CN110317534A - Thermosetting composition, cured film and colored filter - Google Patents

Thermosetting composition, cured film and colored filter Download PDF

Info

Publication number
CN110317534A
CN110317534A CN201910231485.8A CN201910231485A CN110317534A CN 110317534 A CN110317534 A CN 110317534A CN 201910231485 A CN201910231485 A CN 201910231485A CN 110317534 A CN110317534 A CN 110317534A
Authority
CN
China
Prior art keywords
compound
thermosetting composition
cured film
acid
polymer
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
CN201910231485.8A
Other languages
Chinese (zh)
Inventor
木村佑希
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
JNC Corp
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 JNC Corp filed Critical JNC Corp
Publication of CN110317534A publication Critical patent/CN110317534A/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C08G59/40—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 curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4207—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aliphatic
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/08—Anhydrides
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • 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
    • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; 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
    • C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; 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
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D177/12—Polyester-amides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G02F1/133509—Filters, e.g. light shielding masks
    • 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
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G02F1/133519—Overcoatings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epoxy Resins (AREA)
  • Optical Filters (AREA)
  • Polyamides (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention provides a kind of thermosetting composition, cured film and colored filter.The present invention relates to thermosetting compositions, compound (B) and solvent (C) it includes polymer (A), with more than two epoxy groups, the polymer (A) be from more than two anhydride groups (- CO-O-CO-) compound (a) and following formula (1) represented by same intramolecular there is the product of the compound (b) of amino and hydroxyl.Thermosetting composition through the invention and being formed makes heat resistance, the transparency, flatness, each characteristic height of substrate adhesion and the cured film deposited.The cured film may be suitably used in electronic component.In formula (1), R1For divalent organic base.

