KR20170037086A - Pressure-sensitive adhesive composition - Google Patents
Pressure-sensitive adhesive composition Download PDFInfo
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- KR20170037086A KR20170037086A KR1020150136186A KR20150136186A KR20170037086A KR 20170037086 A KR20170037086 A KR 20170037086A KR 1020150136186 A KR1020150136186 A KR 1020150136186A KR 20150136186 A KR20150136186 A KR 20150136186A KR 20170037086 A KR20170037086 A KR 20170037086A
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- Prior art keywords
- pressure
- sensitive adhesive
- adhesive composition
- group
- weight
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- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims description 93
- 239000002313 adhesive film Substances 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims description 37
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 17
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 12
- 238000007789 sealing Methods 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000011148 porous material Substances 0.000 claims description 5
- 238000002834 transmittance Methods 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000004292 cyclic ethers Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000686 lactone group Chemical group 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 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 5
- 230000003287 optical effect Effects 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 50
- 238000001723 curing Methods 0.000 description 19
- -1 (7-oxabicyclo [4.1.0] heptan-3-yl) methyl Chemical group 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 235000007586 terpenes Nutrition 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000012663 cationic photopolymerization Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000011368 organic material Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920005987 OPPANOL® Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene 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
- 239000012963 UV stabilizer Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 229930006737 car-3-ene Natural products 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000013039 cover film Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- KIOWHOMJXAQSMW-UHFFFAOYSA-N phenol;4,6,6-trimethylbicyclo[3.1.1]hept-3-ene Chemical compound OC1=CC=CC=C1.CC1=CCC2C(C)(C)C1C2 KIOWHOMJXAQSMW-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C09J123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C09J7/021—
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
Abstract
Description
The present application relates to a pressure-sensitive adhesive composition, an adhesive film comprising the same, and an organic electronic device including the same.
An organic electronic device (OED) refers to an apparatus that includes an organic material layer that generates holes and electrons to generate an alternating current. Examples thereof include a photovoltaic device, a rectifier, A transmitter and an organic light emitting diode (OLED).
Organic light emitting diodes (OLEDs) among the organic electronic devices have lower power consumption, faster response speed, and are advantageous for thinning display devices or illumination. In addition, OLEDs are expected to be applied in various fields covering various portable devices, monitors, notebooks, and televisions because of their excellent space utilization.
In commercialization of OLEDs and expansion of applications, the main problem is durability. Organic materials and metal electrodes contained in OLEDs are very easily oxidized by external factors such as moisture. Thus, products containing OLEDs are highly sensitive to environmental factors. Accordingly, various methods have been proposed to effectively block penetration of oxygen or moisture from the outside into organic electronic devices such as OLEDs.
In Patent Documents 1 to 4, a technique related to a PIB (polysionbutylene) resin is proposed. In recent years, attempts have been made to use a PIB (polyisobutylene) resin as a pressure-sensitive adhesive composition for sealing. PIB (polysionbutylene) resin is superior in transparency and corrosion resistance, and has excellent barrier properties to prevent the influence of moisture and active oxygen as compared with acrylic resin. However, it causes problems such as restriction of the hardener content due to compatibility problems and consequent reduction of the water barrier effect due to the problem of lowering the crosslink density.
The present application provides a pressure-sensitive adhesive composition which can effectively block moisture or oxygen introduced into the organic electronic device from the outside and has excellent mechanical properties such as handling and workability and transparency, and an adhesive film containing the same.
The present application relates to a pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition can be applied to encapsulating or encapsulating organic electronic devices such as, for example, OLEDs. For example, the pressure-sensitive adhesive composition may be applied to encapsulate the front surface of an organic electronic device, or may be applied to a surface of the substrate on which the device is formed, to be located on the opposite side of the surface on which the device is formed.
As used herein, the term " organic electronic device " refers to an article or apparatus having a structure including an organic material layer that generates alternating electric charges using holes and electrons between a pair of electrodes facing each other, But are not limited to, photovoltaic devices, rectifiers, transmitters, and organic light emitting diodes (OLEDs). In one example of the present invention, the organic electronic device may be an OLED.
