KR20100060143A - Photocurable silicon resin for sealing of electric device - Google Patents
Photocurable silicon resin for sealing of electric device Download PDFInfo
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- KR20100060143A KR20100060143A KR1020080118607A KR20080118607A KR20100060143A KR 20100060143 A KR20100060143 A KR 20100060143A KR 1020080118607 A KR1020080118607 A KR 1020080118607A KR 20080118607 A KR20080118607 A KR 20080118607A KR 20100060143 A KR20100060143 A KR 20100060143A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- aryl
- alkoxy
- heteroaryl
- photocurable
- Prior art date
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- 238000007789 sealing Methods 0.000 title claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 7
- 239000010703 silicon Substances 0.000 title claims abstract description 7
- 229920005989 resin Polymers 0.000 title abstract description 5
- 239000011347 resin Substances 0.000 title abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- -1 arly Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 13
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920002050 silicone resin Polymers 0.000 claims description 34
- 239000011342 resin composition Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000007822 coupling agent Substances 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 3
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052863 mullite Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- WTQHTDIBYAAFEX-UHFFFAOYSA-N 1-decylsulfonylsulfonyldecane Chemical compound CCCCCCCCCCS(=O)(=O)S(=O)(=O)CCCCCCCCCC WTQHTDIBYAAFEX-UHFFFAOYSA-N 0.000 claims description 2
- LOZJPUXMNANKIQ-UHFFFAOYSA-N 2-benzyl-3-nitro-4-(nitromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C[N+]([O-])=O)C([N+]([O-])=O)=C1CC1=CC=CC=C1 LOZJPUXMNANKIQ-UHFFFAOYSA-N 0.000 claims description 2
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 claims description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 2
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 claims description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 239000012953 triphenylsulfonium Substances 0.000 claims description 2
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 claims description 2
- WBUSZOLVSDXDOC-UHFFFAOYSA-M (4-methoxyphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WBUSZOLVSDXDOC-UHFFFAOYSA-M 0.000 claims 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims 1
- DRMAIBPBPJNFDH-UHFFFAOYSA-M [4-(2-methylpropyl)phenyl]-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(CC(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 DRMAIBPBPJNFDH-UHFFFAOYSA-M 0.000 claims 1
- 229940000489 arsenate Drugs 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 230000006750 UV protection Effects 0.000 abstract description 6
- 238000004383 yellowing Methods 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 230000001939 inductive effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 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 3
- 230000035699 permeability Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- JNDMLEXHDPKVFC-UHFFFAOYSA-N aluminum;oxygen(2-);yttrium(3+) Chemical compound [O-2].[O-2].[O-2].[Al+3].[Y+3] JNDMLEXHDPKVFC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 229910019901 yttrium aluminum garnet Inorganic materials 0.000 description 2
- VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 description 1
- LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LXAWHMFHGHNIHC-UHFFFAOYSA-N sulfanyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OS LXAWHMFHGHNIHC-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Silicon Polymers (AREA)
Abstract
Description
본 발명은 전기소자, 특히 LED의 봉지에 유용한 광경화형 실리콘 수지에 관한 것으로서, 본 발명에 따른 광경화형 실리콘 수지를 포함하는 수지 조성물은 광개시제를 함유하지 않고도 광경화가 가능하여 우수한 투명성, 내열성 및 내UV특성을 나타낼 수 있다.The present invention relates to a photocurable silicone resin useful for encapsulating electric devices, particularly LEDs, wherein the resin composition comprising the photocurable silicone resin according to the present invention is photocurable without containing a photoinitiator, thereby providing excellent transparency, heat resistance and UV resistance. Can exhibit characteristics.
광 및 전자소자를 봉지함에 있어서 적용되는 조성물은 광 투과특성은 물론 내열성, 내UV특성 및 접착성이 우수해야 하며, 소자의 열화를 방지하기 위하여 수분투과특성이 낮아야 한다.The composition to be applied in encapsulating the optical and electronic devices should be excellent in heat transmission, UV resistance and adhesion as well as light transmission properties, and low moisture permeation properties in order to prevent deterioration of the device.
