KR20160049539A - One-part curable silicone composition and optical semiconductor device - Google Patents
One-part curable silicone composition and optical semiconductor device Download PDFInfo
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- KR20160049539A KR20160049539A KR1020167007805A KR20167007805A KR20160049539A KR 20160049539 A KR20160049539 A KR 20160049539A KR 1020167007805 A KR1020167007805 A KR 1020167007805A KR 20167007805 A KR20167007805 A KR 20167007805A KR 20160049539 A KR20160049539 A KR 20160049539A
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- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 60
- 239000004065 semiconductor Substances 0.000 title claims description 24
- 230000003287 optical effect Effects 0.000 title claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- -1 Polysiloxane Polymers 0.000 claims description 29
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 6
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- 238000003860 storage Methods 0.000 abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 125000000962 organic group Chemical group 0.000 description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 6
- 150000003961 organosilicon compounds Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- ZXKHOVDDJMJXQP-UHFFFAOYSA-N 1-ethenylcyclohexan-1-ol Chemical compound C=CC1(O)CCCCC1 ZXKHOVDDJMJXQP-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KYTGWYJWMAKBPN-UHFFFAOYSA-N [dimethyl(prop-2-enyl)silyl]oxy-dimethyl-prop-2-enylsilane Chemical compound C=CC[Si](C)(C)O[Si](C)(C)CC=C KYTGWYJWMAKBPN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- HOMYFVKFSFMSFF-UHFFFAOYSA-N ethenyl-[ethenyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=C)O[Si](C=C)(C=1C=CC=CC=1)C1=CC=CC=C1 HOMYFVKFSFMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005417 glycidoxyalkyl group Chemical group 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RFGGTTPASBFBTB-UHFFFAOYSA-N methyl-[methyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)O[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 RFGGTTPASBFBTB-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 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
- 239000011787 zinc oxide Substances 0.000 description 1
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
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- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- H01—ELECTRIC ELEMENTS
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- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/4805—Shape
- H01L2224/4809—Loop shape
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- H01L2224/42—Wire connectors; Manufacturing methods related thereto
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- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
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- 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
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Abstract
The present invention relates to a one-pack type curable silicone composition comprising (A) a branched chain organopolysiloxane having an alkenyl group and an aryl group; And (B) component (i) at least one compound selected from the group consisting of the following general formula: HR 2 2 SiO (R 2 2 SiO) m SiR 2 2 H wherein R 2 represents the same or different monovalent hydrocarbon groups lacking an aliphatic unsaturated bond, at least 15 mol% of R 2 in one molecule is an aryl group; m is to catalyst, and (iii) the organopolysiloxane, (ii) a hydrosilylation reaction metal-expressed with from 1 to 100 integer) the general formula: R 3 2 NR 4 -NR 3 2 wherein R 3 is the same or different and represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and R 4 represents an alkylene group having 2 to 4 carbon atoms, ≪ / RTI > The one-pack type curable silicone composition has storage stability.
Description
The present invention relates to a one-part curable silicone composition which is cured by a hydrosilylation reaction, and to a photosemiconductor device manufactured using the composition.
Priority is claimed on Japanese Patent Application No. 2013-179426, filed on August 30, 2013, the content of which is incorporated herein by reference.
Since the curable silicone composition having an aryl group cured by the hydrosilylation reaction is rapidly cured by heating to form a highly transparent cured product having a high refractive index, the optical semiconductor device such as a light emitting diode (LED) As a sealant of the device and as a protective agent.
Examples of such curable silicone compositions include a curable silicone composition comprising a branched chain organopolysiloxane having phenyl and alkenyl groups, an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule, and a hydrosilylation reaction catalyst Patent Document 1); A straight chain organopolysiloxane having at least two alkenyl groups and at least one aryl group in one molecule, a branched chain organopolysiloxane having at least one alkenyl group and at least one aryl group in one molecule, at least two silicon-bonded An organopolysiloxane having a hydrogen atom bonded thereto, and a hydrosilylation reaction catalyst (see Patent Document 2); A straight chain organopolysiloxane having at least one alkenyl group in one molecule and containing diphenylsiloxane units, a branched chain organopolysiloxane having a vinyl group and a phenyl group, an organopolysiloxane having a diorganohydrogensiloxy group, and a hydrosilylation reaction catalyst (See Patent Document 3).