In the present application, the pressure-sensitive adhesive composition may comprise a curable oligomer comprising a polymer derived from isobutylene and at least one cyclic ether group. The pressure-sensitive adhesive composition is applied to encapsulating an organic electronic device, and can realize durability reliability at high temperature and high humidity together with excellent moisture barrier properties.
The term " a polymer derived from isobutylene " in the present application means that the polymerization unit of the specific polymer is composed of isobutylene.
In one embodiment, the polymer derived from isobutylene may be used as a polymer of a pressure-sensitive adhesive film composed of a pressure-sensitive adhesive composition. Since the polymer derived from isobutylene has a very low polarity, is transparent, and has almost no influence of corrosion, excellent moisture barrier properties, durability and optical properties can be realized.
Also in the present application the polymer derived from isobutylene is a homopolymer of isobutylene monomer; A copolymer obtained by copolymerizing an isobutylene monomer with another monomer capable of polymerization; Or a mixture thereof. The polymers derived from this application may mean that the monomers are forming polymers in polymerized units.
Other monomers polymerizable with the isobutylene monomer may include, for example, 1-butene, 2-butene, isoprene, styrene or butadiene. By using the copolymer, physical properties such as processability and degree of crosslinking can be maintained, and occurrence of dark spots due to electrochemical corrosion can be minimized when applied to organic electronic devices.
In one example, the polymer is selected from the group consisting of polyisobutylene, copolymers of isobutylene and isoprene, copolymers of isoprene and styrene, copolymers of butadiene and styrene, copolymers of isoprene, butadiene and styrene, and polyisoprene, Butadiene or copolymers of isoprene and styrene, copolymers of butadiene and styrene, or copolymers of isoprene, butadiene and styrene.
In addition, the polymer may have at least one reactive functional group. The reactive functional group may be a form in which a monomer having a reactive functional group is grafted onto the polymer, but is not limited thereto. That is, in this case, the polymer may be a copolymer in which the monomer is grafted to a polymer derived from isobutylene to be modified. Examples of the reactive functional group may be a cyclic epoxide group, a glycidyl ether group, a hydroxyl group, a carboxyl group, an amine group or an anhydride group, and the monomer having a reactive functional group may be a compound having a vinyl group or a (meth) Lt; / RTI > Further, in one example, the reactive functional group may be introduced via epoxidation into an unsaturated group in the polymer.
In the present application, the polymer may have a weight average molecular weight (MW) such that the pressure-sensitive adhesive composition can be formed into a film. For example, the polymer may have a weight average molecular weight of about 10,000 to 2,000,000, 10,000 to 1,000,000, 10,000 to 500,000, or 10,000 to 300,000. The term "weight average molecular weight" as used herein means a value converted to a standard polystyrene measured by GPC (Gel Permeation Chromatograph). However, the resin component does not necessarily have to have the weight average molecular weight mentioned above. For example, even when the molecular weight of the resin component does not become so high as to form a film, a separate binder resin may be blended into the pressure-sensitive adhesive composition. The term polymer and resin component may be used interchangeably herein.
In one example, the pressure sensitive adhesive composition may comprise a curable oligomer with the polymer. The curable oligomer may include at least one curable functional group.
In the present application, the curable oligomer has high compatibility with a polymer and can form a crosslinked structure together with the polymer. The curable oligomer according to the present application may be UV curable, but is not limited to, and may be thermosetting. The curable oligomer may include at least one curable functional group. The curable functional group may be at least one selected from, for example, a glycidyl group, an isocyanate group, a hydroxyl group, a carboxyl group, an amide group, an epoxide group, a cyclic ether group, a sulfide group, an acetal group and a lactone group. In one example, the curable oligomer may comprise at least one cyclic ether group. The curable oligomer realizes an excellent heat resistance at high temperature and high humidity by realizing an appropriate degree of crosslinking in a pressure-sensitive adhesive.
In one example, the curable oligomer may have, but is not limited to, a cyclic structure in which the ring constituent atoms within the molecular structure are in the range of 3 to 10, 4 to 9, or 5 to 8. Further, the curable resin may have the annular structure even after the pressure-sensitive adhesive is cured. The annular structure may be alicyclic. The curable oligomer having the above structure can realize a stable crosslinking structure against external factors such as shrinkage and expansion even after the pressure-sensitive adhesive is crosslinked or cured.