이러한 특성을 만족시키는 조성물로서, 현재 에폭시 수지가 가장 널리 사용되고 있다. 에폭시 수지는 접착성이 우수하고 제조가 용이하며, 공정성이 우수하여 LED 봉지제를 비롯한 각종 전자소자의 봉지제로 적용되고 있다. 또한, 열 및 광에 의해 경화가 가능하여 전자소자의 제작시 다양한 공정에 적용이 가능한 것이 특징이다. 하지만, 에폭시 수지는 고온에 오래 방치되거나 UV에 오래 노출될 경우 갈색 으로 변하는 단점이 있고, 수분투과특성이 만족스럽지 않아 열 및 수분에 취약한 전자소자에 있어서 높은 수명을 확보하는데 그 한계를 드러내는 것이 사실이다.As a composition that satisfies these properties, epoxy resins are most widely used at present. Epoxy resins have excellent adhesiveness, are easy to manufacture, and have excellent processability, and have been applied as encapsulants for various electronic devices including LED encapsulation agents. In addition, it is possible to be cured by heat and light is characterized in that it can be applied to a variety of processes in the manufacture of electronic devices. However, epoxy resins have a disadvantage that they turn brown when exposed to high temperatures or exposed to UV for a long time, and exhibits limitations in securing high lifetime in electronic devices vulnerable to heat and moisture due to unsatisfactory moisture permeability. to be.
이를 보완하기 위해, 최근 실리콘 수지에 대한 연구가 활발히 진행 중에 있다. 실리콘 수지는 투명성과 내열성, 내UV성이 우수하여, 실리콘 수지를 각종 광학소자 및 디스플레이용 재료로 사용하기 위한 연구가 진행되고 있다. 하지만, 실리콘 수지의 경우 계면 특성이 에폭시 수지보다 좋지 못하여 계면에서의 박리 및 접착강도 특성이 낮아서, 실리콘 수지의 측쇄에 에폭시기를 도입하여 이를 개선하려는 노력이 진행되고 있다. 또한, 실리콘 수지의 구조적 특성으로 인해 수지의 주쇄를 3차원 그물망 모양 및 사다리 모양 등으로 자유롭게 디자인 할 수 있기 때문에, 실리콘 수지는 다양한 특성을 구현해 낼 수 있는 장점 또한 갖는다.In order to compensate for this, research on silicone resins is actively underway. Silicone resins are excellent in transparency, heat resistance, and UV resistance, and research for using silicone resins in various optical devices and displays is being conducted. However, in the case of the silicone resin, the interfacial properties are not as good as the epoxy resin, so the peeling and adhesive strength characteristics at the interface are low, and efforts have been made to improve this by introducing an epoxy group into the side chain of the silicone resin. In addition, the silicone resin has the advantage of realizing a variety of properties because the structural properties of the silicone resin can freely design the main chain of the resin in a three-dimensional mesh shape and ladder shape.
하지만, 이러한 장점에도 불구하고, 실리콘 수지를 광경화 반응을 통해 경화시킬 경우 광개시제가 반드시 첨가되어야 하는데, 이렇게 첨가되는 광개시제는 경화반응이 진행될 때 황변현상을 일으키는 주된 원인이 되고 있다.However, in spite of these advantages, a photoinitiator must be added when the silicone resin is cured through a photocuring reaction, and the photoinitiator thus added is a major cause of yellowing when the curing reaction proceeds.
따라서 본 발명의 목적은 광개시제의 첨가 없이도 광경화 반응을 유도함으로써 광개시제의 사용으로 인한 황변현상을 획기적으로 차단하고 우수한 투명성, 내열성 및 내UV특성을 나타낼 수 있는, 전기소자 봉지용 광경화형 실리콘 소자를 제공하는 것이다.Accordingly, an object of the present invention is to induce a photocuring reaction without the addition of a photoinitiator, thereby significantly blocking the yellowing phenomenon caused by the use of the photoinitiator and can exhibit excellent transparency, heat resistance and UV resistance, photo-curable silicon device for sealing an electrical device To provide.