Such a curable silicone composition is provided with two components divided into a hydrosilylation reaction catalyst and an organopolysiloxane having silicon-bonded hydrogen atoms to ensure storage stability. For use, the two components should be homogeneously mixed. As a result, if the mixing ratio of the two components has to be changed, or if the two components are not sufficiently mixed, the original performance will not be sufficient. Therefore, there is a need for a one-pack curable silicone composition that has storage stability and does not require mixing prior to use.
It is an object of the present invention to provide a one-pack type curable silicone composition having storage stability as well as a highly reliable optical semiconductor device using the composition.
In the one-pack type curable silicone composition of the present invention,
(A) the following average unit formula:
(R 1 SiO 3/2) a (
(Wherein, R 1 has only the same or different 1 represent a hydrocarbon group, a 5 mol% is alkenyl group of R 1 in the molecule is at least 30 mol% of R 1 is an aryl group; X is a hydrogen atom or an alkyl A represents a positive integer, b represents 0 or a positive integer, c represents 0 or a positive integer, d represents a number of 0 to 0.3, e represents a number of 0 to 0.4 , b / a is a number from 0 to 10, c / a is a number from 0 to 5, and a + b + c + d = 1; And
(B) the following components (i) to (iii) comprise a premixed mixture:
(i) a compound represented by the general formula:
HR 2 2 SiO (R 2 2 SiO) m SiR 2 2 H
(Wherein R 2 represents an identical or different monovalent hydrocarbon group lacking an aliphatic unsaturated bond, more than 15 mol% of R 2 in one molecule is an aryl group, and m is an integer of 1 to 100) Polysiloxanes;
(ii) a hydrosilylation reaction metal catalyst in an amount such that the catalyst metal is in the range of 0.01 to 1,000 ppm by mass with respect to the component (B); And
(iii)
R 3 2 NR 4 -NR 3 2
(B) represented by the general formula (1), wherein R 3 is the same or different and represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and R 4 represents an alkylene group having 2 to 4 carbon atoms, ≪ / RTI > to 1,000 ppm.
The component (ii) in component (B) is preferably a platinum-alkenylsiloxane complex and component (iii) is preferably N, N, N ', N'-tetramethylethylenediamine.
The composition preferably comprises (C) a compound represented by the general formula:
R 5 3 SiO (R 5 2 SiO) n SiR 5 3
Wherein at least two of R 5 in the molecule are alkenyl groups and at least 20 mol% of R 5 is an aryl group, and n is an integer of 5 to 1,000, in which R 5 represents the same or different monovalent hydrocarbon groups, ) In an amount of 100 parts by mass or less per 100 parts by mass of the component (A).
The present composition preferably comprises (D)
(HR 6 2 SiO 1/2) f (R 6 SiO 3/2) g (R 6 2 SiO 2/2) h (R 6 3
(Wherein, R 6 has only the same or a different one aliphatic unsaturated bond lacking represent a hydrocarbon group, at least 10 mole% of R 6 in one molecule is an aryl group; Y represents a hydrogen atom or alkyl; f is a positive J represents a number of 0 to 0.3, and k represents a number of 0 to 0.4, preferably 0 to 0. < RTI ID = 0.0 > G / h + i + j = 1), wherein f / g is a number from 0.1 to 4, h / g is a number from 0 to 10, i / g is a number from 0 to 5, Is used in an amount such that the silicon-bonded hydrogen atoms in component (D) are preferably from 1 to 20 mole percent of the total silicon-bonded hydrogen atoms in component (B) and component (D) .
In the optical semiconductor device of the present invention, the optical semiconductor element is sealed, protected, or covered with a cured product of the one-pack type curable silicone composition described above.
The one-pack type curable silicone composition of the present invention has storage stability and the optical semiconductor device of the present invention has reliability.
1 is a sectional view of an LED which is an example of the optical semiconductor device of the present invention.
First, the one-pack type curable silicone composition of the present invention will be described in detail.