In one example, the curable oligomer may have a weight average molecular weight ranging from 500 to 100,000, from 550 to 90,000, from 600 to 80,000, from 650 to 70,000, or from 650 to 60,000. Within the above-mentioned molecular weight range, the pressure-sensitive adhesive composition of the present application can be cured to have excellent moisture barrier properties, and excellent heat resistance and adhesiveness of the pressure-sensitive adhesive after curing can be realized.
Examples of the curable oligomer include commercially available products such as EHPE3150, GT401, PB3600, and PB4700 manufactured by DAICEL. Also included are ether group-containing monomers such as M100 (7-oxabicyclo [4.1.0] heptan-3-yl) methyl methacrylate) or celloxide 2000 (4-vinyl-1-cyclohexene 1,2- Cationically-curable oligomers prepared by radical polymerization or the like using an ether group-containing monomer having a cyclic structure.
20 to 90 parts by weight, 20 to 80 parts by weight, 25 to 70 parts by weight, 25 to 60 parts by weight, and 28 to 50 parts by weight, based on 100 parts by weight of the polymer derived from isobutylene, Or 28 to 40 parts by weight. Within the above-mentioned weight range, the present application can be applied to encapsulating an organic electronic device to realize an endurance reliability at high temperature and high humidity together with excellent moisture barrier properties.
In one example, the pressure sensitive adhesive composition of the present application may further comprise a tackifier. The tackifier may be a resin produced by reacting a terpene compound with an aromatic compound. When the tackifier has an aromatic group in the molecular structure, the compatibility between the above-mentioned polymer having a low polarity and the curable oligomer having a high polarity can be improved. The aromatic compound may include a reactive functional group. Examples of the functional group include a hydroxyl group, a carboxyl group, and an amine group. In the present application, the cross-linking density of the whole pressure-sensitive adhesive can be improved due to the reactive functional group. Specifically, the aromatic compound may be phenol, and the tackifier may be a terpene phenolic resin. In the present application, it is possible to provide a pressure-sensitive adhesive excellent in adhesive strength as well as in compatibility with a polymer and a curable oligomer by using the terpene phenolic resin as a tackifier, thereby improving cross-link density and durability have.
The tackifier may be a resin produced by reacting a terpene compound with a phenolic compound. Terpene compound may represent a compound having a basic skeleton n (C 5 H 8) is 2 or more isoprene (C 5 H 8) combination. In the above, n may be two or more. In the above, the terpene compound may be at least one selected from the group consisting of? -Pinene,? -Pinene,? -Carenylene, 3-carene, D-limonene and dipentene. The phenolic compound may also be selected from the group consisting of phenol, para-tert-butylphenol (PTBP), 4-t-octylphenol (PTOP), 4- -pentyl phenol (PNPP), and para-n-hexyl phenol (PNHP).
The tackifier may be included in an amount of 30 to 90 parts by weight, 30 to 80 parts by weight, 35 to 70 parts by weight, 35 to 60 parts by weight or 38 to 50 parts by weight based on 100 parts by weight of the polymer derived from isobutylene. Within the above weight range, the pressure sensitive adhesive can excellently realize compatibility of the polymer with the curable oligomer.
The tackifier may, for example, have a softening point in the range of 80 占 폚 to 150 占 폚, 90 占 폚 to 145 占 폚, 100 占 폚 to 140 占 폚, or 104 占 폚 to 135 占 폚. The tackifier may also have a weight average molecular weight ranging from 100 to 10,000, from 200 to 9,000, from 300 to 8,000 or from 400 to 7,000, and a glass transition temperature from 53 to 120, 55 to 110 or 60 to 100 Lt; 0 > C. Within this specific range, it is possible to produce a pressure sensitive adhesive in which the crosslinking density is attained to the degree desired in the present application.
