WO2005073310A1 - Composition de résine, méthode de sa production et du film de résine - Google Patents

Composition de résine, méthode de sa production et du film de résine

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Publication number
WO2005073310A1
WO2005073310A1 PCT/JP2005/001212 JP2005001212W WO2005073310A1 WO 2005073310 A1 WO2005073310 A1 WO 2005073310A1 JP 2005001212 W JP2005001212 W JP 2005001212W WO 2005073310 A1 WO2005073310 A1 WO 2005073310A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
resin
resin composition
film
solvent
Prior art date
Application number
PCT/JP2005/001212
Other languages
English (en)
Japanese (ja)
Inventor
Hironori Omori
Original Assignee
Zeon Corporation
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 Zeon Corporation filed Critical Zeon Corporation
Priority to KR1020067015333A priority Critical patent/KR101220604B1/ko
Priority to JP2005517514A priority patent/JP4997766B2/ja
Priority to CN200580003684XA priority patent/CN1914271B/zh
Publication of WO2005073310A1 publication Critical patent/WO2005073310A1/fr

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Classifications

    • 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
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/06—Sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a resin composition capable of forming a resin film having both excellent transparency and in-plane thickness uniformity, a method for producing the same, and a resin film.
  • Organic electoluminescence is a type of display element such as an element or a liquid crystal display element, an integrated circuit element, a solid-state image sensor, a color filter, or a black matrix.
  • Components include a protective film to prevent their deterioration and damage, a sealing film to protect the contents, a flattening film to flatten the element surface and wiring, an electrical insulating film to keep electrical insulation, Various functional resin films such as an interlayer insulating film for insulating between wirings arranged in layers are provided.
  • these resin films may be required to have not only low dielectric properties but also transparency.
  • Examples of a material for forming a transparent resin film include a resin composition containing an alicyclic olefin-based addition copolymer having a reactive silyl group having a specific structure. It is known that when a metal oxide is added to a product, a crosslinked structure is formed to give a transparent resin film having excellent dimensional stability and the like (JP-A-2003-160620).
  • Japanese Patent Application Laid-Open No. 11-327125 discloses that the addition of inorganic fine particles such as colloidal silica to a photosensitive resin composition improves oxygen plasma resistance, heat resistance, dry etching resistance, and the like of the obtained resin film. It has been reported.
  • Japanese Patent Application Laid-Open No. 2003-156838 describes that a resin film having excellent coating film uniformity and storage stability can be obtained by adding a certain glycol-based solvent to an alicyclic resin. ing.
  • the alicyclic resin disclosed herein is capable of forming a transparent electric insulating film.
  • the present inventors have intensively studied to obtain a resin composition that can form a resin film that is transparent and has uniform in-plane film thickness.
  • a resin composition capable of forming a film can be obtained, and have completed the present invention.
  • carboxyl group, dicarboxylic anhydride group, hydroxyl group and imide group characterized in that it contains an alicyclic olefin resin having at least one member selected from the group consisting of in the molecule, inorganic fine particles, and a solvent.
  • Resin composition characterized in that it contains an alicyclic olefin resin having at least one member selected from the group consisting of in the molecule, inorganic fine particles, and a solvent.
  • the solvent contains at least 500 parts by weight of a solvent in which the solubility of the alicyclic olefin resin at 23 ° C. is 20% by weight or more based on 100 parts by weight of the alicyclic olefin resin.
  • the alicyclic resin is represented by the formula (I)
  • R 1 — R 4 are each independently a hydrogen atom or a formula: X n _R (X is a divalent group, n is 0 or 1, R is C 17 alkyl group which may have a substituent, C 3-8 cycloalkyl group which may have a substituent, aromatic group, carboxy group, dicarboxylic anhydride group , A hydroxy group, or an imide group), one or more of R 1 R 4 is a group represented by the formula: -X-R a (wherein X and n have the same meanings as described above) And Ra is a carboxyl group, a dicarboxylic anhydride group, a hydroxyl group, or an imide group. m is an integer of 0 2.
  • the resin composition according to (1) which is a resin having a repeating unit represented by the following formula:
  • the resin composition according to (1) further comprising a step of mixing a resin solution containing the alicyclic resin and a solvent with an inorganic fine particle dispersion containing the inorganic fine particles and a dispersion medium.
  • the dispersion medium is selected from the group consisting of glycol ether acetate compounds, glycol diether compounds, glycol monoether conjugates and amide compounds.
  • the resin composition of the present invention comprises an alicyclic resin having at least one selected from the group consisting of a carboxyl group, a dicarboxylic anhydride group, a hydroxy group and an imide group in a molecule, inorganic fine particles, and a solvent. It is characterized by containing.
  • the alicyclic olefin resin used in the present invention has a structural unit derived from a polymerizable monomer having an alicyclic structure and a carbon-carbon double bond (hereinafter, referred to as an “alicyclic olefin monomer”). It is a polymer.
  • the alicyclic structure of the alicyclic olefin monomer may be monocyclic or polycyclic (condensed polycyclic, bridged ring, combination of these, etc.). From the viewpoint of the mechanical strength and heat resistance of the resin film, a polycyclic ring is preferred.
