KR20180051392A - Heat-curable silicone composition, die bond material, and optical semiconductor device - Google Patents
Heat-curable silicone composition, die bond material, and optical semiconductor device Download PDFInfo
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- KR20180051392A KR20180051392A KR1020170145665A KR20170145665A KR20180051392A KR 20180051392 A KR20180051392 A KR 20180051392A KR 1020170145665 A KR1020170145665 A KR 1020170145665A KR 20170145665 A KR20170145665 A KR 20170145665A KR 20180051392 A KR20180051392 A KR 20180051392A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- silicone composition
- component
- siloxane
- optical semiconductor
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 64
- 239000004065 semiconductor Substances 0.000 title claims description 54
- 230000003287 optical effect Effects 0.000 title claims description 51
- 239000000463 material Substances 0.000 title claims description 47
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000000962 organic group Chemical group 0.000 claims abstract description 32
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 11
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 10
- 239000012933 diacyl peroxide Substances 0.000 claims abstract description 9
- -1 peroxy ester Chemical class 0.000 claims description 37
- 238000001723 curing Methods 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- 238000013007 heat curing Methods 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 11
- 230000005764 inhibitory process Effects 0.000 abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 abstract description 11
- 239000001301 oxygen Substances 0.000 abstract description 11
- 239000000047 product Substances 0.000 description 36
- 239000000758 substrate Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 150000002978 peroxides Chemical class 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000006835 compression Effects 0.000 description 9
- 238000007906 compression Methods 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229910004283 SiO 4 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 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
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 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
- 229940106691 bisphenol a Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- DCVWZWOEQMSMLR-UHFFFAOYSA-N silylperoxysilane Chemical compound [SiH3]OO[SiH3] DCVWZWOEQMSMLR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- JXCAHDJDIAQCJO-UHFFFAOYSA-N (1-tert-butylperoxy-2-ethylhexyl) hydrogen carbonate Chemical compound CCCCC(CC)C(OC(O)=O)OOC(C)(C)C JXCAHDJDIAQCJO-UHFFFAOYSA-N 0.000 description 1
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- TUGAMVVIFZLKTI-UHFFFAOYSA-N (3-methoxy-3-methylbutoxy)peroxycarbonyl (3-methoxy-3-methylbutyl)peroxy carbonate Chemical compound COC(C)(C)CCOOOC(=O)OC(=O)OOOCCC(C)(C)OC TUGAMVVIFZLKTI-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- FYRCDEARNUVZRG-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CC(C)CC(C)(C)C1 FYRCDEARNUVZRG-UHFFFAOYSA-N 0.000 description 1
- VBQCFYPTKHCPGI-UHFFFAOYSA-N 1,1-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CCCCC1 VBQCFYPTKHCPGI-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
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- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- CHKCPIUYSMYEEW-UHFFFAOYSA-N 2-(2-cyclohexylpropan-2-ylperoxy)-2-ethylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)OOC(C)(C)C1CCCCC1 CHKCPIUYSMYEEW-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- IEMBFTKNPXENSE-UHFFFAOYSA-N 2-(2-methylpentan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCCC(C)(C)OOC(C)(C)OC(O)=O IEMBFTKNPXENSE-UHFFFAOYSA-N 0.000 description 1
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- WXDJDZIIPSOZAH-UHFFFAOYSA-N 2-methylpentan-2-yl benzenecarboperoxoate Chemical compound CCCC(C)(C)OOC(=O)C1=CC=CC=C1 WXDJDZIIPSOZAH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- UNKQAWPNGDCPTE-UHFFFAOYSA-N [2,5-dimethyl-5-(3-methylbenzoyl)peroxyhexan-2-yl] 3-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC(C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C=2C=C(C)C=CC=2)=C1 UNKQAWPNGDCPTE-UHFFFAOYSA-N 0.000 description 1
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
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Images
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
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- 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
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- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Led Device Packages (AREA)
- Silicon Polymers (AREA)
- Die Bonding (AREA)
Abstract
Description
본 발명은, 가열 경화형 실리콘 조성물, 해당 조성물을 포함하는 다이 본드재 및 해당 다이 본드재의 경화물을 사용한 광 반도체 장치에 관한 것이다.The present invention relates to a heat curable silicone composition, a die bond material containing the composition, and a photosemiconductor device using the cured product of the die bond material.
발광 다이오드(LED) 등의 광반도체 소자는 전력 소비량이 적다는 우수한 특성을 갖기 때문에, 옥외 조명 용도나 자동차 용도의 광반도체 디바이스로의 적용이 증가되고 있다. 이러한 광반도체 디바이스는, 일반적으로 청색광, 근자외광 또는 자외광을 발광하는 광반도체 발광 소자로부터 발하는 광을, 파장 변환 재료인 형광체에 의해 파장 변환하여 의사 백색이 얻어지도록 한 발광 장치이다. 이러한 광반도체 디바이스 중, 광반도체 소자는 다이 본드재를 사용하여 하우징에 접착·고정되어 있다.2. Description of the Related Art Optical semiconductor devices such as light emitting diodes (LEDs) have excellent characteristics of low power consumption, and thus their application to optical semiconductor devices for use in outdoor lighting and automobiles is increasing. Such a photo semiconductor device is a light emitting device in which light emitted from a photosemiconductor light emitting element that emits blue light, near ultraviolet light, or ultraviolet light is wavelength-converted by a phosphor that is a wavelength conversion material to obtain a pseudo white color. Among these optical semiconductor devices, the optical semiconductor element is bonded and fixed to the housing using a die bond material.
광반도체 소자용 다이 본드재 조성물로서는, 종래, 접착성이나 기계적 강도가 우수한 비스페놀 A형 에폭시 수지와, UV 흡수가 없는 에폭시 수지, 예를 들어 수소 첨가 비스페놀 A형 에폭시 수지 또는 지환식 에폭시 수지와, 경화제 및 경화 촉매를 포함하는 조성물이 다용되어 왔다. 그러나, LED 소자의 휘도 및 출력이 높아지는데 수반하여, LED 소자로부터의 자외광, 열 등에 의해, 접착층의 변색 및 크랙의 문제가 일어나고 있다.As the die bonding material composition for optical semiconductor elements, bisphenol A type epoxy resins having excellent adhesiveness and mechanical strength and epoxy resins having no UV absorption, such as hydrogenated bisphenol A type epoxy resins or alicyclic epoxy resins, A composition containing a curing agent and a curing catalyst has been widely used. However, along with the increase in luminance and output of the LED element, there has been a problem of discoloration and cracking of the adhesive layer due to ultraviolet light and heat from the LED element.
그래서, 광반도체 소자용 다이 본드재에 있어서의 에폭시 수지의 대체로서, 실리콘 수지를 사용하는 것이 제안되어 있다(특허문헌 1, 2). 실리콘 수지의 경화 기구는 여러 갈래에 걸치지만, 백금 촉매를 사용한 SiH기와 알케닐기의 부가 반응이 주로 사용된다. 이때, 기재와의 접착성을 향상시키는 목적에서 (메트)아크릴기나 에폭시기 등을 갖는 접착성 향상제를 첨가하는 경우가 많다. 접착성 향상제는, 첨가량이 적으면 접착성이 모자라지만, 너무 많으면 경화 후 물성에 대한 기여가 커져, 예를 들어 경도의 저하 등을 초래하기 때문에 다량으로 사용할 수 없다.Therefore, it has been proposed to use a silicone resin as a substitute for an epoxy resin in a die bonding material for optical semiconductor elements (Patent Documents 1 and 2). Although the curing mechanism of the silicone resin extends over several branches, the addition reaction of SiH groups and alkenyl groups using a platinum catalyst is mainly used. At this time, for the purpose of improving the adhesiveness to a substrate, an adhesive property improving agent having a (meth) acrylic group or an epoxy group is often added. If the amount of the adhesion improver is too small, the adhesion is insufficient, but if it is too much, the contribution to the physical properties after curing becomes large, for example, the hardness is lowered and the like.
한편, 접착성 관능기인 메타크릴기 등을 사용한 퍼옥시드 경화를 이용한 사례는 있지만(특허문헌 3, 4), 산소에 의한 경화 저해 때문에 표면의 경화성이 나빠진다는 문제가 있었다. 또한, 메타크릴기 등을 UV 조사로 경화시킬 때에도 산소에 의한 경화 저해가 일어나기 때문에, 그 영향을 부가 경화에 의해 해결하는 방법이 제안되어 있지만(특허문헌 5), 이러한 방법은, 실제로는 UV 경화와 열경화의 양쪽을 필요로 하기 때문에, UV 조사를 행할 수 없는 것과 같은 복잡한 장치 설계를 요하는 부위로의 적용은 곤란하였다.On the other hand, there is an example in which peroxide curing using a methacryl group or the like as an adhesive functional group is used (
본 발명은 상기 사정을 감안하여 이루어진 것으로, 산소 저해에 의한 표면 부분의 미경화를 극복한 경화물을 부여할 수 있는 가열 경화형의 실리콘 조성물을 제공하는 것을 목적으로 한다. 또한, 해당 조성물을 포함하는 다이 본드재를 제공하는 것을 목적으로 한다. 또한, 해당 다이 본드재의 경화물을 갖는 광반도체 장치를 제공하는 것을 목적으로 한다.SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and it is an object of the present invention to provide a heat curable silicone composition capable of giving a cured product overcoming the non-curing of the surface portion due to oxygen inhibition. It is another object of the present invention to provide a die bond material containing the composition. It is another object of the present invention to provide an optical semiconductor device having a cured product of the die-bonding material.
상기 과제를 해결하기 위해서, 본 발명에 따르면,In order to solve the above problems, according to the present invention,
(A) 하기 일반식 (1)로 표시되는 구조를 분자 중에 적어도 하나 갖는 오르가노(폴리)실록산: 100질량부,(A) 100 parts by mass of an organo (poly) siloxane having at least one structure represented by the following general formula (1) in a molecule,
[식 중, m은 0, 1, 2 중 어느 것이고, R1은 수소 원자, 페닐기 또는 할로겐화 페닐기, R2는 수소 원자 또는 메틸기, R3은 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 12의 1가의 유기기, Z1은 -R4-, -R4-O-, -R4(CH3)2Si-O-(R4는 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기) 중 어느 것, Z2는 산소 원자 또는 치환 혹은 비치환으로 동일 혹은 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기임]R 2 is a hydrogen atom or a methyl group, R 3 is a substituted or unsubstituted, or the same or different, the number of carbon atoms which may be the same or different, and m is 0 or 1 or 2; R 1 is a hydrogen atom, a phenyl group or a halogenated phenyl group; 1 to 12, Z 1 represents -R 4 -, -R 4 -O-, -R 4 (CH 3 ) 2 Si-O- (wherein R 4 may be substituted or unsubstituted, And Z 2 is an oxygen atom or a divalent organic group having 1 to 10 carbon atoms which may be the same or different and are substituted or unsubstituted,
(B) 디아실퍼옥시드, 퍼옥시에스테르로부터 선택되는 1종 이상을 포함하는 유기 과산화물: 0.1 내지 30질량부,(B) 0.1 to 30 parts by mass of an organic peroxide containing at least one selected from diacyl peroxide and peroxy ester,
(C) 1분자 중에 규소 원자에 결합한 수소 원자를 적어도 2개 함유하는 오르가노히드로겐폴리실록산: 0.1 내지 20질량부,(C) 0.1 to 20 parts by mass of an organohydrogenpolysiloxane containing at least two hydrogen atoms bonded to silicon atoms in one molecule,
(D) 백금계 촉매: (A) 성분에 대하여 (D) 성분 중의 백금 질량 환산으로 0.01 내지 1,000ppm이 되는 양(D) Platinum-based catalyst: The amount of the platinum-based catalyst is 0.01 to 1,000 ppm in terms of platinum mass in the component (D)
을 함유하는 것을 특징으로 하는 가열 경화형 실리콘 조성물을 제공한다.And a thermosetting silicone composition.
