WO2021157596A1 - 硬化性組成物、硬化物、電子デバイス、表示装置、光学部材、重合体、感光性組成物、パターンおよび化合物 - Google Patents

硬化性組成物、硬化物、電子デバイス、表示装置、光学部材、重合体、感光性組成物、パターンおよび化合物 Download PDF

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Publication number
WO2021157596A1
WO2021157596A1 PCT/JP2021/003835 JP2021003835W WO2021157596A1 WO 2021157596 A1 WO2021157596 A1 WO 2021157596A1 JP 2021003835 W JP2021003835 W JP 2021003835W WO 2021157596 A1 WO2021157596 A1 WO 2021157596A1
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Prior art keywords
curable composition
compound
group
general formula
composition according
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PCT/JP2021/003835
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English (en)
French (fr)
Japanese (ja)
Inventor
譲 兼子
貴志 青木
勇紀 今泉
大昌 岩田
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Central Glass Co Ltd
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Central Glass Co Ltd
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Priority to CN202180013158.0A priority Critical patent/CN115087686A/zh
Priority to JP2021575820A priority patent/JPWO2021157596A1/ja
Priority to KR1020227031031A priority patent/KR20220139947A/ko
Priority to US17/759,828 priority patent/US20230098559A1/en
Publication of WO2021157596A1 publication Critical patent/WO2021157596A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • 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
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1444—Monoalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/28—Treatment by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/04—Epoxynovolacs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/10—Transparent films; Clear coatings; Transparent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets

Definitions

  • epoxy resins are used in a wide range of applications because they are excellent in moldability without curing shrinkage during polymerization or film formation, and also have excellent adhesion to substrates.
  • the present inventors have conducted a diligent study in view of the above problems. Through the study, the present inventors have newly found that the curable composition containing the first compound described later has excellent adhesion to the substrate. Then, based on this new finding, the present invention was completed.
  • R represents a hydrogen atom or a monovalent organic group.
  • X represents a divalent organic group and represents Rf 1 is a fluorine-containing alkyl group and Rf 2 is a fluorine-containing alkyl group.
  • XY in the description of the numerical range means X or more and Y or less unless otherwise specified.
  • X to 5% by mass means "1% by mass or more and 5% by mass or less”.
  • electronic device refers to an element to which electronic engineering technology is applied, such as a semiconductor chip, a semiconductor element, a printed wiring board, an electric circuit display device, an information communication terminal, a light emitting diode, a physical battery, and a chemical battery. , Devices, final products, etc.
  • the first compound preferably contains a compound represented by the following general formula (1).
  • the cured product of the polymerizable composition of the present embodiment has excellent adhesion to the substrate due to the epoxy group. Further, the cured product of the polymerizable composition of the present embodiment has a low refractive index due to the fluorine-containing alkyl group contained in the first compound. Therefore, the polymerizable composition of the present embodiment can be suitably used as a material for producing a resin film constituting an electronic device or an optical member. Further, the first compound contained in the polymerizable composition of the present embodiment has excellent stability even though it is a compound having a hydroxyl group and an epoxy group.
  • R in the general formula (1) is a hydrogen atom or a monovalent organic group
  • examples of the monovalent organic group include an alkyl group having 1 to 10 carbon atoms and an alkoxy group.
  • the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group and a heptyl group.
  • Rf 1 and Rf 2 in the general formula (1) are fluorine-containing alkyl groups and may be the same or different from each other.
  • the fluorine-containing alkyl group is preferably a linear or branched fluoroalkyl group having 1 to 10 carbon atoms, and more preferably a linear or branched fluoroalkyl group having 1 to 6 carbon atoms. It is an alkyl group, and even more preferably a linear or branched fluoroalkyl group having 1 to 3 carbon atoms.
  • the fluorine-containing alkyl group is preferably a perfluoroalkyl group.
  • Polyglycidyl ethers such as polyglycidyl ether, 1,6-hexanediol diglycidyl ether, sorbitol polyglycidyl ether, pentaerythritol polyglycidyl ether, resorcinol diglycidyl ether, neopentyl glycol diglycidyl ether, hydrogenated bisphenol A type diglycidyl ether And so on.
  • the second compound is not limited to these.
  • Examples of the polymer having an epoxy structure include a polymer obtained by polymerizing or copolymerizing a (meth) acrylate-based monomer having an epoxy structure.
  • Examples of the (meth) acrylate-based monomer having an epoxy structure include monofunctional epoxys such as glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether (abbreviation: 4HBAGE: manufactured by Mitsubishi Chemical Co., Ltd.), and 3,4-epoxycyclohexyl. Examples thereof include methyl methacrylate (trade name: Cyclomer M100: manufactured by Daicel).
  • the amount thereof is, for example, 20% by mass or more and 80% by mass or less, preferably 30% by mass, based on the total solid content of the polymerizable composition. It is 70% by mass or less.
  • the amount of the reactive compound is, for example, 40% by mass or more and 80% by mass or less, preferably 50% by mass or more and 70% by mass or less, based on the first compound contained in the polymerizable composition.
  • the polymerizable composition of the present embodiment is an additive such as a solvent, a photosensitizer, a plasticizer, a coupling agent, a surfactant, an adhesion aid, a sensitizer, and a filler, depending on the properties desired for the application. May include.
  • the present inventors are a compound containing (i) the above-mentioned first compound, (ii) a photocationic polymerization initiator, and (iii) an aromatic ring skeleton and / or an alicyclic skeleton, and per molecule.
  • a curable composition photocurable adhesive
  • a compound (P) in which the total number of hydroxy groups and the number of epoxy groups is 2 or more is suitable for producing a foldable display. ..
  • the cured product of the photocurable adhesive of the present embodiment contains a structure derived from an alkyl fluoride group and an oxygen atom (hydroxy group), so that the interaction between the polymers in the cured product is unknown. Is considered to be smaller (it is presumed that the large electron attraction of the alkyl fluoride group is related). It is considered that this small interaction leads to the flexibility of the cured product and, by extension, the bending resistance.
  • the balance of various performances can be improved.
  • the compound (P) having a hydroxy group a compound in which the glycidyl group is replaced with a hydroxy group in the above epoxy resin can be mentioned. That is, bisphenol A type phenol resin, bisphenol F type phenol resin, novolak resin, resol resin and the like can be mentioned.
  • the hydroxy group that the compound (P) can have may be an alcoholic hydroxy group or a phenolic hydroxy group.
  • the amount of the first compound is adjusted so that the number of moles of the first compound contained in 100 g of the non-volatile component of the curable composition (photocurable adhesive) is 0.04 to 0.4 mol. It is preferable to adjust.
  • the number of moles is more preferably 0.05 to 0.4 mol, still more preferably 0.1 to 0.3 mol.
  • Examples of other optional components include organic solvents, plasticizers, coupling agents, surfactants, adhesion aids, sensitizers, fillers and the like.
  • the monovalent organic group of R' preferably contains a polymerizable group.
  • a photosensitive resin composition is formed by mixing a polymer containing a structural unit represented by the general formula (2) and a structural unit represented by the following general formula (3), a photopolymerization initiator, and a solvent. You can manufacture things.
  • Glycols, glycol ethers, glycol ether esters, etc. can also be mentioned as usable solvents.
  • Specific examples thereof include Celtor (registered trademark) manufactured by Daicel Co., Ltd. and Highsolve (registered trademark) manufactured by Toho Kagaku Kogyo Co., Ltd.
  • CPI-201S Photoacid generator (photocation generator, that is, cationic polymerization initiator) manufactured by San-Apro.
  • -Irgacure 1173 BASF
  • photoinitiator-Seroxide 2021P Daicel
  • M-310 Toa Synthetic, Tori Methylolpropane PO-modified triacrylate ⁇ Pentaerythritol Terraacrylate: manufactured by Tokyo Kasei, pentaerythritol tetrakis acrylate ⁇ NK ester A-9550: manufactured by Shin-Nakamura Chemical Co., Ltd., dipentaerythritol polyacrylate
  • the photocurable adhesive containing the compound (P), the first compound, and the photocation initiator is useful as a photocurable adhesive and has bending resistance. It was shown that the performance is also preferable for the production of foldable displays.
  • BTHB-epo-containing fluororesin 1 11.20 g, 50 mmol
  • PGMEA 22 mL
  • triethylamine 0.50 g, 5 mmol
  • 4HBAGE 4-hydroxybutyl acrylate glycidyl ether
  • BTHB-epo-containing fluororesin 1 11.20 g, 50 mmol
  • PGMEA 22 mL
  • triethylamine 0.50 g, 5 mmol
  • Calends AOI 3.5 g, 25 mmol
  • BTHB-epo-containing fluororesin 1 11.20 g, 50 mmol
  • PGMEA 22 mL
  • triethylamine 0.50 g, 5 mmol
  • 4HBAGE 3.0 g, 15 mmol, manufactured by Mitsubishi Chemical Corporation
  • C4F9-epo 3.0 g, 15 mmol, Tokyo Chemical Industry Co., Ltd. reagent
  • Photosensitive Resin Composition 3 30 parts by mass of the produced BTHB-epo-containing fluororesin 4, 0.3 parts by mass of Irgacure OXE01 (product of BAF Co., Ltd.) as a photopolymerization initiator, and 70 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) as a solvent. To make a solution. Then, the obtained solution was filtered through a membrane filter having a pore size of 0.2 ⁇ m. In this way, the photosensitive resin composition 3 was prepared.
  • PGMEA propylene glycol monomethyl ether acetate
  • Photosensitive Resin Composition 4 30 parts by mass of the produced BTHB-epo-containing fluororesin 5, 0.3 parts by mass of Irgacure OXE01 (product of BAF Co., Ltd.) as a photopolymerization initiator, and 70 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) as a solvent. To make a solution. Then, the obtained solution was filtered through a membrane filter having a pore size of 0.2 ⁇ m. In this way, the photosensitive resin composition 4 was prepared.
  • PGMEA propylene glycol monomethyl ether acetate