상기 목적을 달성하기 위해 본 발명은,In order to achieve the above object,
하기 화학식 1 내지 3 중 어느 하나의 구조로 표시되는, 전기소자 봉지용 광경화형 실리콘 수지를 제공한다:Provided is a photocurable silicone resin for sealing an electrical device, represented by the structure of any one of the following Chemical Formulas 1 to 3:
[화학식 1][Formula 1]
[화학식 2][Formula 2]
[화학식 3](3)
상기 식에서,Where
R은 각각 독립적으로 
여기서 R1은 각각 독립적으로 C1-30 알킬, C1-30 알킬 에스터, C1-30 알콕시, C1-30 알킬카보닐, C6-20 아릴, C6-20 헤테로아릴 또는 할로겐이 치환된 C1-30 알킬, C1-30 알킬 에스터, C1-30 알콕시, C1-30 알킬카보닐, C6-20 아릴, C6-20 헤테로아릴이고;Wherein R 1 is each independently substituted with C 1-30 alkyl, C 1-30 alkyl ester, C 1-30 alkoxy, C 1-30 alkylcarbonyl, C 6-20 aryl, C 6-20 heteroaryl or halogen C 1-30 alkyl, C 1-30 alkyl ester, C 1-30 alkoxy, C 1-30 alkylcarbonyl, C 6-20 aryl, C 6-20 heteroaryl;
A는 각각 독립적으로 C1-30 알킬, C1-30 알콕시, 할로겐, 아미드, 시아노, 하이드록시, 니트로, 아실, C6-20 아릴 또는 C6-20 헤테로아릴로 치환되거나 치환되지 않은, C1-30 알킬, C1-30 알콕시, C6-20 아릴 또는 C6-20 헤테로아릴이며;Each A is independently substituted or unsubstituted with C 1-30 alkyl, C 1-30 alkoxy, halogen, amide, cyano, hydroxy, nitro, acyl, C 6-20 aryl or C 6-20 heteroaryl, C 1-30 alkyl, C 1-30 alkoxy, C 6-20 aryl or C 6-20 heteroaryl;
R3는 각각 독립적으로 방향족 고리 화합물, 아릴 또는 헤테로 아릴이다.Each R 3 is independently an aromatic ring compound, aryl or hetero aryl.
본 발명의 광경화형 실리콘 수지는 광개시제의 첨가 없이도 광경화 반응을 유도할 수 있어 황변현상을 획기적으로 차단하고 우수한 투명성, 내열성, 수분투과특성 및 내UV특성을 나타낼 수 있으며, 광개시제 등의 첨가제를 필요로 하지 않음으로써 상분리 등의 불안정성을 차단할 수 있다. 또한, 광경화 반응으로 인해 전자소자의 제작에 있어서 공정시간을 단축시킬 수 있고, 안정된 저장 안정성으로 인해 본 발명의 실리콘 수지를 포함하는 수지 조성물의 저장 수명(pot life) 또한 증대시킬 수 있다.The photocurable silicone resin of the present invention can induce a photocuring reaction without the addition of a photoinitiator, thereby significantly blocking yellowing and exhibiting excellent transparency, heat resistance, moisture permeability and UV resistance, and require an additive such as a photoinitiator. By not doing so, instability such as phase separation can be prevented. In addition, the photocuring reaction can shorten the process time in the manufacture of electronic devices, and can also increase the pot life of the resin composition comprising the silicone resin of the present invention due to stable storage stability.
본 발명은 광경화 반응에 있어서 2+2 사이클로 첨가(cyclo addition)반응을 하는 치환기 R(예를 들어 칼콘(chalcone) 또는 신나모일(cinnamoyl)기-함유 치환기)이, 실리콘을 기반으로 한 광경화형 수지(실세스퀴옥산(silsesquioxane))의 측쇄에 도입되어 황변현상의 주된 원인으로 지적되는 광개시제를 첨가하지 않고도 광경화가 가능한 상기 화학식 1 내지 3의 광경화형 실리콘 수지를 제공하는 것을 특징으로 한다.In the present invention, the substituent R (for example, a chalcone or cinnamoyl group-containing substituent), which undergoes a cycloaddition reaction in a photocuring reaction, is based on silicon. It is characterized by providing a photocurable silicone resin of the above formulas (1) to (3) which can be photocured without adding a photoinitiator, which is introduced into the side chain of a resin (silsesquioxane) and indicated as the main cause of yellowing.
