WO2022225003A1 - 膜形成用組成物 - Google Patents
膜形成用組成物 Download PDFInfo
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- WO2022225003A1 WO2022225003A1 PCT/JP2022/018404 JP2022018404W WO2022225003A1 WO 2022225003 A1 WO2022225003 A1 WO 2022225003A1 JP 2022018404 W JP2022018404 W JP 2022018404W WO 2022225003 A1 WO2022225003 A1 WO 2022225003A1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/28—Nitrogen-containing compounds
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- C08K3/00—Use of inorganic substances as compounding ingredients
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- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Definitions
- the present invention relates to a film-forming composition.
- liquid crystal displays organic electroluminescence (EL) elements (organic EL displays and organic EL lighting), touch panels, optical semiconductors (light-emitting diodes (LEDs), etc.) elements, solid-state imaging elements, organic thin-film solar cells, dye-sensitized solar cells , and organic thin film transistors (TFTs)
- EL organic electroluminescence
- LEDs light-emitting diodes
- TFTs organic thin film transistors
- a polymer containing a repeating unit having a triazine ring and an aromatic ring has a high refractive index, and the polymer alone has high heat resistance, high transparency, high refractive index, high solubility, It has already been found that it can achieve low volume shrinkage and is suitable as a film-forming composition for producing electronic devices (Patent Document 1).
- the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a film-forming composition capable of forming a thin film having a high refractive index, transparency and excellent solvent resistance (crack resistance). do.
- the present inventors have found that by using a triazine ring-containing polymer having at least one triazine ring terminal and specific inorganic fine particles, a high refractive index, transparency and The inventors have found that a thin film having excellent solvent resistance can be formed, and completed the present invention.
- the present invention provides the following triazine ring-containing polymer and film-forming composition.
- a triazine ring-containing polymer comprising a repeating unit structure represented by the following formula (1) and having at least one triazine ring terminal; a cross-linking agent; inorganic fine particles having a hydrophilic group and a crosslinkable group on the surface; an organic solvent;
- a film-forming composition comprising: (In formula (1), R and R′ independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group; Q is a ring structure having 3 to 30 carbon atoms; represents a valence group.* represents a bond.)
- Q in formula (1) represents at least one selected from the group represented by formulas (2) to (13) and formulas (102) to (115).
- R 1 to R 92 are each independently a hydrogen atom, a halogen atom, a carboxy group, a sulfo group, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, represents a halogenated alkyl group or an alkoxy group having 1 to 10 carbon atoms
- R 93 and R 94 each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- W 1 and W 2 are each independently a single bond
- CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom, a C 1-10 alkyl group (provided that these may form a ring), or represents a halogenated alkyl group having 1 to 10 carbon atoms.
- C ⁇ O, O, S, SO, SO 2 , or NR 97 R 97 is represents a hydrogen atom, an alkyl group having 1 to 10 carbon carbon atoms
- a thin film produced from the film-forming composition of the present invention can exhibit properties such as high heat resistance, high refractive index, low volume shrinkage, and solvent resistance (crack resistance).
- the thin film produced from the film-forming composition of the present invention has high transparency and high refractive index and solvent resistance (crack resistance), so it is used as a flattening layer and a light scattering layer for organic EL lighting.
- the light extraction efficiency (light diffusion efficiency) can be improved, and the durability can be improved.
- FIG. 1 is a 1 H-NMR spectrum diagram of polymer compound [8] obtained in Synthesis Example 1-1.
- FIG. 1 is a diagram showing the transmittance of cured films produced in Example 1-1 and Comparative Example 1-1.
- FIG. 1 is a diagram showing the transmittance of cured films produced in Example 1-1 and Comparative Example 1-1.
- the film-forming composition according to the present invention contains a triazine ring-containing polymer, a cross-linking agent, inorganic fine particles, and an organic solvent.
- Triazine Ring-Containing Polymer contains a repeating unit structure represented by the following formula (1).
- a triazine ring-containing polymer is, for example, a so-called hyperbranched polymer.
- a hyperbranched polymer is a highly branched polymer having an irregularly branched structure.
- the term "irregular" as used herein means that the branch structure is more irregular than that of a dendrimer, which is a highly branched polymer having a regular branch structure.
- a triazine ring-containing polymer which is a hyperbranched polymer, has a structure larger than the repeating unit structure represented by formula (1), and each of the three bonds of the repeating unit structure represented by formula (1) has , and a structure (structure X) in which repeating unit structures represented by formula (1) are bonded.
- the structure X is distributed throughout the triazine ring-containing polymer except for the terminals.
- the repeating unit structure may consist essentially of the repeating unit structure represented by formula (1).
- R and R′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group. preferable.
- the number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20. Considering that the heat resistance of the polymer is further improved, the number of carbon atoms in the alkyl group is 1 to 10. More preferably, 1 to 3 are even more preferable.
- the structure of the alkyl group is not particularly limited, and may be, for example, linear, branched, cyclic, or a combination of two or more thereof.
- alkyl groups are methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl.
- n-pentyl 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2 , 2-dimethyl-n-propyl, 1-ethyl-n-propyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3- dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl-cyclopropyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 3-methyl-n-pentyl, 4-methyl -n-pentyl, 1,1-dimethyl-n-butyl, 1,2-dimethyl-n-butyl, 1,3-dimethyl-n-butyl,
- the number of carbon atoms in the alkoxy group is not particularly limited, it is preferably 1 to 20, and in consideration of further increasing the heat resistance of the polymer, the number of carbon atoms in the alkoxy group is more preferably 1 to 10. 1 to 3 are even more preferred.
- the structure of the alkyl moiety is not particularly limited, and may be, for example, linear, branched, cyclic, or a combination of two or more thereof.
- alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, 1-methyl-n-butoxy, 2-methyl-n -butoxy, 3-methyl-n-butoxy, 1,1-dimethyl-n-propoxy, 1,2-dimethyl-n-propoxy, 2,2-dimethyl-n-propoxy, 1-ethyl-n-propoxy, n -hexyloxy, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-butoxy, 2,2-dimethyl-n-butoxy, 2,3-dimethyl-n-butoxy, 3,3-dimethyl-n-butoxy, 1-ethoxy,
- the number of carbon atoms in the aryl group is not particularly limited, it is preferably 6 to 40, and in consideration of further increasing the heat resistance of the polymer, the number of carbon atoms in the aryl group is more preferably 6 to 16. 6 to 13 are even more preferred.
- the aryl group includes an aryl group having a substituent. Examples of substituents include halogen atoms, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, nitro groups, and cyano groups.
- aryl groups include phenyl, o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, o-fluorophenyl, p-fluorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, p-cyanophenyl, ⁇ -naphthyl, ⁇ -naphthyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4 -phenanthryl, 9-phenanthryl groups and the like.
- the aralkyl group includes an aralkyl group having a substituent.
- substituents include halogen atoms, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, nitro groups, and cyano groups.
- Specific examples include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl, 2-propylphenylmethyl, 4-isopropylphenylmethyl, 4-isobutylphenylmethyl, ⁇ -naphthylmethyl group and the like.
- Q in formula (1) is not particularly limited as long as it is a divalent group having 3 to 30 carbon atoms and having a ring structure.
- the ring structure may be an aromatic ring structure or an alicyclic structure.
- the above Q preferably represents at least one selected from the group represented by formulas (2) to (13).
- R 1 to R 92 above each independently represent a hydrogen atom, a halogen atom, a carboxy group, a sulfo group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or a halogen atom having 1 to 10 carbon atoms.
- R 93 and R 94 each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- W 1 and W 2 are each independently a single bond
- CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom, a C 1-10 alkyl group (provided that these may form a ring), or represents a halogenated alkyl group having 1 to 10 carbon atoms.
- C ⁇ O, O, S, SO, SO 2 , or NR 97 R 97 is represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group).
- Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
- alkyl group and the alkoxy group the same groups as the alkyl group and the alkoxy group in R and R' can be mentioned.
- the halogenated alkyl group having 1 to 10 carbon atoms is obtained by substituting at least one hydrogen atom in the alkyl group having 1 to 10 carbon atoms with a halogen atom, and specific examples thereof include trifluoromethyl , 2,2,2-trifluoroethyl, perfluoroethyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,3,3-tetrafluoropropyl , 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, perfluoropropyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, 2,2 , 3,3,4,4,4-heptafluorobutyl, perfluorobutyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, 2,2,3,3,4 , 4,5,5-octafluoropenty
- X 1 and X 2 each independently represent a single bond, an alkylene group having 1 to 10 carbon atoms, or a group represented by formula (14).
- the structures of these alkyl groups, halogenated alkyl groups, alkoxy groups, and alkylene groups are not particularly limited, and may be, for example, linear, branched, cyclic, or combinations of two or more thereof.
- R 98 to R 101 each independently represent a hydrogen atom, a halogen atom, a carboxy group, a sulfo group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or a represents 10 alkoxy groups
- Y 1 and Y 2 independently represent a single bond or an alkylene group having 1 to 10 carbon atoms.
- halogen atoms, alkyl groups, halogenated alkyl groups and alkoxy groups include the same halogen atoms, alkyl groups, halogenated alkyl groups and alkoxy groups for R 1 to R 92 .
- alkylene groups having 1 to 10 carbon atoms include methylene, ethylene, propylene, trimethylene, tetramethylene and pentamethylene groups.
- the structure of the alkylene group is not particularly limited, and may be linear, branched, cyclic, or a combination of two or more thereof.
- R 1 to R 92 and R 98 to R 101 are a hydrogen atom, a halogen atom, a sulfo group, an alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, or a An alkoxy group of 1 to 5 is preferred, and a hydrogen atom is more preferred.
- A is preferably at least one represented by formulas (2) and (5) to (13), and formulas (2), (5), (7), (8), (11) to (13) ) is more preferred.
- Specific examples of the divalent groups represented by the above formulas (2) to (13) include, but are not limited to, those represented by the following formulas.
- Ph represents a phenyl group. * represents a bond.
- Q is more preferably a divalent group represented by the following formula, since a polymer with a higher refractive index can be obtained.
- Ph represents a phenyl group. * represents a bond.
- Q is preferably an m-phenylene group represented by formula (18).
- Q in formula (1) represents at least one selected from the group represented by formulas (102) to (115), for example. * represents a bond.
- R 1 and R 2 above independently represent an optionally branched alkylene group having 1 to 5 carbon atoms.
- alkylene group examples include methylene, ethylene, propylene, trimethylene, tetramethylene, and pentamethylene groups. is preferred, and an alkylene group having 1 to 2 carbon atoms, more preferably a methylene or ethylene group, most preferably a methylene group.
- the triazine ring-containing polymer of the present invention has at least one triazine ring terminal, and at least part of the triazine ring terminal is capped with an amino group having a fluorine atom-containing group. It is preferable because it has excellent solubility in organic solvents. It is generally known that introduction of a fluorine atom into a compound tends to lower its refractive index. Maintains a high refractive index.
- an organic solvent with low dissolving power such as a low polar solvent or a hydrophobic solvent can be used. Since the composition can be prepared, a thin film can be formed without problems even on a substrate that is easily corroded by a highly polar solvent.
- An amino group having a fluorine atom-containing group has, for example, an arylene group which is a fluorine atom-containing group, and the fluorine atom-containing group is bonded to the amino group via the arylene group.
- Such an amino group is hereinafter referred to as a fluorine atom-containing arylamino group.
- a phenylene group is preferred as the arylene group.
- a fluorine atom-containing arylamino group is an arylamino group having a fluorine atom-containing group. And the fluorine atom-containing group is bonded to the aryl group.
- the fluorine atom-containing group includes a fluorine atom, a fluorine atom-containing hydrocarbon group such as a fluoroalkyl group, and the like, and a fluorine atom and a fluoroalkyl group having 1 to 10 carbon atoms are preferable.
- the fluoroalkyl group having 1 to 10 carbon atoms is not particularly limited, and may be linear, branched, cyclic, or a combination of two or more thereof.
- a perfluoroalkyl group having 1 to 10 carbon atoms is preferable, and a perfluoroalkyl group having 1 to 5 carbon atoms is particularly preferable.
- a fluoroalkyl group is more preferred, and a trifluoromethyl group is most suitable.
- the number of fluorine atom-containing groups is not particularly limited, and can be any number that can be substituted on the aryl group. One is preferred, one to two is more preferred, and one is even more preferred.
- Suitable fluorine-containing arylamino groups include those of formula (15), particularly those of formula (16) having a fluorine-containing group para-positioned to the amino group or a fluorine-atom meta-positioned to the amino group. Those represented by (17) having a containing group are preferred.
- R 102 represents a fluorine atom or a fluoroalkyl group having 1 to 10 carbon atoms. * represents a bond.
- R 102 has the same meaning as above. * represents a bond.
- fluorine atom-containing arylamino groups include, but are not limited to, those represented by the following formulas.
- the fluorine atom-containing arylamino group can be introduced using the corresponding fluorine atom-containing arylamino compound in the production method described below.
- Specific examples of fluorine atom-containing arylamino compounds include 4-fluoroaniline, 4-trifluoromethylaniline, 4-pentafluoroethylaniline and the like.
- triazine ring-containing polymers include those containing repeating units represented by formulas (19) to (22).
- R 1 to R 4 and R102 have the same meanings as above.
- R 102 has the same meaning as above.
- R 102 has the same meaning as above.
- the weight average molecular weight of the polymer in the present invention is not particularly limited, but is preferably 500 to 500,000, more preferably 500 to 100,000, to further improve heat resistance and reduce shrinkage. From the point of view, 2,000 or more is preferable, and from the viewpoint of further increasing the solubility and reducing the viscosity of the obtained composition, it is preferably 50,000 or less, more preferably 30,000 or less, and 10,000 or less. is even more preferred.
- the weight average molecular weight in the present invention is the average molecular weight obtained by standard polystyrene conversion by gel permeation chromatography (hereinafter referred to as GPC) analysis.
- the triazine ring-containing polymer (hyperbranched polymer) of the present invention can be produced according to the method disclosed in International Publication No. 2010/128661 mentioned above. That is, after reacting a trihalogenated triazine compound and an aryldiamino compound in an organic solvent, for example, reacting with a fluorine atom-containing arylamino compound, which is a terminal blocker, the triazine ring-containing polymer of the present invention is obtained. can be obtained.