In the embodiment of the present application, the pressure-sensitive adhesive composition may further include a curing agent or an initiator depending on the kind of the polymer and the curable oligomer. For example, a curing agent capable of reacting with the above-mentioned polymer and a curable oligomer to form a crosslinked structure or the like or a cationic initiator capable of initiating a curing reaction may be further included. As the cationic initiator, a cationic photopolymerization initiator or a cationic thermal initiator may be used.
As the curing agent, there can be used one or more kinds of epoxy curing agents known in the art, such as amine curing agents, imidazole curing agents, phenol curing agents, phosphorus curing agents and acid anhydride curing agents, but not limited thereto .
In one example, as the curing agent, an imidazole compound which is solid at room temperature and has a melting point or a decomposition temperature of 80 ° C or higher can be used. Such compounds include, for example, 2-methylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole or 1-cyanoethyl- May be exemplified, but the present invention is not limited thereto.
The content of the curing agent may be selected depending on the composition of the composition, for example, the kind and ratio of the polymer and the curable oligomer. For example, the curing agent may be contained in an amount of 1 to 20 parts by weight, 1 to 10 parts by weight, or 1 to 5 parts by weight based on 100 parts by weight of the curable resin. However, the weight ratio may vary depending on the type and ratio of the functional group of the polymer and the curable oligomer or the compound, the crosslinking density to be implemented, and the like.
In one example, when the curable oligomer is a resin that can be cured by irradiation with active energy rays, for example, a cationic photopolymerization initiator may be used as the initiator.
As the cationic photopolymerization initiator, an ionized cationic initiator or an organic silane or latent sulfonic acid series based onium salt or organometallic salt series or a nonionic ionic cationic photopolymerization initiator can be used. As the initiator of the onium salt series, diaryliodonium salt, triarylsulfonium salt or aryldiazonium salt can be exemplified, and the initiation of the organometallic salt series Examples of the initiator of the organosilane series include o-nitrobenzyl triaryl silyl ether, triaryl silyl peroxide, and the like. Or an acyl silane, and examples of the initiator of the latent sulfuric acid series include, but are not limited to,? -Sulfonyloxy ketone or? -Hydroxymethylbenzoin sulfonate, and the like .
In one example, an ionized cationic photopolymerization initiator may be used as the cationic initiator.
In one example, the initiator may be included in an amount of 0.1 to 10 parts by weight, 0.1 to 7 parts by weight, or 0.1 to 6 parts by weight based on 100 parts by weight of the curable oligomer.
In the present specification, unless otherwise specified, the unit " weight part " means a weight ratio between the respective components.
In one example, the pressure-sensitive adhesive composition may have a rate of change of gel content according to the following general formulas 1 and 2 to 30% or less.
[Formula 1]
Rate of change in gel content = (| G f -G i |) / G i x 100
[Formula 2]
Gel content (% by weight) = B / A x 100
In the above general formula 1, G i is the gel content immediately after coating the pressure-sensitive adhesive composition on the PET substrate, and G f means the gel content after vacuum-sealing the coated sample on the aluminum pouch at room temperature for 7 days .
In the general formula 2, A represents the mass of the pressure-sensitive adhesive composition; B represents the mass of the pressure-sensitive adhesive composition; the pressure-sensitive adhesive composition is immersed in toluene at 25 ° C for 24 hours and then filtered with a mesh of 200 mesh (pore size 74 μm) And indicates the dry mass of the insoluble component of the pressure-sensitive adhesive composition that has not passed through.
Specifically, the gel content can be measured by UV-curing the coated pressure-sensitive adhesive, then aging for one day, sufficiently curing, and then sampling at about 0.5 g. The sampled sample was immersed in 100 ml of toluene for 24 hours at 25 ° C., filtered through a mesh of 200 mesh (pore size: 74 μm), and dried for 2 hours or more in an oven at 150 ° C. The weight can be measured.
The pressure-sensitive adhesive composition according to the present application may contain various additives in addition to the above-mentioned composition, in addition to the effects of the above-mentioned invention, depending on the application, the kind of the resin component and the process for producing the pressure-sensitive adhesive layer described later. For example, the pressure-sensitive adhesive composition may be contained in an appropriate range depending on the intended properties of a moisture adsorbent, an inorganic filler, a coupling agent, a crosslinking agent, a curing substance, a UV stabilizer or an antioxidant.