본 발명의 가열 경화형 실리콘 조성물은 (메트)아크릴기의, 퍼옥시드에 의한 경화와, SiH기와 불포화기의 부가 반응의 양쪽의 경화를 행함으로써, 산소 저해에 의한 표면 부분의 미경화를 극복한 경화물을 부여하는 것이 된다.The heat curable silicone composition of the present invention is a heat curable silicone composition wherein a (meth) acryl group is cured by peroxide and an addition reaction of an SiH group and an unsaturated group are both cured, Cargo is given.
또한 이 경우, 상기 (A) 성분의 오르가노(폴리)실록산의 Z1이 -R4-이고, Z2가 산소 원자인 것이 바람직하다.In this case, it is preferable that Z 1 of the organo (poly) siloxane of the component (A) is -R 4 - and Z 2 is an oxygen atom.
또한 이 경우, 상기 (A) 성분의 오르가노(폴리)실록산의 Z1이 -R4-O- 또는 -R4(CH3)2Si-O-이고, Z2가 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기인 것이 바람직하다.In this case, it is preferable that Z 1 of the organo (poly) siloxane of the component (A) is -R 4 -O- or -R 4 (CH 3 ) 2 Si-O- and Z 2 is substituted or unsubstituted Or a divalent organic group having 1 to 10 carbon atoms which may be different from each other.
이러한 Z1, Z2의 조합인 (A) 성분을 포함하는 가열 경화형 실리콘 조성물이면, (B) 성분이 분해할 때에 발생하는 자유 라디칼과 (A) 성분이 효과적으로 반응하여, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 얻을 수 있다.In the case of the heat curable silicone composition containing the component (A) as a combination of Z 1 and Z 2 , the free radical generated when the component (B) decomposes reacts effectively with the component (A) A cured product excellent in heat resistance, light resistance and crack resistance can be obtained.
또한, 상기 (A) 성분의 오르가노(폴리)실록산은, 해당 오르가노(폴리)실록산을 구성하는 전 실록산 단위 중 0.1mol％ 이상의 (SiO2) 단위를 갖는 것인 것이 바람직하다.It is preferable that the organo (poly) siloxane of the component (A) has 0.1 mol% or more of (SiO 2 ) units in the total siloxane units constituting the organo (poly) siloxane.
이러한 (A) 성분을 포함하는 가열 경화형 실리콘 조성물이면, (B) 성분이 분해할 때에 발생하는 자유 라디칼과 (A) 성분이 더욱 효과적으로 반응하여, 보다 한층, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 얻을 수 있다.The heat curable silicone composition containing the component (A) reacts more effectively with the free radicals generated when the component (B) decomposes, and furthermore, the adhesive strength and the workability are further improved. Further, A cured product having excellent heat resistance, light resistance and crack resistance can be obtained.
또한 본 발명에서는, 상기 가열 경화형 실리콘 조성물을 포함하는 것임을 특징으로 하는 다이 본드재를 제공한다.The present invention also provides a die-bonding material characterized in that it comprises the above-described heat-curing silicone composition.
본 발명의 가열 경화형 실리콘 조성물은, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 부여할 수 있기 때문에, 다이 본드재로서 적합하게 사용할 수 있다.The heat curable silicone composition of the present invention can be suitably used as a die bond material because it can provide a cured product excellent in bonding strength and workability and excellent in heat resistance, light resistance and crack resistance.
또한 본 발명에서는, 상기 다이 본드재를 경화하여 얻어지는 경화물을 갖는 것임을 특징으로 하는 광반도체 장치를 제공한다.The optical semiconductor device according to the present invention has a cured product obtained by curing the die bond material.
이러한 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 경화하여 얻어지는 경화물을 갖는 광반도체 장치는, 신뢰성이 높은 광반도체 장치가 된다.The optical semiconductor device having a cured product obtained by curing the die bond material containing the heat curable silicone composition of the present invention is a highly reliable optical semiconductor device.
본 발명의 가열 경화형 실리콘 조성물은, (메트)아크릴기의 퍼옥시드에 의한 경화와, SiH기와 불포화기의 부가 반응의 양쪽의 경화를 행함으로써, 산소 저해에 의한 표면 부분의 미경화를 극복한, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 부여할 수 있다. 이러한 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 경화하여 얻어지는 경화물을 갖는 광반도체 장치는, 신뢰성이 높은 광반도체 장치가 된다.The heat curable silicone composition of the present invention is a heat curable silicone composition which overcomes curing of the surface portion by oxygen inhibition by curing both peroxide of the (meth) acryl group and addition reaction of the SiH group and the unsaturated group, A cured product excellent in bonding strength and workability and excellent in heat resistance, light resistance and crack resistance can be provided. The optical semiconductor device having a cured product obtained by curing the die bond material containing the heat curable silicone composition of the present invention is a highly reliable optical semiconductor device.
도 1은 본 발명의 광반도체 장치의 일례를 도시하는 단면도이다.1 is a cross-sectional view showing an example of the optical semiconductor device of the present invention.
본 발명자는, 상기 목적을 달성하기 위하여 예의 검토를 행한 결과, 하기 (A) 내지 (D) 성분을 함유하는 것임을 특징으로 하는 가열 경화형 실리콘 조성물이라면, (메트)아크릴기의 퍼옥시드에 의한 경화와, SiH기와 불포화기의 부가 경화의 양쪽의 경화에 의해, UV 조사를 행하지 않아도, 산소 저해에 의한 표면 부분의 미경화를 극복한 경화물을 부여할 수 있는 가열 경화형 실리콘 조성물이 되는 것을 알아내어, 본 발명을 완성시켰다. 이하, 본 발명의 가열 경화형 실리콘 조성물, 다이 본드재 및 광반도체 장치에 대하여 상세하게 설명한다.The inventors of the present invention have conducted intensive studies in order to achieve the above object. As a result, it has been found that the silicone composition of the present invention contains the following components (A) to (D) Curing type silicone composition which can give a cured product that overcomes the uncured portion of the surface portion due to oxygen inhibition even when UV irradiation is not performed by curing both the SiH group and the addition curing of the unsaturated group, Thereby completing the present invention. Hereinafter, the heat curable silicone composition, die bond material and optical semiconductor device of the present invention will be described in detail.
즉, 본 발명은That is,
(A) 하기 일반식 (1)로 표시되는 구조를 분자 중에 적어도 하나 갖는 오르가노(폴리)실록산: 100질량부,(A) 100 parts by mass of an organo (poly) siloxane having at least one structure represented by the following general formula (1) in a molecule,
[식 중, m은 0, 1, 2 중 어느 것이고, R1은 수소 원자, 페닐기 또는 할로겐화 페닐기, R2는 수소 원자 또는 메틸기, R3은 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 12의 1가의 유기기, Z1은 -R4-, -R4-O-, -R4(CH3)2Si-O-(R4는 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기) 중 어느 것, Z2는 산소 원자 또는 치환 혹은 비치환으로 동일 혹은 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기임]R 2 is a hydrogen atom or a methyl group, R 3 is a substituted or unsubstituted, or the same or different, the number of carbon atoms which may be the same or different, and m is 0 or 1 or 2; R 1 is a hydrogen atom, a phenyl group or a halogenated phenyl group; 1 to 12, Z 1 represents -R 4 -, -R 4 -O-, -R 4 (CH 3 ) 2 Si-O- (wherein R 4 may be substituted or unsubstituted, And Z 2 is an oxygen atom or a divalent organic group having 1 to 10 carbon atoms which may be the same or different and are substituted or unsubstituted,
(B) 디아실퍼옥시드, 퍼옥시에스테르로부터 선택되는 1종 이상을 포함하는 유기 과산화물: 0.1 내지 30질량부,(B) 0.1 to 30 parts by mass of an organic peroxide containing at least one selected from diacyl peroxide and peroxy ester,
(C) 1분자 중에 규소 원자에 결합한 수소 원자를 적어도 2개 함유하는 오르가노히드로겐폴리실록산: 0.1 내지 20질량부,(C) 0.1 to 20 parts by mass of an organohydrogenpolysiloxane containing at least two hydrogen atoms bonded to silicon atoms in one molecule,
(D) 백금계 촉매: (A) 성분에 대하여 (D) 성분 중의 백금의 질량 환산으로 0.01 내지 1,000ppm이 되는 양(D) Platinum-based catalyst: The amount of the platinum-based catalyst is 0.01 to 1,000 ppm in terms of mass of platinum in the component (D)
을 함유하는 것을 특징으로 하는 가열 경화형 실리콘 조성물을 제공한다.And a thermosetting silicone composition.
(A) 성분: (A) Component: 오르가노(폴리)실록산Organo (poly) siloxane
(A) 성분의 오르가노(폴리)실록산은, 하기 일반식 (1)로 표시되는 구조를 분자 중에 적어도 하나 갖는 오르가노(폴리)실록산이다. 또한, 본 발명에 있어서 오르가노(폴리)실록산이란, 1분자 중에 실록산 결합(-Si-O-Si-)이 하나인 오르가노실록산, 및/또는 1분자 중에 2개 이상의 실록산 결합을 포함하는 오르가노폴리실록산을 말한다.The organo (poly) siloxane of the component (A) is an organo (poly) siloxane having at least one structure represented by the following general formula (1) in the molecule. Further, in the present invention, the organo (poly) siloxane is an organosiloxane having one siloxane bond (-Si-O-Si-) in one molecule and / or an organosiloxane having two or more siloxane bonds in one molecule Refers to a polysiloxane.
[식 중, m은 0, 1, 2 중 어느 것이고, R1은 수소 원자, 페닐기 또는 할로겐화 페닐기, R2는 수소 원자 또는 메틸기, R3은 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 12의 1가의 유기기, Z1은 -R4-, -R4-O-, -R4(CH3)2Si-O-(R4는 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기) 중 어느 것, Z2는 산소 원자 또는 치환 혹은 비치환으로 동일 혹은 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기임]R 2 is a hydrogen atom or a methyl group, R 3 is a substituted or unsubstituted, or the same or different, the number of carbon atoms which may be the same or different, and m is 0 or 1 or 2; R 1 is a hydrogen atom, a phenyl group or a halogenated phenyl group; 1 to 12, Z 1 represents -R 4 -, -R 4 -O-, -R 4 (CH 3 ) 2 Si-O- (wherein R 4 may be substituted or unsubstituted, And Z 2 is an oxygen atom or a divalent organic group having 1 to 10 carbon atoms which may be the same or different and are substituted or unsubstituted,
(A) 성분의 오르가노(폴리)실록산 중의, Z1, Z2의 조합으로서는, Z1이 -R4-이고, Z2가 산소 원자인 것이나, Z1이 -R4-O- 또는, -R4(CH3)2Si-O-이고, Z2가 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기인 것이 바람직하다. 이러한 (A) 성분을 포함하는 가열 경화형 실리콘 조성물이라면, (B) 성분이 분해할 때에 발생하는 자유 라디칼과 (A) 성분이 효과적으로 반응하여, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 얻을 수 있다.Examples of the combination of Z 1 and Z 2 in the organo (poly) siloxane of the component (A) include those wherein Z 1 is -R 4 - and Z 2 is an oxygen atom, or Z 1 is -R 4 -O-, -R 4 (CH 3 ) 2 Si-O-, and Z 2 is a divalent organic group having 1 to 10 carbon atoms which may or may not be substituted or unsubstituted. The heat curable silicone composition containing the component (A) is advantageous in that the free radicals generated when the component (B) is decomposed effectively react with the component (A), and the adhesive strength and workability are excellent and the heat resistance, A cured product excellent in crack resistance can be obtained.
