KR102034441B1 - Pressure-sensitive adhesive composition - Google Patents
Pressure-sensitive adhesive composition Download PDFInfo
- Publication number
- KR102034441B1 KR102034441B1 KR1020150136185A KR20150136185A KR102034441B1 KR 102034441 B1 KR102034441 B1 KR 102034441B1 KR 1020150136185 A KR1020150136185 A KR 1020150136185A KR 20150136185 A KR20150136185 A KR 20150136185A KR 102034441 B1 KR102034441 B1 KR 102034441B1
- Authority
- KR
- South Korea
- Prior art keywords
- pressure
- sensitive adhesive
- adhesive composition
- group
- weight
- Prior art date
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000000853 adhesive Substances 0.000 claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 30
- 239000002313 adhesive film Substances 0.000 claims description 25
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000010410 layer Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 238000007789 sealing Methods 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 239000004593 Epoxy Substances 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 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
- 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
- 239000004848 polyfunctional curative Substances 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
- 230000003287 optical effect Effects 0.000 abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 239000003292 glue Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 48
- -1 acrylate compound Chemical class 0.000 description 19
- 238000004132 cross linking Methods 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 229920002367 Polyisobutene Polymers 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 4
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- 239000011521 glass Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000012663 cationic photopolymerization Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance 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
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- BQOFWKZOCNGFEC-DTWKUNHWSA-N (-)-Delta(3)-carene Chemical compound C1C(C)=CC[C@@H]2C(C)(C)[C@H]12 BQOFWKZOCNGFEC-DTWKUNHWSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZIHDWZZSOZGDDK-UHFFFAOYSA-N 2-(2,3-dihydroxy-2-phenylpropanoyl)benzenesulfonic acid Chemical compound OCC(C(C=1C(=CC=CC=1)S(=O)(=O)O)=O)(O)C1=CC=CC=C1 ZIHDWZZSOZGDDK-UHFFFAOYSA-N 0.000 description 1
- 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
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-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
- SZWBRVPZWJYIHI-UHFFFAOYSA-N 4-n-Hexylphenol Chemical compound CCCCCCC1=CC=C(O)C=C1 SZWBRVPZWJYIHI-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- NRJLSUZLHMXXHJ-UHFFFAOYSA-N [4-(7-oxabicyclo[4.1.0]heptane-4-carbonyloxymethyl)cyclohexyl]methyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CCC(COC(=O)C2CC3OC3CC2)CC1 NRJLSUZLHMXXHJ-UHFFFAOYSA-N 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
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 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
- 230000008901 benefit Effects 0.000 description 1
- 229930006722 beta-pinene Natural products 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
- 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
- 230000018109 developmental process Effects 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
- 238000001035 drying Methods 0.000 description 1
- 238000006056 electrooxidation reaction Methods 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
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 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
- 238000002156 mixing Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 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
- 229920006264 polyurethane film Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
The present application can effectively block moisture or oxygen introduced into the organic electronic device from the outside, and provides a "glue adhesive composition" and a pressure-sensitive adhesive film that can implement not only the durability in harsh conditions such as high temperature and high humidity, but also excellent optical properties. .
Description
The present application relates to an adhesive composition, an adhesive film including the same, and an organic electronic device including the same.
An organic electronic device (OED) refers to a device including an organic material layer that generates an exchange of electric charges using holes and electrons, and examples thereof include a photovoltaic device, a rectifier, Transmitters and organic light emitting diodes (OLEDs); and the like.
Among the organic electronic devices, organic light emitting diodes (OLEDs) have low power consumption, fast response speed, and are advantageous for thinning a display device or lighting, as compared with conventional light sources. In addition, OLED has excellent space utilization, and is expected to be applied in various fields including various portable devices, monitors, notebooks, and TVs.
In the commercialization of OLEDs and the expansion of their use, the main problem is durability. Organic materials and metal electrodes included in the OLED are very easily oxidized by external factors such as moisture. Therefore, products containing OLEDs are highly sensitive to environmental factors. Accordingly, various methods have been proposed to effectively block the penetration of oxygen or moisture from the outside into organic electronic devices such as OLEDs.