- a triazine ring-containing polymer (23) can be obtained by reacting a triazine compound (24) and an aryldiamino compound (25) in a suitable organic solvent.
- triazine ring-containing polymer (21) is obtained by reacting triazine compound (24) and aryldiamino compound (25) in a suitable organic solvent, followed by It can be obtained by reacting with a fluorine atom-containing aniline compound (26), which is a terminal blocking agent.
- X independently represents a halogen atom, and R a represents a fluorine atom-containing group.
- the charging ratio of the aryldiamino compound (25) is arbitrary as long as the desired polymer can be obtained. ) is preferably 0.01 to 10 equivalents, more preferably 0.7 to 5 equivalents.
- the aryldiamino compound (25) may be added neat or in the form of a solution dissolved in an organic solvent, but the latter method is preferred in consideration of ease of operation and ease of control of the reaction. .
- the reaction temperature may be appropriately set within the range from the melting point to the boiling point of the solvent used, preferably about -30 to 150°C, more preferably -10 to 100°C.
- organic solvent various solvents commonly used in this type of reaction can be used, such as tetrahydrofuran (THF), dioxane, dimethylsulfoxide; methylurea, hexamethylphosphoramide, N,N-dimethylacetamide, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, N-methyl-2-piperidone, N, N'-dimethylethylene urea, N,N,N',N'-tetramethylmalonic acid amide, N-methylcaprolactam, N-acetylpyrrolidine, N,N-diethylacetamide, N-ethyl-2-pyrrolidone, N, Amide solvents such as N-dimethylpropionic acid amide, N,N-dimethylisobutyramide, N-methylformamide, N,N'-dimethylpropylene urea, and mixed solvents thereof can be used.
- THF t
- N,N-dimethylformamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, N,N-dimethylacetamide, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, and mixtures thereof are preferred, and N,N-dimethylacetamide, N-methyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide are particularly preferred. is.
- various bases that are commonly used during or after polymerization may be added.
- this base include potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, oxide calcium, barium hydroxide, trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, ammonia, n-propylamine, trimethylamine, triethylamine, diisopropylamine, diisopropylethylamine, N-methylpiperidine, 2,2,6,6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, N-methylmorpholine, 2-aminoethanol, ethyldiethanolamine, diethylaminoethanol and the like.
- the amount of the base to be added is preferably 1 to 100 equivalents, more preferably 1 to 10 equivalents, relative to 1 equivalent of the triazine compound (30).
- These bases may be used in the form of an aqueous solution. Although it is preferable that no raw material components remain in the resulting polymer, some of the raw materials may remain as long as the effects of the present invention are not impaired. After completion of the reaction, the product can be easily purified by a reprecipitation method or the like.
- a known method may be adopted as a method for terminal capping using a fluorine atom-containing aniline compound.
- the total amount of the terminal blocker used is preferably about 0.05 to 10 equivalents, preferably 0.1 to 5 equivalents, relative to 1 equivalent of halogen atoms derived from the excess triazine compound not used in the polymerization reaction. More preferably, 0.5 to 2 equivalents is even more preferred.
- the reaction solvent and reaction temperature the same conditions as those described in the reaction of the first step in Scheme 2 above can be mentioned, and the terminal blocking agent may be charged simultaneously with the aryldiamino compound (25).
- an arylamino compound having no substituent may be used and the terminal may be blocked with three or more groups. Examples of the aryl group of the arylamino compound having no substituent include those mentioned above.
- an arylamino compound having a specific heteroatom-containing substituent may be used alone or in combination with another terminal blocking agent for terminal blocking.
- the refractive index of the resulting film can be further increased by end capping with an arylamino group having a specific heteroatom-containing substituent.
- Particular heteroatom-containing substituents include cyano groups, alkylamino groups, arylamino groups, nitro groups, alkylmercapto groups, arylmercapto groups, alkoxycarbonyl groups, alkoxycarbonyloxy groups.
- the arylamino group having a specific heteroatom-containing substituent includes those represented by the following formula (34).
- Y represents a cyano group, an alkylamino group, an arylamino group, a nitro group, an alkylmercapto group, an arylmercapto group, an alkoxycarbonyl group or an alkoxycarbonyloxy group.
- m represents an integer of 1 to 5; When m is 2 or more, Y may be the same or different. * represents a bond.
- Y is preferably a cyano group or a nitro group.
- m is preferably 1.
- Y is preferably substituted at the para- or meta-position.
- the content of the triazine ring-containing polymer in the film-forming composition is not particularly limited, but is preferably 1 to 50% by mass, more preferably 5 to 20% by mass.
- crosslinking agent is not particularly limited as long as it is a compound having at least two crosslinkable groups.
- examples of such compounds include melamine-based compounds having cross-linking substituents such as methylol groups and methoxymethyl groups (e.g., phenoplast compounds, aminoplast compounds, etc.), substituted urea-based compounds, cross-linking groups such as epoxy groups and oxetane groups.
- Compounds containing forming substituents e.g., polyfunctional epoxy compounds, polyfunctional oxetane compounds, etc.
- compounds containing blocked isocyanate groups compounds having acid anhydride groups, compounds having (meth)acrylic groups, and the like.
- compounds containing epoxy groups, blocked isocyanate groups, and (meth)acrylic groups are preferable.
- compounds containing blocked isocyanate groups and photocurable without the use of initiators are preferable.
- a polyfunctional epoxy compound and/or a polyfunctional (meth)acrylic compound, which gives a composition having a high molecular weight, are preferred.
- the polyfunctional epoxy compound is not particularly limited as long as it has two or more epoxy groups in one molecule. Specific examples thereof include tris(2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4-(epoxyethyl) cyclohexane, glycerol triglycidyl ether, and diethylene glycol diglycidyl.
- YH-434 and YH434L manufactured by Nippon Steel Chemical & Materials Co., Ltd.
- Epolead GT-401 which is an epoxy resin having a cyclohexene oxide structure.
- the polyfunctional (meth)acrylic compound is not particularly limited as long as it has two or more (meth)acrylic groups in one molecule.
- Specific examples include ethylene glycol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, ethoxylated trimethylolpropane triacrylate, ethoxylated Trimethylolpropane trimethacrylate, ethoxylated glycerin triacrylate, ethoxylated glycerin trimethacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetramethacrylate, ethoxylated dipentaerythritol hexaacrylate, polyglycerin monoethylene oxide polyacrylate, polygly
- the polyfunctional (meth) acrylic compound is available as a commercial product, specific examples thereof include NK Ester A-200, A-400, A-600, A-1000, A- 9300 (tris(2-acryloyloxyethyl) isocyanurate), A-9300-1CL, A-TMPT, UA-53H, 1G, 2G, 3G, 4G, 9G, 14G, 23G, ABE-300, A-BPE-4, A-BPE-6, A-BPE-10, A-BPE-20, A-BPE-30, BPE-80N, BPE- 100N, BPE-200, BPE-500, BPE-900, BPE-1300N, A-GLY-3E, A-GLY-9E, A-GLY-20E, A-TMPT-3EO, A-TMPT-9EO, AT-20E, ATM-4E, ATM-35E (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD (registered trademark) DPEA-12
- the compound having an acid anhydride group is not particularly limited as long as it is a carboxylic acid anhydride obtained by dehydration condensation of two molecules of carboxylic acid.
- Specific examples thereof include phthalic anhydride and tetrahydrophthalic anhydride. , hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, maleic anhydride, succinic anhydride, octyl succinic anhydride, dodecenyl succinic anhydride, etc.
- the compound containing a blocked isocyanate group has two or more blocked isocyanate groups in one molecule in which the isocyanate group (--NCO) is blocked with an appropriate protective group, and when exposed to a high temperature during thermosetting, It is not particularly limited as long as the protecting group (blocking portion) is thermally dissociated and removed, and the resulting isocyanate group causes a cross-linking reaction. These groups may be the same or may be different from each other).
- Rb represents the organic group of the block portion.
- Such a compound can be obtained, for example, by reacting a compound having two or more isocyanate groups in one molecule with an appropriate blocking agent.
- compounds having two or more isocyanate groups in one molecule include polyisocyanates such as isophorone diisocyanate, 1,6-hexamethylene diisocyanate, methylenebis(4-cyclohexyl isocyanate), trimethylhexamethylene diisocyanate, and dimers thereof. , trimers, and reaction products thereof with diols, triols, diamines, or triamines.
- blocking agents include alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N,N-dimethylaminoethanol, 2-ethoxyethanol and cyclohexanol; phenol, o-nitrophenol , p-chlorophenol, o-, m- or p-cresol, etc.; lactams, such as ⁇ -caprolactam; Pyrazoles such as pyrazole, 3,5-dimethylpyrazole and 3-methylpyrazole; Thiols such as dodecanethiol and benzenethiol.
- alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N,N-dimethylaminoethanol, 2-ethoxyethanol and cyclohexanol
- Compounds containing a blocked isocyanate group are also available as commercial products, and specific examples thereof include Takenate (registered trademark) B-830, B-815N, B-842N, B-870N, B-874N, B-882N, B-7005, B-7030, B-7075, B-5010 (manufactured by Mitsui Chemicals, Inc.), Duranate (registered trademark) 17B-60PX, TPA-B80E, MF-B60X, MF-K60X, E402-B80T (manufactured by Asahi Kasei Corporation), Karenz MOI-BM (registered trademark) (manufactured by Showa Denko K.K.), TRIXENE (registered trademark) BI-7950, BI-7951, BI-7960, BI-7961, BI-7963, BI-7982, BI-7991, BI-7992 (manufactured by Baxenden chemicals LTD) and the like
- the aminoplast compound is not particularly limited as long as it has two or more methoxymethyl groups in one molecule.
- Cymel series such as tetramethoxymethylbenzoguanamine 1123 (manufactured by Nippon Cytec Industries Co., Ltd.), methylated melamine resin Nicalac (registered trademark) MW-30HM, MW-390, MW-100LM, the same Melamine compounds such as Nicalac series such as MX-750LM and methylated urea resins such as MX-270, MX-280 and MX-290 (manufactured by Sanwa Chemical Co., Ltd.).
- the polyfunctional oxetane compound is not particularly limited as long as it has two or more oxetanyl groups in one molecule. (above, manufactured by Toagosei Co., Ltd.) and the like.
- a phenoplast compound has two or more hydroxymethyl groups in one molecule, and when exposed to a high temperature during thermosetting, a cross-linking reaction proceeds between the phenoplast compounds by a dehydration condensation reaction.
- phenoplast compounds include 2,6-dihydroxymethyl-4-methylphenol, 2,4-dihydroxymethyl-6-methylphenol, bis(2-hydroxy-3-hydroxymethyl-5-methylphenyl)methane, Bis(4-hydroxy-3-hydroxymethyl-5-methylphenyl)methane, 2,2-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane, bis(3-formyl-4-hydroxyphenyl)methane , bis(4-hydroxy-2,5-dimethylphenyl)formylmethane, ⁇ , ⁇ -bis(4-hydroxy-2,5-dimethylphenyl)-4-formyltoluene, and the like.
- Phenoplast compounds are also commercially available, and specific examples thereof include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, and BI25X-DF. , BI25X-TPA (manufactured by Asahi Organic Chemicals Industry Co., Ltd.) and the like.
- a polyfunctional (meth)acrylic compound is preferable because it can suppress a decrease in refractive index due to incorporation of a cross-linking agent and the curing reaction proceeds rapidly.
- Polyfunctional (meth)acrylic compounds having the following isocyanuric acid skeleton are more preferable because of their excellent compatibility. Examples of polyfunctional (meth)acrylic compounds having such a skeleton include NK Ester A-9300 and NK Ester A-9300-1CL (both manufactured by Shin-Nakamura Chemical Co., Ltd.).
- R 111 to R 113 are each independently a monovalent organic group having at least one (meth)acrylic group at the end.
- the resulting cured film is preferably liquid at 25 ° C. and has a viscosity of 5,000 mPa s or less.
- Such low-viscosity cross-linking agents are also available as commercial products. -9E (95mPa s, 25°C), A-GLY-20E (200mPa s, 25°C), A-TMPT-3EO (60mPa s, 25°C), A-TMPT-9EO, ATM -4E (150 mPa s, 25 ° C.), ATM-35E (350 mPa s, 25 ° C.) (above, manufactured by Shin-Nakamura Chemical Co., Ltd.), etc.
- the chain length between (meth) acrylic groups is relatively Long crosslinkers are included.
- NK Ester A-GLY-20E manufactured by Shin-Nakamura Chemical Co., Ltd.
- ATM-35E manufactured by Shin-Nakamura Chemical Co., Ltd.
- a thin film comprising the triazine ring-containing polymer of the present invention is laminated on a protective film such as PET or polyolefin film, and light is irradiated through the protective film, even the thin film laminated film can be cured satisfactorily without being inhibited by oxygen. You can get sex.
- the protective film since the protective film needs to be peeled off after curing, it is preferable to use a polybasic acid-modified acrylic oligomer that gives a thin film with good peelability.
- the above-mentioned cross-linking agents may be used alone or in combination of two or more.
- the content of the cross-linking agent in the film-forming composition is preferably 1 to 500 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer, but considering the control of the refractive index, it is preferably 50 to 300 parts by mass. parts, more preferably 100 to 150 parts by mass.
- Inorganic Fine Particles Inorganic fine particles have hydrophilic groups and crosslinkable groups on their surfaces. Inorganic fine particles having a hydrophilic group and a crosslinkable group on the surface (hereinafter sometimes referred to as "surface-modified inorganic fine particles") are, for example, an organic silicon It is obtained by modifying the surface of the core particles with a compound and an organosilicon compound having a crosslinkable group. By using surface-modified inorganic fine particles, the solvent resistance can be further improved as compared with the case of using simple inorganic fine particles.
- Organosilicon compounds have hydrolyzable groups that generate Si—OH groups upon hydrolysis. Hydrolyzable groups include, for example, silicon-bonded alkoxy groups and silicon-bonded acetoxy groups. The number of hydrolyzable groups in the organosilicon compound is not particularly limited, but may be 1 to 3, for example.