또한, (A) 성분의 오르가노(폴리)실록산을 구성하는 전 실록산 단위 중, 0.1mol％ 이상의 (SiO2) 단위를 갖는 것이 바람직하다. 이러한 (A) 성분을 포함하는 가열 경화형 실리콘 조성물이면, (B) 성분이 분해할 때에 발생하는 자유 라디칼과 (A) 성분이 더욱 효과적으로 반응하여, 보다 한층, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 얻을 수 있다.Further, it is preferable that the total siloxane units constituting the organo (poly) siloxane of component (A) have 0.1 mol% or more of (SiO 2 ) units. The heat curable silicone composition containing the component (A) reacts more effectively with the free radicals generated when the component (B) decomposes, and furthermore, the adhesive strength and the workability are further improved. Further, A cured product having excellent heat resistance, light resistance and crack resistance can be obtained.
또한, (A) 성분의 오르가노(폴리)실록산이, 하기 일반식 (2)로 표시되는 구조를 분자 중에 적어도 하나 갖는 것인 것이 바람직하다. 이러한 (A) 성분을 포함하는 가열 경화형 실리콘 조성물이라면, (B) 성분이 분해할 때에 발생하는 자유 라디칼과 (A) 성분이 더 효과적으로 반응하고, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 얻을 수 있다.It is also preferable that the organo (poly) siloxane of the component (A) has at least one structure represented by the following general formula (2) in the molecule. In the case of the heat curable silicone composition containing the component (A), the free radicals generated upon decomposition of the component (B) react more effectively with the component (A), the adhesive strength and workability are excellent, And a cured product excellent in crack resistance can be obtained.
(식 중, m, R1, R2, R3, R4는 상기와 동일함)(Wherein m, R 1 , R 2 , R 3 and R 4 are as defined above)
(A) 성분의 오르가노(폴리)실록산은, 25℃에서의 점도가 5mPa·s 이상의 액상 또는 고체의 분지상 또는 3차원 망상 구조의 오르가노폴리실록산인 것이 바람직하다.The organo (poly) siloxane of component (A) is preferably a branched or solid branched or three-dimensional networked organopolysiloxane having a viscosity at 25 ° C of not less than 5 mPa · s.
상기 식 (1)에 있어서, R3으로 표시되는 규소 원자에 결합한 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 12의 1가의 유기기로서는, 바람직하게는 탄소 원자수 1 내지 8 정도의 것을 들 수 있고, 구체적으로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, tert-부틸기, 펜틸기, 네오펜틸기, 헥실기, 시클로헥실기, 옥틸기, 노닐기, 데실기 등의 알킬기, 페닐기, 톨릴기, 크실릴기, 나프틸기 등의 아릴기, 벤질기, 페닐에틸기, 페닐프로필기 등의 아르알킬기, 비닐기, 알릴기, 프로페닐기, 이소프로페닐기, 부테닐기, 헥세닐기, 시클로헥세닐기, 옥테닐기 등의 알케닐기나, 이들 기의 수소 원자의 일부 또는 전부를 불소, 브롬, 염소 등의 할로겐 원자, 시아노기 등으로 치환한 것, 예를 들어 클로로메틸기, 클로로프로필기, 브로모에틸기, 트리플루오로프로필기 등의 할로겐 치환 알킬기나 시아노에틸기 등을 들 수 있다.In the formula (1), the monovalent organic group having 1 to 12 carbon atoms, which may be the same or different, which is bonded to the silicon atom represented by R 3 , preferably has 1 to 8 carbon atoms And specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, An aryl group such as a phenyl group, a tolyl group, a xylyl group and a naphthyl group, an aralkyl group such as a benzyl group, a phenylethyl group and a phenylpropyl group, a vinyl group, an allyl group, a propenyl group, , An alkenyl group such as a butenyl group, a hexenyl group, a cyclohexenyl group and an octenyl group, a group obtained by substituting a part or all of the hydrogen atoms of these groups with a halogen atom such as fluorine, bromine or chlorine, A chloromethyl group, a chloropropyl group, Our group, there may be mentioned halogen-substituted alkyl group or cyano group and the like, such as propyl group trifluoromethyl.
이하에 (A) 성분의 오르가노(폴리)실록산을 예시한다.The organo (poly) siloxane of component (A) is exemplified below.
또한, (A) 성분의 오르가노(폴리)실록산으로서, 하기 식에 나타내는 MA 단위, M 단위, Q 단위가 MA:M:Q=1:4:6의 비율로 포함되고, 분자량이 폴리스티렌 환산 중량 평균 분자량으로 5,000인 오르가노폴리실록산,Further, it is preferable that the organopolysiloxane of the component (A) contains MA, M and Q units represented by the following formula in a ratio of MA: M: Q = 1: 4: 6, An organopolysiloxane having an average molecular weight of 5,000,
하기 식에 나타내는, MA-D 단위, D 단위, T 단위가 MA-D:D:T=2:6:7의 비율이고, 분자량이 폴리스티렌 환산 중량 평균 분자량으로 3500인 오르가노폴리실록산 등이 예시된다.Examples of the organopolysiloxane represented by the following formula include MA-D units, D units and T units in the ratio of MA-D: D: T = 2: 6: 7 and a molecular weight of 3500 in terms of polystyrene- .
또한, (A) 성분의 오르가노(폴리)실록산으로서, 하기에 나타나는 구조를 갖는 오르가노(폴리)실록산 등이 예시된다.Examples of the organo (poly) siloxane of component (A) include an organo (poly) siloxane having the structure shown below.
(식 중, p=18, q=180임)(Where p = 18 and q = 180)
(식 중, t=18, u=180임)(Where t = 18, u = 180)
이러한 (A) 성분의 합성 방법으로서는, 예를 들어 하기에 나타내는 오르가노히드로겐실란,Examples of the method for synthesizing such component (A) include organohydrogen silane,
(식 중, m, R1, R2, R3, Z1은 상기와 동일함)(Wherein m, R 1 , R 2 , R 3 and Z 1 are as defined above)
바람직하게는 하기 식에 나타내는 화합물,Preferably a compound represented by the following formula,
(식 중, m, R1, R2, R3, Z1, Z2는 상기와 동일함)(Wherein m, R 1 , R 2 , R 3 , Z 1 and Z 2 are as defined above)
보다 구체적으로는, 1,3-비스(3-메타크릴옥시프로필)테트라메틸디실록산과 1,1,3,3-테트라메틸디실록산을 산 촉매 존재 하에서 평형화 반응함으로써 얻어지는 (3-메타크릴옥시프로필)-1,1,3,3-테트라메틸디실록산과, 지방족 불포화기(예를 들어, 에틸렌성 불포화기 및 아세틸렌성 불포화기를 들 수 있음)를 포함하는 오르가노(폴리)실록산을, 백금 촉매 존재 하에서 히드로실릴화 반응시키면 되고, 이 방법으로 본 발명에 적합한 것을 제조할 수 있지만, 상기한 합성 방법에 제한되는 것은 아니다. 또한, 지방족 불포화기를 포함하는 오르가노(폴리)실록산은, 지방족 불포화기를 갖는 오르가노알콕시실란을 포함하는 알콕시실란의 (공)가수분해 축합 등 공지된 방법으로 제조할 수 있고, 시판하는 것을 사용해도 된다.More specifically, it is possible to use (3-methacryloxypropyl) tetramethyldisiloxane obtained by equilibration reaction of 1,3-bis (3-methacryloxypropyl) tetramethyldisiloxane with 1,1,3,3-tetramethyldisiloxane in the presence of an acid catalyst Propyl) -1,1,3,3-tetramethyldisiloxane and an aliphatic unsaturated group (for example, an ethylenically unsaturated group and an acetylenic unsaturated group) The hydrosilylation reaction may be carried out in the presence of a catalyst. According to this method, there can be produced a product suitable for the present invention. However, the method is not limited to the above-mentioned synthesis method. Further, the organo (poly) siloxane containing an aliphatic unsaturated group can be produced by a known method such as (co) hydrolysis and condensation of an alkoxy silane containing an organoalkoxysilane having an aliphatic unsaturated group, and even if commercially available do.
이들 (A) 성분은 단일이거나, 2종 이상을 병용해도 된다.These (A) components may be used singly or in combination of two or more.
또한, (A) 성분에는, 조성물의 점도나 경화물의 경도를 조정하는 등의 목적으로, 이하에 도시한 바와 같은 실리콘을 포함하는 반응성 희석제나, 실리콘을 포함하지 않는 반응성 희석제를 첨가할 수 있다.For the purpose of adjusting the viscosity of the composition and the hardness of the cured product, a reactive diluent containing silicon or a reactive diluent containing no silicone as shown below may be added to the component (A).
실리콘을 포함하는 반응성 희석제로서는, 하기 구조를 갖는 오르가노폴리실록산을 들 수 있다.Examples of the reactive diluent containing silicon include an organopolysiloxane having the following structure.
(r=20, s=180임)(r = 20, s = 180)
이러한 실리콘을 포함하는 반응성 희석제는 단일이거나, 2종 이상을 병용해도 된다.The reactive diluent containing such silicon may be used singly or in combination of two or more.
실리콘을 포함하지 않는 반응성 희석제로서는, H2C=CGCO2R5에 의해 나타낸 바와 같은 (메트)아크릴레이트류가 있고, 상기 식 중, G는 수소, 할로겐 또는 1 내지 약 4개의 탄소 원자의 알킬이고; R5는 1 내지 약 16개의 탄소 원자를 갖는 알킬, 시클로알킬, 알케닐, 시클로알케닐, 알칼리, 아르알킬 또는 아릴기로부터 선택되고, 이들 중 어느 하나는 필요에 따라, 실란, 규소, 산소, 할로겐, 카르보닐, 히드록실, 에스테르, 카르복실산, 요소, 우레탄, 카르바메이트, 아민, 아미드, 황, 술포네이트, 술폰 등으로 치환 또는 차단할 수 있다.As reactive diluents that do not include silicon, there are (meth) acrylates such as those represented by H 2 C = CGCO 2 R 5 wherein G is hydrogen, halogen or alkyl of 1 to about 4 carbon atoms ego; R 5 is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl or aryl groups having 1 to about 16 carbon atoms, any of which may optionally be substituted with silane, May be substituted or blocked with halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate,
반응성 희석제로서 특히 바람직한 더욱 상세한 (메트)아크릴레이트류로서는, 폴리에틸렌글리콜디(메트)아크릴레이트, 에톡시화 비스페놀-A(메트)아크릴레이트("EBIPA" 또는 "EBIPMA")와 같은 비스페놀-A디(메트)아크릴레이트, 테트라히드로푸란(메트)아크릴레이트 및 디(메트)아크릴레이트, 시트로네릴아크릴레이트 및 시트로네릴메타크릴레이트, 히드록시프로필(메트)아크릴레이트, 헥산디올디(메트)아크릴레이트("HDDA" 또는 "HDDMA"), 트리메틸올프로판트리(메트)아크릴레이트, 테트라히드로디시클로펜타디에닐(메트)아크릴레이트, 에톡시화 트리메틸올프로판트리아크릴레이트("ETTA"), 트리에틸렌글리콜디아크릴레이트 및 트리에틸렌글리콜디메타크릴레이트("TRIEGMA"), 이소보르닐아크릴레이트 및 이소보르닐메타크릴레이트, 그리고 이들에 상응한 아크릴레이트에스테르가 있다. 물론, 이들의 (메트)아크릴레이트류의 조합도 반응성 희석제로서 사용할 수 있다.Particularly preferred (meth) acrylates that are particularly preferred as reactive diluents include bisphenol-A di (meth) acrylates such as polyethylene glycol di (meth) acrylate, ethoxylated bisphenol-A (meth) acrylate ("EBIPA" or "EBIPMA" (Meth) acrylate, tetrahydrofuran (meth) acrylate and di (meth) acrylate, citronelyl acrylate and citronellyl methacrylate, hydroxypropyl (meth) acrylate, hexanediol di ("HDDA" or "HDDMA"), trimethylolpropane tri (meth) acrylate, tetrahydrodicyclopentadienyl (meth) acrylate, ethoxylated trimethylolpropane triacrylate Glycol diacrylate and triethylene glycol dimethacrylate ("TRIEGMA"), isobornyl acrylate and isobornyl methacrylate, and corresponding acrylates Ester. Of course, combinations of these (meth) acrylates can also be used as reactive diluents.