Recently, a technique using a PIB (polyisobutylene) resin as an adhesive composition for sealing has been attempted. PIB (polysionbutylene) resin is superior to the acrylic resin has excellent barrier properties that can prevent the effects of moisture and active oxygen, and has the advantage of being transparent, little effect of corrosion. However, the problem of reducing the water barrier effect due to the limitation of the curing agent content and the resulting crosslinking density decrease due to compatibility problems.
Patent document 1 is an adhesive encapsulation composition film and an organic electroluminescent element, which is poor in workability with an adhesive based on PIB (polyisobutylene) and poor in high temperature and high humidity conditions.
Accordingly, there is a demand for the development of an encapsulant that can maintain reliability under high temperature and high humidity conditions while ensuring a required lifespan in an organic electronic device and effectively blocking the penetration of moisture, and having excellent optical properties.
The present application can effectively block moisture or oxygen introduced into the organic electronic device from the outside, and provides a pressure-sensitive adhesive composition having excellent mechanical properties and transparency, such as handleability and processability, and an adhesive film including the same.
The present application relates to an adhesive composition. The pressure-sensitive adhesive composition may be applied to encapsulate or encapsulate an organic electronic device such as, for example, an OLED. For example, the pressure-sensitive adhesive composition may be applied to encapsulate the entire surface of the organic electronic device, or may be applied to the opposite surface of the surface on which the device is formed.
As used herein, the term "organic electronic device" means an article or device having a structure including an organic material layer that generates an exchange of electric charge using holes and electrons between a pair of electrodes facing each other. The photovoltaic device, a rectifier, a transmitter, and an organic light emitting diode (OLED) may be mentioned, but is not limited thereto. 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 include a polymer derived from isobutylene, a curable resin, a hardening agent, and a photoinitiator. The hardening agent may include a thermosetting agent or a thermal initiator. The pressure-sensitive adhesive composition according to the present application may include a thermal initiator or a thermosetting agent and a photoinitiator together, and thus may be temporarily cured using heat during coating and drying of the pressure-sensitive adhesive, thereby preventing phase separation from occurring during storage of the uncured pressure-sensitive adhesive. . Such a pressure-sensitive adhesive composition is applied to encapsulate the organic electronic device, it is possible to implement the durability reliability at high temperature and high humidity with excellent moisture barrier properties.
In one example, the pressure-sensitive adhesive composition may be a change rate of the gel content according to the general formulas 1 and 2 below 30%.
[Formula 1]
Rate of change of gel content = (| G f -G i |) / G i × 100
[Formula 2]
Gel content (% by weight) = B / A × 100
In Formula 1, G i is the gel content immediately after coating the pressure-sensitive adhesive composition on a PET substrate, and G f is the gel content after vacuum-sealing the coated sample after the coating in an aluminum pouch for 7 days at room temperature. Can be.
In addition, in the general formula 2, A represents the mass of the pressure-sensitive adhesive composition, B is immersed in the pressure-sensitive adhesive composition for 24 hours with toluene at 25 ℃ and filtered through a mesh of 200 mesh (pore size 74 ㎛), the network The dry mass of the insoluble content of the adhesive composition which did not pass is shown.
Specifically, the gel content may be measured by UV treatment of the coated pressure sensitive adhesive, followed by Aging for 1 day, and then curing by sampling around 0.5g. After the sample was immersed in 100ml of toluene at 25 ℃ for 24 hours, filtered through a mesh of 200 mesh (pore size 74㎛), and dried in a 150 ℃ oven for at least 2 hours for insoluble content not passed through the network The weight can be measured.
In addition, in one example, the pressure-sensitive adhesive composition may satisfy the following general formula (3).