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epoxy Resins (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2021/003835 2020-02-07 2021-02-03 硬化性組成物、硬化物、電子デバイス、表示装置、光学部材、重合体、感光性組成物、パターンおよび化合物 Ceased WO2021157596A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN202180013158.0A CN115087686A (zh) 2020-02-07 2021-02-03 固化性组合物、固化物、电子器件、显示装置、光学部件、聚合物、感光性组合物、图案及化合物
JP2021575820A JPWO2021157596A1 (https=) 2020-02-07 2021-02-03
KR1020227031031A KR20220139947A (ko) 2020-02-07 2021-02-03 경화성 조성물, 경화물, 전자 디바이스, 표시 장치, 광학 부재, 중합체, 감광성 조성물, 패턴 및 화합물
US17/759,828 US20230098559A1 (en) 2020-02-07 2021-02-03 Curable composition, cured product, electronic device, display device, optical member, polymer, photosensitive composition, pattern, and compound

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Application Number Priority Date Filing Date Title
JP2020019398 2020-02-07
JP2020-019398 2020-02-07
JP2020-150682 2020-09-08
JP2020150682 2020-09-08

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CN118786161A (zh) * 2022-03-01 2024-10-15 高新特殊工程塑料全球技术有限公司 衍生自二环戊二烯的共聚物

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JP2002543247A (ja) * 1999-05-04 2002-12-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ポリフッ素化エポキシドおよび関連ポリマーおよび生成方法
JP2003295440A (ja) * 2002-03-29 2003-10-15 Jsr Corp 酸解離性基含有樹脂および感放射線性樹脂組成物
US6924313B1 (en) * 1999-09-23 2005-08-02 Pfizer Inc. Substituted tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
JP2006193426A (ja) * 2003-09-05 2006-07-27 Sankyo Co Ltd 置換された縮環ピリミジン−４（３ｈ）−オン化合物
WO2019147782A1 (en) * 2018-01-26 2019-08-01 Bristol-Myers Squibb Company Aminopyrrolotriazines as kinase inhibitors

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JPH09309943A (ja) * 1996-05-23 1997-12-02 Nippon Telegr & Teleph Corp <Ntt> 可視光硬化性フッ素化樹脂組成物
JP4083399B2 (ja) 2001-07-24 2008-04-30 セントラル硝子株式会社 含フッ素重合性単量体およびそれを用いた高分子化合物

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JP2002543247A (ja) * 1999-05-04 2002-12-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ポリフッ素化エポキシドおよび関連ポリマーおよび生成方法
US6924313B1 (en) * 1999-09-23 2005-08-02 Pfizer Inc. Substituted tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
JP2003295440A (ja) * 2002-03-29 2003-10-15 Jsr Corp 酸解離性基含有樹脂および感放射線性樹脂組成物
JP2006193426A (ja) * 2003-09-05 2006-07-27 Sankyo Co Ltd 置換された縮環ピリミジン−４（３ｈ）−オン化合物
WO2019147782A1 (en) * 2018-01-26 2019-08-01 Bristol-Myers Squibb Company Aminopyrrolotriazines as kinase inhibitors

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US20230098559A1 (en) 2023-03-30
CN115087686A (zh) 2022-09-20
KR20220139947A (ko) 2022-10-17
TW202138357A (zh) 2021-10-16
JPWO2021157596A1 (https=) 2021-08-12

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