WO2014192839A1 - 光半導体封止用硬化性組成物 - Google Patents
光半導体封止用硬化性組成物 Download PDFInfo
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- WO2014192839A1 WO2014192839A1 PCT/JP2014/064201 JP2014064201W WO2014192839A1 WO 2014192839 A1 WO2014192839 A1 WO 2014192839A1 JP 2014064201 W JP2014064201 W JP 2014064201W WO 2014192839 A1 WO2014192839 A1 WO 2014192839A1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical class FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005118 spray pyrolysis Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- TZLPVFCPHOVVII-UHFFFAOYSA-N tetrakis(4-methylphenyl)phosphanium tetraphenylphosphanium Chemical class C1(=CC=C(C=C1)[P+](C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C.C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 TZLPVFCPHOVVII-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OXTXYKOWIHKUFN-UHFFFAOYSA-N tetratert-butyl 5-benzoylbenzene-1,2,3,4-tetracarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC(C(=O)C=2C=CC=CC=2)=C1C(=O)OOC(C)(C)C OXTXYKOWIHKUFN-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
- C08G59/60—Amines together with other curing agents with amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Definitions
- the present invention relates to a curable composition used for sealing an optical semiconductor element such as an LED element or an organic EL element, a cured product thereof, and an optical semiconductor and an optical semiconductor device using the same.
- Optical semiconductor elements such as LED elements and organic EL elements are characterized in that light emission with high luminance can be obtained with small electric power, and application development to various uses such as lighting devices and display devices has been attempted.
- Patent Document 1 discloses a sealing agent for an organic electroluminescence device containing 20 to 80 parts by weight of an epoxy compound having an aliphatic cyclic skeleton and 80 to 20 parts by weight of an epoxy compound having an aromatic ring. Yes. However, there is no description regarding countermeasures against outgas derived from the resin composition.
- Patent Document 2 (A) an epoxy resin having at least two or more glycidyl groups in one molecule and a molecular weight of 200 to 7000, and (B) having at least one or more glycidyl groups in one molecule.
- An epoxy resin having a molecular weight of 20000 to 100,000, (C) a latent photoacid catalyst that is activated by energy ray irradiation to generate an acid, and (D) a silane coupling agent containing a glycidyl group in the molecule Comprising 30 to 150 parts by weight of the component (B) with respect to 100 parts by weight of the component (A) and 100 parts by weight of the total of the components (A) and (B).
- a curable resin composition for sealing an organic EL element containing 0.1 to 10 parts by weight of the component (C) and 0.1 to 10 parts by weight of the component (D) is disclosed.
- the outgas suppression level is not sufficient.
- Patent Document 3 discloses a resin composition containing (A) an epoxy compound, (B) a novolac resin, (C) a cationic photopolymerization initiator, and (D) a filler as an adhesive for an element package such as an organic EL. It is disclosed. However, there is no description about measures against outgas.
- Patent Document 4 discloses that a compound (A) having two or more reactive functional groups (a) in one molecule, one reactive functional group (b) in one molecule, and a molecular weight of 50 ⁇
- a low moisture-permeable resin composition for electronic devices requiring low moisture permeability comprising a compound (B) of 1000 and a polymerization initiator (C) is disclosed.
- a compound (B) of 1000 and a polymerization initiator (C) is disclosed.
- the curability of the resin composition and measures against outgas.
- the curable resin of Patent Document 5 contains an epoxy resin having an oxirane ring at the terminal, and an aliphatic cyclic epoxy resin and / or a compound having an octacene ring, a large amount of outgas is generated. Moreover, since the epoxy resin composition of patent document 4 and patent document 6 has a biphenyl structure, outgas, such as acrolein, is generated with a catalyst.
- conductive fine particles are used for connecting fine electrodes in optical semiconductor elements such as LED elements and organic EL elements.
- conductive fine particles as disclosed in Patent Document 5, conductive fine particles obtained by coating a metal on the surface of resin fine particles are known.
- the conductive fine particles described above have a problem that the cost of raw materials is high because many metal materials are used because the surface of resin fine particles is coated with metal. Moreover, since it is necessary to manufacture by special methods, such as an electroplating method and an alternate adsorption method, it was necessary to use a special apparatus or to pass through many processes, and also had the problem that manufacturing cost was high.
- the metal-coated resin particles are colored because the entire surface is coated with metal, and in addition, in order to impart conductivity to the cured resin, it is necessary to bring the conductive fine particles into contact with each other in the cured resin. Because there is, mix in large quantities. For this reason, it has been difficult to obtain a cured product having both transparency and conductivity at low cost.
- An object of the present invention is to contribute to stabilizing the performance and extending the life of an optical semiconductor element and an optical semiconductor device by suppressing the intrusion or generation of moisture and gas that deteriorate the optical semiconductor element, and is highly transparent.
- An object of the present invention is to provide a curable composition for encapsulating an optical semiconductor element having good properties and excellent productivity, and a cured product thereof.
- the objective of this invention provides the curable composition for optical semiconductor element sealing which is excellent in electroconductivity (especially electroconductivity to thickness direction), and its hardened
- Another object of the present invention is to provide an optical semiconductor and an optical semiconductor device that have stable performance and a long lifetime.
- the present inventors have found that a cured product of a curable composition for optical semiconductors containing a curable compound having a specific functional group and a curing catalyst deteriorates an optical semiconductor element.
- the present inventors have found that the invasion or generation of excessive moisture and gas is suppressed.
- a curable composition for sealing an optical semiconductor comprising the following components (A), (B), and (C).
- Component (A) Compound component having one or more functional groups selected from the group consisting of epoxy group, oxetanyl group, vinyl ether group and (meth) acryloyl group
- B) alicyclic epoxy compound component
- C) aromatic ring Curing catalyst component (D) which has an cation component and an anion component whose central element is boron or phosphorus and generates an acid by light or heat: a particulate material and a fibrous material covering the particulate material
- the component (A) has an aromatic ring, and two or more selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group
- the component (A) has an aromatic ring, has a molecular weight of 100 to 1,000, and one function selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group.
- the component (A) is a compound having one or more functional groups selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group, and having an aromatic ring.
- X represents a single bond or a linking group
- the content of component (B) is 30 to 95% by weight relative to the total amount of curable composition (100% by weight), and the content of component (C) is the total amount of curable composition ( The curable composition for sealing an optical semiconductor according to any one of the above [1] to [10], which is 0.01 to 8% by weight relative to 100% by weight).
- the curable composition of the present invention Since the curable composition of the present invention has the above-described configuration, it becomes possible to suppress the intrusion or generation of moisture or gas that deteriorates the optical semiconductor element, and stabilizes the performance of the optical semiconductor element or the optical semiconductor device. Can be achieved. Moreover, the curable composition for optical semiconductor element sealing which has high transparency and outstanding productivity and its hardened
- the organic EL device of the present invention sealed with the curable composition or the sealing sheet or film made of the curable composition is excellent in light extraction efficiency (that is, excellent in light emission efficiency), excellent. Have high brightness.
- conductive fiber-coated particles when conductive fiber-coated particles are used, it is possible to obtain a curable composition for sealing an optical semiconductor element that is excellent in conductivity (particularly, conductivity in the thickness direction) and a cured product thereof.
- the conductive fiber-coated particles of the present invention particularly, the conductive fiber-coated particles having flexibility, when the curable composition containing the particles is formed into a shape having fine irregularities, the conductive fiber-coated particles have the irregular structure. Therefore, it is possible to prevent the occurrence of a portion having poor conductivity and to obtain a cured product having excellent conductive performance.
- FIG. 2 is an example of a scanning electron microscope image (SEM image) of the conductive fiber-coated particles (conductive fiber-coated particles of the present invention) obtained in Production Example 1.
- SEM image scanning electron microscope image
- the curable composition for optical semiconductor sealing of this invention is characterized by including the following component (A), (B), and (C).
- the curable composition for optical semiconductor sealing of this invention is characterized by including the following component (A), (B), (C) and (D).
- Component (A) may be a compound having one or more functional groups selected from the group consisting of epoxy groups, oxetanyl groups, vinyl ether groups, and (meth) acryloyl groups (excluding compounds corresponding to component (B)).
- Component (A) is a compound having one or more functional groups selected from the group consisting of epoxy groups, oxetanyl groups, vinyl ether groups, and (meth) acryloyl groups, and having an aromatic ring.
- the curable compound of the present invention is a compound that is cured by light or heat, and is not particularly limited as long as it includes the component (A) and the component (B). In the range which does not impair the effect of this application, curable compounds other than the said component (A) and component (B) can also be included.
- the component (A) is not particularly limited as long as it is a compound having one or more functional groups selected from the group consisting of an epoxy group, an oxetane group, a vinyl ether group, and a (meth) acryloyl group.
- the number of functional groups that the compound of component (A) has is not particularly limited, but as described in WO2012 / 020688 (Patent Document 4), generally from an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group. It is preferable to use a compound having two or more functional groups selected from the group consisting of the following groups (hereinafter sometimes referred to as “compound (A1)”).
- the molecular weight is 100 to 1000, and one functional group selected from the group consisting of epoxy groups, oxetanyl groups, vinyl ether groups, and (meth) acryloyl groups is included. It is more preferable to blend a compound (hereinafter sometimes referred to as “compound (A2)”) together with the compound (A1).
- compound (A2) a compound that is more preferable to blend a compound (hereinafter sometimes referred to as “compound (A2)”) together with the compound (A1).
- Component (A) is not particularly limited, but preferably has a cyclic skeleton such as an alicyclic cyclic skeleton or an aromatic cyclic skeleton. Each cyclic skeleton may be the same or different. When one molecule of component (A) has two or more cyclic skeletons, the plurality of cyclic skeletons may be the same or different.
- cyclic skeleton examples include monocyclic or condensed polycyclic aromatic rings such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, and fluorene ring; cyclopentane ring, cyclohexane ring, decahydronaphthalene ring, norbornane Examples thereof include monocyclic or polycyclic aliphatic rings such as a ring and an adamantane ring.
- the number of polycyclic cyclic skeletons in which n rings are condensed is n.
- the number of cyclic skeletons in one molecule of component (A) is, for example, 1 to 30, preferably 1 to 10, more preferably 1 to 6, and further preferably 1 to 5.
- the content of the compound (A) is based on the total amount (100% by weight) of the curable compound of the present invention from the viewpoint of low moisture permeability, high gas barrier property, applicability of the curable composition, hardness of the cured product, and the like. 5 to 80% by weight is preferable, 10 to 70% by weight is more preferable, and 20 to 60% by weight is further preferable. In particular, from the viewpoint of outgas suppression, it is preferably 10 to 70% by weight, more preferably 20 to 60% by weight.
- the compound (A1) has two or more functional groups selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group (above, cationic polymerizable functional group), and a (meth) acryloyl group (radical polymerizable functional group).
- the functional group is preferably an epoxy group (particularly preferably a glycidyl group).
- the number of functional groups in one molecule of the compound (A1) is, for example, 2 to 30, preferably 2 to 10, more preferably 2 to 6, and further preferably 2 to 3.
- the plurality of functional groups may be the same or different.
- the molecular weight of the compound (A1) is not particularly limited, but is preferably 100 to 10,000, more preferably 150 to 5,000, and still more preferably 200 to 1,000.
- a compound (A1) can be used individually by 1 type or in combination of 2 or more types.
- Examples of the compound (A1) include a compound (A1-1) having two or more cationically polymerizable functional groups and an aromatic ring in one molecule; two or more radically polymerizable functional groups in one molecule. And a compound (A1-2) having an aromatic ring.
- Examples of the compound (A1-1) having two or more cationically polymerizable functional groups and an aromatic ring in one molecule include biphenol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, and bisphenol.
- Compounds having a benzene ring and two epoxy groups such as S diglycidyl ether and tetramethylbiphenol diglycidyl ether; naphthalenediol diglycidyl ether, bisphenol fluorenediglycidyl ether, biscresol fluorenediglycidyl ether, bisphenoxyethanol fluorenediglycidyl ether, etc.
- a compound having a condensed ring and two epoxy groups a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a biphenyl skeleton-containing novolat A compound having a benzene ring and / or a condensed ring and two or more epoxy groups, such as polyphenylglycidyl ethers having a repeating unit such as an epoxy resin and a novolak epoxy resin containing a naphthalene skeleton; bisphenol F bis (3-ethyl) Compounds having an aromatic ring and two oxetanyl groups such as oxetane-3-ylmethyl) ether; biphenol divinyl ether, bisphenol A divinyl ether, bisphenol F divinyl ether, bisphenol F bis (2-vinyloxyethyl) ether, bisphenol S di Compounds having a benzene ring and two vinyl ether groups, such as vinyl ether and tetramethylbiphenol
- Examples of the C 1-9 alkyl substituent in the C 1-9 alkyl substituent include methyl, ethyl, propyl, and t-butyl groups.
- Examples of the halogen in the halide include F, Cl, Br and the like.
- biphenol di (meth) acrylate bisphenol A di (meth) acrylate, bisphenol F di (meta) ) Acrylate, bisphenol S di (meth) acrylate, tetramethylbiphenol di (meth) acrylate and other benzene rings and two (meth) acryloyl group compounds
- naphthalenediol di (meth) acrylate, biphenol full orange (meth) acrylate , Biscresol full orange (meth) acrylate, bisphenoxyethanol full orange (meth) acrylate, and other condensed rings and two (meth) acryloyl groups and halides thereof, or C 1-9 alkyl substituents thereof Etc.