  • the number of carbon atoms constituting the alicyclic structure is not particularly limited, but is usually 430, preferably 520, more preferably 515. When the number of carbon atoms is in such a range, various characteristics such as heat resistance and patternability of the resin film are highly balanced and suitable.
  • the proportion of the structural unit derived from the alicyclic olefin monomer in the alicyclic olefin resin is appropriately selected according to the purpose of use, but is usually from 30 to 100% by weight, preferably from 50 to 100% by weight. Preferably it is 70-100% by weight. If the proportion of the structural unit derived from the alicyclic olefin monomer is too small, the heat resistance of the resin film is poor, which is not preferable.
  • the alicyclic olefin resin used in the present invention includes a group consisting of a carboxyl group (hydroxycarbonyl group), a dicarboxylic anhydride group (carbonyloxycarbonyl group), a hydroxyl group, and an imide group in the molecule.
  • a carboxyl group hydroxycarbonyl group
  • a dicarboxylic anhydride group carbonyloxycarbonyl group
  • a hydroxyl group hydroxyl group
  • imide group in the molecule.
  • the specific polar group may be directly bonded to a carbon atom constituting the alicyclic structure which is the main chain of the resin, or may be a group containing the specific polar group which is bonded to a carbon atom constituting the alicyclic structure. It may be. In the latter case, the specific polar group is bonded to a carbon atom constituting the alicyclic structure via a divalent organic group such as an alkylene group.
  • Examples of the group containing a specific polar group include a group containing a carboxyl group, a group containing a dicarboxylic anhydride group, a group containing a hydroxyl group, and a group containing an imide group.
  • Examples of the group containing a carboxyl group include a hydroxycarbonylalkyl group and a hydroxycarboylphenyl group.
  • the group containing a dicarboxylic anhydride group is represented by an alkyleneoxycarbonyloxyalkyl group or [1- (CH) -CO-0-CO- (CH) _ (p is an arbitrary natural number)].
  • Examples of the group containing a hydroxyl group include a group containing a phenolic hydroxyl group such as a hydroxyphenyl group and a hydroxyphenylalkyl group; and an alcoholic hydroxyl group such as a hydroxyalkyl group, a hydroxyalkoxy group and a hydroxyalkoxycarbonyl group. And a group containing:
  • Examples of the group containing an imide group include an N-phenyldicarboximide group.
  • preferred specific examples of the specific polar group or the group containing the specific polar group include a carboxyl group, a hydroxycarbonylmethyl group, a carbonyloxycarbonyl group, a hydroxyyl group, a hydroxymethoxy group, a 2-hydroxyethoxy group.
  • the alicyclic olefin resin used in the present invention may have only one type of specific polar group, or may have a combination of two or more types. From the viewpoint of highly balancing the various properties of the resin composition of the present invention and the resin film obtained from the composition, the alicyclic resin preferably has a combination of two or more types. It is particularly preferred to have a carboxyl group and an imide group.
  • a resin having a repeating unit represented by the above formula (I) is preferable because it gives a resin film having excellent transparency.
  • R 1 R 4 are each independently a hydrogen atom or a group represented by the formula: -X-R Represents a group.
  • at least one of R 1 to R 4 is a group represented by the formula: -X n _R a (R a represents the above-mentioned specific polar group).
  • R 1 - of R 4 any two of the formula: is a group represented by -XR a, different carbon (For example, R 1 and R 3) arbitrarily is preferable're bound to.
  • X examples include an alkylene group such as a methylene group, an ethylene group, and a propylene group; an arylene group such as an o-phenylene group, an m-phenylene group, a p-phenylene group, and a naphthalene group; a group represented by; single R b _CO- R b - (R b represents an alkylene group or Ariren group.) a group represented by; and the like are.
  • specific examples of the alkylene group and the arylene group for R b include those similar to the alkylene group and the arylene group for X.
  • n 0 or 1.
  • n is an integer of 0 to 2, and is preferably 0 or 1.
  • R is an alkyl group having 17 to 17 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 8 carbon atoms which may have a substituent, an aromatic group, or the aforementioned specific group. Represents a polar group.
  • Examples of the alkyl group having 17 carbon atoms include a methynole group, an ethyl group, an n-propyl group, an isopropyline group, an n-butyl group, an isobutyl group, a t-butyl group, an s-butyl group, an n-pentyl group, and a 1-methylbutyl group.
  • Examples of the C 3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group and the like.
  • substituents examples include a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; a hydroxyl group; an acyl group such as an acetyl group and a benzoyl group; an alkoxyl group such as a methoxy group, an ethoxy group, and an isopropoxy group; Carbonyl groups such as methoxycarbonyl, ethoxycarbonyl and t-butoxycarbonyl; alkylcarbonyl groups such as acetooxy; benzoyloxy Aryloxycarbonyl group; nitro group; cyano group; and the like.
  • halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom
  • a hydroxyl group such as an acyl group such as an acetyl group and a benzoyl group
  • an alkoxyl group such as a methoxy group, an ethoxy group, and an
  • Examples of the aromatic group include a phenyl group which may have a substituent such as a phenyl group, a 2-chlorophenyl group or a 4-methylphenyl group; a 1-naphthyl group, a 2-naphthyl group, a 6- Methyl-11-naphthyl group and other substituents; naphthyl group; 2-pyridyl group, 3_pyridyl group and 4-pyridinole group and other substituents. And pyridyl groups.