[Formula 3]
ΔX ≤ 1000 μm
In Formula 3, X is a cross-linked product of the pressure-sensitive adhesive composition to form a pressure-sensitive adhesive layer having a thickness of 30 μm, and the base film having the pressure-sensitive adhesive layer formed on one surface is attached to a glass plate with an adhesive area of 1 cm 2, and aged for 24 hours. When the 1.5 kg load was applied for 1000 seconds at 25 ° C, the pushed distance of the pressure-sensitive adhesive layer is shown. The pushed distance represented by Formula 3 may be 750 μm or less, 10 to 700 μm, or 100 to 650 μm. That is, the present application secures a cross-linked structure and a degree of cross-linking within an appropriate range, thereby controlling the pushed distance to 750 μm or less, and particularly, when the adhesive film is applied to an organic electronic device, excellent moisture barrier property and durability. And optical properties.
In the present application, the term "polymer derived from isobutylene" may mean that the polymerized unit of a specific polymer consists of isobutylene.
In one embodiment, the polymer derived from isobutylene may be used as the polymer of the pressure-sensitive adhesive film made of the pressure-sensitive adhesive composition. Since the polymer derived from isobutylene is very low in polarity, transparent, and hardly affected by corrosion, it is possible to realize excellent moisture barrier properties, durability, and optical properties.
In the present application also the polymer derived from isobutylene is a homopolymer of isobutylene monomer; Copolymers obtained by copolymerizing isobutylene monomers with other monomers polymerizable; Or mixtures thereof. The polymer derived in the present application may mean that the monomer forms a polymer in a polymerized unit.
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 crosslinking degree can be maintained, so that the occurrence of dark spots due to electrochemical corrosion when applied to organic electronic devices can be minimized.
In one example, the polymer is polyisobutylene, copolymer of isobutylene and isoprene, copolymer of isoprene and styrene, copolymer of butadiene and styrene, copolymer of isoprene, butadiene and styrene, and polyisoprene, poly Butadiene or co-isoprene and styrene copolymers, butadiene and styrene copolymers or co-isoprene, butadiene and styrene.
In addition, the polymer may have at least one or more reactive functional groups as described above. The reactive functional group may be in a form in which a monomer having a reactive functional group is grafted to 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 and 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 the reactive functional group is a compound having a vinyl group or a (meth) acrylate compound. Can be. In addition, in one example, the reactive functional group may be introduced through epoxidation to the unsaturated group in the polymer.
The polymer in the present application may have a weight average molecular weight (MW.Weight Average Molecular Weight) of the adhesive composition can be molded into a film shape. For example, the polymer may have a weight average molecular weight of about 10,000 to 2 million, 10,000 to 1 million, 10,000 to 500,000, or 10,000 to 300,000. In the present application, the term weight average molecular weight means a conversion value for standard polystyrene measured by gel permeation chromatography (GPC). However, the above-mentioned weight average molecular weight does not necessarily have to be a resin component. For example, a separate binder resin may be blended into the pressure-sensitive adhesive composition even when the molecular weight of the resin component does not become a level enough to form a film. As used herein, the term polymer and resin component may be used interchangeably.
As described above, the pressure-sensitive adhesive composition may include a curable resin. The curable resin according to the present application may be UV curable, but is not limited thereto and may be thermosetting. The curable resin may include at least one curable functional group. The curable functional group may be, for example, at least one selected from glycidyl group, isocyanate group, hydroxyl group, carboxyl group, amide group, epoxide group, cyclic ether group, sulfide group, acetal group and lactone group. The curable resin implements an appropriate degree of crosslinking in the pressure-sensitive adhesive to implement excellent heat resistance at high temperature and high humidity.
In one example, the curable resin may have a cyclic structure in which the ring constituent atoms are in the range of 3 to 10, 4 to 9, or 5 to 8 in the molecular structure, but are not limited thereto. In addition, the curable resin may have the annular structure even after the pressure-sensitive adhesive is cured. The cyclic structure may be alicyclic. The curable resin having the above structure may implement a crosslinked structure that is stable to external factors such as shrinkage and expansion even after the adhesive is crosslinked or cured.