- Examples of the C 1-9 alkyl substituent in the C 1-9 alkyl substituent include methyl, ethyl, propyl, and t-butyl groups.
- Examples of the halogen in the halide include F, Cl, Br and the like.
- Z 1 represents a group obtained by removing m OH groups from an m-valent polyvalent hydroxy compound (Z 1 (OH) m), and R 1 has a glycidyl group and a substituent. Or a good oxetanyl group, vinyl group, or (meth) acryloyl group.
- m is an integer of 2 or more.
- Z 1 is preferably a group having a cyclic skeleton. Examples of the cyclic skeleton include those exemplified above.
- m-valent polyvalent hydroxy compound Z 1 (OH) m compounds having two benzene rings such as biphenol, bisphenol A, bisphenol F, bisphenol S and the like, halides thereof, or C 1-9 alkyls thereof
- Substituted compounds compounds having a condensed ring such as naphthalenediol, bisphenol fluorene, biscresol fluorene, bisphenoxyethanol fluorene, and halides thereof, or C 1-9 alkyl substituents thereof; hydrogenated bisphenol A, hydrogenated bisphenol F , Compounds having three or more aromatic rings such as benzene rings such as hydrogenated bisphenol S and dicyclohexyl, and halides thereof, or C 1-9 alkyl substituted products thereof.
- Examples of the C 1-9 alkyl substituent in the C 1-9 alkyl substituent include methyl, ethyl, propyl, and t-butyl groups.
- Examples of the halogen in the halide include F, Cl, Br and the like.
- Compound (A1) is preferably a compound having two each of an epoxy group, an oxetane group, a vinyl ether group and a (meth) acryloyl group, and a benzene ring or a cyclohexane ring.
- the compound (A1) include diglycidyl ether having 2 to 4 benzene rings such as bisphenol F diglycidyl ether, tetramethylbiphenol diglycidyl ether, or bisphenoxyethanol fluorenediglycidyl ether; bisphenol F bis ( Dioxetanyl ether having 2 to 4 benzene rings such as 3-ethyloxetane-3-ylmethyl) ether; divinyl ether having 2 to 4 benzene rings such as bisphenol F divinyl ether; or bisphenol F di (meth) acrylate (Meth) acrylate having 2 to 4 benzene rings can be preferably used.
- the compound (A1) a compound having two glycidyl groups and two benzene rings is particularly preferable.
- the compound (A1) is a compound (A1 ′) having an aromatic ring and having two or more functional groups selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group. Preferably there is.
- the molecular weight of the compound (A1) (including the compound (A1 ′)) is preferably from 100 to 10,000, more preferably from 200 to 1,000, from the viewpoints of low humidity, high gas barrier properties, and applicability of the curable composition. 300 to 500 are more preferable.
- the content of the compound (A1) is the total amount (100% by weight) of the curable compound of the present invention from the viewpoint of low moisture permeability, high gas barrier property, applicability of the curable composition, hardness of the cured product, and the like.
- it is preferably 5 to 80% by weight, more preferably 7 to 60% by weight, and further preferably 10 to 50% by weight.
- 5 to 60% by weight is preferable, 7 to 50% by weight is more preferable, and 10 to 45% by weight is further preferable.
- Compound (A2) is a compound having one functional group selected from the group consisting of one epoxy group, oxetane group, vinyl ether group and (meth) acryloyl group in one molecule, and a molecular weight of 100 to 1,000. is there.
- the molecular weight of the compound (A2) is 100 to 1000
- the curable composition is cured, the free volume in the cured product is packed as a side chain of the polymer to be produced, thereby reducing the moisture permeability and the high gas barrier. The effect which contributes to property is acquired.
- Examples of the cyclic skeleton in compound (A2) include those exemplified above for compound (A1). Among these, a benzene ring and a cyclohexane ring are preferable.
- a compound (A2) can be used individually by 1 type or in combination of 2 or more types.
- both the compound (A1) and the compound (A2) are used as the component (A), when the compound (A1) has a cationic polymerizable functional group, the compound (A2) also has a cationic polymerizable functional group, When the compound (A1) has a radical polymerizable functional group, the compound (A2) also preferably has a radical polymerizable functional group.
- both the compound (A1) and the compound (A2) are preferably epoxy groups (particularly preferably a glycidyl group).
- Examples of the compound (A2) include a compound (A2-1) having an aromatic ring and a cationic polymerizable functional group; a compound (A2-2) having an aromatic ring and a radical polymerizable functional group; an aliphatic ring. And a compound having a cation polymerizable functional group (A2-3); a compound having an aliphatic ring and a radical polymerizable functional group (A2-4); a compound having an alkyl group and a cation polymerizable functional group (A2- 5); a compound (A2-6) having an alkyl group and a radical polymerizable functional group.
- Examples of the compound (A2-1) having an aromatic ring and a cationic polymerizable functional group include glycidyl phenyl ether, o-, m-, or p-phenylphenol glycidyl ether, 2,3-, 2,4- 2,5-, 2,6-, 3,4-, or 3,5-diphenylphenol glycidyl ether, 2-phenyl-4-benzylphenylphenol glycidyl ether, 2-phenyl-5-benzylphenylphenol glycidyl ether, 2-phenyl-6-benzylphenylphenol glycidyl ether, 3-phenyl-5-benzylphenylphenol glycidyl ether, 3-phenyl-6-benzylphenylphenol glycidyl ether, 4-phenyl-2-benzylphenylphenol glycidyl ether, triphenyl Feno Compounds having a phenol skeleton and an epoxy group
- Examples of the compound (A2-2) having an aromatic ring and a radical polymerizable functional group include phenyl (meth) acrylate, phenylphenol (meth) acrylate, phenoxymethyl (meth) acrylate, (phenylphenoxy) methyl (meta ) Acrylate, (2-phenoxy) ethyl (meth) acrylate, (2-phenylphenoxy) ethyl (meth) acrylate and other compounds having one or two benzene rings and a (meth) acryloyl group; and halides thereof; Or these C1-9 alkyl substitution products etc. are mentioned.
- Examples of the C 1-9 alkyl substituent in the C 1-9 alkyl substituent include methyl, ethyl, propyl, and t-butyl groups.
- Examples of the halogen in the halide include F, Cl, Br and the like.
- Examples of the compound (A2-3) having an aliphatic ring and a cationically polymerizable functional group include C 5-20 cycloalkyl glycidyl ether compounds such as cyclohexyl glycidyl ether, dicyclohexyl glycidyl ether, tricyclohexyl glycidyl ether, and the like; C 5-20 cycloalkyl octenyl ether compounds such as ruether, dicyclohexyl octacenyl ether and tricyclohexyl octacenyl ether; C 5-20 cycloalkyl vinyl ether compounds such as cyclohexyl vinyl ether, dicyclohexyl vinyl ether and tricyclohexyl vinyl ether.
- the compound (A2-4) having an aliphatic ring and a radical polymerizable functional group for example, C 5-20 cycloalkyl (such as cyclohexyl (meth) acrylate, dicyclohexyl (meth) acrylate, tricyclohexyl (meth) acrylate) ( And a (meth) acrylate compound.
- C 5-20 cycloalkyl such as cyclohexyl (meth) acrylate, dicyclohexyl (meth) acrylate, tricyclohexyl (meth) acrylate
- a (meth) acrylate compound for example, C 5-20 cycloalkyl (such as cyclohexyl (meth) acrylate, dicyclohexyl (meth) acrylate, tricyclohexyl (meth) acrylate) ( And a (meth) acrylate compound.
- Examples of the compound (A2-5) having an alkyl group and a cationically polymerizable functional group include C 1-9 alkyl such as glycidyl methyl ether, glycidyl ethyl ether, propyl glycidyl ether, butyl glycidyl ether, and 2-ethylhexyl glycidyl ether.
- glycidyl ether compounds methyloxetane Se Tani ether, ethyl Oki Se Tani ether, propyl Oki Se Tani ether, C 1-9 alkyl Oki Se Tani ether compounds such as butyl Oki Se Tani ether; methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, C 1-9 alkyl vinyl ether compounds such as butyl vinyl ether Etc.
- the compound having an alkyl group and a radical polymerizable functional group (A2-6), for example, such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate C 1- 9 alkyl (meth) acrylate compounds and the like.
- Z 2 represents a group obtained by removing an OH group from a monovalent hydroxy compound (Z 2 OH), and R 2 is the same as R 1 described above.
- the compound represented by these is mentioned.
- Z 2 is preferably a group having a cyclic skeleton. Examples of the cyclic skeleton include those exemplified above.
- Examples of the hydroxy compound Z 2 OH include phenols having 1 to 3 benzene rings such as phenol, phenylphenol, diphenylphenol, and triphenylphenol; methylphenol, ethylphenol, propylphenol, n-butylphenol, and t-butylphenol.
- alkyl-substituted phenols and the like for example, C 1-9 alkyl-substituted phenols
- methylphenyl phenol, ethyl phenyl phenol, propyl phenylphenol, n- butyl phenylphenol, t- butyl phenyl phenol and the like alkyl-substituted phenyl phenols for example, C 1-9 alkyl-substituted phenyl phenol
- Compound (A2) is preferably a compound having an epoxy group, an oxetane group, a vinyl ether group, or a (meth) acryloyl group, and a benzene ring or a cyclohexane ring.
- glycidyl ether having 1 to 2 benzene rings such as glycidyl phenyl ether or o-phenylphenol glycidyl ether; benzene such as 2- (phenylphenoxy) ethyl (meth) acrylate (Meth) acrylate having 1 to 2 rings is preferred.
- the compound (A2) one functional group selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group and a (meth) acryloyl group having an aromatic ring and a molecular weight of 100 to 1000 is used. It is preferable that it is a compound (A2 ') which has.
- the molecular weight of the compound (A2) is preferably from 100 to 1,000, more preferably from 150 to 800, still more preferably from 170 to 600, from the viewpoints of low moisture permeability, high gas barrier properties, and applicability of the curable composition. 200 to 400 is particularly preferable.
- the content of the compound (A2) is 0 to 1400 weights with respect to the total amount (100 parts by weight) of the compound (A1) from the viewpoints of low moisture permeability, high gas barrier properties, and applicability of the curable composition.
- Parts preferably 70 to 850 parts by weight, more preferably 100 to 500 parts by weight.
- the content of the compound (A2) is preferably 0 to 70% by weight, more preferably 5 to 60% by weight, more preferably 10 to 50% by weight based on the total amount (100% by weight) of the curable compound of the present invention. More preferred is weight percent.
- the compound (A1) has two cyclic skeletons, and the compound (A2) has a cyclic skeleton.
- the compound (A1) has 2 cyclic skeletons
- compound (A2) has 2 cyclic skeletons
- compound (A1) has 5 cyclic skeletons
- a combination in which the compound (A2) has one cyclic skeleton can be given.
- Preferable combinations of the compound (A1) and the compound (A2) are specifically combinations of bisphenol F diglycidyl ether and glycidyl phenyl ether, bisphenol F diglycidyl ether and o-, m-, or p-phenylphenol.
- a combination with glycidyl ether and the like can be mentioned.
- the content of glycidyl phenyl ether as compound (A2) is 1 to 100 with respect to 100 parts by weight of bisphenol F diglycidyl ether as compound (A1). Part by weight is particularly preferred.
- the content of o-, m-, or p-phenylphenol glycidyl ether as compound (A2) is The amount is preferably 1 to 1000 parts by weight based on 100 parts by weight of bisphenol F diglycidyl ether as the compound (A1).
- the total content of the compound (A1) and the compound (A2) is preferably 5 to 80% by weight with respect to the total amount (100% by weight) of the curable compound of the present invention. % Is more preferable, and 20 to 60% by weight is more preferable.
- Component (B) is an alicyclic epoxy compound, that is, a compound having at least an alicyclic (aliphatic hydrocarbon ring) structure and an epoxy group in the molecule (in one molecule).
- a component (B) can be used individually by 1 type or in combination of 2 or more types.
- component (B) for example, a compound (B-1) having two or more cationically polymerizable functional groups and an aliphatic ring in one molecule; two or more radically polymerizable functional groups in one molecule; And a compound (B-2) having an aliphatic ring.
- Examples of the compound (B-1) include hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, dicyclohexyl diglycidyl ether, and bis (3,4-epoxycyclohexyl) methyl.
- Examples of the compound (B-2) include cyclohexane such as hydrogenated bisphenol A di (meth) acrylate, hydrogenated bisphenol F di (meth) acrylate, hydrogenated bisphenol S di (meth) acrylate, and dicyclohexyl di (meth) acrylate. And compounds having a ring and two (meth) acryloyl groups.
- the compound (B-1) (i) a compound having an epoxy group (alicyclic epoxy group) composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring, (ii) ) A compound in which an epoxy group is directly bonded to the alicyclic ring by a single bond, and (iii) a compound having an alicyclic ring and a glycidyl group.
- the compound having an epoxy group (alicyclic epoxy group) composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring (i) is arbitrarily selected from known or commonly used compounds. can do.
- alicyclic epoxy group a cyclohexene oxide group is preferable.
- a compound having a cyclohexene oxide group is preferable from the viewpoint of transparency and heat resistance.
- a compound represented by the following formula (3) (an alicyclic epoxy compound) is preferable.
- X represents a single bond or a linking group (a divalent group having one or more atoms).
- the linking group include a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, and a group in which a plurality of these are linked.
