WO2014133287A1 - 광학소자 봉지용 수지 조성물 - Google Patents
광학소자 봉지용 수지 조성물 Download PDFInfo
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- WO2014133287A1 WO2014133287A1 PCT/KR2014/001458 KR2014001458W WO2014133287A1 WO 2014133287 A1 WO2014133287 A1 WO 2014133287A1 KR 2014001458 W KR2014001458 W KR 2014001458W WO 2014133287 A1 WO2014133287 A1 WO 2014133287A1
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- Prior art keywords
- formula
- resin composition
- optical element
- compound
- encapsulating
- Prior art date
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- 230000003287 optical effect Effects 0.000 title claims abstract description 63
- 239000011342 resin composition Substances 0.000 title claims abstract description 38
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229920001709 polysilazane Polymers 0.000 claims abstract description 39
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 39
- 238000005538 encapsulation Methods 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000007789 sealing Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000004888 barrier function Effects 0.000 abstract description 12
- 238000004132 cross linking Methods 0.000 abstract description 8
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 238000010943 off-gassing Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 15
- 230000008569 process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000002834 transmittance Methods 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 5
- -1 poly (phenylvinyl Chemical group 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FWSPXZXVNVQHIF-UHFFFAOYSA-N triethyl(ethynyl)silane Chemical compound CC[Si](CC)(CC)C#C FWSPXZXVNVQHIF-UHFFFAOYSA-N 0.000 description 2
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QFGKJHGPIVNQPI-UHFFFAOYSA-N C[SiH](C)OC1=CC=CC=C1 Chemical compound C[SiH](C)OC1=CC=CC=C1 QFGKJHGPIVNQPI-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
-
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/62—Nitrogen atoms
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side 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
Definitions
- the present invention relates to a thermosetting resin composition for encapsulating an optical device, and more particularly, polyhedral oligomeric silsesquioxane (POSS) and organic polysilazane (crosslinkable) to increase compatibility with the resin.
- the present invention relates to a resin composition for encapsulating an optical device, including a polysilazane) compound, having excellent mechanical properties and improved adhesion to a substrate and a barrier property against moisture or oxygen.
- Organic materials included in optical devices such as OLEDs and LCDs are very vulnerable to oxygen or water vapor in the air, and thus, when exposed to oxygen or water vapor, output reduction or premature performance degradation may occur. Accordingly, a method for extending the life of the device by protecting the devices using metal and glass has been developed, but metals generally have a disadvantage of lack of transparency and glass lack of flexibility.
- a flexible barrier film or encapsulant composition having flexibility has been developed for encapsulation of thin, light and flexible flexible OLEDs and other optical devices, and particularly silicone-based polymers having excellent light resistance and light transmittance. Compounds have been continuously preferred and developed as encapsulants in optical devices.
- silsesquioxane used is a powder type having a mixture of a ladder and a cage structure, and thus is a solvent-free process. It was unsuitable for most optical elements, especially LED encapsulation materials, which require a type.
- the present invention uses a modified silsesquioxane and organic polysilazane to increase the compatibility with the resin, can be manufactured in a solvent-free type and can reduce the outgas optical device encapsulation
- An object of the present invention is to provide a resin composition for sealing and an optical element sealing method using the same.
- the present invention to achieve the above object
- Each R is independently a compound of formula 3-1 or 3-2:
- R 1 to R 6 are each independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl or aryl having 6 to 50 carbon atoms;
- Each Ra is independently hydrogen or chlorine
- z is an integer of 3 to 20, preferably an integer of 5 to 20 ;
- a and b are each independently an integer of 0 to 20, wherein a + b is an integer of 3 to 20,
- M, Ma and Mb are each independently methyl or phenyl
- R X and R Y are each independently alkyl, alkenyl or aryl having 6 to 50 carbon atoms, preferably methyl, ethyl, vinyl or phenyl, more preferably R X is methyl, ethyl or Phenyl and R Y is methyl, ethyl or vinyl;
- n and n are each independently an integer of 1 to 20, wherein m + n is 2 to 21.
- the present invention provides a method for encapsulating an optical device using a sealing composition
- optical device encapsulation method using the optical device encapsulation composition.
- the present invention provides an optical element encapsulation film made of the optical element encapsulation composition.
- the resin composition for encapsulating the optical device of the present invention includes a polyhedral oligomeric silsesquioxane (POSS) having increased compatibility with the resin due to crosslinking, thereby improving solubility with the siloxane resin, thereby allowing a solvent-free process. Therefore, the encapsulation process characteristics are excellent, the crosslinking density is improved, and the mechanical characteristics are excellent.
- the resin composition of the present invention can be thermally cured by including an organic polysilazane compound and a modified polysilazane compound, and greatly reduces the outgas phenomenon by removing unreacted monomers that cause outgass through such a process. Since it can improve, a barrier characteristic can be improved significantly.