상기 치환기 R은 바람직하게는 
여기서 R1은 각각 독립적으로 C1-30 알킬, C1-30 알킬 에스터, C1-30 알콕시, C1-30 알킬카보닐, C6-20 아릴, C6-20 헤테로아릴 또는 할로겐이 치환된 C1-30 알킬, C1-30 알킬 에스터, C1-30 알콕시, C1-30 알킬카보닐, C6-20 아릴, C6-20 헤테로아릴이고;Wherein R 1 is each independently substituted with C 1-30 alkyl, C 1-30 alkyl ester, C 1-30 alkoxy, C 1-30 alkylcarbonyl, C 6-20 aryl, C 6-20 heteroaryl or halogen C 1-30 alkyl, C 1-30 alkyl ester, C 1-30 alkoxy, C 1-30 alkylcarbonyl, C 6-20 aryl, C 6-20 heteroaryl;
R2는 각각 독립적으로 수소, C1-30 알킬, C1-30 알콕시, 할로겐, 아미드, 시아노, 하이드록시, 니트로, 아실, C6-20 아릴 또는 C6-20 헤테로아릴로 치환되거나 치환되지 않은, C1-30 알킬, C1-30 알콕시, C6-20 아릴 또는 C6-20 헤테로아릴이며, 이들은 서로 환을 형성될 수 있다.Each R 2 is independently substituted or substituted with hydrogen, C 1-30 alkyl, C 1-30 alkoxy, halogen, amide, cyano, hydroxy, nitro, acyl, C 6-20 aryl or C 6-20 heteroaryl Or C 1-30 alkyl, C 1-30 alkoxy, C 6-20 aryl or C 6-20 heteroaryl, which may form a ring with each other.
본 발명에 따른 화학식 1 내지 3의 실리콘 수지가 UV 조사될 경우 치환기 R은 예를 들어 하기 반응식 1에 나타낸 바와 같은 2+2 사이클로 첨가반응을 일으키며, 이로써 본 발명의 실리콘 수지는 광개시제 없이도 광경화 반응을 수행할 수 있다:When the silicone resin of Formulas 1 to 3 according to the present invention is irradiated with UV, substituent R causes an addition reaction in 2 + 2 cycles, for example, as shown in Scheme 1 below, whereby the silicone resin of the present invention is a photocuring reaction without a photoinitiator. You can do this:
[반응식 1]Scheme 1
본 발명에 따른 실리콘 수지는, 화학식 1 내지 3 중 어느 하나의 구조로 표시되는 화합물에 있어서 R이 수소원자인 경우의 화합물(하기 화학식 4 내지 6의 화합물)을 하기 화학식 7 또는 화학식 8의 화합물과 바람직하게는 백금 촉매 존재하에 반응시켜 제조할 수 있다:The silicone resin according to the present invention is a compound represented by the structure of any one of formulas 1 to 3 when R is a hydrogen atom (compounds of formulas 4 to 6) and the compound of formula 7 or Preferably produced by reaction in the presence of a platinum catalyst:
[화학식 4][Formula 4]
[화학식 5][Chemical Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8] [Formula 8]
상기 식에서,Where
R1은 각각 독립적으로 말단에 이중결합을 갖는 C2-30 알킬, C2-30 알킬에스터, C2-30 알콕시, C2-30 알킬카보닐 또는 말단에 할로겐 원소를 갖는 C1-30 알킬, C1-30 알킬에스터, C1-30 알콕시, C1-30 알킬카보닐 또는 할로겐이 치환된 C6-20 아릴 또는 C6-20 헤테로 아릴이고, A, R3는 각각 독립적으로 상기에서 정의한 바와 같다. 바람직하기로는 상기 R3는 C1-30 알킬, C1-30 알콕시, 할로겐, 아미드, 시아노, 하이드록시, 니트로, 아실, C6-20 아릴 또는 C6-20 헤테로아릴로 치환되거나 치환되지 않은 C6-30 의 방향족 고리화합물 또는 아릴이다.Each R 1 is independently C 2-30 alkyl, C 2-30 alkylester, C 2-30 alkoxy, C 2-30 alkylcarbonyl having a double bond at the end or C 1-30 alkyl having a halogen element at the end , C 1-30 alkylester, C 1-30 alkoxy, C 1-30 alkylcarbonyl or C 6-20 aryl substituted with halogen or C 6-20 heteroaryl, A, R 3 are each independently As defined. Preferably, R 3 is substituted or unsubstituted with C 1-30 alkyl, C 1-30 alkoxy, halogen, amide, cyano, hydroxy, nitro, acyl, C 6-20 aryl or C 6-20 heteroaryl C 6-30 aromatic cyclic compound or aryl.
