KR20230123787A - Photocurable Composition, Encapsulation Layer and Display Device - Google Patents
Photocurable Composition, Encapsulation Layer and Display Device Download PDFInfo
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- KR20230123787A KR20230123787A KR1020220021005A KR20220021005A KR20230123787A KR 20230123787 A KR20230123787 A KR 20230123787A KR 1020220021005 A KR1020220021005 A KR 1020220021005A KR 20220021005 A KR20220021005 A KR 20220021005A KR 20230123787 A KR20230123787 A KR 20230123787A
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- KR
- South Korea
- Prior art keywords
- photocurable composition
- compound
- formula
- weight
- siloxane compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 238000005538 encapsulation Methods 0.000 title claims abstract description 30
- -1 siloxane compound Chemical class 0.000 claims abstract description 75
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000002834 transmittance Methods 0.000 abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 description 20
- 239000010408 film Substances 0.000 description 15
- 230000007547 defect Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 6
- 229910052755 nonmetal Inorganic materials 0.000 description 6
- 150000002843 nonmetals Chemical class 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 3
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YTZSKPAYFHSKOL-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)-2-[2-(2,3-dichlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl YTZSKPAYFHSKOL-UHFFFAOYSA-N 0.000 description 2
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- BVTLTBONLZSBJC-UHFFFAOYSA-N 2,4,6-tris(ethenyl)-2,4,6-trimethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O1 BVTLTBONLZSBJC-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- QIRUERQWPNHWRC-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(CC=2C=C3OCOC3=CC=2)=N1 QIRUERQWPNHWRC-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 1
- MCNPOZMLKGDJGP-QPJJXVBHSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MCNPOZMLKGDJGP-QPJJXVBHSA-N 0.000 description 1
- ZJRNXDIVAGHETA-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 ZJRNXDIVAGHETA-UHFFFAOYSA-N 0.000 description 1
- XOPKKHCDIAYUSK-UHFFFAOYSA-N 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound O1C(C)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 XOPKKHCDIAYUSK-UHFFFAOYSA-N 0.000 description 1
- PNDRGJCVJPHPOZ-UHFFFAOYSA-N 2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=CC=2OC=CC=2)=N1 PNDRGJCVJPHPOZ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- IJBSPUKPEDBNKQ-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-prop-1-en-2-ylphenyl)propan-1-one Chemical compound CC(=C)C1=CC=C(C(=O)C(C)(C)O)C=C1 IJBSPUKPEDBNKQ-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- WYYQKWASBLTRIW-UHFFFAOYSA-N 2-trimethoxysilylbenzoic acid Chemical group CO[Si](OC)(OC)C1=CC=CC=C1C(O)=O WYYQKWASBLTRIW-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- BLLOXKZNPPDLGM-UHFFFAOYSA-N 4-[2-[4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl]ethenyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 BLLOXKZNPPDLGM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 광경화성 모노머, 실록산 화합물, 실세스퀴옥산 화합물 및 광중합 개시제를 포함하고, 상기 광경화성 모노머로서 특정 구조의 아크릴계 광경화성 모노머의 조합을 포함하며, 상기 실록산 화합물로서 특정 구조의 실록산 화합물을 포함하는 광경화성 조성물, 이의 경화물을 포함하는 봉지층 및 상기 봉지층을 포함하는 화상표시장치를 제공한다. 본 발명에 따른 광경화성 조성물은 광투과도가 우수하고, 우수한 기계적 특성을 가지면서도 유전율이 낮을 뿐만 아니라 유기발광소자의 수명을 개선할 수 있다.The present invention includes a photocurable monomer, a siloxane compound, a silsesquioxane compound, and a photopolymerization initiator, and a combination of an acrylic photocurable monomer having a specific structure as the photocurable monomer, and a siloxane compound having a specific structure as the siloxane compound. It provides an image display device including a photocurable composition comprising, an encapsulation layer including a cured product thereof, and the encapsulation layer. The photocurable composition according to the present invention has excellent light transmittance, excellent mechanical properties, low permittivity, and can improve the lifespan of an organic light emitting device.