반응성 희석제를 첨가하는 경우의 첨가량으로서는, 본 발명의 가열 경화형 실리콘 조성물량에 대하여 0.01 내지 40질량％의 범위가 바람직하고, 0.05 내지 20질량％의 범위가 보다 바람직하다.The amount of the reactive diluent added is preferably in the range of 0.01 to 40% by mass, and more preferably in the range of 0.05 to 20% by mass with respect to the amount of the thermosetting silicone composition of the present invention.
(B) (B) 디아실퍼옥시드Diacyl peroxide , , 퍼옥시에스테르로부터From peroxy ester 선택되는 1종 이상을 포함하는 유기 과산화물 Organic peroxides comprising at least one selected < RTI ID = 0.0 >
(B)성분의 디아실퍼옥시드, 퍼옥시에스테르로부터 선택되는 1종 이상을 포함하는 유기 과산화물은, 본 발명의 가열 경화형 실리콘 조성물을 원하는 형상으로 성형한 후에, 가열 처리를 가하여 가교 반응에 의해 경화시키기 위하여 배합되는 성분이고, 목적으로 하는 접속 온도, 접속 시간, 가용 시간 등에 의해 적절히 선택된다.The organic peroxide containing at least one member selected from the group consisting of diacyl peroxide and peroxy ester of the component (B) can be obtained by subjecting the heat curable silicone composition of the present invention to a desired shape and then heat- And is appropriately selected according to the intended connection temperature, connection time, available time, and the like.
유기 과산화물은, 높은 반응성과 긴 가용 시간을 양립하는 관점에서, 반감기 10시간의 온도가 40℃ 이상이며 또한 반감기 1분의 온도가 200℃ 이하인 것이 바람직하고, 반감기 10시간의 온도가 60℃ 이상이며 또한 반감기 1분의 온도가 180℃ 이하인 것이 보다 바람직하다.From the viewpoint of achieving both high reactivity and long usable time, the organic peroxide preferably has a temperature of 40 占 폚 or higher for a half-life period of 10 hours and a temperature of 200 占 폚 or lower for a half-life period, It is more preferable that the temperature at a half-life of 1 minute is 180 占 폚 or less.
디아실퍼옥시드로서는, 예를 들어 이소부틸퍼옥시드, 2,4-디클로로벤조일퍼옥시드, 3,5,5-트리메틸헥사노일퍼옥시드, 옥타노일퍼옥시드, 라우로일퍼옥시드, 스테아로일퍼옥시드, 숙시닉퍼옥시드, 벤조일퍼옥시톨루엔 및 벤조일퍼옥시드를 들 수 있다.Examples of the diacyl peroxide include isobutyl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, Methylcyclohexane, methylcyclohexane, methylcyclohexane, methylcyclohexane, methylcyclohexane, methylcyclohexanone, methylcyclohexanone,
퍼옥시에스테르로서는, 예를 들어 쿠밀퍼옥시네오데카노에이트, 1,1,3,3-테트라메틸부틸퍼옥시네오데카노에이트, 1-시클로헥실-1-메틸에틸퍼옥시네오데카노에이트, t-헥실퍼옥시네오데카노에이트, t-부틸퍼옥시피발레이트, 1,1,3,3-테트라메틸부틸퍼옥시-2-에틸헥사노에이트, 2,5-디메틸-2,5-비스(2-에틸헥사노일퍼옥시)헥산, 1-시클로헥실-1-메틸에틸퍼옥시-2-에틸헥사노에이트, t-헥실퍼옥시-2-에틸헥사노에이트, t-부틸퍼옥시-2-에틸헥사노에이트, t-부틸퍼옥시이소부티레이트, 1,1-비스(t-부틸퍼옥시)시클로헥산, t-헥실퍼옥시이소프로필모노카르보네이트, t-부틸퍼옥시-3,5,5-트리메틸헥사노에이트, t-부틸퍼옥시라우레이트, 2,5-디메틸-2,5-비스(m-톨루오일퍼옥시)헥산, t-부틸퍼옥시이소프로필모노카르보네이트, t-부틸퍼옥시-2-에틸헥실모노카르보네이트, t-헥실퍼옥시벤조에이트, t-부틸퍼옥시아세테이트 및 비스(t-부틸퍼옥시)헥사히드로테레프탈레이트를 들 수 있다.Examples of peroxy esters include cumyl peroxyneodecanoate, 1,1,3,3-tetramethyl butyl peroxyneodecanoate, 1-cyclohexyl-1-methyl ethyl peroxyneodecanoate, hexyl peroxyneodecanoate, t-butyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylperoxy) hexane, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t- T-butylperoxyisobutyrate, 1,1-bis (t-butylperoxy) cyclohexane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5 Butyl peroxylaurate, 2,5-dimethyl-2,5-bis (m-toluoylperoxy) hexane, t-butylperoxyisopropyl monocarbonate, t -Butylperoxy-2-ethylhexyl monocarbonate, t-hexyl Peroxybenzoate, may be mentioned t- butylperoxy acetate and bis (t- butylperoxy) hexahydro-terephthalate.
이것들은 1종을 단독으로 또는 2종 이상을 조합하여 사용된다.These may be used singly or in combination of two or more.
기타의 유기 과산화물로서는, 디알킬퍼옥시드, 퍼옥시디카르보네이트, 퍼옥시케탈, 히드로퍼옥시드, 실릴퍼옥시드 등을 들 수 있다. 이들의 유기 과산화물을 상기 디아실퍼옥시드, 퍼옥시에스테르로부터 선택되는 1종 이상과 조합하여, (B) 성분의 유기 과산화물로서 사용할 수도 있다.Examples of other organic peroxides include dialkyl peroxides, peroxydicarbonates, peroxyketals, hydroperoxides, and silyl peroxides. These organic peroxides may be used as organic peroxides of the component (B) in combination with at least one member selected from the above-mentioned diacyl peroxides and peroxy esters.
디알킬퍼옥시드로서는, 예를 들어 α,α'-비스(t-부틸퍼옥시)디이소프로필벤젠, 디쿠밀퍼옥시드, 2,5-디메틸-2,5-비스(t-부틸퍼옥시)헥산 및 t-부틸쿠밀퍼옥시드를 들 수 있다.Examples of the dialkyl peroxide include?,? '-Bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis (t- Hexane and t-butylcumyl peroxide.
퍼옥시디카르보네이트로서는, 예를 들어 디-n-프로필퍼옥시디카르보네이트, 디이소프로필퍼옥시디카르보네이트, 비스(4-t-부틸시클로헥실)퍼옥시디카르보네이트, 디-2-에톡시메톡시퍼옥시디카르보네이트, 비스(2-에틸헥실퍼옥시)디카르보네이트, 디메톡시부틸퍼옥시디카르보네이트 및 비스(3-메틸-3-메톡시부틸 퍼옥시)디카르보네이트를 들 수 있다.Examples of the peroxydicarbonate include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di- Bis (2-ethylhexylperoxy) dicarbonate, dimethoxybutyl peroxydicarbonate and bis (3-methyl-3-methoxybutylperoxy) dicarbonate. .
퍼옥시케탈로서는, 예를 들어 1,1-비스(t-헥실퍼옥시)-3,3,5-트리메틸시클로헥산, 1,1-비스(t-헥실퍼옥시)시클로헥산, 1,1-비스(t-부틸퍼옥시)-3,3,5-트리메틸시클로헥산, 1,1-(t-부틸퍼옥시)시클로도데칸 및 2,2-비스(t-부틸퍼옥시)데칸을 들 수 있다.Examples of peroxyketals include 1,1-bis (t-hexylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) cyclohexane, Bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1- (t-butylperoxy) cyclododecane and 2,2- have.
히드로퍼옥시드로서는, 예를 들어 디이소프로필벤젠히드로퍼옥시드 및 쿠멘히드로퍼옥시드를 들 수 있다.Examples of hydroperoxides include diisopropylbenzene hydroperoxide and cumene hydroperoxide.
실릴퍼옥시드로서는, 예를 들어 t-부틸트리메틸실릴퍼옥시드, 비스(t-부틸)디메틸실릴퍼옥시드, t-부틸트리비닐실릴퍼옥시드, 비스(t-부틸)디비닐실릴퍼옥시드, 트리스(t-부틸)비닐실릴퍼옥시드, t-부틸트리알릴실릴퍼옥시드, 비스(t-부틸)디알릴실릴퍼옥시드 및 트리스(t-부틸)알릴실릴퍼옥시드를 들 수 있다.Examples of the silyl peroxide include t-butyl trimethyl silyl peroxide, bis (t-butyl) dimethyl silyl peroxide, t-butyl trivinyl silyl peroxide, bis (t- t-butyl) vinylsilyl peroxide, t-butyltriallylsilyl peroxide, bis (t-butyl) diallylsilyl peroxide and tris (t-butyl) allylsilyl peroxide.
(B) 성분의 첨가량은, (A) 성분의 오르가노(폴리)실록산 합계량 100질량부에 대하여 0.1 내지 30질량부, 바람직하게는 0.5 내지 20질량부이다. 첨가량이 0.1질량부 미만인 경우, 반응이 충분히 진행되지 않고, 목적으로 하는 경화물의 경도를 얻지 못할 우려가 있다. 30질량부를 초과하는 경우, 원하는 경화 후의 물성, 즉 충분한 내열성, 내광성, 내균열성이 얻어지지 않을 가능성이 있는 것에 더하여, 착색이 발생할 우려가 있어 변색의 원인이 된다. 또한, (B) 성분이 30질량부를 초과하는 경우, 점도가 현저하게 저하되어, 다이 본드재로서 사용이 불가능해질 경우가 있다.The amount of the component (B) to be added is 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass based on 100 parts by mass of the total amount of the organo (poly) siloxane of the component (A). When the addition amount is less than 0.1 part by mass, the reaction does not proceed sufficiently and there is a fear that the desired hardness of the cured product may not be obtained. If it exceeds 30 parts by mass, physical properties after desired curing, that is, sufficient heat resistance, light resistance, and crack resistance may not be obtained, and coloring may occur and cause discoloration. When the amount of the component (B) is more than 30 parts by mass, the viscosity is remarkably lowered, which may render the use as a die-bonding material impossible.
