WO2017170385A1 - 被膜形成用組成物及びその製造方法 - Google Patents
被膜形成用組成物及びその製造方法 Download PDFInfo
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- WO2017170385A1 WO2017170385A1 PCT/JP2017/012367 JP2017012367W WO2017170385A1 WO 2017170385 A1 WO2017170385 A1 WO 2017170385A1 JP 2017012367 W JP2017012367 W JP 2017012367W WO 2017170385 A1 WO2017170385 A1 WO 2017170385A1
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- metal oxide
- coating
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- KRIUTXYABPSKPN-UHFFFAOYSA-N trimethoxy-[3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]propyl]silane Chemical compound COCCOCCOCCOCCC[Si](OC)(OC)OC KRIUTXYABPSKPN-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G23/00—Compounds of titanium
- C01G23/04—Oxides; Hydroxides
- C01G23/047—Titanium dioxide
- C01G23/053—Producing by wet processes, e.g. hydrolysing titanium salts
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G19/00—Compounds of tin
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/02—Ingredients treated with inorganic substances
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
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- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/0081—Composite particulate pigments or fillers, i.e. containing at least two solid phases, except those consisting of coated particles of one compound
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3653—Treatment with inorganic compounds
- C09C1/3661—Coating
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/006—Combinations of treatments provided for in groups C09C3/04 - C09C3/12
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/02—Polysilicates
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- C09D185/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/66—Additives characterised by particle size
- C09D7/67—Particle size smaller than 100 nm
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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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
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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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/14625—Optical elements or arrangements associated with the device
- H01L27/14627—Microlenses
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- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
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- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
- C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases
- C01P2004/84—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases one phase coated with the other
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- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
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- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
- C01P2006/82—Compositional purity water content
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
Definitions
- the present invention relates to a film forming composition and a method for producing the same, and more specifically, a film forming cloth comprising inorganic fine particles to which a hydrolyzable condensate of hydrolyzable silane and an amphiphilic organosilicon compound are bonded. It is related with a composition and its manufacturing method.
- This method is a method of achieving a high refractive index by mixing a polymer and inorganic fine particles.
- a mixing method a method of mixing a polymer solution and a dispersion of inorganic fine particles is generally used.
- the polymer plays a role as a binder that stabilizes the dispersion of the inorganic fine particles without breaking.
- a hydrolyzable silane hydrolysis condensate or polyimide can be used as the binder polymer.
- a technique has been reported in which a refractive index is increased by using a hybrid material obtained by mixing a hydrolysis condensate of alkoxysilane and an inorganic oxide dispersion material in which zirconia or titania is dispersed (see Patent Document 1).
- a technique for increasing the refractive index using a hybrid material in which polyimide and titania, zinc sulfide, or the like are dispersed has been reported (see Patent Document 2).
- these hybrid materials have been devised to increase the refractive index, they are compositions in a high refractive index region with a refractive index exceeding 1.7 and can be produced with a film thickness exceeding 1 ⁇ m.
- the present situation is that no study has been made on the storage stability of the coating composition.
- Specific properties required include heat resistance, transparency, high refractive index, thick film, crack resistance, storage stability of the coating composition, and the like.
- the method of realizing the increase in the film thickness by increasing the solid content concentration of the coating composition is to increase the viscosity of the coating composition by increasing the solid content concentration, and the film made from the coating composition having a high viscosity is thick. It is caused by becoming.
- This approach applies to organic polymers such as acrylic polymers.
- a coating composition containing polysiloxane and inorganic fine particles is difficult to increase in thickness because the viscosity of the composition is hardly increased even when the solid content concentration is increased, that is, a film is formed with a low viscosity.
- the content of inorganic fine particles in the coating composition increases as described above in order to improve the refractive index, and the viscosity of the coating composition increases. It becomes difficult. This is because the inorganic fine particles selected for the coating composition in the field exist in a highly dispersed state in the coating composition, and the inorganic fine particles with high dispersibility have a characteristic that it is difficult to increase the viscosity. by.
- the thickening of the composition containing the hydrolyzable condensate of hydrolyzable silane and the inorganic fine particles may be possible by increasing the viscosity of the coating composition by increasing the dispersed particle size of the inorganic fine particles. .
- an object of the present invention is to provide a film-forming composition that can be thickened and has excellent storage stability of the coating composition, and a method for producing the same.
- composition containing a hydrolyzable condensate of hydrolyzable silane and inorganic fine particles subjected to a special dispersion treatment is suitable as a film-forming composition for producing an electronic device.
- the present invention has been completed.
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 2 is an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms
- a is 0 to 3
- a film-forming composition comprising inorganic fine
- R 2 in the formula (1) is a methyl group, an ethyl group, a phenyl group, a biphenyl group, or a phenanthryl group, and a is 1, the film forming composition according to 1, 3. 3.
- the organosilicon compound having amphiphilic properties bonded to the surface of the modified metal oxide colloidal particle (B3) as the component (B) is 3 to 3 to the total metal oxide of the modified metal oxide colloidal particle (B3).
- the group (B) component metal oxide colloidal particles (B1) are composed of Ti, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi, and Ce.
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 2 is an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms
- a is 0 to 3
- Metal oxide colloidal particles (B1) having a primary particle size of 2 to 60 nm as a core, and the surface of 1 to 4 nm
- the coating (B2) comprising metal oxide colloidal particles having a primary particle size of Having at least one poly (oxyalkylene) group selected from an ethylene group, a polyoxypropylene group or a polyoxybutylene group, and being selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group as a hydrophobic group
- R 2 in the formula (1) is a methyl group, an ethyl group, a phenyl group, a biphenyl group or a phenanthryl group, and a is 1,
- the process for producing a film-forming composition according to any one of 7 to 9, comprising a step of heating at 23 ° C. to 150 ° C. after the step of mixing the component (A) and the component (B). Method, 11.
- An electronic device comprising a substrate and the coating according to 11 formed on the substrate, 13.
- An optical member comprising a base material and the coating film according to 11 formed on the base material,
- component (A) the following formula (1)
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 2 is an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms
- a is 0 to 3
- Metal oxide colloidal particles (B1) having a primary particle size of 2 to 60 nm as a core, and the surface of 1 to 4 nm
- the coating (B2) comprising metal oxide colloidal particles having a primary particle size of Having at least one poly (oxyalkylene) group selected from an ethylene group, a polyoxypropylene group or a polyoxybutylene group, and being selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group as a hydrophobic group
- a poly (oxyalkylene) group selected from an ethylene group, a polyoxypropylene group or a polyoxybutylene group, and being selected from
- inorganic fine particles having a high refractive index (component (component (A)) subjected to a special dispersion treatment rather than a hydrolysis condensate of hydrolyzable silane having a low refractive index (component (A))
- component (A) component (component (A))
- the film-forming composition having an increased content of B) By using the film-forming composition having an increased content of B)), the viscosity of the composition increases and a thick film can be formed.
- the resulting film-forming composition has good storage stability, and the resulting film exhibits a high refractive index and high transparency.
- the composition containing the component (A) and the component (B) has high heat resistance and transparency, and can be made thick while exhibiting a high refractive index. It is possible to provide a film-forming composition capable of forming a certain film and having excellent storage stability.
- the lower limit is preferably 1.70 or more, more preferably 1.75 or more, and still more preferably 1 .80 or more.
- the upper limit is not particularly limited, but is 2.00 or less, or 1.95 or less.
- 1.70 or more is called a high refractive index at a wavelength of 550 nm.
- the film forming composition of the present invention can increase the viscosity as compared with a conventional composition containing a hydrolyzable condensate of hydrolyzable silane and inorganic fine particles, and therefore can be made thicker.
- a thick film can be obtained without applying twice by spin coating or using a complicated spin recipe, and the process margin is wide.
- the film forming composition of the present invention retains the high dispersibility of the inorganic fine particles, so that the storage stability of the film forming composition is good, and a sudden viscosity increase or gelation occurs during storage. Does not occur, the product life is long, and as a result, the cost can be reduced.
- the film forming composition of the present invention can control the film thickness, refractive index, and transmittance by changing the type of hydrolyzable condensate of hydrolyzable silane or changing the amount of addition.
- the film produced using the film-forming composition of the present invention having the above-mentioned characteristics is a liquid crystal display, an organic electroluminescence (OLED) display, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, It can use suitably as a member at the time of producing electronic devices, such as a dye-sensitized solar cell and an organic thin-film transistor (TFT). Moreover, it can utilize suitably as a member for lenses by which high refractive index is calculated
- a buried film and a planarizing film on a photodiode, a planarizing film before and after a color filter, a microlens, a planarizing film and a conformal film on a microlens, which are members of a solid-state imaging device that requires a high refractive index. can be suitably used.
- hydrolyzable condensate of the hydrolyzable silane of the component (A) contained in the film forming composition of the present invention is the following formula (1)
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 2 is an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms
- a is 0 to 3 (It is an integer.)
- the silanol groups undergo dehydration condensation to form polysiloxane.
- examples of the alkyl group represented by R 1 include alkyl groups having 1 to 6 carbon atoms, and those having a linear, branched, or cyclic alkyl moiety such as a methyl group, an ethyl group, and the like.
- N-propyl group isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group N-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n- Butyl group, 1,2-dimethyl-n-butyl group, 1,3-dimethyl-n-butyl group, 2,2-dimethyl-n-butyl group, 2,3-dimethyl-n-butyl group
- the alkyl group having 1 to 18 carbon atoms of R 2 has a linear, branched or cyclic alkyl moiety, and is a methyl group, an ethyl group, an n-propyl group, an isopropyl group.
- n-butyl group isobutyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, -Methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2- Dimethyl-n-butyl group, 1,3-dimethyl-n-butyl Group, 2,2-dimethyl-n-butyl group, 2,3-dimethyl-n-butyl group, 3,3-dimethyl-methyl-
- examples of the aryl group having 6 to 18 carbon atoms of R 2 include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, and a cyclohexyl group.
- hydrolyzable silane represented by the formula (1) examples include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane, methyltrimethoxysilane.
- Nontryltrimethoxysilane, biphenyltrimethoxysilane, dimethoxydimethylsilane and the like are exemplified, but not limited thereto.