  • the method for obtaining the alicyclic olefin resin used in the present invention is not particularly limited, and examples thereof include the following method (i)-(iv).
  • a resin obtained by polymerizing an alicyclic olefin monomer having no specific polar group in the presence of a radical polymerization initiator is known by using a compound having a specific polar group. Method to introduce a specific polar group by denaturation according to the method.
  • Examples of the compound containing a specific polar group include acrylic acid, methacrylic acid, sodium ethacrylic acid, 2-hydroxyethylacrylic acid, 2-hydroxyethyl methacrylic acid, maleic acid, fumaric acid, itaconic acid, Unsaturated carboxylic acids such as endocis-bicyclo [2.2.1] hept_5_en-2,3-dicanolevonic acid and methinoleic endocis-bicyclo [2.2.1] hept-5-ene-2,3-dicarboxylic acid Acid compounds and imide derivatives thereof; unsaturated carboxylic anhydrides such as maleic anhydride, maleic anhydride, butulic succinic anhydride, tetrahydrophthalic anhydride and citraconic anhydride; and the like.
  • the polar group other than the specific polar group is a group that can be derived to a specific polar group by a chemical reaction such as hydrolysis or reduction.
  • a chemical reaction such as hydrolysis or reduction.
  • Re is a linear, branched or alicyclic, saturated or unsaturated hydrocarbon group.
  • the saturated hydrocarbon group or unsaturated hydrocarbon group may be substituted with a group containing a halogen atom, a silicon atom, an oxygen atom or a nitrogen atom (excluding a hydroxyl group and a hydroxycarboxy group).
  • the alicyclic olefin monomer having no specific polar group when subjected to radical polymerization, the alicyclic olefin monomer may be optionally combined with the alicyclic olefin monomer.
  • Other monomers capable of addition copolymerization or ring-opening copolymerization hereinafter, referred to as “other monomers” may be added.
  • the unsaturated bond portion of the obtained resin may be hydrogenated according to a conventional method.
  • the unsaturated bond portion of the obtained resin may be hydrogenated by a conventional method. You may.
  • an alicyclic olefin monomer having no specific polar group and an alicyclic olefin monomer having a specific polar group are combined with each other in the presence of an organic ruthenium polymerization catalyst.
  • the unsaturated bond portion is hydrogenated according to a conventional method, and if necessary, a polar group other than the specific polar group is induced to a specific polar group by hydrolysis or the like.
  • a polar group other than the specific polar group is induced to a specific polar group by hydrolysis or the like.
  • the organic ruthenium polymerization catalyst used herein is a ruthenium-containing catalyst that promotes ring-opening polymerization.
  • a polymerization catalyst containing an organic ruthenium compound to which a neutral electron donating ligand is coordinated as a main component is preferable.
  • Neutral electron donating ligands are ligands that have a neutral charge when separated from the central metal (ie, ruthenium).
  • More preferred organic ruthenium compounds are those in which an anionic ligand is coordinated together with a neutral electron donating ligand.
  • Anionic ligands are ligands that have a negative charge when separated from ruthenium.
  • the organic ruthenium compound may further include a counter anion.
  • the counter anion is not particularly limited as long as it can form an anion that forms an ion pair with a ruthenium cation, and can form such a pair.
  • organic ruthenium compound examples include bis (tricyclohexylphosphine) benzene.
  • Tenidimudichloride bis (1,3-diisopropylimidazoline-1-2-ylidene) benzylidene lutedichloride, bis (1,3-dicyclohexylimidazoline-2-ylidene) benzylidene tenidimudichloride, (1,3-dimesityl) Imidazoline-l- 2-ylidene) (tricyclohexylphosphine
  • pyridines; phosphines; and 1,3-diisopropylimidazoline-2_ylidene and 1,3-dimesitylimidazolidine_2_ylidene such as those described above.
  • a neutral electron-donating compound such as a nitrogen heterocyclic carbene compound is added at a ratio of 1 to 100 times in weight ratio to ruthenium metal in the polymerization catalyst.
  • diazo compounds such as N CHCOOEt
  • acetylene compounds such as phenylacetylene
  • a silyl compound such as SiH or Ph MeSiH;
  • Et represents an ethyl group
  • Ph represents a phenyl group
  • Me represents a methyl group
  • an aromatic polymerizable monomer is used instead of part or all of the alicyclic olefin monomer.
  • the desired alicyclic olefin resin can also be obtained by a method of polymerizing and hydrogenating an aromatic carbon-carbon double bond of the obtained resin.
  • dodecane force one 3- E down , 5, 6-di (hydroxy-carbonyl) tetracyclo [4.4.0.1 2, 5 .1 ⁇ , 10] dodecane force - 3 E emissions, 5 _ methyl - 5-hydroxycarbonyltetracyclo [4.4.0.
  • Kisashikuro to El [6 ⁇ 6.1. I 3 ' 6.