- Examples of the compound in which X in the formula (3) is a single bond include (2,3,2 ′, 3′-diepoxy) bicyclohexyl, (2,3,3 ′, 4′-diepoxy) bicyclohexyl, (3 , 4,3 ′, 4′-diepoxy) bicyclohexyl and the like, among which (3,4,3 ′, 4′-diepoxy) bicyclohexyl is preferred.
- Examples of the divalent hydrocarbon group include a linear or branched alkylene group having 1 to 18 carbon atoms and a divalent alicyclic hydrocarbon group.
- Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group.
- divalent alicyclic hydrocarbon group examples include 1,2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclopentylene group, And divalent cycloalkylene groups (including cycloalkylene groups) such as cyclohexylene group, 1,4-cyclohexylene group and cyclohexylene group.
- linking group X examples include a linking group containing an oxygen atom, specifically, —CO—, —O—CO—O—, —COO—, —O—, —CONH—; A group in which one or more of these groups are linked to one or more of divalent hydrocarbon groups, and the like.
- divalent hydrocarbon group examples include those exemplified above.
- Representative examples of the alicyclic epoxy compound represented by the formula (3) include compounds represented by the following formulas (3-1) to (3-10).
- the compound represented by the formula (3-1) [3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate] (for example, trade name “Celoxide 2021P” manufactured by Daicel Corporation) is particularly preferable. preferable.
- p and q each represents an integer of 1 to 30.
- R 3 in the following formula (3-5) is an alkylene group having 1 to 8 carbon atoms, and includes a methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, an isobutylene group, an s-butylene group, a pentylene group, Examples thereof include linear or branched alkylene groups such as a hexylene group, a heptylene group, and an octylene group. Among these, linear or branched alkylene groups having 1 to 3 carbon atoms such as a methylene group, an ethylene group, a propylene group, and an isopropylene group are preferable.
- N1 to n6 in the following formulas (3-9) and (3-10) each represents an integer of 1 to 30.
- examples of the alicyclic epoxy compound represented by the formula (3) include bis (3,4-epoxycyclohexylmethyl) ether. 2,2-bis (3,4-epoxycyclohexyl) propane, 1,2-bis (3,4-epoxycyclohexyl) ethane and the like.
- Examples of the compound (ii) in which an epoxy group is directly bonded to the alicyclic ring with a single bond include compounds represented by the following formula (4).
- R 4 is a group obtained by dividing s -OH from an s-valent alcohol, and s and r each represent a natural number.
- s-valent alcohol -
- the [R 4 (OH) s] 2,2- bis (hydroxymethyl) -1-polyhydric alcohols such as butanol (such as an alcohol of 1 to 15 carbon atoms).
- s is preferably 1 to 6, and r is preferably 1 to 30.
- each r in the group in () (in parentheses) may be the same or different.
- 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol for example, , Manufactured by Daicel Corporation, trade name “EHPE3150”, etc.
- Examples of the compound (iii) having an alicyclic ring and a glycidyl group include 2,2-bis [4- (2,3-epoxypropoxy) cyclohexyl] propane, 2,2-bis [3,5-dimethyl- Compound obtained by hydrogenating bisphenol A type epoxy compound such as 4- (2,3-epoxypropoxy) cyclohexyl] propane (hydrogenated bisphenol A type epoxy compound); bis [o, o- (2,3-epoxypropoxy) cyclohexyl ] Methane, bis [o, p- (2,3-epoxypropoxy) cyclohexyl] methane, bis [p, p- (2,3-epoxypropoxy) cyclohexyl] methane, bis [3,5-dimethyl-4- ( 2,3-epoxypropoxy) cyclohexyl] compounds obtained by hydrogenating bisphenol F-type epoxy compounds such as methane (Hydrogenated bisphenol F type
- the molecular weight is preferably 100 to 500, more preferably 150 to 400, from the viewpoint of the curing rate of the curable composition, the applicability of the curable composition, the outgas suppression, and the like. 180 to 300 are more preferable.
- the component (B) is most preferably a compound having two or more alicyclic epoxy groups in one molecule and having a molecular weight of 100 to 500.
- the component (B) is a compound having an ester group and / or a carbonate group, and the total amount of the curable compound (100 % By weight) is preferably 30% by weight or less, more preferably a compound having no ester group and / or carbonate group.
- the content of the component (B) is based on the total amount (100% by weight) of the curable compound of the present invention. 20 to 95% by weight is preferable, 30 to 90% by weight is more preferable, and 40 to 80% by weight is further preferable. Moreover, content of a component (B) is the whole quantity (100 weight%) of the curable composition of this invention from viewpoints of the cure rate of a curable composition, the applicability
- the component (C) in the present invention may be a curing catalyst that has a cation component having an aromatic ring and has an anion component whose central element is boron or phosphorus and generates an acid by light or heat.
- a curing catalyst that has a cationic component having the above aromatic ring and has an anionic component in which the central element is boron or phosphorus and generates an acid by light or heat may be used.
- aromatic ring examples include a monovalent or divalent phenyl group, naphthyl group, anthracenyl group, and the like.
- the aromatic ring includes a linear or branched C 1-12 alkyl group, linear or You may have substituents, such as a branched C1-12 alkoxyl group, a halogen atom, -OH group, -COOH group, or a linear or branched C1-12 alkylester group.
- the cation component examples include aromatic diazonium salts, aromatic iodonium salts, aromatic sulfonium salts, aromatic phosphonium salts, aromatic selenium salts, aromatic oxonium salts, aromatic ammonium salts, and the like.
- aromatic diazonium salts aromatic iodonium salts
- aromatic sulfonium salts aromatic phosphonium salts
- aromatic selenium salts aromatic oxonium salts
- aromatic ammonium salts and the like.
- an aromatic sulfonium salt is preferable because a cured product having excellent curability can be formed.
- the anion component is not particularly limited, but from the viewpoint of the catalytic activity of the curing catalyst, it preferably has 3 or more aromatics, more preferably 4 or more aromatics, and 5 or more aromatics. More preferably, it has.
- the aromatic ring include an aromatic group having 6 to 30 carbon atoms and having a halogen substituent.
- the aromatic ring include a phenyl group, a naphthyl group, and an anthracenyl group.
- the halogen substituent include chlorine and fluorine.
- aromatic ring examples include a pentafluorophenyl group, a 2- (trifluoromethyl) phenyl group, a 3- (trifluoromethyl) phenyl group, a 4- (trifluoromethyl) phenyl group, and 2,3-di ( Trifluoromethyl) phenyl group, 2,4-di (trifluoromethyl) phenyl group, 2,5-di (trifluoromethyl) phenyl group, 2,6-di (trifluoromethyl) phenyl group, 3,4- A di (trifluoromethyl) phenyl group, a 3,5-di (trifluoromethyl) phenyl group and the like can be mentioned.
- the anion component is not particularly limited, but from the viewpoint of the catalytic activity of the curing catalyst, the central element is preferably boron or phosphorus.
- the central element is preferably boron or phosphorus.
- the component (C) preferably has a cation component having three or more aromatic rings and an anion component whose central element is boron or phosphorus.
- the component (C) contained in the curable composition of the present invention is not particularly limited, but a photocationic polymerization initiator or a thermal cationic polymerization initiator is preferable.
- a component (C) can be used individually by 1 type or in combination of 2 or more types.
- the cationic photopolymerization initiator is a cationic photopolymerization initiator that generates a cationic species by light irradiation and initiates a curing reaction of the cationically curable compound.
- the cationic photopolymerization initiator is composed of a cation moiety that absorbs light and an anion moiety that is a source of acid generation.
- a photocationic polymerization initiator can be used individually by 1 type or in combination of 2 or more types.
- photocationic polymerization initiator of the present invention examples include diazonium salt compounds, iodonium salt compounds, sulfonium salt compounds, phosphonium salt compounds, selenium salt compounds, oxonium salt compounds, ammonium salt compounds, bromine salts. System compounds and the like.
- a sulfonium salt compound is preferable in that a cured product having excellent curability can be formed.
- the cation moiety of the sulfonium salt compound include arylsulfonium ions (particularly, triarylsulfonium ions) such as triphenylsulfonium ions, diphenyl [4- (phenylthio) phenyl] sulfonium ions, and tri-p-trisulfonium ions. Is mentioned.
- a photocationic polymerization initiator for example, BF 4 ⁇ , B (C 6 F 5 ) 4 ⁇ , PF 6 ⁇ , [(Rf) n PF 6-n ] ⁇ (Rf: 80% of hydrogen atoms)
- n an integer of 1 to 5
- AsF 6 ⁇ , SbF 6 ⁇ pentafluorohydroxyantimonate and the like.
- Examples of the cationic photopolymerization initiator include diphenyl [4- (phenylthio) phenyl] sulfonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl] sulfonium hexafluorophosphate, and diphenyl [4- (phenylthio) phenyl.
- thermal cationic polymerization initiator examples include diazonium salt compounds, iodonium salt compounds, sulfonium salt compounds, phosphonium salt compounds, selenium salt compounds, oxonium salt compounds, ammonium salt compounds, bromine salt compounds, and the like. Is mentioned.
- a thermal cationic polymerization initiator can be used individually by 1 type or in combination of 2 or more types.
- thermal cationic polymerization initiator examples include a compound of a metal such as aluminum or titanium and a silanol such as triphenylsilanol of acetoacetic acid or diketones and a chelate compound, or a metal such as aluminum or titanium and acetoacetic acid or diketone.
- a compound of a chelate compound with a phenol and a phenol such as bisphenol S may be used.
- commercially available products include “Sun Aid SI-45”, “Sun Aid SI-47”, “Sun Aid SI-60”, “Sun Aid SI-60L”, “Sun Aid SI-80”, and “Sun Aid SI-80L”.
- the content of the component (C) is not particularly limited, but is preferably 0.01 to 8 parts by weight, preferably 0.1 to 5 parts by weight with respect to the total amount (100 parts by weight) of the curable compound of the present invention. Part is more preferable, 0.2 to 4 parts by weight is further preferable, and 0.5 to 3 parts by weight is particularly preferable.
- it is 0.01 part by weight or more, the curing rate of the curable composition can be increased, curing failure can be prevented, and low permeability, high gas barrier property, heat resistance, etc. can be contributed. Further, if it is 8% by weight or less, it is advantageous in terms of cost and can contribute to suppression of non-uniformity of reaction and suppression of outgas.
- the content of the component (B) is 30 to 95% by weight relative to the total amount (100% by weight) of the curable composition, and the content of the component (C) is the total amount (100% of the curable composition).
- % By weight) is preferably 0.01 to 8% by weight.
- the curable composition By selecting from the above range for the type and content of the component (C), an effect of increasing the curing rate of the curable composition can be obtained. On the other hand, for outgas, an effect of promoting the generation thereof is obtained. is there. On the other hand, by selecting the type, molecular weight, content, and the like of the component (B) from the above range, the curable composition is suppressed while outgassing is reduced by reducing the content of the component (C). Therefore, an excellent cured product having low moisture permeability, high gas barrier properties, heat resistance, curability, cost, and outgas suppression can be obtained.
- the curable composition of the present invention may contain a curing accelerator that accelerates the curing rate.
- a curing accelerator that accelerates the curing rate.
- the curing accelerator well-known and commonly used curing accelerators can be used.
- DBU 1,8-diazabicyclo [5.4.0] undecene-7
- salts thereof for example, phenol salts, octyls) Acid salt, p-toluenesulfonate, tetraphenylborate salt
- tertiary amine such as benzyldimethylamine, 2,4,6-tris (dimethylaminomethyl) phenol, N, N-dimethylcyclohexylamine; 2-ethyl-4-methylimidazole,
- U-CAT SA 506, U-CAT SA 102, U-CAT 5003, U-CAT 18X (above, manufactured by San Apro Co., Ltd.), TPP-K, TPP-MK (above, Hokuko Chemical) are used as curing accelerators.
- Commercial products such as Kogyo Co., Ltd.) PX-4ET (Nihon Kagaku Kogyo Co., Ltd.) can also be used.
- the content of the curing accelerator is from 0.05 to the total amount (100% by weight) of the curable composition of the present invention from the viewpoints of the curing acceleration effect of the curable composition, prevention of coloring of the cured product, and the like. 5 wt% is preferable, 0.1 to 3 wt% is more preferable, 0.2 to 3 wt% is further preferable, and 0.25 to 2.5 wt% is particularly preferable.
- the curable composition of the present invention may contain a radical photopolymerization initiator.
- the photo radical polymerization initiator include benzophenone, acetophenone benzyl, dibenzyl methyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxyacetophenone, dimethoxyphenylacetophenone, diethoxyacetophenone, diphenylyl disulfate.
- radical photopolymerization initiators can be used alone or in combination of two or more. Moreover, a photosensitizer can be added as needed.
- radical photopolymerization initiators from the viewpoint of sensitivity and chemical resistance, a combination of an imidazole compound and an aminobenzene derivative, 2-amino-2-benzoyl-1-phenylalkane compound, halomethylated triazine compound, halomethyloxadi An azole compound or the like is preferable.
- the curable composition of the present invention may contain a thermal radical polymerization initiator.
- the thermal radical polymerization initiator include organic peroxides.
- organic peroxides dialkyl peroxides, acyl peroxides, hydroperoxides, ketone peroxides, peroxy esters and the like can be used.