- hydrolyzable condensate of the hydrolyzable silane (A) component other hydrolyzable silanes having a halogen atom as a hydrolyzing group, such as tetrachlorosilane, together with the hydrolyzable silane represented by the formula (1) A compound may be used.
- R 2 a is an integer of 0 to 3, namely, hydrolysis condensate of the hydrolyzable silane represented by the formula (1) are tetrafunctional, trifunctional or bifunctional poly Indicates siloxane.
- the weight average molecular weight of the hydrolysis condensate of at least one hydrolyzable silane represented by the formula (1) is, for example, 1,000 to 100,000. These molecular weights are average molecular weights obtained in terms of standard polystyrene by gel permeation chromatography (hereinafter abbreviated as GPC) analysis.
- GPC gel permeation chromatography
- Examples of the catalyst for hydrolysis when synthesizing the hydrolysis condensate include organic acids, inorganic acids, organic bases, and inorganic bases.
- organic acids include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, gallic acid Acid, butyric acid, meritic acid, arachidonic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linolenic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzenesulfonic acid, monochloro Examples include acetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid, phthalic acid, fuma
- Examples of inorganic acids include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
- Examples of the organic base include pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicyclooctane, diazabicyclononane. And diazabicycloundecene, tetramethylammonium hydroxide, 1,8-diazabicyclo [5,4,0] -7-undecene, and the like.
- Examples of the inorganic base include ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide and the like. Of these catalysts, organic acids and inorganic acids are preferable, and one or more catalysts may be used simultaneously.
- Hydrolysis of an alkoxy group bonded to a silicon atom of a hydrolyzable silane involves 0.1 to 100 mol, or 0.1 to 10 mol, per mol of these hydrolyzable groups. Or 1 to 5 mol, or 2 to 3.5 mol of water. Further, 0.0001 to 10 mol, preferably 0.001 to 2 mol of hydrolysis catalyst can be used per mol of hydrolyzing group.
- the reaction temperature when hydrolyzing and condensing the hydrolyzable silane is usually 23 ° C. (room temperature) or higher and the reflux temperature at normal pressure of the organic solvent used for the hydrolysis.
- Hydrolysis of the hydrolyzable silane may be performed completely, that is, all hydrolyzable groups may be changed to silanol groups, or partially hydrolyzed, that is, unreacted hydrolyzable groups may be left. Further, an uncondensed hydrolyzate may remain after the hydrolysis and condensation reaction.
- the method of heating the mixture of a hydrolysable silane compound, an organic solvent, water, and the catalyst for hydrolysis is mentioned.
- oxalic acid hydrolysis catalyst
- alcohol organic solvent
- the amount of oxalic acid is generally 0.2 to 2 mol with respect to 1 mol of all hydrolyzable groups (alkoxy group and the like) of the hydrolyzable silane compound.
- Heating in this method can be performed at a liquid temperature of 50 to 180 ° C., and preferably, for example, under reflux in a sealed container for 10 minutes to 12 hours so that the liquid does not evaporate or volatilize.
- the hydrolyzable silane hydrolyzed condensate may be produced by adding an organic solvent, water and a catalyst for hydrolysis to the hydrolyzable silane compound and reacting them. The order may be such that the hydrolyzable silane compound is added to the mixture of the catalyst for decomposition and reacted.
- the reaction temperature for synthesizing the hydrolyzable silane hydrolysis condensate may be 0 to 50 ° C. for the purpose of stably synthesizing a uniform polymer, and the reaction time is 24 to 2000 hours. be able to.
- the aforementioned catalyst for hydrolysis can be selected for the purpose of controlling the amount of silanol groups in the hydrolysis condensate of the resulting hydrolyzable silane.
- silanol groups Generally, when an acid is selected, many silanol groups remain and a base is selected. Then, the silanol group decreases.
- the amount of the silanol group is large, there is an effect of increasing the viscosity of the film forming composition, and it may be appropriately selected in a region where the storage stability of the film forming composition can be maintained.
- organic solvent used for hydrolysis examples include toluene, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, t-butanol, diacetone alcohol acetone, methyl ethyl ketone, methyl isobutyl ketone, Cyclohexanone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether, ⁇ -butyrolactone, n-propyl acetate, ethyl lactate N-methyl-2-pyrrolidone and the like.
- organic solvent an alcohol is generally generated by a hydrolysis reaction. Therefore, it is preferable to use an alcohol or an organic solvent having good compatibility with the alcohol.
- organic solvents include methanol, ethanol, n-propanol, isopropanol, n-butanol, methyl ethyl ketone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol.
- Preferable examples include monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether, n-propyl acetate, ethyl lactate and cyclohexanone.
- the hydrolysis condensate (polysiloxane) of the component (A) is obtained by hydrolyzing a hydrolyzable silane in an organic solvent and subjecting the hydrolyzate to a condensation reaction. It is obtained in the form of a polysiloxane varnish dissolved in a solvent.
- the obtained polysiloxane varnish may be solvent-substituted.
- a solvent during synthesis when ethanol is selected as an organic solvent during hydrolysis and condensation reactions (hereinafter referred to as a solvent during synthesis), after a polysiloxane is obtained in ethanol, a substitution solvent is added, and an evaporator or the like is used.
- azeotropically distilling off ethanol the solvent can be replaced with a replacement solvent.
- the boiling point is preferably lower than that of the substitution solvent.
- the synthesis solvent includes methanol, ethanol, isopropanol, and the like
- the substitution solvent includes propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, and the like.
- the obtained polysiloxane varnish can be made to have a solid concentration of 100% by distilling off the organic solvent if the storage stability is not bad.
- the organic solvent used for diluting the polysiloxane varnish may be the same as or different from the organic solvent used for the hydrolysis reaction of the hydrolyzable silane.
- the solvent for dilution is not particularly limited, and one or two or more kinds can be arbitrarily selected and used.
- organic solvents for dilution include toluene, p-xylene, o-xylene, 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 methyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, propylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, dipropylene glycol Nomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, triethylene glycol dimethyl ether, diethylene glycol dimethyl
- the inorganic fine particles of component (B) contained in the film-forming composition of the present invention are metal oxide colloidal particles (B1) having a primary particle diameter of 2 to 60 nm as a nucleus, and the surface is primary to 1 to 4 nm.
- a polyoxyethylene group is used as a hydrophilic group.
- One or more poly (oxyalkylene) groups selected from a polyoxypropylene group or a polyoxybutylene group, and one kind selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group as a hydrophobic group Inorganic fine particles to which an amphiphilic organosilicon compound having the above group is bonded.
- the primary particle diameter of colloidal particles can be measured by observation with a transmission electron microscope.
- the metal oxide colloidal particles (B1) can be produced by a known method such as an ion exchange method, a peptization method, a hydrolysis method, or a reaction method.
- the ion exchange method include a method of treating a metal acid salt with a hydrogen ion exchange resin, or a method of treating a metal basic salt with a hydroxyl group anion exchange resin.
- the peptization method a method of neutralizing a metal acid salt with a base or washing a gel obtained by neutralizing a metal basic salt with an acid and then peptizing with an acid or a base Is mentioned.
- Examples of the hydrolysis method include a method of hydrolyzing a metal alkoxide, or a method of removing an unnecessary acid after hydrolyzing a metal basic salt under heating.
- Examples of the reaction method include a method of reacting a metal powder with an acid.
- the metal oxide colloidal particles (B1) are at least one selected from the group consisting of Ti, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi, and Ce. It is an oxide of a seed metal.
- the colloidal particles of the metal oxide are oxides of metals having a valence of 2 to 6. Examples of the metal oxides include TiO 2 , Fe 2 O 3 , CuO, ZnO, Y 2 O 3 , ZrO 2. , can be exemplified Nb 2 O 5, MoO 3, In 2 O 3, SnO 2, Sb 2 O 5, Ta 2 O 5, WO 3, PbO, Bi 2 O 3 and the like. These metal oxides can be used alone or in combination. Examples of the combination include a method of mixing several kinds of the metal oxides, a method of compounding the metal oxides, and a method of solidifying the metal oxides at an atomic level.
- SnO 2 -WO 3 composite colloidal particles and SnO 2 particles and WO 3 particles are complexed occurs a chemical bond at the interface, and the SnO 2 particles and ZrO 2 particles at the interface
- SnO 2 —ZrO 2 composite colloidal particles composited by forming TiO 2 —ZrO 2 —SnO 2 composite colloidal particles obtained by forming a solid solution of TiO 2 , ZrO 2 and SnO 2 at the atomic level It is done.
- the metal oxide colloid particles (B1) may also be used as a compound with a combination of metal components, include, for example, ZnSb 2 O 6, InSbO 4, ZnSnO 3.
- the metal oxide colloidal particles (B1) are used as nuclei, and the surface thereof is coated with a coating (B2) made of metal oxide colloidal particles having a primary particle diameter of 1 to 4 nm.
- (B3) is obtained, and has at least one poly (oxyalkylene) group selected from a polyoxyethylene group, a polyoxypropylene group or a polyoxybutylene group as a hydrophilic group on its surface,
- Inorganic fine particles of the component (B) can be obtained by bonding an organosilicon compound having one or more groups selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group.
- the metal oxide used for the coating (B2) is colloidal particles of at least one metal oxide selected from the group consisting of Si, Al, Sn, Zr, Mo, Sb and W.
- Said coating (B2) is in the form of metal oxides, for example can be mentioned SiO 2, Al 2 O 3, SnO 2, ZrO 2, MoO 3, Sb 2 O 5, WO 3 and the like. These metal oxides can be used alone or in combination. Examples of the combination include a method of mixing several kinds of the metal oxides, a method of combining the metal oxides, and a method of solidifying the metal oxides at an atomic level.
- SnO 2 -WO 3 composite colloidal particles and SnO 2 particles and WO 3 particles are complexed occurs a chemical bond at the interface
- the coating (B2) can be produced by a known method such as an ion exchange method or an oxidation method.
- a method of treating the acid salt of the metal with a hydrogen ion exchange resin can be mentioned.
- a method of reacting the metal or metal oxide powder with hydrogen peroxide can be given.
- Examples of the method for producing the modified metal oxide colloidal particles (B3) include the following first method and second method.
- an aqueous sol containing metal oxide colloidal particles (B1) as nuclei and an aqueous sol containing a coating (B2) are converted into respective metal oxides (B2) / (
- the mixed sol is heated after mixing so that the mass ratio of B1) is 0.05 to 0.5.