Description

Thermosetting composition, cured film and colored filter
Technical field
The present invention relates to the passivating films, slow in a kind of insulating materials that can be used to form in electronic component, semiconductor device Rush film, interlayer dielectric, planarization film, the interlayer dielectric in liquid crystal display element, colored filter (color Filter) with the thermosetting composition of protective film etc., the hyaline membrane formed by the thermosetting composition and with described The electronic component of film.
Background technique
In the manufacturing step of the elements such as liquid crystal display element, there is the step of the organic film of various functions including being formed Suddenly.For example, film forming/pattern of film forming/patterning/heat treatment step of black matrix" resist, colored filter resist Change/heat treatment step, film forming/patterning/heat treatment step of protective films of color filters, tin indium oxide (Indium Tin Oxide, ITO) film formation step of conductive film, ITO pattern photoresist film forming/patterning/wet etching/resist Strip step, ITO annealing steps, film forming/heat treatment/friction (polarisation exposure) step of alignment films etc..In these various steps In, for element, have an opportunity to be contacted with the various chemicals such as organic solvent, acid, aqueous slkali, in addition, by sputter come When forming electrode, there is also surfaces to be locally exposed to the situation under high temperature.Therefore, sometimes for the surface for preventing various elements Deterioration, damage, rotten purpose and surface protection film is set.Tolerable manufacture step as described above is required to these protective films Each characteristic of various processing in rapid.Specifically, it is desirable that the chemicals-resistants such as heat resistance, solvent resistance/acid resistance/alkali resistance Property, water resistance, the adhesion to underlay substrates such as glass, the transparency, scratch resistance, coating, flatness, light resistance etc..It is special Be not, with to reliability required by display element requirement characteristic improve, to heat resistance required by display element component, The attenuating of outlet (outgas) when being specifically heat-treated is taken seriously.Its reason is: as described above various being formed When organic film, cross-linking reaction/densification by being heat-treated caused film is carried out always, therefore it is also repeatedly right to penetrate through step Element applies heat.Therefore, if the film on upper layer is formed due to the outlet from lower layer using the protective film for generating a large amount of outlets It is affected, as a result causes the reduction of display quality, the reduction of reliability.
So far, it in order to provide the protective film with high heat resistance, and proposes polyimide material being used as protection Film (patent document 1).In addition, it was also proposed that have the protective film using silicone compositions characterized by high heat resistance and the transparency (patent document 2, patent document 3).Alternatively, proposing the protective film or the use that have using epoxy resin and melamine resin The protective film (patent document 4, patent document 5, patent document 6) of acrylic resin or polyester resin.
However, using in the protective film of polyimide material, in order to prepare polyimides or polyimide precursor (polyamide Acid) solution, and need to have strong solvent so-called polyimides molten using N-Methyl pyrrolidone or gamma-butyrolacton etc. Matchmaker, and there are problems that the organic film of substrate can be dissolved.Especially in the case where being used as the protective film of colored filter, Described problem becomes big problem.In addition, in polyimides, due to passing through the mobile interaction (electric charge transfer (Charge of charge Transfer, CT) interaction) and the edge of optical absorption band is caused to extend to visible light region, therefore there is also colour. On the other hand, using silicone compositions (sol gel film), heat resistance is abundant with the transparency, but due to silane Temperature required for the reaction of alcohol radical finishes also becomes 300 DEG C or more, therefore there is also the deteriorations for the organic film for leading to substrate The problem of cracking (cracking) in the film due to problem or curing shrinkage when thermmohardening.In addition, there is also siloxanes materials - Si-O-Si- the key of material is easy the difficult point of hydrolysis because of aqueous slkali.In addition, in the material using epoxy resin and melamine resin In the case where material, although there is no problem in terms of using solvent or heat treatment temperature, heat resistance is simultaneously insufficient, and produces The problem of raw xanthochromia.Using acrylic material or polyester resin, as basic framework acrylic acid position/it is poly- The heat resistance of esteratic site is also and insufficient, and leads to the problem of outlet.Especially there is also a part of raw materials with not for polyester material The problem of the state remaining of reaction, though it is removed using purification step, increased costs, therefore it is required that being walked without purification Rapid outlet lowers.
On the other hand, the protective film having using the polyesteramide acid with both polyester and amic acid structure is also disclosed (patent document 7).In said case, because esteratic site and amic acid position unevenly exist in the polymer and raw alcohol at Point remaining and outlet lower effect it is limited.
According to the situation, seek a kind of to make high heat resistance (low outlet), other each characteristics especially flatness, thoroughly Bright property, to the adhesion of substrate and the material deposited.
[existing technical literature]
[patent document]
[patent document 1] Japanese Patent Laid-Open No. Sho 62-163016
[patent document 2] Japanese Patent Laid-Open No. Sho 62-242918
[patent document 3] Japanese Patent Laid-Open 7-331178
[patent document 4] Japanese Patent Laid-Open No. Sho 63-131103
[patent document 5] Japanese Patent Laid-Open 8-50289
[patent document 6] Japanese Patent Laid-Open 2013-253263
[patent document 7] Japanese Patent Laid-Open 2008-156546
Summary of the invention
[problem to be solved by the invention]
Problem of the invention is that it is excellent to provide a kind of offer heat resistance (low outlet), flatness, the transparency, adhesion Cured film thermosetting composition and the cured film that is formed by the thermosetting composition, and then provide and a kind of there is institute State the electronic component of cured film.
[technical means to solve problem]
The present inventor carried out in order to solve described problem make great efforts research, as a result by using thermosetting composition and The present invention is completed, the thermosetting composition is comprising making the compound with more than two anhydride groups and in same molecule Copolymer made of the interior compound thermal response with amino and hydroxyl, the compound with more than two epoxy groups and can Dissolve the solvent of these compounds.The present invention includes composition below.
[1] a kind of thermosetting composition, the compound (B) it includes polymer (A), with more than two epoxy groups And solvent (C), the polymer (A) is from compound (a) and following formula (1) institute table with more than two anhydride groups That shows has the product of the compound (b) of amino and hydroxyl in same intramolecular:
In formula (1), R1For divalent organic base.
[2] according to the thermosetting composition of [1] Xiang Suoshu, wherein the compound with more than two anhydride groups (a) for selected from copolymerization composition in comprising aromatic acid dianhydride, aliphatic acid dianhydride and maleic anhydride polymer at least It is a kind of.
[3] according to the thermosetting composition of [1] Xiang Suoshu, wherein the R of the compound (b)1For can branch carbon number 1 Bilvalent radical represented by~10 alkylidene or following formula (2):
-CH2CH2(OCH2CH2)m- (2)
In formula (2), m be 1~9 integer.
[4] according to the thermosetting composition of [1] Xiang Suoshu, wherein the compound with more than two epoxy groups It (B) is the compound with aromatic rings.
[5] a kind of cured film is formed as the thermosetting composition according to any one of [1] to [4].
[6] a kind of colored filter has according to the cured film of [5] Xiang Suoshu as transparent protective film.
[The effect of invention]
The thermosetting composition of the preferred embodiment of the present invention is heat resistance, flatness, the transparency, adhesion and spy It is not material especially excellent in terms of heat resistance, the case where being used as the protective films of color filters of color liquid crystal display device Under, display quality can be improved.It especially acts effectively as using decoration method, pigment dispersion method, electrodeposition process and print process and manufactures Colored filter protective film.In addition, also being used as the protective film and transparent insulating film of various optical materials.
Specific embodiment
1. thermosetting composition of the invention
Thermosetting composition of the invention include polymer (A), the compound (B) with more than two epoxy groups and Solvent (C), the polymer (A) are compound (a) and formula (1) institute for making to have more than two anhydride groups (- CO-O-CO-) Product made of compound (b) thermal response of expression, and the thermosetting composition is characterized in that: relative to polymer (A) 100 parts by weight, the compound (B) with more than two epoxy groups are 10 parts by weight~500 parts by weight.
1-1. polymer (A)
Polymer (A) is compound (b) represented by the compound (a) for making to have more than two anhydride groups and formula (1) Thermal response and obtain.It include aromatic acid dianhydride and aliphatic acid dianhydride, and include in the range of selection compound (a) By polymer made of other polymerizable monomers copolymerization other than maleic anhydride and maleic anhydride (as long as having more than two acid Anhydride group), it can be used selected from least one of these compounds.Hereinafter, in the present specification, it will be " other than maleic anhydride Other polymerizable monomers " be expressed as " other polymerizable monomers ".Spy is had no with other polymerizable monomers of maleic anhydride It does not limit, for the viewpoint of heat resistance, preferably N substituted maleimide amine, indenes (indene), styrene etc..
In the copolymerization of maleic anhydride and other polymerizable monomers, using free-radical polymerized, as initiator, preferably Use thermal free radical initiator.