In one example, the curable resin may be a cycloaliphatic epoxy compound or a curable oligomer including at least one cyclic ether group.
As examples of the cycloaliphatic epoxy compound, 3,4-epoxycyclohexylmethyl 3 ', 4'-epoxycyclohexanecarboxylate (EEC) and derivatives, dicyclopentadiene dioxides and derivatives, vinylcyclohexyl dioxides and derivatives, 1, 4-cyclohexanedimethanol bis (3,4-epoxycyclohexanecarboxylate) and derivatives, including but not limited to.
The curable oligomer may have a weight average molecular weight in the range of 500 to 100,000, 550 to 90,000, 600 to 80,000, 650 to 70,000 or 650 to 60,000. Within the above molecular weight range, the pressure-sensitive adhesive composition of the present application may be cured to have excellent moisture barrier properties, and may be excellent in heat resistance and adhesion.
Examples of the curable oligomer include EHPE3150, GT401, PB3600, PB4700, etc. manufactured by DAICEL. In addition, 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-epoxide), more specifically, molecular structure And cationically curable oligomers made through radical polymerization or the like using an ether group-containing monomer having a cyclic structure therein.
The curable resin is 20 to 100 parts by weight, 20 to 90 parts by weight, 20 to 80 parts by weight, 25 to 70 parts by weight, 25 to 60 parts by weight, 28 to 50 parts by weight based on 100 parts by weight of the polymer derived from isobutylene. Or it may be included in 28 to 40 parts by weight. The present application can be applied to the pressure-sensitive adhesive composition encapsulates the organic electronic device within the weight range, it can implement the durability reliability at high temperature and high humidity with excellent moisture barrier properties.
In one example, the pressure-sensitive adhesive composition of the present application may further include a tackifier. The tackifier may be a resin produced by the reaction of a terpene compound and an aromatic compound. When the tackifier has an aromatic in the molecular structure, it is possible to improve the compatibility between the above-described polymer having a low polarity and the curable resin having a high polarity. In addition, the aromatic compound may include a functional group capable of reacting. Examples of the functional group may include a hydroxy group, a carboxyl group, an amine group, and the like. The present application can improve the crosslinking density of the entire pressure-sensitive adhesive due to the reactive functional group. Specifically, the aromatic compound may be a phenol, the tackifier may be a terpene phenol-based resin. The present application, by using the terpene phenol-based resin as a tackifier, can increase not only excellent adhesion but also compatibility of the polymer and the curable resin, thereby improving the crosslinking density to provide a pressure-sensitive adhesive excellent in durability and reliability. have.
The tackifier may be a resin produced by the reaction of a terpene compound and a phenol compound. The terpene compound may refer to a compound having a basic skeleton (C 5 H 8 ) n to which two or more isoprene (C 5 H 8 ) are bonded. 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 α-pinene, β-pinene, δ-3-karene, 3-karen, D-limonene and dipentene. In addition, the phenolic compound is phenol, 4-t-butylphenol (para-tert-butylphenol (PTBP), 4-t-octylphenol (PTOP), 4-n-pentylphenol (para-n It may be at least one selected from the group consisting of -pentyl phenol (PNPP) and 4-n-hexyl phenol (PNHP).
The tackifier may be included in 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 weight range, the pressure-sensitive adhesive may be excellent in the compatibility of the polymer and the curable resin.
The tackifier may have, for example, a softening point in a range of 80 ° C to 150 ° C, 90 ° C to 145 ° C, 100 ° C to 140 ° C, or 104 ° C to 135 ° C. In addition, the tackifier has a weight average molecular weight in the range of 100 to 10,000, 200 to 9,000, 300 to 8,000 or 400 to 7,000, the glass transition temperature is 53 ℃ to 120 ℃, 55 ℃ to 110 ℃ or 60 ℃ to 100 It may be in the range of ℃. Within the above specific range, it is possible to prepare the pressure-sensitive adhesive having a degree of crosslinking density desired in the present application.