- organic peroxides include benzoyl peroxide, t-butylperoxy-2-ethylhexanate, 2,5-dimethyl-2,5-di (2-ethylhexanoyl) peroxyhexane, t -Butyl peroxybenzoate, t-butyl peroxide, cumene hydroperoxide, dicumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-dibutylperoxyhexane, 2,4-dichloro Benzoyl peroxide, di-t-butyl peroxide di-isopropylbenzene, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, methyl ethyl ketone peroxide, 1,1,3,3- Examples include tetramethylbutyl peroxy-2-ethylhexanoate.
- naphthenic acid such as cobalt naphthenate, manganese naphthenate, zinc naphthenate, cobalt octenoate and the like
- metal salts such as cobalt octenoic acid, manganese, lead, zinc, vanadium, etc.
- tertiary amines such as dimethylaniline can be used.
- the content of the photo radical polymerization initiator or the thermal radical polymerization initiator is preferably 0.1 to 5% by weight, preferably 0.5 to 4%, based on the total amount (100% by weight) of the curable composition of the present invention. Weight percent is more preferred.
- the radical photopolymerization initiator or the thermal radical polymerization initiator can be used alone or in combination of two or more.
- the curable composition of the present invention may contain a curing retardant.
- the curing retarder include azole compounds such as pyrrole, pyrazole, 3,5-dimethylpyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole; ethylene glycol, propylene glycol, polyethylene glycol And (poly) alkylene glycols such as polypropylene glycol and butylene glycol, polyol compounds such as glycerin, polyglycerin, pentaerythritol, polycaprolactone polyol, and crown ether (particularly, aliphatic polyol compounds).
- the pot life and curing start time after irradiating the curable composition of the present invention with light can be controlled. More specifically, the curing retarder can trap the cations generated from the photocationic polymerization initiator by UV irradiation to suppress the cationic polymerization of the curable compound, and release the cations when heat-treated. And has the effect of advancing cationic polymerization of the curable compound.
- azole compounds are preferable in that they do not cause outgassing, and by adding to the curable composition, the pot life of the curable composition can be freely controlled, and the curable By irradiating the coating film of the composition with UV, and then applying the heat treatment to the organic EL element, the organic EL element can be sealed without being directly exposed to UV, and low outgassing and moisture resistance
- the organic EL element can be sealed with a cured product having the above.
- the used amount (blending amount) of the curing retarder is, for example, about 5 to 25% by weight, preferably 10 to 25% by weight, based on the used amount of the cationic photopolymerization initiator (the total amount when containing two or more kinds). .
- the component (D) in the present invention is a conductive fiber-coated particle containing a particulate material and a fibrous conductive material (sometimes referred to as “conductive fiber”) that covers the particulate material.
- “cover” means a state in which the conductive fibers cover part or all of the surface of the particulate matter.
- the conductive fiber-coated particles of the present invention it is only necessary that the conductive fibers cover at least a part of the surface of the particulate matter. For example, there are more uncovered portions than covered portions. You may do it.
- the particulate matter and the conductive fiber are not necessarily in contact with each other, but usually a part of the conductive fiber is in contact with the surface of the particulate matter. Yes.
- FIG. 1 is an example of a scanning electron microscope image of the conductive fiber-coated particles of the present invention.
- the conductive fiber-coated particles of the present invention at least a part of the particulate material (the true spherical material in FIG. 1) is coated with the conductive fiber (the fibrous material in FIG. 1). It has a configuration.
- the particulate matter constituting the conductive fiber-coated particles of the present invention is a particulate structure.
- the material (raw material) constituting the particulate matter is not particularly limited, and examples thereof include known or commonly used materials such as metal, plastic, rubber, ceramic, glass, and silica.
- a transparent material such as transparent plastic, glass, and silica
- a transparent plastic in terms of flexibility.
- the transparent plastic includes a thermosetting resin and a thermoplastic resin.
- the thermosetting resin include poly (meth) acrylate resin; polystyrene resin; polycarbonate resin; polyester resin; polyurethane resin; epoxy resin; polysulfone resin; amorphous polyolefin resin; divinylbenzene, hexatriene, divinyl ether, Divinyl sulfone, diallyl carbinol, alkylene diacrylate, oligo or polyalkylene glycol diacrylate, oligo or polyalkylene glycol dimethacrylate, alkylene triacrylate, alkylene tetraacrylate, alkylene trimethacrylate, alkylene tetramethacrylate, alkylene bisacrylamide, alkylene bismethacryl Multifunctional monomers such as amide and polybutadiene oligomer modified with both ends Germany or polymerized with other monomers obtained network polymer; phenol formaldehyde resins, melamine formalde
- thermoplastic resin examples include ethylene / vinyl acetate copolymer, ethylene / vinyl acetate / unsaturated carboxylic acid copolymer, ethylene / ethyl acrylate copolymer, ethylene / methyl methacrylate copolymer, and ethylene / acrylic acid.
- Copolymer ethylene / methacrylic acid copolymer, ethylene / maleic anhydride copolymer, ethylene / aminoalkyl methacrylate copolymer, ethylene / vinyl silane copolymer, ethylene / glycidyl methacrylate copolymer, ethylene / hydroxyethyl methacrylate
- Examples include copolymers, methyl (meth) acrylate / styrene copolymers, acrylonitrile / styrene copolymers, and the like.
- the shape of the particulate material is not particularly limited.
- it is spherical (true sphere, approximately true sphere, elliptical sphere, etc.), polyhedron, rod (column, prism, etc.), flat plate, flake shape, indefinite Examples include shape.
- the conductive fiber-coated particles can be produced with high productivity, easily dispersed uniformly with the curable compound, and easy to impart conductivity to the entire resin.
- the shape is preferably spherical or rod-like, and particularly preferably spherical (particularly true spherical).
- the average aspect ratio of the particulate material is not particularly limited, but is preferably less than 20 (for example, 1 or more and less than 20), particularly preferably 1 to 10. When the average aspect ratio exceeds the above range, it may be difficult to develop excellent conductivity in the curable compound by blending a small amount of conductive fiber-coated particles.
- the average aspect ratio of the particulate matter is, for example, a sufficient number of particles (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It can be measured by taking an electron microscope image of the particulate matter, measuring the aspect ratio of these particulate matter, and arithmetically averaging them.
- the configuration of the particulate matter is not particularly limited, and may be a single-layer configuration or a multilayer (multi-layer) configuration.
- the particulate matter may be any of solid particles, hollow particles, porous particles, and the like.
- the average particle diameter of the particulate matter is not particularly limited, but is preferably 0.1 to 100 ⁇ m, more preferably 1 to 50 ⁇ m, and further preferably 5 to 30 ⁇ m.
- the average particle diameter is below the above range, it may be difficult to develop excellent conductivity by blending a small amount of conductive fiber-coated particles.
- the average particle diameter exceeds the above range, the average particle diameter becomes larger than the thickness of the sealing layer of the organic EL element, and it tends to be difficult to form a coating film having a uniform thickness.
- the average particle diameter in the long axis (longest long axis) direction is controlled within the above range.
- the average particle diameter of the particulate matter is a median diameter (d50) by a laser diffraction / scattering method.
- the particulate matter is preferably transparent.
- the total light transmittance in the visible light wavelength region of the particulate matter is not particularly limited, but is preferably 70% or more, and particularly preferably 75% or more. When the total light transmittance is below the above range, the transparency of the cured product (including the conductive fiber-coated particles) may be lowered.
- the total light transmittance in the visible light wavelength region of the particulate matter is determined by polymerizing the monomer that is the raw material of the particulate matter in a temperature range of 80 to 150 ° C. between glasses to form a flat plate having a thickness of 1 mm. It is obtained by measuring the total light transmittance of the flat plate in the visible light wavelength region according to JIS K7361-1.
- the particulate material preferably has flexibility.
- The% compressive strength is, for example, 10 kgf / mm 2 or less, preferably 5 kgf / mm 2 or less, particularly preferably 3 kgf / mm 2 or less.
- the conductive fiber-coated particles containing particulate matter having a 10% compressive strength in the above range can be deformed following a fine concavo-convex structure by applying pressure.
- the curable composition containing the conductive fiber-coated particles is cured into a shape having a fine concavo-convex structure, the particulate matter can be spread to the details, and the portion where the conductivity becomes poor This is because generation can be prevented.
- the refractive index of the particulate matter is not particularly limited, but is preferably 1.4 to 2.7, particularly preferably 1.5 to 1.8.
- the refractive index of the particulate matter is such that when the particulate matter is a plastic particle, a raw material of the particulate matter is polymerized at 80 to 150 ° C. to prepare a test piece of 20 mm in length ⁇ 6 mm in width. Using monobromonaphthalene as a liquid, the prism and the test piece are in close contact with each other, using a multi-wavelength Abbe refractometer (trade name “DR-M2”, manufactured by Atago Co., Ltd.), 20 ° C., sodium It can be determined by measuring the refractive index at the D line.
- DR-M2 multi-wavelength Abbe refractometer
- the said particulate matter has a small refractive index difference with the hardened
- the absolute value of the refractive index difference (at 25 ° C., wavelength 589.3 nm) between the particulate material and the cured product of the curable compound of the present invention is 0.1 or less (preferably 0.5 or less, particularly Preferably it is 0.02 or less. That is, it is preferable that the conductive fiber-coated particles and the curable compound contained in the curable composition of the present invention satisfy the following formula.
- Refractive index of particulate matter constituting conductive fiber-coated particles at 25 ° C., wavelength 589.3 nm
- -refractive index of cured product of curable compound at 25 ° C., wavelength 589.3 nm
- the coefficient of variation in the volume-based particle size distribution of the particulate matter is calculated from the following equation.
- the particle size distribution can be measured using a particle size distribution measuring device (trade name “Coulter Multisizer”, manufactured by Beckman Coulter, Inc.).
- Coefficient of variation (CV value) (%) (S2 / Dn) ⁇ 100 (Wherein, S2 represents the standard deviation in the volume-based particle size distribution, and Dn represents the median diameter (D50) based on the volume)
- the particulate matter can be produced by a known or common method, and the production method is not particularly limited.
- metal particles it can be produced by a vapor phase method such as a CVD method or a spray pyrolysis method, or a wet method using a chemical reduction reaction.
- plastic particles for example, a method of polymerizing monomers constituting the resin (polymer) exemplified above by a known polymerization method such as a suspension polymerization method, an emulsion polymerization method, a seed polymerization method, or a dispersion polymerization method. Etc. can be manufactured.
- thermosetting resin examples include, for example, trade names “Techpolymer MBX series”, “Techpolymer BMX series”, “Techpolymer ABX series”, “Techpolymer ARX series”, and “Techpolymer AFX series”.
- the conductive fiber constituting the conductive fiber-coated particle of the present invention is a fibrous structure (linear structure) having conductivity.
- the shape of the conductive fiber is not particularly limited as long as it is fibrous (fibrous), but the average aspect ratio is preferably 10 or more (for example, 20 to 5000), more preferably 50 to 3000, and more preferably 100 to 1000 is more preferable. When the average aspect ratio is less than the above range, it may be difficult to develop excellent conductivity by blending a small amount of conductive fiber-coated particles.
- the average aspect ratio of the conductive fibers can be measured by the same procedure as the average aspect ratio of the particulate matter.
- the concept of “fibrous” in the conductive fiber includes shapes of various linear structures such as “wire” and “rod”. In the present specification, fibers having an average thickness of 1000 nm or less may be referred to as “nanowires”.
- the average thickness (average diameter) of the conductive fibers is not particularly limited, but is preferably 1 to 400 nm, more preferably 10 to 200 nm, and further preferably 50 to 150 nm. When the average thickness is less than the above range, the conductive fibers are likely to aggregate and it may be difficult to produce the conductive fiber-coated particles. On the other hand, if the average thickness exceeds the above range, it may be difficult to coat the particulate matter, and it may not be possible to obtain conductive fiber-coated particles efficiently.
- the average thickness of the conductive fibers is an electron with respect to a sufficient number of conductive fibers (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It can be measured by taking a microscopic image, measuring the thickness (diameter) of these conductive fibers, and arithmetically averaging them.
- the average length of the conductive fibers is not particularly limited, but is preferably 1 to 100 ⁇ m, more preferably 5 to 80 ⁇ m, and still more preferably 10 to 50 ⁇ m. If the average length is less than the above range, it may be difficult to coat the particulate matter, and it may not be possible to obtain conductive fiber-coated particles efficiently. On the other hand, if the average length exceeds the above range, the conductive fibers may adhere to or be adsorbed on a plurality of particles, which may cause aggregation (deterioration of dispersibility) of the conductive fiber-coated particles.
- the average length of the conductive fibers is an electron for a sufficient number of conductive fibers (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It can be measured by taking a microscopic image, measuring the length of these conductive fibers, and arithmetically averaging them. Note that the length of the conductive fiber should be measured in a linearly stretched state, but in reality it is often bent, so the conductive fiber can be measured using an image analyzer from an electron microscope image.
- the material (material) constituting the conductive fiber may be any material having conductivity, and examples thereof include metals, semiconductors, carbon materials, and conductive polymers.
- the metal examples include known and commonly used metals such as gold, silver, copper, iron, nickel, cobalt, tin, and alloys thereof. In the present invention, among them, silver is preferable because of its excellent conductivity.
- Examples of the semiconductor include known or commonly used semiconductors such as cadmium sulfide and cadmium selenide.
- Examples of the carbon material include known or commonly used carbon materials such as carbon fibers and carbon nanotubes.
- the conductive polymer examples include polyacetylene, polyacene, polyparaphenylene, polyparaphenylene vinylene, polypyrrole, polyaniline, polythiophene, and derivatives thereof (for example, an alkyl group, a hydroxyl group, a carboxyl group, a common polymer skeleton, Those having a substituent such as ethylenedioxy group; specifically, polyethylenedioxythiophene and the like).