In addition, at least needing solvent in the synthesis of polymer (A).The solvent can be made directly to remain and consideration is made Liquid or gelatinous composition to operability etc., in addition, can also remove and be made in view of carrying property etc. by the solvent Solid-like composition.
Other compounds other than described in can also including in the range of not undermining the purpose of the present invention.As other raw materials Example, may include chain-transferring agent.
1-1-1. has the compound (a) of more than two anhydride groups
In the present invention, as the raw material to obtain polymer (A), acid dianhydride is used.As acid dianhydride, can enumerate: 3, 3', 4,4'- benzophenone tetracarboxylic dianhydride, 2,2', 3,3'- benzophenone tetracarboxylic dianhydride, 2,3,3', 4'- benzophenone four Carboxylic acid dianhydride, 3,3', 4,4'- diphenyl sulfone tetracarboxylic dianhydride, 2,2', 3,3'- diphenyl sulfone tetracarboxylic dianhydride, 2,3,3', 4'- Diphenyl sulfone tetracarboxylic dianhydride, 3,3', 4,4'- diphenyl ether tetracarboxylic dianhydride, 2,2', 3,3'- diphenyl ether tetracarboxylic dianhydride, 2,3,3', 4'- diphenyl ether tetracarboxylic dianhydride, 2,2- [bis- (3,4- dicarboxyphenyis)] hexafluoropropane dianhydride, 1,2,3,4- fourth Bis- (dehydration the trimellitate) (trade names of alkane tetracarboxylic dianhydride, ethylene glycol；TMEG-100, the new limited public affairs of Japan Chemical share Department), cyclobutane tetracarboxylic dianhydride, methyl cyclobutane tetracarboxylic dianhydride, pentamethylene tetracarboxylic dianhydride, cyclopentanetetracarboxylic's dianhydride, Ethane tetracarboxylic dianhydride and butane tetracarboxylic acid dianhydride.One or more of these compounds can be used.
In addition, the copolymer of maleic anhydride and other polymerizable monomers can be used as with more than two in the present invention The compound of anhydride group.In said case, as other available polymerizable monomers, specifically, can enumerate: N- methyl Maleimide, n-ethylmaleimide, N- propylmaleimide, N- N-cyclohexylmaleimide, N- phenyl Malaysia acyl Imines, N- benzyl maleimide.In addition, can enumerate: isobutene, styrene, indenes, methacrylic acid, methyl methacrylate, Ethyl methacrylate, propyl methacrylate, butyl methacrylate, glycidyl methacrylate, methacrylic acid- 2- hydroxy methacrylate, benzyl methacrylate, methacrylic acid -2- phenoxy ethyl, methacrylic acid -2- phenyl chlorocarbonate, methyl Isobornyl acrylate, methacrylic acid bicyclopentyl ester, 2,2,2-trifluoroethyl methacrylate.
1-1-2. has the compound (b) of amino and hydroxyl in same intramolecular
In the present invention, as the material to obtain polymer (A), there is amino and hydroxyl using in same intramolecular Compound.It as such compound, can enumerate: 2- ethylaminoethanol, 3- amino -1- propyl alcohol, 5- amino -1- amylalcohol, 6- amino -1- Hexanol, 8- amino -1- octanol, 10- amino -1- decyl alcohol, 12- amino -1- lauryl alcohol, 2- (2- amino ethoxy) ethyl alcohol, 2- (4- Aminophenyl) ethyl alcohol, 2- (4- aminocyclohexyl) ethyl alcohol, 4- aminocyclohexanol.The viewpoint of easiness and heat resistance with regard to acquisition For, appropriately 2- ethylaminoethanol, 2- (2- amino ethoxy) ethyl alcohol.Compounds listed herein can also be used together by more than one.
Solvent used in the synthesis of 1-1-3. polymer (A)
It as the concrete example of solvent used in the synthesis to obtain polymer (A), can enumerate: ethyl acetate, second Acid butyl ester, propyl acetate, butyl propionate, ethyl lactate, methoxy menthyl acetate, ethyl methoxyacetate, methoxyacetic acid fourth Ester, ethoxy acetate, ethoxy ethyl acetate, 3- oxygroup methyl propionate, 3- hydroxypropionate, 3- methoxypropionic acid first Ester, 3- methoxypropionate, 3- ethoxypropanoate, 3- ethoxyl ethyl propionate, 2 hydroxy propanoic acid methyl esters, 2- hydroxyl third Propyl propionate, 2- methoxy methyl propionate, 2- methoxypropionate, 2- methoxy propyl propyl propionate, 2- ethoxypropanoate, 2- Ethoxyl ethyl propionate, 2- hydroxy-2-methyl methyl propionate, 2- hydroxy-2-methyl ethyl propionate, 2- methoxyl group -2- methyl-prop Sour methyl esters, 2- ethyoxyl -2 Methylpropionic acid ethyl ester, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, Ethyl acetoacetate, 2-Oxobutyric acid methyl esters, 2-Oxobutyric acid ethyl ester, 4- hydroxy-4-methyl-2-pentanone, 1,4- butanediol, third Glycol monomethyl ether, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetic acid esters, ethylene glycol list Butyl ether acetic acid esters, cyclohexanone, cyclopentanone, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether, Diethylene glycol monoethyl ether acetic acid esters, diethylene glycol monobutyl ether, butyl carbitol acetate, diethylene glycol dimethyl ether, diethyl Glycol diethyl ether and diethylene glycol methyl ethyl ether.Solvent can be one kind of these solvents, can also for two kinds of these solvents with On mixture.
1-1-4. includes molecular weight regulator used in the synthesis of the copolymer of maleic anhydride
In the synthesis of the copolymer comprising maleic anhydride, molecular weight regulator can also be contained, also to inhibit molecule quantitative change Height, and show excellent storage stability.It as molecular weight regulator, can enumerate: thio-alcohol, xanthan acids, quinones, hydroquinones And 2,4- diphenyl -4-methyl-1-pentene etc..
It as the concrete example of molecular weight regulator, can enumerate: 2-hydroxy-1,4-naphthoquinone, benzoquinones, 1,4-naphthoquinone, Isosorbide-5-Nitrae-two Hydroxyl naphthalene, 2,5- di-t-butyl quinhydrones, quinhydrones, methylnaphthohydroquinone, tert-butyl hydroquinone, first quinone (methoquinone), 1,4-benzoquinone, Methyl -1,4-benzoquinone, tert-butyl-p-benzo-quinone, anthraquinone, n-hexyl mercaptan, n octylmercaptan, positive dodecylmercaptan, tertiary dodecyl sulphur Alcohol, thioglycolic acid, dimethyl yellow ortho acid thioether, diisopropyl xanthic acid disulfide, 2,4- diphenyl -4-methyl-1-pentene Deng.
Molecular weight regulator can be used alone, and also can be used in combination two or more.
The synthetic method of 1-1-5. polymer (A)
Polymer used in the present invention (A) is the compound (a) for making to have more than two anhydride groups and formula (1) institute Compound (b) thermal response of expression and obtain.At this time, it may be necessary to which the molal quantity of each functional group of acid anhydrides and formula (1) is represented The molal quantity of each functional group of compound (b) be set as range below.Herein, so-called functional group refers to anhydride group, ammonia Base, hydroxyl.
0.5≦X≦5.0
The molal quantity of X=anhydride group/(molal quantity+hydroxyl molal quantity of amino)
If the range, then polymer is high to the dissolubility of solvent and heat resistance, flatness, the adhesion of composition are good It is good, more preferably 0.7≤X≤4.0, and then more preferably 1.0≤X≤3.0.
If reacting and swimmingly carrying out using reaction dissolvents more than 80 parts by weight relative to 100 parts by weight of solute, because This is preferably.Reaction is reacted 0.2 hour~20 hours at 40 DEG C~200 DEG C.
On the other hand, it in the compound with anhydride group, can also be used maleic anhydride and other as described above Polymer made of polymerizable monomer copolymerization.When the free radical polymerization, preferably 40 DEG C~120 DEG C of reaction temperature is more excellent It is selected as 60 DEG C~80 DEG C of reaction temperature.It after free radical polymerization, is cooled to room temperature, compound represented by adding type (1), And it is reacted 0.1 hour~6 hours at 40 DEG C~200 DEG C.
In the polymer (A) synthesized in this way, even if the compound (b) represented by formula (1) to copolymer or Using the dissolubility of solvent it is low in the case where, after thermal response, can also become uniform transparent liquid and be formed zero defect and uniformly Film.On the contrary, not making the compound thermal response with more than two hydroxyls after the polymerization of free-radical polymerized object and simple In the case that ground is added in system, the case where precipitation there is also the compound with more than two hydroxyls, in the situation Under, uniform film can not be formed.Therefore, by being derived as polymer (A), flawless film can be formed.
The weight average molecular weight of polymer (A) obtained is preferably 1,000~1,000,000, more preferably 2,000 ~500,000.If being in these ranges, coating, flatness are good.
Weight average molecular weight in this specification is to utilize gel permeation chromatography (Gel Permeation Chromatography, GPC) (tubing string temperature: 35 DEG C, flow velocity: 1ml/min) and the value of polystyrene conversion that finds out.Standard Polystyrene using molecular weight be 645~132,900 polystyrene (for example, Agilent Technologies (Agilent Technologies) polystyrene calibration set group (calibration kit) PL2010-0102 of limited liability company), tubing string (PLgel MIXED)-D (Agilent Technologies (Agilent Technologies) limited liability company) is mixed using PL gel, Tetrahydrofuran (Tetrahydrofuran, THF) can be used to be measured as mobile phase.Commercially available product in this specification Weight average molecular weight is catalogue (catalogue) record value.
1-2. has the compound (B) of more than two epoxy groups
Epoxide used in the present invention is the compound that each molecule has more than two epoxy groups.Have The compound (B) of more than two epoxy groups can be one kind, can also be two or more.
1-2-1. has the example of the compound (B) of more than two epoxy groups
The example of compound (B) with more than two epoxy groups is bisphenol A type epoxy compound, bisphenol F type epoxy Compound, diglycidyl ether type epoxy compound, glycidyl ester type epoxy compound, biphenyl type epoxy compound, phenol phenol Novolac type ring oxygen compound, cresol novolak type epoxy compound, bisphenol A novolac type ring oxygen compound, aliphatic Poly epihydric alcohol ether compound, ring type aliphatic epoxy compound, the polymer of monomer with epoxy group, with epoxy group The copolymer of monomer and other monomers and epoxide with siloxanes key knot position.