Component (A) is a branched chain organopolysiloxane which is the main material of the composition and is represented by the following average unit formula:
(R 1 SiO 3/2 ) a (R 1 2 SiO 2/2 ) b (R 1 3 SiO 1/2 ) c (SiO 4/2 ) d (XO 1/2 ) e
In the above formula, R 1 represents the same or different monovalent hydrocarbon group. Specific examples include an alkyl group such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group; An alkenyl group such as a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group; An aryl group such as a phenyl group, a tolyl group, a xylyl group; An aralkyl group such as a benzyl group or a phenethyl group; Halogenated alkyl groups such as the 3-chloropropyl group, and the 3,3,3-trifluoropropyl group. However, at least 5 mol% of R 1 in one molecule is an alkenyl group, and preferably at least 10 mol% of R 1 is an alkenyl group. Furthermore, at least 30 mol% of R 1 is an aryl group, and preferably at least 40 mol% of R 1 is an aryl group. This is because, due to refraction, reflection, or dispersion, attenuation of light from the resulting cured product is reduced . Furthermore, in the above formula, X represents a hydrogen atom or an alkyl group. Examples of such alkyl groups include methyl, ethyl, propyl, and butyl.
B represents 0 or a positive integer; c represents 0 or a positive integer; d represents a number of 0 to 0.3; and e represents a number of 0 to 0.4. B / a represents a number of 0 to 10, c / a represents a number of 0 to 5, and a + b + c + d = 1.
Component (B) is a crosslinking agent of the present composition, and a catalyst for promoting such crosslinking. (I) a compound represented by the general formula:
HR 2 2 SiO (R 2 2 SiO) m SiR 2 2 H
(Ii) a hydrosilylation reaction metal-based catalyst and (iii) an organopolysiloxane represented by the following general formula:
R 4 2 NR 5 -NR 4 2
With an amine compound represented by the following formula (1).
In component (i), R 2 represents an identical or different monovalent hydrocarbon group lacking an aliphatic unsaturated bond. Specific examples include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group; An aryl group such as a phenyl group, a tolyl group, a xylyl group; Aralkyl groups such as benzyl or phenethyl; Halogenated alkyl groups such as the 3-chloropropyl group, and the 3,3,3-trifluoropropyl group. However, at least 15 mol% of R 2 in one molecule is an aryl group, it is preferably 30 mol% or more is an aryl group of R 2 or R 2 of 20 mol% or more. This is because, due to refraction, reflection, or dispersion, the attenuation of light from the resulting cured product is reduced. Further, in the above formula, m represents an integer of 1 to 100, preferably an integer of 1 to 50, and most preferably an integer of 1 to 20. [ This is because, when m is less than the maximum value in the above-mentioned range, work efficiency in handling the resulting composition is improved.
Examples of component (ii) include a platinum catalyst, a rhodium catalyst and a palladium catalyst, and a platinum catalyst is preferred. Examples of such platinum catalysts include fine platinum powder, chloroplatinic acid, alcoholic solution of chloroplatinic acid, platinum-alkenylsiloxane complexes, platinum-olefin complexes, and platinum-carbonyl complexes. Platinum-alkenylsiloxane complexes are preferred. Examples of the alkenylsiloxane include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane , Alkenylsiloxanes in which a part of the methyl groups of such alkenylsiloxanes are substituted with ethyl groups, phenyl groups, etc., and alkenylsiloxanes in which the vinyl groups of such alkenylsiloxanes are substituted with allyl groups, hexenyl groups, and the like. 1,3-divinyl-l, l, 3,3-tetramethyldisiloxane is preferred due to its excellent stability.
Further, in order to further improve the stability of such platinum-alkenylsiloxane complexes, alkenylsiloxanes such as 1,3-diallyl-1,1,3,3-tetramethyldisiloxane, 1,3- Diphenyl-1,3-dimethyl-1,3-diphenyldisiloxane, 1,3-divinyl-1,1,3,3-tetraphenyldisiloxane, 1,3,5,7-tetramethyl- 1,3,5,7-tetravinylcyclotetrasiloxane or an organosiloxane oligomer, such as a dimethylsiloxane oligomer, is preferably added to such a platinum-alkenylsiloxane complex.