출발물질로 사용되는 상기 화학식 4 내지 6의 화합물, 화학식 7 및 화학식 8의 화합물은 통상적인 방법으로 제조할 수 있다.The compounds of Formulas 4 to 6, and the compounds of Formulas 7 and 8 used as starting materials may be prepared by conventional methods.
또한, 본 발명은, 상기 화학식 1 내지 3 중 어느 하나의 구조로 표시되는 광경화형 실리콘 수지를 포함하는 광경화형 수지 조성물을 제공한다.In addition, the present invention provides a photocurable resin composition comprising a photocurable silicone resin represented by the structure of any one of the formulas (1) to (3).
본 발명에 사용되는 광경화형 수지 조성물은 (1) 실리콘 수지 50~90 중량%, (2) 무기충진제 1~40 중량% 및 (3) 커플링제 0.1~10 중량%를 포함하는 것이 바람직하며, 선택적으로 (4) 스페이서 1~20 중량%, (5) 광산발생제 0.001~1 중량% 또는 (6) 형광체 0.01 내지 5 중량%를 더 함유할 수 있다. 이때 본 발명의 광경화형 수지 조성물은 광개시제를 포함하지 않는다.The photocurable resin composition used in the present invention comprises (1) 50 to 90% by weight of a silicone resin, (2) 1 to 40% by weight of inorganic filler and (3) 0.1 to 10% by weight of coupling agent, optionally (4) 1 to 20% by weight of spacer, (5) 0.001 to 1% by weight of photoacid generator % Or (6) phosphor may further contain 0.01 to 5% by weight. At this time, the photocurable resin composition of this invention does not contain a photoinitiator.
바람직하게는 본 발명의 광경화형 수지 조성물은 5,000~150,000 cps를 가지는 것이 좋다.Preferably, the photocurable resin composition of the present invention preferably has 5,000 to 150,000 cps.
(1) 실리콘 수지(1) silicone resin
본 발명에 따른 상기 화학식 1 내지 3 중 어느 하나의 구조로 표시되는 광경화형 실리콘 수지 또는 이들의 혼합물을 사용한다.Photocurable silicone resins or mixtures thereof represented by the structure of any one of the above Chemical Formulas 1 to 3 according to the present invention are used.