- hydrophilic groups examples include polyether groups such as polyoxyethylene groups, polyoxypropylene groups, and polyoxybutylene groups.
- organosilicon compounds having a hydrophilic group examples include [methoxy(polyethyleneoxy)n-propyl]trimethoxysilane, [methoxy(polyethyleneoxy)n-propyl]triethoxysilane, [methoxy(polyethyleneoxy)n-propyl ] Tripropoxysilane, [methoxy (polyethyleneoxy) n-propyl] triacetoxysilane, [methoxy (polypropyleneoxy) n-propyl] trimethoxysilane, [methoxy (polypropyleneoxy) n-propyl] triethoxysilane, [methoxy ( polypropyleneoxy)n-propyl]tripropoxysilane, "methoxy(polypropyleneoxy)n-propyl” triacetoxysilane, [methoxy(polybutyleneoxy)n-propyl]trimethoxysilane, [methoxy(polybutyleneoxy)n
- the crosslinkable group is not particularly limited as long as it is a group capable of forming a crosslinked structure by reacting with a crosslinker, and examples thereof include radically polymerizable groups, epoxy groups, and amino groups.
- examples of radically polymerizable groups include allyl groups and (meth)acryloyloxy groups.
- Organosilicon compounds having radically polymerizable groups include, for example, 3-acryloxypropylmethyldimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-acryloxypropylmethyldiethoxysilane, and 3-acryloxypropyltriethoxysilane.
- organosilicon compounds having an epoxy group include 3-glycidoxypropyltrimethoxysilane and 8-glycidoxyoctyltrimethoxysilane.
- organosilicon compounds having an amino group include N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyl triethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, and the like. These may be used individually by 1 type, or may be used in combination of 2 or more type.
- the bonding amount of the organosilicon compound to the surface of the core particles is not particularly limited, but is preferably 0.1 to 30% by mass, more preferably 1 to 15% by mass, relative to the core particles.
- the primary particle size of the surface-modified inorganic fine particles is preferably 20 nm or less from the viewpoints of dispersion stability, refractive index and transparency of the resulting film.
- the secondary particle diameter (according to dynamic light scattering method) of the surface-modified inorganic fine particles is preferably 2 to 100 nm, more preferably 5 to 50 nm, from the viewpoint of dispersion stability, refractive index and transparency of the resulting thin film. ⁇ 20 nm is even more preferred.
- the surface-modified inorganic fine particles are prepared by adding a predetermined amount of an organosilicon compound to an aqueous dispersion of core particles or a dispersion in a hydrophilic organic solvent, hydrolyzing the organosilicon compound with a catalyst such as dilute hydrochloric acid, and treating the surface of the core particles. It can be obtained by binding to
- the aqueous dispersion or hydrophilic organic solvent dispersion of the core particles can be further replaced with a hydrophobic organic solvent.
- This replacement method can be carried out by a conventional method such as a distillation method or an ultrafiltration method.
- hydrophobic solvents include ketones such as methyl ethyl ketone and methyl isobutyl ketone, cyclic ketones such as cyclopentanone and cyclohexanone, and esters such as ethyl acetate and butyl acetate.
- the organic solvent dispersion of the core particles may contain optional components.
- the dispersibility of the core particles can be further improved.
- phosphoric acid derivatives include phenylphosphonic acid and metal salts thereof.
- phosphoric acid-based surfactants include Disperbyk (manufactured by BYK-Chemie), Phosphanol (manufactured by Toho Chemical Industry Co., Ltd.), and Nikkor (manufactured by Nikko Chemicals Co., Ltd.).
- Oxycarboxylic acids include, for example, lactic acid, tartaric acid, citric acid, gluconic acid, malic acid and glycolic acid.
- the content of these optional components is preferably about 30% by mass or less with respect to all metal oxides in the core particles.
- the concentration of the core particles in the organic solvent dispersion is preferably 10 to 60% by mass, more preferably 30 to 50% by mass.
- inorganic fine particles serving as core particles of surface-modified inorganic fine particles include Be, Al, Si, Ti, V, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, It contains oxides, sulfides or nitrides of one or more metals selected from the group consisting of Pb, Bi and Ce, and it is particularly preferable to contain these metal oxides.
- the inorganic fine particles may be used alone or in combination of two or more.
- metal oxides include Al2O3 , ZnO, TiO2 , ZrO2, Fe2O3 , Sb2O5 , BeO , ZnO , SnO2 , CeO2 , SiO2 , and WO3 . are mentioned. It is also effective to use a plurality of metal oxides as a composite oxide.
- a composite oxide is a mixture of two or more kinds of inorganic oxides in the production stage of fine particles.
- composite oxides of TiO 2 and ZrO 2 , composite oxides of TiO 2 , ZrO 2 and SnO 2 , composite oxides of ZrO 2 and SnO 2 and the like can be mentioned. Further, it may be a compound of the above metals.
- Examples include ZnSb 2 O 6 , BaTiO 3 , SrTiO 3 and SrSnO 3 . These compounds can be used alone or in admixture of two or more, and may also be used in admixture with the above oxides.
- the inorganic fine particles serving as the core particles of the surface-modified inorganic fine particles are, for example, third metal oxide particles ( C).
- the first metal oxide particles (A) can be produced by known methods such as ion exchange, deflocculation, hydrolysis, and reaction methods.
- the ion exchange method include at least one metal selected from the group consisting of Ti, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi and Ce. and a method of treating an acid salt of the metal with a hydrogen-type ion exchange resin, or a method of treating a basic salt of the metal with a hydroxyl-type anion exchange resin.
- Examples of deflocculation include washing the gel obtained by neutralizing the acid salt of the metal with a base or neutralizing the basic salt of the metal with an acid, followed by peptization with an acid or a base.
- Examples of the hydrolysis method include a method of hydrolyzing the alkoxide of the above metal, or a method of hydrolyzing the basic salt of the above metal under heating and then removing unnecessary acid.
- Examples of the reaction method include a method of reacting the metal powder with an acid.
- the first metal oxide particles (A) are preferably oxides of metals having a valence of 2 to 6, such as Ti, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta , W, Pb, Bi, Ba, Al, Sr, Hf and Ce.
- metal oxides include, for example, TiO2 , Fe2O3 , CuO , ZnO, Y2O3 , ZrO2 , Nb2O5 , MoO3 , In2O3 , SnO2 , Sb2O5 .
- metal oxides can be used singly or in combination of two or more.
- the method of combining the metal oxides include a method of mixing several types of the metal oxides, a method of compounding the metal oxides, and a method of forming a solid solution of the metal oxides at the atomic level.
- Combinations of the metal oxides include, for example, SnO 2 —TiO 2 composite particles in which SnO 2 particles and TiO 2 particles are chemically bonded at their interfaces, and SnO 2 particles and WO 3 particles.
- 2 composite particles, and TiO 2 --ZrO 2 --SnO 2 composite particles obtained by forming a solid solution of TiO 2 , ZrO 2 and SnO 2 at the atomic level.
- the first metal oxide particles ( A ) can also be used as a compound by combining metal components. ZnO, BaTiO 3 , SrTiO 3 , aluminum-doped zinc oxide, and the like.
- the TiO 2 contained in the particles has any of anatase, rutile, anatase/rutile mixed, and brookite crystal structures.
- those containing the rutile type are preferable in consideration of the refractive index and transparency of the resulting thin film.
- the first metal oxide particles (A) form a thin film layer made of a metal oxide such as zirconium oxide, silicon oxide, and aluminum oxide on the surface from the viewpoint of suppressing the activity (for example, photocatalytic performance).
- the thin film layer can be formed, for example, by adding a zirconium compound to an aqueous dispersion of the first metal oxide particles (A) and heating the mixture at 40 to 200.degree.
- zirconium compound examples include zirconium oxychloride, zirconium chloride, zirconium hydroxide, zirconium sulfate, zirconium nitrate, zirconium oxynitrate, zirconium acetate, zirconyl carbonate, ammonium zirconium carbonate, potassium zirconium carbonate, zirconium ethylhexanoate, and stearic acid.
- the amount of the zirconia compound used, as zirconium oxide, is preferably 3 to 50% by mass relative to the first metal oxide particles (A) used.
- the primary particle size of the first metal oxide particles (A) is preferably 2 to 60 nm, more preferably 2 to 30 nm, from the viewpoints of dispersion stability, refractive index and transparency of the resulting thin film. More preferably, 2 to 20 nm is particularly preferable. From the viewpoint of dispersion stability, refractive index and transparency of the obtained thin film, 5 to 100 nm is preferred, 5 to 50 nm is more preferred, and 5 to 30 nm is particularly preferred.
- the first metal oxide particles (A) can be synthesized, for example, according to the method described in International Publication No. 2013/081136.
- the second metal oxide particles (B) are preferably oxide particles of at least one metal selected from the group consisting of Si, Al, Sn, Zr, Mo, Sb and W.
- the second metal oxide particles (B) are in the form of metal oxides, for example, SiO 2 , Al 2 O 3 , SnO 2 , ZrO 2 , MoO 3 , Sb 2 O 5 , WO 3 and the like. can. And these metal oxides can be used individually by 1 type, and can also be used in combination of 2 or more types. Examples of the method of combining the metal oxides include a method of mixing several types of the metal oxides, a method of compounding the metal oxides, and a method of forming a solid solution of the metal oxides at the atomic level.
- the second metal oxide particles (B) include, for example, SnO 2 —WO 3 composite particles, SnO 2 particles in which SnO 2 particles and WO 3 particles are chemically bonded at their interface to form a composite.
- SnO 2 —WO 3 SiO 2 composite particles produced and composited
- SnO 2 —MoO 3 composited by chemical bonding of SnO 2 particles, MoO 3 particles and SiO 2 particles at their interfaces
- Examples include SiO 2 composite particles, Sb 2 O 5 -SiO 2 composite particles in which Sb 2 O 5 particles and SiO 2 particles are chemically bonded at their interface to form a composite.
- the ratio (mass ratio) of the metal oxides contained is not particularly limited, but for example, SnO 2 —SiO 2 composite
- the particles preferably have a SiO 2 /SnO 2 mass ratio of 0.1 to 5, and the Sb 2 O 5 —SiO 2 composite particles preferably have a Sb 2 O 5 /SiO 2 mass ratio of 0.1 to 5.
- the second metal oxide particles (B) can be produced by known methods such as an ion exchange method and an oxidation method.
- the ion exchange method include a method of treating an acid salt of the above metal with a hydrogen ion exchange resin.
- the oxidation method include a method of reacting the powder of the metal or the oxide of the metal with hydrogen peroxide.
- the primary particle size of the second metal oxide particles (B) is preferably 5 nm or less, more preferably 1 to 5 nm, from the viewpoints of dispersion stability and the refractive index and transparency of the resulting thin film. preferable.
- the third metal oxide particles (C) are metal oxide particles obtained by coating the surfaces of the first metal oxide particles (A) with the second metal oxide particles (B). Examples of the manufacturing method include the following first method and second method.
- an aqueous dispersion containing the first metal oxide particles (A) and an aqueous dispersion containing the second metal oxide particles (B) are separated by (B)/(A).
- the aqueous dispersion is heated.
- An aqueous dispersion of the third metal oxide particles (C) in which the surfaces of the first metal oxide particles (A) are coated with the Sb 2 O 5 —SiO 2 composite particles is obtained.
- an aqueous dispersion containing the first metal oxide particles (A), a water-soluble tin oxide alkali salt and a silicon oxide alkali salt as the second metal oxide particles (B), SnO 2 After mixing so that the mass ratio represented by /SiO 2 (value in terms of metal oxide) is 0.1 to 5, cation exchange is performed to remove alkali metal ions SnO 2 —SiO obtained by 2 and an aqueous dispersion of composite particles so that the mass ratio represented by (B)/(A) (in terms of metal oxide) is 0.05 to 0.5, and then mixed. It is a method of heating an aqueous dispersion.
- an aqueous solution of sodium salt can be preferably used as the aqueous solution of water-soluble alkali salt used in the second method.
- an aqueous solution of sodium salt can be preferably used.
- aqueous dispersion containing the first metal oxide particles (A) and an aqueous solution of sodium stannate and sodium silicate as the second metal oxide particles (B) After mixing an aqueous dispersion containing the first metal oxide particles (A) and an aqueous solution of sodium stannate and sodium silicate as the second metal oxide particles (B), cation exchange is performed to obtain and an aqueous dispersion of SnO 2 —SiO 2 composite particles obtained above are mixed so that the mass ratio is 0.05 to 0.5, and the aqueous dispersion is heated at 70 to 350° C.
- An aqueous dispersion of the third metal oxide particles (C) in which the surface of the metal oxide particles (A) as nuclei is coated with the second metal oxide particles (B) composed of SnO 2 —SiO 2 composite particles. can get.
- the temperature at which the first metal oxide particles (A) and the second metal oxide particles (B) are mixed is usually 1 to 100°C, preferably 20 to 60°C.
- the heating temperature after mixing is preferably 70 to 350°C, more preferably 70 to 150°C.
- the heating time after mixing is usually 10 minutes to 5 hours, preferably 30 minutes to 4 hours.
- the aqueous dispersion of the third metal oxide particles (C) may contain any component.
- oxycarboxylic acids it is possible to further improve performance such as dispersibility of the third metal oxide particles (C).
- the oxycarboxylic acid include lactic acid, tartaric acid, citric acid, gluconic acid, malic acid and glycolic acid.
- the content of the oxycarboxylic acids is preferably about 30% by mass or less with respect to all metal oxides in the third metal oxide particles (C).
- the dispersion of the third metal oxide particles (C) may contain an alkaline component.
- alkali component include alkali metal hydroxides such as Li, Na, K, Rb, and Cs; ammonia; ethylamine, isopropylamine, n-propylamine, n-butylamine, diethylamine, di-n-propylamine, Diisopropylamine, di-n-butylamine, diisobutylamine, triethylamine, tripropylamine, tributylamine, triisobutylamine, triamylamine (tri-n-pentylamine), tri-n-hexylamine, tri-n-octylamine , dimethylpropylamine, dimethylbutylamine, dimethylhexylamine, etc.