- the resin composition for encapsulating the optical element of the present invention can be used as a solvent-free process, and thus may be usefully used as an optical element, in particular, an LED encapsulation composition.
- the present invention can also be applied to a thick film encapsulation step.
- the resin composition for encapsulating the optical device of the present invention is characterized in that it comprises a polyhedral oligomeric silsesquioxane (POSS) and an organic polysilazane compound which can be crosslinked to increase compatibility with the resin.
- PES polyhedral oligomeric silsesquioxane
- organic polysilazane compound which can be crosslinked to increase compatibility with the resin.
- Cage-type polyhedral oligomeric silsesquioxanes commonly used in the art have a compatibility with the siloxane resins used as the main resin when used in the resin composition for encapsulation because the synthetic product thereof is in powder form. It is not good and it is not suitable for the resin composition for encapsulation, and since it melt
- composition of the present invention comprises a polyhedral oligomeric silsesquioxane of formula 1-1 or 1-2 in order to increase the compatibility with the siloxane resin:
- Each R is independently a compound of formula 3-1 or 3-2:
- R 1 to R 6 are each independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl or aryl having 6 to 50 carbon atoms, preferably hydrogen, methyl, ethyl, vinyl or phenyl, and more preferably R 1 is Hydrogen or methyl, R 2 is methyl or phenyl, R 3 is hydrogen, methyl or phenyl, R 4 is hydrogen, methyl or vinyl, R 5 is methyl, vinyl or phenyl, R 6 is methyl, ethyl or methyl ego;
- Each Ra is independently hydrogen or chlorine
- z is an integer of 3 to 20, preferably an integer of 5 to 20 ;
- a and b are each independently an integer of 0 to 20, wherein a + b is an integer of 3 to 20,
- M, Ma and Mb are each independently methyl or phenyl.
- the compound of Formula 1-1 or 1-2 is mainly based on the compound of Formula 3-1, the compound of Formula 3-2, the compound of Formula 3-3, or the following Formulas 3-4 and 3-5
- Compounds can be synthesized via condensation on distilled water with reactants:
- R 1 to R 6 , z, a and b are as defined above;
- Ra and R 7 are each independently hydrogen or chlorine
- x and y are each independently an integer of 1-100.
- the polyhedral oligomeric silsesquioxane usable in the present invention not only has sufficient compatibility with the siloxane resin even without dissolving in an organic solvent, but also includes a crosslinkable moiety, thereby improving the crosslinking density and mechanical properties of the resin composition. It can improve and also help to improve the gas barrier properties.
- the polyhedral oligomeric silsesquioxane may be used in an amount of 1 to 20% by weight based on the total composition, and when the content exceeds the content, compatibility with the siloxane resin may be reduced.
- composition of the present invention also comprises an organic polysilazane of formula (2) to remove outgas phenomena that lower barrier properties:
- R X and R Y are each independently alkyl, alkenyl or aryl having 6 to 50 carbon atoms, preferably methyl, ethyl, vinyl or phenyl, more preferably R X is methyl, ethyl or Phenyl and R Y is methyl, ethyl or vinyl;
- n and n are each independently an integer of 1 to 20, wherein m + n is 2 to 21.
- the organic polysilazane compound usable in the present invention is a compound which can be thermally cured, and when the vacuum / heat compounding process is applied to a resin composition for encapsulation containing the organic polysilazane compound, Outgassing can be improved by removing unreacted monomers. Therefore, when the composition of the present invention containing the organic polysilazane can be used to produce an encapsulation film having excellent surface properties, it can be applied to the encapsulation process of a thick film of several ⁇ m to several mm.
- the organic polysilazane compound may be used in an amount of 0.1 to 10% by weight based on the total composition.
- the organic polysilazane compound exceeds the content, the outgas phenomenon may be deepened and the barrier property may be reduced.
- composition of the present invention may further include a modified polysilazane compound of formula 4 to improve the barrier properties by improving the outgas phenomenon:
- Ra is alkyl of 1 to 20 carbon atoms or aryl of 6 to 50 carbon atoms
- Rb is a hydrocarbon of 1 to 20 carbon atoms, preferably a hydrocarbon of 1 to 5 carbon atoms;
- p is an integer from 1 to 15.
- the compound of Formula 4 may be synthesized through solution polymerization based on the compound of Formula 4-1 and the compound of Formula 4-3, or the compound of Formula 4-2 and compound of Formula 4-3 Can:
- R c is hydrogen or chlorine
- R d , R e and R f are each independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl or aryl having 6 to 50 carbon atoms.
- the modified polysilazane compound may be used in an amount of 0.1 to 15% by weight based on the total composition.
