WO2022225002A1 - トリアジン環含有重合体、及びそれを含む膜形成用組成物 - Google Patents

トリアジン環含有重合体、及びそれを含む膜形成用組成物 Download PDF

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WO2022225002A1
WO2022225002A1 PCT/JP2022/018398 JP2022018398W WO2022225002A1 WO 2022225002 A1 WO2022225002 A1 WO 2022225002A1 JP 2022018398 W JP2022018398 W JP 2022018398W WO 2022225002 A1 WO2022225002 A1 WO 2022225002A1
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Prior art keywords
group
carbon atoms
formula
film
triazine ring
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English (en)
French (fr)
Japanese (ja)
Inventor
直樹 中家
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Nissan Chemical Corp
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Nissan Chemical Corp
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Priority to CN202280029867.2A priority Critical patent/CN117222691A/zh
Priority to JP2023515507A priority patent/JPWO2022225002A1/ja
Priority to KR1020237039799A priority patent/KR20230174248A/ko
Publication of WO2022225002A1 publication Critical patent/WO2022225002A1/ja
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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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/0644—Poly(1,3,5)triazines
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/854—Arrangements for extracting light from the devices comprising scattering means
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details

Definitions

  • the present invention relates to a triazine ring-containing polymer and a film-forming composition containing the same.
  • a polymer containing a repeating unit having a triazine ring and an aromatic ring has a high refractive index, and the polymer alone has high heat resistance, high transparency, high refractive index, high solubility, It has already been found that it can achieve low volume shrinkage and is suitable as a film-forming composition for producing electronic devices (Patent Document 1).
  • a linear polymer containing repeating units having a triazine ring and an aromatic ring alone can achieve high heat resistance, high transparency, high refractive index, and high solubility (Patent Reference 2).
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a triazine ring-containing polymer capable of forming a cured film having high solvent resistance while having high transparency and high refractive index.
  • R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a carboxy group, a sulfo group, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, represents a halogenated alkyl group or an alkoxy group having 1 to 10 carbon atoms
  • R 93 and R 94 each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • W 1 and W 2 are each independently a single bond
  • CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom, a C 1-10 alkyl group (provided that these may form a ring), or represents a halogenated alkyl group having 1 to 10 carbon atoms.
  • C ⁇ O, O, S, SO, SO 2 , or NR 97 R 97 is represents a hydrogen atom, an alkyl group having 1 to
  • FIG. 1 is a 1 H-NMR spectrum diagram of the polymer compound [4] obtained in Example 1-1.
  • FIG. 1 is an optical microscope photograph of the surface of a cured film before solvent exposure in Example 2-1.
  • 1 is an optical microscope photograph of the surface of a cured film after exposure to a solvent in Example 2-1.
  • R and R′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group. preferable.
  • the number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20. Considering that the heat resistance of the polymer is further improved, the number of carbon atoms in the alkyl group is 1 to 10. More preferably, 1 to 3 are even more preferable.
  • the structure of the alkyl group is not particularly limited, and may be, for example, linear, branched, cyclic, or a combination of two or more thereof.
  • the number of carbon atoms in the alkoxy group is not particularly limited, it is preferably 1 to 20, and in consideration of further increasing the heat resistance of the polymer, the number of carbon atoms in the alkoxy group is more preferably 1 to 10. 1 to 3 are even more preferred.
  • the structure of the alkyl moiety is not particularly limited, and may be, for example, linear, branched, cyclic, or a combination of two or more thereof.
  • the aralkyl group includes an aralkyl group having a substituent.
  • substituents include halogen atoms, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, nitro groups, and cyano groups.
  • the above Q preferably represents at least one selected from the group represented by formulas (2) to (13).
  • R 1 to R 92 above each independently represent a hydrogen atom, a halogen atom, a carboxy group, a sulfo group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or a halogen atom having 1 to 10 carbon atoms.
  • alkylene groups having 1 to 10 carbon atoms include methylene, ethylene, propylene, trimethylene, tetramethylene and pentamethylene groups.
  • the structure of the alkylene group is not particularly limited, and may be linear, branched, cyclic, or a combination of two or more thereof.
  • the aromatic ring When the aromatic ring is a condensed aromatic ring such as a naphthalene ring, it may have at least one of the above groups as a whole. Further, when A contains a plurality of aromatic rings, at least one halogen atom or halogenated alkyl group may be contained in at least one aromatic ring, but all the aromatic rings are halogen atoms or halogen preferably contain at least one halogenated alkyl group, and more preferably all aromatic rings contain one halogen atom or halogenated alkyl group.
  • Q is preferably at least one represented by formulas (2) and (5) to (13), and formulas (2), (5), (7), (8), (11) to (13) ) is more preferred.
  • Specific examples of the divalent groups represented by the above formulas (2) to (13) include, but are not limited to, those represented by the following formulas.
  • Ph represents a phenyl group. * represents a bond.
  • Q is preferably an m-phenylene group represented by formula (17).
  • Q in formula (1) represents at least one selected from the group represented by formulas (102) to (115), for example. * represents a bond.
  • the number of cross-linking groups in the amino group having a cross-linking group is not particularly limited, and can be any number, but considering the balance between solvent resistance and solubility in organic solvents, 1 to 4 is preferred, 1 to 2 is more preferred, and 1 is even more preferred.
  • the amino group having a cross-linking group has a plurality of cross-linking groups
  • the plurality of cross-linking groups may have the same structure or different structures.
  • the amino group having a cross-linking group is more preferably represented by the following formula (15), particularly preferably represented by the following formula (16).
  • R 102 represents a cross-linking group. * represents a bond.
  • R 102 has the same meaning as above. * represents a bond.
  • the hydroxy-containing group includes a hydroxy group, a hydroxyalkyl group, and the like, preferably a hydroxyalkyl group having 1 to 10 carbon atoms, more preferably a hydroxyalkyl group having 1 to 5 carbon atoms, and a hydroxy group having 1 to 3 carbon atoms. Alkyl groups are even more preferred.
  • those having an alkylene group having 1 to 5 carbon atoms are preferable, those having an alkylene group having 1 to 3 carbon atoms are preferable, and 1 carbon atom, in consideration of improving heat resistance and high temperature and high humidity resistance. or 2 alkylene groups are more preferred.
  • radical photopolymerization initiators include, for example, BASF trade name: Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI1700, CGI1750, CGI1850 , CG24-61, OXE01, OXE02, Darocure 1116, 1173, MBF, manufactured by BASF Product name: Lucilin TPO, manufactured by UCB Product name: Ebecryl P36, manufactured by Fratetzuri Lamberti Product name: Ezacure KIP150, KIP65LT, KIP100F, KT37, KT55, KTO46, KIP75/B and the like.
  • BASF trade name Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI1700, CGI1750, CGI1850 , CG24-61, OXE01
  • the base material silicon, glass on which indium tin oxide (ITO) is formed, glass on which indium zinc oxide (IZO) is formed, metal nanowires, polyethylene terephthalate (PET), plastic, glass, A base material made of quartz, ceramics, or the like can be mentioned, and a flexible base material having flexibility can also be used.
  • the calcination temperature is not particularly limited for the purpose of evaporating the solvent, and can be performed at, for example, 110 to 400°C.
  • the baking method is not particularly limited. For example, a hot plate or an oven may be used to evaporate under an appropriate atmosphere such as air, an inert gas such as nitrogen, or vacuum.
  • inorganic light diffusing agents examples include calcium carbonate (CaCO 3 ), titanium oxide (TiO 2 ), barium sulfate (BaSO 4 ), aluminum hydroxide (Al(OH) 3 ), silica (SiO 2 ), and talc.
  • titanium oxide (TiO 2 ) and agglomerated silica particles are preferable, and non-aggregated titanium oxide (TiO 2 ) is more preferable, from the viewpoint of further increasing the light diffusibility of the resulting cured film.
  • These light diffusing agents may be used after being surface-treated with an appropriate surface modifier.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Optics & Photonics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
PCT/JP2022/018398 2021-04-23 2022-04-21 トリアジン環含有重合体、及びそれを含む膜形成用組成物 Ceased WO2022225002A1 (ja)