(C) (C) 1분자One molecule 중에 규소 원자에 결합한 수소 원자를 적어도 2개 함유하는 Containing at least two hydrogen atoms bonded to silicon atoms 오르Orc 가노히드로겐폴리실록산The organohydrogenpolysiloxane
(C) 성분의 오르가노히드로겐폴리실록산은, 가교제로서 작용하는 성분이고, (A) 성분과 히드로실릴화 반응을 일으켜, 본 조성물의 경화에 기여한다. 해당 오르가노히드로겐폴리실록산은, 1분자 중에 적어도 2개의 규소 원자 결합 수소 원자(즉, SiH기)를 갖고, 바람직하게는 3 내지 500개, 보다 바람직하게는 3 내지 200개, 특히 바람직하게는 3 내지 150개 갖는다. 1분자 중의 규소 원자수(또는 중합도)는, 바람직하게는 2 내지 200개, 보다 바람직하게는 3 내지 150개의 것이 사용된다. 상기한 SiH기는, 분자쇄 말단 및 분자쇄 비말단 중 어디에 위치하고 있어도 되고, 그의 양쪽에 위치하는 것이어도 된다.The organohydrogenpolysiloxane of the component (C) acts as a crosslinking agent and causes a hydrosilylation reaction with the component (A), thereby contributing to the curing of the composition. The organohydrogenpolysiloxane has at least two silicon atom-bonded hydrogen atoms (i.e., SiH groups) in one molecule, preferably 3 to 500, more preferably 3 to 200, particularly preferably 3 Lt; / RTI > The number of silicon atoms (or degree of polymerization) in one molecule is preferably 2 to 200, more preferably 3 to 150. The above-mentioned SiH group may be located at either the molecular chain terminal or the molecular chain terminal end, or may be located on both sides thereof.
이 오르가노히드로겐폴리실록산 중의 규소 원자에 결합하고 있는 기의 구체예로서는, 예를 들어 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기 등의 알킬기; 시클로펜틸기, 시클로헥실기 등의 시클로알킬기; 페닐기, 톨릴기, 크실릴기 등의 아릴기; 벤질기, 페네틸기 등의 아르알킬기; 3,3,3-트리플루오로프로필기, 3-클로로프로필기 등의 할로겐화 알킬기 등의 지방족 불포화 결합을 갖지 않는, 비치환 또는 치환된 1가 탄화수소기 등을 들 수 있고, 바람직하게는 알킬기 및 아릴기, 특히 바람직하게는, 메틸기 및 페닐기를 들 수 있다.Specific examples of the group bonded to the silicon atom in the organohydrogenpolysiloxane include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group; A cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; Aryl groups such as phenyl, tolyl, and xylyl groups; Aralkyl groups such as a benzyl group and a phenethyl group; An unsubstituted or substituted monovalent hydrocarbon group having no aliphatic unsaturated bond such as a halogenated alkyl group such as a 3,3,3-trifluoropropyl group and a 3-chloropropyl group, and the like, An aryl group, particularly preferably a methyl group and a phenyl group.
(C) 성분의 23℃에서의 점도는 0.5 내지 100,000mPa·s인 것이 바람직하고, 특히 10 내지 5,000mPa·s인 것이 바람직하다. 이러한 오르가노히드로겐폴리실록산의 분자 구조는 한정되지 않고, 예를 들어 직쇄상, 분지쇄상, 일부 분지를 갖는 직쇄상, 환상, 3차원 망상 등을 들 수 있다. 해당 오르가노히드로겐폴리실록산은, 단일종의 실록산 단위를 포함하는 단독 중합체이거나, 2종 이상의 실록산 단위를 포함하는 공중합체이거나, 이들의 혼합물이어도 된다.The viscosity of the component (C) at 23 캜 is preferably from 0.5 to 100,000 mPa · s, more preferably from 10 to 5,000 mPa · s. The molecular structure of such an organohydrogenpolysiloxane is not limited, and examples thereof include linear, branched, partially branched, cyclic, and three-dimensional networks. The organohydrogenpolysiloxane may be a homopolymer containing a single siloxane unit, a copolymer containing two or more siloxane units, or a mixture thereof.
해당 오르가노히드로겐폴리실록산으로서는, 예를 들어 1,1,3,3-테트라메틸디실록산, 1,3,5,7-테트라메틸시클로테트라실록산, 메틸히드로겐실록산 환상 중합체, 메틸히드로겐실록산·디메틸실록산 환상 공중합체, 분자쇄 양쪽 말단 디메틸히드로겐실록시기 봉쇄 디메틸폴리실록산, 분자쇄 양쪽 말단 트리메틸실록시기 봉쇄 메틸히드로겐폴리실록산, 분자쇄 양쪽 말단 트리메틸실록시기 봉쇄 디메틸실록산·메틸히드로겐실록산 공중합체, 분자쇄 양쪽 말단 디메틸히드로겐실록시기 봉쇄 디메틸실록산·메틸히드로겐실록산 공중합체, 양쪽 말단 트리메틸실록시기 봉쇄 메틸히드로겐실록산·디페닐실록산 공중합체, 양쪽 말단 트리메틸실록시기 봉쇄 메틸히드로겐실록산·디페닐실록산·디메틸실록산 공중합체, 양쪽 말단 디메틸히드로겐실록시기 봉쇄 메틸히드로겐실록산·디메틸실록산·디페닐실록산 공중합체, (CH3)2HSiO1 / 2 단위와 (CH3)3SiO1 / 2 단위와 SiO4 / 2 단위를 포함하는 공중합체, (CH3)2HSiO1 / 2 단위와 SiO4/2 단위를 포함하는 공중합체, (CH3)2HSiO1 / 2 단위와 SiO4 / 2 단위와 (C6H5)3SiO1 / 2 단위를 포함하는 공중합체 등을 들 수 있다. 이들 중에서도, 디메틸실록산 단위를 (C) 성분 중의 실록산 단위 전체의 1mol％ 이상 함유하는 것이 바람직하고, 보다 바람직하게는 1 내지 100mol％ 함유하는 것이다.Examples of the organohydrogenpolysiloxane include 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, methylhydrogensiloxane cyclic polymer, methylhydrogen siloxane Dimethylsiloxane cyclic copolymer, molecular chain double terminal dimethylhydrogensiloxy group blocked dimethylpolysiloxane, molecular chain double terminal trimethylsiloxy group blocked methylhydrogenpolysiloxane, molecular chain double terminal trimethylsiloxy group blocked dimethylsiloxane · methylhydrogensiloxane copolymer, Molecular chain double terminal dimethylhydrogensiloxy group blocked dimethylsiloxane · methylhydrogensiloxane copolymer, both terminal trimethylsiloxy group blocked methylhydrogensiloxane · diphenylsiloxane copolymer, both terminal trimethylsiloxy group blocked methylhydrogensiloxane · diphenyl Siloxane-dimethylsiloxane copolymer, double-end dimethylhydrogen siloxane blocker Hydrogen siloxane, dimethylsiloxane-diphenylsiloxane copolymers, (CH 3) 2 HSiO 1/2 units and (CH 3) 3 SiO 1 copolymer containing a / 2 units and SiO 4/2 units, (CH 3) 2 copolymer containing 1 HSiO / 2 units and SiO 4/2 units, (CH 3) 2 HSiO 1 /2 units and SiO 4/2 units and (C 6 H 5) 3 SiO 1/2 containing units Copolymers and the like. Among these, the dimethylsiloxane unit preferably contains 1 mol% or more, more preferably 1 to 100 mol%, of the total siloxane units in the component (C).
본 조성물에 있어서, (C) 성분의 함유량은, (A) 성분 100질량부에 대하여 0.1 내지 20질량부, 바람직하게는 0.5 내지 20질량부, 특히 바람직하게는 1 내지 10질량부이다.In the present composition, the content of the component (C) is 0.1 to 20 parts by mass, preferably 0.5 to 20 parts by mass, particularly preferably 1 to 10 parts by mass with respect to 100 parts by mass of the component (A).
(C) 성분의 함유량이 0.1질량부 미만이면, 본 조성물이 충분히 경화하기 어려워, 경화물 표면이 굳어지지 않을 경우가 일어나 버린다. 20질량부를 초과하면, 본 조성물이 (B) 성분에 의해 경화되지 않게 되어, 퍼옥시드에 의한 경화 성능이 약해져버린다. 또한, 이 (C) 성분의 배합량은, 상기의 이유에 의해, 본 조성물 중의 전체 알케닐기 함유 오르가노(폴리)실록산 중의 규소 원자 결합 알케닐기의 총량에 대한 (C) 성분 중의 규소 원자 결합 수소 원자(즉, SiH기)의 몰비-(A) 성분 이외의 성분이 상기 알케닐기를 갖지 않는 경우에는, (A) 성분 중의 규소 원자 결합 알케닐기에 대한 (B) 성분 중의 규소 원자 결합 수소 원자의 몰비-를 0.01 내지 4.0mol/mol, 바람직하게는 0.05 내지 2.5mol/mol, 특히 바람직하게는 0.1 내지 1.0mol/mol이 되도록 배합할 수도 있다.When the content of the component (C) is less than 0.1 part by mass, the composition is hardly cured sufficiently, and the surface of the cured product is not hardened. When the amount is more than 20 parts by mass, the composition is not cured by the component (B), and the curing performance by the peroxide is weakened. The amount of the component (C) to be added is preferably from 1 to 100 parts by weight, based on the total amount of the silicon atom-bonded alkenyl groups in the total alkenyl group-containing organopolysiloxane (C) (SiH group) - When the component other than the component (A) does not have the alkenyl group, the molar ratio of the silicon atom-bonded hydrogen atoms in the component (B) to the silicon atom-bonded alkenyl group in the component (A) - in the range of 0.01 to 4.0 mol / mol, preferably 0.05 to 2.5 mol / mol, particularly preferably 0.1 to 1.0 mol / mol.
(D) 백금계 촉매(D) a platinum catalyst
(D) 성분의 백금계 촉매는, 본 조성물의 경화를 촉진하기 위한 촉매이고, 예를 들어 백금 및 백금 화합물을 들 수 있고, 구체예로서는 염화백금산, 염화백금산의 알코올 용액, 백금의 올레핀 착체, 백금의 알케닐실록산 착체, 백금의 카르보닐 착체 등을 들 수 있다. 본 조성물에 있어서의 (D) 성분의 함유량은, 유효량이어도 되고, 구체적으로는 (A) 성분에 대하여 (D) 성분 중의 백금 금속 성분이 백금 환산으로서, 질량 기준 0.01 내지 1,000ppm, 바람직하게는 0.1 내지 500ppm이 되는 양이다.The platinum-based catalyst of component (D) is a catalyst for promoting curing of the composition, and examples thereof include platinum and platinum compounds. Specific examples thereof include chloroplatinic acid, an alcoholic solution of chloroplatinic acid, platinum- An alkenylsiloxane complex of platinum, and a carbonyl complex of platinum. The content of the component (D) in the composition may be an effective amount. Specifically, the content of the platinum metal component in the component (D) in terms of platinum relative to the component (A) is 0.01 to 1,000 ppm, preferably 0.1 To 500 ppm.
그 밖의 성분Other components
본 발명의 가열 경화형 실리콘 조성물은, 특정한 용도에 있어서 원하는 것과 같은 경화 또는 미경화 특성을 개변시키는 다른 성분도 포함시킬 수 있다. 예를 들어, (메트)아크릴옥시프로필트리메톡시실란, 트리알킬- 또는 트리알릴-이소시아누레이트, 글리시독시프로필트리메톡시실란, 비닐트리메톡시실란 등과 같은 접착 촉진제를, 약 20질량％까지의 양으로 포함시킬 수 있다. 다른 임의 성분으로서는, 약 30질량％까지의 양의 비(非)(메트)아크릴 실리콘 희석제 또는 가소제를 포함시킬 수 있다. 비(메트)아크릴 실리콘류로서는, 100 내지 500csp의 점도를 갖는 트리메틸실릴 말단화 오일 및 실리콘 고무를 들 수 있다. 비(메트)아크릴 실리콘류는, 비닐기와 같은 공경화성기를 포함할 수 있다.The heat curable silicone composition of the present invention may also include other components that modify the curing or uncured properties such as desired for a particular application. For example, an adhesion promoter, such as (meth) acryloxypropyltrimethoxysilane, trialkyl- or triallyl-isocyanurate, glycidoxypropyltrimethoxysilane, vinyltrimethoxysilane, etc., %. ≪ / RTI > Other optional components may include non-(meth) acrylic silicone diluents or plasticizers in an amount up to about 30% by weight. Examples of the non-meth (acrylate) acrylics include trimethylsilyl-terminated oils and silicone rubbers having a viscosity of 100 to 500 csp. The non-(meth) acrylsilicone species may include a pseudo-mercapto group such as a vinyl group.