- alkali component include alkali metal hydroxides such as Li, Na, K, Rb, and Cs; ammonia; ethylamine,
- alkali component is preferably about 30% by mass or less with respect to all metal oxides in the third metal oxide particles (C). Moreover, these alkali components can be used in combination with the above oxycarboxylic acid.
- the aqueous dispersion of the third metal oxide particles (C) When it is desired to further increase the concentration of the aqueous dispersion of the third metal oxide particles (C), it can be concentrated to a maximum of about 65% by mass by a conventional method.
- the method includes, for example, an evaporation method and an ultrafiltration method.
- the alkali metal hydroxide, amine, quaternary ammonium salt, oxycarboxylic acid, etc. may be added.
- the total metal oxide concentration of the solvent dispersion of the third metal oxide particles (C) is preferably 10 to 60% by mass, more preferably 20 to 50% by mass.
- an organic solvent dispersion of the third metal oxide particles (C) is obtained.
- This substitution can be carried out by an ordinary method such as a distillation method or an ultrafiltration method.
- the hydrophilic organic solvent include lower alcohols such as methanol, ethanol, isopropanol and 1-propanol, ethers such as propylene glycol monomethyl ether, linear amides such as dimethylformamide and N,N'-dimethylacetamide, Cyclic amides such as N-methyl-2-pyrrolidone, glycols such as ethyl cellosolve and ethylene glycol.
- the primary particle size of the third metal oxide particles (C) is preferably 20 nm or less from the viewpoint of dispersion stability and the refractive index and transparency of the resulting film.
- the dynamic light scattering particle diameter (according to the dynamic light scattering method), which is the secondary particle diameter of the third metal oxide particles (C), is determined by 2 to 100 nm is preferred.
- the refractive index of the surface-modified inorganic fine particles is not particularly limited, but is preferably from 1.6 to 2.6, more preferably from 1.8 to 2.6, from the viewpoint of not lowering the refractive index of the resulting film.
- the refractive index of the surface-modified inorganic fine particles can be obtained, for example, by measuring the refractive index of a liquid of the surface-modified inorganic fine particles dispersed in a solvent or resin having a known refractive index with an Abbe refractometer and extrapolating from the value, or by extrapolating from the measured value.
- the refractive index of the film or cured product containing the modified inorganic fine particles is measured with an Abbe refractometer or spectroscopic ellipsometry, and the refractive index can be extrapolated from the measured value.
- the content of the surface-modified inorganic fine particles in the composition may be within a range that does not impair the dispersibility in the final composition obtained. It is possible to control accordingly. For example, it can be added in the range of 0.1 to 1,000 parts by mass, preferably 1 to 500 parts by mass, with respect to 100 parts by mass of the triazine ring-containing polymer. And from the viewpoint of obtaining solvent resistance, it is more preferably 10 to 300 parts by mass.
- Organic Solvents include toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, styrene, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol, propylene glycol monoethyl ether, Ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, propylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, dipropylene Glycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene
- glycol ester solvents such as ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol monobutyl ether acetate, and diethylene glycol monoethyl ether acetate;
- Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol; ethyl acetate, methyl acetate, butyl acetate, methoxybutyl acetate, cellosolve acetate, amyl acetate, n-propyl acetate, Since it dissolves well in ester solvents such as isopropyl acetate, methyl lactate, ethyl lactate and butyl lactate, it is particularly suitable for forming
- the solid content concentration in the composition is not particularly limited as long as it does not affect storage stability, and may be appropriately set according to the thickness of the desired film. Specifically, from the viewpoint of solubility and storage stability, the solid content concentration is preferably 0.1 to 50% by mass, more preferably 0.1 to 40% by mass.
- An initiator suitable for each cross-linking agent can also be added to the composition of the present invention.
- a polyfunctional epoxy compound and/or a polyfunctional (meth)acrylic compound is used as a cross-linking agent, photocuring proceeds to give a cured film without using an initiator.
- an initiator may be used.
- a photoacid generator or a photobase generator can be used.
- the photoacid generator may be appropriately selected from known ones and used.
- onium salt derivatives such as diazonium salts, sulfonium salts and iodonium salts can be used.
- aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, and 4-methylphenyldiazonium hexafluorophosphate; diphenyliodonium hexafluoroantimonate, bis(4-methylphenyl) diaryliodonium salts such as iodonium hexafluorophosphate, bis(4-tert-butylphenyl)iodonium hexafluorophosphate; triphenylsulfonium hexafluoroantimonate, tris(4-methoxyphenyl)sulfonium hexafluorophosphate, diphenyl-4-thiophenoxy phenylsulfonium hexafluoroantimonate, diphenyl-4-thiophenoxyphenylsulfonium hex
- onium salts may be commercially available products, and specific examples include San-Aid SI-60, SI-80, SI-100, SI-60L, SI-80L, SI-100L, SI-L145, SI- L150, SI-L160, SI-L110, SI-L147 (manufactured by Sanshin Chemical Industry Co., Ltd.), UVI-6950, UVI-6970, UVI-6974, UVI-6990, UVI-6992 (manufactured by Union Carbide company), CPI-100P, CPI-100A, CPI-200K, CPI-200S (manufactured by San-Apro Co., Ltd.), Adeka Optomer SP-150, SP-151, SP-170, SP-171 (manufactured by San-Apro Co., Ltd.) Asahi Denka Kogyo Co., Ltd.), Irgacure 261 (BASF), CI-2481, CI-2624, CI-2639, CI-2064
- the photobase generator it may be appropriately selected from known ones and used. etc. can be used. Specific examples include 2-nitrobenzylcyclohexylcarbamate, triphenylmethanol, O-carbamoylhydroxylamide, O-carbamoyloxime, [[(2,6-dinitrobenzyl)oxy]carbonyl]cyclohexylamine, bis[[(2 -nitrobenzyl)oxy]carbonyl]hexane 1,6-diamine, 4-(methylthiobenzoyl)-1-methyl-1-morpholinoethane, (4-morpholinobenzoyl)-1-benzyl-1-dimethylaminopropane, N- (2-nitrobenzyloxycarbonyl)pyrrolidine, hexaamminecobalt (III) tris(triphenylmethylborate), 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, 2,6-dimethyl
- a photoacid or base generator When a photoacid or base generator is used, it is preferably used in the range of 0.1 to 15 parts by mass, more preferably in the range of 1 to 10 parts by mass, per 100 parts by mass of the polyfunctional epoxy compound. If necessary, an epoxy resin curing agent may be blended in an amount of 1 to 100 parts by mass with respect to 100 parts by mass of the polyfunctional epoxy compound.
- a photoradical polymerization initiator when using a polyfunctional (meth)acrylic compound, a photoradical polymerization initiator can be used.
- the radical photopolymerization initiator it may be appropriately selected and used from known ones. is mentioned.
- a photocleavable photoradical polymerization initiator is preferred.
- the photo-cleavable photoradical polymerization initiator is described in Latest UV Curing Techniques (page 159, published by: Kazuhiro Takasusu, published by: Technical Information Institute, 1991).
- radical photopolymerization initiators include, for example, BASF trade name: Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI1700, CGI1750, CGI1850 , CG24-61, OXE01, OXE02, Darocure 1116, 1173, MBF, manufactured by BASF Product name: Lucilin TPO, manufactured by UCB Product name: Ebecryl P36, manufactured by Fratetzuri Lamberti Product name: Ezacure KIP150, KIP65LT, KIP100F, KT37, KT55, KTO46, KIP75/B and the like.
- BASF trade name Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI1700, CGI1750, CGI1850 , CG24-61, OXE01
- a photoradical polymerization initiator When using a photoradical polymerization initiator, it is preferable to use it in the range of 0.1 to 200 parts by weight with respect to 100 parts by weight of the polyfunctional (meth) acrylate compound, and to use it in the range of 1 to 150 parts by weight. is more preferred.
- composition of the present invention may be added with a polyfunctional thiol compound having two or more mercapto groups in the molecule for the purpose of promoting the reaction between the triazine ring-containing polymer and the cross-linking agent. good.
- a polyfunctional thiol compound represented by the following formula is preferred.
- the above L represents a divalent to tetravalent organic group, preferably a divalent to tetravalent aliphatic group having 2 to 12 carbon atoms or a divalent to tetravalent heterocyclic ring-containing group, and a divalent to tetravalent carbon number of 2
- An aliphatic group of ⁇ 8 or a trivalent group having an isocyanuric acid skeleton (1,3,5-triazine-2,4,6(1H,3H,5H)-trione ring) represented by the following formula is more preferable.
- n represents an integer of 2 to 4 corresponding to the valence of L.
- Specific compounds include 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4 , 6-(1H,3H,5H)-trione, pentaerythritol tetrakis (3-mercaptobutyrate), trimethylolpropane tris (3-mercaptobutyrate), trimethylolethane tris (3-mercaptobutyrate) and the like. be done.
- polyfunctional thiol compounds are also commercially available, and examples thereof include Karenz MT-BD1, Karenz MT NR1, Karenz MT PE1, TPMB, and TEMB (manufactured by Showa Denko KK). These polyfunctional thiol compounds may be used singly or in combination of two or more.
- the amount added is not particularly limited as long as it does not adversely affect the resulting thin film, but in the present invention, the solid content of 100% by mass, 0.01 to 10 mass % is preferable, and 0.03 to 6% by mass is more preferable.
- composition of the present invention may contain other components other than the triazine ring-containing polymer, the cross-linking agent, the inorganic fine particles and the organic solvent, such as leveling agents, surfactants and silane coupling agents, as long as they do not impair the effects of the present invention. Additives such as agents may also be included.
- surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol; Polyoxyethylene alkylallyl ethers such as ethers; polyoxyethylene/polyoxypropylene block copolymers; sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate sorbitan fatty acid esters such as; Nonionic surfactants such as sorbitan fatty acid esters, trade names Ftop EF301, EF303, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.
- surfactants may be used alone or in combination of two or more.
- the amount of the surfactant used is preferably 0.0001 to 5 parts by mass, more preferably 0.001 to 1 part by mass, and 0.01 to 0.5 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. Even more preferable.
- the film-forming composition of the present invention can be applied to a substrate, then heated as necessary to evaporate the solvent, and then heated or irradiated with light to form a desired cured film.
- Any method can be used to apply the composition, and examples thereof include spin coating, dipping, flow coating, inkjet, jet dispenser, spraying, bar coating, gravure coating, slit coating, roll coating, and transfer. Methods such as printing, brush coating, blade coating, and air knife coating can be used.
- the base material silicon, glass on which indium tin oxide (ITO) is formed, glass on which indium zinc oxide (IZO) is formed, metal nanowires, polyethylene terephthalate (PET), plastic, glass, A base material made of quartz, ceramics, or the like can be mentioned, and a flexible base material having flexibility can also be used.
- the calcination temperature is not particularly limited for the purpose of evaporating the solvent, and can be performed at, for example, 110 to 400°C.
- the baking method is not particularly limited. For example, a hot plate or an oven may be used to evaporate under an appropriate atmosphere such as air, an inert gas such as nitrogen, or vacuum.
- the sintering temperature and sintering time may be selected in accordance with the process steps of the target electronic device, and the sintering conditions may be selected such that the physical properties of the obtained film are suitable for the required characteristics of the electronic device.
- the conditions for light irradiation are not particularly limited either, and suitable irradiation energy and time may be adopted according to the triazine ring-containing polymer and cross-linking agent to be used.
- the thin film and cured film of the present invention obtained as described above can achieve high heat resistance, high refractive index, and low volume shrinkage.
- a component used in manufacturing touch panels, optical semiconductor (LED) elements, solid-state imaging elements, organic thin-film solar cells, dye-sensitized solar cells, organic thin-film transistors (TFT), lenses, prism cameras, binoculars, microscopes, semiconductor exposure devices, etc. etc. can be suitably used in the fields of electronic devices and optical materials.
- the thin film and cured film produced from the composition of the present invention have high transparency and a high refractive index. light diffusion efficiency) can be improved, and the durability can be improved.
- composition of the present invention when used in the light scattering layer of an organic EL element, as the light diffusing agent, a known organic/inorganic composite light diffusing agent, organic light diffusing agent, or inorganic light diffusing agent can be used. not to be These may be used alone, may be used in combination of two or more of the same type, or may be used in combination of two or more of different types.
- organic-inorganic composite light diffusing agent examples include melamine resin/silica composite particles.
- organic light diffusing agents include crosslinked polymethylmethacrylate (PMMA) particles, crosslinked polymethylacrylate particles, crosslinked polystyrene particles, crosslinked styrene-acrylic copolymer particles, melamine-formaldehyde particles, silicone resin particles, silica-acrylic composite particles, and nylon particles.
- PMMA polymethylmethacrylate
- benzoguanamine-formaldehyde particles benzoguanamine/melamine/formaldehyde particles, fluorine resin particles, epoxy resin particles, polyphenylene sulfide resin particles, polyethersulfone resin particles, polyacrylonitrile particles, polyurethane particles, and the like.
- inorganic light diffusing agents examples include calcium carbonate (CaCO 3 ), titanium oxide (TiO 2 ), barium sulfate (BaSO 4 ), aluminum hydroxide (Al(OH) 3 ), silica (SiO 2 ), and talc.
- titanium oxide (TiO 2 ) and agglomerated silica particles are preferable, and non-aggregated titanium oxide (TiO 2 ) is more preferable, from the viewpoint of further increasing the light diffusibility of the resulting cured film.
- These light diffusing agents may be used after being surface-treated with an appropriate surface modifier.
- 1,3-Phenylenediamine [6] (211.12 g, 1.952 mol, manufactured by Amino-Chem) and 399.97 g of dimethylacetamide (DMAc, manufactured by Kanto Chemical Co., Ltd.) were placed in a 5,000 mL four-necked flask.
- DMAc dimethylacetamide
- 1,3-phenylenediamine [6] was dissolved in DMAc by stirring. Then, it is cooled to ⁇ 10° C. in an ethanol-dry ice bath, and 2,4,6-trichloro-1,3,5-triazine [1] (360.00 g, 1.952 mol, manufactured by Tokyo Chemical Industry Co., Ltd.).