The amount of the component (ii) to be added is such that the catalytic metal contained in the component (ii) reaches 0.01 to 1,000 ppm by mass in the component (B). Preferably, the amount is 0.1 to 1,000 ppm, or 0.1 to 500 ppm.
In the above formula, R 3 in component (iii) represents the same or different hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Examples of such an alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group. R 4 represents an alkylene group having 2 to 4 carbon atoms. Examples of such an alkylene group include an ethylene group, a propylene group, a methylmethylene group and a methylethylene group.
Examples of component (iii) include N, N, N ', N'-tetramethylethylenediamine, N, N-dimethylethylenediamine, N, Diamine, N, N, N ', N'-tetraethylethylenediamine.
Component (iii) is known as a reaction inhibitor in a hydrosilylation-curable silicone composition, but in conventional compositions these components are solely contained alone, while the storage stability of the one-part curable silicone composition is better than the composition ) And component (ii). ≪ / RTI >
The amount of the component (iii) added is 0.5 to 1,000 ppm, and preferably 1 to 400 ppm, in terms of mass in the component (B).
Component (B) is prepared by mixing components (i) to (iii) described above, but these components may be heated or may be cured at room temperature after mixing.
The content of component (B) in the present composition is 0.1 to 5 moles, and preferably 0.5 to 2 moles, of silicon-bonded hydrogen atoms in component (i) per mole of alkenyl group in component (A). This is because when the content of the component (B) is not lower than the lower limit of the above-mentioned range, the composition is sufficiently cured and the content of the component (B) is not more than the upper limit of the above-mentioned range, the heat resistance of the obtained cured product is improved.
To adjust the hardness of the resulting cured product, the present composition preferably comprises (C)
R 5 3 SiO (R 5 2 SiO) n SiR 5 3
Of the present invention may include a straight-chain organopolysiloxane represented by the following formula
In the above formula, R 5 represents the same or different monovalent hydrocarbon groups. An example is a group similar to that presented above for R < 1 >. However, two or more of R < 5 > in one molecule is an alkenyl group. In addition, at least 20 mol% of R 5 in one molecule is an aryl group. Preferably, at least 30 mol% of R 5 is an aryl group, and more preferably at least 40 mol% of R 5 is an aryl group. This is because, due to refraction, reflection, or dispersion, the attenuation of light from the resulting cured product is reduced. In addition, n is an integer of 5 to 1,000, preferably an integer of 5 to 100, and more preferably an integer of 5 to 50.
There is no particular limitation on the content of the component (C) in the present composition, but the content is preferably 100 parts by mass or less per 100 parts by mass of the component (A) so as not to significantly decrease the hardness of the resulting cured product, 70 parts by mass or less. Moreover, in order to suitably adjust the hardness of the resulting cured product and adjust the hardness of the resulting cured product, the above content is preferably more than 1 part by mass, more preferably more than 5 parts by mass, per 100 parts by mass of component (A).
In order to adjust the hardness of the resultant cured product and to impart mechanical strength, the composition preferably further comprises (D)
(HR 6 2 SiO 1/2) f (R 6 SiO 3/2) g (R 6 2 SiO 2/2) h (R 6 3
Lt; RTI ID = 0.0 > organopolysiloxanes < / RTI >
In the above formula, R 6 represents the same or different monovalent hydrocarbon group lacking an aliphatic unsaturated bond. A specific example is a group similar to that shown in the above-mentioned R 2 . However, at least 10 mol% of R 6 in one molecule is an aryl group. At least 15 mol% of R 6 is preferably an aryl group, and more preferably at least 20 mol% of R 6 is an aryl group. This is because, due to refraction, reflection, or dispersion, the attenuation of light from the resulting cured product is reduced. Furthermore, in the above formula, Y represents a hydrogen atom or an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group.
Wherein h represents 0 or a positive integer, i represents 0 or a positive integer, j represents a number of 0 to 0.3, and k represents 0 or a positive integer, and f represents a positive integer, g represents a positive integer, G represents a number of from 0 to 10, i / g represents a number of from 0 to 50, f + g + h represents a number of from 0 to 4, f / g represents a number of from 0.1 to 4, h / + i + j = 1.