- the outgas phenomenon may be intensified to reduce barrier properties.
- the resin composition for encapsulating the optical device of the present invention may include a siloxane resin, a crosslinking resin, a silane coupling agent, and the like, which are commonly used in conventional amounts.
- the composition of the present invention may further include the modified polysilazane.
- the composition may further include a catalyst or a reaction retardant.
- the composition of the present invention is 1 to 20% by weight of the polyhedral oligomeric silsesquioxane, 0.1 to 10% by weight of the organic polysilazane, 30 to 85% by weight of the siloxane resin based on the total composition %, 5 to 40% by weight of crosslinked resin, and 0.05 to 10% by weight of silane coupling agent.
- the composition may comprise 0.1 to 15% by weight of the modified polysilazane siloxane resin, more preferably the composition may further comprise 1 to 3000 ppm of catalyst or 1 to 1000 ppm of reaction retardant. have.
- the siloxane resins usable in the present invention include polymethylvinyl siloxane, poly (methylphenyl) hydrosiloxane, poly (methylphenyl) siloxane, poly (phenylvinyl) -co- (methylvinyl) silsesquioxane, PDV-1635 from gelest, PMV-9925, PVV-3522, etc. are mentioned, As a crosslinking resin, a silsesquioxane copolymer, a phenylhydro silsesquioxane, or dimethyl silyl phenyl ether, etc. are mentioned, As a silane coupling agent, a methacrylate type
- Cyclosiloxane, etc., and the catalyst may be a platinum catalyst
- the reaction retardant may be ethynyl trimethyl silane or ethynyl triethyl silane and the like, but is not limited to these, each may include one or more.
- the present invention also provides an optical element encapsulation method using the optical element encapsulation composition and an optical element encapsulation film made of the optical element encapsulation composition.
- the optical element encapsulation method of the present invention is characterized by using the optical element encapsulation composition according to the present invention in a method of encapsulating the optical element with the optical element encapsulation composition. Processes applied to other encapsulation methods except for the use of the optical element encapsulation document may be well known processes.
- the present invention provides an optical element encapsulation film made of the optical element encapsulation composition
- the optical element encapsulation film of the present invention not only has excellent light transmittance and refractive index, but also has significantly improved hardness, adhesive strength and water vapor transmission rate,
- the optical element encapsulation film of the present invention When used as an encapsulation thin film of various optical elements is effective to extend the life of the optical element, in particular, it must be manufactured by a solvent-free process and can be used as the encapsulation film of LED that requires a thick film of several ⁇ m to several mm.
- Tetrasilanolphenyl POSS, dichloromethylpheylsilane, chlorodimethylvinylsilane were reactants, and the mixture was slowly added dropwise with distilled water at about 30 ° C. under normal pressure, followed by additional stirring at 50 ° C. for about 3 hours, and then the solvent was removed to remove the polyhedral oligomeric silses.
- Quioxane was synthesized.
- Octa Vinyl POSS and Hydrogenated poly (methylphenyl) siloxane Resin were synthesized by hydrosilylation reaction under platinum catalyst.
- Octa Hydro POSS and Vinyl terminated poly (methylphenyl) siloxane Resin were synthesized by hydrosilylation reaction under platinum catalyst.
- Siloxane Resin 1 Poly (methylphenyl) siloxane
- Siloxane resin 2 poly (phenylvinyl) -co- (methylvinyl) silsesquioxane
- Siloxane Resin 4 PVV-3522 (gelest)
- Crosslinked resin 2 dimethylsilylphenyl ether
- Organic polysilazane 1 HTT-1500 (AZ company)
- Organic polysilazane 2 Resin represented by the formula (2) HTT-1800 (AZ company)
- Modified polysilazane Modified polysilazane prepared in Synthesis Example 2
- Silane coupling agent Methacrylate-based cyclosiloxane
- Reaction Retardant 1 Ethynyltriethylsilane (gelest)
- Reaction Retardant 2 Ethynyltrimethylsilane (gelest)
- Light transmittance The composition is applied to the upper and lower glass and Teflon frame surface to have a size of 50 mm ⁇ 50 mm ⁇ 1 mm, then 1 hour at 150 °C, 1 hour at 170 °C
- the specimen was prepared by curing.
- the UV-vis spectrophotometer (Mecasys) was used to measure the transmittance of five points of the prepared specimen at a wavelength of 400 to 780 nm, and the light transmittance was evaluated from the average value within the obtained wavelength range.
- Hardness The composition was applied on a 20 mm ⁇ 20 mm ⁇ 15 mm mold, and then cured for 1 hour at 150 ° C. and 1 hour at 170 ° C. to prepare a specimen, and then measured using a hardness tester.