The concrete example of the commercially available product of bisphenol A type epoxy compound is jER 828, jER 1004, jER 1009 (are commodity Name；Limited liability company, Mitsubishi Chemical).The concrete example of the commercially available product of bisphenol F type epoxy compound is jER 806, jER 4005P It (is trade name；Limited liability company, Mitsubishi Chemical).The concrete example of the commercially available product of diglycidyl ether type epoxy compound is spy Gram not (TECHMORE) VG3101L (trade name；Pu Lintaike (Printec) limited liability company)；EHPE3150 (trade name； Daicel (Daicel) limited liability company)；EPPN-501H, EPPN-502H (are trade name；The Japanese limited public affairs of chemical drug share Department)；And jER 1032H60 (trade name；Limited liability company, Mitsubishi Chemical).The commercially available product of glycidyl ester type epoxy compound Concrete example be that pellet receives Cauer (Denacol) EX-721 (trade name；The long rapids chemical conversion limited public affairs of (Nagase chemteX) share Department) and 1,2- cyclohexane dicarboxylic acid 2-glycidyl ester (trade name；Tokyo chemical conversion industry limited liability company).Biphenyl type epoxy The concrete example of the commercially available product of compound is jER YX4000, jER YX4000H, jER YL6121H (are trade name；Mitsubishi Learn limited liability company)；And NC-3000, NC-3000-L, NC-3000-H, NC-3100 (are trade name；Japanese chemical drug share Co., Ltd).The concrete example of the commercially available product of phenol novolak-type epoxy compound is EPPN-201 (trade name；Japanese chemical drug Limited liability company)；And jER 152, jER 154 (are trade name；Limited liability company, Mitsubishi Chemical) etc..Cresol novolac is clear The concrete example of the commercially available product of paint shaped epoxide is that EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1020 (are Trade name；NIPPON PHARMACEUTICAL CO., LTD) etc..The concrete example of the commercially available product of bisphenol A novolac type ring oxygen compound is jER 157S65, jER 157S70 (are trade name；Limited liability company, Mitsubishi Chemical).Ring type aliphatic epoxy compound it is commercially available The concrete example of product is that Sai Luo West Germany (Celloxide) 2021P, Sai Luo West Germany (Celloxide) 3000 (is trade name；Contest Fine jade (Daicel) limited liability company).The concrete example of the commercially available product of epoxide with siloxanes key knot position is 1,3- Bis- [2- (3,4- epoxycyclohexyl) ethyl] tetramethyl disiloxane (trade names；Prompt Leicester limited liability company (Gelest Incorporated)), TSL9906 (trade name；Japan figure new high-tech material (Momentive Performance advanced in years Materials Japan) Co., Ltd), examine special Olso (COATOSIL) MP200 (trade name；Japanese Mai Tugao green wood Expect (Momentive Performance Materials Japan) Co., Ltd), sky Po Sailang (Conpoceran) SQ506 (trade name；Waste river chemistry limited liability company), ES-1023 (trade name；Shin-Estu Chemical Co., Ltd).
Furthermore Te Kemo (TECHMORE) VG3101L (trade name；Pu Lintaike (Printec) limited liability company) be 2- [4- (2,3- glycidoxy) phenyl] -2- [4- [bis- [4- (2,3- glycidoxy) phenyl] ethyls of 1,1-] phenyl] propane With bis- [4- [1- [4- (2,3- glycidoxy) phenyl] -1- [4- [1- [4- (2,3- glycidoxy) the phenyl] -1- first of 1,3- Base ethyl] phenyl] ethyl] phenoxy group] -2- propyl alcohol mixture.EHPE3150 (trade name；Daicel (Daicel) share has Limit company) be bis- (the hydroxymethyl)-n-butyl alcohols of 2,2- 1,2- epoxy group -4- (2- oxiranyl) hexamethylene addition product.Match Luo Xide (Celloxide) 2021P (trade name；Daicel (Daicel) limited liability company) it is 3', 4'- epoxycyclohexyl first Base -3,4- epoxycyclohexane carboxylate.3000 (trade name of Sai Luo West Germany (Celloxide)；Daicel (Daicel) share is limited Company) it is 1- methyl -4- (2- methyl oxiranyl) -7- oxabicyclo [4.1.0] heptane.Examine special Olso (COATOSIL) MP200 (trade name；Japan's figure new high-tech material (Momentive Performance Materials Japan) Limited Liability advanced in years Company) it is using 3- glycidoxypropyltrimewasxysilane as the polymer of material composition.
Compound (B) with more than two epoxy groups can be used alone the compound, can also be used in mixed way two kinds More than.
1-2-2. has ratio of the compound (B) of more than two epoxy groups relative to polymer (A)
The total amount of the compound (B) with more than two epoxy groups in thermosetting composition of the invention relative to The ratio of 100 parts by weight of polymer (A) is 10 parts by weight~500 parts by weight.If the compound with more than two epoxy groups (B) ratio of total amount is the range, then flatness, heat resistance, chemical-resistant, the balance of substrate adhesion are good.Tool Total amount there are two the compound (B) of above epoxy group is preferably 50 parts by weight~300 parts by weight range, but adjusts and gather Close object (A), the molar ratio of epoxy curing agent determines the total amount.
1-3. solvent (C)
In thermosetting composition of the invention, it can be used solvent (C).Made in thermosetting composition of the invention Solvent (C) is preferably the solvent of soluble polymeric object (A) and the compound (B) with more than two epoxy groups.It is described The concrete example of solvent is ethyl acetate, butyl acetate, propyl acetate, butyl propionate, ethyl lactate, methoxy menthyl acetate, first Ethoxyacetic acid ethyl ester, methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, acetic acid -3- methoxybutyl, 3- oxygroup methyl propionate, 3- hydroxypropionate, 3- methoxy methyl propionate, 3- methoxypropionate, 3- ethoxy-propionic acid Methyl esters, 3- ethoxyl ethyl propionate, 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid propyl ester, 2- methoxy methyl propionate, 2- methoxyl group Ethyl propionate, 2- methoxy propyl propyl propionate, 2- ethoxypropanoate, 2- ethoxyl ethyl propionate, 2- hydroxy-2-methyl propionic acid Methyl esters, 2- hydroxy-2-methyl ethyl propionate, 2- methoxyl group -2 Methylpropionic acid methyl esters, 2- ethyoxyl -2 Methylpropionic acid ethyl ester, third Ketone acid methyl esters, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 2-Oxobutyric acid methyl esters, 2- oxygen For ethyl butyrate, 4- hydroxy-4-methyl-2-pentanone, 1,4- butanediol, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, third 2-ethoxyethanol acetic acid esters, propylene glycol monopropyl ether acetic acid esters, ethylene glycol monomethyl ether acetate, cyclohexanone, cyclopentanone, diethylene glycol Monomethyl ether, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether acetic acid esters, diethylene glycol mono butyl Ether, butyl carbitol acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether and diethylene glycol methyl ethyl ether.It is molten Agent can be one kind of these solvents, can also be the two or more mixtures of these solvents.
1-4. other compositions
In thermosetting composition of the invention, various additives can be added, with improve coating homogeneity, cementability, The transparency, flatness and chemical-resistant.Additive can mainly be enumerated: solvent；Anionic system, cationic system, nonionic system, fluorine Leveling agent/surfactant of system or silicon systems；The adhesions enhancer such as silane coupling agent；Hindered phenolic, amine system of being obstructed, phosphorus system, The antioxidants such as chalcogenide compound；Molecular weight regulator；Epoxy curing agent.
1-4-1. surfactant
In thermosetting composition of the invention, surfactant can also be added, to improve coating homogeneity.Surface is living The concrete example of property agent can be enumerated: Pohle not Lip river (Polyflow) No.75, Pohle not Lip river (Polyflow) No.90, Pohle not Lip river (Polyflow) No.95 (being trade name, chemistry limited liability company, common prosperity society), Di Sipabike (Disperbyk) -161, Di Sipabike (Disperbyk) -162, Di Sipabike (Disperbyk) -163, Di Sipabike (Disperbyk) - 164, Di Sipabike (Disperbyk) -166, Di Sipabike (Disperbyk) -170, Di Sipabike (Disperbyk) -180, Di Sipabike (Disperbyk) -181, Di Sipabike (Disperbyk) -182, BYK-300, BYK-306、BYK-310、BYK-320、BYK-330、BYK-342、BYK-346、BYK-361N、BYK-UV3500、BYK- UV3570 (being trade name, chemical (the BYK Chemie Japan) limited liability company of Japanese Bi Ke), KP-341, KP-368, KF-96-50CS, KF-50-100CS (being trade name, Shin-Estu Chemical Co., Ltd), Sha Fulong (Surflon)- S611 (trade name, AGC beautify clearly (AGC Seimi Chemical) limited liability company), Fu Jite (Ftergent) 222F, Fu Jite (Ftergent) 208G, Fu Jite (Ftergent) 251, Fu Jite (Ftergent) 710FL, Fu Jite (Ftergent) 710FM, Fu Jite (Ftergent) 710FS, Fu Jite (Ftergent) 601AD, Fu Jite (Ftergent) 650A, FTX-218 (being trade name, Ni Aosi (Neos) limited liability company), Mei Jiafa (Megafac) F-410, Mei Jiafa (Megafac) F-430, Mei Jiafa (Megafac) F-444, Mei Jiafa (Megafac) F-472SF, Mei Jiafa (Megafac) F- 475, Mei Jiafa (Megafac) F-477, Mei Jiafa (Megafac) F-552, Mei Jiafa (Megafac) F-553, Mei Jiafa (Megafac) F-554, Mei Jiafa (Megafac) F-555, Mei Jiafa (Megafac) F-556, Mei Jiafa (Megafac) F- 558, Mei Jiafa (Megafac) F-559, Mei Jiafa (Megafac) R-94, Mei Jiafa (Megafac) RS-75, Mei Jiafa (Megafac) RS-72-K, Mei Jiafa (Megafac) RS-76-NS, Mei Jiafa (Megafac) DS-21 (is trade name, enlightening love Raw (DIC) limited liability company), Digao village (TEGO Twin) 4000, Digao village (TEGO Twin) 4100, Digao not Lip river (TEGO Flow) 370, Digao Ge Laide (TEGO Glide) 440, Digao Ge Laide (TEGO Glide) 450, Digao ladd (TEGO Rad) 2200N (being trade name, Japan wins wound (Evonik Japan) limited liability company), fluoroalkyl benzene sulfonic acid It is salt, fl muoroalkyl's salt, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl glycine betaine, fluoroalkyl sulfonate, two sweet Oily four (fluoroalkyl polyoxyethylene ether), fluoroalkyl leptodactyline, fluoroalkyl sulfamate, ethylene nonyl phenyl ether, NONIN HS 240, polyoxyethylene alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene Tridecyl ether, polyoxyethylene cetyl base ether, polyoxyethylene stearyl base ether, polyoxyethylene laurate, polyoxyethylene oleate, Myrj 45, polyoxyethylene laural base amine, sorbitol anhydride laurate, sorbitol anhydride palmitate, sorbitol anhydride Stearate, sorbitan oleate, sorbitan carboxylic esters, polyoxyethylene sorbitol acid anhydride laurate, polyoxyethylene mountain Pears alcohol acid anhydride palmitate, polyoxyethylene sorbitol acid anhydride stearate, polyoxyethylene sorbitol acid anhydride oleate, polyoxyethylene naphthalene Ether, alkylbenzene sulfonate and alkyl diphenyl base ether disulfonate.Preferably use at least one in these surfactants Kind.
In these surfactants, if selected from BYK-306, BYK-342, BYK-346, KP-341, KP-368, Sha Fulong (Surflon)-S611, Fu Jite (Ftergent) 710FL, Fu Jite (Ftergent) 710FM, Fu Jite (Ftergent) 710FS, Fu Jite (Ftergent) 601AD, Fu Jite (Ftergent) 650A, Mei Jiafa (Megafac) F-477, Mei Jiafa (Megafac) F-556, Mei Jiafa (Megafac) F-559, Mei Jiafa (Megafac) RS-72-K, Mei Jiafa (Megafac) DS- 21, Digao collects (TEGO Twin) 4000, fluoroalkyl benzene sulfonate, fl muoroalkyl's salt, fluoroalkyl polyoxyethylene ether, fluoroalkyl At least one of sulfonate, fluoroalkyl leptodactyline and fluoroalkyl sulfamate, the then coating of thermosetting composition Uniformity is got higher, therefore preferably.
Relative to thermosetting total composition, the content of the surfactant in thermosetting composition of the invention is excellent It is selected as 0.01 weight of weight %~10 %.
1-4-2. coupling agent
For further increasing the viewpoint for the adhesion for being formed by cured film and substrate, thermosetting group of the invention Coupling agent can also also be contained by closing object.