The present application also relates to an adhesive film. The pressure-sensitive adhesive film may include a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition described above. The structure of the pressure-sensitive adhesive film of the present application is not particularly limited, but may be, for example, a base film or a release film (hereinafter sometimes referred to as " first film "); And a pressure-sensitive adhesive layer formed on the base film or the release film.
The pressure-sensitive adhesive film of the present application may further include a base film or a release film (hereinafter sometimes referred to as " second film ") formed on the pressure-sensitive adhesive layer.
The specific kind of the first film that can be used in the present application is not particularly limited. In the present application, for example, a general polymer film in this field can be used as the first film. In the present application, for example, the base material or the release film may be a polyethylene terephthalate film, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a polyvinyl chloride film, , An ethylene-vinyl acetate film, an ethylene-propylene copolymer film, an ethylene-ethyl acrylate copolymer film, an ethylene-methyl acrylate copolymer film, or a polyimide film. In addition, a suitable mold release treatment may be performed on one or both surfaces of the base film or release film of the present application. Examples of the releasing agent used in the releasing treatment of the base film include an alkyd type, a silicone type, a fluorine type, an unsaturated ester type, a polyolefin type, a wax type and the like. Among them, the use of an alkyd type, a silicone type or a fluorine type releasing agent But is not limited thereto.
Also, the kind of the second film (hereinafter sometimes referred to as " cover film ") that can be used in the present application is not particularly limited either. For example, in the present application, as the second film, the same or a different kind as the first film may be used within the scope exemplified in the first film described above. In the present application, the second film may also be subjected to appropriate mold release treatment.
The thickness of the pressure-sensitive adhesive layer included in the pressure-sensitive adhesive film of the present application is not particularly limited and may be appropriately selected in accordance with the following conditions in consideration of the application to which the film is applied. The thickness of the pressure-sensitive adhesive layer included in the pressure-sensitive adhesive film of the present application may be about 5 占 퐉 to 200 占 퐉, preferably about 10 占 퐉 to 150 占 퐉.
In one embodiment, the pressure-sensitive adhesive film of the present application can satisfy the following general formula (3).
[Formula 3]
DELTA X ≤ 1.2 mm
X in the general formula 3 is a value obtained when the substrate film formed on one side of the pressure-sensitive adhesive layer having a thickness of 30 탆 is adhered to a glass plate with an adhesion area of 1 cm 2 and aged for 24 hours, and then a load of 1.5 kg is applied at 25 캜 for 1000 seconds. Indicates the pushing distance of the pressure-sensitive adhesive layer. The pushing distance represented by the general formula 3 may be 1.2 mm or less, 0.1 to 1.1 mm, 0.15 to 1.0 mm, or 0.2 to 0.93 mm. That is, the present invention secures an appropriate range of the crosslinking structure and the degree of crosslinking, thereby controlling the pushing distance to 1.2 mm or less. In particular, when the adhesive film is applied to organic electronic devices, excellent moisture barrier properties, And optical characteristics.
In addition, the pressure-sensitive adhesive film may have excellent light transmittance with respect to the visible light region. In one example, the pressure-sensitive adhesive film of the present application can exhibit a light transmittance of 90% or more with respect to the visible light region. For example, the adhesive film may have a light transmittance of 92% or more or 95% or more with respect to the visible light region. Further, the pressure-sensitive adhesive film of the present application can exhibit low haze with excellent light transmittance. In one example, the adhesive film may exhibit a haze of 10% or less, 8% or less, 7% or less, 6% or less, 5% or less, 4% or less, or 3% or less. The optical characteristics may be measured at 550 nm using a UV-Vis spectrometer.
The present application also includes a
The organic electronic device in the present application may be an organic light emitting diode.
The organic electronic device may further include a protective film for protecting the device on the organic electronic device.
The organic electronic device may further include a
The present application also relates to a method of manufacturing an organic electronic device, comprising the step of forming an adhesive film on the other side of a substrate on which an organic electronic element is formed, the adhesive film comprising the above-described adhesive composition. In one example, the manufacturing method may further include a step of crosslinking or curing the adhesive film.
