WO2017051680A1 - 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 - Google Patents

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 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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WIPO (PCT)
Prior art keywords
group
carbon atoms
compound
represented
polymerizable composition
Prior art date
Application number
PCT/JP2016/075660
Other languages
English (en)
French (fr)
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
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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/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL 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
    • G02F1/00—Devices 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
    • G02F1/01—Devices 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 
    • G02F1/13—Devices 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural 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)
  • Polymers & Plastics (AREA)
  • Nonlinear Science (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Mathematical Physics (AREA)
  • Materials For Photolithography (AREA)
  • Indole Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Optical Filters (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/JP2016/075660 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 WO2017051680A1 (ja)

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)

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

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017170465A1 (ja) * 2016-03-29 2017-10-05 株式会社Adeka 感光性組成物
WO2019054281A1 (ja) 2017-09-15 2019-03-21 富士フイルム株式会社 組成物、膜、積層体、赤外線透過フィルタ、固体撮像素子および赤外線センサ
WO2020059509A1 (ja) 2018-09-20 2020-03-26 富士フイルム株式会社 硬化性組成物、硬化膜、赤外線透過フィルタ、積層体、固体撮像素子、センサ、及び、パターン形成方法
WO2020209205A1 (ja) * 2019-04-08 2020-10-15 株式会社Adeka カルバモイルオキシム化合物並びに該化合物を含有する重合開始剤及び重合性組成物
WO2020262270A1 (ja) 2019-06-27 2020-12-30 富士フイルム株式会社 組成物、膜および光センサ
WO2021039253A1 (ja) 2019-08-30 2021-03-04 富士フイルム株式会社 組成物、膜、光学フィルタ及びその製造方法、固体撮像素子、赤外線センサ、並びに、センサモジュール
WO2021039205A1 (ja) 2019-08-29 2021-03-04 富士フイルム株式会社 組成物、膜、近赤外線カットフィルタ、パターン形成方法、積層体、固体撮像素子、赤外線センサ、画像表示装置、カメラモジュール、及び、化合物
WO2021132330A1 (ja) 2019-12-26 2021-07-01 住友化学株式会社 表示装置
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
WO2021200276A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2021199748A1 (ja) 2020-03-30 2021-10-07 富士フイルム株式会社 組成物、膜及び光センサ
WO2021200277A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2021200278A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2022044823A1 (ja) 2020-08-31 2022-03-03 住友化学株式会社 積層体及び表示装置
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WO2022044822A1 (ja) 2020-08-31 2022-03-03 住友化学株式会社 樹脂組成物、樹脂膜及び表示装置
WO2022065006A1 (ja) 2020-09-28 2022-03-31 富士フイルム株式会社 積層体の製造方法、アンテナインパッケージの製造方法、積層体及び組成物
WO2022131191A1 (ja) 2020-12-16 2022-06-23 富士フイルム株式会社 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ
WO2022130773A1 (ja) 2020-12-17 2022-06-23 富士フイルム株式会社 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ
WO2022196599A1 (ja) 2021-03-19 2022-09-22 富士フイルム株式会社 膜および光センサ
WO2022210175A1 (ja) 2021-03-29 2022-10-06 富士フイルム株式会社 黒色感光性組成物、黒色感光性組成物の製造方法、硬化膜、カラーフィルタ、遮光膜、光学素子、固体撮像素子、ヘッドライトユニット
WO2022230326A1 (ja) 2021-04-28 2022-11-03 住友化学株式会社 硬化膜及び表示装置
WO2022230327A1 (ja) 2021-04-28 2022-11-03 住友化学株式会社 硬化膜及び表示装置
WO2023032545A1 (ja) 2021-08-31 2023-03-09 富士フイルム株式会社 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液
WO2023054142A1 (ja) 2021-09-29 2023-04-06 富士フイルム株式会社 組成物、樹脂、膜および光センサ

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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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WO2017170465A1 (ja) * 2016-03-29 2017-10-05 株式会社Adeka 感光性組成物
WO2019054281A1 (ja) 2017-09-15 2019-03-21 富士フイルム株式会社 組成物、膜、積層体、赤外線透過フィルタ、固体撮像素子および赤外線センサ
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 (en) * 2018-06-29 2022-04-27 Adeka Corporation OXIMESTER COMPOUND AND PHOTOPOLYMERIZATION INITIATOR CONTAINING IT
WO2020059509A1 (ja) 2018-09-20 2020-03-26 富士フイルム株式会社 硬化性組成物、硬化膜、赤外線透過フィルタ、積層体、固体撮像素子、センサ、及び、パターン形成方法
WO2020209205A1 (ja) * 2019-04-08 2020-10-15 株式会社Adeka カルバモイルオキシム化合物並びに該化合物を含有する重合開始剤及び重合性組成物
WO2020262270A1 (ja) 2019-06-27 2020-12-30 富士フイルム株式会社 組成物、膜および光センサ
WO2021039205A1 (ja) 2019-08-29 2021-03-04 富士フイルム株式会社 組成物、膜、近赤外線カットフィルタ、パターン形成方法、積層体、固体撮像素子、赤外線センサ、画像表示装置、カメラモジュール、及び、化合物
WO2021039253A1 (ja) 2019-08-30 2021-03-04 富士フイルム株式会社 組成物、膜、光学フィルタ及びその製造方法、固体撮像素子、赤外線センサ、並びに、センサモジュール
WO2021132330A1 (ja) 2019-12-26 2021-07-01 住友化学株式会社 表示装置
WO2021199748A1 (ja) 2020-03-30 2021-10-07 富士フイルム株式会社 組成物、膜及び光センサ
WO2021200278A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2021200276A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2021200277A1 (ja) 2020-03-31 2021-10-07 住友化学株式会社 硬化性樹脂組成物及び表示装置
WO2022044824A1 (ja) 2020-08-31 2022-03-03 住友化学株式会社 積層体及び表示装置
WO2022044822A1 (ja) 2020-08-31 2022-03-03 住友化学株式会社 樹脂組成物、樹脂膜及び表示装置
WO2022044823A1 (ja) 2020-08-31 2022-03-03 住友化学株式会社 積層体及び表示装置
WO2022065006A1 (ja) 2020-09-28 2022-03-31 富士フイルム株式会社 積層体の製造方法、アンテナインパッケージの製造方法、積層体及び組成物
WO2022131191A1 (ja) 2020-12-16 2022-06-23 富士フイルム株式会社 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ
WO2022130773A1 (ja) 2020-12-17 2022-06-23 富士フイルム株式会社 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ
WO2022196599A1 (ja) 2021-03-19 2022-09-22 富士フイルム株式会社 膜および光センサ
WO2022210175A1 (ja) 2021-03-29 2022-10-06 富士フイルム株式会社 黒色感光性組成物、黒色感光性組成物の製造方法、硬化膜、カラーフィルタ、遮光膜、光学素子、固体撮像素子、ヘッドライトユニット
WO2022230326A1 (ja) 2021-04-28 2022-11-03 住友化学株式会社 硬化膜及び表示装置
WO2022230327A1 (ja) 2021-04-28 2022-11-03 住友化学株式会社 硬化膜及び表示装置
WO2023032545A1 (ja) 2021-08-31 2023-03-09 富士フイルム株式会社 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液
WO2023054142A1 (ja) 2021-09-29 2023-04-06 富士フイルム株式会社 組成物、樹脂、膜および光センサ

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JP6799540B2 (ja) 2020-12-16
JPWO2017051680A1 (ja) 2018-07-12
CN107635960A (zh) 2018-01-26
KR102604868B1 (ko) 2023-11-22
TW201716448A (zh) 2017-05-16

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