  • I 3 '. 6 I 10' 13 0 2 '7 .0 9' 14] heptadecyl force -. 4-E down, 11, 12 to the di (hydroxycarbonyl) Kisashikuro [6 .6 1. I 3 '6.
  • Kisashikuro to 11-hydroxy [6.6. 1. I 3 '6 . I 10' 13 .0 2 '7 .0 9' 14] heptadecyl force one 4-E down, Kisashikuro [6.6 to 11-hydroxymethyl. 1. I 3 '6. I 10 ' 13 .0 2,7 .0 9 '14] heptadeca 4-E down, 11, 12-bis Kisashikuro to (hydroxymethyl) [6 ⁇ 6.1 I 3,6 I 10, 13 .0 2 '7 .0 9' 14..] Heptadecyl force - 4 E down, Kisashikuro to 11- (2-hydroxyethoxy carbonyl) [6 • 6. 1. I 3 '6.
  • N-phenyl-substituted imido compounds such as N-phenyl (5-norbornene-2,3-dicarboximide);
  • Bicycloheptene derivatives such as 5-hydroxycarbonylbicyclo [2.2.1] hept_2_ene, 5,6-di (hydroxycarbonyl) bicyclo [2.2.1] hept-2-ene, and 8-hydro Xicarbonyltetracyclo [4.4.0. I 2 ' 5.
  • I 7 ' 10 Dode force-3-ene, 8, 9-di (hydroxycarbonyl) tetracyclo [4.4.0. I 2 ' 5.
  • I 7 Tetorashikurodode Sen derivatives such as' 10] de de force one 3-E down;
  • N-phenyl-substituted compounds such as N-phenyl (5-norbornene-2,3-dicarboximide) Midig compounds; etc.
  • the alicyclic olefin monomer having no specific polar group includes the following (e) and (f).
  • Pentade force one 4, 11-diene, cyclopentene, Shikuropentaji E emissions, 1, 4 Metano one 1, 4, 4a, 5, 10, Kisahidoro to 10a_ Anthracene, 8_ fenirutetracyclo [4. 4. 0. I 2 ' 5. I 7 ' 10 ]
  • (C) a group capable of being modified into a hydroxyl group, such as a formate such as a bicycloheptene derivative, a tetracyclododecene derivative, or a hexacycloheptadecene derivative, an acetate, a propionate, a butyrate, a valate, or a benzoate ;
  • alicyclic olefin monomers can be used alone or in combination of two or more.
  • Other monomers include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methynol-1-butene, 3-methynol-1-pentene, and 3-ethynol-1 —Pentene, 4—Methinole 1_pentene, 4—Methinole 1—hexene, 4,4—Dimethine 1—hexene, 4, 4-Dimethine 1—pentene, 4—Echinole 1—Hexene 1-hexene, 1-hexene, 1-otene, 1-decene, 1-dodecene, 1-tetradecene, 1_hexadecene, 1-octadecene, 1-ejicocene, etc.
  • C2-20 ethylene or ⁇ —Olefin C2-20 ethylene or ⁇ —Olefin; non-conjugated gens such as 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methinole 1,4-hexadiene, and 1,7-octadiene; These monomers can be used alone or in combination of two or more.
  • ⁇ -olefins when used for ring-opening copolymerization of alicyclic olefin monomers, function as a molecular weight regulator described later.
  • the molecular weight of the ring-opened polymer can be adjusted. It will be easier.
  • the amount of the molecular weight modifier used is small, a polymer having a relatively large weight average molecular weight (Mw) is obtained, and when it is large, a polymer having a relatively small weight average molecular weight (Mw) is obtained.
  • a molecular weight regulator As a molecular weight regulator, a Bürich compound, a gen compound or the like can be used.
  • bur compound examples include fluorinated compounds such as 1-butene, 1-pentene, 1-hexene, and 1-otathene; styrene compounds such as styrene and burtonolene; ethers such as ethyl butyl ether, isobutyl butyl ether and aryl glycidyl ether.
  • fluorinated compounds such as 1-butene, 1-pentene, 1-hexene, and 1-otathene
  • styrene compounds such as styrene and burtonolene
  • ethers such as ethyl butyl ether, isobutyl butyl ether and aryl glycidyl ether.
  • Compounds; halogen-containing compound such as aryl chloride; aryl acetate, aryl alcohol, glycyl Oxygen-containing vinyl compounds such as zirmetarylate; nitrogen-containing vinyl compounds such as
  • Examples of the gen compounds include non-conjugated gens such as 1,4 pentadiene, 1,5-hexadiene, 1,6-hexadiene, 2-methinolee 1,4 pentadiene, 2,5-dimethinolee 1,5-hexadiene, and the like.
  • Compounds; synergistic gen compounds such as 1,3-butadiene, 2-methinolay 1,3-butadiene, 2,3-dimethinole-1,3-butadiene, 1,3_pentadiene, and 1,3-hexadiene;
  • a horefin compound such as 1-hexene is particularly preferable.