- the aqueous sol containing particles is mixed so that the mass ratio of (B2) / (B1) converted to each metal oxide is 0.05 to 0.5, and the mixed sol is 70 to 350 ° C.
- a modified metal oxide sol comprising particles (B3) having the metal oxide colloidal particles (B1) as nuclei and the surfaces coated with Sb 2 O 5 —SiO 2 composite colloidal particles (B2). It is done.
- an aqueous sol containing metal oxide colloidal particles (B1) as nuclei, and a water-soluble tin oxide alkali salt and a water-soluble silicon oxide alkali salt as a coating (B2) After mixing so that the mass ratio of SnO 2 / SiO 2 converted to each metal oxide is 0.1 to 5, cation exchange is performed to remove alkali metal ions, and the resulting composite colloidal particles
- the aqueous sol is mixed and heated.
- an aqueous solution of the water-soluble alkali salt used in the second method an aqueous solution of a sodium salt can be preferably used.
- an SnO 2 —SiO 2 composite obtained by cation exchange after mixing an aqueous sol containing metal oxide colloidal particles (B1) and an aqueous solution of sodium stannate and sodium silicate as a coating (B2)
- the aqueous sol of colloidal particles is mixed so that the mass ratio of (SnO 2 —SiO 2 ) / (B2) converted to each metal oxide is 0.05 to 0.5.
- the metal oxide colloidal particles (B1) are used as nuclei, and the surfaces thereof are modified metal oxide colloidal particles (B2) coated with a coating (B2) made of SnO 2 —SiO 2 composite colloidal particles ( An aqueous sol of B3) is obtained.
- the mixing of the metal oxide colloidal particles (B1) and the coating (B2) can be performed at a temperature of 1 to 100 ° C., preferably from room temperature to 60 ° C.
- the heating after mixing is preferably performed at 70 to 350 ° C.
- the sol of the modified metal oxide colloidal particles (B3) can contain other optional components as long as the object of the present invention is achieved.
- oxycarboxylic acids when oxycarboxylic acids are contained in a proportion of about 30% by mass or less with respect to the total amount of all metal oxides, a colloid with further improved performance such as dispersibility can be obtained.
- the oxycarboxylic acid used include lactic acid, tartaric acid, citric acid, gluconic acid, malic acid, glycol and the like.
- the sol of the modified metal oxide colloidal particles (B3) can contain an alkali component, for example, alkali metal hydroxides such as Li, Na, K, Rb, and Cs, ammonia, ethylamine, and isopropylamine.
- alkali metal hydroxides such as Li, Na, K, Rb, and Cs
- ammonia ethylamine
- isopropylamine ethylamine
- alkali components can be contained singly or in combination of two or more.
- the alkali component can be contained in a proportion of about 30% by mass or less based on the total metal oxide of the modified metal oxide colloidal particles (B3). Moreover, it can use together with the said oxycarboxylic acid.
- an organic solvent sol can be obtained by replacing the aqueous medium of the aqueous sol with a hydrophilic organic solvent.
- This substitution can be performed by a usual method such as a distillation method or an ultrafiltration method.
- the hydrophilic organic solvent include lower alcohols such as methyl alcohol, ethyl alcohol and isopropyl alcohol, ethers such as propylene glycol monomethyl ether, linear amides such as dimethylformamide and N, N′-dimethylacetamide, N -Cyclic amides such as methyl-2-pyrrolidone, and glycols such as ethyl cellosolve and ethylene glycol.
- the inorganic fine particles which are the component (B) of the present invention are selected from polyoxyethylene group, polyoxypropylene group or polyoxybutylene group as a hydrophilic group on the surface of the modified metal oxide colloidal particle (B3).
- An amphiphilic organosilicon compound having at least one poly (oxyalkylene) group and having at least one group selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group as a hydrophobic group is bonded. Is.
- the number of added moles of the polyoxyethylene group, polyoxypropylene group or polyoxybutylene group as the hydrophilic group is preferably 3 to 40.
- amphiphilic organosilicon compound used in the present invention include methoxytriethyleneoxypropyltrimethoxysilane, methoxytriethyleneoxyoctyltrimethoxysilane, methoxytriethyleneoxypropyltriethoxysilane, and methoxytriethyleneoxypropyl.
- Tripropoxysilane methoxytriethyleneoxypropyltriacetoxysilane, methoxytripropyleneoxypropyltrimethoxysilane, methoxytripropyleneoxyoctyltrimethoxysilane, methoxytripropyleneoxypropyltriethoxysilane, methoxytripropyleneoxypropyltripropoxysilane, methoxy Tripropyleneoxypropyltriacetoxysilane, methoxytributyleneoxypropyltrimeth Sisilane, methoxytributyleneoxyoctyltrimethoxysilane, methoxytributyleneoxypropyltriethoxysilane, methoxytributyleneoxypropyltripropoxysilane, methoxytributyleneoxypropyltriacetoxysilane, methoxytriethyleneoxypropyldimethoxymethylsilane, methoxytripropylene Oxydimethoxymethylsilane, methoxy
- the binding amount of the amphiphilic organosilicon compound to the surface of the modified metal oxide colloidal particles (B3) is 0.1 to 30 mass based on the total metal oxides of the modified metal oxide colloidal particles (B3). % Is preferable, and more preferably 1 to 15% by mass.
- the inorganic fine particles as the component (B) of the present invention are prepared by adding a predetermined amount of the amphiphilic organosilicon compound to the aqueous sol or hydrophilic organic solvent sol of the modified metal oxide colloidal particles (B3), and dilute hydrochloric acid or the like.
- the organosilicon compound can be hydrolyzed with a catalyst and bonded to the surface of the modified metal oxide colloidal particles (B3).
- the film-forming composition of the present invention can contain other optional components as long as the object of the present invention is achieved.
- phosphoric acid, phosphoric acid derivatives, phosphoric acid surfactants, and oxycarboxylic acids are contained in a proportion of about 30% by mass or less based on the total metal oxides of the modified metal oxide colloidal particles (B3).
- phosphoric acid derivatives used include phenylphosphonic acid and metal salts thereof.
- Examples of the phosphoric acid surfactant include Disperbyk (Bic Chemie), Phosphanol (registered trademark) (Toho Chemical Co., Ltd.), Nikkor (registered trademark) (Nikko Chemicals Co., Ltd.), and the like.
- Examples of the oxycarboxylic acid include lactic acid, tartaric acid, citric acid, gluconic acid, malic acid, glycol and the like.
- the present invention also provides the component (A): the following formula (1)
- R 1 is an alkyl group having 1 to 6 carbon atoms
- R 2 is an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms
- a is 0 to 3
- Metal oxide colloidal particles (B1) having a primary particle size of 2 to 60 nm as a core, and the surface of 1 to 4 nm
- the coating (B2) comprising metal oxide colloidal particles having a primary particle size of Having at least one poly (oxyalkylene) group selected from an ethylene group, a polyoxypropylene group or a polyoxybutylene group, and being selected from an alkylene group having 1 to 18 carbon atoms or a vinylene group as a hydrophobic group
- the present invention is directed to a method
- the mixing method of the component (A) and the component (B) is as follows: (A) a method of mixing the component (A) in a solid state with the dispersion of the component (B), (B) A method in which the component (A) is mixed with a dispersion liquid of the component (B) in a liquid state in which the component (A) is dissolved and dispersed in an organic solvent or the like (C) A method of adding and mixing the component (A) in the solid state and the step of dispersing the component (B) in a dispersion medium at the same time.
- mixing by the method (b) is preferable.
- the solvent used for the said (A) component and the solvent used for the said (B) component may be the same. However, if the solvents are different, the polarities of the two solvents are preferably close.
- solvent used in the present invention 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 mono Ethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol ethyl 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, tri
- the film forming composition of the present invention may include a heating step after the step of mixing the component (A) and the component (B).
- the heating conditions are 23 ° C or higher, preferably 50 ° C or higher, more preferably 70 ° C or higher, and 150 ° C or lower, preferably 140 ° C or lower, after mixing the component (A) and the component (B).
- the heating time is preferably 1 to 48 hours.
- the content of the component (B) in the film forming composition of the present invention may be in a range that does not impair the dispersibility of the film forming composition to be obtained. It is possible to control appropriately according to the rate and heat resistance.
- the inorganic fine particles of component (B) are in the range of 0.1 to 1,500 parts by mass.
- the amount is preferably 100 to 1,000 parts by mass, and more preferably 300 to 700 parts by mass in order to maintain the film quality and obtain a stable refractive index.
- the solid content of the hydrolyzable condensate of hydrolyzable silane is the solid content after baking at 140 ° C.
- the film-forming composition of the present invention may contain other components such as a surfactant, a crosslinking agent, a leveling agent, an anti-settling agent, an emulsifier, and the like, as long as the effects of the present invention are not impaired.
- surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol Polyoxyethylene alkyl aryl 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 polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, trade name F
- 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 3 parts by mass, and still more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the component (A).
- the crosslinking agent is not particularly limited as long as it is a compound having a substituent capable of reacting with the component (A).
- examples of such compounds include melamine compounds having a crosslinkable substituent such as methylol group and methoxymethyl group, substituted urea compounds, compounds containing a crosslinkable substituent such as epoxy group and oxetane group, and block isocyanate.
- Compounds having acid anhydrides, compounds having (meth) acrylic groups, phenoplast compounds, etc., from the viewpoint of heat resistance and storage stability, epoxy groups, blocked isocyanate groups, (meth) acrylic groups Compounds containing are preferred.
- cross-linking agents may be used alone or in combination of two or more.
- the amount of the crosslinking agent used is preferably 1 to 100 parts by mass with respect to 100 parts by mass of component (A), but considering the high refractive index, the upper limit is preferably 2 parts by mass, more preferably 5 parts by mass. Part by mass.
- the cross-linking agent and the reactive terminal silanol group of the component (A) may react to produce effects such as improvement in film density, heat resistance, and heat relaxation ability. is there.
- said other component can be added at arbitrary processes at the time of preparing the composition for film formation of this invention.
- the film-forming composition of the present invention can be applied to a substrate, and then fired as necessary to form a desired film.
- the coating is also an object of the present invention.