- Compound P-2 had a weight average molecular weight Mw of 5,280 and a polydispersity Mw/Mn of 2.7 as measured by GPC in terms of polystyrene.
- Compound P-2 (3.0 g), propylene glycol monomethyl ether (hereinafter abbreviated as PGME) (7.0 g), propylene glycol monomethyl ether acetate (hereinafter abbreviated as PGMEA) (7.0 g), cyclopentanone ( hereinafter abbreviated as CPN) (7.0 g), it dissolved in any solvent, and a uniform varnish of 30% by mass was obtained.
- PGME propylene glycol monomethyl ether
- PGMEA propylene glycol monomethyl ether acetate
- CPN cyclopentanone
- Production Example 1 Production of First Metal Oxide Particles (Nuclear Particles) (A1) Put 126.2 g of pure water in a 1-liter container, add 17.8 g of metastannic acid (contains 15 g in terms of SnO2, Showa Kako Co., Ltd.) ), titanium tetraisopropoxide 284 g (contains 80 g in terms of TiO2 , manufactured by Nippon Soda Co., Ltd.
- oxalic acid dihydrate 98 (contains 70 g in terms of oxalic acid, manufactured by Ube Industries, Ltd.)
- 438 g of a 35% by mass tetraethylammonium hydroxide aqueous solution (manufactured by Seichem Japan) was added with stirring.
- the resulting mixed solution had a molar ratio of oxalic acid/titanium atoms of 0.78 and a molar ratio of tetraethylammonium hydroxide/titanium atoms of 1.04.
- 950 g of the mixed solution was held at 80° C. for 2 hours, and further reduced to 580 Torr and held for 2 hours to prepare a titanium mixed solution.
- the titanium mixed solution after preparation had a pH of 4.7, an electrical conductivity of 27.2 mS/cm, and a metal oxide concentration of 10.0% by mass.
- 950 g of the titanium mixed solution and 950 g of pure water were charged into a 3-liter glass-lined autoclave container, and hydrothermally treated at 140° C. for 5 hours. After cooling to room temperature, the hydrothermally treated solution taken out was an aqueous dispersion of pale milky white titanium oxide-containing colloidal particles.
- the resulting dispersion had a pH of 3.9, a conductivity of 19.7 mS/cm, a TiO2 concentration of 4.2 wt%, a tetraethylammonium hydroxide concentration of 8.0 wt%, an oxalic acid concentration of 3.7 wt%, a dynamic Oval particles with a primary particle diameter of 5 to 15 nm were observed by light scattering method particle diameter 16 nm and transmission electron microscope observation.
- the obtained dispersion was dried at 110° C. and the powder was subjected to X-ray diffraction analysis to confirm that it was a rutile crystal.
- the obtained colloidal particles containing titanium oxide were used as core particles (A).
- zirconium oxychloride containing 21.19% by mass as ZrO2, manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd.
- ZrO2 manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd.
- aqueous zirconium oxychloride solution 3 as ZrO2
- first metal oxide particles (A1)) having a thin film layer of zirconium oxide formed on the surface thereof is hydrolyzed by heating to 95°C. was gotten.
- the resulting water-dispersed sol had a pH of 1.2 and a total metal oxide concentration of 20% by mass, and colloidal particles having a primary particle diameter of 4 to 8 nm were observed by transmission electron microscope observation.
- Second Metal Oxide Particles (B1) 77.2 g of JIS No. 3 sodium silicate (containing 29.8% by mass of SiO 2 , manufactured by Fuji Chemical Co., Ltd.) was dissolved in 1,282 g of pure water, Then, 20.9 g of sodium stannate NaSnO 3 .H 2 O (contains 55.1% by mass as SnO 2 , manufactured by Showa Kako Co., Ltd.) was dissolved. The resulting aqueous solution is passed through a column filled with a hydrogen-type cation exchange resin (Amberlite (registered trademark) IR-120B) to obtain a water-dispersed sol of acidic silicon dioxide-stannic oxide composite colloidal particles (B1).
- a hydrogen-type cation exchange resin Amberlite (registered trademark) IR-120B
- Production Example 3 Production of Third Metal Oxide Particles (C1) 1,455 g of the water-dispersed sol of the first metal oxide particles (A1) obtained in Production Example 1 was prepared in Production Example 2 as the second metal oxide. It was added to 2,634 g of the water-dispersed sol of particles (B1) under stirring. Then, the solution was passed through a column packed with 500 ml of an anion exchange resin (Amberlite (registered trademark) IRA-410, manufactured by Organo Co., Ltd.). Next, after heating the water-dispersed sol after passing the liquid at 95 ° C.
- an anion exchange resin Amberlite (registered trademark) IRA-410, manufactured by Organo Co., Ltd.
- the liquid was passed through a column packed with a hydrogen-type cation exchange resin (Amberlite (registered trademark) IR-120B), and tri-n-pentyl Stabilized with amine and concentrated by an ultrafiltration membrane method, an intermediate thin film layer made of zirconium oxide is formed between the first metal oxide particles (A1) and the second metal oxide particles (B1).
- a water-dispersed sol of silicon dioxide-stannic oxide composite oxide-coated titanium oxide-containing colloidal particles (C1) (hereinafter referred to as third metal oxide particles (C1)) was obtained.
- the resulting water-dispersed sol had a total metal oxide concentration of 20% by mass, and a primary particle size of this sol was 4 to 10 nm when observed with a transmission electron microscope.
- the dispersion medium of the resulting water-dispersed sol was replaced with methanol using a rotary evaporator to obtain a methanol-dispersed sol of the third metal oxide particles (C1).
- This methanol-dispersed sol had a total metal oxide concentration of 30% by mass, a viscosity of 1.5 mPa ⁇ s, a particle diameter of 18 nm as determined by the dynamic light scattering method, and a water content of 1.0% by mass.
- Production Example 4 Production of surface-modified inorganic fine particles (D1) To 533 g of the methanol-dispersed sol of the third metal oxide particles (C1) obtained in Production Example 3, polyether-modified silane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name :X-12-641) was added, and heated under reflux at 70°C for 5 hours. Then, 6.4 g of 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-503) was added and heated under reflux at 70° C. for 5 hours to hydrolyze the polyether-modified silane.
- a methanol dispersion of surface-modified colloidal particles (D1) (hereinafter referred to as surface-modified metal oxide particles (D1)) having surface-bonded 3-methacryloxypropyltrimethoxysilane hydrolysates was obtained.
- D1 surface-modified colloidal particles
- D1 surface-modified metal oxide particles
- methanol is replaced with propylene glycol monomethyl ether to obtain a propylene glycol monomethyl ether dispersion of surface-modified metal oxide particles (D1). 530 g of was obtained.
- the resulting dispersion has a specific gravity of 1.209, a viscosity of 3.6 mPa s, a total metal oxide concentration of 30.0% by mass, a primary particle diameter of 5 to 10 nm as observed by a transmission electron microscope, and dynamic light scattering particles. The diameter was 11 nm.
- the hydrolyzate of the polyether-modified silane bound to the surface of the third metal oxide particles (C1) is the total metal content of the third metal oxide particles (C1).
- Table 1 shows the refractive index and film thickness of the cured film prepared in Reference Example 1-1 above.
- the thin film produced using the polymer compound obtained in Synthesis Example 1-1 has a refractive index exceeding 1.64 while improving the solubility in organic solvents. .