또한, 본 발명의 가열 경화형 실리콘 조성물의 강도를 향상, 점도 조정, 틱소트로픽성 부여 등을 목적으로서, 또한 퓸드 실리카, 나노 알루미나 등의 무기질 충전제를 배합해도 된다. 필요에 따라, 본 발명의 가열 경화형 실리콘 조성물에, 염료, 안료, 난연제 등을 배합해도 된다.An inorganic filler such as fumed silica or nano alumina may also be added for the purpose of improving the strength, adjusting the viscosity, imparting thixotropic properties, etc. of the heat curable silicone composition of the present invention. If necessary, dyes, pigments, flame retardants and the like may be added to the heat curable silicone composition of the present invention.
또한, 작업성을 개선하는 목적으로 용제 등을 첨가하여 사용하는 것도 가능하다. 용제의 종류는 특별히 제한되는 것은 아니고, 경화 전의 가열 경화형 실리콘 조성물을 용해하고, 상기 무기질 충전제 등을 양호하게 분산시켜, 균일한 다이 본드재 또는 접착제 등을 제공할 수 있는 용제를 사용할 수 있다. 해당 용제의 배합 비율은 다이 본드재 등을 사용하는 작업 조건, 환경, 사용 시간 등에 따라서 적절히 조정하면 된다. 용제는 2종 이상을 병용해도 된다. 이러한 용제로서는, 부틸카르비톨아세테이트, 카르비톨아세테이트, 메틸에틸케톤, α-테르피네올 및 셀로솔브아세테이트 등을 들 수 있다.It is also possible to add a solvent or the like for the purpose of improving workability. The type of the solvent is not particularly limited, and a solvent capable of dissolving the heat curable silicone composition before curing and dispersing the inorganic filler and the like in a uniform manner and providing a uniform die-bonding material or an adhesive can be used. The compounding ratio of the solvent may be suitably adjusted in accordance with working conditions using a die bond material, environment, use time, and the like. Two or more kinds of solvents may be used in combination. Examples of such solvents include butyl carbitol acetate, carbitol acetate, methyl ethyl ketone,? -Terpineol, and cellosolve acetate.
또한, 본 발명의 조성물에는, 접착성 향상제를 배합해도 된다. 접착성 향상제로서는, 실란 커플링제나 그의 올리고머, 실란 커플링제와 동일한 반응성 기를 갖는 실리콘 등이 예시된다.The composition of the present invention may also contain an adhesion improver. Examples of the adhesiveness improver include silane coupling agents, oligomers thereof, and silicon having the same reactive groups as those of the silane coupling agent.
접착성 향상제로서는, 분자 내에 1개 이상의 에폭시 함유기를 갖는 실란 화합물 또는 실록산 화합물이 바람직하다. 예를 들어, 에폭시기를 함유하는 실란 커플링제나 그의 가수분해 축합물 등이 예시된다. 에폭시기를 함유하는 실란 커플링제나 그의 가수분해 축합물로서는, 글리시독시프로필트리메톡시실란, 글리시독시프로필트리에톡시실란 등의 실란 화합물이나 그의 가수분해 축합물 등을 들 수 있다.As the adhesiveness improver, a silane compound or siloxane compound having at least one epoxy-containing group in the molecule is preferable. For example, a silane coupling agent containing an epoxy group, a hydrolytic condensation product thereof and the like can be given. Examples of silane coupling agents containing epoxy groups and hydrolytic condensates thereof include silane compounds such as glycidoxypropyltrimethoxysilane and glycidoxypropyltriethoxysilane, and hydrolytic condensation products thereof.
접착성 향상제는, 본 발명의 가열 경화형 실리콘 조성물 및 그의 경화물의 기재에 대한 접착성을 향상시키기 위하여 해당 조성물에 배합되는 임의적 성분이다. 여기서, 기재란 금, 은, 구리, 니켈 등의 금속 재료, 산화알루미늄, 질화알루미늄, 산화티타늄 등의 세라믹 재료, 실리콘 수지, 에폭시 수지 등의 고분자 재료를 가리킨다. 접착성 향상제는, 1종 단독으로도 2종 이상을 조합해도 사용할 수 있다.The adhesiveness improver is an optional component incorporated in the composition to improve the adhesion of the heat curable silicone composition of the present invention and the cured product thereof to the substrate. Here, the reference characters refer to metal materials such as gold, silver, copper, and nickel, ceramic materials such as aluminum oxide, aluminum nitride, and titanium oxide, and silicone resins and epoxy resins. The adhesiveness improver may be used alone or in combination of two or more.
접착성 향상제의 배합량은, 상기 (A) 성분과 (B)의 합계 100질량부에 대하여, 바람직하게는 1 내지 30질량부이고, 보다 바람직하게는 5 내지 20질량부이다. 해당 배합량이 5 내지 20질량부이면, 본 발명의 가열 경화형 실리콘 조성물 및 그의 경화물은, 기재에 대한 접착성이 효과적으로 향상되고, 또한 착색되기 어렵다.The blending amount of the adhesion improver is preferably 1 to 30 parts by mass, and more preferably 5 to 20 parts by mass based on the total 100 parts by mass of the components (A) and (B). When the blending amount is in the range of 5 to 20 parts by mass, the heat curable silicone composition of the present invention and the cured product thereof are improved in adhesion to the substrate effectively and hardly colored.
접착성 향상제의 적합한 구체예로서는, 하기를 들 수 있지만, 이들에 한정되는 것은 아니다.Suitable specific examples of the adhesiveness improver include, but are not limited to, the following.
(a, r은 0 내지 50의 정수, b, s, t는 1 내지 50의 정수임)(a, r is an integer of 0 to 50, b, s, and t are integers of 1 to 50)
또한, 가용 시간을 확보하기 위해서, 3-메틸-1-도데신-3-올, 1-에티닐시클로헥산올, 3,5-디메틸-1-헥신-3-올 등의 부가 반응 제어제를 배합할 수 있다.In order to secure an available time, an addition reaction control agent such as 3-methyl-1-dodecin-3-ol, 1-ethynylcyclohexanol or 3,5- Can be compounded.
경화물의 착색, 산화 열화 등의 발생을 억제하기 위해서, 2,6-디-t-부틸-4-메틸페놀 등의 종래 공지된 산화 방지제를 본 발명의 가열 경화형 실리콘 조성물에 배합할 수 있다. 또한, 광 열화에 대한 저항성을 부여하기 위해서, 힌더드 아민계 안정제 등의 광 안정제를 본 발명의 가열 경화형 실리콘 조성물에 배합할 수도 있다.A conventionally known antioxidant such as 2,6-di-t-butyl-4-methylphenol and the like can be incorporated in the heat curable silicone composition of the present invention in order to suppress the occurrence of coloring and oxidation deterioration of the cured product. In order to impart resistance to photo deterioration, a light stabilizer such as a hindered amine stabilizer may be incorporated into the heat curable silicone composition of the present invention.
본 발명의 가열 경화형 실리콘 조성물은, 상기 각 성분을 공지된 혼합 방법, 예를 들어 믹서, 롤 등을 사용하여 혼합함으로써 제조할 수 있다. 또한, 본 발명의 가열 경화형 실리콘 조성물은, 회전 점도계, 예를 들어 E형 점도계를 사용하여 23℃에서 측정한 점도가 10 내지 1,000,000mPa·s, 특히 100 내지 1,000,000mPa·s인 것이 바람직하다.The heat curable silicone composition of the present invention can be produced by mixing the respective components by a known mixing method, for example, using a mixer, a roll, or the like. The heat curable silicone composition of the present invention preferably has a viscosity of 10 to 1,000,000 mPa · s, more preferably 100 to 1,000,000 mPa · s, measured at 23 ° C. using a rotational viscometer, for example, an E-type viscometer.
본 발명의 가열 경화형 실리콘 조성물은, 공지된 경화 조건 하에서 공지된 경화 방법에 의해 경화시킬 수 있다. 구체적으로는, 통상 80 내지 200℃, 바람직하게는 100 내지 160℃에서 가열함으로써, 해당 조성물을 경화시킬 수 있다. 가열 시간은 0.5분 내지 5시간 정도, 특히 1분 내지 3시간 정도가 좋다. 작업 조건, 생산성, 발광 소자 및 하우징 내열성의 밸런스로부터 적절히 선정할 수 있다.The heat curable silicone composition of the present invention can be cured by a known curing method under known curing conditions. Concretely, the composition can be cured by heating at 80 to 200 ° C, preferably 100 to 160 ° C. The heating time is preferably 0.5 minutes to 5 hours, particularly 1 minute to 3 hours. And can be appropriately selected from the balance of working conditions, productivity, light emitting element and heat resistance of the housing.
본 발명의 가열 경화형 실리콘 조성물은, (메트)아크릴기의, 퍼옥시드에 의한 경화와, SiH기와 불포화기의 부가 반응의 양쪽의 경화를 행함으로써, 산소 저해에 의한 표면 부분의 미경화를 극복한 경화물을 부여하는 것이 가능하게 된다. 또한, 본 발명의 가열 경화형 실리콘 조성물은, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 부여할 수 있다.The heat curable silicone composition of the present invention is a curable composition obtained by curing both a peroxide-curing (meth) acrylic group and an addition reaction of an SiH group with an unsaturated group by overcoming the non- It becomes possible to give a cured product. Further, the heat curable silicone composition of the present invention can give a cured product excellent in bonding strength and workability, and excellent in heat resistance, light resistance and crack resistance.
또한, 본 발명에서는, 상기 본 발명의 가열 경화형 실리콘 조성물을 포함하는 것인 다이 본드재를 제공한다. 특히, 반도체 소자를 배선판에 접속하기 위하여 사용할 수 있는 다이 본드재를 들 수 있다.Further, the present invention provides a die-bonding material comprising the heat curable silicone composition of the present invention. In particular, a die bond material that can be used for connecting a semiconductor element to a wiring board can be mentioned.
본 발명의 가열 경화형 실리콘 조성물은, LED 칩을 패키지에 고정하기 위하여 적합하게 사용할 수 있다. 또한, 기타 유기 전계 발광 소자(유기 EL), 레이저 다이오드 및 LED 어레이 등의 광반도체 소자에도 적합하게 사용할 수 있다.The heat curable silicone composition of the present invention can be suitably used for fixing the LED chip to a package. In addition, it can be suitably used for optical semiconductor devices such as other organic electroluminescent devices (organic EL), laser diodes and LED arrays.
본 발명의 가열 경화형 실리콘 조성물은, 투명성이 높고, 접착 강도 및 작업성이 우수하고, 또한 내열성, 내광성 및 내균열성이 우수한 경화물을 부여할 수 있다. 따라서, 상기 가열 경화형 실리콘 조성물을 포함하는 다이 본드재라면, LED 칩을 배선판에 탑재하기 위한 다이 본드재로서 적합하게 사용할 수 있다.The heat curable silicone composition of the present invention can give a cured product having high transparency, excellent adhesive strength and workability, and excellent heat resistance, light resistance and crack resistance. Therefore, the die bonding material including the heat curing type silicone composition can be suitably used as a die bonding material for mounting the LED chip on the wiring board.