- the coating method of the film forming composition of the present invention is arbitrary, for example, spin coating method, dipping method, flow coating method, ink jet method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method. Methods such as transfer printing, brush coating, blade coating, and air knife coating can be employed.
- silicon glass with indium tin oxide (ITO) formed, glass with indium zinc oxide (IZO) formed, polyethylene terephthalate (PET), plastic, glass, quartz, ceramics
- ITO indium tin oxide
- IZO indium zinc oxide
- PET polyethylene terephthalate
- plastic glass, quartz, ceramics
- the film forming composition of the present invention can be filtered before use, and is not particularly limited to the effective filtration area and material of the filter medium, and may be filtered according to the target product.
- Baking can be performed for the purpose of evaporating the solvent after coating the film-forming composition on the substrate.
- the firing temperature is not particularly limited, and can be performed at 40 to 400 ° C., for example. Firing can be performed with two or more temperature changes for the purpose of developing a high uniformity with no unevenness in the distribution of film thickness, or for a reaction such as a crosslinking agent to proceed on the substrate. Good.
- the firing method is not particularly limited, and for example, the solvent may be evaporated using a hot plate or an oven in an appropriate atmosphere such as air, an inert gas such as nitrogen, or in a vacuum.
- the firing temperature and firing time may be selected under conditions suitable for the manufacturing process of the target electronic device, and the firing conditions may be selected such that the physical properties of the obtained film are suitable for the required characteristics of the electronic device.
- the film (coating film) comprising the composition of the present invention can achieve high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage. It can be suitably used as a member for producing electronic devices such as a luminescence (EL) display, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, a dye-sensitized solar cell, and an organic thin film transistor (TFT).
- a solid-state imaging device having an electronic device including a base material and a film made of the composition of the present invention formed on the base material, an optical member, and a complementary metal oxide semiconductor including the film.
- charge coupled devices, embedded materials for solid-state imaging devices, planarization materials, or microlens materials are also objects of the present invention.
- reaction solution is cooled to room temperature, 116.66 g of PGME is added to the reaction solution, and ethanol, water, and hydrochloric acid as reaction byproducts are distilled off under reduced pressure, and concentrated to a PGME solution of hydrolysis condensate (polymer).
- PGME was added and adjusted so that it might become 52 mass% in conversion of the solid residue in 140 degreeC.
- the obtained polymer is a varnish of polysiloxane (abbreviated as S1) using tetraethoxysilane as a raw material.
- the weight average molecular weight of the obtained S1 by GPC was Mw1823 in terms of polystyrene.
- Synthesis Example 2 Synthesis of polysiloxane [S2] using triethoxyphenylsilane as a raw material
- the starting material of Synthesis Example 1 was changed from tetraethoxysilane to triethoxyphenylsilane, and 3.0 equivalents of pure silane monomer was used.
- a polysiloxane (abbreviated as S2) was synthesized in the same manner except that water was used. The weight average molecular weight was Mw1251.
- Synthesis of polysiloxane [S7] using isobutyltriethoxysilane as a raw material Synthesis was performed in the same manner as in Synthesis Example 1 except that the starting material of Synthesis Example 2 was changed from triethoxyphenylsilane to isobutyltriethoxysilane. Polysiloxane (abbreviated as S7) was obtained. The weight average molecular weight was Mw 1560.
- Synthesis Example 8 Synthesis of polysiloxane [S8] using n-octyltriethoxysilane as a raw material The same as Synthesis Example 1 except that the starting material of Synthesis Example 2 was changed from triethoxyphenylsilane to n-octyltriethoxysilane. To obtain polysiloxane (abbreviated as S8). The weight average molecular weight was Mw 1371.
- Synthesis Example 10 Synthesis of polysiloxane [S10] using dimethoxydimethylsilane as a raw material
- the starting material of Synthesis Example 1 was changed from tetraethoxysilane to dimethoxydimethylsilane, and 2.0 equivalents of pure water was added to the silane monomer.
- a polysiloxane (abbreviated as S10) was obtained in the same manner as in Synthesis Example 1 except that it was used.
- the weight average molecular weight was Mw2516.
- T1 titanium oxide-containing core particle (abbreviated as T1) dispersion sol of component (B) was prepared as follows. ⁇ Preparation of core particle (B1)> Put 126.2 g of pure water in a 1 liter container, 17.8 g of metastannic acid (containing 15 g in terms of SnO 2 ), 284 g of titanium tetraisopropoxide (containing 80 g in terms of TiO 2 ), 84 g of oxalic acid dihydrate ( 70 g in terms of oxalic acid) and 438 g of a 35 mass% tetraethylammonium hydroxide aqueous solution were added with stirring.
- T1 titanium oxide-containing core particle (abbreviated as T1)> Put 126.2 g of pure water in a 1 liter container, 17.8 g of metastannic acid (containing 15 g in terms of SnO 2 ), 284 g of titanium tetraisopropoxide (containing 80 g in terms of TiO
- the obtained mixed solution had a molar ratio of oxalic acid / titanium atom of 0.78 and a molar ratio of tetraethylammonium hydroxide / titanium atom of 1.04.
- 950 g of the mixed solution was kept at 80 ° C. for 2 hours, and further reduced in pressure to 580 Torr and kept for 2 hours to prepare a titanium mixed solution.
- the prepared titanium mixed solution had a pH of 4.7 and a TiO 2 concentration of 8.4% by mass.
- Into a 3 liter glass-lined autoclave container 950 g of the titanium mixed solution and 950 g of pure water were added, and hydrothermal treatment was performed at 140 ° C. for 5 hours.
- the hydrothermally treated solution taken out was a light milky white colloidal titanium oxide aqueous dispersion sol.
- the obtained sol had a pH of 3.9, a TiO 2 concentration of 4.2% by mass, tetraethylammonium hydroxide of 4.0% by mass, oxalic acid of 1.8% by mass, a dynamic light scattering particle diameter of 16 nm, and a transmission electron microscope. In the observation, elliptical particles having a primary particle diameter of 5 to 15 nm were observed.
- the powder obtained by drying the obtained sol at 110 ° C. was subjected to X-ray diffraction analysis, and was confirmed to be a rutile crystal.
- the obtained titanium oxide colloidal particles were used as titanium oxide-containing core particles (B1).
- the obtained sol was an aqueous dispersion sol of alkaline silicon dioxide-stannic acid composite oxide colloidal particles, and was a colloidal particle sol having a pH of 8.2 and a primary particle diameter of 5 nm or less.
- the obtained silicon dioxide-stannic acid composite oxide colloidal particles were used as a coating (B2).
- 570 g of a coating made of colloidal particles of silicon dioxide-stannic acid composite oxide (B2) is added to 1900 g of titanium oxide-containing core particles (B1) under stirring, and then maintained at 95 ° C. for 3 hours to obtain modified titanium oxide.
- An aqueous sol of composite colloidal particles was obtained.
- the obtained aqueous sol of the modified titanium oxide composite colloidal particles is passed through a column packed with a hydrogen-type cation exchange resin (Amberlite (registered trademark) IR-120B, Organo Corp.), and the acidic modified titanium oxide 2730 g of an aqueous sol of composite colloidal particles was obtained.
- a hydrogen-type cation exchange resin Amberlite (registered trademark) IR-120B, Organo Corp.
- the obtained sol had a pH of 2.7 and a total metal oxide concentration of 4.0% by mass. 2.2 g of diisobutylamine was added to the obtained sol. The pH of the sol at this time was 4.5. Next, the obtained sol was put into an evaporator with an eggplant-shaped flask and concentrated, and water was distilled off at 600 Torr while adding methanol, whereby 533 g of methanol sol of modified titanium oxide colloidal particles (B3) bonded with diisobutylamine was added. Got.
- the obtained methanol sol had a specific gravity of 0.949, a viscosity of 1.2 mPa ⁇ s, a pH of 4.8 (diluted with the same amount of water as the sol), a total metal oxide concentration of 20.5% by mass, and a water content of 3.1%. there were.
- methanol was distilled off while adding propylene glycol monomethyl ether at 80 Torr using an evaporator, so that methanol was replaced with propylene glycol monomethyl ether, and the modified titanium oxide colloidal particles having polyether-modified silane bonded to the surface thereof.
- 270 g of propylene glycol monomethyl ether dispersion sol was obtained.
- the obtained sol had a specific gravity of 1.353, a viscosity of 7.0 mPa ⁇ s, a total metal oxide concentration of 40.3% by mass, a primary particle diameter of 5 to 10 nm as observed with a transmission electron microscope, and a dynamic light scattering particle diameter. was 9 nm.
- the polyether-modified silane bonded to the surface of the modified titanium oxide colloidal particles was 4.0% by mass with respect to the modified titanium oxide colloidal particles. Subsequently, it concentrated using an evaporator so that it might become 52 mass% in conversion of the solid residue in 140 degreeC, and obtained the metal oxide sol (T1) of (B) component.
- a dispersion sol of titanium oxide-containing core particles (abbreviated as T2) was prepared as follows. ⁇ Preparation of metal oxide colloidal particles> Put 126.2 g of pure water in a 1 liter container, 17.8 g of metastannic acid (containing 15 g in terms of SnO 2 ), 284 g of titanium tetraisopropoxide (containing 80 g in terms of TiO 2 ), 84 g of oxalic acid dihydrate ( 70 g in terms of oxalic acid) and 438 g of a 35 mass% tetraethylammonium hydroxide aqueous solution were added with stirring.
- the obtained mixed solution had a molar ratio of oxalic acid / titanium atom of 0.78 and a molar ratio of tetraethylammonium hydroxide / titanium atom of 1.04.
- 950 g of the mixed solution was kept at 80 ° C. for 2 hours, and further reduced in pressure to 580 Torr and kept for 2 hours to prepare a titanium mixed solution.
- the prepared titanium mixed solution had a pH of 4.7 and a TiO 2 concentration of 8.4% by mass.
- Into a 3 liter glass-lined autoclave container 950 g of the titanium mixed solution and 950 g of pure water were added, and hydrothermal treatment was performed at 140 ° C. for 5 hours.
- the solution after the hydrothermal treatment taken out was an aqueous sol of pale milky white titanium oxide colloidal particles.