- This SP-2 solution was spin-coated on a non-alkali glass substrate of 50 mm ⁇ 50 mm ⁇ 0.7 mm with a spin coater at 200 rpm for 5 seconds and 1,000 rpm for 30 seconds, and using a hot plate at 100 ° C. for 1 minute. After temporary drying, a cured film (hereinafter referred to as SP-2 film) was obtained by irradiating light with a wavelength of 365 nm and an exposure amount of 300 mJ/cm 2 with a UV irradiation device.
- SP-2 film a cured film
- S-2 solution a varnish having a solid content of 40% by mass was prepared (hereinafter referred to as S-2 film). Using this S-2 solution, a cured film (hereinafter referred to as S-2 film) was obtained in the same manner as in Example 1-1.
- the cured film obtained above was measured for refractive index, film thickness, b * , transmittance at 400 to 800 nm, and HAZE. The results are shown in Table 2 and FIG. Regarding the transmittance, the average transmittance from 400 to 800 nm was calculated and shown in the table.
- the cured film produced using the polymer compound obtained in Synthesis Example 1-1 maintains a high refractive index, and has an excellent effect of improving b * , HAZE reduction and transmittance. I understand.
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Abstract
Description
求められる具体的な特性としては、1)耐熱性、2)透明性、3)高屈折率、4)高溶解性、5)低体積収縮率、6)高温高湿耐性、7)高膜硬度などが挙げられる。
この点に鑑み、本出願人は、トリアジン環および芳香環を有する繰り返し単位を含む重合体が高屈折率を有し、ポリマー単独で高耐熱性、高透明性、高屈折率、高溶解性、低体積収縮を達成でき、電子デバイスを作製する際の膜形成用組成物として好適であることを既に見出している(特許文献1)。
また、塗布装置を用いて高屈折ポリマーを含む膜形成用組成物を塗布した後に、装置のライン洗浄溶媒として低極性溶媒等が用いられることがあり、そのような溶媒に対する溶解性が低いポリマーであると、ラインが目詰まりしてしまうという問題が生じることもあった。さらに、電子デバイスの製造時において薄膜が溶剤に暴露される際、条件によっては作製した薄膜にクラックが発生することがあり、その耐久性についてもさらなる改善が求められている。
[1] 下記式(1)で表される繰り返し単位構造を含み、少なくとも1つのトリアジン環末端を有するトリアジン環含有重合体と、
架橋剤と、
表面に親水性基および架橋性基を有する無機微粒子と、
有機溶媒と、
を含むことを特徴とする膜形成用組成物。
[2] 前記式(1)中のQが、式(2)~(13)及び式(102)~(115)で示される群から選ばれる少なくとも1種を表す、[1]に記載の膜形成用組成物。
R93およびR94は、水素原子または炭素数1~10のアルキル基を表し、
W1およびW2は、互いに独立して、単結合、CR95R96(R95およびR96は、互いに独立して、水素原子、炭素数1~10のアルキル基(ただし、これらは一緒になって環を形成していてもよい。)、または炭素数1~10のハロゲン化アルキル基を表す。)、C=O、O、S、SO、SO2、またはNR97(R97は、水素原子、炭素数1~10のアルキル基またはフェニル基を表す。)を表し、
X1およびX2は、互いに独立して、単結合、炭素数1~10のアルキレン基、または式(14)
Y1およびY2は、互いに独立して、単結合または炭素数1~10のアルキレン基を表す。)で示される基を表す。
*は結合手を表す。〕
[3] 前記式(2)~(13)における前記R1~R92およびR98~R101が、水素原子である[2]に記載の膜形成用組成物。
[4] 前記架橋剤が、多官能(メタ)アクリル化合物である[1]~[3]のいずれかに記載の膜形成用組成物。
[5] 前記親水性基が、ポリエーテル基である[1]~[4]のいずれかに記載の膜形成用組成物。
[6] 前記架橋性基が、ラジカル重合性基である[1]~[5]のいずれかに記載の膜形成用組成物。
[7] 前記無機微粒子が、金属酸化物、金属硫黄物または金属窒化物を含む[1]~[6]のいずれかに記載の膜形成用組成物。
[8] 前記トリアジン環末端の少なくとも一部が、フッ素原子含有基を有するアミノ基で封止されている、[1]~[7]のいずれかに記載の膜形成用組成物。
[9] 前記フッ素原子含有基を有するアミノ基が、式(15)で示される[8]に記載の膜形成用組成物。
[10] 前記フッ素原子含有基を有するアミノ基が、式(16)または(17)で示される[9]に記載の膜形成用組成物。
[11] 前記R102が、炭素数1~10のパーフルオロアルキル基である[9]又は[10]に記載の膜形成用組成物。
[12] 前記式(1)中のQが、式(18)で示される[1]~[11]のいずれかに記載の膜形成用組成物。
[13] 前記有機溶媒が、グリコールエステル系溶媒、ケトン系溶媒、およびエステル系溶媒から選ばれる少なくとも1種を含む[1]~[12]のいずれかに記載の膜形成用組成物。
[14] [1]~[13]のいずれかに記載の膜形成用組成物から得られる薄膜。
[15] 基材と、前記基材上に形成された[14]に記載の薄膜とを備える電子デバイス。
[16] 基材と、前記基材上に形成された[14]に記載の薄膜とを備える光学部材。
本発明の膜形成用組成物から作製された薄膜は、高耐熱性、高屈折率、低体積収縮、耐溶剤性(耐クラック性)という特性を発揮し得るため、液晶ディスプレイ、有機EL素子(有機ELディスプレイや有機EL照明)、タッチパネル、光半導体素子、固体撮像素子、有機薄膜太陽電池、色素増感太陽電池、有機薄膜トランジスタ、レンズ、プリズム、カメラ、双眼鏡、顕微鏡、半導体露光装置等を作製する際の一部材など、電子デバイスや光学材料の分野に好適に利用できる。
特に、本発明の膜形成用組成物から作製された薄膜は透明性が高く、屈折率や耐溶剤性(耐クラック性)も高いため、有機EL照明の平坦化層や光散乱層として使用することで、その光取出し効率(光拡散効率)を改善することができるとともに、その耐久性を改善することができる。
本発明に係る膜形成用組成物は、トリアジン環含有重合体と、架橋剤と、無機微粒子と、有機溶媒とを含む。
トリアジン環含有重合体は、下記式(1)で表される繰り返し単位構造を含むものである。
トリアジン環含有重合体は、例えば、いわゆるハイパーブランチポリマーである。ハイパーブランチポリマーとは、不規則な分岐構造を有する高分岐ポリマーである。ここでの不規則とは、規則的な分岐構造を有する高分岐ポリマーであるデンドリマーの分岐構造よりも不規則であることを意味する。
例えば、ハイパーブランチポリマーであるトリアジン環含有重合体は、式(1)で表される繰り返し単位構造よりも大きな構造として、式(1)で表される繰り返し単位構造の3つの結合手のそれぞれに、式(1)で表される繰り返し単位構造が結合してなる構造(構造X)を含む。ハイパーブランチポリマーであるトリアジン環含有重合体においては、構造Xがトリアジン環含有重合体の末端を除く全体に分布している。
ハイパーブランチポリマーであるトリアジン環含有重合体においては、繰り返し単位構造が、本質的に式(1)で表される繰り返し単位構造のみからであってもよい。
上記式中、RおよびR’は、互いに独立して、水素原子、アルキル基、アルコキシ基、アリール基、またはアラルキル基を表すが、屈折率をより高めるという観点から、ともに水素原子であることが好ましい。
本発明において、アルキル基の炭素数としては特に限定されるものではないが、1~20が好ましく、ポリマーの耐熱性をより高めることを考慮すると、アルキル基の炭素数としては、1~10がより好ましく、1~3がより一層好ましい。また、アルキル基の構造は、特に限定されず、例えば、直鎖状、分岐状、環状、およびこれらの2以上の組み合わせのいずれでもよい。
本発明において上記アリール基には、置換基を有するアリール基が含まれる。置換基としては、例えば、ハロゲン原子、炭素数1~6のアルキル基、炭素数1~6のアルコキシ基、ニトロ基、シアノ基などが挙げられる。
アリール基の具体例としては、フェニル、o-クロルフェニル、m-クロルフェニル、p-クロルフェニル、o-フルオロフェニル、p-フルオロフェニル、o-メトキシフェニル、p-メトキシフェニル、p-ニトロフェニル、p-シアノフェニル、α-ナフチル、β-ナフチル、o-ビフェニリル、m-ビフェニリル、p-ビフェニリル、1-アントリル、2-アントリル、9-アントリル、1-フェナントリル、2-フェナントリル、3-フェナントリル、4-フェナントリル、9-フェナントリル基等が挙げられる。
本発明において、アラルキル基には、置換基を有するアラルキル基が含まれる。置換基としては、例えば、ハロゲン原子、炭素数1~6のアルキル基、炭素数1~6のアルコキシ基、ニトロ基、シアノ基などが挙げられる。
その具体例としては、ベンジル、p-メチルフェニルメチル、m-メチルフェニルメチル、o-エチルフェニルメチル、m-エチルフェニルメチル、p-エチルフェニルメチル、2-プロピルフェニルメチル、4-イソプロピルフェニルメチル、4-イソブチルフェニルメチル、α-ナフチルメチル基等が挙げられる。
式(1)中のQとしては、環構造を有する炭素数3~30の2価の基であれば特に限定されるものではない。
環構造は、芳香族環構造であってもよいし、脂環構造であってもよい。
R93およびR94は、水素原子または炭素数1~10のアルキル基を表し、
W1およびW2は、互いに独立して、単結合、CR95R96(R95およびR96は、互いに独立して、水素原子、炭素数1~10のアルキル基(ただし、これらは一緒になって環を形成していてもよい。)、または炭素数1~10のハロゲン化アルキル基を表す。)、C=O、O、S、SO、SO2、またはNR97(R97は、水素原子、炭素数1~10のアルキル基またはフェニル基を表す。)を表す。
なお、アルキル基、アルコキシ基としては、R,R’におけるアルキル基、アルコキシ基と同様のものが挙げられる。
これらのアルキル基、ハロゲン化アルキル基、アルコキシ基、及びアルキレン基の構造は、特に限定されず、例えば、直鎖状、分岐状、環状、およびこれらの2以上の組み合わせのいずれでもよい。
炭素数1~10のアルキレン基としては、メチレン、エチレン、プロピレン、トリメチレン、テトラメチレン、ペンタメチレン基等が挙げられる。
上記アルキレン基の構造は、特に限定されず、例えば、直鎖状、分岐状、環状、およびこれらの2以上の組み合わせのいずれでもよい。
このようなアルキレン基としては、メチレン、エチレン、プロピレン、トリメチレン、テトラメチレン、ペンタメチレン基等が挙げられるが、得られるポリマーの屈折率をより高めるということを考慮すると、炭素数1~3のアルキレン基が好ましく、炭素数1~2のアルキレン基、具体的には、メチレン、エチレン基がより好ましく、メチレン基が最適である。
また、本発明のトリアジン環含有重合体は、少なくとも1つのトリアジン環末端を有し、このトリアジン環末端の少なくとも一部が、フッ素原子含有基を有するアミノ基で封止されていることが、各種有機溶剤に対する溶解性に優れる点で好ましい。
一般的に、化合物にフッ素原子を導入することで、その屈折率は低下する傾向にあることが知られているが、本発明のトリアジン環含有重合体は、フッ素原子が導入されていても、高い屈折率を維持している。
トリアジン環末端の少なくとも一部がフッ素原子含有基を有するアミノ基で封止されているトリアジン環含有重合体を用いることで、低極性溶媒、疎水性溶媒等の溶解力が低い有機溶媒を用いて組成物を調製できるため、高極性溶媒に浸食され易い基材上にも問題なく薄膜を形成することができる。
アリーレン基としては、フェニレン基が好ましい。
フッ素原子含有基としては、フッ素原子、フルオロアルキル基等のフッ素原子含有炭化水素基などが挙げられるが、フッ素原子、炭素数1~10のフルオロアルキル基が好ましい。
炭素数1~10のフルオロアルキル基としては、特に限定されず、例えば、直鎖、分岐、環状、およびこれらの2以上の組み合わせのいずれでもよく、例えば、トリフルオロメチル、ペンタフルオロエチル、2,2,2-トリフルオロエチル、ヘプタフルオロプロピル、2,2,3,3,3-ペンタフルオロプロピル、2,2,3,3-テトラフルオロプロピル、2,2,2-トリフルオロ-1-(トリフルオロメチル)エチル、ノナフルオロブチル、4,4,4-トリフルオロブチル、ウンデカフルオロペンチル、2,2,3,3,4,4,5,5,5-ノナフルオロペンチル、2,2,3,3,4,4,5,5-オクタフルオロペンチル、トリデカフルオロヘキシル、2,2,3,3,4,4,5,5,6,6,6-ウンデカフルオロヘキシル、2,2,3,3,4,4,5,5,6,6-デカフルオロヘキシル、3,3,4,4,5,5,6,6,6-ノナフルオロヘキシル基等が挙げられる。
フッ素原子含有アリールアミノ化合物の具体例としては、4-フルオロアニリン、4-トリフルオロメチルアニリン、4-ペンタフルオロエチルアニリン等が挙げられる。
なお、本発明における重量平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、GPCという)分析による標準ポリスチレン換算で得られる平均分子量である。
すなわち、トリハロゲン化トリアジン化合物とアリールジアミノ化合物とを有機溶媒中で反応させた後、例えば、末端封止剤である、フッ素原子含有アリールアミノ化合物と反応させることにより本発明のトリアジン環含有重合体を得ることができる。
アリールジアミノ化合物(25)は、ニートで加えても、有機溶媒に溶かした溶液で加えてもよいが、操作の容易さや反応のコントロールのし易さなどを考慮すると、後者の手法が好適である。
反応温度は、用いる溶媒の融点から溶媒の沸点までの範囲で適宜設定すればよいが、-30~150℃程度が好ましく、-10~100℃がより好ましい。
中でもN,N-ジメチルホルムアミド、ジメチルスルホキシド、N-メチル-2-ピロリドン、N,N-ジメチルアセトアミド、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、およびそれらの混合系が好ましく、特に、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドン、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミドが好適である。
この塩基の具体例としては、炭酸カリウム、水酸化カリウム、炭酸ナトリウム、水酸化ナトリウム、炭酸水素ナトリウム、ナトリウムエトキシド、酢酸ナトリウム、炭酸リチウム、水酸化リチウム、酸化リチウム、酢酸カリウム、酸化マグネシウム、酸化カルシウム、水酸化バリウム、リン酸三リチウム、リン酸三ナトリウム、リン酸三カリウム、フッ化セシウム、酸化アルミニウム、アンモニア、n-プロピルアミン、トリメチルアミン、トリエチルアミン、ジイソプロピルアミン、ジイソプロピルエチルアミン、N-メチルピペリジン、2,2,6,6-テトラメチル-N-メチルピペリジン、ピリジン、4-ジメチルアミノピリジン、N-メチルモルホリン、2-アミノエタノール、エチルジエタノールアミン、ジエチルアミノエタノール等が挙げられる。
塩基の添加量は、トリアジン化合物(30)1当量に対して1~100当量が好ましく、1~10当量がより好ましい。なお、これらの塩基は水溶液にして用いてもよい。
得られる重合体には、原料成分が残存していないことが好ましいが、本発明の効果を損なわなければ一部の原料が残存していてもよい。
反応終了後、生成物は再沈法等によって容易に精製できる。
この場合、末端封止剤の合計使用量は、重合反応に使われなかった余剰のトリアジン化合物由来のハロゲン原子1当量に対し、0.05~10当量程度が好ましく、0.1~5当量がより好ましく、0.5~2当量がより一層好ましい。