There is no particular limitation on the content of the component (D) in the composition. The content of silicon-bonded hydrogen atoms in component (D) is between 1 and 20 of the total silicon-bonded hydrogen atoms in component (B) and component (D) to give a suitable hardness and mechanical strength to the resulting cured product. Mol%, preferably 2 to 20 mol%, and more preferably 2 to 10 mol%. This is because, if the content of the component (D) exceeds the minimum value in the above-mentioned range, mechanical strength can be imparted to the resulting cured product. On the other hand, if the content is below the maximum value in the above-mentioned range, appropriate hardness can be imparted to the resulting cured product.
2-ol, 3,5-dimethyl-1-hexyn-3-ol or 2-phenyl-3-butyn- Come; Ene-in compounds such as 3-methyl-3-pentene-1-yl or 3,5-dimethyl-3-hexene-1-yl; Or 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetra Siloxanes or benzotriazoles may be included as optional ingredients in the compositions of the present invention. There is no particular limitation on the content of such an inhibitor, but it is preferably in the range of 0.0001 to 5 parts by mass per 100 parts by mass of the composition.
The composition of the present invention may also contain an adhesion-imparting agent to improve the adhesion of the composition. A preferred adhesive-imparting agent is an organosilicon compound having at least one alkoxy group bonded to a silicon atom in one molecule. Such alkoxy groups are exemplified by methoxy, ethoxy, propoxy, butoxy, and methoxyethoxy groups; Particularly preferred is a methoxy group. Furthermore, the non-alkoxy group bonded to the silicon atom of such an organosilicon compound is a substituted or unsubstituted monovalent hydrocarbon group such as an alkyl group, an alkenyl group, an aryl group, an aralkyl group, a halogenated alkyl group and the like; Glycidoxyalkyl groups such as 3-glycidoxypropyl group, 4-glycidoxybutyl group and the like; An epoxy cyclohexyl alkyl group such as a 2- (3,4-epoxycyclohexyl) ethyl group and a 3- (3,4-epoxycyclohexyl) propyl group; Oxiranyl alkyl groups such as 4-oxiranylbutyl group, 8-oxiranyloctyl group and the like; Acrylic group-containing monovalent organic groups such as 3-methacryloxypropyl group and the like; And hydrogen atoms. Such an organosilicon compound preferably has a group capable of reacting with an alkenyl group or a silicon-bonded hydrogen atom in the present composition. Specifically, such an organosilicon compound preferably has a silicon-bonded alkenyl group or a silicon-bonded hydrogen atom. Furthermore, since such an organic silicon compound preferably has at least one epoxy group-containing monovalent organic group in one molecule, as it can give good adhesion to various types of substrates. Organosilicon compounds of this type are exemplified by organosilane compounds, organosiloxane oligomers and alkyl silicates. The molecular structure of the organosiloxane oligomer or alkyl silicate is exemplified by a linear structure, a partially branched linear structure, a branched structure, a cyclic structure, and a network structure. A linear chain structure, a branched chain structure, and a network structure are particularly preferable. Organosilicon compounds of this type include silane compounds such as 3-glycidoxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-methacryloxypropyltrimethoxy Silane and the like; A siloxane compound having at least one silicon-bonded alkenyl group or silicon-bonded hydrogen atom in one molecule, and at least one silicon-bonded alkoxy group; A silane compound having at least one silicon-bonded alkoxy group or a mixture of a siloxane compound and at least one siloxane compound having at least one silicon-bonded hydroxyl group and at least one silicon-bonded alkenyl group in one molecule; And methyl polysilicate, ethyl polysilicate, and epoxy group-containing ethyl polysilicate. There is no particular limitation on the content of the adhesive-imparting agent in the present composition. Such an adhesive-imparting agent in a range of 0.01 to 10 parts by mass per 100 parts by mass of the composition is preferred.
Furthermore, inorganic fillers such as silica, glass, alumina or zinc oxide; Organic resin fine powder such as polymethacrylate resin; A heat resistant agent, a dye, a pigment, a flame retardant, a solvent, etc. may be included as a selective component in the composition of the present invention at a level at which the object of the present invention is not impaired.