  • Examples of the obtained alicyclic olefin resin include a ring-opened polymer of an alicyclic olefin monomer and a hydrogenated product thereof, an addition polymer of an alicyclic olefin monomer, and an alicyclic olefin resin. Addition polymer of monomer and vinyl compound, monocyclic cycloalkene polymer, alicyclic conjugated polymer, vinyl-based alicyclic hydrocarbon polymer and its hydrogenated product, aromatic olefin polymer And hydrogenated aromatic rings. In the present invention, these alicyclic resin may be used alone or in combination of two or more.
  • ring-opened polymers of alicyclic olefin monomers and hydrogenated products thereof addition polymers of alicyclic olefin monomers, and attachments of alicyclic olefin monomers and vinyl compounds
  • a hydrogenated product of a ring-opened polymer of an alicyclic olefin monomer is particularly preferred, in which a polymer or an aromatic ring hydrogenated product of an aromatic olefin polymer is preferred.
  • Examples of the inorganic fine particles used in the present invention include simple metals, inorganic oxides, inorganic carbonates, inorganic sulfates, inorganic phosphates, and the like. From the viewpoints of heat resistance and oxidation resistance, inorganic oxides are preferred. Oxides are particularly preferred.
  • metal oxides examples include silicon oxides such as colloidal silica, aerosil, and glass; aluminum oxides such as alumina; zirconium oxides such as zirconia; and titanium oxides such as titania.
  • silicon oxides such as colloidal silica, aerosil, and glass
  • aluminum oxides such as alumina
  • zirconium oxides such as zirconia
  • titanium oxides such as titania.
  • colloidal silica is particularly preferred from the viewpoint of productivity in which colloidal silica, anoremina, zirconia, and titania are preferred.
  • the primary particle diameter of the inorganic fine particles used in the present invention is generally 11 to 200 nm, preferably 11 to 150 nm, more preferably 5 100 nm from the viewpoints of transparency and pattern formability.
  • the primary particle diameter is measured by the BET method (specific surface area measurement method) based on the true density assuming a true sphere.
  • the amount of the inorganic fine particles used can be arbitrarily selected according to the use of the resin film to be formed.
  • the amount of the inorganic fine particles used can be arbitrarily selected according to the use of the resin film to be formed.
  • the resin film to be formed usually 51,000 parts by weight, preferably 5800 parts by weight, more preferably 5800 parts by weight, based on 100 parts by weight of the alicyclic olefin resin having a specific polar group described above. 10 500 parts by weight.
  • the solvent used in the present invention is not particularly limited as long as it contains an organic solvent (a good solvent) in which the alicyclic olefin resin can be dissolved.
  • the good solvent those having a solubility of 20% by weight or more at 23 ° C. of the alicyclic olefin resin are preferable.
  • the amount of the good solvent used is usually 500 parts by weight or more based on 100 parts by weight of the alicyclic olefin resin, and from the viewpoint of obtaining desired transparency, 500 to 10,000 parts by weight is preferred. Masu 500-5,000 parts by weight are more preferred 900-2,000 parts by weight are particularly preferred.
  • Examples of good solvents include glycol ethylene compounds such as diethylene glycol dimethyl ether, diethylene glycol methyl methyl ether, diethylene glycol dimethyl ether, and propylene glycol methylethyl ether; propylene glycol monomethyl ether, propylene glycol monoethyl ether; Glycol monoether compounds such as propylene glycol monoisopropyl ether and propylene glycol mono-n-butyl ether; amidated compounds such as N_methyl-2-pyrrolidone and N, N-dimethylacetamide; alicyclic ethers such as tetrahydrofuran Alicyclic ketone compounds such as cyclohexanone; and the like.
  • glyco-ester compounds, glycol monoether compounds, and amide compounds are preferred because of the ease of filtration of the resin composition.
  • a mixed solvent of a good solvent and a solvent other than the good solvent may be used.
  • the poor solvent include glycol monoether acetate conjugates such as propylene glycol monomethyl ether acetate.
  • the use amount of the poor solvent is usually 200% by weight or less, preferably 100% by weight or less based on the good solvent, since it is easy to obtain a resin film having excellent in-plane film thickness uniformity.
  • the resin composition of the present invention can add various additives according to the purpose.
  • the additive examples include a photosensitizer such as a quinonediazide compound; a crosslinking agent having at least two reactive groups such as an amino group, a carboxyl group, a hydroxyl group, an epoxy group, an isocyanate group, and a butyl group (a preferable specific example is a methylol compound).
  • curing components such as curing aids such as solid sulfonic acid compounds and amine compounds such as imidazole compounds; surfactants such as fluorine compounds and silicon compounds; hindered phenol compounds and the like Antioxidants; adhesion aids such as silane coupling agents; sensitizers such as phenolic compounds; antistatic agents; defoamers; dispersants;
  • the alicyclic olefin resin and the inorganic microparticles are excellent in operability and in that a composition excellent in filterability is obtained.
  • an alicyclic olefin resin solution hereinafter, simply referred to as “resin solution”
  • an inorganic fine particle dispersion respectively, and then mixing both.
  • These liquid media can be all or part of the solvent constituting the resin composition of the present invention.
  • liquid medium (solvent) used for dissolving the alicyclic olefin resin the glycol diether conjugates, glycol monoether compounds, and amide compounds, which are preferably used in the above-described good solvent, are particularly preferable. preferable.