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CN202280029867.2A CN117222691A (zh) 2021-04-23 2022-04-21 含三嗪环的聚合物以及含有该聚合物的膜形成用组合物
JP2023515507A JPWO2022225002A1 (https=) 2021-04-23 2022-04-21
KR1020237039799A KR20230174248A (ko) 2021-04-23 2022-04-21 트리아진환 함유 중합체, 및 그것을 포함하는 막 형성용 조성물

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JP2021073335 2021-04-23
JP2021-073335 2021-04-23

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0987385A (ja) * 1995-09-19 1997-03-31 Neos Co Ltd ポリアミン樹脂及びその製造方法
JP2004156001A (ja) * 2002-11-07 2004-06-03 Sanei Kagaku Kk フェノール性水酸基を含有するトリアジンジハライド及び芳香族（ポリ）グアナミン、並びにその組成物
WO2015098787A1 (ja) * 2013-12-24 2015-07-02 日産化学工業株式会社 トリアジン環含有重合体およびそれを含む組成物
WO2015098788A1 (ja) * 2013-12-24 2015-07-02 日産化学工業株式会社 トリアジン系重合体含有組成物
WO2021079977A1 (ja) * 2019-10-25 2021-04-29 日産化学株式会社 トリアジン環含有重合体およびそれを含む膜形成用組成物
WO2021079991A1 (ja) * 2019-10-25 2021-04-29 日産化学株式会社 トリアジン環含有重合体およびそれを含む膜形成用組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101950714B1 (ko) 2009-05-07 2019-02-21 닛산 가가쿠 가부시키가이샤 트리아진환 함유 중합체 및 그것을 포함하는 막 형성용 조성물
JP5885256B2 (ja) 2010-08-30 2016-03-15 国立大学法人岩手大学 トリアジン環含有重合体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0987385A (ja) * 1995-09-19 1997-03-31 Neos Co Ltd ポリアミン樹脂及びその製造方法
JP2004156001A (ja) * 2002-11-07 2004-06-03 Sanei Kagaku Kk フェノール性水酸基を含有するトリアジンジハライド及び芳香族（ポリ）グアナミン、並びにその組成物
WO2015098787A1 (ja) * 2013-12-24 2015-07-02 日産化学工業株式会社 トリアジン環含有重合体およびそれを含む組成物
WO2015098788A1 (ja) * 2013-12-24 2015-07-02 日産化学工業株式会社 トリアジン系重合体含有組成物
WO2021079977A1 (ja) * 2019-10-25 2021-04-29 日産化学株式会社 トリアジン環含有重合体およびそれを含む膜形成用組成物
WO2021079991A1 (ja) * 2019-10-25 2021-04-29 日産化学株式会社 トリアジン環含有重合体およびそれを含む膜形成用組成物

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TW202309148A (zh) 2023-03-01
CN117222691A (zh) 2023-12-12
JPWO2022225002A1 (https=) 2022-10-27
KR20230174248A (ko) 2023-12-27

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