As such coupling agent, such as the coupling agent of silane system, aluminium system or titanate esters system can be used.Specifically, can arrange It lifts: 3- glycidoxypropyl dimethylethoxysilane, 3- glycidoxypropyl diethoxy silane, 3- contracting Water glycerol oxygroup propyl trimethoxy silicane is (for example, trade name, Sa Laaisi (Sila-Ace) S510, prompt grace intelligence (JNC) share Co., Ltd), 2- (3,4- epoxycyclohexyl) ethyl trimethoxy silane is (for example, trade name, Sa Laaisi (Sila-Ace) S530, prompt grace intelligence (JNC) limited liability company), 3-mercaptopropyi trimethoxy silane is (for example, trade name；Sa Laaisi (Sila-Ace) S810, prompt grace intelligence (JNC) limited liability company), the copolymerization of 3- glycidoxypropyltrimewasxysilane Object is (for example, trade name, examines special Olso (COATOSIL) MP200, Japan figure new high-tech material (Momentive advanced in years Performance Materials Japan) Co., Ltd) etc. silane series coupling agents；Acetyl alkoxy aluminum-diisopropoxide Etc. aluminium system coupling agents；And the titanate esters system coupling agent such as bis- (dioctyl phosphito ester) titanate esters of tetra isopropyl.
In these coupling agents, the effect of the raising adhesion of 3- glycidoxypropyltrimewasxysilane is big, therefore It is preferred that.
It is total relative to thermosetting composition for the aspect that adhesion with regard to being formed by cured film and substrate improves Amount, the content of coupling agent is preferably 0.01 weight % or more and 10 weight % or less.
1-4-3. antioxidant
For the viewpoint of xanthochromia when improving the transparency, preventing cured film from exposing at high temperature, thermmohardening of the invention Property composition can also also contain antioxidant.
In thermosetting composition of the invention, hindered phenolic, amine system of being obstructed, phosphorus system, chalcogenide compound can also be added Equal antioxidants.Wherein, for the viewpoint of weatherability, preferred hindered phenolic.It as concrete example, can enumerate: Yi Lu Jia Nuosi (Irganox) 1010, Yi Lu Jia Nuosi (Irganox) 1010FF, Yi Lu Jia Nuosi (Irganox) 1035, Yi Lu Jia Nuosi (Irganox) 1035FF, Yi Lu Jia Nuosi (Irganox) 1076, Yi Lu Jia Nuosi (Irganox) 1076FD, Yi Lu Jia Nuosi (Irganox) 1098, Yi Lu Jia Nuosi (Irganox) 1135, Yi Lu Jia Nuosi (Irganox) 1330, Yi Lu Jia Nuosi (Irganox) 1726, Yi Lu Jia Nuosi (Irganox) 1425WL, Yi Lu Jia Nuosi (Irganox) 1520L, Yi Lu Jia Nuosi (Irganox) 245, Yi Lu Jia Nuosi (Irganox) 245FF, Yi Lu Jia Nuosi (Irganox) 259, Yi Lu Jia Nuosi (Irganox) 3114, Yi Lu Jia Nuosi (Irganox) 565, Yi Lu Jia Nuosi (Irganox) 565DD (be trade name, Japan BASF (BASF Japan) limited liability company)；Ai Di Coase tower wave (ADK STAB) AO-20, Ai Di Coase tower wave (ADK STAB) AO-30, Ai Di Coase tower wave (ADK STAB) AO-50, Ai Di Coase tower wave (ADK STAB) AO-60, Ai Di Coase tower Wave (ADK STAB) AO-80 (being trade name, Ai Dike (ADEKA) limited liability company).Wherein, more preferably Yi Lujia promise This (Irganox) 1010, Ai Di Coase tower wave (ADK STAB) AO-60.
Relative to thermosetting total composition, adds 0.1 parts by weight~10 parts by weight antioxidant and use.
1-4-4. epoxy curing agent
In order to improve flatness, chemical-resistant, thermosetting composition of the invention can also also contain epoxy curing agent. As epoxy curing agent, there are acid anhydrides system curing agent, amine system curing agent, phenol system curing agent, imidazoles system curing agent, pyrazoles system are hard Agent, triazole system curing agent, catalyst type curing agent and sulfonium salt (sulfonium salt), benzothiazolium salt, ammonium salt, phosphonium salt Deng thermonasty acid producing agent etc., it is avoided that for the viewpoint of the heat resistance of the coloring and cured film of cured film, preferably acid anhydrides It is curing agent or imidazoles system curing agent or and with acid anhydrides system curing agent and imidazoles system curing agent.
The concrete example of acid anhydrides system curing agent be maleic anhydride, tetrabydrophthalic anhydride, hexahydrophthalic anhydride, The aliphatic dicarboxylic acids acid anhydrides such as methylhexahydrophthalic anhydride, hexahydro trimellitic anhydride；Phthalic anhydride, trimellitic anhydride etc. Aromatic polycarboxylic acid acid anhydride；And styrene-maleic anhydride copolymer.In these acid anhydrides system curing agents, preferably heat resistance with To the good trimellitic anhydride of deliquescent balance and hexahydro trimellitic anhydride of solvent.
The concrete example of imidazoles system curing agent is 2- undecyl imidazole, 2- heptadecyl imidazole, 2- phenylimidazole, 2- Phenyl -4-methylimidazole, 2,3- dihydro -1H- pyrrolo- [1,2-a] benzimidazole, 1- cyano ethyl -2- undecyl imidazole Trimellitic acid salt.In these imidazoles system curing agents, preferably hardenability and 2- ten one good to the deliquescent balance of solvent Alkyl imidazole.
Using epoxy curing agent, epoxy curing agent is relative to the compound with more than two epoxy groups (B) ratio of 100 parts by weight is 0.1 parts by weight~60 parts by weight.About epoxy curing agent be acid anhydrides system curing agent when addition Amount, more specifically, preferably with relative to epoxy group and in epoxy curing agent acid anhydride or carboxyl become 0.1 times of equivalent The mode of~1.5 times of equivalents is added.At this point, acid anhydride is calculated with divalent.If to become 0.15 times of equivalent~0.8 The mode of times equivalent adds acid anhydride or carboxyl, then chemical-resistant further increases, therefore more preferably.
1-4-5. ultraviolet absorbing agent
For further increasing the viewpoint for the degradation inhibiting ability for being formed by hyaline membrane, thermosetting group of the invention Ultraviolet absorbing agent can also be contained by closing object.
The concrete example of ultraviolet absorbing agent is refined (TINUVIN) P of Supreme Being slave, refined (TINUVIN) 120 of Supreme Being slave, Supreme Being slave are refined (TINUVIN) 144, refined (TINUVIN) 213 of Supreme Being slave, refined (TINUVIN) 234 of Supreme Being slave, refined (TINUVIN) 326 of Supreme Being slave, Supreme Being slave are refined (TINUVIN) 571, Supreme Being slave refined (TINUVIN) 765 (be trade name, the limited public affairs of Japanese BASF (BASF Japan) share Department).
Relative to thermosetting total composition, adds 0.01 parts by weight~10 parts by weight ultraviolet absorbing agent and make With.
The anti-flocculating agent of 1-4-6.
For merging solid component with solvent, preventing the viewpoint of cohesion, thermosetting composition of the invention Anti- flocculating agent can be contained.
The concrete example of anti-flocculating agent is Di Sipabike (Disperbyk) -145, Di Sipabike (Disperbyk) - 161, Di Sipabike (Disperbyk) -162, Di Sipabike (Disperbyk) -163, Di Sipabike (Disperbyk) -164, Di Sipabike (Disperbyk) -182, Di Sipabike (Disperbyk) -184, Di Sipabi Gram (Disperbyk) -185, Di Sipabike (Disperbyk) -2163, Di Sipabike (Disperbyk) -2164, BYK- 220S, Di Sipabike (Disperbyk) -191, Di Sipabike (Disperbyk) -199, Di Sipabike (Disperbyk) -2015 (be trade name；Chemical (BYK Chemie Japan) limited liability company of Japanese Bi Ke)；FTX- 218, Fu Jite (Ftergent) 710FM, Fu Jite (Ftergent) 710FS (is trade name, Ni Aosi (Neos) share has Limit company)；Not long-range navigation (Flowlen) G-600, Fu Luolun (Flowlen) G-700 (is trade name, common prosperity society chemistry share has Limit company).
Relative to thermosetting total composition, adds the anti-flocculating agent of 0.01 parts by weight~10 parts by weight and use.
1-4-7. thermal cross-linking agent
Just further increase heat resistance, chemical-resistant, film inner evenness, flexibility, flexibility, the viewpoint of elasticity and Speech, thermosetting composition of the invention can also contain thermal cross-linking agent.
The concrete example of thermal cross-linking agent be Ni Kalake (Nikalac) MW-30HM, Ni Kalake (Nikalac) MW-100LM, Ni Kalake (Nikalac) MX-270, Ni Kalake (Nikalac) MX-280, Ni Kalake (Nikalac) MX-290, Buddhist nun's card Clarke (Nikalac) MW-390, Ni Kalake (Nikalac) MW-750LM (be trade name, three and chemical (stock)).
Relative to thermosetting total composition, adds 0.1 parts by weight~10 parts by weight thermal cross-linking agent and use.
The preservation of 1-5. thermosetting composition
If thermosetting composition of the invention saves in the range of -30 DEG C~25 DEG C, composition through Shi Wending Property become good.If storage temperature is -20 DEG C~10 DEG C, precipitate is also not present and more preferable.
2. the cured film formed by thermosetting composition
About thermosetting composition of the invention, by polymer (A), the compound with more than two epoxy groups (B) and solvent (C) mixes, and according to target property, can optionally select addition epoxy curing agent, surfactant, idol in turn Join agent, antioxidant and other additives.
If the thermosetting composition prepared as described above (in the case where solvent-free solid state, is dissolved in After in solvent) it is coated on matrix surface, solvent is removed for example, by heating etc., then can form film.To matrix table The coating of the thermosetting composition in face can utilize the conventionally known sides such as spin-coating method, rolling method, infusion process and slot coated method Method forms film.Then, the film is temporarily calcined using heating plate or baking oven etc..Temporary calcination condition regards the kind of each ingredient Class and allotment ratio and difference is 5 minutes~15 minutes if using baking oven usually at 70 DEG C~150 DEG C, if using heating Plate is then 1 minute~5 minutes.Thereafter, it is formally calcined to harden film.Formal calcination condition regards the kind of each ingredient Class and allotment ratio and difference are 30 points if using baking oven usually at 180 DEG C~250 DEG C, preferably 200 DEG C~250 DEG C Clock~90 minute are 5 minutes~30 minutes if using heating plate, can obtain cured film and being heated.
The cured film obtained in this way when heated, polymer (A) with more than two epoxy groups chemical combination Object (B) reacts and forms three-dimensional network, therefore very tough, and the transparency, heat resistance, chemical-resistant, flatness, adhesion It is excellent.In addition, being also contemplated that light resistance, resistant sputtering, scratch resistance, coating are excellent for identical reason.Therefore, originally If the protective film that the cured film of invention is used as colored filter effectively the colored filter can be used to manufacture liquid crystal Display element or solid-state imager.In addition, other than the protective film of colored filter, if cured film of the invention is used as The transparent insulating film that is formed between thin film transistor (TFT) (Thin Film Transistor, TFT) and transparent electrode is formed in Transparent insulating film between prescribed electrode and alignment films, then also effectively.In turn, even if cured film of the invention is used as light emitting diode The protective film of (Light Emitting Diode, LED) illuminator, also effectively.