- polyacetylene, polyaniline and derivatives thereof, polypyrrole and derivatives thereof, and polythiophene and derivatives thereof are preferable.
- the conductive polymer may contain a known or commonly used dopant (for example, an acceptor such as a halogen, a halide, or a Lewis acid; a donor such as an alkali metal or an alkaline earth metal).
- the conductive fiber of the present invention is preferably a conductive nanowire, in particular, at least one conductive nanowire selected from the group consisting of metal nanowires, semiconductor nanowires, carbon fibers, carbon nanotubes, and conductive polymer nanowires, In particular, silver nanowires are most preferable in terms of excellent conductivity.
- the conductive fiber can be produced by a known or conventional production method.
- the metal nanowire can be manufactured by a liquid phase method, a gas phase method, or the like. More specifically, silver nanowires are described in, for example, Mater. Chem. Phys. 2009, 114, 333-338, Adv. Mater. 2002, 14, P833-837, Chem. Mater. 2002, 14, P4736-4745, and JP-T 2009-505358.
- the gold nanowire can be manufactured, for example, by the method described in JP-A-2006-233252.
- a copper nanowire can be manufactured by the method as described in Unexamined-Japanese-Patent No. 2002-266007, for example.
- cobalt nanowire can be manufactured by the method as described in Unexamined-Japanese-Patent No. 2004-148771, for example.
- a semiconductor nanowire can be manufactured by the method as described in Unexamined-Japanese-Patent No. 2010-208925, for example.
- the carbon fiber can be produced, for example, by the method described in JP-A-06-081223.
- the carbon nanotube can be produced, for example, by the method described in JP-A-06-157016.
- the said conductive polymer nanowire can be manufactured by the method of Unexamined-Japanese-Patent No. 2006-241334, Unexamined-Japanese-Patent No. 2010-76044, for example.
- a commercial item can also be used as the conductive fiber.
- the conductive fiber-coated particles of the present invention can be produced by mixing the particulate matter and conductive fibers in a solvent.
- examples of the method for producing conductive fiber-coated particles of the present invention include the following methods (1) to (4).
- (1) Mixing a dispersion in which the particulate matter is dispersed in a solvent (referred to as “particle dispersion”) and a dispersion in which the conductive fibers are dispersed in a solvent (referred to as “fiber dispersion”). Then, if necessary, the solvent is removed to obtain the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed if necessary, and the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed if necessary, and the conductive fiber-coated particles of the present invention (or a dispersion of the conductive fiber-coated particles).
- the solvent is removed as necessary to disperse the conductive fiber-coated particles of the present invention (or dispersion of the conductive fiber-coated particles). Liquid).
- the above method (1) is preferable because homogeneous conductive fiber-coated particles can be obtained.
- Examples of the solvent used in producing the conductive fiber-coated particles of the present invention include water; alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; acetone, methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK).
- alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
- MEK methyl ethyl ketone
- MIBK methyl isobutyl ketone
- Ketones such as benzene, toluene, xylene and ethylbenzene; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; esters such as methyl acetate, ethyl acetate, isopropyl acetate and butyl acetate; N, N- Amides such as dimethylformamide and N, N-dimethylacetamide; nitriles such as acetonitrile, propionitrile, and benzonitrile. These can be used individually by 1 type or in combination of 2 or more types (that is, as a mixed solvent). In the present invention, alcohol and ketone are particularly preferable.
- the curable compound of the present invention for example, epoxy compound
- the curable compound of the present invention can be used as long as it is liquid.
- a curable composition containing the curable compound and the conductive fiber-coated particles of the present invention can be obtained without going through the step of removing the solvent.
- the viscosity of the solvent is not particularly limited, but from the viewpoint of efficiently producing conductive fiber-coated particles, the viscosity at 25 ° C. is preferably 10 cP or less (for example, 0.1 to 10 cP), and 0.5 to 5 cP. Is particularly preferred.
- the viscosity of the solvent at 25 ° C. can be measured using, for example, an E-type viscometer (trade name “VISCONIC”, manufactured by Tokimec Co., Ltd.) (rotor: 1 ° 34 ′ ⁇ R24, rotation speed: 0.5 rpm, measurement temperature: 25 ° C.).
- the boiling point at 1 atm of the solvent is preferably 200 ° C. or lower, more preferably 150 ° C. or lower, and further preferably 120 ° C. or lower in that the conductive fiber-coated particles can be efficiently produced.
- the content of the particulate matter when mixing the particulate matter and the conductive fiber in the solvent is, for example, about 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 100 parts by weight of the solvent. It is. By controlling the content of the particulate matter within the above range, the conductive fiber-coated particles can be generated more efficiently.
- the content of the conductive fiber when mixing the particulate matter and the conductive fiber in the solvent is, for example, about 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight with respect to 100 parts by weight of the solvent. It is. By controlling the content of the conductive fiber within the above range, the conductive fiber-coated particles can be generated more efficiently.
- the ratio of the particulate matter and the conductive fiber when mixing the particulate matter and the conductive fiber in the solvent is the ratio of the surface area of the particulate matter to the projected area of the conductive fiber [surface area / projected area]. However, the ratio is preferably about 100/1 to 100/100, or 100/10 to 100/50. By controlling the ratio within the above range, the conductive fiber-coated particles can be generated more efficiently.
- the surface area of the particulate matter can be measured by a method of multiplying the specific surface area obtained by the BET method (based on JIS Z8830) by the mass (amount of use) of the particulate matter.
- the projected area of the conductive fibers is a sufficient number (for example, 100 or more, preferably 300 or more; in particular, 100 or 300) using an electron microscope (SEM, TEM). It can be measured by taking an electron microscope image of the conductive fibers, calculating the projected area of these conductive fibers using an image analysis device, and arithmetically averaging them.
- SEM electron microscope
- the conductive fiber-coated particles can be obtained as a solid by further removing the solvent.
- the removal of the solvent is not particularly limited, and can be performed by a known or conventional method such as heating, distillation under reduced pressure, or the like.
- the solvent is not necessarily removed, and for example, it can be used as it is as a dispersion of the conductive fiber-coated particles of the present invention.
- the conductive fiber-coated particles of the present invention can be manufactured by mixing raw materials (particulate matter and conductive fibers) in a solvent, and do not require a complicated process. This is advantageous.
- the conductive fiber-coated particles of the present invention can be produced more efficiently.
- a particulate material having an average circumference B [ ⁇ m] and an average length (B ⁇ 1/6) [ ⁇ m] or more preferably B [ ⁇ m It is preferable to use the above-mentioned conductive fibers.
- the average perimeter of the particulate matter is a sufficient number (for example, 100 or more, preferably 300 or more; in particular, 100, 300, etc.) using an electron microscope (SEM, TEM). It is obtained by taking an electron microscope image of the substance, measuring the circumference of these particulate substances, and calculating the arithmetic average.
- SEM electron microscope
- the ratio of the particulate matter and the conductive fiber constituting the conductive fiber-coated particle of the present invention is such that the ratio of the surface area of the particulate matter to the projected area of the conductive fiber [surface area / projected area] is, for example, 100/1 ⁇
- the ratio is preferably about 100/100 (particularly 100/10 to 100/50).
- the conductive fiber-coated particles of the present invention have the above-described configuration, they can impart excellent conductivity (especially conductivity in the thickness direction) with a small amount of addition, and are a cured product excellent in transparency and conductivity. Can be formed.
- grain is made into fine unevenness
- the conductive fiber-coated particles are deformed following the concavo-convex structure and spread to details, the occurrence of a portion with poor conductivity can be prevented, and the conductive performance is excellent.
- An organic EL device can be formed.
- the conductive fiber-coated particles can be used singly or in combination of two or more.
- the content (blending amount) of the conductive fiber-coated particles (component (D)) in the curable composition is, for example, about 0.01 to 30 parts by weight, preferably 100 parts by weight with respect to 100 parts by weight of the curable compound of the present invention. Is 0.1 to 20 parts by weight, more preferably 0.3 to 15 parts by weight, and particularly preferably 0.5 to 5 parts by weight. If the content of the conductive fiber-coated particles is less than 0.01 parts by weight, the conductivity of the obtained cured product may be insufficient depending on the application. On the other hand, when the content of the conductive fiber-coated particles exceeds 30 parts by weight, the transparency of the obtained cured product may be insufficient depending on the application.
- the content of the conductive fiber-coated particles (component (D)) in the curable composition of the present invention is preferably 0.1 to 60% by volume with respect to the total amount (100% by volume) of the curable composition.
- the amount is preferably 0.2 to 60% by volume, more preferably 0.3 to 50% by volume, and particularly preferably 0.3 to 40% by volume.
- the conductivity in the curable composition of the present invention when anisotropic conductivity (electric anisotropy that has conductivity in a specific direction but is insulative in other directions) is developed, the conductivity in the curable composition of the present invention.
- the content of the fiber-coated particles (component (D)) is preferably 30% by volume or less (for example, 0.1 to 10% by volume) with respect to the total amount (100% by volume) of the curable composition of the present invention, Particularly preferred is 0.3 to 5% by volume.
- the content of the conductive fiber-coated particles (component (D)) can be estimated by, for example, dividing the total weight of the conductive fiber-coated particles by the density of the particles (conductive fiber-coated particles).
- the content (particulate amount) of the particulate matter (particulate matter contained in the conductive fiber-coated particles) in the curable composition of the present invention is, for example, 0.09 to 6 with respect to 100 parts by weight of the curable compound.
- the content is preferably 0.1 to 5% by volume, particularly preferably 0.3 to 3% by volume, and most preferably 0.4 to 2% by volume. If the content of the conductive fiber-coated particles is less than 0.02% by volume, the conductivity of the obtained cured product may be insufficient depending on the application. On the other hand, if the content of the conductive fiber-coated particles exceeds 7% by volume, the resulting cured product may have insufficient transparency depending on the application.
- the conductive fiber content (blending amount) in the curable composition of the present invention is, for example, about 0.01 to 1.0 part by weight, preferably 0.02 to 0 part per 100 parts by weight of the curable compound. 8 parts by weight, more preferably 0.03 to 0.6 parts by weight, still more preferably 0.03 to 0.4 parts by weight, particularly preferably 0.03 to 0.2 parts by weight.
- the curable composition of the present invention contains conductive fibers in a state of being coated with particulate matter, a cured product having sufficient conductivity even when the amount of the conductive material used is reduced to the above range. Can be formed. Therefore, it is possible to reduce the decrease in transparency of the cured product caused by containing a material having conductivity, and it is possible to greatly reduce the cost occupied by the material having conductivity. .
- the curable composition of the present invention may further contain a conductive substance other than the conductive fiber-coated particles of the present invention (sometimes referred to as “other conductive substance”).
- a conductive substance other than the conductive fiber-coated particles of the present invention sometimes referred to as “other conductive substance”.
- other conductive substances known or commonly used conductive substances can be used, and are not particularly limited.
- the above conductive fibers may be used.
- the content (blending amount) of the other conductive substance (for example, conductive fibers) in the curable composition of the present invention is, for example, about 0 to 10 parts by weight with respect to 100 parts by weight of the conductive fiber-coated particles.
- the amount is preferably 0 to 5 parts by weight, more preferably 0 to 1 part by weight.
- the curable composition of the present invention may contain various additives within a range that does not impair the effects of the present invention.
- the additive include hydroxyl group compounds such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin; silicone-based and fluorine-based antifoaming agents; leveling agents; ⁇ -glycidoxypropyltrimethoxysilane, and 3-mercaptopropyl.
- Silane coupling agents such as trimethoxysilane; Surfactants; Inorganic fillers such as silica and alumina; Flame retardants; Colorants; Antioxidants; Ultraviolet absorbers; Ion adsorbents; Pigments; Phosphors; Of conventional additives.
- the curable composition of this invention is obtained by mixing each said component uniformly.
- each component uses a generally known mixing device such as a revolving type stirring deaerator, a homogenizer, a planetary, a three roll mill, a bead mill, and an ultrasonic wave.
- a generally known mixing device such as a revolving type stirring deaerator, a homogenizer, a planetary, a three roll mill, a bead mill, and an ultrasonic wave.
- the curable composition of the present invention comprises conductive fiber-coated particles (component (D) (or a dispersion of conductive fiber-coated particles), a curable compound, and other components as necessary in the above-mentioned general composition.
- conductive fiber-coated particles component (D) (or a dispersion of conductive fiber-coated particles), a curable compound, and other components as necessary in the above-mentioned general composition.
- Step A Step of obtaining a conductive fiber-coated particle dispersion by mixing particulate matter and fibrous conductive material in a solvent
- Step B From the conductive fiber-coated particle dispersion obtained through Step A A step of obtaining conductive fiber-coated particles as a solid by removing the solvent (for example, distillation by heating and / or filtration under reduced pressure).
- the curable composition of the present invention is prepared by previously mixing conductive fiber-coated particles (component (D) (or dispersion of conductive fiber-coated particles), a curable compound, and all other components as necessary.
- conductive fiber-coated particles component (D) (or dispersion of conductive fiber-coated particles)
- a curable compound e.g., a curable compound
- All other components e.g., a curable compound
- Well one-pack type
- conductive fiber coated particles (component (D) or dispersion of conductive fiber coated particles
- curable compound e.g., a curable compound
- Multi-component type for example, two-component type
- the curable composition for sealing an optical semiconductor of the present invention discharges the curable composition with a dispenser such as a dispenser, the conductive fiber-coated particles (component (D)) in the curable composition are increased. It is preferable to discharge in a dispersed state, for example, using a discharger having a rotational drive mechanism such as a screw, and discharging while stirring by a screw-type discharge method that discharges the curable composition by rotating the screw. It is preferable.