- the obtained sol had a pH of 3.9, a TiO 2 concentration of 4.2% by mass, tetraethylammonium hydroxide of 4.0% by mass, oxalic acid of 1.8% by mass, a dynamic light scattering particle diameter of 16 nm, and a transmission electron microscope. In the observation, elliptical particles having a primary particle diameter of 5 to 15 nm were observed.
- the powder obtained by drying the obtained sol at 110 ° C. was subjected to X-ray diffraction analysis, and was confirmed to be a rutile crystal.
- the obtained sodium silicate silicate aqueous solution (64.4 g) was diluted with pure water (411 g) and passed through a column filled with a hydrogen-type cation exchange resin (Amberlite (registered trademark) IR-120B).
- aqueous sol of stannic acid composite oxide colloidal particles (pH 2.7, 0.83% by mass as SnO 2, containing 1.67% by mass as SiO 2, SiO 2 / SnO 2 mass ratio of 2.0) was obtained 570g .
- 2.9 g of diisopropylamine was added to the obtained aqueous sol.
- the obtained sol was an aqueous sol of alkaline silicon dioxide-stannic acid composite oxide colloidal particles, and was colloidal particles having a pH of 8.2 and a primary particle diameter of 5 nm or less.
- the obtained silicon dioxide-stannic acid composite oxide colloidal particles were used as a coating.
- 570 g of a coating composed of silicon dioxide-stannic acid composite oxide colloidal particles is added to 1900 g of an aqueous sol of titanium oxide-containing core particles under stirring, and then maintained at 95 ° C. for 3 hours, and modified titanium oxide composite colloidal particles An aqueous sol was obtained.
- the obtained aqueous sol of the modified titanium oxide composite colloidal particles is passed through a column packed with a hydrogen-type cation exchange resin (Amberlite (registered trademark) IR-120B, Organo Corp.), and the acidic modified titanium oxide 2730 g of an aqueous sol of composite colloidal particles was obtained.
- a hydrogen-type cation exchange resin Amberlite (registered trademark) IR-120B, Organo Corp.
- the obtained sol had a pH of 2.7 and a total metal oxide concentration of 4.0% by mass. 2.2 g of diisobutylamine was added to the obtained sol. The pH of the sol at this time was 4.5. Next, the obtained sol was put into an evaporator with an eggplant-shaped flask and concentrated, and water was distilled off at 600 Torr while adding methanol to obtain 364 g of methanol-dispersed sol of modified titanium oxide colloidal particles.
- the obtained methanol-dispersed sol has a specific gravity of 1.062, a viscosity of 1.8 mPa ⁇ s, a pH of 4.8 (diluted with water of the same mass as the sol), a total metal oxide concentration of 30.5% by mass, and a water content of 1.0%. Met. Subsequently, it concentrated using an evaporator so that it might become 52 mass% in conversion of the solid residue in 140 degreeC, and metal oxide sol (T2) was obtained.
- SV1 and SV1C each measured an initial viscosity, subjected to a 30-day standing test at 23 ° C., and measured the viscosity after 30 days.
- SV1 or SV1C is spin-coated on a silicon substrate or quartz substrate at 1000 rpm for 30 seconds using a spin coater, then baked at 80 ° C. for 1 minute and then at 230 ° C. for 5 minutes using a hot plate.
- the film thickness and the refractive index at a wavelength of 550 nm were measured using an ellipsometer, and the transmittance was measured in the film obtained on the quartz substrate, and the average of 400 nm to 800 nm was measured. The transmittance was calculated. Moreover, in the film obtained on the silicon substrate, it was tested whether whitening and a crack were confirmed visually. When whitening or a crack occurred, it was judged as x.
- Example 2 A film-forming composition (SV2) was similarly prepared except that S1 of Example 1 was changed to S2, and SV2 was further heated in the same manner to obtain a film-forming composition SV2C.
- SV2 and SV2C the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 3 A film-forming composition (SV3) was similarly prepared except that S1 of Example 1 was changed to S3, and SV3 was further heated in the same manner to obtain a film-forming composition SV3C.
- the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 4 A film-forming composition (SV4) was similarly prepared except that S1 of Example 1 was changed to S4, and SV4 was heated in the same manner to obtain a film-forming composition SV4C.
- SV2 and SV2C the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 5 A film-forming composition (SV5) was similarly prepared except that S1 in Example 1 was changed to S5, and SV5 was further heated in the same manner to obtain a film-forming composition SV5C.
- the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 6 A film-forming composition (SV6) was similarly prepared except that S1 of Example 1 was changed to S6, and SV6 was further heated in the same manner to obtain a film-forming composition SV6C.
- SV2 and SV2C the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 7 A film-forming composition (SV7) was similarly prepared except that S1 of Example 1 was changed to S7, and SV7 was further heated in the same manner to obtain a film-forming composition SV7C.
- the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 8 A film-forming composition (SV8) was prepared in the same manner except that S1 in Example 1 was changed to S8, and SV8 was further heated in the same manner to obtain a film-forming composition SV8C.
- SV8C the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 9 A film-forming composition (SV9) was similarly prepared except that S1 in Example 1 was changed to S9, and SV9 was further heated in the same manner to obtain a film-forming composition SV9C.
- the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 10 A film-forming composition (SV10) was similarly prepared except that S1 of Example 1 was changed to S10, and SV10 was further heated by the same method to obtain a film-forming composition SV10C.
- S1 of Example 1 was changed to S10
- SV10 was further heated by the same method to obtain a film-forming composition SV10C.
- the viscosity was measured and the coating was prepared and evaluated in the same procedure as in Example 1.
- Example 11 In a 20 mL eggplant-shaped flask, 15.00 g of T1 obtained in Synthesis Example 13 was weighed, then 0.31 g of PGME and 0.47 g of ⁇ -butyllactone were added, and 3.01 g of S1 obtained in Synthesis Example 1 was added. 0.06 g of BYK-307 as an activator was added and mixed at room temperature to prepare a film-forming composition (SV11) having a solid content concentration of 50 mass% when fired at 140 ° C. About obtained SV11, it heated by the method similar to the above, and composition for film formation SV11C was obtained. For SV11 and SV11C, the viscosity was measured and the production and evaluation of the coating were carried out in the same procedure as in Example 1.
- Table 1 shows the results of film thickness, refractive index, transmittance, viscosity, storage stability of viscosity, whitening, and presence of cracks.
- a film-forming composition (RV2) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S2, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV3) was similarly prepared except that S1 in Comparative Example 1 was changed to S3, and the viscosity was measured.
- a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV4) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S4, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV5) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S5, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV6) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S6, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV7) was similarly prepared except that S1 in Comparative Example 1 was changed to S7, and the viscosity was measured. A film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV8) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S8, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV9) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S9, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- a film-forming composition (RV10) was prepared in the same manner except that S1 in Comparative Example 1 was changed to S10, the viscosity was measured, and a film was obtained and evaluated in the same manner as in Comparative Example 1.
- the film mounted on the electronic device is required not to be whitened or cracked. Moreover, as a film forming composition, it is requested
- the coating formed of the coating forming composition of the present invention did not cause whitening or cracking even with a thick film of about 3 ⁇ m.
- Comparative Examples 1 to 10 whitening and cracks occurred in the obtained films, and the film thickness, refractive index, and transmittance were not measured.
- the film-forming composition of the present invention does not change in viscosity even when stored at 23 ° C. for 30 days. There was almost no change in viscosity even after heating, and good storage stability was shown.
- the film-forming compositions of Comparative Examples 1 to 10 were poor in storage stability, such as the viscosity changed with time and increased greatly during storage at 23 ° C., and some gelled.
- the coatings obtained in Examples 1 to 11 have a refractive index at a wavelength of 550 nm of around 1.85, an average transmittance of a wavelength of 400 nm to 800 nm is 95% or more, and a coating film having a high refractive index and high transparency can be obtained. It was.
- Example 11 A film-forming composition was prepared in the same manner as in Example 1 except that S1 of Example 1 was changed to R1 obtained in Synthesis Example 11, but a solid was precipitated in the film-forming composition and was uniform. A film forming composition could not be obtained.
- Example 12 A film-forming composition was prepared in the same manner except that S1 of Example 1 was changed to R2 obtained in Synthesis Example 12, but a solid was deposited in the film-forming composition and a uniform film-forming composition was obtained. The thing was not obtained.
- [3] Heating condition of film forming composition As described above, when the film forming composition of the present invention is subjected to a heating step, a film having a uniform film quality may be obtained. For this reason, 10 g of the film-forming composition was weighed in a 20 mL eggplant-shaped flask, and the heating step was carried out under various heating conditions to examine the stability of the film-forming composition.
- Example 12 to Example 31, Example 32 to Example 36 SV1 to SV10 were heated for 1 hour using an oil bath set at 110 ° C., 150 ° C., and 160 ° C., and the film forming composition was observed. There was no deposit in each film forming composition, and a uniform film forming composition without gelation was obtained.
- the film forming composition was observed by heating for 1 hour using an oil bath in which SV1 to SV10 were set to 170 ° C. A needle-like crystal component was precipitated in each film forming composition, and a uniform film forming composition was not obtained.
- the film-forming composition of the present invention did not generate acicular crystals under any heating conditions of 150 ° C. or lower, and a uniform film-forming composition was obtained. That is, it was confirmed that the film-forming composition of the example was appropriately subjected to a heating step under a temperature condition of 150 ° C. or lower.
- any film-forming composition had acicular crystals deposited, and a uniform film-forming composition could not be obtained.
- Comparative Examples 13 to 27 when needle-like crystals are generated in the film-forming composition, the dispersion state of the particles in the film-forming composition changes, and the desired film cannot be obtained. It is not preferable.
- the film forming composition of the present invention retains the high dispersibility of the inorganic fine particles, the storage stability of the film forming composition is good and the product life is long. Is possible.
- the film-forming composition of the present invention is an electronic device such as a liquid crystal display, an organic electroluminescence (OLED) display, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, a dye-sensitized solar cell, and an organic thin film transistor (TFT). It can be suitably used as a member for manufacturing a device. Moreover, it can utilize suitably as a member for lenses by which high refractive index is calculated
- a buried film and a planarizing film on a photodiode, a planarizing film before and after a color filter, a microlens, a planarizing film and a conformal film on a microlens, which are members of a solid-state imaging device that requires a high refractive index. can be suitably used.