反応溶媒や反応温度としては、上記スキーム2の1段階目の反応で述べたのと同様の条件が挙げられ、また、末端封止剤は、アリールジアミノ化合物(25)と同時に仕込んでもよい。
なお、置換基を有しないアリールアミノ化合物を用い、3種類以上の基で末端封止を行ってもよい。この置換基を有しないアリールアミノ化合物のアリール基としては上記と同様のものが挙げられる。
特定のヘテロ原子含有置換基としては、シアノ基、アルキルアミノ基、アリールアミノ基、ニトロ基、アルキルメルカプト基、アリールメルカプト基、アルコキシカルボニル基、アルコキシカルボニルオキシ基が挙げられる。
特定のヘテロ原子含有置換基を有するアリールアミノ基としては、下記式(34)で示されるものが挙げられる。
架橋剤としては、少なくとも2個の架橋性基を有する化合物であれば特に限定されるものではない。
そのような化合物としては、メチロール基、メトキシメチル基などの架橋形成置換基を有するメラミン系化合物(例えば、フェノプラスト化合物、アミノプラスト化合物など)、置換尿素系化合物、エポキシ基またはオキセタン基などの架橋形成置換基を含有する化合物(例えば、多官能エポキシ化合物、多官能オキセタン化合物など)、ブロックイソシアナート基を含有する化合物、酸無水物基を有する化合物、(メタ)アクリル基を有する化合物等が挙げられるが、耐熱性や保存安定性の観点からエポキシ基、ブロックイソシアネート基、(メタ)アクリル基を含有する化合物が好ましく、特に、ブロックイソシアネート基を有する化合物や、開始剤を用いなくとも光硬化可能な組成物を与える多官能エポキシ化合物および/または多官能(メタ)アクリル化合物が好ましい。
その具体例としては、トリス(2,3-エポキシプロピル)イソシアヌレート、1,4-ブタンジオールジグリシジルエーテル、1,2-エポキシ-4-(エポキシエチル)シクロヘキサン、グリセロールトリグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、2,6-ジグリシジルフェニルグリシジルエーテル、1,1,3-トリス[p-(2,3-エポキシプロポキシ)フェニル]プロパン、1,2-シクロヘキサンジカルボン酸ジグリシジルエステル、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、トリメチロールエタントリグリシジルエーテル、ビスフェノール-A-ジグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル等が挙げられる。
その具体例としては、エチレングリコールジアクリレート、エチレングリコールジメタクリレート、ポリエチレングリコールジアクリレート、ポリエチレングリコールジメタクリレート、エトキシ化ビスフェノールAジアクリレート、エトキシ化ビスフェノールAジメタクリレート、エトキシ化トリメチロールプロパントリアクリレート、エトキシ化トリメチロールプロパントリメタクリレート、エトキシ化グリセリントリアクリレート、エトキシ化グリセリントリメタクリレート、エトキシ化ペンタエリスリトールテトラアクリレート、エトキシ化ペンタエリスリトールテトラメタクリレート、エトキシ化ジペンタエリスリトールヘキサアクリレート、ポリグリセリンモノエチレンオキサイドポリアクリレート、ポリグリセリンポリエチレングリコールポリアクリレート、ジペンタエリスリトールヘキサアクリレート、ジペンタエリスリトールヘキサメタクリレート、ネオペンチルグリコールジアクリレート、ネオペンチルグリコールジメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールプロパントリアクリレート、トリメチロールプロパントリメタクリレート、トリシクロデカンジメタノールジアクリレート、トリシクロデカンジメタノールジメタクリレート、1,6-ヘキサンジオールジアクリレート、1,6-ヘキサンジオールジメタクリレート、多塩基酸変性アクリルオリゴマー等が挙げられる。
上記多塩基酸変性アクリルオリゴマーも市販品として入手が可能であり、その具体例としては、アロニックスM-510,520(以上、東亞合成(株)製)等が挙げられる。
一分子中2個以上のイソシアネート基を有する化合物としては、例えば、イソホロンジイソシアネート、1,6-ヘキサメチレンジイソシアネート、メチレンビス(4-シクロヘキシルイソシアネート)、トリメチルヘキサメチレンジイソシアネートのポリイソシアネートや、これらの二量体、三量体、および、これらとジオール類、トリオール類、ジアミン類、またはトリアミン類との反応物などが挙げられる。
ブロック剤としては、例えば、メタノール、エタノール、イソプロパノール、n-ブタノール、2-エトキシヘキサノール、2-N,N-ジメチルアミノエタノール、2-エトキシエタノール、シクロヘキサノール等のアルコール類;フェノール、o-ニトロフェノール、p-クロロフェノール、o-、m-またはp-クレゾール等のフェノール類;ε-カプロラクタム等のラクタム類、アセトンオキシム、メチルエチルケトンオキシム、メチルイソブチルケトンオキシム、シクロヘキサノンオキシム、アセトフェノンオキシム、ベンゾフェノンオキシム等のオキシム類;ピラゾール、3,5-ジメチルピラゾール、3-メチルピラゾール等のピラゾール類;ドデカンチオール、ベンゼンチオール等のチオール類などが挙げられる。
多官能オキセタン化合物としては、オキセタニル基を一分子中2個以上有するものであれば、特に限定されるものではなく、例えば、オキセタニル基を含有するOXT-221、OX-SQ-H、OX-SC(以上、東亜合成(株)製)等が挙げられる。
フェノプラスト化合物としては、例えば、2,6-ジヒドロキシメチル-4-メチルフェノール、2,4-ジヒドロキシメチル-6-メチルフェノール、ビス(2-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン、ビス(4-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン、2,2-ビス(4-ヒドロキシ-3,5-ジヒドロキシメチルフェニル)プロパン、ビス(3-ホルミル-4-ヒドロキシフェニル)メタン、ビス(4-ヒドロキシ-2,5-ジメチルフェニル)ホルミルメタン、α,α-ビス(4-ヒドロキシ-2,5-ジメチルフェニル)-4-ホルミルトルエン等が挙げられる。
フェノプラスト化合物は、市販品としても入手が可能であり、その具体例としては、26DMPC、46DMOC、DM-BIPC-F、DM-BIOC-F、TM-BIP-A、BISA-F、BI25X-DF、BI25X-TPA(以上、旭有機材工業(株)製)等が挙げられる。
このような骨格を有する多官能(メタ)アクリル化合物としては、例えば、NKエステルA-9300、同A-9300-1CL(いずれも、新中村化学工業(株)製)が挙げられる。
このような低粘度架橋剤も市販品として入手可能であり、例えば、上述した多官能(メタ)アクリル化合物のうち、NKエステルA-GLY-3E(85mPa・s,25℃)、同A-GLY-9E(95mPa・s,25℃)、同A-GLY-20E(200mPa・s,25℃)、同A-TMPT-3EO(60mPa・s,25℃)、同A-TMPT-9EO、同ATM-4E(150mPa・s,25℃)、同ATM-35E(350mPa・s,25℃)(以上、新中村化学工業(株)製)等の、(メタ)アクリル基間の鎖長が比較的長い架橋剤が挙げられる。
膜形成用組成物における架橋剤の含有量は、トリアジン環含有重合体100質量部に対して、1~500質量部が好ましいが、屈折率をコントロールすることを考慮すると、好ましくは50~300質量部、より好ましくは100~150質量部である。
無機微粒子は、その表面に親水性基および架橋性基を有する。
表面に親水性基および架橋性基を有する無機微粒子(以下、「表面修飾無機微粒子」と称することがある。)は、例えば、未修飾の無機微粒子を核粒子とし、親水性基を有する有機ケイ素化合物および架橋性基を有する有機ケイ素化合物で核粒子の表面を修飾することにより得られる。
表面修飾無機微粒子を用いることで、単なる無機微粒子を用いた場合と比較して耐溶剤性を更に優れたものにできる。
有機ケイ素化合物は、加水分解によりSi-OH基を生成する加水分解性基を有する。加水分解性基としては、例えば、ケイ素原子に結合したアルコキシ基、ケイ素原子に結合したアセトキシ基などが挙げられる。有機ケイ素化合物における加水分解基の数としては、特に限定されないが、例えば、1~3個が挙げられる。
ラジカル重合性基としては、例えば、アリル基、(メタ)アクリロイルオキシ基などが挙げられる。
エポキシ基を有する有機ケイ素化合物としては、例えば、3-グリシドキシプロピルトリメトキシシラン、8-グリシドキシオクチルトリメトキシシランなどが挙げられる。
アミノ基を有する有機ケイ素化合物としては、例えば、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、3-トリエトキシシリル-N-(1,3-ジメチル-ブチリデン)プロピルアミンなどが挙げられる。
これらは、1種を単独で用いても、2種以上を組み合せて用いてもよい。
表面修飾無機微粒子の二次粒子径(動的光散乱法による)は、分散安定性、得られる薄膜の屈折率および透明性の点から、2~100nmが好ましく、5~50nmがより好ましく、5~20nmがより一層好ましい。
金属酸化物の具体例としては、例えば、Al2O3、ZnO、TiO2、ZrO2、Fe2O3、Sb2O5、BeO、ZnO、SnO2、CeO2、SiO2、WO3などが挙げられる。
また、複数の金属酸化物を複合酸化物として用いることも有効である。複合酸化物とは、微粒子の製造段階で2種以上の無機酸化物を混合させたものである。例えば、TiO2とZrO2との複合酸化物、TiO2とZrO2とSnO2との複合酸化物、ZrO2とSnO2との複合酸化物などが挙げられる。
さらに、上記金属の化合物であってもよい。例えば、ZnSb2O6、BaTiO3、SrTiO3、SrSnO3などが挙げられる。これらの化合物は、単独でまたは2種以上を混合して用いることができ、さらに上記の酸化物と混合して用いてもよい。
第1金属酸化物粒子(A)の二次粒子径である動的光散乱法粒子径(動的光散乱法による)は、分散安定性、得られる薄膜の屈折率および透明性の点から、5~100nmが好ましく、5~50nmがより好ましく、5~30nmが特に好ましい。
第3金属酸化物粒子(C)の溶媒分散液の全金属酸化物濃度は、好ましくは10~60質量%であり、より好ましくは20~50質量%である。
第3金属酸化物粒子(C)の二次粒子径である動的光散乱法粒子径(動的光散乱法による)は、分散安定性、得られる薄膜の屈折率および透明性の点から、2~100nmが好ましい。
有機溶媒としては、例えば、トルエン、p-キシレン、o-キシレン、m-キシレン、エチルベンゼン、スチレン、エチレングリコールジメチルエーテル、プロピレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテル、プロピレングリコール、プロピレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールジメチルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールジエチルエーテル、ジプロピレングリコールモノメチルエーテル、ジエチレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジエチレングリコールモノエチルエーテル、トリエチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコール、1-オクタノール、エチレングリコール、ヘキシレングリコール、トリメチレングリコール、1-メトキシ-2-ブタノール、シクロヘキサノール、ジアセトンアルコール、フルフリルアルコール、テトラヒドロフルフリルアルコール、プロピレングリコール、ベンジルアルコール、1,3-ブタンジオール、1,4-ブタンジオール、2,3-ブタンジオール、γ-ブチロラクトン、アセトン、メチルエチルケトン、メチルイソプロピルケトン、ジエチルケトン、メチルイソブチルケトン、メチルn-ブチルケトン、シクロペンタノン、シクロヘキサノン、酢酸エチル、酢酸イソプロピル、酢酸n-プロピル、酢酸イソブチル、酢酸n-ブチル、乳酸エチル、メタノール、エタノール、イソプロパノール、tert-ブタノール、アリルアルコール、n-プロパノール、2-メチル-2-ブタノール、イソブタノール、n-ブタノール、2-メチル-1-ブタノール、1-ペンタノール、2-メチル-1-ペンタノール、2-エチルヘキサノール、1-メトキシ-2-プロパノール、テトラヒドロフラン、1,4-ジオキサン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド(DMAc)、N-メチル-2-ピロリドン、1,3-ジメチル-2-イミダゾリジノン、ジメチルスルホキシド、N-シクロヘキシル-2-ピロリジノン等が挙げられ、これらは単独で用いても、2種以上混合して用いてもよい。
光酸発生剤としては、公知のものから適宜選択して用いればよく、例えば、ジアゾニウム塩、スルホニウム塩やヨードニウム塩などのオニウム塩誘導体を用いることができる。
その具体例としては、フェニルジアゾニウムヘキサフルオロホスフェート、4-メトキシフェニルジアゾニウムヘキサフルオロアンチモネート、4-メチルフェニルジアゾニウムヘキサフルオロホスフェート等のアリールジアゾニウム塩;ジフェニルヨードニウムヘキサフルオロアンチモネート、ビス(4-メチルフェニル)ヨードニウムヘキサフルオロホスフェート、ビス(4-tert-ブチルフェニル)ヨードニウムヘキサフルオロホスフェート等のジアリールヨードニウム塩;トリフェニルスルホニウムヘキサフルオロアンチモネート、トリス(4-メトキシフェニル)スルホニウムヘキサフルオロホスフェート、ジフェニル-4-チオフェノキシフェニルスルホニウムヘキサフルオロアンチモネート、ジフェニル-4-チオフェノキシフェニルスルホニウムヘキサフルオロホスフェート、4,4’-ビス(ジフェニルスルフォニオ)フェニルスルフィド-ビスヘキサフルオロアンチモネート、4,4’-ビス(ジフェニルスルフォニオ)フェニルスルフィド-ビスヘキサフルオロホスフェート、4,4’-ビス[ジ(β-ヒドロキシエトキシ)フェニルスルホニオ]フェニルスルフィド-ビスヘキサフルオロアンチモネート、4,4’-ビス[ジ(β-ヒドロキシエトキシ)フェニルスルホニオ]フェニルスルフィド-ビス-ヘキサフルオロホスフェート、4-[4’-(ベンゾイル)フェニルチオ]フェニル-ジ(4-フルオロフェニル)スルホニウムヘキサフルオロアンチモネート、4-[4’-(ベンゾイル)フェニルチオ]フェニル-ビス(4-フルオロフェニル)スルホニウムヘキサフルオロホスフェート等のトリアリールスルホニウム塩等が挙げられる。
その具体例としては、2-ニトロベンジルシクロヘキシルカルバメート、トリフェニルメタノール、O-カルバモイルヒドロキシルアミド、O-カルバモイルオキシム、[[(2,6-ジニトロベンジル)オキシ]カルボニル]シクロヘキシルアミン、ビス[[(2-ニトロベンジル)オキシ]カルボニル]ヘキサン1,6-ジアミン、4-(メチルチオベンゾイル)-1-メチル-1-モルホリノエタン、(4-モルホリノベンゾイル)-1-ベンジル-1-ジメチルアミノプロパン、N-(2-ニトロベンジルオキシカルボニル)ピロリジン、ヘキサアンミンコバルト(III)トリス(トリフェニルメチルボレート)、2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-ブタノン、2,6-ジメチル-3,5-ジアセチル-4-(2’-ニトロフェニル)-1,4-ジヒドロピリジン、2,6-ジメチル-3,5-ジアセチル-4-(2’,4’-ジニトロフェニル)-1,4-ジヒドロピリジン等が挙げられる。
また、光塩基発生剤は市販品を用いてもよく、その具体例としては、TPS-OH、NBC-101、ANC-101(いずれも製品名、みどり化学(株)製)等が挙げられる。
なお、必要に応じてエポキシ樹脂硬化剤を、多官能エポキシ化合物100質量部に対して、1~100質量部の量で配合してもよい。
光ラジカル重合開始剤としても、公知のものから適宜選択して用いればよく、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、オキシムエステル類、テトラメチルチウラムモノサルファイドおよびチオキサントン類等が挙げられる。
特に、光開裂型の光ラジカル重合開始剤が好ましい。光開裂型の光ラジカル重合開始剤については、最新UV硬化技術(159頁、発行人:高薄一弘、発行所:(株)技術情報協会、1991年発行)に記載されている。
市販の光ラジカル重合開始剤としては、例えば、BASF社製 商品名:イルガキュア 127、184、369、379、379EG、651、500、754、819、903、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、OXE01、OXE02、ダロキュア 1116、1173、MBF、BASF社製 商品名:ルシリン TPO、UCB社製 商品名:エベクリル P36、フラテツリ・ランベルティ社製 商品名:エザキュアー KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等が挙げられる。