  • liquid medium used to disperse the inorganic fine particles
  • examples of the liquid medium (dispersion medium) used to disperse the inorganic fine particles include glycol monoether acetate compounds, glycol diether compounds, Glycol monoether compounds and amide compounds are particularly preferred.
  • the dispersion medium may be used as it is in the production of the resin composition, or the dispersion medium may be replaced with another dispersion medium (dispersion medium exchange) if necessary. Can be. Even when the dispersion medium is water, the dispersion medium can be exchanged for use.
  • the method of mixing the resin solution and the inorganic fine particle dispersion There is no particular limitation on the method of mixing the resin solution and the inorganic fine particle dispersion. Regardless of whether the inorganic fine particle dispersion is added to the resin solution or the resin solution is added to the inorganic fine particle dispersion, both are simultaneously placed in a container. However, from the viewpoint of preventing aggregation of the fine particles, a method of adding a resin solution to the inorganic fine particle dispersion is preferable.
  • the temperature at the time of mixing there is no particular limitation on the temperature at the time of mixing, but it is general to set the temperature at which evaporation can be suppressed in consideration of the boiling point of the solvent in the resin composition. Therefore, the mixing temperature at normal pressure is usually 10-50 ° C, preferably 10-40 ° C, more preferably 15-35 ° C.
  • a container equipped with a stirrer or a container installed in a shaker may be used.
  • the resin composition of the present invention is capable of forming a resin film having excellent in-plane film thickness uniformity. It is preferable because a film can be formed.
  • the filtration speed was measured at room temperature (23 ° C) under a pressure of 0.5 kgf / cm 2 (gauge pressure) using a membrane filter with a diameter of 47 mm, a pore diameter of 1 ⁇ , and a porosity of 83%.
  • the average speed when filtration is performed, and this speed is usually 20 g / min or more, preferably 30 g / min or more, and more preferably 40 g / min or more.
  • a resin composition having such a filtration rate gives a resin film having particularly excellent in-plane thickness uniformity.
  • the porosity is a ratio of the pore volume to the total volume of the membrane filter including the pores.
  • a resin composition having a filtration rate in the above-described range can be easily obtained by the above-described method for producing a resin composition of the present invention.
  • a method for adjusting the filtration rate using the same component a method for adjusting the amount of the solvent may be employed.
  • a resin film having a thickness of 0.1200 xm can be easily formed.
  • the obtained resin film is a thin film having both excellent transparency and in-plane thickness uniformity.
  • the resin film of the present invention can be formed on a substrate of any shape. Although the resin film of the present invention can be used together with the substrate, the resin film can be used alone by peeling the resin film from the substrate as necessary.
  • the type and material of the substrate used for forming the resin film of the present invention are not particularly limited.
  • the substrate to be used may be a single-layer substrate or a substrate having a plurality of layers.
  • Specific examples of the substrate used include a substrate having wiring such as a printed wiring board and a display substrate; a flat substrate such as a glass substrate; and a resin or a resin which is appropriately separated from the resin film after forming the resin film.
  • Examples of a method for applying the resin composition of the present invention on a substrate include a method such as a spray method, a roll coating method, and a spin coating method.
  • the temperature at which the coating film of the resin composition is heated and dried is usually 150 to 300 ° C, preferably 200 to 250 ° C.
  • a curing component such as a crosslinking agent may be added to the resin composition of the present invention.
  • a curing component When a curing component is added, the resin film can be cured on the substrate by heating.
  • heating method for curing there is no particular limitation on the heating method for curing.
  • a coating film of the resin composition of the present invention containing a curing component is heated * dried and then further heated.
  • Heating for curing can be performed by a heating device such as a hot plate or an oven.
  • the resin film may cover the entire substrate or may partially cover the substrate surface such as in a pattern.
  • a method for forming a patterned resin film on a substrate there is a photolithography method using the resin composition of the present invention to which a photosensitive agent is added.
  • a resin composition containing a photosensitive agent is applied on a substrate in the same manner as described above, and dried (pre-beta).
  • the resin film thus obtained is irradiated with active radiation through a mask pattern, if necessary, to form a latent image pattern in the resin film, and the resin film having the latent image pattern is subjected to alkali development.
  • the type of actinic radiation is not particularly limited, and examples thereof include visible light, ultraviolet light, far ultraviolet light, X-rays, electron beams, and proton beam rays, with visible light and ultraviolet light being preferred.
  • the radiation dose for irradiation can be set arbitrarily according to the purpose of use of the transparent resin film, the thickness of the film, and the like.
  • the pattern may be formed by irradiating actinic radiation through a mask, or may be formed by directly drawing with an electron beam or the like.
  • the resin film of the present invention is excellent in transparency.
  • the transparency of the resin film can be evaluated by measuring the transmittance of the resin film with a spectrophotometer.
  • the resin film of the present invention has excellent in-plane thickness uniformity.
  • the in-plane film thickness uniformity is measured by measuring the in-plane film thickness under the conditions described in the examples and evaluating the in-plane film thickness and the difference between the maximum value and the minimum value of the film thickness. It can be evaluated that the smaller the difference is, the more excellent the in-plane film thickness uniformity is.