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Abstract
Description
1.(A)成分:下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解縮合物、及び
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子
を含む被膜形成用組成物、
2.前記式(1)中のR2は、メチル基、エチル基、フェニル基、ビフェニル基又はフェナントリル基であり、aは1である、1に記載の被膜形成用組成物、
3.前記両親媒性の有機ケイ素化合物は、その親水性基中の前記オキシアルキレン基の付加モル数が3~40モルの化合物である、1又は2に記載の被膜形成用組成物、
4.前記(B)成分の変性金属酸化物コロイド粒子(B3)の表面に結合された両親媒性を有する有機ケイ素化合物が、変性金属酸化物コロイド粒子(B3)の全金属酸化物に対して3~30質量%の質量割合にて結合してなる、1~3のいずれか一つに記載の被膜形成用組成物、
5.前記(B)成分の金属酸化物コロイド粒子(B1)が、Ti、Fe、Cu、Zn、Y、Zr、Nb、Mo、In、Sn、Sb、Ta、W、Pb、Bi及びCeからなる群から選ばれる少なくとも1種の金属の酸化物である、1~4のいずれか一つに記載の被膜形成用組成物、
6.前記(B)成分の被覆物(B2)が、Si、Al、Sn、Zr、Mo、Sb及びWからなる群から選ばれる少なくとも1種の金属の酸化物である、1~5のいずれか一つに記載の被膜形成用組成物、
7.(A)成分:下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解縮合物と
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子
とを混合する工程を含む、被膜形成用組成物の製造方法、
8.前記式(1)中のR2は、メチル基、エチル基、フェニル基、ビフェニル基又はフェナントリル基であり、aは1である、7に記載の被膜形成用組成物の製造方法、
9.前記両親媒性の有機ケイ素化合物は、その親水性基中の前記オキシアルキレン基の付加モル数が3~40モルの化合物である、7又8に記載の被膜形成用組成物の製造方法、
10.前記(A)成分と前記(B)成分とを混合する工程の後、23℃以上150℃以下で加熱する工程を含む、7~9のいずれか一つに記載の被膜形成用組成物の製造方法、
11.1~6のいずれか一つに記載の被膜形成用組成物から得られる被膜、
12.基材と、この基材上に形成された11に記載の被膜とを備える電子デバイス、
13.基材と、この基材上に形成された11に記載の被膜とを備える光学部材、
14.11に記載の被膜を少なくとも1層備える、相補性金属酸化膜半導体を有する固体撮像素子又は電荷結合素子、
15.11に記載の被膜を少なくとも1層備える、固体撮像素子用埋め込み材料、平坦化材料、又はマイクロレンズ材料、
を提供する。
で表される少なくとも1種の加水分解性シランの加水分解縮合物と
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子とを混合した被膜形成用組成物より被膜を形成した場合、耐熱性及び透明性が高い被膜が得られ、電子デバイスに搭載した際の長期信頼性を高められる。
本願発明の被膜形成用組成物に含まれる(A)成分の加水分解性シランの加水分解縮合物とは、下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解物において、そのシラノール基同士が脱水縮合を起こし、ポリシロキサンを形成したものである。
具体的には、あらかじめアルコール(有機溶媒)にシュウ酸(加水分解用触媒)及び水を加えてシュウ酸の溶液とした後、当該溶液と加水分解性シラン化合物とを混合し、加熱する方法である。その際、シュウ酸の量は、加水分解性シラン化合物が有する全加水分解基(アルコキシ基等)1モルに対して0.2~2モルとすることが一般的である。この方法における加熱は、液温50~180℃で行うことができ、好ましくは、液の蒸発、揮散等が起こらないように、例えば、密閉容器中の還流下で10分から12時間行われる。
また、加水分解性シランの加水分解縮合物の製造手順は、加水分解性シラン化合物に有機溶媒、水及び加水分解用触媒の混合物を加え、反応させる順序であっても、有機溶媒、水及び加水分解用触媒の混合物中に加水分解性シラン化合物を加え、反応させる順序であってもよい。
加水分解性シランの加水分解縮合物を合成する際の反応温度は、均一なポリマーを安定して合成する目的で0~50℃の反応温度であればよく、反応時間は24~2000時間で行うことができる。
中でも上記有機溶媒としては、一般に加水分解反応によりアルコールが生成するため、アルコール類やアルコール類と相溶性の良好な有機溶媒が用いることが好適である。このような有機溶媒の具体例としては、特にメタノール、エタノール、n-プロパノール、イソプロパノール、n-ブタノール、メチルエチルケトン、エチ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エチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールプロピルエーテル、n-プロピルアセテート、乳酸エチル、シクロヘキサノン等が好ましく挙げられる。
本願発明の被膜形成用組成物に含まれる(B)成分の無機微粒子とは、2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている、無機微粒子である。
例えば、金属酸化物コロイド粒子(B1)を含有する水性ゾルと、被覆物(B2)としてSb2O5/SiO2の質量割合で0.1~5であるSb2O5-SiO2複合コロイド粒子を含有する水性ゾルとを、各々の金属酸化物に換算した(B2)/(B1)の質量割合で0.05~0.5となるように混合し、当該混合ゾルを70~350℃で加熱することにより、金属酸化物コロイド粒子(B1)を核として、その表面をSb2O5-SiO2複合コロイド粒子(B2)で被覆した粒子(B3)からなる変性金属酸化物ゾルが得られる。
例えば、金属酸化物コロイド粒子(B1)を含有する水性ゾルと、被覆物(B2)として、スズ酸ナトリウムと珪酸ナトリウムの水溶液を混合した後に陽イオン交換することで得られるSnO2-SiO2複合コロイド粒子の水性ゾルとを、各々の金属酸化物に換算した(SnO2-SiO2)/(B2)の質量割合で0.05~0.5となるように混合し、当該水性ゾルを70~350℃で加熱することにより、金属酸化物コロイド粒子(B1)を核として、その表面をSnO2-SiO2複合コロイド粒子からなる被覆物(B2)で被覆された変性金属酸化物コロイド粒子(B3)の水性ゾルが得られる。
本願発明はまた、(A)成分:下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解縮合物と
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子
とを混合する工程を含む、被膜形成用組成物の製造方法を対象とする。
(a)前記(A)成分を固体状態で前記(B)成分の分散液に混合させる方法、
(b)前記(A)成分を有機溶媒等に溶解・分散させた液の状態で前記(B)成分の分散液に混合させる方法、
(c)前記(A)成分を固体状態で、前記(B)成分を分散媒に分散させる工程で、同時に添加して混合させる方法、が挙げられる。
これらの中でも操作が容易であることから、(b)の方法で混合させることが好ましい。
[GPC]
装置:東ソー(株)製 HLC-8200 GPC
カラム:Shodex KF-804L+KF-805L
カラム温度:40℃
溶媒:テトラヒドロフラン(以下、THF)
検出器:UV(254nm)
検量線:標準ポリスチレン
[紫外線可視分光光度計]
装置:(株)島津製作所製 SHIMADZU UV-3600
[エリプソメーター]
装置:ジェー・エー・ウーラム・ジャパン(株)製 多入射角分光エリプソメーターVASE
[粘度]
装置:東機産業(株)社製 E型粘度計(20℃)
[電子顕微鏡]
装置:株式会社日立ハイテクノロジーズ社製 S-4800
29.17g(0.14mol)のテトラエトキシシラン、116.66gのプロピレングリコールモノメチルエーテル(以下、PGMEと略す。)を300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01モル/Lの塩酸10.09gを混合溶液に滴下した。添加後、100℃に調整されたオイルバスにフラスコを移し、加熱還流下で240分間反応させた。その後、反応溶液を室温まで冷却し、反応溶液に116.66gのPGMEを加え、反応副生物であるエタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)のPGME溶液を得た。次いで、140℃における固形残物換算で52質量%となるようにPGMEを加え調整した。得られたポリマーはテトラエトキシシランを原料としたポリシロキサン(S1と略す。)のワニスである。得られたS1のGPCによる重量平均分子量はポリスチレン換算でMw1823であった。
合成例1の出発原料をテトラエトキシシランからトリエトキシフェニルシランに変更し、シランモノマーに対して3.0当量の純水を用いた以外は同様に合成し、ポリシロキサン(S2と略す。)を得た。重量平均分子量はMw1251であった。
合成例2の出発原料をトリエトキシフェニルシランから4-ビフェニルトリメトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S3と略す。)を得た。重量平均分子量はMw1546であった。
合成例2の出発原料をトリエトキシフェニルシランからメチルトリエトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S4と略す。)を得た。重量平均分子量はMw2979であった。
合成例2の出発原料をトリエトキシフェニルシランからエチルトリエトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S5と略す。)を得た。重量平均分子量はMw2744であった。
合成例2の出発原料をトリエトキシフェニルシランからプロピルトリエトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S6と略す。)を得た。重量平均分子量はMw2154であった。
合成例2の出発原料をトリエトキシフェニルシランからn-オクチルトリエトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S8と略す。)を得た。重量平均分子量はMw1371であった。
合成例2の出発原料をトリエトキシフェニルシランから9-フェナントリルトリメトキシシランに変更した以外は合成例1と同様に合成し、ポリシロキサン(S9と略す。)を得た。重量平均分子量はMw1521であった。
合成例1の出発原料をテトラエトキシシランからジメトキシジメチルシランに変更し、シランモノマーに対して2.0当量の純水を用いた以外は合成例1と同様に合成し、ポリシロキサン(S10と略す。)を得た。重量平均分子量はMw2516であった。
200mLの反応フラスコに、プロピレングリコールモノメチルエーテルアセテート(PGMEA)92gを仕込み、次いで、20gのメタクリル酸メチル、3gのアゾビスイソブチロニトリルを仕込み、撹拌しながら5分間窒素を流し込み窒素置換を行った。溶液中の溶質が完全に溶解したことを目視で確認後、内温100℃で12時間反応させた。次に、この反応液を、575gのメタノールに注ぎ、ポリマーを析出させた。得られた固体は減圧濾過で分取し、固体を50℃の減圧乾燥器で12時間乾燥させた。乾燥して得られたポリメタクリル酸メチル[R1]のGPCによるMwは3500であった。R1は140℃における固形残物換算で52質量%となるようにPGMEを加え溶解させ、ポリマー溶液を得た。
200mLの反応フラスコに、プロピレングリコールモノメチルエーテルアセテート(PGMEA)92gを仕込み、次いで、20gのスチレン、3gのアゾビスイソブチロニトリルを仕込み、撹拌しながら5分間窒素を流し込み窒素置換を行った。溶液中の溶質が完全に溶解したことを目視で確認後、内温100℃で12時間反応させた。次に、この反応液を、575gのメタノールに注ぎ、ポリマーを析出させた。得られたポリマーは減圧濾過で分取し、50℃の減圧乾燥器で12時間乾燥させた。乾燥して得られたポリスチレン[R2]のGPCによるMwは3810であった。R2は、140℃における固形残物換算で52質量%となるようにPGMEを加え溶解させ、ポリマー溶液を得た。
以下のようにして(B)成分の酸化チタン含有核粒子(T1と略す)分散ゾルを調製した。
<核粒子(B1)の調製>
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)、チタンテトライソプロポキシド284g(TiO2換算で80g含有)、シュウ酸二水和物84g(シュウ酸換算で70g)、35質量%水酸化テトラエチルアンモニウム水溶液438gを撹拌下に添加した。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、更に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、TiO2濃度8.4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コロイド粒子の水分散ゾルであった。得られたゾルは、pH3.9、TiO2濃度4.2質量%、水酸化テトラエチルアンモニウム4.0質量%、シュウ酸1.8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。得られたゾルを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コロイド粒子を酸化チタン含有核粒子(B1)とした。
次いで珪酸ナトリウム水溶液(3号珪曹、SiO2として34質量%含有、富士化学(株)製)27.9gを純水27.9gにて希釈を行った後、ここにスズ酸ナトリウム・3水和物(SnO2として55質量%含有、昭和化工(株)製)8.6gを添加し、撹拌下で溶解し、珪酸-スズ酸ナトリウムの水溶液を得た。得られた珪酸スズ酸ナトリウム水溶液64.4gを純水411gで希釈し、水素型陽イオン交換樹脂(アンバーライト(登録商標)IR-120B、オルガノ(株))を充填したカラムに通液することにより、二酸化ケイ素-スズ酸複合酸化物コロイド粒子の水分散ゾル(pH2.7、SnO2として0.83質量%、SiO2として1.67質量%を含有、SiO2/SnO2質量比2.0)570g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2.9g添加した。得られたゾルはアルカリ性の二酸化ケイ素-スズ酸複合酸化物コロイド粒子の水分散ゾルであり、pH8.2、一次粒子径5nm以下のコロイド粒子のゾルであった。得られた二酸化ケイ素-スズ酸複合酸化物コロイド粒子を被覆物(B2)とした。
次いで、撹拌下で酸化チタン含有核粒子(B1)1900gに二酸化ケイ素-スズ酸複合酸化物コロイド粒子からなる被覆物(B2)570gを添加した後、温度95℃で3時間保持し、変性酸化チタン複合コロイド粒子の水性ゾルを得た。その後、得られた変性酸化チタン複合コロイド粒子の水性ゾルを、水素型陽イオン交換樹脂(アンバーライト(登録商標)IR-120B、オルガノ(株))を充填したカラムに通し、酸性の変性酸化チタン複合コロイド粒子の水性ゾル2730gを得た。得られたゾルはpH2.7、全金属酸化物濃度は4.0質量%であった。得られたゾルにジイソブチルアミンを2.2g添加した。このときのゾルのpHは4.5であった。次いで得られたゾルをナス型フラスコ付きエバポレータに投入して濃縮し、メタノールを添加しながら600Torrで水を留去することにより、ジイソブチルアミンが結合した変性酸化チタンコロイド粒子(B3)のメタノールゾル533gを得た。得られたメタノールゾルは、比重0.949、粘度1.2mPa・s、pH4.8(ゾルと同質量の水で希釈)、全金属酸化物濃度20.5質量%、水分3.1%であった。
得られたメタノールゾル533gにポリエーテル変性シラン(3-[メトキシ(ポリエチレンオキシ)nプロピル]トリメトキシシラン(n=5~15);信越シリコーン製:商品名X-12-641)を5.5g添加し、還留加熱を5時間行い、ポリエーテル変性シランを変性酸化チタンコロイド粒子の表面に結合させた。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溶媒置換して、ポリエーテル変性シランが表面に結合した変性酸化チタンコロイド粒子のプロピレングリコールモノメチルエーテル分散ゾルが270g得られた。得られたゾルは比重1.353、粘度7.0mPa・s、全金属酸化物濃度40.3質量%、透過型電子顕微鏡観察による1次粒子径は5~10nm、動的光散乱法粒子径は9nmであった。変性酸化チタンコロイド粒子の表面に結合したポリエーテル変性シランは、変性酸化チタンコロイド粒子に対して4.0質量%であった。次いで、140℃における固形残物換算で52質量%となるようにエバポレータを用いて濃縮し、(B)成分の金属酸化物ゾル(T1)を得た。
以下のようにして酸化チタン含有核粒子(T2と略す)の分散ゾルを調製した。
<金属酸化物コロイド粒子の調製>
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)、チタンテトライソプロポキシド284g(TiO2換算で80g含有)、シュウ酸二水和物84g(シュウ酸換算で70g)、35質量%水酸化テトラエチルアンモニウム水溶液438gを撹拌下に添加した。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、更に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、TiO2濃度8.4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コロイド粒子の水性ゾルであった。得られたゾルは、pH3.9、TiO2濃度4.2質量%、水酸化テトラエチルアンモニウム4.0質量%、シュウ酸1.8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。得られたゾルを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。
次いで珪酸ナトリウム水溶液(3号珪曹、SiO2として34質量%含有、富士化学(株)製)27.9gを純水27.9gにて希釈を行った後、スズ酸ナトリウム・3水和物(SnO2として55質量%含有、昭和化工(株)製)8.6gを添加し、撹拌下で溶解し、珪酸-スズ酸ナトリウムの水溶液を得た。得られた珪酸スズ酸ナトリウム水溶液64.4gを純水411gで希釈し、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することにより、二酸化ケイ素-スズ酸複合酸化物コロイド粒子の水性ゾル(pH2.7、SnO2として0.83質量%、SiO2として1.67質量%を含有、SiO2/SnO2質量比2.0)570gを得た。次いで、得られた水性ゾルにジイソプロピルアミンを2.9g添加した。得られたゾルはアルカリ性の二酸化ケイ素-スズ酸複合酸化物コロイド粒子の水性ゾルであり、pH8.2、一次粒子径5nm以下のコロイド粒子であった。得られた二酸化ケイ素-スズ酸複合酸化物コロイド粒子を被覆物とした。
次いで、撹拌下で酸化チタン含有核粒子の水性ゾル1900gに二酸化ケイ素-スズ酸複合酸化物コロイド粒子からなる被覆物570gを添加した後、温度95℃で3時間保持し、変性酸化チタン複合コロイド粒子の水性ゾルを得た。その後、得られた変性酸化チタン複合コロイド粒子の水性ゾルを、水素型陽イオン交換樹脂(アンバーライト(登録商標)IR-120B、オルガノ(株))を充填したカラムに通し、酸性の変性酸化チタン複合コロイド粒子の水性ゾル2730gを得た。得られたゾルはpH2.7、全金属酸化物濃度は4.0質量%であった。得られたゾルにジイソブチルアミンを2.2g添加した。このときのゾルのpHは4.5であった。次いで得られたゾルをナス型フラスコ付きエバポレータに投入して濃縮し、メタノールを添加しながら600Torrで水を留去することにより、変性酸化チタンコロイド粒子のメタノール分散ゾル364gを得た。
得られたメタノール分散ゾルは、比重1.062、粘度1.8mPa・s、pH4.8(ゾルと同質量の水で希釈)、全金属酸化物濃度30.5質量%、水分1.0%であった。次いで、140℃における固形残物換算で52質量%となるようにエバポレータを用いて濃縮し、金属酸化物ゾル(T2)を得た。
[実施例1]
(SV1の調製)
20mLナス型フラスコに合成例13で得られた15.00gのT1を秤量し、次いで、PGME1.5676gを加え、合成例1で得たS1を3.00g加え、室温にて混合して、140℃焼成時の固形分濃度48質量%の被膜形成用組成物(SV1)を調製した。
(SV1Cの調製)
20mLナス型フラスコにSV1を10.00g秤量し、オイルバスを用いて80℃で1時間加熱した。加熱後、内温が23℃になるまで放冷し、加熱後の被膜形成用組成物SV1Cを得た。
SV1及びSV1Cは、それぞれ初期粘度を測定し、23℃で30日間放置試験を行い、30日後の粘度を測定した。
(被膜の作製及び評価)
SV1又はSV1Cを、シリコン基板又は石英基板上に、スピンコーターを用いて1000rpmで30秒スピンコートし、次いでホットプレートを用いて80℃で1分間、続いて230℃で5分間焼成を行い、被膜を得た。
シリコン基板上に得られた被膜において、エリプソメーターを用いて、膜厚と、波長550nmの屈折率を測定し、石英基板上に得られた膜において、透過率を測定し、400nm~800nmの平均透過率を算出した。
またシリコン基板上に得られた被膜において、目視で白化とクラックが確認されるかを試験した。白化やクラックが発生した場合は×、発生しない場合は〇として判定した。
実施例1のS1をS2に変更した以外は同様に被膜形成用組成物(SV2)を調製し、さらに同様の方法によりSV2を加熱し、被膜形成用組成物SV2Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例3]
実施例1のS1をS3に変更した以外は同様に被膜形成用組成物(SV3)を調製し、さらに同様の方法によりSV3を加熱し、被膜形成用組成物SV3Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例4]
実施例1のS1をS4に変更した以外は同様に被膜形成用組成物(SV4)を調製し、さらに同様の方法によりSV4を加熱し、被膜形成用組成物SV4Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例5]
実施例1のS1をS5に変更した以外は同様に被膜形成用組成物(SV5)を調製し、さらに同様の方法によりSV5を加熱し、被膜形成用組成物SV5Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例6]
実施例1のS1をS6に変更した以外は同様に被膜形成用組成物(SV6)を調製し、さらに同様の方法によりSV6を加熱し、被膜形成用組成物SV6Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例7]
実施例1のS1をS7に変更した以外は同様に被膜形成用組成物(SV7)を調製し、さらに同様の方法によりSV7を加熱し、被膜形成用組成物SV7Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例8]
実施例1のS1をS8に変更した以外は同様に被膜形成用組成物(SV8)を調製し、さらに同様の方法によりSV8を加熱し、被膜形成用組成物SV8Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例9]