In an embodiment of the present application, the pressure-sensitive adhesive composition may include a hardening agent and a photoinitiator together. As mentioned above, the hardener can include a thermoset or a thermal initiator. A cation initiator can be used as an initiator, and a cationic photopolymerization initiator or a cationic thermal initiator can be used as a cation initiator.
As the thermosetting agent in the present application, as the epoxy curing agent known in the art, for example, one kind or two or more kinds such as amine curing agent, imidazole curing agent, phenol curing agent, phosphorus curing agent or acid anhydride curing agent may be used. It is not limited.
In one example, as the thermosetting agent, an imidazole compound which is solid at room temperature and has a melting point or decomposition temperature of 80 ° C. or more may be used. As such a compound, for example, 2-methyl imidazole, 2-heptadecyl imidazole, 2-phenyl imidazole, 2-phenyl-4-methyl imidazole or 1-cyanoethyl-2-phenyl imidazole, etc. This may be illustrated, but is not limited thereto.
As the cationic photopolymerization initiator, an onium salt or an organometallic salt-based ionizing cation initiator or an organosilane or a latent sulfonic acid-based or non-ionized cationic photopolymerization initiator may be used. Examples of the onium salt-based initiator include a diaryliodonium salt, a triarylsulfonium salt, an aryldiazonium salt, and the like. As the zero, iron arene and the like can be exemplified. Examples of the organosilane-based initiator include o-nitrobenzyl triaryl silyl ether and triaryl silyl peroxide. Or an acyl silane (acyl silane) may be exemplified, and the latent sulfuric acid-based initiator may be exemplified by α-sulfonyloxy ketone or α-hydroxymethylbenzoin sulfonate, but is not limited thereto. .
Cationic thermal initiators may include imidazole, quaternary ammonium salts of superacids (eg, quaternary ammonium salts of SbF 6 ), and the like and mixtures thereof.
In one example, the hardening agent and the photoinitiator may be included in 0.01 to 5 parts by weight and 0.01 to 10 parts by weight or 0.1 to 4 parts by weight and 0.1 to 8 parts by weight, respectively. In the above weight range, the pressure-sensitive adhesive composition according to the present application may realize excellent storage stability without phase separation, and may exhibit excellent crosslinking density after curing.
In this specification, unless otherwise specified, a unit "weight part" means the weight ratio between each component.
In addition to the above-described configuration, the pressure-sensitive adhesive composition according to the present application may include various additives depending on the use, the type of the resin component, and the manufacturing process of the pressure-sensitive adhesive layer described below, in a range that does not affect the effects of the above-described invention. For example, the pressure-sensitive adhesive composition may include a moisture adsorbent, an inorganic filler, a coupling agent, a crosslinking agent, a curable material, an ultraviolet stabilizer, an antioxidant, and the like in an appropriate range of contents depending on the desired physical properties.
The present application also relates to an adhesive film. The pressure-sensitive adhesive film may include an pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition described above. Although the structure of the adhesive film of this application is not specifically limited, For example, a base film or a release film (henceforth a "first film" may be called.); And the 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 said 1st film which can be used by this application is not specifically limited. In the present application, for example, a general polymer film of this field may be used as the first film. In the present application, for example, as the base material or the release film, a polyethylene terephthalate film, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a vinyl chloride copolymer film, a polyurethane film , Ethylene-vinyl acetate film, ethylene-propylene copolymer film, ethylene-ethyl acrylate copolymer film, ethylene-methyl acrylate copolymer film, polyimide film and the like can be used. In addition, an appropriate release treatment may be performed on one side or both sides of the base film or the release film of the present application. Alkyd-based, silicone-based, fluorine-based, unsaturated ester-based, polyolefin-based, or wax-based may be used as an example of the release agent used in the release treatment of the base film, and among these, it is preferable to use an alkyd-based, silicone-based or fluorine-based release agent Preferred, but not limited to.