  • the film-like or pattern-like resin film of the present invention not only has excellent in-plane film thickness uniformity, but also has excellent electrical properties such as dielectric properties. Therefore, it can be used as an electronic component such as a display element, an integrated circuit element, and a solid-state imaging device, and a resin film for an electronic component such as a color filter for a display, a protective film, a flattening film, and an electric insulating film.
  • the average particle size of the inorganic fine particles is determined by the specific surface area 0 "(manufactured by Shimadzu Corporation) and the BET method (specific surface area measurement method), which calculates the surface area from the amount of nitrogen gas adsorbed, according to the method of JIS Z8830.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were determined by gel permeation chromatography (GPC) using cyclohexane as an eluent.
  • the hydrogenation rate was determined by measuring the 1 ⁇ -NMR spectrum and calculating the ratio (mol%) of hydrogenated carbon-carbon double bonds to carbon-carbon double bonds before hydrogenation.
  • the water flow rate was obtained by filtering distilled water at 25 ° C filtered through a membrane filter with a pore diameter of 0.1 ⁇ under reduced pressure of -0.069 MPa, and displaying the flow rate in ml / min per lcm 2. It is.
  • the transmittance of the resin film thus formed was measured with a spectrophotometer.
  • the transmittance was calculated by converting the film thickness to 2 zm and calculating the total light transmittance so that the two could be compared. The higher the value, the better the transparency.
  • 0.7mm thick x 650mm long x 550mm wide glass substrate (made by Koingen Co., Ltd.) was deposited at a thickness of 2000 A to prepare a chromium-deposited glass substrate.
  • This chromium-deposited glass substrate was spin-coated at a rotation speed of 16.7 revolutions / second, and the resulting coating film was dried on a hot plate at 100 ° C for 2 minutes under a nitrogen atmosphere to obtain a film thickness.
  • a resin film of 1.5 / m was obtained.
  • This resin solution (a) was transferred into an autoclave equipped with a stirrer, and the hydrogen pressure was 4 MPa and the temperature was
  • the activated carbon was separated by filtration through a 0.2 / im fluororesin filter to obtain a resin solution (c).
  • the filtration could be performed without delay.
  • the mixture was stirred and stirred to prepare a silica sol dispersion (1) having a silica sol concentration of 20%.
  • the primary particle size of the silica sol particles in this dispersion (1) was about 20 nm.
  • this silica sol dispersion (1) and 150 parts of the resin solution (1) are mixed, and 0.1 part of a silicon-based surfactant (product name “KP-341” manufactured by Shin-Etsu Chemical Co., Ltd.) is added. After mixing and dissolving, the mixture was further stirred for 30 minutes to obtain a resin composition (1). For the resin composition (1), the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • a silicon-based surfactant product name “KP-341” manufactured by Shin-Etsu Chemical Co., Ltd.
  • a silica sol dispersion liquid (2) was prepared.
  • the primary particle size of the silica sol particles in this dispersion (2) was about 20 nm.
  • 150 parts of this silica sol dispersion (2) and 150 parts of the resin solution (1) were mixed, and 0.1 part of a silicon-based surfactant (product name “KP-341”, manufactured by Shin-Etsu Chemical Co., Ltd.) was added. After mixing and dissolving, the mixture was further stirred for 30 minutes to obtain a resin composition (2).
  • the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • a silica sol dispersion liquid (3) having a silica zone concentration of 20% was prepared.
  • the primary particle size of the silica sol particles in this dispersion (3) was about 20 nm.
  • the resin solution (1) was changed to the resin solution (2), and the silica sol dispersion (1) was changed to the silica sol dispersion (
  • a resin composition (3) was prepared in the same manner as in Example 1 except that the composition was changed to 3).
  • the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • PGMEA propylene glycol monomethyl ether acetate
  • solid content concentration 30%
  • the resin solution (1) was changed to the resin solution (3), and the silica sol dispersion (1) was changed to the silica sol dispersion (
  • a resin composition (4) was prepared in the same manner as in Example 1 except that the composition was changed to 4).
  • the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • a resin composition (5) was prepared in the same manner as in Example 1 except that the composition was changed to (4).
  • the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • a resin composition (6) was prepared in the same manner as in Example 1 except that the composition was changed to (5).
  • the filtration rate was measured, and the transparency and the in-plane film thickness uniformity were evaluated.
  • a silica sol dispersion liquid (5) was prepared by adding 50 parts of cyclohexane (CH) to 100 parts of an organosilica sol (product name “PMA-ST”, manufactured by Nissan Chemical Industries, Ltd.) and mixing.
  • the primary particle diameter of the silica sol particles in this dispersion (5) was about 20 nm.
  • the resin composition (8) was not a uniform solution due to precipitation of fine particles.
  • the resin composition of the present invention contains an alicyclic olefin resin having a specific polar group, inorganic fine particles, and a solvent, and has excellent filterability, excellent transparency, and excellent in-plane film thickness uniformity. It is useful as a material for forming a resin film having both functions.
  • the resin film of the present invention is excellent in electrical properties such as transparency, in-plane film thickness uniformity, and dielectric properties. Therefore, it can be used as an electronic component such as a display element, an integrated circuit element, and a solid-state imaging device, and a resin film for an electronic component such as a display color filter, a protective film, a flattening film, and an electric insulating film.