Curing of the composition is promoted by heating, and heating to a temperature in the range of 50 to 200 DEG C is preferred to promote curing.
In addition, the composition has adequate storage stability even at temperatures of 25 占 폚, but is preferably cooled to a temperature of 5 占 폚 or lower.
The optical semiconductor device of the present invention will now be described in detail.
The optical semiconductor device of the present invention is characterized in that its optical semiconductor element is sealed, protected or covered with a cured product of the one-pack type curable silicone composition described above. The light emitting diode element is an example of such a optical semiconductor element. Another example of such optical semiconductor device is a light emitting diode (LED).
1 shows a cross-sectional view of an example of a surface mount LED of such an apparatus. In the LED device shown in Fig. 1, the
In the method of manufacturing the surface-mounted LED shown in Fig. 1, the
Example
The one-pack type curable silicone composition of the present invention as well as the optical semiconductor device will be described in detail by examples. Note that the viscosity is a value obtained at 25 占 폚. In the above formula, Me, Ph, and Vi represent a methyl group, a phenyl group, and a vinyl group, respectively.
The properties of the one-part curable silicone composition were evaluated as follows.
[Curing speed]
Alpha Technologies Rheometer MDR2000P was used to measure the torque change of the one-part curable silicone composition at 150 占 폚. The TS-1 (TS-1) was used as an index of the hardening speed. The TS-1 was measured as the time until the torque value reached 1 dNm immediately after starting the torque measurement.
[Change in viscosity]
The viscosity change of the one-pack type curable silicone composition at 25 占 폚 was measured using AR 550 from TA Instruments under the condition of a shear rate of 20 (1 / s).
[Example 1]
The following formula:
HMe 2 SiO (Ph 2 SiO) SiMe 2 H
100 parts by mass of an organopolysiloxane (content of silicon-bonded hydrogen atoms = 0.60% by mass, content of phenyl groups in all silicon-bonded organic groups = 33% by mole) represented by the following formula , 1,3,3-tetramethyldisiloxane complex (the amount by which platinum metal is 12 ppm in mass per such mixture), and N, N, N ', N'-tetramethylethylenediamine 100 ppm by mass) was uniformly mixed and cured at room temperature for 1 day.
Next, in the production of the one-pack type curable silicone composition, 20 parts by mass of this mixture was added in the following average unit formula:
(PhSiO 3/2 ) 0.75 (ViMe 2 SiO 1/2 ) 0.25
(Vinyl group content = 5.6 mass%, vinyl group content in the total silicon-bonded organic groups = 17 mole%, phenyl group content in the total silicon-bonded organic groups = 50 mole%) represented by the following formula Part number average molecular weight is 2,260, and the following average unit formula:
(PhSiO 3/2 ) 0.40 (HMe 2 SiO 1/2 ) 0.60
3 parts by mass of a branched chain organopolysiloxane (content of silicon-bonded hydrogen atoms = 0.65% by mass, content of phenyl groups in all silicon-bonded organic groups = 25% by mole)
ViMe 2 SiO (PhMeSiO) 26 SiViMe 2
, 18 parts by mass of an organopolysiloxane represented by the following formula (content of vinyl groups = 1.4% by mass, content of phenyl groups in all silicon-bonded organic groups = 45% by mole), and 0.2 parts by mass of tetramethyltetravinylcyclotetrasiloxane . Table 1 shows the properties of this composition.
[Example 2]
The following formula:
HMe 2 SiO (Ph 2 SiO) SiMe 2 H
100 parts by mass of an organopolysiloxane (content of silicon-bonded hydrogen atoms = 0.60% by mass, content of phenyl groups in all silicon-bonded organic groups = 33% by mole) represented by the following formula , 1,3,3-tetramethyldisiloxane complex (the amount by which platinum metal is 16 ppm by mass for this mixture), and N, N, N ', N'-tetramethylethylenediamine 25 parts per million by mass) was uniformly mixed and cured at room temperature for 1 day.