Moreover, the kind of 2nd film (Hereinafter, a "cover film" may be called.) Which can be used by this application is not specifically limited, either. For example, in the present application, as the second film, the same or different kind as the first film can be used within the range illustrated in the above-described first film. In addition, in the present application, an appropriate release treatment may also be performed on the second film.
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 according to the following conditions in consideration of the use to which the film is applied. The adhesive layer included in the adhesive film of the present application may have a thickness of about 5 μm to 200 μm, preferably about 10 μm to 150 μm.
In addition, the adhesive film may have excellent light transmittance with respect to the visible light region. In one example, the adhesive film of the present application may 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. In addition, the adhesive film of the present application may 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 properties may be measured at 550nm using a UV-Vis Spectrometer.
The present application also provides a
In the present application, the organic electronic device may be an organic light emitting diode.
The organic electronic device may further include a protective film that protects the device on the organic electronic device.
The organic electronic device may further include a
The present application also relates to a method for manufacturing an organic electronic device, comprising the step of forming an adhesive film including the above-mentioned adhesive composition on another surface of a substrate on which an organic electronic device is formed on one surface. In one example, the manufacturing method may further comprise the step of crosslinking or curing the adhesive film.
In addition, the adhesive film may exhibit excellent transparency, and may be formed as a stable adhesive film regardless of the shape of the organic electronic device such as top emission or bottom emission.
As used herein, the term "curing" may mean that the pressure-sensitive adhesive composition of the present invention forms a crosslinked structure through a heating or UV irradiation step or the like to prepare a pressure-sensitive adhesive.
Specifically, a transparent electrode is formed on a glass or polymer film used as a substrate by vacuum deposition or sputtering, and a light emitting organic material composed of, for example, a hole transport layer, a light emitting layer, an electron transport layer, and the like on the transparent electrode. After the layer is formed, an electrode layer may be further formed on the organic electronic device.
Subsequently, the pressure-sensitive adhesive film may be placed on the other side of the substrate, and the pressure-sensitive adhesive film may be heated using a laminate group or the like to be pressed in a state in which fluidity is imparted, and the resin in the pressure-sensitive adhesive film may be crosslinked.
The present application can effectively block moisture or oxygen introduced into the organic electronic device from the outside, and provides a "glue adhesive composition" and a pressure-sensitive adhesive film that can implement not only the durability in harsh conditions such as high temperature and high humidity, but also excellent optical properties. .
1 is a cross-sectional view illustrating 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 examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the following examples.
Example One
10 g of polyisobutylene (Oppanol B80, BASF) was added to the mixed container as a polymer, and 35 parts by weight of an alicyclic epoxy compound (Celloxide 2021P, DAICEL) was used as a curable resin at 100 parts by weight based on 100 parts by weight of the polymer. Put into the container. In addition, a tackifier (DERTOPHENE T 115, DRT) was added to the container at 40 parts by weight based on 100 parts by weight of the polymer. Photoinitiator (Triarylsulfonium hexafluoroantimonate, Aldrich) was added to the container at 5 parts by weight based on 100 parts by weight of the solid content of the curable resin, and thermal initiator (SI-B3, Sanshin chemical) was added to the container at 1 part by weight based on 100 parts by weight of the solid content of the curable resin. Input.
A uniform pressure-sensitive adhesive composition solution (solvent: toluene) was prepared using a conventional mechanical stirrer as the mixing vessel.
The prepared solution was applied to the release surface of the release PET and dried in an oven at 130 ° C. for 3 minutes to prepare an adhesive film including an adhesive layer having a thickness of 30 μm. The physical properties of the sample obtained by irradiating ultraviolet light with 2 J / cm 2 (100 mW / cm 2 based on the A area) were measured.
Example 2
An adhesive composition and an adhesive film were prepared in the same manner as in Example 1, except that SI-B3A (Sanshin chemical) was used as the thermal initiator.