(2) 무기충진제(2) inorganic fillers
본 발명의 광경화형 수지 조성물에 적용 가능한 무기충진제로는 활석(talc), 실리카, 산화마그네슘, 마이카(mica), 몬모릴로나이트, 알루미나, 그라파이트, 베릴리라(beryllium oxide), 질화알루미늄, 탄화규소, 멀라이트(mullite), 실리콘 등의 판상 또는 구형의 무기충진제, 또는 상기 무기충진제에 치환기를 도입한 지름 또는 장축이 0.1 내지 20 um인 무기충진제를 사용할 수 있다. 수지 조성물에 첨가되는 무기충진제는 경화 후 조성물의 내부에 고르게 분산되어, 조성물에 작용하는 응력을 분산시켜 접착력을 강화시켜 줄 뿐만 아니라, 조성물 내부로 침투하여 확산되는 수분을 효과적으로 막아주어 수분투과특성을 향상시켜주는 효과가 있다.Inorganic fillers applicable to the photocurable resin composition of the present invention include talc, silica, magnesium oxide, mica, montmorillonite, alumina, graphite, beryllium oxide, aluminum nitride, silicon carbide, and mullite. (mullite), a plate-like or spherical inorganic filler such as silicon, or an inorganic filler having a diameter or long axis of 0.1 to 20 um having a substituent introduced therein may be used. Inorganic fillers added to the resin composition are evenly dispersed in the composition after curing to disperse the stress acting on the composition to enhance adhesion, as well as effectively prevent moisture from penetrating into the composition to diffuse moisture permeability. It has the effect of improving.
(3) 커플링제(3) coupling agent
본 발명의 광경화형 수지 조성물에 적용 가능한 커플링제는 실란계 또는 티탄계 커플링제, 실리콘 화합물을 단독 또는 혼합하여 사용할 수 있다. 바람직하게는, 한 분자 내에 알콕시실란과 디글리시딜에테르를 함유하고 있는 실란 커플링제가 좋다. The coupling agent applicable to the photocurable resin composition of this invention can use a silane type or titanium type coupling agent, and a silicone compound individually or in mixture. Preferably, a silane coupling agent containing alkoxysilane and diglycidyl ether in one molecule is preferable.
(4) 스페이서(4) spacer
본 발명의 광경화형 수지 조성물에 적용 가능한 스페이서로는 경화 후 패널의 두께를 일정하게 유지시켜줄 수 있는 것이라면 특별히 한정되지 않으며, 패널의 두께를 5~50 um, 바람직하게는 5~25 um로 유지할 수 있는 것이 좋다. 스페이서의 모양은 구형, 통나무형 등이 있으며, 스페이서의 모양 역시 패널의 두께를 일정하게 유지시킬 수 있는 것이면 특별히 한정되지 않는다.The spacer applicable to the photocurable resin composition of the present invention is not particularly limited as long as it can maintain the thickness of the panel after curing, and the thickness of the panel can be maintained at 5 to 50 um, preferably 5 to 25 um. It is good to be. The shape of the spacer is spherical, log, and the like, and the shape of the spacer is not particularly limited as long as the thickness of the panel can be kept constant.
(5) 광산발생제(5) photoacid generator
본 발명의 광경화형 수지 조성물에 적용 가능한 광산발생제로는 노광에 의해 루이스산 또는 브론스테드산을 생성시킬 수 있는 것이면 특별히 한정되지 않으며, 유기술폰산 등의 황화염계 화합물, 오니움염 등의 오니움계 화합물을 사용할 수 있다. 바람직하게는, 프탈이미도트리플루오로메탄술포네이트, 디니트로벤질토실레이트, n-데실디술폰, 나프틸이미도트리플루오로메탄술포네이트, 디페닐요도염, 헥사플루오로포스페이트, 디페닐요도염, 헥사플루오로아르세네이트, 디페닐요도염, 헥 사플루오로안티모네이트, 디페닐파라메톡시페닐설포늄 트리플레이트, 디페닐파라톨루에닐설포늄 트리플레이트, 디페닐파라이소부틸페닐설포늄 트리플레이트, 트리페닐설포늄 헥사플루오로 아르세네이트, 트리페닐설포늄 헥사플루오로 안티모네이트, 트리페닐설포늄 트리플레이트, 디부틸나프틸설포늄 트리플레이트 및 이들의 혼합물을 사용할 수 있다.The photoacid generator which can be applied to the photocurable resin composition of the present invention is not particularly limited as long as it can generate Lewis acid or Bronsted acid by exposure, and is based on sulfur compounds such as sulfuric acid compounds such as euphonic acid and onium salts. Compounds can be used. Preferably, phthalimido trifluoromethanesulfonate, dinitrobenzyltosylate, n-decyldisulfone, naphthylimidotrifluoromethanesulfonate, diphenyl iodo salt, hexafluorophosphate, diphenyl iodo salt, hexafluoro Roarsenate, diphenyl iodo salt, hexafluoroantimonate, diphenyl paramethoxyphenylsulfonium triflate, diphenyl paratoluenylsulfonium triflate, diphenyl paraisobutylphenyl sulfonium triflate, tri Phenylsulfonium hexafluoro arsenate, triphenylsulfonium hexafluoro antimonate, triphenylsulfonium triflate, dibutylnaphthylsulfonium triflate and mixtures thereof can be used.