Abstract

: Une composition de résine, caractérisée en ce qu'elle comprend une résine oléfine alicyclique ayant, dans sa molécule, un ou plusieurs éléments sélectionnés à partir d'un groupe carboxyle, d'un groupe d'anhydride acide dicarboxylique, d'un groupe hydroxyle et d'un groupe imide, de fines particules inorganiques, et d'un solvant; une méthode de production; et un film de résine étant formé à partir de la composition de résine et ayant une épaisseur de 1 à 200 µm. La composition de la résine est utilisée en tant que matériau pour la formation d'un film de résine qui présente d'excellentes caractéristiques de filtration et combine une excellente transparence et une uniformité d'épaisseur dans un plan. Le film de résine peut être avantageusement utilisé pour des pièces électroniques telles que éléments d'écran, circuits intégrés et éléments de photographie statiques, et comme film de résine pour des pièces électroniques telles qu'un filtre couleur pour un écran, un film protecteur, un film égalisateur et un film d'isolement électrique.
PCT/JP2005/001212 2004-01-30 2005-01-28 Composition de résine, méthode de sa production et du film de résine WO2005073310A1 (fr)

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KR1020067015333A KR101220604B1 (ko) 2004-01-30 2005-01-28 수지 조성물, 그의 제조방법 및 수지막
JP2005517514A JP4997766B2 (ja) 2004-01-30 2005-01-28 樹脂組成物、その製造方法及び樹脂膜
CN200580003684XA CN1914271B (zh) 2004-01-30 2005-01-28 树脂组合物、其制备方法和树脂膜

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Cited By (5)

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JP2006206798A (ja) * 2005-01-31 2006-08-10 Nippon Zeon Co Ltd 表示デバイス用樹脂組成物及びこれを用いた積層体
WO2008105244A1 (fr) * 2007-02-28 2008-09-04 Zeon Corporation Substrat de matrice active, son procédé de fabrication, et dispositif d'affichage plat
WO2008123234A1 (fr) * 2007-03-30 2008-10-16 Zeon Corporation Substrat de matrice active et son procédé de fabrication
JP2011528385A (ja) * 2008-07-18 2011-11-17 エボニック デグサ ゲーエムベーハー 疎水化二酸化ケイ素粒子及びその顆粒の分散液
JP2012077194A (ja) * 2010-09-30 2012-04-19 Nippon Zeon Co Ltd 変性シリカ分散液及びその製造方法、並びに絶縁材料用樹脂組成物

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KR101009318B1 (ko) * 2008-07-21 2011-01-18 부산대학교 산학협력단 페닐기를 포함하는 폴리노보넨디카르복시이미드 필름 및이를 적용한 유기전기발광소자
CN102024562B (zh) * 2009-09-17 2016-03-09 大赛璐化学工业株式会社 用于制造叠层陶瓷部件的溶剂或溶剂组合物
KR102503173B1 (ko) * 2016-03-31 2023-02-23 동우 화인켐 주식회사 플렉서블 컬러필터
KR102159253B1 (ko) * 2016-11-01 2020-09-23 동우 화인켐 주식회사 필름 안테나 장치 및 그의 제조 방법
KR20210121643A (ko) 2020-03-31 2021-10-08 동우 화인켐 주식회사 경화성 수지 조성물 및 이를 이용하여 제조된 투명필름
KR102636067B1 (ko) 2020-03-31 2024-02-13 동우 화인켐 주식회사 경화성 수지 조성물 및 이를 이용하여 제조된 투명필름
KR20210121645A (ko) 2020-03-31 2021-10-08 동우 화인켐 주식회사 경화성 수지 조성물 및 이를 이용하여 제조된 투명필름
KR102243738B1 (ko) * 2020-09-16 2021-04-23 동우 화인켐 주식회사 필름 안테나 장치 및 그의 제조 방법

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JP2006206798A (ja) * 2005-01-31 2006-08-10 Nippon Zeon Co Ltd 表示デバイス用樹脂組成物及びこれを用いた積層体
WO2008105244A1 (fr) * 2007-02-28 2008-09-04 Zeon Corporation Substrat de matrice active, son procédé de fabrication, et dispositif d'affichage plat
WO2008123234A1 (fr) * 2007-03-30 2008-10-16 Zeon Corporation Substrat de matrice active et son procédé de fabrication
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JP2011528385A (ja) * 2008-07-18 2011-11-17 エボニック デグサ ゲーエムベーハー 疎水化二酸化ケイ素粒子及びその顆粒の分散液
JP2012077194A (ja) * 2010-09-30 2012-04-19 Nippon Zeon Co Ltd 変性シリカ分散液及びその製造方法、並びに絶縁材料用樹脂組成物

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CN1914271A (zh) 2007-02-14
JP4997766B2 (ja) 2012-08-08
JPWO2005073310A1 (ja) 2007-10-11
KR20070011281A (ko) 2007-01-24
CN1914271B (zh) 2010-12-29
TW200537243A (en) 2005-11-16
KR101220604B1 (ko) 2013-01-10
TWI375120B (fr) 2012-10-21

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