[embodiment]
Then, the present invention is specifically described by synthesis example, Examples and Comparative Examples, but the present invention is not by these Any restriction of embodiment.
For every kind of ingredient, compound used in synthesis example, Examples and Comparative Examples is recorded.
The synthesis of [synthesis example 1] polymer (A1) solution
In the four-hole boiling flask with blender, diethylene glycol methyl ethyl ether (EDM), 4,4'- are packed into following weight Oxygroup diphthalic anhydrides (ODPA), 2- ethylaminoethanol (AE), the heating stirring 3 under drying nitrogen air-flow and at 150 DEG C Hour, to obtain polymer solution.
EDM 10.01g
ODPA 8.360g
AE 1.646g
Thereafter, solution is cooled to room temperature, to obtain 50 weight % solution of the polymer (A1) of pale yellow transparent.It is right A part of solution is sampled, and measures weight average molecular weight using gpc analysis (polystyrene standard).As a result, being obtained The weight average molecular weight of the polymer (A1) obtained is 3,000.
The synthesis of [synthesis example 2] polymer (A2)
As follows, by 3- methoxy methyl propionate (MMP uses the 70% of loading total amount), N- cyclohexyl horse Carry out acid imide, maleic anhydride is fitted into the four-hole boiling flask with blender and cooler, under stream of nitrogen gas and at 80 DEG C Heating stirring.Then, by the mixing of radical initiator V-65 (and Wako Pure Chemical Industries Manufacturing) and α-methylstyrenedimer The MMP solution (using being fitted into the 30% of total amount) of object is fitted into addition funnel, is lasted 1 hour and is carried out dropwise addition polymerization.Thereafter, exist Heating stirring 2 hours at 80 DEG C, thus the base co-polymer that gains freedom.
After being cooled to room temperature, the 2- ethylaminoethanol (AE) of 1.102g, heating stirring 3 hours at 150 DEG C, to obtain are added Obtain polymer (A2) solution.A part of solution is sampled, measures weight average using gpc analysis (polystyrene standard) Molecular weight.As a result, the weight average molecular weight of polymer (A2) obtained is 16,100.
The synthesis of [3~synthesis example of synthesis example 5] polymer (A3)~polymer (A5) solution
According to synthesis example 1, the method for synthesis example 2, listed in Table 1 temperature, time and ratio (unit: g) make it is each at Divide reaction, to obtain polymer solution.
The synthesis of [comparing synthesis example 1] polyesteramide acid (R1) solution
Listed in Table 1 temperature, time and ratio react polyesteramide acid, so that it is molten to obtain polyesteramide sour (R1) Liquid.Wherein, the reaction of first stage is to carry out 3 hours at 150 DEG C with reacting for ODPA and 1,4-butanediol (BD), thereafter, The reaction reacted as second stage in 1 hour is carried out at 120 DEG C with 3,3'- diamino diphenyl sulfone.
Table 1
The unit of charge weight: gram
Recorded in table 1 with abbreviation, synthesis example and to compare compound used in synthesis example respectively as described below.
ODPA:4,4'- oxygroup diphthalic anhydrides
CHMI:N- N-cyclohexylmaleimide
IN: indenes
MAH: maleic anhydride
AE:2- ethylaminoethanol
AEE:2- (2- amino ethoxy) ethyl alcohol
BD:1,4- butanediol
MDDS:3,3'- diamino diphenyl sulfone
V-65:2,2'- azo is bis- (2,4- methyl pentane nitrile)；It is manufactured with Wako Pure Chemical Industries (stock)
α-MSD: α-methylstyrenedimer
EDM: diethylene glycol methyl ethyl ether
MMP:3- methoxy methyl propionate
[embodiment 1]
With the ratio (parts by weight) recorded in table 2 by 50 weight % solution of polymer obtained in synthesis example 1 (A1), VG3101L as trifunctional epoxide, the trimellitic anhydride as curing agent (TMA), as silane coupling agent S510, as Ai Di Coase tower wave (ADK STAB) AO-60 of antioxidant, as the F-556 of surfactant and as dilute 3- methoxy methyl propionate (MMP) mixed dissolution for releasing solvent is filtered using membrane filter (0.2 μm of aperture), thus Obtain thermosetting composition.
[2~embodiment of embodiment 5 and comparative example 1]
According to the method for embodiment 1, with the ratio (parts by weight) recorded in table 2 by each ingredient mixed dissolution, to obtain Thermosetting composition.
Table 2
Unit: parts by weight (except surfactant)
Using each thermosetting composition obtained, and evaluate using the method for following record heat resistance, flat Property, substrate adhesion.The evaluation result of the cured film of 1~embodiment of embodiment 5 is summarized and is recorded in table 3.In addition, about than Compared with example 1, the heat resistance, planarization property, substrate adhesion of the thermosetting composition containing polyesteramide acid are evaluated.It will Evaluation result is recorded in together in table 3.
[evaluation method of heat resistance]
It lasts 10 seconds with 650rpm thermosetting composition obtained is spun on glass substrate, in 80 DEG C of heating Prebake conditions 2 minutes on plate.Then, it is heat-treated 30 minutes with 230 DEG C in an oven, to obtain the glass base for having cured film Plate.For the glass substrate obtained with cured film, scale/surface roughness/fine shape measurement device (commodity are used Name；P-17, KLA Ke Lei (KLA TENCOR) limited liability company) film thickness is measured, it is adjusted in such a way that film thickness becomes 1.5 μm Spincoating conditions.Thereafter, the glass substrate for coming with cured film, which is cut, takes cured film, utilizes thermogravimetric/differential thermal measurement device (Thermogravimetric-Differential Thermal Analysis, TG-DTA) carries out protecting for 60 minutes at 230 DEG C Measurement is held, is set as zero for 0.5% or less situation is reduced to from weight when reaching 230 DEG C, the situation more than it is set as ×, And it is shown together with measured value.
[evaluation method of flatness]
Scale/surface roughness/fine shape measurement device (trade name is being used in advance；P-17, KLA Ke Lei (KLA TENCOR) limited liability company) determine concave-convex base plate (100 μm of the line, 50 μ of space comprising resist pattern of surface scale M, 1 μm of film thickness of pattern substrate) on, the thermosetting composition obtained of spin coating in 10 seconds is lasted with 650rpm, in 80 DEG C add Prebake conditions 2 minutes on hot plate.Then, it is heat-treated 30 minutes with 230 DEG C in an oven, so that the average film thickness for obtaining protective film is 1.5 μm of the colored filter substrate with cured film.Thereafter, the colored filter substrate to obtained with cured film is surveyed Determine surface scale.According to the colored filter substrate of no cured film and the surface scale of the colored filter substrate with cured film Maximum value (being slightly denoted as " maximum scale " below), and calculate flat rate using following calculating formulas, show the result in table 3 In.About flatness as a result, be evaluated as ◎ for 100%~80%, it is evaluated as zero by 79%~60%, less than 60% is evaluated For ×.
Flat rate (%)=((the maximum scale of concave-convex base plate of the maximum scale-of concave-convex base plate with cured film)/it is recessed The maximum scale of convex substrate) × 100
[evaluation method of adhesion]
With 650rpm last 10 seconds by thermosetting composition obtained be spun on concave-convex base plate (line: 100 μm, space: 50 μm, film thickness: 1.0 μm) on, prebake conditions 2 minutes in 80 DEG C of heating plate.Then, 30 points are heat-treated with 230 DEG C in an oven Clock, to obtain the concave-convex base plate for having cured film.It is made in the same manner as the concave-convex base plate obtained with cured film Obtained by have cured film both glass substrates, carry out cross-cut test (Japanese Industrial Standards (Japanese Industrial Standards, JIS) K 5400, stripping tape: using 3M manufacture No.361), according to it is below classification 0~ Classification 5 is evaluated, and classification 0~classification 1 is set as zero, and classification 2~classification 3 is set as △, classification 4~classification 5 is set as ×。
The edge of < 0 > ... cutting of classification is completely smooth, and without peeling in the grid of any grid.
The small peeling of the film of the intersection of < 1 > ... cutting of classification.It is affected in cross-cut part Part will not clearly exceed 5%.
2 > ... film of < classification is peeled off along the edge of cutting and/or in intersection.In cross-cut part, by shadow Loud part clearly more than 5% but not exceeds 15%.
3 > ... films of < classification along the edge of cutting and part or entire surface generate big peeling and/or grid Peel off to mass part part or entire surface.In cross-cut part, affected part is clearly more than 15% but not super Out 35%.
4 > ... films of < classification along the edge of cutting and part or entire surface generate big peeling and/or many places Peel off to grid part or entire surface.In cross-cut part, affected part will not clearly exceed 35%.
Even if < classify 5 > ... be classification 4, the peeling degree that can not also classify any one.
[transparent evaluation method]
It lasts 10 seconds with 650rpm thermosetting composition obtained is spun on glass substrate, in 80 DEG C of heating Prebake conditions 2 minutes on plate.Then, it is heat-treated 30 minutes with 230 DEG C in an oven, so that obtaining film thickness is 1.5 μm with hard Change the glass substrate of film.For the glass substrate obtained with cured film, UV, visible light near infrared spectrometer is utilized (trade name；V-670, light splitting limited liability company, Japan) light transmittance under 400nm to measure cured film.In the situation Under, glass substrate is used only as reference, and the light transmittance for calculating cured film monomer (in said case, does not consider by multiple The caused interference of reflection).The situation that light transmittance is 98% or more is evaluated as the transparency zero, will transmit through the feelings of rate less than 95% Condition be evaluated as the transparency ×, △ will be evaluated as between it.
Clearly learnt according to result shown in table 3: the thermosetting composition of 1~embodiment of embodiment 5 meet heat resistance, Flatness, adhesion, the transparency.On the other hand, in comparative example 1, all characteristics are unable to satisfy.
Table 3
[industrial availability]
Heat resistance, flatness, substrate adhesion by the cured film of thermosetting composition acquisition of the invention is good, And the protective film of the various optical materials etc. such as can be used as colored filter, LED light-emitting component and light receiving element and it is formed in TFT Insulating film between transparent electrode and between transparent electrode and alignment films.