(6) 형광체(6) phosphor
형광체는 칩에서 발생되는 광에너지 여기에 의해 자체 발광을 한다. 구체적인 예로 LED용 형광체로는 LED칩에서 발산하는 청색의 빛을 흡수하여 녹색, 황색, 적색의 빛을 발산하는 형광체를 사용할 수 있으며, 바람직하기로는 상기 형광체가 무기화합물로 무정형의 입자이며 크기는 입경이 1-100 um인 것이 좋으며, LED에서 대표적인 것으로 이트륨 알루미늄 가넷(YAG)을 사용할 수 있다.The phosphor emits light by self-excited light energy generated from the chip. As a specific example, the phosphor for LED may use a phosphor that absorbs blue light emitted from the LED chip and emits light of green, yellow, and red. Preferably, the phosphor is an amorphous compound with a particle size and a particle size. The 1-100um is preferable, and yttrium aluminum garnet (YAG) can be used as a typical LED.
상술한 바와 같은 본 발명의 광경화형 수지 조성물을 사용하여 통상적인 방법으로 전기소자, 특히 LED의 봉지를 수행할 수 있으며, 본 발명의 수지 조성물로 봉지된 전기소자는 우수한 수명 특성을 나타낼 수 있다. Using the photocurable resin composition of the present invention as described above, it is possible to perform the encapsulation of the electric element, in particular LED, by a conventional method, the electric element encapsulated with the resin composition of the present invention can exhibit excellent life characteristics.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
[실시예]EXAMPLE
실시예 1 : 화합물 4의 합성Example 1 Synthesis of Compound 4
4-하이드록시벤즈알데하이드 122.12g, 아세토페논 120.15g, 소디움 에톡사이드 81.66g 및 에탄올 1리터를 환류냉각기가 설치된 2리터 둥근 바닥 플라스크에 첨가하고 80도에서 24시간 동안 환류교반 시켰다. 24시간 후 염산 수용액으로 중화처리를 하고 감압필터를 한 후, 에탄올로 3~5차례 세척하여 194g의 화합물 4를 합성하였다.122.12 g of 4-hydroxybenzaldehyde, 120.15 g of acetophenone, 81.66 g of sodium ethoxide and 1 liter of ethanol were added to a 2-liter round bottom flask equipped with a reflux condenser and stirred at reflux at 80 degrees for 24 hours. After 24 hours, the mixture was neutralized with aqueous hydrochloric acid, filtered under reduced pressure, and washed 3 times with ethanol to synthesize 194 g of Compound 4.
[화학식 4][Formula 4]
(R : H) (R: H)
실시예 2 : 화합물 7a의 합성Example 2 Synthesis of Compound 7a
하기 화학식 8의 화합물 146.075g, 5-브로모-1-펜텐 89.418g, 포타슘 카보네이트 83g 및 DMF 1리터를 환류냉각기가 설치된 2리터 둥근 바닥 플라스크에 첨가하고 90도에서 12시간동안 환류교반 시켰다. 12시간 후 추출 및 컬럼 크로마토그래피를 이용하여 정제하여 120g의 화합물 7a를 합성하였다 (하기 반응식 2 참조).146.075 g of the compound of Formula 8, 89.418 g of 5-bromo-1-pentene, 83 g of potassium carbonate, and 1 liter of DMF were added to a 2-liter round bottom flask equipped with a reflux condenser and stirred at reflux for 90 hours at 12 ° C. After 12 hours, 120 g of Compound 7a was synthesized by extraction and column chromatography (see Scheme 2 below).