다이 본드재를 도포하는 방법은 특별히 제한되지 않고, 예를 들어 스핀 코팅, 인쇄 및 압축 성형 등을 들 수 있다. 다이 본드재의 두께는 적절히 선택하면 되고, 통상 5 내지 50㎛, 특히 10 내지 30㎛이다. 예를 들어, 디스펜스 장치를 사용하여 23℃의 온도, 0.5 내지 5kgf/㎠의 압력으로 토출함으로써 용이하게 도포를 할 수 있다. 또한, 스탬핑 장치를 사용함으로써 소정 양의 다이 본드재를 기판에 전사함으로써도 용이하게 할 수 있다.The method of applying the die bond material is not particularly limited, and examples thereof include spin coating, printing and compression molding. The thickness of the die-bonding material is appropriately selected, and is usually 5 to 50 占 퐉, particularly 10 to 30 占 퐉. For example, the dispenser can be easily applied by discharging at a temperature of 23 캜 and a pressure of 0.5 to 5 kgf /
광반도체 소자의 탑재 방법은 특별히 제한되지 않고, 예를 들어 다이 본더를 들 수 있다. 다이 본드재의 두께를 결정하는 요소는, 전술한 다이 본드재의 점도에 더하여, 광반도체 소자의 압착 하중, 압착 시간, 압착 온도를 들 수 있다. 이들 조건은, 광반도체 소자의 외형 형상, 목적으로 하는 다이 본드재 두께에 따라서 적절히 선택하면 되고, 압착 하중은 일반적으로 1gf 이상 1kgf 이하이다. 바람직하게는 10gf 이상 100gf 이하이다. 1gf 이상의 압착 하중이면, 다이 본드재를 충분히 압착할 수 있다. 또한 1kgf 이하의 압착 하중을 사용하면, 광반도체 소자 표면의 발광층에 대미지를 주는 일이 없다. 압착 시간은 공정의 생산성과의 균형에서 적절히 선택하면 되고, 일반적으로 0msec를 초과하고 1sec 이하이다. 바람직하게는 1msec 이상 30msec이다. 1sec 이하라면 생산성의 점에서 바람직하다. 압착 온도는 특별히 제한은 없고, 다이 본드재의 사용 온도 범위를 따르면 되지만, 일반적으로 15℃ 이상 100℃ 이하이면 바람직하다. 다이 본더의 압착 스테이지에 가온 설비가 없는 경우에는 실온 부근에서의 온도대에서 사용하면 된다. 15℃ 이상이면, 다이 본드재의 점도가 너무 높아지지 않기 때문에 충분히 압착할 수 있다. 100℃ 이하이면 다이 본드재의 경화가 시작되는 일이 없기 때문에, 목적으로 하는 다이 본드재의 두께에 도달할 수 있다.The mounting method of the optical semiconductor element is not particularly limited, and for example, a die bonder can be mentioned. The factors determining the thickness of the die bond material include, in addition to the viscosity of the die bond material, the compression load, the compression time, and the compression temperature of the optical semiconductor element. These conditions can be appropriately selected according to the outer shape of the optical semiconductor element and the intended thickness of the die bond material, and the compression load is generally 1 gf or more and 1 kgf or less. And preferably 10 gf or more and 100 gf or less. When the bonding load is 1 gf or more, the die bonding material can be sufficiently pressed. In addition, when a compression load of 1 kgf or less is used, there is no damage to the light emitting layer on the surface of the optical semiconductor element. The compression time can be appropriately selected from the balance with the productivity of the process, and generally, it is more than 0 msec and less than 1 second. It is preferably 1 msec or more and 30 msec. If it is 1 sec or less, it is preferable from the viewpoint of productivity. The squeezing temperature is not particularly limited and can be determined according to the use temperature range of the die bond material, but it is generally preferable that the squeezing temperature is not less than 15 ° C and not more than 100 ° C. In the case where there is no heating facility on the compression bonding stage of the die bonder, it may be used at a temperature near the room temperature. If it is 15 DEG C or more, the viscosity of the die bonding material is not too high, so that it can be sufficiently pressed. If the temperature is lower than 100 占 폚, hardening of the die bond material does not start, and the thickness of the intended die bond material can be reached.
또한 본 발명에서는, 상기 본 발명의 다이 본드재를 경화하여 얻어지는 경화물을 갖는 것인 광반도체 장치를 제공한다.The present invention also provides an optical semiconductor device having a cured product obtained by curing the die bonding material of the present invention.
본 발명의 광반도체 장치는, 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 경화하여 얻어지는 경화물을 갖기 때문에, 표면 부분의 미경화를 극복한 내열성, 내광성 및 내균열성이 우수한 경화물을 갖는 광반도체 장치가 된다.Since the optical semiconductor device of the present invention has a cured product obtained by curing a die bond material containing the heat curable silicone composition of the present invention, it is possible to provide a cured product having superior heat resistance, light resistance and crack resistance As shown in Fig.
본 발명의 광반도체 장치는, 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 기판에 도포한 후, 종래 공지된 방법에 따라 광반도체 소자를 다이 본딩함으로써 제조할 수 있다.The optical semiconductor device of the present invention can be manufactured by applying a die bonding material containing the heat curable silicone composition of the present invention to a substrate and then die bonding the optical semiconductor device according to a conventionally known method.
이하, 본 발명의 광반도체 장치의 일 형태에 대하여 도면을 참조하여 설명한다. 도 1은, 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 경화하여 얻어지는 경화물을 갖는 광반도체 장치의 일례를 도시하는 단면도이다. 도 1에 도시하는 광반도체 장치(10)는, 패키지 기판의 하우징(1)의 제1 리드 전극(3) 상에 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 경화하여 얻어지는 경화물(5)을 갖고, 이 경화물(5) 상에 광반도체 소자(2)가 탑재된 것이다. 이 광반도체 소자(2)의 전극은, 금선(6)에 의해 제1 리드 전극(3)과 전기적으로 접속되어 있다. 또한, 이 광반도체 소자(2)의 전극은, 금선(7)에 의해 제2 리드 전극(4)과 전기적으로 접속되어 있다. 또한, 이 광반도체 소자(2)는, 밀봉 수지(8)로 밀봉되어 있다.Hereinafter, one embodiment of the optical semiconductor device of the present invention will be described with reference to the drawings. 1 is a cross-sectional view showing an example of a photosemiconductor device having a cured product obtained by curing a die bond material containing the heat curable silicone composition of the present invention. The
도 1의 광반도체 장치(10)의 제조 방법으로서는, 이하의 방법을 예시할 수 있다.As a manufacturing method of the
먼저, 패키지 기판의 하우징(1)의 제1 리드 전극(3) 상에, 본 발명의 가열 경화형 실리콘 조성물을 포함하는 다이 본드재를 정량 전사하고, 그 위에 광반도체 소자(2)를 탑재한다. 이어서, 다이 본드재를 가열 경화시켜서 경화물(5)로 한다. 이어서, 광반도체 소자(2)의 전극과 제1 리드 전극(3)을 금선(6)을 사용하여 전기적으로 접속하고, 광반도체 소자(2)의 전극과 제2 리드 전극(4)을 금선(7)을 사용하여 전기적으로 접속하여, 광반도체 소자(2)가 탑재된 패키지 기판을 얻는다. 계속해서, 밀봉 수지(8)를 정량 도포하고, 도포된 밀봉 수지를 공지된 경화 조건 하에서 공지된 경화 방법에 의해, 경화시킴으로써 패키지 기판을 밀봉할 수 있다. 본 발명의 다이 본드재를 경화하여 얻어지는 경화물을 갖는 광반도체 디바이스로서는, 예를 들어 LED, 반도체 레이저, 포토다이오드, 포토 트랜지스터, 태양 전지, CCD 등을 들 수 있다.First, a die bonding material containing the heat curable silicone composition of the present invention is quantitatively transferred onto the first
[실시예][Example]
이하에 실시예와 비교예를 나타내어, 본 발명을 구체적으로 설명하지만, 본 발명은 하기의 실시예에 한정되는 것은 아니다.EXAMPLES Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples.
(실시예 1 내지 8, 비교예 1 내지 5)(Examples 1 to 8 and Comparative Examples 1 to 5)
하기 성분을 준비하여, 표 1, 2에 나타내는 조성의 실리콘 조성물을 제조하였다.The following components were prepared, and silicon compositions having the compositions shown in Tables 1 and 2 were prepared.
(A-1)(A-1)
하기 실록산 단위를 포함하고,Comprising the following siloxane units,
MA:M:Q=1:4:6의 비율로, 분자량이 GPC에 의한 폴리스티렌 환산의 중량 평균 분자량으로 5,000이고, 25℃에서 고체인 오르가노폴리실록산A weight average molecular weight of 5,000 in terms of polystyrene by GPC and a molecular weight of 5,000 and a solid at 25 DEG C in the ratio of MA: M: Q = 1: 4: 6
(A-2)(A-2)
하기 화학식으로 표시되는, 25℃에서의 점도가 7mPa·s인 오르가노실록산An organosiloxane having a viscosity at 25 캜 of 7 mPa 하기, represented by the following formula:
(B-1)(B-1)
디아실퍼옥시드로서 디-(3-메틸벤조일)페록사이드[Di-(3-methylbenzoyl)peroxide], 벤조일(3-메틸벤조일)페록사이드[Benzoyl(3-methylbenzoyl)peroxide] 및 디벤졸 페록사이드(Dibenzol peroxide)의 40％ 크실렌 용액(상품명: 나이퍼 BMT-K40, 니혼 유시 가부시끼가이샤제)을 그대로 사용하였다.(3-methylbenzoyl) peroxide], benzoyl (3-methylbenzoyl) peroxide, and dibenzoyl peroxide as diacyl peroxides 40% xylene solution of dibenzol peroxide (trade name: NIPPER BMT-K40, manufactured by Nippon Yushi Kabushiki Kaisha) was used as it was.
(B-2)(B-2)
퍼옥시에스테르로서 t-부틸 페록시벤조에이트(t-Butyl peroxybenzoate)(상품명: 퍼부틸 Z, 니혼 유시 가부시끼가이샤제)를 그대로 사용하였다.T-Butyl peroxybenzoate (trade name: perbutyl Z, manufactured by Nippon Yushi Kabushiki Kaisha) was used as the peroxy ester.
(C) 가교제(C) Crosslinking agent
하기 실록산 단위를 포함하고,Comprising the following siloxane units,
M: (CH3)3SiO1 /2 M: (CH 3) 3 SiO 1/2
D: (CH3)2SiO2 /2 D: (CH 3) 2 SiO 2/2
DH: (CH3)SiHO2 /2 DH: (CH 3) SiHO 2 /2
M:D:DH=2:32:66으로 표시되는, 25℃에서의 점도가 150mPa·s인 직쇄상 오르가노폴리실록산A linear organopolysiloxane having a viscosity at 25 캜 of 150 mPa 표시, represented by M: D: DH = 2: 32: 66
(D) 백금계 촉매:(D) Platinum catalyst:
백금 함유량이 0.5질량％의 백금 1,3-디비닐-1,1,3,3-테트라메틸디실록산 착체의 톨루엔 용액A toluene solution of a platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex having a platinum content of 0.5% by mass
기타 임의 성분Other optional ingredients
점도 조정제: 퓸드 실리카(상품명 레오실롤 DM-30S 토쿠야마사제)Viscosity adjusting agent: Fumed silica (trade name: Leothylol DM-30S, Tokuyama)
접착성 향상제: 측쇄에 에폭시기를 함유하는 환상 실리콘 오일(상품명: X-40-2670, 신에쯔 가가꾸 고교 가부시끼가이샤제)Adhesion improver: cyclic silicone oil (trade name: X-40-2670, manufactured by Shin-Etsu Chemical Co., Ltd.) containing an epoxy group in the side chain,
반응 제어제: 3-메틸-1-도데신-3-올Reaction control agent: 3-methyl-1-dodecin-3-ol
[경도의 측정][Measurement of hardness]
얻어진 조성물을 2mm 두께의 셀에 유입하고, 150℃×2시간의 조건에서 경화하고, 경화물을 제조하였다. 그 후, 우에지마 세이사쿠쇼제 듀로미터 타입 D에 의해 경도를 측정하였다.The composition thus obtained was introduced into a cell having a thickness of 2 mm and cured under the conditions of 150 占 폚 for 2 hours to prepare a cured product. Thereafter, the hardness was measured by Durometer Type D manufactured by Ueshima Seisakusho Co., Ltd.