Example 3
An adhesive composition and an adhesive film were prepared in the same manner as in Example 1, except that SI-B2A (Sanshin chemical) was used as the thermal initiator.
Comparative example One
An adhesive composition and an adhesive film were prepared in the same manner as in Example 1, except that no thermal initiator was used.
One. Gel content Rate of change
[Formula 1]
Rate of change of gel content = (| G f -G i |) / G i × 100
[Formula 3]
Gel content (% by weight) = B / A × 100
In Formula 1, G i is the gel content immediately after coating the pressure-sensitive adhesive composition on a PET substrate, and G f means the gel content after vacuum-sealing the coated sample after coating in an aluminum pouch for 7 days at room temperature. .
In addition, in the general formula 3, A represents the mass of the pressure-sensitive adhesive composition, B is immersed in a network of 200 mesh (pore size 74㎛) after immersing the pressure-sensitive adhesive composition with toluene at 25 ℃ for 24 hours, the network The dry mass of the insoluble content of the adhesive composition which did not pass is shown.
Specifically, the gel content was measured by UV treatment of the coated adhesive, followed by Aging for 1 day to sufficiently cure, then sampling around 0.5g. After the sample was immersed in 100ml of toluene at 25 ℃ for 24 hours, filtered through a mesh of 200 mesh (pore size 74㎛), and dried in a 150 ℃ oven for at least 2 hours for insoluble content not passed through the network The weight was measured.
2. Creep
The base film which formed the adhesive layer of thickness 30micrometer containing the adhesive composition of an Example and a comparative example on one side was attached to the adhesion area 1cm <2> glass plate, aged for 24 hours, and the load of 1.5 kg at 25 degreeC was applied for 1000 second. When the pressure of the pressure-sensitive adhesive layer is changed between 50 seconds and 1000 seconds. The said base film is not specifically limited, For example, the polyethylene terephthalate (PET) film was used.
3. Moisture permeability
A glass substrate (70x70mm) and a face seal adhesive (Lace Chemical Co., Ltd.) are laminated, and a pressure-sensitive adhesive layer including the pressure-sensitive adhesive compositions of Examples and Comparative Examples is laminated on the face seal adhesive, and a barrier film (FTB3-50, 3M)) is laminated and cured by UV irradiation, and then aged at room temperature for 1 day (aging) and then measured the penetration length based on 500 hours at 85 ℃ and 85% relative humidity conditions.
The measurement results as described above 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 41wt%, and the gel content measured after 7 days of sealing was 37wt%. In addition, in Example 2, the gel content measured immediately after the coating of the pressure-sensitive adhesive was 40wt%, and the gel content measured after 7 days of sealing was 37wt%. In addition, in Example 3, the gel content measured immediately after the coating of the pressure-sensitive adhesive was 45 wt%, and the gel content measured after 7 days after sealing was 42 wt%. In addition, in the case of Comparative Example 1, the gel content measured immediately after coating of the pressure-sensitive adhesive was 43wt%, and the gel content measured after 7 days after sealing was 7wt%.
21: substrate
22: cover substrate
23: organic electronic device
24: adhesive film
12: Encapsulant
Claims (18)
The hardening agent is a pressure-sensitive adhesive composition comprising a thermal initiator or a thermosetting agent.
[Formula 1]
Rate of change of gel content = (| G f -G i |) / G i × 100
[Formula 2]
Gel content (% by weight) = B / A × 100
In Formula 1, G i is the gel content immediately after coating the pressure-sensitive adhesive composition on the PET substrate, G f means the gel content after vacuum-sealing the coated sample after the coating in an aluminum pouch for 7 days at room temperature ,
In Formula 2, A represents the mass of the pressure-sensitive adhesive composition, B is immersed in a mesh of 200 mesh (pore size 74㎛) after immersing the pressure-sensitive adhesive composition with toluene at 25 ℃ for 24 hours, do not pass through the network The dry mass of the insoluble content of the non-adhesive adhesive composition is shown.
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