In addition, the adhesive film exhibits excellent transparency and can be formed as a stable adhesive film regardless of the form of the organic electronic device such as top emission or bottom emission.
As used herein, the term " curing " means that the adhesive composition of the present invention forms a cross-linked structure through heating or UV irradiation, etc., and is produced in the form of a pressure-sensitive adhesive.
Specifically, a transparent electrode is formed on a glass or polymer film used as a substrate by a method such as vacuum deposition or sputtering. On the transparent electrode, a light-emitting organic material composed of a hole transporting layer, a light- And then an electrode layer is further formed on the electrode layer to form an organic electronic device.
Then, the adhesive film is placed on the other surface of the substrate, and the adhesive film is heated using a laminate or the like to press the adhesive film in a state of imparting fluidity, and the resin in the adhesive film can be crosslinked.
The present invention provides a pressure-sensitive adhesive composition capable of effectively blocking water or oxygen introduced from the outside into an organic electronic device and capable of realizing not only durability reliability under harsh conditions such as high temperature and high humidity but also excellent optical characteristics, and an adhesive film comprising the same .
1 is a cross-sectional view showing an organic electronic device according to one example of the present invention.
Hereinafter, the present invention will be described in more detail with reference to the following examples and comparative examples, but the scope of the present invention is not limited by the following examples.
Example One
10 g of polyisobutylene (Oppanol B80, manufactured by BASF) as a polymer was charged into a mixing vessel, and 30 parts by weight of an alicyclic epoxy oligomer compound (EHPE3150, DAICEL) as a curable oligomer was added in an amount of 30 parts by weight per 100 parts by weight of the solid content of the polymer. Lt; / RTI > Further, as a tackifier (DERTOPHENE T 115, manufactured by DRT Co.), 40 parts by weight of 100 parts by weight of the polymer was added to the vessel, and a triacylsulfonium hexafluoroantimonate (Aldrich) was added to 100 parts by weight of the solid content of the oligomer compound Parts by weight were further added to the container.
A homogeneous pressure-sensitive adhesive composition solution (solvent: toluene) was prepared using a conventional mechanical stirrer as the mixing container.
The prepared solution was coated on the release surface of the release PET and dried in an oven at 130 캜 for 3 minutes to produce an adhesive film comprising a pressure-sensitive adhesive layer having a thickness of 30 탆. The properties of the thus-prepared film were measured for a sample irradiated with 2 J / cm 2 of ultraviolet light (100 mW / cm 2 on the basis of area A).
Comparative Example One
Except that bis [1-ethyl (3-oxetanyl)] methyl ether (OXT221, Toagossei) was used in place of the alicyclic epoxy oligomer compound (EHPE3150, DAICEL) Respectively.
One. Gel content Rate of change
[Formula 1]
Rate of change in gel content = (| G f -G i |) / G i x 100
[Formula 3]
Gel content (% by weight) = B / A x 100
G i in the general formula 1 means the gel content immediately after coating the pressure-sensitive adhesive composition on the PET substrate, and G f means the gel content after vacuum-sealing the coated sample on the aluminum pouch at room temperature for 7 days .
In the general formula 3, A represents the mass of the pressure-sensitive adhesive composition; B represents the mass of the pressure-sensitive adhesive composition; the pressure-sensitive adhesive composition is immersed in toluene at 25 DEG C for 24 hours and then filtered with a mesh of 200 mesh (pore size 74 mu m) And indicates the dry mass of the insoluble component of the pressure-sensitive adhesive composition that has not passed through.
Specifically, the gel content was measured by UV-curing the coated pressure-sensitive adhesive after aging for one day and sufficiently curing it, and then sampling at around 0.5 g. The sampled sample was immersed in 100 ml of toluene for 24 hours at 25 ° C., filtered through a mesh of 200 mesh (pore size: 74 μm), and dried for 2 hours or more in an oven at 150 ° C. The weight was measured.
