-06-27 2020-12-30 富士フイルム株式会社 Composition, film et capteur optique
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
WO2021132330A1 (fr) 2019-12-26 2021-07-01 住友化学株式会社 Dispositif d'affichage
JPWO2020004601A1 (ja) * 2018-06-29 2021-08-02 株式会社Adeka オキシムエステル化合物およびこれを含有する光重合開始剤
WO2021200278A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable, et dispositif d'affichage
WO2021199748A1 (fr) 2020-03-30 2021-10-07 富士フイルム株式会社 Composition, film et capteur optique
WO2021200276A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable et dispositif d'affichage
WO2021200277A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable, et dispositif d'affichage
WO2022044824A1 (fr) 2020-08-31 2022-03-03 住友化学株式会社 Corps stratifié et dispositif d'affichage
WO2022044822A1 (fr) 2020-08-31 2022-03-03 住友化学株式会社 Composition de résine, film de résine, et dispositif d'affichage
WO2022044823A1 (fr) 2020-08-31 2022-03-03 住友化学株式会社 Corps stratifié et dispositif d'affichage
WO2022065006A1 (fr) 2020-09-28 2022-03-31 富士フイルム株式会社 Procédé de fabrication de stratifié, procédé de fabrication de boîtier d'antenne, stratifié et composition
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2022196599A1 (fr) 2021-03-19 2022-09-22 富士フイルム株式会社 Film et photocapteur
WO2022210175A1 (fr) 2021-03-29 2022-10-06 富士フイルム株式会社 Composition photosensible noire, procédé de fabrication de composition photosensible noire, film durci, filtre coloré, film de protection contre la lumière, élément optique, élément de capture d'image à semi-conducteurs et unité de phare
WO2022230326A1 (fr) 2021-04-28 2022-11-03 住友化学株式会社 Film durci, et dispositif d'affichage
WO2022230327A1 (fr) 2021-04-28 2022-11-03 住友化学株式会社 Film durci, et dispositif d'affichage
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WO2023054142A1 (fr) 2021-09-29 2023-04-06 富士フイルム株式会社 Composition, résine, film et capteur optique

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DE2707268A1 (de) * 1977-02-19 1978-08-31 Hoechst Ag Indol-3-carbaldehyd-oxime und verfahren zu ihrer herstellung
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FR2244499A1 (en) * 1973-06-07 1975-04-18 Delalande Sa Indol-3-ylformaldoxime carbamates - for treating anxiety epilepsy, cardiac arrhythmias, asthma, intestinal spasm, peptic ulcer, cardiac insufficiency
DE2707268A1 (de) * 1977-02-19 1978-08-31 Hoechst Ag Indol-3-carbaldehyd-oxime und verfahren zu ihrer herstellung
JP2006516246A (ja) * 2002-12-03 2006-06-29 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド ヘテロ芳香族基を有するオキシムエステル光開始剤
JP2005215378A (ja) * 2004-01-30 2005-08-11 Toyo Ink Mfg Co Ltd 感光性着色組成物およびカラーフィルタ
JP2012088575A (ja) * 2010-10-20 2012-05-10 Jsr Corp 感放射線性組成物、硬化膜、及びそれらの形成方法
WO2013008652A1 (fr) * 2011-07-08 2013-01-17 新日鉄住金化学株式会社 Initiateur de photopolymérisation, composition photosensible et article durci

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017170465A1 (fr) * 2016-03-29 2017-10-05 株式会社Adeka Composition photosensible
WO2019054281A1 (fr) 2017-09-15 2019-03-21 富士フイルム株式会社 Composition, film, stratifié, filtre de transmission infrarouge, dispositif d'imagerie à semi-conducteurs et capteur infrarouge
JPWO2020004601A1 (ja) * 2018-06-29 2021-08-02 株式会社Adeka オキシムエステル化合物およびこれを含有する光重合開始剤
JP7394759B2 (ja) 2018-06-29 2023-12-08 株式会社Adeka オキシムエステル化合物およびこれを含有する光重合開始剤
EP3819291A4 (fr) * 2018-06-29 2022-04-27 Adeka Corporation Composé ester d'oxime et initiateur de photopolymérisation le contenant
WO2020059509A1 (fr) 2018-09-20 2020-03-26 富士フイルム株式会社 Composition durcissable, film durci, filtre de transmission infrarouge, stratifié, élément d'imagerie à l'état solide, capteur, et procédé de formation de motif
WO2020209205A1 (fr) * 2019-04-08 2020-10-15 株式会社Adeka Composé de carbamoyloxime, et initiateur de polymérisation et composition polymérisable contenant ledit composé
WO2020262270A1 (fr) 2019-06-27 2020-12-30 富士フイルム株式会社 Composition, film et capteur optique
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
WO2021132330A1 (fr) 2019-12-26 2021-07-01 住友化学株式会社 Dispositif d'affichage
WO2021199748A1 (fr) 2020-03-30 2021-10-07 富士フイルム株式会社 Composition, film et capteur optique
WO2021200277A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable, et dispositif d'affichage
WO2021200278A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable, et dispositif d'affichage
WO2021200276A1 (fr) 2020-03-31 2021-10-07 住友化学株式会社 Composition de résine durcissable et dispositif d'affichage
WO2022044822A1 (fr) 2020-08-31 2022-03-03 住友化学株式会社 Composition de résine, film de résine, et dispositif d'affichage
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WO2022210175A1 (fr) 2021-03-29 2022-10-06 富士フイルム株式会社 Composition photosensible noire, procédé de fabrication de composition photosensible noire, film durci, filtre coloré, film de protection contre la lumière, élément optique, élément de capture d'image à semi-conducteurs et unité de phare
WO2022230326A1 (fr) 2021-04-28 2022-11-03 住友化学株式会社 Film durci, et dispositif d'affichage
WO2022230327A1 (fr) 2021-04-28 2022-11-03 住友化学株式会社 Film durci, et dispositif d'affichage
WO2023032545A1 (fr) 2021-08-31 2023-03-09 富士フイルム株式会社 Procédé de production de produit durci, procédé de production de stratifié, procédé de fabrication de dispositif à semi-conducteur et liquide de traitement
WO2023054142A1 (fr) 2021-09-29 2023-04-06 富士フイルム株式会社 Composition, résine, film et capteur optique

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TWI702236B (zh) 2020-08-21
CN107635960A (zh) 2018-01-26
KR102604868B1 (ko) 2023-11-22
JP6799540B2 (ja) 2020-12-16
CN107635960B (zh) 2022-02-01
TW201716448A (zh) 2017-05-16
KR20180058657A (ko) 2018-06-01

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