光ラジカル重合開始剤を用いる場合、多官能(メタ)アクリレート化合物100質量部に対して、0.1~200質量部の範囲で使用することが好ましく、1~150質量部の範囲で使用することがより好ましい。
具体的には、下記式で示される多官能チオール化合物が好ましい。
上記nは、Lの価数に対応して2~4の整数を表す。
これらの多官能チオール化合物は、市販品として入手することもでき、例えば、カレンズMT-BD1、カレンズMT NR1、カレンズMT PE1、TPMB、TEMB(以上、昭和電工(株)製)等が挙げられる。
これらの多官能チオール化合物は、1種単独で用いても、2種以上組み合わせて用いてもよい。
界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類;ポリオキシエチレンオクチルフェノールエーテル、ポリオキシエチレンノニルフェノールエーテル等のポリオキシエチレンアルキルアリルエーテル類;ポリオキシエチレン・ポリオキシプロピレンブロックコポリマー類;ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類;ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、商品名エフトップEF301、EF303、EF352(三菱マテリアル電子化成(株)製(旧(株)ジェムコ製))、商品名メガファックF171、F173、R-08、R-30、R-40、F-553、F-554、RS-75、RS-72-K(DIC(株)製)、フロラードFC430、FC431(住友スリーエム(株)製)、商品名アサヒガードAG710,サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(AGC(株)製)等のフッ素系界面活性剤、オルガノシロキサンポリマーKP341(信越化学工業(株)製)、BYK-302、BYK-307、BYK-322、BYK-323、BYK-330、BYK-333、BYK-370、BYK-375、BYK-378(ビックケミー・ジャパン(株)製)等が挙げられる。
組成物の塗布方法は任意であり、例えば、スピンコート法、ディップ法、フローコート法、インクジェット法、ジェットディスペンサー法、スプレー法、バーコート法、グラビアコート法、スリットコート法、ロールコート法、転写印刷法、刷毛塗り、ブレードコート法、エアーナイフコート法等の方法を採用できる。
焼成温度は、溶媒を蒸発させる目的では特に限定されず、例えば110~400℃で行うことができる。
焼成方法としては、特に限定されるものではなく、例えば、ホットプレートやオーブンを用いて、大気、窒素等の不活性ガス、真空中等の適切な雰囲気下で蒸発させればよい。
焼成温度および焼成時間は、目的とする電子デバイスのプロセス工程に適合した条件を選択すればよく、得られる膜の物性値が電子デバイスの要求特性に適合するような焼成条件を選択すればよい。
光照射する場合の条件も特に限定されるものではなく、用いるトリアジン環含有重合体および架橋剤に応じて、適宜な照射エネルギーおよび時間を採用すればよい。
特に、本発明の組成物から作製された薄膜や硬化膜は、透明性が高く、屈折率も高いため、有機EL照明の平坦化膜や光散乱層として用いた場合に、その光取出し効率(光拡散効率)を改善することができるとともに、その耐久性を改善することができる。
有機光拡散剤としては、架橋ポリメチルメタクリレート(PMMA)粒子、架橋ポリメチルアクリレート粒子、架橋ポリスチレン粒子、架橋スチレンアクリル共重合粒子、メラミン-ホルムアルデヒド粒子、シリコーン樹脂粒子、シリカ・アクリル複合粒子、ナイロン粒子、ベンゾグアナミン-ホルムアルデヒド粒子、ベンゾグアナミン・メラミン・ホルムアルデヒド粒子、フッ素樹脂粒子、エポキシ樹脂粒子、ポリフェニレンスルフィド樹脂粒子、ポリエーテルスルホン樹脂粒子、ポリアクリロニトリル粒子、ポリウレタン粒子等が挙げられる。
無機光拡散剤としては、炭酸カルシウム(CaCO3)、酸化チタン(TiO2)、硫酸バリウム(BaSO4)、水酸化アルミニウム(Al(OH)3)、シリカ(SiO2)、タルク等が挙げられるが、得られる硬化膜の光拡散性をより高めるという観点から、酸化チタン(TiO2)や凝集シリカ粒子が好ましく、非凝集性の酸化チタン(TiO2)がより好ましい。
これらの光拡散剤は、適宜な表面修飾剤により表面処理したものを用いてもよい。
[1H-NMR]
装置:Bruker NMR System AVANCE III HD 500(500MHz)
測定溶媒:DMSO-d6
基準物質:テトラメチルシラン(TMS)(δ0.0ppm)
[GPC]
装置:東ソー(株)製 HLC-8200 GPC
カラム:東ソーTSKgel α-3000 +東ソーTSKgel α-4000
カラム温度:40℃
溶媒:ジメチルホルムアミド(DMF)
検出器:UV(271nm)
検量線:標準ポリスチレン
[エリプソメーター]
装置:ジェー・エー・ウーラム・ジャパン製 多入射角分光エリプソメーターVASE
[濁度計]
装置:日本電色工業株式会社製 HAZE METER NDH 5000
[分光測色計]
装置:コニカミノルタ製 CM-3700A
[露光]
装置:アイグラフィックス(株)製UV照射装置
化合物P-2のGPCによるポリスチレン換算で測定される重量平均分子量Mwは5,280、多分散度Mw/Mnは2.7であった。
以下の製造例1~4で実施した物性測定の方法および測定装置を以下に示す。
(1)水分量:カールフィッシャー滴定法にて求めた。
(2)一次粒子径:分散液を銅メッシュ上で乾燥させ、透過型電子顕微鏡にて観察し、100個の粒子径を測定し、その平均値を一次粒子径として求めた。
(3)比重:浮き秤法にて求めた(20℃)。
(4)粘度:オストワルド粘度計にて求めた(20℃)。
(5)動的光散乱法による粒子径:Malvern製、Zetasizer Nanoで測定して求めた。
(6)固形分濃度:500℃で焼成した際の残存固形物より求めた。
(7)有機シラン化合物の結合量:変性金属酸化物コロイド粒子に結合した有機シラン化合物の量は、元素分析により求めた。
装置:PerkinElmer製、SeriesII CHNS/O Analyzer 2400
1リットルの容器に純水126.2gを入れ、メタスズ酸17.8g(SnO2換算で15g含有、昭和化工(株)製)、チタンテトライソプロポキシド284g(TiO2換算で80g含有、日本曹達(株)製A-1)、シュウ酸二水和物98(シュウ酸換算で70g含有、宇部興産(株)製)、35質量%水酸化テトラエチルアンモニウム水溶液438g(セイケムジャパン製)を攪拌下で添加した。得られた混合溶液は、シュウ酸/チタン原子のモル比0.78、水酸化テトラエチルアンモニウム/チタン原子のモル比1.04であった。該混合溶液950gを、80℃で2時間保持し、さらに580Torrまで減圧して2時間保持し、チタン混合溶液を調製した。調製後のチタン混合溶液のpHは4.7、電導度は27.2mS/cm、金属酸化物濃度10.0質量%であった。3リットルのガラスライニングされたオートクレーブ容器に上記チタン混合溶液950g、純水950gを投入し、140℃で5時間水熱処理を行った。室温に冷却後、取り出された水熱処理後の溶液は淡い乳白色の酸化チタン含有コロイド粒子の水分散液であった。得られた分散液は、pH3.9、電導度19.7mS/cm、TiO2濃度4.2質量%、水酸化テトラエチルアンモニウム濃度8.0質量%、シュウ酸濃度3.7質量%、動的光散乱法粒子径16nm、透過型電子顕微鏡観察では、一次粒子径5~15nmの楕円粒子が観察された。得られた分散液を110℃で乾燥させた粉末のX線回折分析を行い、ルチル型結晶であることが確認された。得られた酸化チタン含有コロイド粒子を核粒子(A)とした。次いで、オキシ塩化ジルコニウム(ZrO2として21.19質量%含有、第一稀元素化学工業(株)製)70.8gを純水429.2gで希釈してオキシ塩化ジルコニウム水溶液500g(ZrO2として3.0質量%含有、)を別途調製し、これに核粒子(A)の分散液(水分散ゾル)1,000gを攪拌下で添加した。次いで、95℃に加熱して加水分解を行って、表面に酸化ジルコニウムの薄膜層が形成された酸化チタン含有核粒子(A1)(以下、第1金属酸化物粒子(A1))の水分散ゾルが得られた。得られた水分散ゾルは、pH1.2、全金属酸化物濃度20質量%であり、透過型電子顕微鏡観察では、一次粒子径4~8nmのコロイド粒子が観察された。
JIS3号珪酸ナトリウム(SiO2として29.8質量%含有、富士化学(株)製)77.2gを純水1,282gに溶解し、次いで、スズ酸ナトリウムNaSnO3・H2O(SnO2として55.1質量%含有、昭和化工(株)製)20.9gを溶解した。得られた水溶液を水素型陽イオン交換樹脂(アンバーライト(登録商標)IR-120B)を充填したカラムに通すことにより、酸性の二酸化珪素-酸化第二スズ複合コロイド粒子(B1)の水分散ゾル(pH2.4、SnO2として0.44質量%、SiO2として0.87質量%を含有、SiO2/SnO2質量比2.0)2,634gを得た。次いで、得られた水分散ゾルにジイソプロピルアミンを6.9g添加した。得られたゾルは、アルカリ性の二酸化珪素-酸化第二スズ複合コロイド粒子(B1)(以下、第2金属酸化物粒子(B1))の水分散ゾルであり、pH8.0であった。該水分散ゾルでは、透過型電子顕微鏡により5nm以下の一次粒子径のコロイド粒子が観察された。
製造例1で得られた第1金属酸化物粒子(A1)の水分散ゾル1,455gを製造例2で調製した第2金属酸化物粒子(B1)の水分散ゾル2,634gに撹拌下で添加した。次いで、アニオン交換樹脂(アンバーライト(登録商標)IRA-410、オルガノ(株)製)500ミリリットルを詰めたカラムに通液した。次いで、通液後の水分散ゾルを95℃で3時間加熱した後、水素型陽イオン交換樹脂(アンバーライト(登録商標)IR-120B)を充填したカラムに通液し、トリ-n-ペンチルアミンで安定化させ、限外ろ過膜法で濃縮し、第1金属酸化物粒子(A1)と第2金属酸化物粒子(B1)との間に酸化ジルコニウムからなる中間薄膜層が形成されている二酸化珪素-酸化第二スズ複合酸化物被覆酸化チタン含有コロイド粒子(C1)(以下、第3金属酸化物粒子(C1))の水分散ゾルを得た。得られた水分散ゾルの全金属酸化物濃度は20質量%であり、このゾルの透過型電子顕微鏡観察による一次粒子径は4~10nmであった。次いで、得られた水分散ゾルの分散媒をロータリーエバポレーターを用いてメタノールに置換して、第3金属酸化物粒子(C1)のメタノール分散ゾルを得た。このメタノール分散ゾルは、全金属酸化物濃度30質量%、粘度1.5mPa・s、動的光散乱法による粒子径18nm、水分1.0質量%であった。
製造例3で得られた第3金属酸化物粒子(C1)のメタノール分散ゾル533gにポリエーテル変性シラン(信越化学工業(株)製、商品名:X-12-641)を8.0g添加し、70℃で還流加熱を5時間行った。次いで、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名:KBM-503)を6.4g添加し、70℃で還流加熱を5時間行ない、ポリエーテル変性シランの加水分解物および3-メタクリロキシプロピルトリメトキシシランの加水分解物が表面に結合した表面修飾コロイド粒子(D1)(以下、表面修飾金属酸化物粒子(D1))のメタノール分散液を得た。次いで、エバポレータを用いて80Torrでプロピレングリコールモノメチルエーテルを添加しながらメタノールを留去することによりメタノールをプロピレングリコールモノメチルエーテルに置換して、表面修飾金属酸化物粒子(D1)のプロピレングリコールモノメチルエーテル分散液を530g得た。得られた分散液は、比重1.209、粘度3.6mPa・s、全金属酸化物濃度30.0質量%、透過型電子顕微鏡観察による一次粒子径は5~10nm、動的光散乱法粒子径は11nmであった。得られた表面修飾金属酸化物粒子(D1)において、第3金属酸化物粒子(C1)の表面に結合したポリエーテル変性シランの加水分解物は、第3金属酸化物粒子(C1)の全金属酸化物に対して4.0質量%であり、第3金属酸化物粒子(C1)の表面に結合した3-メタクリロキシプロピルトリメトキシシランの加水分解物は、第3金属酸化物粒子変性コロイド粒子(C1)の全金属酸化物に対し、2.5質量%であった。
[参考例1-1]
合成例1-1で得られた化合物P-2(1.0g)を、PGME(9.0g)に溶解して、10質量%均一透明なワニスを調製した(以下、P-2溶液という)。
得られたP-2溶液を、50mm×50mm×0.7mmの無アルカリガラス基板上にスピンコーターを用いて500nm狙いでスピンコートし、100℃のホットプレートで1分間仮焼成した後、250℃で5分間本焼成して硬化膜(以下、P-2膜という)を得た。
[実施例1-1]
合成例1-1で調製した化合物P-2のPGME溶液(5.697g)に、無機微粒子として30質量%PGME溶液のD1(10.254g)、架橋剤としてトリメチロールプロパントリアクリレート(A-TMPT、1100mPa・s、新中村化学工業(株)社製)1.538g、AT-20E(新中村化学工業(株)社製)1.538g、光重合開始剤として2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン(Omnirad907、IGM Resins B.V.社製)0.137g、界面活性剤として10質量%PGME溶液のメガファックR-40(DIC(株)製)0.017g、並びにPGME0.819gを加えて目視で溶解したことを確認し、固形分40質量%のワニスを調製した(以下、SP-2溶液という)。
このSP-2溶液を50mm×50mm×0.7mmの無アルカリガラス基板上に、スピンコーターにて200rpmで5秒間、1,000rpmで30秒間スピンコートし、ホットプレートを用いて100℃で1分間仮乾燥後、UV照射装置にて365nmの波長の光にて、300mJ/cm2の露光量を照射して硬化膜(以下、SP-2膜という)を得た。
無機微粒子として30質量%PGME溶液のD1(10.254g)、架橋剤としてトリメチロールプロパントリアクリレート(A-TMPT、1100mPa・s、新中村化学工業(株)社製)1.538g、AT-20E(新中村化学工業(株)社製)1.538g、光重合開始剤として2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン(Omnirad907、IGM Resins B.V.社製)0.137g、界面活性剤として10質量%PGME溶液のメガファックR-40(DIC(株)製)0.017g、並びにPGME0.819gを加えて目視で溶解したことを確認し、固形分40質量%のワニスを調製した(以下、S-2溶液という)。
このS-2溶液を用いて、実施例1-1と同様の手順で硬化膜(以下、S-2膜という)を得た。
Claims (16)
- 前記式(1)中のQが、式(2)~(13)及び式(102)~(115)で示される群から選ばれる少なくとも1種を表す、請求項1に記載の膜形成用組成物。
R93およびR94は、水素原子または炭素数1~10のアルキル基を表し、
W1およびW2は、互いに独立して、単結合、CR95R96(R95およびR96は、互いに独立して、水素原子、炭素数1~10のアルキル基(ただし、これらは一緒になって環を形成していてもよい。)、または炭素数1~10のハロゲン化アルキル基を表す。)、C=O、O、S、SO、SO2、またはNR97(R97は、水素原子、炭素数1~10のアルキル基またはフェニル基を表す。)を表し、
X1およびX2は、互いに独立して、単結合、炭素数1~10のアルキレン基、または式(14)
Y1およびY2は、互いに独立して、単結合または炭素数1~10のアルキレン基を表す。)で示される基を表す。
*は結合手を表す。〕
- 前記式(2)~(13)における前記R1~R92およびR98~R101が、水素原子である請求項2に記載の膜形成用組成物。
- 前記架橋剤が、多官能(メタ)アクリル化合物である請求項1に記載の膜形成用組成物。
- 前記親水性基が、ポリエーテル基である請求項1に記載の膜形成用組成物。
- 前記架橋性基が、ラジカル重合性基である請求項1に記載の膜形成用組成物。
- 前記無機微粒子が、金属酸化物、金属硫黄物または金属窒化物を含む請求項1に記載の膜形成用組成物。
- 前記トリアジン環末端の少なくとも一部が、フッ素原子含有基を有するアミノ基で封止されている、請求項1に記載の膜形成用組成物。
- 前記R102が、炭素数1~10のパーフルオロアルキル基である請求項9に記載の膜形成用組成物。
- 前記有機溶媒が、グリコールエステル系溶媒、ケトン系溶媒、およびエステル系溶媒から選ばれる少なくとも1種を含む請求項1に記載の膜形成用組成物。
- 請求項1~13のいずれかに記載の膜形成用組成物から得られる薄膜。
- 基材と、前記基材上に形成された請求項14に記載の薄膜とを備える電子デバイス。
- 基材と、前記基材上に形成された請求項14に記載の薄膜とを備える光学部材。
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