- the rotational speed of the screw, the size of the blade of the screw, and the like are preferably adjusted as appropriate according to the viscosity of the curable composition, the size of the conductive fiber-coated particles (component (D)) contained therein, and the like.
- the curable composition of the present invention preferably has fluidity at room temperature (25 ° C.) from the viewpoint of dispensing properties in the process of sealing the optical semiconductor element.
- the viscosity of the curable composition of the present invention at normal temperature (25 ° C.) is preferably 10 to 5000 mPa ⁇ s, more preferably 50 to 3000 mPa ⁇ s, and further preferably 100 to 2000 mPa ⁇ s. preferable.
- the cured product of the present invention can be obtained by curing the curable composition for sealing an optical semiconductor.
- a curable composition containing a compound that is a raw material of the curable resin as the curable compound a cured product is obtained by heating and / or irradiating active energy rays to the curable composition.
- the temperature when cured by heating is, for example, about 45 to 200 ° C., preferably 70 to 190 ° C., particularly preferably 90 to 180 ° C.
- the heating time (curing time) for curing by heating is, for example, about 10 to 600 minutes, preferably 30 to 540 minutes, particularly preferably 60 to 480 minutes. If the curing temperature and the curing time are below the above ranges, curing may be insufficient. On the other hand, when the curing temperature and the curing time exceed the above ranges, the cured product may be decomposed.
- the curing conditions depend on various conditions, for example, when the curing temperature is increased, the curing time can be shortened, and when the curing temperature is decreased, the curing time can be appropriately increased.
- irradiation conditions when curing by irradiation with active energy rays for example, when curing by ultraviolet irradiation, a condition where the integrated light quantity is, for example, about 500 to 5000 mJ / cm 2 , particularly preferably 1000 to 3000 mJ / cm 2 is adopted. Is preferred.
- the cured product of the present invention is not particularly limited, it is preferable that water vapor permeability of not more than 40g / m 2 ⁇ day, 30g / m or less, more preferably 2 ⁇ day, more preferably less 25g / m 2 ⁇ day .
- the water vapor transmission rate can be measured by attaching a cured product to a moisture permeable cup under the conditions of 60 ° C. and 90% RH in accordance with JIS L1099.
- the cured product of the present invention is not particularly limited, but the outgas is preferably 20 ppm or less, more preferably 15 ppm or less, and even more preferably 10 ppm or less. Further, acrolein is preferably 3 ppm or less, more preferably 2 ppm or less, and further preferably 1 ppm or less. Outgas and acrolein can be measured by quantifying the amount of outgas generated when heated in an oven at 80 ° C. for 60 minutes using a gas chromatography mass spectrometry (GC / MS) apparatus using toluene as a standard substance. .
- GC / MS gas chromatography mass spectrometry
- the cured product of the present invention is preferably transparent, and when the thickness of the cured product is adjusted to 10 ⁇ m, the total light transmittance (cured product thickness: 10 ⁇ m) in the visible light wavelength region is, for example, 80% or more, preferably Is 85% or more, more preferably 90% or more.
- the total light transmittance in the visible light wavelength region of the cured product of the present invention can be measured according to JIS K7361-1.
- the cured product of the present invention is excellent in conductivity, and its volume resistivity is, for example, about 0.1 ⁇ ⁇ cm to 10 M ⁇ ⁇ cm, preferably 0.1 ⁇ ⁇ cm to 1 M ⁇ ⁇ cm.
- the volume resistivity of the cured product of the present invention can be measured in accordance with JIS K6911.
- optical semiconductor device By sealing an optical semiconductor element using the curable composition of the present invention, an optical semiconductor device having excellent performance stability and a long lifetime can be obtained.
- an optical semiconductor device For example, a light emitting diode, organic electroluminescence (organic EL), electronic paper, a solar cell, etc. are mentioned. Among these, organic electroluminescence (organic EL) is preferable, and top emission type organic electroluminescence (organic EL) is more preferable.
- the component (A) has one or more functional groups selected from the group consisting of an epoxy group, an oxetanyl group, a vinyl ether group, and a (meth) acryloyl group, and It is a compound having an aromatic ring
- the component (B) is an alicyclic epoxy compound (excluding compounds containing an aromatic ring)
- the component (C) has a cation component having an aromatic ring, and is a central element Is a curing catalyst that generates an acid by light or heat having an anionic component of boron or phosphorus
- a component (D) a particulate material and a fibrous conductive material that covers the particulate material. It is preferable that the conductive fiber-coated particles are included.
- the component (A) preferably contains the following compound (A1 ′′) and / or compound (A2 ′′).
- Compound (A1 ′′) A compound having a functional group selected from the group consisting of two or more epoxy groups, oxetanyl groups, vinyl ether groups and (meth) acryloyl groups in the molecule, and having a molecular weight of 100 to 10,000
- Compound (A2 ′′) Compound having a molecular weight of 100 to 1000
- the component (B) is a compound having two or more alicyclic epoxy groups, and the molecular weight is preferably 100 to 500. And it is preferable that a component (B) is a compound represented by the said Formula (3). Moreover, it is preferable that the cation component which has an aromatic ring of a component (C) is an aromatic sulfonium salt.
- the fibrous conductive substance of component (D) is preferably a conductive nanowire.
- the conductive nanowire is preferably at least one selected from the group consisting of metal nanowires, semiconductor nanowires, carbon fibers, carbon nanotubes, and conductive polymer nanowires.
- the metal nanowire is preferably a silver nanowire.
- the cured product of the present invention is preferably a cured product obtained by curing the curable composition for sealing an optical semiconductor.
- the cured product preferably has a water vapor transmission rate of 40 g / m 2 ⁇ day or less, preferably has an outgas of 20 ppm or less, preferably has an outgas of 20 ppm or less, and has an acrolein of 3 ppm or less. preferable.
- Silver nanowires are manufactured according to the method described in “Materials Chemistry and Physics, vol, 114, p333-338,“ Preparation of Aganorods with high yield by poly process ””. The specific procedure is shown below. 0.5 mL of an ethylene glycol solution (6 ⁇ 10 ⁇ 4 M) of FeCl 3 was added to a flask containing 6 mL of ethylene glycol and heated to 150 ° C. Thereafter, 6 mL of an ethylene glycol mixed solution containing 0.052 M AgNO 3 and 0.067 M polyvinylpyrrolidone was added dropwise to the heated solution. The reaction solution thus obtained was kept at 150 ° C. for 1.5 hours.
- a dispersion was obtained.
- a part of the obtained dispersion was extracted and dried by heat to confirm the weight% of the silver nanowires in the dispersion, which was 2.9% by weight.
- the average diameter (average thickness) and average length of the obtained silver nanowires are measured using a scanning electron microscope (SEM) to measure the diameter (thickness) and length of 100 silver nanowires, and each is arithmetically averaged. As a result, the average diameter was 115 nm and the length was 20 to 50 ⁇ m.
- plastic fine particles fine particles made of methyl methacrylate-styrene copolymer (trade name “SM10X-8JH”, manufactured by Sekisui Chemical Co., Ltd., refractive index: 1.565, average particle size: 8.3 ⁇ m, CV value: 39, 10% compressive strength: 2.4 to 2.5 kgf / mm 2 ) is mixed with 100 parts by weight of the curable compound, 0.85 parts by weight of ethanol is mixed with 29.15 parts by weight, and dispersed. A dispersion was prepared.
- SM10X-8JH methyl methacrylate-styrene copolymer
- the solvent was removed by stirring while heating at 70 ° C. for 30 minutes to obtain conductive fiber-coated particles (component (D)).