Claims (6)

1. a kind of thermosetting composition, compound (B) it includes polymer (A), with more than two epoxy groups and molten Agent (C), the polymer (A) be from more than two anhydride groups compound (a) and following formula (1) represented by There is the product of the compound (b) of amino and hydroxyl in same intramolecular:
In formula (1), R1For divalent organic base.
2. thermosetting composition according to claim 1, wherein the compound with more than two anhydride groups (a) for selected from copolymerization composition in comprising aromatic acid dianhydride, aliphatic acid dianhydride and maleic anhydride polymer at least It is a kind of.
3. thermosetting composition according to claim 1, wherein the R of the compound (b)1For can branch carbon number 1~ Bilvalent radical represented by 10 alkylidene or following formula (2):
-CH2CH2(OCH2CH2)m- (2)
In formula (2), m be 1~9 integer.
4. thermosetting composition according to claim 1, wherein the compound with more than two epoxy groups It (B) is the compound with aromatic rings.
5. a kind of cured film is formed by thermosetting composition according to any one of claims 1 to 4.
6. a kind of colored filter, with cured film as claimed in claim 5 as transparent protective film.
CN201910231485.8A 2018-03-29 2019-03-26 Thermosetting composition, cured film and colored filter Pending CN110317534A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018063969A JP6947102B2 (en) 2018-03-29 2018-03-29 Thermosetting composition
JP2018-063969 2018-03-29