[반응식 2]Scheme 2
실시예 3 : 화합물 2a(본 발명의 실리콘 수지)의 합성Example 3: Synthesis of Compound 2a (Silicone Resin of the Invention)
상기 실시예 1에서 합성된 화합물 4 106.2g, 상기 실시예 2에서 합성된 화합물 7a 642.3g 및 톨루엔 1리터를 환류냉각기가 설치된 2리터 둥근 바닥 플라스크에 첨가하고, 60도까지 승온시킨 후 Pt(dvs) 촉매 6ml를 주사기를 이용하여 적하한 후, 4시간동안 교반시켰다. 4시간 후 플래시 크로마토그래피법을 이용하여 백금 촉매를 제거하고 감압증류하여 톨루엔을 제거함으로써 700g의 화합물 2a(실리콘 수지)를 합성하였다 (하기 반응식 3 참조).106.2 g of compound 4 synthesized in Example 1, 642.3 g of compound 7a synthesized in Example 2, and 1 liter of toluene were added to a 2-liter round bottom flask equipped with a reflux condenser, and heated to 60 degrees, followed by Pt (dvs 6 ml of the catalyst was added dropwise using a syringe, followed by stirring for 4 hours. After 4 hours, 700 g of Compound 2a (silicone resin) was synthesized by removing the platinum catalyst using flash chromatography and distilling under reduced pressure to remove toluene (see Scheme 3 below).
[반응식 3]Scheme 3
시험예 : UV 조사에 따른 실리콘 수지의 변화 측정Test Example: Measurement of Change of Silicone Resin According to UV Irradiation
상기 실시예 3에서 합성된 실리콘 수지에 대해서 3분 동안 UV 조사한 결과 그 치환기 R은 상기 반응식 1에 나타낸 바와 같이 2+2 사이클로 첨가반응을 일으켰으며, 이로써 본 발명의 실리콘 수지가 광개시제 없이도 광경화 반응을 수행할 수 있음을 알 수 있다.UV irradiation was performed for 3 minutes on the silicone resin synthesized in Example 3, and the substituent R caused an addition reaction in 2 + 2 cycles as shown in Scheme 1, whereby the silicone resin of the present invention was photocured without a photoinitiator. It can be seen that can be performed.
Claims (12)
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014092267A1 (en) * | 2012-12-12 | 2014-06-19 | 제일모직 주식회사 | Photocurable composition, barrier layer comprising same, and encapsulated apparatus comprising same |
| WO2014208849A1 (en) * | 2013-06-27 | 2014-12-31 | 제일모직 주식회사 | Photocurable composition and encapsualted device including same |
| KR20150001581A (en) * | 2013-06-27 | 2015-01-06 | 제일모직주식회사 | Photocurable composition and encapsulated apparatus comprising the same |
| CN116574384A (en) * | 2023-07-12 | 2023-08-11 | 北京智慧能源研究院 | Silicon gel insulating material for packaging silicon carbide power device and application thereof |
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2008
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014092267A1 (en) * | 2012-12-12 | 2014-06-19 | 제일모직 주식회사 | Photocurable composition, barrier layer comprising same, and encapsulated apparatus comprising same |
| WO2014208849A1 (en) * | 2013-06-27 | 2014-12-31 | 제일모직 주식회사 | Photocurable composition and encapsualted device including same |
| KR20150001581A (en) * | 2013-06-27 | 2015-01-06 | 제일모직주식회사 | Photocurable composition and encapsulated apparatus comprising the same |
| CN105143316A (en) * | 2013-06-27 | 2015-12-09 | 第一毛织株式会社 | Photocurable composition and encapsualted device including same |
| CN116574384A (en) * | 2023-07-12 | 2023-08-11 | 北京智慧能源研究院 | Silicon gel insulating material for packaging silicon carbide power device and application thereof |
| CN116574384B (en) * | 2023-07-12 | 2023-10-03 | 北京智慧能源研究院 | Silicon gel insulating material for packaging silicon carbide power device and application thereof |
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