- Adhesive strength After applying the composition on a substrate of 100 mm ⁇ 15 mm, the two substrates were superimposed and cured for 1 hour at 150 °C, 1 hour at 170 °C to prepare a specimen, then a universal material tester ( Instron, product name: UTM-5566) was used.
- Refractive Index The composition was applied to the surface of a Teflon frame mold having a size of a rectangular parallelepiped (35 mm ⁇ 10 mm ⁇ 1 mm), and then cured for 1 hour at 150 ° C. and 1 hour at 170 ° C. to prepare a specimen. The resulting cured film was measured using an Abbe refractometer (589 nm).
- Examples 1 to 3 according to the present invention showed not only excellent light transmittance and refractive index, but also markedly improved hardness, adhesive strength and water vapor transmission rate.
- Examples 1 to 3 of the present invention showed excellent light transmittance and high reliability.
- C-POSS of Comparative Synthesis Examples 1 and 2 is a cage type (completely basket-shaped), and Products are light brown or yellowish-based. Therefore, the light transmittance is obtained in M-POSS of Synthesis Example 1 during curing after preparation of the final composition.
- the present invention is not suitable as the encapsulation material of the present invention in which the optical properties should be the basis, and the platinum catalyst used for synthesis may be added to the catalyst content of the whole composition and ultimately may adversely affect the reliability.
- the resin composition for encapsulating the optical device of the present invention includes a polyhedral oligomeric silsesquioxane (POSS) having increased compatibility with the resin due to crosslinking, thereby improving solubility with the siloxane resin, thereby allowing a solvent-free process. Therefore, the encapsulation process characteristics are excellent, the crosslinking density is improved, and the mechanical characteristics are excellent.
- the resin composition of the present invention can be thermally cured by including an organic polysilazane compound and a modified polysilazane compound, and greatly reduces the outgas phenomenon by removing unreacted monomers that cause outgas through such a process. Since it can improve, a barrier characteristic can be improved significantly.
- the resin composition for encapsulating the optical element of the present invention can be used as a solvent-free process, and thus may be usefully used as an optical element, in particular, an LED encapsulation composition. It can also be applied to the sealing process of a thick film of mm.
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
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CN201480010669.7A CN105008461B (zh) | 2013-02-28 | 2014-02-24 | 光学元件封装用树脂组合物 |
US14/769,155 US9593241B2 (en) | 2013-02-28 | 2014-02-24 | Resin composition for encapsulating optical element |
JP2015560090A JP6325006B2 (ja) | 2013-02-28 | 2014-02-24 | 光学素子封止用樹脂組成物 |
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CN104993067A (zh) * | 2015-07-13 | 2015-10-21 | 深圳市华星光电技术有限公司 | 有机发光二极管封装件、其制造方法及显示装置 |
US20160172552A1 (en) * | 2013-07-19 | 2016-06-16 | Az Electronic Materials (Luxembourg) S.A.R.L. | Encapsulation material for light emitting diodes |
CN109705802A (zh) * | 2018-12-30 | 2019-05-03 | 苏州桐力光电股份有限公司 | 一种液晶显示屏全贴合用高折光率硅胶 |
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CN114621634B (zh) | 2016-12-09 | 2023-07-14 | 株式会社Lg化学 | 封装组合物、包括该组合物的有机电子器件及其制造方法 |
CN111263981B (zh) * | 2017-10-31 | 2024-06-25 | 陶氏环球技术有限责任公司 | 用于光伏封装膜的聚烯烃组成物 |
KR102013860B1 (ko) * | 2017-11-24 | 2019-08-23 | 한국생산기술연구원 | 불소그룹이 도입된 불소 폴리실라잔 소재 및 이의 제조방법 |
KR20200082946A (ko) * | 2018-12-31 | 2020-07-08 | 주식회사 동진쎄미켐 | 합성 수지 코팅 조성물 및 이를 이용한 합성 수지 기재 제조 방법 |
CN112420893B (zh) * | 2020-10-28 | 2021-11-16 | 吉安市木林森半导体材料有限公司 | 一种使用硅氮烷进行封装的紫外led灯珠及其制备方法 |
NO347925B1 (en) | 2021-07-07 | 2024-05-13 | Nanize As | Polysilazane compositions |
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US20150376407A1 (en) | 2015-12-31 |
CN105008461B (zh) | 2019-07-05 |
TWI623587B (zh) | 2018-05-11 |
CN105008461A (zh) | 2015-10-28 |
KR102016348B1 (ko) | 2019-08-30 |
KR20140107815A (ko) | 2014-09-05 |
JP6325006B2 (ja) | 2018-05-16 |
TW201443156A (zh) | 2014-11-16 |
JP2016514179A (ja) | 2016-05-19 |
US9593241B2 (en) | 2017-03-14 |
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