Publications (1)

Publication Number Publication Date
CN110317534A true CN110317534A (en) 2019-10-11

Family

ID=68112910

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910231485.8A Pending CN110317534A (en) 2018-03-29 2019-03-26 Thermosetting composition, cured film and colored filter

Country Status (4)

Country Link
JP (1) JP6947102B2 (en)
KR (1) KR20190114796A (en)
CN (1) CN110317534A (en)
TW (1) TWI797295B (en)

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62163016A (en) * 1986-01-14 1987-07-18 Japan Synthetic Rubber Co Ltd Color filter
JPS62242918A (en) * 1986-04-15 1987-10-23 Kyodo Printing Co Ltd Color filter
JPS63131103A (en) * 1986-11-20 1988-06-03 Toppan Printing Co Ltd Color filter
JPH07331178A (en) * 1994-06-14 1995-12-19 Toray Ind Inc Coating composition and its production
JPH0850289A (en) * 1994-06-01 1996-02-20 Sumitomo Chem Co Ltd Hardening type resin composition for overcoating for a color filter
CN1281478A (en) * 1997-10-01 2001-01-24 Dsm有限公司 Condensation polymer containing hydroxyalkylamide groups
JP2008156546A (en) * 2006-12-26 2008-07-10 Chisso Corp Thermosetting resin composition and cured film
CN102070775A (en) * 2010-11-16 2011-05-25 北方涂料工业研究设计院 Method for preparing multi-hydroxyl group-containing hyperbranched polyester resin
CN102165338A (en) * 2008-09-30 2011-08-24 大日本印刷株式会社 Inkjet ink composition for color filter, color filter, method of producing color filter, and liquid crystal display
JP2012025894A (en) * 2010-07-27 2012-02-09 Jnc Corp Thermosetting composition and its application
CN102372826A (en) * 2010-08-12 2012-03-14 株式会社Lg化学 Thermally curable resin composition for protective film
US20120183749A1 (en) * 2009-07-16 2012-07-19 Franciscus Johannes Marie Derks Resins and coating compositions
JP2013253263A (en) * 2007-10-19 2013-12-19 Nissan Chem Ind Ltd Polyester composition for production of thermally cured film
CN104974574A (en) * 2015-06-30 2015-10-14 苏州洋杰电子有限公司 Insulating paint for electronic component and preparation method thereof
CN105086316A (en) * 2014-05-15 2015-11-25 捷恩智株式会社 Thermosetting compositions, harden film, color filter, liquid crystal displaying element, solid camera shooting element and light emitting diode illuminant
US20160211142A1 (en) * 2015-01-16 2016-07-21 Jung-Hoon Kim Hard mask composition for spin-coating
CN106494021A (en) * 2016-09-30 2017-03-15 临安金奥科技有限公司 A kind of PET overlay films aluminium sheet and preparation method thereof
CN107207702A (en) * 2015-01-23 2017-09-26 捷恩智株式会社 Compositions of thermosetting resin, cured film, substrate and electronic component with cured film

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0774262B2 (en) * 1992-02-24 1995-08-09 三洋化成工業株式会社 Method for producing organic solvent suspension of cured epoxy resin, method for producing fine powder and suspension
JP5240125B2 (en) * 2009-08-28 2013-07-17 Ｊｎｃ株式会社 Thermosetting polymer composition

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62163016A (en) * 1986-01-14 1987-07-18 Japan Synthetic Rubber Co Ltd Color filter
JPS62242918A (en) * 1986-04-15 1987-10-23 Kyodo Printing Co Ltd Color filter
JPS63131103A (en) * 1986-11-20 1988-06-03 Toppan Printing Co Ltd Color filter
JPH0850289A (en) * 1994-06-01 1996-02-20 Sumitomo Chem Co Ltd Hardening type resin composition for overcoating for a color filter
JPH07331178A (en) * 1994-06-14 1995-12-19 Toray Ind Inc Coating composition and its production
CN1281478A (en) * 1997-10-01 2001-01-24 Dsm有限公司 Condensation polymer containing hydroxyalkylamide groups
JP2008156546A (en) * 2006-12-26 2008-07-10 Chisso Corp Thermosetting resin composition and cured film
JP2013253263A (en) * 2007-10-19 2013-12-19 Nissan Chem Ind Ltd Polyester composition for production of thermally cured film
CN102165338A (en) * 2008-09-30 2011-08-24 大日本印刷株式会社 Inkjet ink composition for color filter, color filter, method of producing color filter, and liquid crystal display
US20120183749A1 (en) * 2009-07-16 2012-07-19 Franciscus Johannes Marie Derks Resins and coating compositions
JP2012025894A (en) * 2010-07-27 2012-02-09 Jnc Corp Thermosetting composition and its application
CN102372826A (en) * 2010-08-12 2012-03-14 株式会社Lg化学 Thermally curable resin composition for protective film
CN102070775A (en) * 2010-11-16 2011-05-25 北方涂料工业研究设计院 Method for preparing multi-hydroxyl group-containing hyperbranched polyester resin
CN105086316A (en) * 2014-05-15 2015-11-25 捷恩智株式会社 Thermosetting compositions, harden film, color filter, liquid crystal displaying element, solid camera shooting element and light emitting diode illuminant
US20160211142A1 (en) * 2015-01-16 2016-07-21 Jung-Hoon Kim Hard mask composition for spin-coating
CN107207702A (en) * 2015-01-23 2017-09-26 捷恩智株式会社 Compositions of thermosetting resin, cured film, substrate and electronic component with cured film
CN104974574A (en) * 2015-06-30 2015-10-14 苏州洋杰电子有限公司 Insulating paint for electronic component and preparation method thereof
CN106494021A (en) * 2016-09-30 2017-03-15 临安金奥科技有限公司 A kind of PET overlay films aluminium sheet and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
艾永平等: "一种新型不饱和聚酯酰胺树脂的合成与表征", 《中山大学学报（自然科学版）》 *

Also Published As

Publication number Publication date
TWI797295B (en) 2023-04-01
KR20190114796A (en) 2019-10-10
JP6947102B2 (en) 2021-10-13
TW201942182A (en) 2019-11-01
JP2019172864A (en) 2019-10-10

Similar Documents

Publication Publication Date Title
CN104098756B (en) Thermoset composition, cured film and the electronic component with this cured film
KR20160038797A (en) Photosensitive resin composition for touch panel, cured film using the same, and touch panel including such cured film as a component
CN105607419A (en) Photosensitive composition and use thereof
CN107629678A (en) Thermosetting composition, cured film, colored filter, liquid crystal display cells and touch panel device
CN106610565A (en) Photosensitive composition and application thereof
JP3447768B2 (en) Thermosetting resin composition, cured product thereof and color filter material
CN105954972A (en) A photosensitive composition, a cured membrane, a color filter, a display element, a solid shooting element, a touch screen and an LED illuminant body
CN106554618A (en) Thermosetting compositionss and application thereof
CN107608178A (en) Photosensitive composite and cured film
CN107778485A (en) Polyesteramide acid and the photosensitive composite containing it
CN110317534A (en) Thermosetting composition, cured film and colored filter
CN107722685A (en) Thermosetting composition, cured film and colored filter
TWI782068B (en) Thermosetting compositions, cured film, and color filter
TWI774872B (en) Thermosetting composition, cured film and color filter
CN108628097A (en) Photosensitive composite, cured film, colored filter, display element, solid-state imager and LED illuminant heart
CN110373080B (en) Thermosetting composition, cured film and color filter
CN107589632A (en) Photosensitive composite and cured film
CN109401605A (en) Thermosetting composition, cured film and colored filter
TWI809170B (en) Thermosetting compositions, cured film, and color filter
TWI809178B (en) Thermosetting compositions, cured film, and color filter
TWI813756B (en) Thermosetting compositions, cured film, and color filter
CN108342044A (en) Photosensitive composite and application thereof
CN108693706A (en) Photosensitive composite and its application
KR20230154052A (en) Composition for forming a peeling layer and a peeling layer
CN116917399A (en) Composition for forming release layer and release layer

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination