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WO2011125646A1 - Composition de résine durcissable et dispositif électroluminescent - Google Patents

Composition de résine durcissable et dispositif électroluminescent Download PDF

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Publication number
WO2011125646A1
WO2011125646A1 PCT/JP2011/057793 JP2011057793W WO2011125646A1 WO 2011125646 A1 WO2011125646 A1 WO 2011125646A1 JP 2011057793 W JP2011057793 W JP 2011057793W WO 2011125646 A1 WO2011125646 A1 WO 2011125646A1
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Prior art keywords
group
component
resin composition
curable resin
mass
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English (en)
Japanese (ja)
Inventor
幸勇 前田
麗 高柳
至郎 高橋
宣康 篠原
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JSR Corp
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JSR Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/4805—Shape
    • H01L2224/4809—Loop shape
    • H01L2224/48091—Arched
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L2224/85—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a wire connector
    • H01L2224/85909—Post-treatment of the connector or wire bonding area
    • H01L2224/8592—Applying permanent coating, e.g. protective coating
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/852—Encapsulations
    • H10H20/854—Encapsulations characterised by their material, e.g. epoxy or silicone resins

Definitions

  • the present invention relates to a curable resin composition and a light-emitting device obtained using the same.
  • a light emitting device such as a light emitting diode (LED) is usually configured by covering a light emitting element with a sealing material in order to protect the light emitting element such as a light emitting diode (LED) element or to change a color. It is also known that the light extraction efficiency is increased by coating the light emitting element with a material having a high refractive index.
  • an epoxy resin is generally used as a material for the sealing material.
  • an epoxy resin (sealing material) in the vicinity of the light emitting element is caused by near ultraviolet light emitted from the blue LED element or ultraviolet light emitted from the ultraviolet LED element.
  • yellowing or thermal degradation due to heat generation of the light emitting element.
  • the amount of light emitted from blue LED elements and ultraviolet LED elements is large, and yellowing and thermal degradation are likely to occur.
  • a sealing material that does not cause yellowing due to near-ultraviolet light or ultraviolet light and hardly undergoes thermal deterioration for example, a sealing material made of a silicone resin made of dimethylsiloxane has been developed.
  • this sealing material has a low refractive index, and there is a problem that it is difficult to efficiently extract light emitted from the LED element.
  • Patent Documents 1 and 2 disclose a silicone resin composition containing a silicone resin having an alkenyl group bonded to a silicon atom and an organohydrogenpolysiloxane having a Si—H bond.
  • a silicone resin composition containing a silicone resin having an alkenyl group bonded to a silicon atom and an organohydrogenpolysiloxane having a Si—H bond.
  • this silicone resin composition is crosslinked by a hydrosilylation reaction, a cured product is obtained.
  • this cured product has a problem that the refractive index is low.
  • the present invention solves the above-described problems of the prior art, and has a high refractive index, excellent transparency, curable resin composition excellent in heat resistance, and light emission excellent in luminous efficiency.
  • An object is to provide an apparatus.
  • a curable resin composition containing a siloxane polymer having a specific structure and metal oxide particles such as zirconium oxide is a metal oxide particle.
  • the present invention has been completed by finding that it can be suitably used as a film material having excellent dispersibility, high refractive index, excellent transparency, and excellent heat resistance.
  • (a) A siloxane polymer obtained from a silane compound containing a compound represented by the following general formula (1): (R 1 ) p Si (X) 4-p (1) [In the general formula (1), R 1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms, X is a hydrolyzable group, and p is an integer of 0 to 3. ]
  • a curable resin composition having a content of 15 to 300% based on the number of atoms, and a blending amount of the component (B) of 50 to 2,000 parts by mass with respect to 100 parts by mass of the component (A).
  • a method for manufacturing a light emitting device comprising: a step of covering the light emitting element; and (b) a step of heating the light emitting element.
  • a light emitting element and (A) a siloxane polymer formed on the surface of the light emitting element and obtained from a silane compound containing a compound represented by the following general formula (1), (R 1 ) p Si (X) 4-p (1)
  • R 1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms
  • X is a hydrolyzable group
  • p is 0 to 3 It is an integer.
  • the metal oxide particles, the component (A) contains a silanol group, and the number of hydroxyl groups contained in the silanol group is based on the number of silicon atoms in the siloxane polymer.
  • a cured film which is a cured body of a curable resin composition having a content of 15 to 300% and a blending amount of the component (B) of 50 to 2,000 parts by mass with respect to 100 parts by mass of the component (A).
  • a light emitting device [3]
  • (A) A siloxane polymer obtained from a silane compound containing a compound represented by the following general formula (1): (R 1 ) p Si (X) 4-p (1)
  • R 1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms
  • X is a hydrolyzable group
  • p is an integer of 0 to 3.
  • a curable resin composition having a content of 15 to 300% based on the number of atoms, and a blending amount of the component (B) of 50 to 2,000 parts by mass with respect to 100 parts by mass of the component (A).
  • a siloxane-based polymer obtained from a silane compound containing a compound represented by the following general formula (1), which contains a silanol group, and the number of hydroxyl groups contained in the silanol group is the siloxane 100 parts by mass of a siloxane polymer that is 15 to 300% of the number of silicon atoms in the polymer and (B) 50 to 2,000 parts by mass of metal oxide particles in (C) an organic solvent
  • a method for producing a curable resin composition comprising mixing to produce the curable resin composition according to any one of [3] to [7].
  • R 1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms
  • X is a hydrolyzable group
  • p is an integer of 0 to 3.
  • the curable resin composition of the present invention has a high refractive index and is excellent in transparency, heat resistance, crack resistance and light resistance.
  • the curable resin composition of this invention is used suitably as a material for forming a cured film on the surface of a light emitting element.
  • a light emitting device in which a cured film, which is a cured body of the curable resin composition of the present invention, is formed on the surface of a light emitting element has high luminous efficiency.
  • FIG. 1 is a cross-sectional view conceptually showing an example of a light emitting device of the present invention.
  • the component (A) is a siloxane polymer obtained from a silane compound containing a compound represented by the following general formula (1).
  • (R 1 ) p Si (X) 4-p (1) (In the general formula (1), R 1 is a non-hydrolyzable organic group having 1 to 12 carbon atoms, X is a hydrolyzable group, and p is an integer of 0 to 3)
  • the hydrolyzable group represented by X in the general formula (1) is usually an alkoxy group by heating within the temperature range of room temperature (25 ° C.) to 100 ° C. in the presence of no catalyst and excess water.
  • the siloxane polymer contains a silanol group.
  • the number of hydroxyl groups contained in the silanol group is 15 to 300%, preferably 30 to 250%, more preferably 50 to 200%, based on the number of silicon atoms in the siloxane polymer.
  • the siloxane polymer may be one obtained by condensing at least two hydrolyzable silane compounds. In the siloxane polymer, an unhydrolyzed hydrolyzable group may partially remain.
  • the siloxane polymer may be a partial condensate in which some silanol groups or hydrolyzable groups are condensed.
  • the organic group R 1 in the general formula (1) is a non-hydrolyzable organic group having 1 to 12 carbon atoms.
  • the non-hydrolyzable property in the organic group R 1 means a property that exists stably as it is under the condition that the hydrolyzable group X is hydrolyzed.
  • Examples of the organic group R 1 include a hydrocarbon group having 1 to 12 carbon atoms and a halogenated hydrocarbon group having 1 to 12 carbon atoms.
  • the organic group R 1 may be linear, branched, cyclic, or a combination thereof.
  • the organic group R 1 may have a structural unit containing a hetero atom.
  • Examples of such a structural unit include an ether bond, an ester bond, a sulfide bond, and the like, and examples of the organic group R 1 containing such a bond include an epoxy group such as an oxetanyl group and an oxiranyl group. And a group having a (meth) acryloyloxy group.
  • the hydrocarbon group having 1 to 12 carbon atoms is preferably a hydrocarbon group having 1 to 8 carbon atoms from the viewpoint of reactivity and crack resistance of the resulting film. The hydrocarbon group is more preferable.
  • aliphatic hydrocarbon groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group and t-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl
  • aromatic hydrocarbon groups such as phenyl group, methylphenyl group, ethylphenyl group and benzyl group, such as methyl group, ethyl group, n-propyl group, isopropyl group, A t-butyl group, a phenyl group, and a methylphenyl group are preferable, and a methyl group and an ethyl group are more preferable.
  • Examples of the hydrocarbon group having 1 to 12 carbon atoms substituted with a halogen atom in the organic group R 1 include a fluorinated hydrocarbon group, a chlorinated hydrocarbon group, and a brominated hydrocarbon group. More preferably, it is a group.
  • the number of carbon atoms of the hydrocarbon group is preferably 1 to 4 from the viewpoint of reactivity and crack resistance of the resulting film.
  • the hydrolyzable group X in the general formula (1) is a hydrogen atom, a halogen atom, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, an acyloxy group having 2 to 12 carbon atoms, or a carbon number. Examples thereof include 2 to 12 halogenated acyloxy groups.
  • Preferable examples of the alkoxy group having 1 to 12 carbon atoms include methoxy group and ethoxy group.
  • Preferable examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
  • Preferable examples of the acyloxy group include an acetoxy group, a propionyloxy group, and a butyroyloxy group.
  • hydrolyzable silane compound represented by the general formula (1) (sometimes simply referred to as a silane compound) will be described.
  • the silane compounds having four hydrolyzable groups include tetrachlorosilane, tetraaminosilane, tetraacetoxysilane, tetramethoxysilane, tetraethoxysilane, tetrabutoxysilane, tetraphenoxysilane, tetrabenzyloxysilane, trimethoxysilane, trimethoxysilane, And ethoxysilane.
  • silane compounds having three hydrolyzable groups include methyltrichlorosilane, methyltrimethoxysilane, methyltriethoxysilane, methyltributoxysilane, ethyltrimethoxysilane, ethyltriisopropoxysilane, ethyltributoxysilane, butyl Examples thereof include trimethoxysilane, pentafluorophenyltrimethoxysilane, phenyltrimethoxysilane, d 3 -methyltrimethoxysilane, nonafluorobutylethyltrimethoxysilane, and trifluoromethyltrimethoxysilane.
  • silane compound having two hydrolyzable groups examples include dimethyldichlorosilane, dimethyldiaminosilane, dimethyldiacetoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, and dibutyldimethoxysilane.
  • silane compound having one hydrolyzable group examples include trimethylchlorosilane, hexamethyldisilazane, trimethylsilane, tributylsilane, trimethylmethoxysilane, and tributylethoxysilane.
  • the molecular weight of the siloxane polymer as the component (A) will be described. Such molecular weight can be measured as a weight average molecular weight in terms of polystyrene using gel permeation chromatography (hereinafter abbreviated as GPC) using tetrahydrofuran as a mobile phase.
  • GPC gel permeation chromatography
  • the weight average molecular weight of the siloxane polymer is preferably 500 to 100,000, more preferably 800 to 30,000, and still more preferably 1,000 to 5,000. If the value is less than 500, the crack resistance during the formation of the cured film tends to decrease. When the value exceeds 100,000, the dispersibility of the metal oxide particles as the component (B) tends to decrease.
  • Catalyst for obtaining a siloxane polymer is preferably at least one compound selected from a metal chelate compound, an acidic compound, and a basic compound, and is an acidic compound. It is more preferable.
  • (D-1) Metal Chelate Compound A metal chelate compound that can be used as a catalyst is represented by the following general formula (2).
  • R 15 e M (OR 16 ) fe (2) (Wherein R 15 represents a chelating agent, M represents a metal atom, R 16 represents an alkyl group or an aryl group, f represents a valence of metal M, and e represents an integer of 1 to f.)
  • the metal M is preferably at least one metal selected from Group IIIB metals (aluminum, gallium, indium, thallium) and Group IVA metals (titanium, zirconium, hafnium). Titanium, aluminum, zirconium Is more preferable.
  • the chelating agent represented by R 15 include CH 3 COCH 2 COCH 3 and CH 3 COCH 2 COOC 2 H 5 .
  • the alkyl group or aryl group represented by R 16 include the alkyl group or aryl group represented by R 1 in the general formula (1).
  • the amount of the metal chelate compound is preferably 0.0001 to 10 parts by mass, more preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of silane compounds (in terms of complete hydrolysis condensate). If the amount is less than 0.0001 part by mass, the coating property of the coating film may be inferior, and if it exceeds 10 parts by mass, the polymer growth cannot be controlled and gelation may occur.
  • 0.5 to 20 mol of water is preferably used per 1 mol of the total amount of silane compounds, and 1 to 10 mol of water is used. Is particularly preferred.
  • the hydrolysis reaction does not proceed sufficiently, which may cause problems in coating properties and storage stability. If the amount exceeds 20 mol, the hydrolysis and condensation reaction may occur. Polymer precipitation or gelation may occur. Moreover, it is preferable that water is added intermittently or continuously.
  • Acidic compounds examples include organic acids and inorganic acids, with organic acids being preferred.
  • 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, shikimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linolenic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzenesulfone Acid, monochloroacetic acid, dichloroacetic acid, t
  • inorganic acids examples include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
  • organic acids are preferable in that there is little risk of polymer precipitation or gelation during the reaction of hydrolysis condensation (hydrolysis and subsequent condensation), and among these, compounds having a carboxyl group are more preferable.
  • compounds having a carboxyl group acetic acid, oxalic acid, maleic acid, formic acid, malonic acid, phthalic acid, fumaric acid, itaconic acid, succinic acid, mesaconic acid, citraconic acid, malic acid, malonic acid, glutaric acid, maleic anhydride
  • Organic acids such as acid hydrolysates are particularly preferred. These acidic compounds can be used alone or in combination of two or more.
  • the amount of the acidic compound is preferably 0.0001 to 10 parts by mass, more preferably 0.001 to 5 parts by mass with respect to 100 parts by mass (in terms of complete hydrolysis condensate) of the silane compound.
  • the amount is less than 0.0001 parts by mass, the coating property of the coating film may be inferior, and when it exceeds 10 parts by mass, the hydrolysis and condensation reaction may proceed rapidly to cause gelation.
  • hydrolyzing and condensing a hydrolyzable silane compound in the presence of an acidic compound 0.5 to 20 mol of water is preferably used per 1 mol of the total amount of silane compounds, and 1 to 10 mol of water is preferably used. Particularly preferred.
  • the hydrolysis reaction does not proceed sufficiently, which may cause problems in coating properties and storage stability. If the amount exceeds 20 mol, precipitation of the polymer during the hydrolysis condensation reaction may occur. And gelation may occur. Moreover, it is preferable that water is added intermittently or continuously.
  • (D-3) Basic compounds
  • Examples of basic compounds that can be used as catalysts include methanolamine, ethanolamine, propanolamine, butanolamine, N-methylmethanolamine, N-ethylmethanolamine, and N-propylmethanolamine.
  • N-butylmethanolamine N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine N, N-dimethylmethanolamine, N, N-diethylmethanolamine, N, N-dipropylmethanolamine, N N-dibutylmethanolamine, N-methyldimethanolamine, N-ethyldimethanolamine, N-propyldimethanolamine, N-butyldimethanolamine, N- (aminomethyl) methanolamine, N- (aminomethyl) Ethanor Ruamine, N- (aminomethyl) propanolamine, N- (aminomethyl) butanolamine, methoxymethylamine, methoxyethylamine, methoxypropylamine, methoxybutylamine, N, N-dimethylamine, N, N-diethylamine, N, N -Dipropylamine, N, N-dibutylamine, trimethylamine, triethyl
  • metal oxide particles having a high refractive index are used.
  • Such fine particles are not particularly limited as long as the refractive index of light at a wavelength of 400 nm at 25 ° C. is preferably 1.55 or more, more preferably 1.60 or more, and particularly preferably 1.70 or more.
  • metal oxide particles such as zirconium oxide, titanium oxide, zinc oxide, tantalum oxide, indium oxide, hafnium oxide, tin oxide, niobium oxide, and composites thereof.
  • fine particles of zirconium oxide (ZrO 2 ) are preferable.
  • the titanium oxide is not particularly limited as long as it has a TiO 2 structure, and examples thereof include an anatase type, a rutile type, and a brookite type. These metal oxide particles can be used alone or in combination of two or more.
  • the number average primary particle diameter of the metal oxide particles (B) is preferably 1 to 100 nm, more preferably 3 to 70 nm, and particularly preferably 5 to 50 nm. When the number average primary particle diameter is within the above range, a cured product having excellent transparency can be obtained.
  • the metal oxide particles as the component (B) may be in a powder form or a solvent-dispersed sol before mixing with the component (A) and the component (C).
  • the solvent for example, an organic solvent is used.
  • organic solvent examples include 2-butanol, methanol, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, N-methyl-2-pyrrolidone, propylene glycol monomethyl ether, and the like.
  • Component (B) is blended in an amount of 50 to 2,000 parts by weight, preferably 100 to 1,500 parts by weight, more preferably 150 to 1,000 parts by weight, per 100 parts by weight of component (A). . If the amount exceeds 1,000 parts by mass, sufficient crack resistance may not be obtained. If the amount is less than 100 parts by mass, the refractive index of the cured film (cured body of the composition) decreases, and light emission occurs. There is a possibility that the luminous efficiency of the device may be lowered.
  • (B) component is solvent dispersion
  • the quantity of the organic solvent as a solvent of (B) component shall comprise a part of compounding quantity of the organic solvent which is (C) component.
  • Component (C); Organic solvent In the present invention, the storage stability of the composition can be improved and an appropriate viscosity can be imparted by blending an organic solvent.
  • organic solvent include ether organic solvents, ester organic solvents, ketone organic solvents, hydrocarbon organic solvents, alcohol organic solvents, and the like.
  • the organic solvent it is preferable to use an organic solvent having a boiling point in the range of 50 to 250 ° C. under atmospheric pressure (1,013 hPa) and capable of uniformly dispersing each component.
  • organic solvents examples include aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents, monoalcohol solvents, polyhydric alcohol solvents, ketone solvents, ether solvents, ester solvents, nitrogen-containing solvents. And sulfur-containing solvents. These organic solvents are used alone or in combination of two or more.
  • organic solvents monoalcohol solvents, polyhydric alcohol solvents, and ketone solvents are preferable from the viewpoint of further improving the storage stability of the composition.
  • preferable compounds of these solvents include propylene glycol monomethyl ether, ethyl lactate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl amyl ketone, methanol, ethanol, 2-butanol and the like. These preferable compounds are used alone or in combination of two or more.
  • the type of the organic solvent is preferably selected in consideration of the coating method of the composition.
  • the organic solvent is a glycol ether such as ethylene glycol monoethyl ether or propylene glycol monomethyl ether.
  • Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate; esters such as ethyl lactate and ethyl 2-hydroxypropionate; diethylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl Diethylene glycols such as ether; methyl ethyl ketone, methyl isobutyl ketone, 2-heptanone, cycl It is preferred to use such ⁇ - butyrolactone; hexanone, ketones such as methyl amyl ketone.
  • Particularly preferred organic solvents are ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, ethyl lactate, methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone and the like.
  • the amount of component (C) is preferably 50 to 20,000 parts by weight, more preferably 100 to 1,000 parts by weight based on 100 parts by weight of the total amount of the components of the composition excluding the organic solvent. Part. Within the above preferred range, the storage stability of the composition can be improved, an appropriate viscosity can be imparted, and a high refractive index cured film having a uniform thickness can be easily formed. .
  • the method for adding the component (C) is not particularly limited.
  • the component (A) may be added when the component (A) is produced, or may be added when preparing the dispersion containing the component (B). Alternatively, it may be added when the component (A) and the component (B) are mixed.
  • the curable resin composition of the present invention can use various dispersants in order to improve the dispersibility of the metal oxide particles.
  • the dispersant for example, an aluminum compound can be used.
  • the aluminum compound include aluminum alkoxide and aluminum ⁇ -diketonate complex.
  • alkoxide compounds such as triethoxyaluminum, tri (n-propoxy) aluminum, tri (i-propoxy) aluminum, tri (n-butoxy) aluminum, tri (sec-butoxy) aluminum, aluminum tris (methylacetate) Acetate), aluminum tris (ethyl acetoacetate), tris (acetoacetonato) aluminum, aluminum monoacetylacetonatobis (methyl acetate), aluminum monoacetylacetonatobis (ethyl acetate) and the like ⁇ -diketonate complexes.
  • alkoxide compounds such as triethoxyaluminum, tri (n-propoxy) aluminum, tri (i-propoxy) aluminum, tri (n-butoxy) aluminum, tri (sec-butoxy) aluminum, aluminum tris (methylacetate) Acetate), aluminum tris (ethyl acetoacetate), tris (acetoacetonato) aluminum, aluminum monoacetylacetonatobis (methyl acetate), aluminum monoace
  • Aluminum compounds Commercial products of aluminum compounds include AIPD, PADM, AMD, ASBD, aluminum ethoxide, ALCH, ALCH-50F, ALCH-75, ALCH-TR, ALCH-TR-20, aluminum chelate M, aluminum chelate D, aluminum chelate A (W), surface treatment agent OL-1000, Algomer, Algomer 800AF, Algomer 1000SF (manufactured by Kawaken Fine Chemical Co., Ltd.) and the like can be used.
  • a nonionic dispersant can also be used as the dispersant. Dispersibility can be improved by using a nonionic dispersant.
  • the nonionic dispersant used in the present invention is preferably a phosphate ester nonionic dispersant having a polyoxyethylene alkyl structure.
  • the blending amount of the dispersant is not particularly limited, but when the dispersant is included, it is, for example, 0.1 to 5% by mass with respect to 100% by mass of the total component of the composition excluding the organic solvent.
  • the curable resin composition of the present invention can further contain a dispersion aid in order to enhance dispersibility.
  • a dispersion aid one or more selected from acetylacetone, N, N-dimethylacetoacetamide and the like can be preferably used.
  • the blending amount of the dispersion aid is not particularly limited, but when the dispersion aid is included, it is, for example, 0.1 to 5% by mass with respect to 100% by mass of the total component of the composition excluding the organic solvent.
  • a surfactant When the curable resin composition of the present invention is applied to a substrate or the like by spin coating, a surfactant is preferably blended from the viewpoint of obtaining a coating film having a uniform thickness.
  • the surfactant used in the present invention include a silicone-based surfactant and a fluorine-based surfactant. Of these, silicone surfactants are preferred.
  • silicone surfactants include, for example, SH28PA (Toray Dow Corning, dimethylpolysiloxane polyoxyalkylene copolymer), Paintad 19, 54 (Toray Dow Corning, dimethylpolysiloxane polyoxyalkylene copolymer).
  • FM0411 silicaplane, manufactured by Chisso
  • SF8428 manufactured by Toray Dow Corning, dimethylpolysiloxane polyoxyalkylene copolymer (containing side chain OH)
  • BYKUV3510 manufactured by Big Chemie Japan, dimethylpolysiloxane) -Polyoxyalkylene copolymer
  • DC57 manufactured by Toray Dow Corning Silicone, dimethylpolysiloxane-polyoxyalkylene copolymer
  • DC190 manufactured by Toray Dow Corning Silicone, dimethylpolysiloxane
  • Particularly preferred examples include Silaplane FM-7711, FM-7721, FM-7725, FM-0411, FM-0421, FM-0425, FM0711, FM0721, FM-0725, VPS-1001, and the like.
  • TegoRad2300, 2200N made by Tego Chemie
  • fluorosurfactant examples include, for example, MegaFuck F-114, F410, F411, F450, F493, F494, F443, F444, F445, F446, F470, F471, F472SF, F474, F475, R30, F477, F478, F479, F480SF, F482, F483, F484, F486, F487, F172D, F178K, F178RM, ESM-1, MCF350SF, BL20, R08, R61, R90 (manufactured by DIC) can be mentioned.
  • the blending ratio of the component (F) is preferably 0 to 10% by mass, more preferably 0.1 to 5% by mass, and particularly preferably 0.5% with respect to 100% by mass of the total amount of the components excluding the organic solvent. To 3% by mass. If the amount exceeds 10% by mass, the refractive index of the cured product of the composition may be lowered.
  • the curable resin composition of the present invention can also contain a dehydrating agent.
  • a dehydrating agent By adding a dehydrating agent, the radiation curing reaction of the composition can be promoted, and the storage stability of the composition can be further improved.
  • the dehydrating agent used in the present invention is a compound that converts water into a substance other than water by a chemical reaction, or a substance that does not affect radiation curability and storage stability by physical adsorption or inclusion. Is defined as a compound.
  • the dehydrating agent effectively absorbs water entering from the outside, thereby improving the storage stability of the composition.
  • the condensation reaction which is a radiation curing reaction
  • the generated water is used as the dehydrating agent. It is considered that the radiation curable property of the composition is improved by sequentially absorbing.
  • the curable resin composition of the present invention can also contain an acid generator.
  • the acid generator is defined as a compound capable of generating an acid by light irradiation or heating.
  • light irradiation means irradiation with ionizing radiation such as infrared rays, visible rays, ultraviolet rays, and X-rays, electron beams, ⁇ rays, ⁇ rays, and ⁇ rays.
  • a photo-acid generator which can generate
  • M is a metal or metalloid constituting the central atom of the halide complex [MX m + n ], for example, B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, or Co.
  • Z is, for example, a halogen atom or an aryl group such as F, Cl, Br, etc.
  • m is the net charge of the halide complex ion
  • n is the valence of M.
  • Q is a monovalent or divalent organic group
  • R 6 is a monovalent organic group having 1 to 12 carbon atoms
  • the subscript s is 0 or 1
  • the subscript t is 1 or 2. is there. ]
  • an onium salt that is a compound of the first group is a compound that can release an acidic active substance by receiving light.
  • a more effective onium salt is an aromatic onium salt, and particularly preferably a diaryliodonium salt represented by the following general formula (5).
  • R 7 -Ar 1 -I + -Ar 2 -R 8 [Y ⁇ ] (5)
  • R 7 and R 8 are each a monovalent organic group and may be the same or different, and at least one of R 7 and R 8 represents an alkyl group having 4 or more carbon atoms.
  • Each of Ar 1 and Ar 2 is an aromatic group, which may be the same or different, and Y 2 ⁇ is a monovalent anion, and is a group 3 or group 5 fluoride anion of the periodic table. Or, it is an anion selected from ClO 4 ⁇ and CF 3 —SO 3 — . ]
  • Examples of the sulfonic acid derivative represented by the general formula (4) as the second group of compounds include disulfones, disulfonyldiazomethanes, disulfonylmethanes, sulfonylbenzoylmethanes, imidosulfonates, benzoin. Examples include sulfonates, sulfonates of 1-oxy-2-hydroxy-3-propyl alcohol, pyrogallol trisulfonates, and benzyl sulfonates. Of the sulfonic acid derivatives represented by the general formula (4), imide sulfonates are more preferable, and among imide sulfonates, trifluoromethyl sulfonate derivatives are more preferable.
  • the amount (content ratio) of the photoacid generator will be described.
  • the addition amount of the photoacid generator is not particularly limited, but it is preferable that the total amount of the solid content of the curable resin composition is 100 parts by mass, usually within 15 parts by mass. When the added amount exceeds 15 parts by mass, the weather resistance and heat resistance of the resulting cured product tend to be lowered.
  • the curable resin composition of this invention can contain various additives other than the above within the range which does not impair the effect of this invention.
  • additives include curable compounds other than the above components, antioxidants, ultraviolet absorbers, and the like.
  • the curable resin composition of the present invention is prepared by mixing the above components (A) to (C) and other optional components to be blended as necessary.
  • the component (A) a specific siloxane polymer, the component (B) metal oxide particles, and other components optionally added are mixed in a predetermined ratio in the organic solvent (C), thereby curable resin.
  • a composition can be prepared.
  • the refractive index of the cured film that is a cured product of the composition of the present invention is preferably 1.6 or more. When the refractive index is 1.6 or more, the light emission efficiency of the light emitting device is increased.
  • the thickness of the cured film is not particularly limited, but can be appropriately determined within a range of 50 nm to 100 ⁇ m, for example, depending on the type of the light emitting element.
  • the curable resin composition of the present invention is not particularly limited, for example, light emitting diodes, semiconductor lasers, photodiodes, phototransistors, electroluminescent elements and other light emitting elements, CCDs, CMOS image sensors, and other optical members, It can be used for an antireflection film of a solar cell, and is preferably used for a light emitting element such as a light emitting diode, a semiconductor laser, a photodiode, a phototransistor, and an electroluminescence element.
  • the light emitting device of the present invention is not particularly limited, and examples thereof include a light emitting diode, a semiconductor laser, a photodiode, a phototransistor, an electroluminescence element, a CCD, a C-MOS, and a solar cell.
  • the light-emitting device of the present invention is manufactured by coating the surface of the light-emitting element with the curable resin composition of the present invention and curing it to form a cured film, and further sealing with a sealing material as necessary. Can do.
  • the method for coating (coating) the curable resin composition of the present invention is not particularly limited, and is appropriately selected from spin coating, dip coating, potting, inkjet, etc.
  • the light emitting device shown in FIG. 1 includes a structure in which a cured film 2 made of the curable resin composition of the present invention is formed on the surface of a light emitting element 1 and sealed with a sealing material 5.
  • reference numerals 3a and 3b denote electrode portions, 4a and 4b denote thin metal wires, and 6 denotes an insulating substrate.
  • the light-emitting device is a light-emitting diode
  • a light-emitting diode element manufactured using a compound such as GaAs, GaAlAs, AlGaInP, GaP, GaAsP, ZnSe, ZnS, GaN, or InGaN can be used.
  • the light emission color of the light emitting diode is not particularly limited, and examples thereof include red, green, blue, yellow, orange, yellow green, and white.
  • the total number of silicon atoms is the sum of ST1 to ST3 and SQ1 to SQ4 (ST1 + ST2 + ST3 + SQ1 + SQ2 + SQ3 + SQ4).
  • ⁇ Y (2 ⁇ ST1 + 1 ⁇ ST2 + 0 ⁇ ST3 + 3 ⁇ SQ1 + 2 ⁇ SQ2 + 3 ⁇ SQ3 + 0 ⁇ SQ4) / (ST1 + ST2 + ST3 + SQ1 + SQ2 + SQ3 + SQ4) ⁇ .
  • T1 A silicon atom in which one carbon atom and three oxygen atoms are bonded (wherein, one of oxygen atoms is contained in a siloxane bond and two in a silanol group)
  • T2 A silicon atom in which one carbon atom and three oxygen atoms are bonded (wherein two of the oxygen atoms are contained in a siloxane bond and one in a silanol group)
  • T3 A silicon atom in which one carbon atom and three oxygen atoms are bonded (wherein oxygen atoms are all included in the siloxane bond).
  • Q1 A silicon atom to which four oxygen atoms are bonded (here, one of oxygen atoms is contained in a siloxane bond and three in a silanol group)
  • Q2 A silicon atom to which four oxygen atoms are bonded (wherein two of oxygen atoms are contained in a siloxane bond and two in a silanol group, respectively).
  • Q3 A silicon atom to which four oxygen atoms are bonded (herein, three of the oxygen atoms are contained in a siloxane bond and one in a silanol group)
  • Q4 A silicon atom bonded with four oxygen atoms (a silicon atom bonded with four oxygen atoms (wherein three oxygen atoms are contained in a siloxane bond and one in a silanol group)
  • composition 1 As component (B), 21.0 g of zirconium oxide (primary average particle size: 15 nm), 29.7 g of “A-1” (solid content: 8.9 g), and propylene glycol so that the total weight of the organic solvent is 70 g. Monomethyl ether is put in a container, and 350 g of zirconia beads having a particle size of 0.1 mm (made by Nikkato Co., Ltd.) are added thereto, and the mixture is stirred at 1500 rpm for 10 hours by a bead mill to disperse zirconium oxide fine particles (component (B)) I let you.
  • component (B) 21.0 g of zirconium oxide (primary average particle size: 15 nm), 29.7 g of “A-1” (solid content: 8.9 g), and propylene glycol so that the total weight of the organic solvent is 70 g.
  • Monomethyl ether is put in a container, and 350 g of zirconia beads having a particle
  • composition “J-1” 0.10 g of dimethylpolysiloxane-polyoxyalkylene copolymer was added to the obtained dispersion of fine particles of zirconium oxide to obtain a composition “J-1”. Further, the compositions “J-2”, “J-4”, “J-5”, “J-6” were the same as the composition “J-1” except that the components shown in Table 3 were used. Was prepared.
  • composition Preparation 2 As component (B), 15.9 g of zirconium oxide fine particles (number average primary particle size: 15 nm), 1.9 g of PLAADD ED-151 (compound name: polyoxyethylene alkyl phosphate ester), tri (sec-butoxy) aluminum 2.2 g, 0.9 g of acetylacetone, 2.3 g of 2-butanol, and 54.3 g of methyl ethyl ketone were added to a container, 300 g of zirconia beads having a particle diameter of 0.1 mm (manufactured by Nikkato Co., Ltd.) were added thereto, and 1500 rpm, The mixture was stirred for 10 hours to disperse the fine particles of zirconium oxide (component (B)).
  • compositions “J-1” to “J-6” were evaluated as follows. ⁇ Evaluation of properties of composition> (1) Dispersed particle size About the fine particles in the obtained composition, the volume average particle size at 25 ° C. was measured by a dynamic light scattering particle size distribution measuring apparatus manufactured by Horiba, Ltd. A sample having a volume average particle size of less than 50 nm was indicated by “ ⁇ ”, a sample having a volume average particle size of 50 nm or more and less than 100 nm was indicated by “ ⁇ ”, and a particle having a volume average particle size of 100 nm or more was indicated by “X”. The results are shown in Table 3.
  • the composition is dispensed on a 4-inch diameter fused quartz or silicon substrate, spin-coated to a thickness of about 1 ⁇ m, heated at 120 ° C. for 1 minute, and 200 ° C. for 60 minutes to form a cured film ( Film thickness: 1 ⁇ m) was produced.
  • the transmittance (%) at a wavelength of 400 nm of the cured film was measured using a spectrophotometer manufactured by JASCO Corporation. The case where the transmittance was 90% or more was “ ⁇ ”, and the case where the transmittance was less than 90% was “ ⁇ ”.
  • (5) Refractive index The refractive index in 23 degreeC and wavelength 633nm was measured using the prism coupler by a metricon company. The case where the refractive index was 1.6 or more was “ ⁇ ”, and the case where the refractive index was less than 1.6 was “x”.
  • the cured product of the composition of the present invention has excellent transparency, high refractive index, high heat resistance, and high light resistance, and emitted light from a light emitting device including a light emitting element such as an LED element. It turns out that the effective use of can be expected.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Led Device Packages (AREA)

Abstract

L'invention concerne une composition de résine durcissable conçue pour recouvrir un élément électroluminescent, qui a un indice de réfraction élevé, une excellente transparence, une excellente résistance à la chaleur et des caractéristiques similaires, et qui permet d'obtenir un dispositif électroluminescent qui présente une excellente efficacité lumineuse. L'invention concerne spécifiquement une composition de résine durcissable qui contient (A) un polymère de siloxane qui est obtenu à partir d'un composé de silane contenant un composé représenté par la formule générale (1) : (R1)pSi(X)4-p (dans laquelle R1 représente un groupe organique non hydrolysable contenant de 1 à 12 atomes de carbone, X représente un groupe hydrolysable, et p représente un nombre entier allant de 0 à 3), (B) des particules d'oxyde de métal et (c) un solvant organique. Le composant (A) contient un groupe silanol, et le nombre de groupes hydroxyle contenus dans le groupe silanol est en proportion de 15 à 300 % par rapport au nombre d'atome de silicium contenus dans le polymère de siloxane, et la quantité du composant (B) contenu dans la composition va de 50 à 1 000 parties en masse par rapport à 100 parties en masse du composant (A). La composition de résine durcissable est un matériau permettant d'obtenir un film durci (2) qui recouvre un élément électroluminescent (1).
PCT/JP2011/057793 2010-03-31 2011-03-29 Composition de résine durcissable et dispositif électroluminescent Ceased WO2011125646A1 (fr)

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