Next, in the production of the one-pack type curable silicone composition, 20 parts by mass of this mixture was added in the following average unit formula:
(PhSiO 3/2 ) 0.75 (ViMe 2 SiO 1/2 ) 0.25
(Vinyl group content = 5.6 mass%, vinyl group content in the total silicon-bonded organic groups = 17 mole%, phenyl group content in the total silicon-bonded organic groups = 50 mole%) represented by the following formula Part number average molecular weight is 2,260, and the following average unit formula:
(PhSiO 3/2 ) 0.40 (HMe 2 SiO 1/2 ) 0.60
3 parts by mass of an organopolysiloxane (content of silicon-bonded hydrogen atoms = 0.65 mass%, content of phenyl groups in all silicon-bonded organic groups = 25 mol%) represented by the following formula:
ViMe 2 SiO (PhMeSiO) 26 SiViMe 2
, 18 parts by mass of an organopolysiloxane represented by the following formula (content of vinyl groups = 1.4% by mass, content of phenyl groups in all silicon-bonded organic groups = 45% by mole), and 0.2 parts by mass of tetramethyltetravinylcyclotetrasiloxane . Table 1 shows the properties of the composition.
[Comparative Example 1]
In the preparation of the one-pack type curable silicone composition,
HMe 2 SiO (Ph 2 SiO) SiMe 2 H
20 parts by mass of an organopolysiloxane represented by the following formula (content of silicon-bonded hydrogen atoms = 0.60% by mass, content of phenyl groups in all silicon-bonded organic groups = 33% by mole)
(PhSiO 3/2 ) 0.75 (ViMe 2 SiO 1/2 ) 0.25
(Vinyl group content = 5.6 mass%, vinyl group content in the total silicon-bonded organic groups = 17 mole%, phenyl group content in the total silicon-bonded organic groups = 50 mole%) represented by the following formula Part number average molecular weight is 2,260, and the following average unit formula:
(PhSiO 3/2 ) 0.40 (HMe 2 SiO 1/2 ) 0.60
3 parts by mass of an organopolysiloxane (content of silicon-bonded hydrogen atoms = 0.65 mass%, content of phenyl groups in all silicon-bonded organic groups = 25 mol%) represented by the following formula:
ViMe 2 SiO (PhMeSiO) 26 SiViMe 2
18 parts by mass of an organopolysiloxane represented by the following formula (content of vinyl group = 1.4% by mass, content of phenyl group in all silicon-bonded organic groups = 45% by mole), 1,3-divinyl- , 3-tetramethyldisiloxane complex (the amount by which the platinum metal is 2.6 ppm in mass per such mixture), 0.2 part by mass of 1-ethenyl-1-cyclohexanol and 0.2 parts by mass of tetramethyltetravinylcyclotetrasiloxane And uniformly mixed. Table 1 shows the properties of the composition.
[Table 1]
Industrial availability
The one-pack type curable silicone composition of the present invention has excellent storage stability, does not require mixing before use, and forms a cured product having high refractive index and high light transmittance. As a result, it is ideal as a sealant, adhesive, coating agent or protective agent for optical semiconductor devices.
Explanation of symbols
One Optical semiconductor element
2 Lead frame
3 Lead frame
4 Bonding wire
5 Frame material
6 The cured product of the one-pack type curable silicone composition
Claims (6)
(R 1 SiO 3/2 ) a (R 1 2 SiO 2/2 ) b (R 1 3 SiO 1/2 ) c (SiO 4/2 ) d (XO 1/2 ) e
(Wherein, R 1 has only the same or different 1 represent a hydrocarbon group, a 5 mol% is alkenyl group of R 1 in the molecule is at least 30 mol% of R 1 is an aryl group; X is a hydrogen atom or an alkyl A represents a positive integer, b represents 0 or a positive integer, c represents 0 or a positive integer, d represents a number of 0 to 0.3, e represents a number of 0 to 0.4 , b / a is a number from 0 to 10, c / a is a number from 0 to 5, and a + b + c + d = 1; And
(B) a one-pack type curable silicone composition comprising the following components (i) to (iii) in a premixed mixture:
(i) a compound represented by the general formula:
HR 2 2 SiO (R 2 2 SiO) m SiR 2 2 H
(Wherein R 2 represents an identical or different monovalent hydrocarbon group lacking an aliphatic unsaturated bond, more than 15 mol% of R 2 in one molecule is an aryl group, and m is an integer of 1 to 100) Polysiloxane,
(ii) a hydrosilylation reaction metal catalyst in an amount such that the catalyst metal is in the range of 0.01 to 1,000 ppm by mass with respect to the component (B); And
(iii)
R 3 2 NR 4 -NR 3 2
(B) represented by the general formula (1), wherein R 3 is the same or different and represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and R 4 represents an alkylene group having 2 to 4 carbon atoms, ≪ / RTI > to 1,000 ppm.