- the surface area per one the plastic particulate is 226.9Myuemu 2
- the projected area per one silver nanowires was 2.4 [mu] m 2.
- the content [ppm] of acrolein and 1-iodo-4-methylbenzene contained in the outgas is also determined by quantifying the amounts of acrolein and 1-iodo-4-methylbenzene, respectively, using toluene as a standard substance. Asked.
- the evaluation criteria for the obtained heat generation temperature and heat generation amount are as follows. A: No exothermic peak is observed at 250 ° C. or higher (curability is particularly good) B: An exothermic peak of 10 J / g or less is observed at 250 ° C. or higher (good curability) C: An exothermic peak of 10 J / g or more is observed at 250 ° C. or more (poor curability)
- the cured product of the present invention is a cation having an alicyclic epoxy compound as component (B) and an aromatic ring as component (C). It has been found that outgassing can be significantly suppressed by including a curing catalyst having a component and an anionic component whose central element is boron or phosphorus.
- the curable composition of the present invention can be used for applications such as sealing materials and sealing materials for optical semiconductor elements such as LED elements and organic EL elements.
- the optical semiconductor element sealed or sealed with the curable composition of the present invention and the optical semiconductor device using the optical semiconductor element can be used for applications such as light emitting diodes, organic electroluminescence, electronic paper, or solar cells. it can.
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Abstract
Description
[1] 下記成分(A)、(B)、及び(C)を含む光半導体封止用硬化性組成物。
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):3以上の芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒
[2] 下記成分(A)、(B)、(C)、及び(D)を含む光半導体封止用硬化性組成物。
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒
成分(D):粒子状物質と該粒子状物質を被覆する繊維状の導電性物質を含む導電性繊維被覆粒子
[3] 成分(A)が、芳香環を有し、且つ、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる2以上の官能基を有する化合物(A1’)を含む上記[1]又は[2]に記載の半導体封止用硬化性組成物。
[4] 化合物(A1’)の分子量が100~10000である上記[3]に記載の半導体封止用硬化性組成物。
[5] 成分(A)が、芳香環を有し、且つ、分子量が100~1000であり、且つ、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1の官能基を有する化合物(A2’)を含む上記[1]~[4]のいずれかに記載の光半導体封止用硬化性組成物。
[6] 成分(B)が、2以上の脂環エポキシ基を有する化合物である上記[1]~[5]のいずれかに記載の光半導体封止用硬化性組成物。
[7] 成分(B)の分子量が100~500である上記[1]~[6]のいずれかに記載の光半導体封止用硬化性組成物。
[8] 成分(B)が、エステル基及び/又はカーボネート基を有さない化合物である上記[1]~[7]のいずれかに記載の光半導体封止用硬化性組成物。
[9] 成分(A)が、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有し、且つ芳香環を有する化合物であり、成分(B)が、脂環エポキシ化合物(芳香環を含む化合物を除く)である上記[1]~[8]のいずれかに記載の光半導体封止用硬化性組成物。
[10] 成分(B)が、下記式(3)で表される化合物である上記[1]~[9]のいずれかに記載の光半導体封止用硬化性組成物。
[11] 成分(B)の含有量が硬化性組成物の全量(100重量%)に対して30~95重量%であり、且つ、成分(C)の含有量が硬化性組成物の全量(100重量%)に対して0.01~8重量%である上記[1]~[10]のいずれかに記載の光半導体封止用硬化性組成物。
[12] 成分(C)の芳香環を有するカチオン成分が、芳香族スルホニウム塩である上記[1]~[11]のいずれかに記載の光半導体封止用硬化性組成物。
[13] 成分(D)の繊維状の導電性物質が、導電性ナノワイヤである上記[2]~[12]のいずれかに記載の光半導体封止用硬化性組成物。
[14] 前記導電性ナノワイヤが、金属ナノワイヤ、半導体ナノワイヤ、炭素繊維、カーボンナノチューブ、及び導電性高分子ナノワイヤからなる群より選択される少なくとも一種である上記[13]に記載の光半導体封止用硬化性組成物。
[15] 前記金属ナノワイヤが銀ナノワイヤである上記[14]に記載の光半導体封止用硬化性組成物。
[16] 上記[1]~[15]のいずれかに記載の光半導体封止用硬化性組成物を硬化させることにより得られる硬化物。
[17] 水蒸気透過率が40g/m2・day以下である上記[16]記載の硬化物。
[18] アウトガスが20ppm以下である上記[16]又は[17]に記載の硬化物。
[19] アクロレインが3ppm以下である上記[16]~[18]のいずれかに記載の硬化物。
[20] 上記[1]~[15]のいずれかに記載の光半導体封止用硬化性組成物を用いて封止又はシールされた光半導体。
[21] 上記[20]に記載の光半導体を用いた光半導体装置。
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):3以上の芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒
成分(D):粒子状物質と該粒子状物質を被覆する繊維状の導電性物質を含む導電性繊維被覆粒子
成分(A)は、エポキシ基、オキセタン基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物であれば特に限定されない。成分(A)の化合物が有する官能基の数は特に限定されないが、WO2012/020688号公報(特許文献4)に記載の通り、一般に、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる2以上の官能基を有する化合物(以下、「化合物(A1)」という場合がある。)が用いられることが好ましい。また、低透過性及び高ガスバリア性の観点からは、分子量が100~1000であり、且つ、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1の官能基を有する化合物(以下、「化合物(A2)」という場合がある。)を上記化合物(A1)とともに配合することがより好ましい。なお、1分子中に2つ以上のエポキシ基、オキセタン基、ビニルエーテル基及び(メタ)アクリロイル基を有する場合、2つ以上の基は、それぞれ同一であっても異なっていてもよい。
化合物(A1)は、エポキシ基、オキセタニル基、ビニルエーテル基(以上、カチオン重合性官能基)、及び(メタ)アクリロイル基(ラジカル重合性官能基)からなる群より選ばれる2以上の官能基を有する化合物である。中でも官能基としては、エポキシ基が好ましい(特に好ましくはグリシジル基)。化合物(A1)1分子中の官能基の数は、例えば2~30個であり、好ましくは2~10個、より好ましくは2~6個、さらに好ましくは2~3個である。複数個の官能基は、それぞれ同一であっても異なっていても良い。化合物(A1)の分子量は、特に制限されないが、100~10000が好ましく、より好ましくは150~5000、さらに好ましくは200~1000である。なお、化合物(A1)は、1種を単独で、又は2種以上を組み合わせて使用することができる。
化合物(A2)は、1分子中に1つのエポキシ基、オキセタン基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1つの官能基を有し、さらに分子量が100~1000である化合物である。化合物(A2)の分子量が100~1000であると、硬化性組成物が硬化した場合に、生成する重合物の側鎖として、硬化物における自由体積をパッキングすることにより、低透湿性及び高ガスバリア性に寄与する効果が得られる。化合物(A2)における環状骨格としては、上記化合物(A1)で例示のものが挙げられる。中でも、ベンゼン環、シクロヘキサン環が好ましい。なお、化合物(A2)は、1種を単独で、又は2種以上を組合せて使用することができる。
で表される化合物が挙げられる。上記Z2は環状骨格を有する基であることが好ましい。環状骨格としては、前記例示のものが挙げられる。
成分(B)は、脂環エポキシ化合物、即ち、分子内(一分子中)に脂環(脂肪族炭化水素環)構造とエポキシ基とを少なくとも有する化合物である。本発明の硬化性組成物において、成分(B)は、1種を単独で、又は2種以上を組合せて使用することができる。
本発明における成分(C)は、芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒であってもよく、3以上の芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒であってもよい。
光カチオン重合開始剤は、光の照射によってカチオン種を発生してカチオン硬化性化合物の硬化反応を開始させる光カチオン重合開始剤である。光カチオン重合開始剤は、光を吸収するカチオン部と酸の発生源となるアニオン部からなる。なお、光カチオン重合開始剤は、1種を単独で、又は2種以上を組合せて使用することができる。
熱カチオン重合開始剤としては、例えば、ジアゾニウム塩系化合物、ヨードニウム塩系化合物、スルホニウム塩系化合物、ホスホニウム塩系化合物、セレニウム塩系化合物、オキソニウム塩系化合物、アンモニウム塩系化合物、臭素塩系化合物等が挙げられる。なお、熱カチオン重合開始剤は、1種を単独で、又は2種以上を組合せて使用することができる。
本発明の硬化性組成物は、硬化速度を促進する硬化促進剤を含んでもよい。硬化促進剤としては、周知慣用の硬化促進剤を使用することができ、例えば、1,8−ジアザビシクロ[5.4.0]ウンデセン−7(DBU)、及びその塩(例えば、フェノール塩、オクチル酸塩、p−トルエンスルホン酸塩、テトラフェニルボレート塩);1,5−ジアザビシクロ[4.3.0]ノネン−5(DBN)、及びその塩(例えば、ホスホニウム塩、スルホニウム塩、4級アンモニウム塩、ヨードニウム塩);ベンジルジメチルアミン、2,4,6−トリス(ジメチルアミノメチル)フェノール、N,N−ジメチルシクロヘキシルアミン等の3級アミン;2−エチル−4−メチルイミダゾール、1−シアノエチル−2−エチル−4−メチルイミダゾール等のイミダゾール;リン酸エステル、トリフェニルホスフィン等のホスフィン類;テトラフェニルホスホニウムテトラ(p−トリル)ボレート等のホスホニウム化合物;オクチル酸スズ、オクチル酸亜鉛等の有機金属塩;金属キレート等が挙げられる。これらは1種を単独で、又は2種以上を組合せて使用することができる。
本発明の硬化性組成物は、光ラジカル重合開始剤を含んでもよい。光ラジカル重合開始剤としては、例えば、ベンゾフェノン、アセトフェノンベンジル、ジベンジルメチルケトン、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ジメトキシアセトフェノン、ジメトキシフェニルアセトフェノン、ジエトキシアセトフェノン、ジフェイニルジサルファイト、オルトベンゾイル安息香酸メチル、4−ジメチルアミノ安息香酸エチル(日本化薬(株)製、商品名「カヤキュアEPA」等)、2,4−ジエチルチオキサンソン(日本化薬(株)製、商品名「カヤキュアDETX」等)、2−メチル−1−[4−(メチル)フェニル]−2−モルホリノプロパノン−1(チバガイギー(株)製、商品名「イルガキュア907」等)、2−ジメチルアミノ−2−(4−モルホリノ)ベンゾイル−1−フェイニルプロパン等の2−アミノ−2−ベンゾイル−1−フェニルアルカノン化合物、テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン、ベンジル、2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン、4,4−ビスジエチルアミノベンゾフェノン等のアミノベンゼン誘導体、2,2’−ビス(2−クロロフェニル)−4,5,4’,5’−テトラフェニル−1,2’−ビイミダゾール(保土谷化学(株)製、商品名「B−CIM」等)等のイミダゾール化合物、2,6−ビス(トリクロロメチル)−4−(4−メトキシナフタレン−1−イル)−1,3,5−トリアジン等のハロメチル化トリアジン化合物、2−トリクロロメチル−5−(2−ベンゾフラン2−イル−エテニル)−1,3,4−オキサジアゾール等のハロメチルオキサジアゾール化合物等が挙げられる。これらの光ラジカル重合開始剤は1種を単独で、又は2種以上を組合せて使用することができる。また、必要に応じて光増感剤を加えることができる。光ラジカル重合開始剤としては、感度及び耐薬品性等の観点から、イミダゾール化合物とアミノベンゼン誘導体の組合せ、2−アミノ−2−ベンゾイル−1−フェニルアルカン化合物、ハロメチル化トリアジン化合物、ハロメチルオキサジアゾール化合物等が好ましい。
本発明の硬化性組成物は、熱ラジカル重合開始剤を含んでいてもよい。熱ラジカル重合開始剤としては、例えば、有機過酸化物類が挙げられる。有機過酸化物類としては、ジアルキルパーオキサイド、アシルパーオキサイド、ハイドロパーオキサイド、ケトンパーオキサイド、パーオキシエステル等を使用することができる。有機過酸化物類の具体例としては、ベンゾイルパーオキサイド、t−ブチルパーオキシ−2−エチルヘキサネート、2,5−ジメチル−2,5−ジ(2−エチルヘキサノイル)パーオキシヘキサン、t−ブチルパーオキシベンゾエート、t−ブチルパーオキサイド、クメンハイドロパーオキサイド、ジクミルパーオキサイド、ジ−t−ブチルパーオキサイド、2,5−ジメチル−2,5−ジブチルパーオキシヘキサン、2,4−ジクロロベンゾイルパーオキサイド、ジ−t−ブチルパーオキサイドジ−イソプロピルベンゼン、1,1−ビス(t−ブチルパーオキシ)−3,3,5−トリメチルシクロヘキサン、メチルエチルケトンパーオキシド、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート等が挙げられる。さらに、上記熱ラジカル重合開始剤とともに、ナフテン酸コバルト、ナフテン酸マンガン、ナフテン酸亜鉛、オクテン酸コバルト等のナフテン酸やオクテン酸のコバルト、マンガン、鉛、亜鉛、バナジウム等の金属塩を併用することができる。同様に、ジメチルアニリン等の3級アミンも使用することができる。
本発明の硬化性組成物は、重合開始剤として光カチオン重合開始剤を含有する場合は、硬化遅延剤を含有してもよい。硬化遅延剤としては、例えば、ピロール、ピラゾール、3,5−ジメチルピラゾール、イミダゾール、1,2,3−トリアゾール、1,2,4−トリアゾール等のアゾール系化合物;エチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、ブチレングリコール等の(ポリ)アルキレングリコール、グリセリン、ポリグリセリン、ペンタエリスリトール、ポリカプロラクトンポリオール、クラウンエーテル等のポリオール化合物(特に、脂肪族ポリオール化合物)等が挙げられる。これらは1種を単独で、又は2種以上を組み合わせて使用することができる。前記硬化遅延剤を添加することで、本発明の硬化性組成物に光を照射した後の可使時間及び硬化開始時間を制御することができる。より詳細には、前記硬化遅延剤は、UV照射することにより光カチオン重合開始剤から発生するカチオンをトラップして硬化性化合物のカチオン重合を抑制することができ、加熱処理を施すとカチオンを放出して硬化性化合物のカチオン重合を進行させる作用を有する。前記硬化遅延剤の中でもアゾール系化合物は、アウトガス発生の原因とはならない点で好ましく、硬化性組成物に添加することにより硬化性組成物の可使時間を自由にコントロールすることができ、硬化性組成物の塗膜にUVを照射し、その後有機EL素子に貼り合わせて加熱処理を施すことにより、有機EL素子をUVに直に曝すことなく封止することができ、低アウトガス性及び防湿性を有する硬化物で有機EL素子を封止することができる。
本発明における成分(D)は、粒子状物質と、該粒子状物質を被覆する繊維状の導電性物質(「導電性繊維」と称する場合がある)とを含む導電性繊維被覆粒子である。なお、本発明の導電性繊維被覆粒子において「被覆する」とは、導電性繊維が粒子状物質の表面の一部又は全部を覆った状態を意味する。本発明の導電性繊維被覆粒子においては、導電性繊維が粒子状物質の表面の少なくとも一部を被覆していればよく、例えば、被覆された部分よりも被覆されていない部分の方が多く存在していてもよい。なお、本発明の導電性繊維被覆粒子においては、必ずしも粒子状物質と導電性繊維とが接触している必要はないが、通常、導電性繊維の一部は粒子状物質の表面に接触している。