2. Creep
Examples and a comparative example, a pressure-sensitive adhesive composition load of 1.5 kg at 25 ℃ was attached to a base film formed on one surface a pressure-sensitive adhesive layer having a thickness of 30 ㎛ the adhesion area 1cm 2 glass plate and stand for 24 hours, including walked for 1000 sec Of the pressure-sensitive adhesive layer between 50 seconds and 1000 seconds. The base film is not particularly limited, and for example, a polyethylene terephthalate (PET) film is used.
3. moisture permeability
A glass substrate (70 x 70 mm) and a face seal adhesive (LG chemical) were laminated together and a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition of Examples and Comparative Examples was laminated on the face sealing pressure-sensitive adhesive, and barrier films (FTB 3-50, 3M), cured by UV irradiation, aged at room temperature for 1 day, and then measured for penetration length on the basis of 500 hours at 85 ° C and 85% relative humidity.
The above measurement results are summarized in Table 1 below.
In the case of Example 1, the gel content measured immediately after coating of the pressure sensitive adhesive was 38 wt%, and the gel content measured after 7 days of sealing was 47 wt%. In the case of Comparative Example 1, the gel content measured immediately after coating of the pressure sensitive adhesive was 39 wt%, and the gel content measured after 7 days of sealing was 1.1 wt%.
21: substrate
22: Cover substrate
23: Organic electronic device
24: Adhesive film
12: Encapsulation material
Claims (18)
[Formula 1]
Rate of change in gel content = (| G f -G i |) / G i x 100
[Formula 2]
Gel content (% by weight) = B / A x 100
In the general formula 1, G i represents the gel content immediately after coating the pressure-sensitive adhesive composition on the PET substrate, and G f represents the gel content after vacuum-sealing the coated sample on the aluminum pouch at room temperature for 7 days ,
In the general formula 2, A represents the mass of the pressure-sensitive adhesive composition, B represents the mass of the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive composition is immersed in toluene at 25 ° C for 24 hours, and then filtered with a mesh of 200 mesh (pore size 74 μm) The dry mass of the insoluble component of the pressure-sensitive adhesive composition.
[Formula 3]
DELTA X ≤ 1.2 mm
X in the general formula 3 is a value obtained when the substrate film formed on one side of the pressure-sensitive adhesive layer having a thickness of 30 탆 is adhered to a glass plate with an adhesion area of 1 cm 2 and aged for 24 hours, and then a load of 1.5 kg is applied at 25 캜 for 1000 seconds. Indicates the pushing distance of the pressure-sensitive adhesive layer.
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| KR1020150136186A KR20170037086A (en) | 2015-09-25 | 2015-09-25 | Pressure-sensitive adhesive composition |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018199705A1 (en) * | 2017-04-28 | 2018-11-01 | 주식회사 엘지화학 | Encapsulating composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0578635A (en) | 1991-09-19 | 1993-03-30 | Nitto Denko Corp | Production of pressure-sensitive adhesive and adhesive sheets |
| KR20080088606A (en) | 2006-01-24 | 2008-10-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | Adhesive encapsulating composition film and organic electroluminescence device |
| KR20120091349A (en) | 2009-11-18 | 2012-08-17 | 아지노모토 가부시키가이샤 | Resin composition |
| KR20140090936A (en) | 2012-12-21 | 2014-07-18 | 이엠에스-패턴트 에이지 | Stain-resistant article and use thereof |
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2015
- 2015-09-25 KR KR1020150136186A patent/KR20170037086A/en not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0578635A (en) | 1991-09-19 | 1993-03-30 | Nitto Denko Corp | Production of pressure-sensitive adhesive and adhesive sheets |
| KR20080088606A (en) | 2006-01-24 | 2008-10-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | Adhesive encapsulating composition film and organic electroluminescence device |
| KR20120091349A (en) | 2009-11-18 | 2012-08-17 | 아지노모토 가부시키가이샤 | Resin composition |
| KR20140090936A (en) | 2012-12-21 | 2014-07-18 | 이엠에스-패턴트 에이지 | Stain-resistant article and use thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018199705A1 (en) * | 2017-04-28 | 2018-11-01 | 주식회사 엘지화학 | Encapsulating composition |
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