実施例1のS1をS9に変更した以外は同様に被膜形成用組成物(SV9)を調製し、さらに同様の方法によりSV9を加熱し、被膜形成用組成物SV9Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
[実施例10]
実施例1のS1をS10に変更した以外は同様に被膜形成用組成物(SV10)を調製し、さらに同様の方法によりSV10を加熱し、被膜形成用組成物SV10Cを得た。SV2及びSV2Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
20mLナス型フラスコに合成例13で得られた15.00gのT1を秤量し、次いで、PGME0.31g、γ-ブチルラクトン0.47gを加え、合成例1で得たS1を3.00g、界面活性剤としてBYK-307を0.06g加え、室温にて混合して、140℃焼成時の固形分濃度50質量%の被膜形成用組成物(SV11)を調製した。
得られたSV11について、上記と同様の方法により加熱し、被膜形成用組成物SV11Cを得た。
SV11及びSV11Cについて、実施例1と同様の手順にて粘度測定、並びに被膜の作製及び評価を実施した。
20mLナス型フラスコに合成例14で得られた15.00gのT2を秤量し、次いで、PGME1.5676gを加え、合成例1で得たS1を3.00g加え、140℃焼成時の固形分濃度が48質量%の被膜形成用組成物(RV1)を調製した。
(粘度測定)
RV1は、初期粘度を測定し、23℃で30日間放置試験を行い、30日後の粘度を測定した。
(被膜の作製及び評価)
RV1を、シリコン基板にスピンコーターを用いて、1000rpmで30秒スピンコートし、ホットプレートを用いて、80℃で1分間、次いで230℃で5分間焼成を行い、被膜を得た。シリコン基板上に得た被膜において、目視で白化、クラックが確認されるかを試験した。白化やクラックが発生した場合は×、発生しない場合は〇として判定した。
比較例1のS1をS2に変更した以外は同様に被膜形成用組成物(RV2)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例3]
比較例1のS1をS3に変更した以外は同様に被膜形成用組成物(RV3)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例4]
比較例1のS1をS4に変更した以外は同様に被膜形成用組成物(RV4)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例5]
比較例1のS1をS5に変更した以外は同様に被膜形成用組成物(RV5)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例6]
比較例1のS1をS6に変更した以外は同様に被膜形成用組成物(RV6)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例7]
比較例1のS1をS7に変更した以外は同様に被膜形成用組成物(RV7)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例8]
比較例1のS1をS8に変更した以外は同様に被膜形成用組成物(RV8)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例9]
比較例1のS1をS9に変更した以外は同様に被膜形成用組成物(RV9)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
[比較例10]
比較例1のS1をS10に変更した以外は同様に被膜形成用組成物(RV10)を調製し、粘度を測定するとともに、比較例1と同様の方法で被膜を得、評価した。
また、被膜形成用組成物としては、室温保存時に粘度の経時変化がないことが要求される。これは、経時変化により被膜形成用組成物の粘度が増加すると、目的とする膜厚が得られなくなることを意味し、結果、製品の歩留まりが低下するためである。
また、初期粘度及び30日保管後の粘度にて評価される被膜形成用組成物の保存安定性に着目すると、本願発明の被膜形成用組成物は23℃において30日間保管しても粘度変化が殆どなく、また加熱後においても粘度が大きく変化せず、良好な保存安定性が示された。一方、比較例1~10の被膜形成用組成物は23℃での保管中に、粘度は経時変化し大きく増加し、ゲル化したものもあるなど、保存安定性が悪いものであった。
[比較例11]
実施例1のS1を合成例11で得たR1に変更した以外は実施例1と同様の方法により被膜形成用組成物を調製したが、被膜形成用組成物中に固体が析出し、均一な被膜形成用組成物が得られなかった。
実施例1のS1を合成例12で得たR2に変更した以外は同様の方法により被膜形成用組成物を調製したが、被膜形成用組成物中に固体が析出し、均一な被膜形成用組成物が得られなかった。
前述したとおり、本願発明の被膜形成用組成物は加熱工程を経た場合、均一な膜質の膜が得られる場合がある。このため、20mLナス型フラスコに10gの被膜形成用組成物を秤量し、種々の加熱条件にて加熱工程を実施し、被膜形成用組成物の安定性を検討した。
SV1~SV10を110℃若しくは150℃、160℃に設定したオイルバスを用いて1時間加熱し、被膜形成用組成物の観察を行った。各被膜形成用組成物中に析出物はなく、ゲル化もしていない均一な被膜形成用組成物が得られた。
[比較例13~比較例22]
SV1~SV10を170℃に設定したオイルバスを用いて1時間加熱し、被膜形成用組成物の観察を行った。各被膜形成用組成物中に針状の結晶成分が析出し、均一な被膜形成用組成物が得られなかった。
表中、均一な被膜形成用組成物が得られた場合は〇、針状結晶が発生し、均一な被膜形成用組成物が得られなかった場合は×の判定とした。
比較例13~27のように、被膜形成用組成物中に針状結晶が発生してしまうと、被膜形成用組成物中の粒子の分散状態が変化し、目的とする被膜が得られないため好ましくない。
Claims (15)
- (A)成分:下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解縮合物、及び
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子
を含む被膜形成用組成物。 - 前記式(1)中のR2は、メチル基、エチル基、フェニル基、ビフェニル基又はフェナントリル基であり、aは1である、請求項1に記載の被膜形成用組成物。
- 前記両親媒性の有機ケイ素化合物は、その親水性基中の前記オキシアルキレン基の付加モル数が3~40モルの化合物である、請求項1又は2に記載の被膜形成用組成物。
- 前記(B)成分の変性金属酸化物コロイド粒子(B3)の表面に結合された両親媒性の有機ケイ素化合物が、変性金属酸化物コロイド粒子(B3)の全金属酸化物に対して0.1~30質量%の質量割合にて結合してなる、請求項1~3のいずれか一項に記載の被膜形成用組成物。
- 前記(B)成分の金属酸化物コロイド粒子(B1)が、Ti、Fe、Cu、Zn、Y、Zr、Nb、Mo、In、Sn、Sb、Ta、W、Pb、Bi及びCeからなる群から選ばれる少なくとも1種の金属の酸化物である、請求項1~4のいずれか一項に記載の被膜形成用組成物。
- 前記(B)成分の被覆物(B2)が、Si、Al、Sn、Zr、Mo、Sb及びWからなる群から選ばれる少なくとも1種の金属の酸化物である、請求項1~5のいずれか一項に記載の被膜形成用組成物。
- (A)成分:下記式(1)
で表される少なくとも1種の加水分解性シランの加水分解縮合物と
(B)成分:2~60nmの一次粒子径を有する金属酸化物コロイド粒子(B1)を核として、その表面を1~4nmの一次粒子径を有する金属酸化物コロイド粒子からなる被覆物(B2)で被覆された2~100nmの一次粒子径を有する変性金属酸化物コロイド粒子(B3)の表面に、親水性基としてポリオキシエチレン基、ポリオキシプロピレン基又はポリオキシブチレン基から選択される1種以上のポリ(オキシアルキレン)基を有し、疎水性基として炭素原子数1~18のアルキレン基又はビニレン基から選択される1種以上の基を有する両親媒性の有機ケイ素化合物が結合されている無機微粒子
とを混合する工程を含む、被膜形成用組成物の製造方法。 - 前記式(1)中のR2は、メチル基、エチル基、フェニル基、ビフェニル基又はフェナントリル基であり、aは1である、請求項7に記載の被膜形成用組成物の製造方法。
- 前記両親媒性の有機ケイ素化合物は、その親水性基中の前記オキシアルキレン基の付加モル数が3~40モルの化合物である、請求項7又8に記載の被膜形成用組成物の製造方法。
- 前記(A)成分と前記(B)成分とを混合する工程の後、
23℃以上150℃以下で加熱する工程を含む、請求項7~9のいずれか一項に記載の被膜形成用組成物の製造方法。 - 請求項1~6のいずれか一項に記載の被膜形成用組成物から得られる被膜。
- 基材と、この基材上に形成された請求項11に記載の被膜とを備える電子デバイス。
- 基材と、この基材上に形成された請求項11に記載の被膜とを備える光学部材。
- 請求項11に記載の被膜を少なくとも1層備える、相補性金属酸化膜半導体を有する固体撮像素子又は電荷結合素子。
- 請求項11に記載の被膜を少なくとも1層備える、固体撮像素子用埋め込み材料、平坦化材料、又はマイクロレンズ材料。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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US16/089,562 US10676643B2 (en) | 2016-03-31 | 2017-03-27 | Coating film-forming composition and process for producing the same |
KR1020187025159A KR102385050B1 (ko) | 2016-03-31 | 2017-03-27 | 피막형성용 조성물 및 그 제조방법 |
EP17774922.3A EP3438053A4 (en) | 2016-03-31 | 2017-03-27 | FILM-FORMING COMPOSITION AND PROCESS FOR PRODUCING THE SAME |
JP2018507981A JP6813809B2 (ja) | 2016-03-31 | 2017-03-27 | 被膜形成用組成物及びその製造方法 |
CN201780014240.9A CN108698851B (zh) | 2016-03-31 | 2017-03-27 | 被膜形成用组合物及其制造方法 |
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KR20230033466A (ko) * | 2021-09-01 | 2023-03-08 | 주식회사 한솔케미칼 | 돔 형상이 가능한 경화성 실리콘 조성물 및 그 경화물 |
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JPWO2017170385A1 (ja) | 2019-03-22 |
EP3438053A4 (en) | 2020-01-15 |
CN108698851B (zh) | 2020-11-10 |
JP6813809B2 (ja) | 2021-01-13 |
CN108698851A (zh) | 2018-10-23 |
KR20180132619A (ko) | 2018-12-12 |
TW201808811A (zh) | 2018-03-16 |
US20190144707A1 (en) | 2019-05-16 |
EP3438053A1 (en) | 2019-02-06 |
TWI805546B (zh) | 2023-06-21 |
KR102385050B1 (ko) | 2022-04-11 |
US10676643B2 (en) | 2020-06-09 |
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