本発明の導電性繊維被覆粒子を構成する粒子状物質は、粒子状の構造体である。
|導電性繊維被覆粒子を構成する粒子状物質の屈折率(25℃、波長589.3nmにおける)−硬化性化合物の硬化物の屈折率(25℃、波長589.3nmにおける)|≦0.1
なお、粒子状物質の体積基準の粒度分布における変動係数は、以下の式より算出される。また、粒度分布は粒度分布測定装置(商品名「Coulter Multisizer」、ベックマン・コールター社製)等を使用して測定することができる。
変動係数(CV値)(%)=(S2/Dn)×100
(式中、S2は、体積基準の粒度分布における標準偏差を示し、Dnは、体積基準におけるメディアン径(D50)を示す)
本発明の導電性繊維被覆粒子を構成する導電性繊維は、導電性を有する繊維状の構造体(線状構造体)である。上記導電性繊維の形状は繊維状(ファイバー状)であればよく、特に限定されないが、その平均アスペクト比は、10以上(例えば、20~5000)が好ましく、50~3000がより好ましく、100~1000がさらに好ましい。平均アスペクト比が上記範囲を下回ると、少量の導電性繊維被覆粒子の配合によって優れた導電性を発現させることが困難となる場合がある。上記導電性繊維の平均アスペクト比は、粒子状物質の平均アスペクト比と同様の手順で測定できる。なお、上記導電性繊維における「繊維状」の概念には、「ワイヤー状」、「ロッド状」等の各種の線状構造体の形状も含まれる。また、本明細書においては、平均太さが1000nm以下の繊維を「ナノワイヤ」と称する場合がある。
長さ=投影面積/投影径
(1)上記粒子状物質を溶媒に分散させた分散液(「粒子分散液」と称する)と、上記導電性繊維を溶媒に分散させた分散液(「繊維分散液」と称する)とを混合し、必要に応じて溶媒を除去して、本発明の導電性繊維被覆粒子(又は該導電性繊維被覆粒子の分散液)を得る。
(2)上記粒子分散液に上記導電性繊維を配合し、混合した後、必要に応じて溶媒を除去して、本発明の導電性繊維被覆粒子(又は該導電性繊維被覆粒子の分散液)を得る。
(3)上記繊維分散液に上記粒子状物質を配合し、混合した後、必要に応じて溶媒を除去して、本発明の導電性繊維被覆粒子(又は該導電性繊維被覆粒子の分散液)を得る。
(4)溶媒に上記粒子状物質及び上記導電性繊維を配合し、混合した後、必要に応じて溶媒を除去して、本発明の導電性繊維被覆粒子(又は該導電性繊維被覆粒子の分散液)を得る。
本発明においては、中でも、均質な導電性繊維被覆粒子が得られる点で、上記(1)の方法が好ましい。
本発明の硬化性組成物は、上記以外にも、本発明の効果を損なわない範囲内で各種添加剤を含有していてもよい。上記添加剤としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、グリセリン等の水酸基を有する化合物;シリコーン系やフッ素系消泡剤;レベリング剤;γ−グリシドキシプロピルトリメトキシシラン、3−メルカプトプロピルトリメトキシシラン等のシランカップリング剤;界面活性剤;シリカ、アルミナ等の無機充填剤;難燃剤;着色剤;酸化防止剤;紫外線吸収剤;イオン吸着体;顔料;蛍光体;離型剤等の慣用の添加剤が挙げられる。
本発明の硬化性組成物は、上記各成分を均一に混合することにより得られる。本発明の硬化性組成物を得るには、各成分を自公転式撹拌脱泡装置、ホモジナイザー、プラネタリー、3本ロールミル、ビーズミル、超音波等の一般的に知られている混合用機器を使用してなるべく均一になるように、撹拌、溶解、混合、分散等を行うことが望ましい。
(1)粒子状物質と繊維状の導電性物質とを溶媒中で混合して得られる導電性繊維被覆粒子の分散液と、硬化性化合物と必要に応じてその他の添加剤とを、所定の割合で撹拌及び混合し、次いで、溶媒を留去することにより製造する方法や、
(2)下記工程A及び工程Bを経て得られた導電性繊維被覆粒子と硬化性化合物と必要に応じてその他の添加剤とを、所定の割合で撹拌及び混合することにより製造する方法等が挙げられる。
工程A:粒子状物質と繊維状の導電性物質とを溶媒中で混合することにより導電性繊維被覆粒子分散液を得る工程
工程B:工程Aを経て得られた導電性繊維被覆粒子分散液から溶媒を除去(例えば、加熱により留去及び/又は減圧濾過等)することにより導電性繊維被覆粒子を固体として得る工程
本発明の硬化物は、上記光半導体封止用硬化性組成物を硬化させることにより得られる。硬化性化合物として硬化性樹脂の原料となる化合物を含む硬化性組成物の場合は、該硬化性組成物を加熱及び/又は活性エネルギー線照射にすることにより硬化物が得られる。
本発明の硬化性組成物を用いて、光半導体素子を封止することにより、性能の安定性に優れ、寿命の長い光半導体装置を得ることができる。光半導体装置としては、特に限定されないが、例えば、発光ダイオード、有機エレクトロルミネッセンス(有機EL)、電子ペーパー、又は太陽電池等が挙げられる。その中でも、有機エレクトロルミネッセンス(有機EL)が好ましく、トップエミッション型有機エレクトロルミネッセンス(有機EL)がより好ましい。
本発明の光半導体封止用硬化性組成物は、成分(A)が、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有し、且つ芳香環を有する化合物であり、成分(B)が、脂環エポキシ化合物(芳香環を含む化合物を除く)であり、成分(C)が、芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒であり、さらに成分(D)として、粒子状物質と該粒子状物質を被覆する繊維状の導電性物質を含む導電性繊維被覆粒子を含むことが好ましい。この成分(D)を含むことにより、導電性(特に、厚み方向への導電性)に優れる光半導体素子封止用硬化性組成物及びその硬化物を得ることができる。
化合物(A1’’):1分子中に2つ以上のエポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる官能基を有し、さらに分子量が100~10000である化合物
化合物(A2’’):分子量が100~1000である化合物
[銀ナノワイヤの製造]
銀ナノワイヤを、「Materials Chemistry and Physics,vol,114,p333−338,”Preparation of Ag nanorods with high yield by polyol process”」に記載された方法に準じて製造した。具体的な手順を以下に示す。
FeCl3のエチレングリコール溶液(6×10−4M)0.5mLを、エチレングリコール6mLを入れたフラスコ内に加え、150℃に加熱した。その後、0.052MのAgNO3及び0.067Mのポリビニルピロリドンを含むエチレングリコール混合溶液6mLを、上記加熱溶液に滴下した。このようにして得られた反応溶液を150℃で1.5時間保持した。その後、得られた懸濁液10mLを800mLのエタノールとアセトンの混合溶媒(エタノール:アセトン=1:1(重量比))で希釈し、遠心分離(2000rpm、10分間)を2回行い、銀ナノワイヤの分散液を得た。得られた分散液を一部抜き取り、熱乾燥させて分散液中の銀ナノワイヤの重量%を確認したところ、2.9重量%であった。
得られた銀ナノワイヤの平均直径(平均太さ)及び平均長さを走査型電子顕微鏡(SEM)を用いて100個の銀ナノワイヤの直径(太さ)及び長さを計測し、それぞれ算術平均することにより測定したところ、平均直径は115nmであり、長さは20~50μmであった。
プラスチック微粒子として、メタクリル酸メチル−スチレン共重合体からなる微粒子(商品名「SM10X−8JH」、積水化学工業(株)製、屈折率:1.565、平均粒子径:8.3μm、CV値:39、10%圧縮強度:2.4~2.5kgf/mm2)を硬化性化合物100重量部に対して、0.85重量部をエタノール29.15重量部に混合し、分散させ、プラスチック微粒子の分散液を調製した。そして、上記プラスチック微粒子の分散液と、上記銀ナノワイヤの製造で得られた銀ナノワイヤの分散液を5.22重量部(硬化性化合物100重量部に対して、銀ナノワイヤ0.15重量部を含む)とを混合し、その後、70℃で30分間加熱しながら撹拌することによって溶媒を除去して、導電性繊維被覆粒子(成分(D))を得た。
なお、上記プラスチック微粒子1個あたりの表面積は226.9μm2であり、銀ナノワイヤの1本当たりの投影面積は2.4μm2であった。上記で仕込んだプラスチック微粒子(0.85重量部)と銀ナノワイヤ(0.15重量部)から、プラスチック微粒子1個に対して20本の銀ナノワイヤが吸着していると考えられ、これよりプラスチック微粒子の表面積(総表面積)/銀ナノワイヤの投影面積(総投影面積)を算出すると、約100/15となった。
実施例及び比較例において、各化合物を表1及び表2に示した配合割合(単位:重量部)にて混合した後、室温にて撹拌し、各硬化性組成物を調製した。なお、化合物(A1)及び化合物(A2)は、成分(A)であり、化合物(B)は、成分(B)であり、化合物(C)−1、化合物(C)−2、化合物(C)−3及び化合物(C)−4は、成分(C)である。
上記にて得られた各硬化性組成物を約60mg計量し、ベルトコンベアーUV照射装置(商品名「UVC−02516S1AA02」、ウシオ電機株式会社製)にて2500mJ/cm2の紫外線を照射した後、ガスクロマトグラフィー質量分析(GC/MS)装置(商品名「HP6890GC/5973MSD」、アジレント・テクノロジー株式会社)を用いて、80℃のオーブン(商品名「DRM320DB」、ADVANTEC社製)にて60分加熱した際に発生するアウトガスの量を、トルエンを標準物質として定量することにより、各硬化性組成物におけるアウトガス含有量[ppm]を求めた。また、アウトガス中に含まれるアクロレイン及び1−ヨード−4−メチルベンゼンの含有量[ppm]も、アクロレイン及び1−ヨード−4−メチルベンゼン、それぞれの量を、トルエンを標準物質として定量することにより求めた。
上記にて得られた各硬化性組成物を5mg計量し、ベルトコンベアーUV照射装置(商品名「UVC−02516S1AA02」、ウシオ電機株式会社製)にて2500mJ/cm2の紫外線を照射した後、示差走査熱量分析(DSC)装置(商品名「DSC−Q2000」、ティー・エイ・インスツルメント社製)を用いて、各硬化性組成物の硬化反応における発熱温度及び発熱量を確認した。なお、紫外線の照射完了からDSC装置による測定開始までの時間は12分間とした。
A:250℃以上に発熱ピークが認められない(硬化性が特に良い)
B:250℃以上に10J/g以下の発熱ピークが認められる(硬化性が良い)
C:250℃以上に10J/g以上の発熱ピークが認められる(硬化性が悪い)
上記にて得られた各硬化性組成物を試験管(試験管サイズ:管径1cm×高さ2.5cm)に2mL採取し、25℃、1気圧の環境下において静置し、含有する粒子が完全に沈降するまでの時間を測定して分散性を評価した。なお、粒子が完全に沈降した時点(終点)は、目視で透明な硬化性組成物を確認することによって判断できる。
上記にて得られた各硬化性組成物を硬化後の厚みが100μmとなるようにPETフィルムに塗布し、ベルトコンベアーUV照射装置(商品名「UVC−02516S1AA02」、ウシオ電機株式会社製)にて2500mJ/cm2の紫外線を照射した後、得られた硬化物を透湿カップに取り付け、JIS L1099に従って、60℃、90%RHの条件にて、上記硬化物の水蒸気透過率を測定した。
上記にて得られた各硬化性組成物を2枚の導電性ガラス基板(Luminescence Technology社製、サイズ:25mm×25mm、ITO厚み:0.14μm)の間に硬化後の厚みが10μmとなるように挟み、窒素雰囲気下、100℃で1時間熱処理を行い、得られた硬化物を25℃、1気圧環境下において、エレクトロンメーター(ピー・エス・エス社製)を用いて、電気抵抗率(Ω・cm)と電圧(V)を測定し、導電性を評価した。
化合物(A1): ビスフェノールFジグリシジルエーテル(商品名「YL−983U」、三菱化学(株)製)
化合物(A2): o−フェニルフェノールグリシジルエーテル(商品名「SY−OYG」、阪本薬品工業(株)製)
化合物(B): (3,4,3’,4’−ジエポキシ)ビシクロヘキシル
化合物(C)−1: 4−(4−ビフェニルチオ)フェニル−4−ビフェニルフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート
化合物(C)−2: ジフェニル[4−(フェニルチオ)フェニル]スルホニウム テトラキス(ペンタフルオロフェニル)ボレート
化合物(C)−3: ジフェニル[4−(フェニルチオ)フェニル]スルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェート(商品名「CPI−210S」、サンアプロ(株)製)
化合物(C)−4: ジフェニル[4−(フェニルチオ)フェニル]スルホニウム ヘキサフルオロホスフェート(商品名「CPI−110P」、サンアプロ(株)製)
PI‐2074: ペンタフルオロフェニルボレート トルイルクミルヨードニウム塩(商品名「PI‐2074」、ローディア社製)
ミクロパールAU:ジビニルベンゼンを主成分とする架橋重合体からなる粒子状物質の表面が金メッキされたもの、商品名「ミクロパールAU−2085」、積水化学工業(株)製、平均粒子径8.5μm
Claims (21)
- 下記成分(A)、(B)、及び(C)を含む光半導体封止用硬化性組成物。
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):3以上の芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒 - 下記成分(A)、(B)、(C)、及び(D)を含む光半導体封止用硬化性組成物。
成分(A):エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有する化合物
成分(B):脂環エポキシ化合物
成分(C):芳香環を有するカチオン成分を有し、且つ、中心元素がホウ素又はリンであるアニオン成分を有する光又は熱により酸を発生する硬化触媒
成分(D):粒子状物質と該粒子状物質を被覆する繊維状の導電性物質を含む導電性繊維被覆粒子 - 成分(A)が、芳香環を有し、且つ、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる2以上の官能基を有する化合物(A1’)を含む請求項1又は2に記載の半導体封止用硬化性組成物。
- 化合物(A1’)の分子量が100~10000である請求項3に記載の半導体封止用硬化性組成物。
- 成分(A)が、芳香環を有し、且つ、分子量が100~1000であり、且つ、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1の官能基を有する化合物(A2’)を含む請求項1~4のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(B)が、2以上の脂環エポキシ基を有する化合物である請求項1~5のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(B)の分子量が100~500である請求項1~6のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(B)が、エステル基及び/又はカーボネート基を有さない化合物である請求項1~7のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(A)が、エポキシ基、オキセタニル基、ビニルエーテル基及び(メタ)アクリロイル基からなる群より選ばれる1以上の官能基を有し、且つ芳香環を有する化合物であり、成分(B)が、脂環エポキシ化合物(芳香環を含む化合物を除く)である請求項1~8のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(B)の含有量が硬化性組成物の全量(100重量%)に対して30~95重量%であり、且つ、成分(C)の含有量が硬化性組成物の全量(100重量%)に対して0.01~8重量%である請求項1~10のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(C)の芳香環を有するカチオン成分が、芳香族スルホニウム塩である請求項1~11のいずれか1項に記載の光半導体封止用硬化性組成物。
- 成分(D)の繊維状の導電性物質が、導電性ナノワイヤである請求項2~12のいずれか1項に記載の光半導体封止用硬化性組成物。
- 前記導電性ナノワイヤが、金属ナノワイヤ、半導体ナノワイヤ、炭素繊維、カーボンナノチューブ、及び導電性高分子ナノワイヤからなる群より選択される少なくとも一種である請求項13に記載の光半導体封止用硬化性組成物。
- 前記金属ナノワイヤが銀ナノワイヤである請求項14に記載の光半導体封止用硬化性組成物。
- 請求項1~15のいずれか1項に記載の光半導体封止用硬化性組成物を硬化させることにより得られる硬化物。
- 水蒸気透過率が40g/m2・day以下である請求項16記載の硬化物。
- アウトガスが20ppm以下である請求項16又は17に記載の硬化物。
- アクロレインが3ppm以下である請求項16~18のいずれか1項に記載の硬化物。
- 請求項1~15のいずれか1項に記載の光半導体封止用硬化性組成物を用いて封止又はシールされた光半導体。
- 請求項20に記載の光半導体を用いた光半導体装置。
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Also Published As
Publication number | Publication date |
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EP3006481A1 (en) | 2016-04-13 |
KR20160015226A (ko) | 2016-02-12 |
US9685597B2 (en) | 2017-06-20 |
JPWO2014192839A1 (ja) | 2017-02-23 |
JP5926458B2 (ja) | 2016-05-25 |
TWI554540B (zh) | 2016-10-21 |
CN105246940B (zh) | 2018-09-04 |
TW201500396A (zh) | 2015-01-01 |
KR101763058B1 (ko) | 2017-07-28 |
US20160126431A1 (en) | 2016-05-05 |
CN105246940A (zh) | 2016-01-13 |
EP3006481A4 (en) | 2017-01-18 |
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