R 5 3 SiO (R 5 2 SiO) n SiR 5 3
Wherein at least two of R 5 in the molecule are alkenyl groups and at least 20 mol% of R 5 is an aryl group, and n is an integer of 5 to 1,000, in which R 5 represents the same or different monovalent hydrocarbon groups, ) In an amount of 100 parts by mass or less per 100 parts by mass of the component (A), based on 100 parts by mass of the linear organopolysiloxane.
(HR 6 2 SiO 1/2) f (R 6 SiO 3/2) g (R 6 2 SiO 2/2) h (R 6 3 SiO 1/2) i (SiO 4/2) j (YO 1 / 2 ) k
(Wherein, R 6 has only the same or a different one aliphatic unsaturated bond lacking represent a hydrocarbon group, at least 10 mole% of R 6 in one molecule is an aryl group; Y represents a hydrogen atom or alkyl; f is a positive J represents a number of 0 to 0.3, and k represents a number of 0 to 0.4, preferably 0 to 0. < RTI ID = 0.0 > G / h + i + j = 1), wherein f / g is a number from 0.1 to 4, h / g is a number from 0 to 10, i / g is a number from 0 to 5, Is used in an amount such that the silicon-bonded hydrogen atoms in component (D) are preferably from 1 to 20 mole percent of the total silicon-bonded hydrogen atoms in component (B) and component (D) Lt; RTI ID = 0.0 > 1 < / RTI >
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| PCT/JP2014/073113 WO2015030259A1 (en) | 2013-08-30 | 2014-08-27 | One-part curable silicone composition and optical semiconductor device |
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| US4584361A (en) * | 1985-06-03 | 1986-04-22 | Dow Corning Corporation | Storage stable, one part polyorganosiloxane compositions |
| US4791186A (en) * | 1988-01-04 | 1988-12-13 | Dow Corning Corporation | Method for preparing storage stable, one part curable polyorganosiloxane compositions |
| JP2623380B2 (en) * | 1991-06-03 | 1997-06-25 | 信越化学工業株式会社 | Silicone composition with excellent thermal conductivity |
| US5270422A (en) * | 1992-07-02 | 1993-12-14 | Dow Corning Corporation | Curing catalyst compositions and method for preparing same |
| JP2849027B2 (en) * | 1993-06-10 | 1999-01-20 | 信越化学工業株式会社 | One-part curable silicone composition |
| JP2006063092A (en) * | 2004-07-29 | 2006-03-09 | Dow Corning Toray Co Ltd | Curable organopolysiloxane composition, its curing method, optical semiconductor device and adhesion promoter |
| JP2009527622A (en) * | 2006-02-24 | 2009-07-30 | ダウ・コーニング・コーポレイション | Light emitting device encapsulated with silicone and curable silicone composition for preparing said silicone |
| JP2012052035A (en) * | 2010-09-01 | 2012-03-15 | Shin-Etsu Chemical Co Ltd | Addition-curable silicone composition, optical element encapsulating material comprising the composition, and semiconductor device in which optical element is encapsulated with cured product of the optical element encapsulating material |
| CN102093719B (en) * | 2010-12-27 | 2014-05-07 | 东莞市阿比亚能源科技有限公司 | High-power light emitting diode (LED) chip packaging soft gel |
| CN102250355B (en) * | 2011-05-30 | 2013-01-09 | 中科院广州化学有限公司 | Fluorine- and epoxide group-containing polysiloxane, and preparation method and application thereof |
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