[표면 태크의 평가][Evaluation of Surface Tack]
얻어진 조성물을 알루미늄 샤알레에 유입하고, 150℃×2시간의 조건에서 대기 하에서 경화하고, 경화물을 제조하였다. 얻어진 경화물의 표면 태크를 지촉으로 평가하였다.The obtained composition was introduced into an aluminum shale and cured under the conditions of 150 占 폚 for 2 hours to prepare a cured product. The surface tack of the obtained cured product was evaluated by touching.
[광반도체 패키지의 제조][Production of optical semiconductor package]
LED용 패키지 기판으로서, 광반도체 소자를 적재하는 오목부를 갖고, 그 저부에 은 도금된 제1 리드 전극과 제2 리드 전극이 설치된 LED용 패키지 기판[SMD5050(I-CHIUN PRECISION INDUSTRY CO., 회사제, 수지부 PPA(폴리프탈아미드))], 광반도체 소자로서, Bridgelux사제 BXCD33을, 각각 준비하였다.As a package substrate for LED, a package substrate for LED [SMD5050 (I-CHIUN PRECISION INDUSTRY CO., LTD., Manufactured by I-CHI PRECISION INDUSTRY CO., LTD.) Having concave portions for mounting optical semiconductor elements and having first and second lead electrodes, , Resin PPA (polyphthalamide))], and BXCD33 manufactured by Bridgelux Co., Ltd. as optical semiconductor devices.
다이 본더(ASM사제 AD-830)를 사용하여, 패키지 기판의 은 도금된 제1 리드 전극에, 표 1, 2에 나타내는 각 조성물을 스탬핑에 의해 정량 전사하고, 그 위에 광반도체 소자를 탑재하였다. 이때의 광반도체 소자의 탑재 조건은, 압착 시간 13msec, 압착 하중 60gf이고, 가온 장치를 사용하지 않고 실온 25℃의 환경에서 행하였다. 이어서, 패키지 기판을 오븐에 투입하고 각 다이 본드재를 가열 경화시켰다(실시예 1 내지 8, 비교예 2 및 비교예 4는 150℃, 4시간, 비교예 1은 170℃, 1시간). 이어서, 광반도체 소자의 전극과 제1 리드 전극을 금 와이어(다나카 덴시 고교사제 FA 25㎛)를 사용하여 전기적으로 접속하고, 광반도체 소자의 전극과 제2 리드 전극을 금 와이어(다나카 덴시 고교사제 FA 25㎛)를 사용하여 전기적으로 접속하였다. 이에 의해, 광반도체 소자가 탑재된 LED용 패키지 기판 각 1매(패키지수로서 120개)을 얻었다.Using the die bonder (AD-830 manufactured by ASM Corporation), the compositions shown in Tables 1 and 2 were quantitatively transferred to the silver plated first lead electrodes of the package substrate by stamping, and the optical semiconductor elements were mounted thereon. The mounting condition of the optical semiconductor element at this time was a compression time of 13 msec and a compression load of 60 gf, and was performed in an environment of a room temperature of 25 캜 without using a heating device. Subsequently, the package substrate was placed in an oven, and each of the die-bonding materials was heat-cured. (Examples 1 to 8, Comparative Examples 2 and 4 were heated at 150 DEG C for 4 hours and Comparative Example 1 at 170 DEG C for 1 hour). Then, the electrode of the optical semiconductor element and the first lead electrode were electrically connected using a gold wire (FA 25 mu m manufactured by Tanaka Denshi Co., Ltd.), and the electrode of the optical semiconductor element and the second lead electrode were connected to a gold wire FA 25 mu m). As a result, one piece of each LED package substrate on which the optical semiconductor element was mounted (120 packages) was obtained.
상기와 같이 하여, 다이 본드재가 다른 광반도체 패키지를 제조하여, 이하의 시험에 사용하였다.As described above, optical semiconductor packages different from the die bonding material were produced and used in the following tests.
[다이 시어 시험][Daisha test]
상기의 방법으로 얻어진 광반도체 패키지 중 10개를, 25℃의 실내에서 본드 테스터(Dage사제 Series4000)를 사용하여 다이 시어 강도의 측정을 행하고, 얻어진 측정값의 평균값을 MPa로 나타내었다.Ten of the optical semiconductor packages obtained by the above method were subjected to measurement of die shear strength using a bond tester (Series4000 manufactured by Dage Co.) in a room at 25 캜, and the average value of measured results obtained was expressed in MPa.
[산소에 의한 표면 경화 저해의 평가][Evaluation of inhibition of surface hardening by oxygen]
상기의 방법으로 얻어진 광반도체 패키지에 있어서, 25℃의 실내에서, 선단이 뾰족한 바늘로 칩 주변을 문지르고, 산소에 의한 표면 경화 저해의 유무를 확인하였다.In the optical semiconductor package obtained by the above-described method, around the chip was rubbed with a sharp-pointed needle at room temperature of 25 캜 to confirm whether or not the surface hardening was inhibited by oxygen.
얻어진 결과를 표 3, 4에 나타내었다.The obtained results are shown in Tables 3 and 4.
표 3에 나타낸 바와 같이, 본 발명의 범위를 충족하는 가열 경화형 실리콘 조성물을 다이 본드재로서 사용한 실시예 1 내지 실시예 8에서는, 모두 고경도이고 또한 표면 태크가 없는, 산소 저해에 의한 표면 부분의 미경화를 극복한 경화물이 얻어졌다. 또한, 다이 시어 측정의 결과, 접착력이 높고 신뢰성이 높은 광반도체 디바이스를 제조할 수 있는 것을 알 수 있었다.As shown in Table 3, in Examples 1 to 8, in which the heat curable silicone composition satisfying the range of the present invention was used as a die bonding material, all of the surface portions due to oxygen inhibition having high hardness and no surface tack A cured product overcome the uncured state was obtained. Further, as a result of the die-free measurement, it was found that an optical semiconductor device with high adhesive strength and high reliability can be manufactured.
한편, C, D 성분을 포함하지 않는 비교예 1, 2에서는 모두 고경도이며 또한 높은 다이 시어가 관측되었지만, 표면 태크가 있고, 산소에 의한 표면 경화 저해가 확인되었다. 또한, 비교예 2로부터 명백해진 바와 같이, 이 표면 경화 저해는 퍼옥시드의 양을 증가시켰다고 해도 방지할 수 없었다. B 성분의 양이 과잉인 경우(비교예 3), 점도가 현저하게 저하되고, 스탬핑을 할 수 없게 되었다. 또한, C 성분이 과잉인 경우(비교예 4), 산소에 의한 표면 경화 저해는 방지할 수 있었지만 다이 시어가 저하되는 결과가 되었다. B 성분을 포함하지 않고, 백금 촉매만으로 경화시킨 비교예 5에서는 경도가 현저하게 저하되고, 또한 점도의 상승에 의해 스탬핑 불능이 되었다.On the other hand, in Comparative Examples 1 and 2 which did not contain the C and D components, both hardness and high degree of diaer were observed, but there was surface tack and inhibition of surface hardening by oxygen was confirmed. In addition, as apparent from Comparative Example 2, this surface hardening inhibition could not be prevented even if the amount of peroxide was increased. When the amount of the B component was excessive (Comparative Example 3), the viscosity was remarkably lowered and the stamping could not be performed. Further, in the case where the C component was excessive (Comparative Example 4), inhibition of the surface hardening by oxygen could be prevented, but the result was that the diacer was lowered. In Comparative Example 5 in which the B component was not cured and only the platinum catalyst was cured, the hardness was remarkably lowered and the stamping became impossible due to the increase of the viscosity.
또한, 본 발명은 상기 실시 형태에 한정되는 것은 아니다. 상기 실시 형태는 예시이고, 본 발명의 특허청구범위에 기재된 기술적 사상과 실질적으로 동일한 구성을 갖고, 동일한 작용 효과를 발휘하는 것은, 어떠한 것이어도 본 발명의 기술적 범위에 함유된다.The present invention is not limited to the above-described embodiments. The foregoing embodiments are illustrative and any of those having substantially the same structure as the technical idea described in the claims of the present invention and exhibiting the same operational effects are included in the technical scope of the present invention.
1…하우징, 2…광반도체 소자, 3…제1 리드 전극, 4…제2 리드 전극, 5…다이 본드재(경화물), 6, 7…금선, 8…밀봉 수지, 10…광반도체 장치.One… Housing, 2 ... Optical semiconductor device, 3 ... The first lead electrode, the fourth lead electrode, The second lead electrode, 5 ... Die bond material (cured), 6, 7 ... Gold wire, 8 ... Sealing resin, 10 ... Optical semiconductor device.
Claims (6)
[식 중, m은 0, 1, 2 중 어느 것이고, R1은 수소 원자, 페닐기 또는 할로겐화 페닐기, R2는 수소 원자 또는 메틸기, R3은 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 12의 1가의 유기기, Z1은 -R4-, -R4-O-, -R4(CH3)2Si-O-(R4는 치환 또는 비치환으로 동일 또는 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기) 중 어느 것, Z2는 산소 원자 또는 치환 혹은 비치환으로 동일 혹은 상이해도 되는 탄소 원자수 1 내지 10의 2가의 유기기임]
(B) 디아실퍼옥시드, 퍼옥시에스테르로부터 선택되는 1종 이상을 포함하는 유기 과산화물: 0.1 내지 30질량부,
(C) 1분자 중에 규소 원자에 결합한 수소 원자를 적어도 2개 함유하는 오르가노히드로겐폴리실록산: 0.1 내지 20질량부,
(D) 백금계 촉매: (A) 성분에 대하여 (D) 성분 중의 백금 질량 환산으로 0.01 내지 1,000ppm이 되는 양
을 함유하는 것을 특징으로 하는 가열 경화형 실리콘 조성물.(A) 100 parts by mass of an organo (poly) siloxane having at least one structure represented by the following general formula (1) in a molecule,
R 2 is a hydrogen atom or a methyl group, R 3 is a substituted or unsubstituted, or the same or different, the number of carbon atoms which may be the same or different, and m is 0 or 1 or 2; R 1 is a hydrogen atom, a phenyl group or a halogenated phenyl group; 1 to 12, Z 1 represents -R 4 -, -R 4 -O-, -R 4 (CH 3 ) 2 Si-O- (wherein R 4 may be substituted or unsubstituted, And Z 2 is an oxygen atom or a divalent organic group having 1 to 10 carbon atoms which may be the same or different and are substituted or unsubstituted,
(B) 0.1 to 30 parts by mass of an organic peroxide containing at least one selected from diacyl peroxide and peroxy ester,
(C) 0.1 to 20 parts by mass of an organohydrogenpolysiloxane containing at least two hydrogen atoms bonded to silicon atoms in one molecule,
(D) Platinum-based catalyst: The amount of the platinum-based catalyst is 0.01 to 1,000 ppm in terms of platinum mass in the component (D)
Wherein the thermosetting silicone composition is a thermosetting silicone composition.
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