Description
본 발명은 광경화성 조성물, 봉지층 및 화상표시장치에 관한 것으로, 보다 상세하게는 광투과도가 우수하고, 우수한 기계적 특성을 가지면서도 유전율이 낮을 뿐만 아니라 유기발광소자의 수명을 개선할 수 있는 광경화성 조성물, 이의 경화물을 포함하는 봉지층 및 상기 봉지층을 포함하는 화상표시장치에 관한 것이다.The present invention relates to a photocurable composition, an encapsulation layer, and an image display device, and more particularly, to a photocurable composition that has excellent light transmittance, excellent mechanical properties, low permittivity, and can improve the lifespan of an organic light emitting device. It relates to a composition, an encapsulation layer containing a cured product thereof, and an image display device including the encapsulation layer.
액정표시장치(liquid crystal display, LCD), 플라즈마 디스플레이 장치(plasma display panel, PDP)에 이어 유기발광소자(organic light emitting deivce, OLED)는 주목받고 있는 차세대 디스플레이 장치이다. 이러한 유기발광소자는 기판 상에 양전극, 유기물층, 음전극을 순서대로 형성하고, 양전극과 음전극 사이에 전압을 걸어 줌으로써 전자와 정공이 각각 유기물층으로 이동한 후 재결합하여 빛을 발생시키는 방식이다.Following liquid crystal display (LCD) and plasma display panel (PDP), organic light emitting device (OLED) is a next-generation display device that is attracting attention. Such an organic light emitting device is a method in which a positive electrode, an organic material layer, and a negative electrode are sequentially formed on a substrate, and a voltage is applied between the positive electrode and the negative electrode to allow electrons and holes to move to the organic material layer and recombine to generate light.
한편, 유기물은 수분 및 산소에 매우 취약하여 유기발광소자 내부로 수분 및/또는 산소가 침투하게 되면 소자의 수명을 감소시키는 요인으로 작용될 수 있다.On the other hand, organic matter is very vulnerable to moisture and oxygen, and when moisture and/or oxygen penetrates into the organic light emitting device, it may act as a factor reducing the lifespan of the device.
수명을 결정하는 손상에는 소자 내부로부터의 요인에 따른 손상인 내인성 손상과 외부 요인에 의한 손상인 외인성 손상이 있다. 내인성 손상의 경우, 발광 물질의 여기 상태, 전하 주입과 수송 특성 등에 관련하며, 외인성 손상은 불안전한 공정, 기체나 액체 등과의 불필요한 반응, 그리고 빛이나 열 등이 원인이 된다. 특히, 외인성 손상에는 수분과 산소와의 반응이 큰 영향을 미치며 다크 스팟(Dark Spot)이 발생하면서 시간이 경과함에 따라 점점 면적이 커져 소자의 수명을 악화시킨다.Damage that determines the lifetime includes endogenous damage, which is damage caused by factors from inside the device, and extrinsic damage, which is damage caused by external factors. In the case of endogenous damage, it is related to the excited state of the light emitting material, charge injection and transport characteristics, etc., and extrinsic damage is caused by an unstable process, unnecessary reaction with gas or liquid, and light or heat. In particular, the reaction between moisture and oxygen has a great influence on extrinsic damage, and dark spots are generated, which gradually increase in area over time, deteriorating the lifespan of the device.
이에, 유기발광층을 외부 환경으로부터 보호하는 봉지기술이 매우 중요하다.Accordingly, an encapsulation technique for protecting the organic light emitting layer from the external environment is very important.
종래 유기발광층 봉지용 조성물에 수분 차단을 위하여 수분과의 친화성이 없고 발수성이 뛰어난 실록산 화합물을 사용하는 방안이 제시된 바 있다. 그런데, 이러한 실록산 화합물은 광경화성 모노머로서 주로 사용되는 아크릴계 모노머와의 상용성이 부족하여 도막화시 헤이즈가 발생하여 도막의 투과율을 저하시키는 문제점이 있었다(대한민국 공개특허 제10-2017-0045792호).A method of using a siloxane compound having no affinity for moisture and excellent water repellency in order to block moisture in a conventional organic light emitting layer encapsulation composition has been proposed. However, these siloxane compounds lack compatibility with acrylic monomers, which are mainly used as photocurable monomers, and thus have a problem in that haze occurs during coating, thereby reducing the transmittance of the coating (Korean Patent Publication No. 10-2017-0045792). .
따라서, 실록산 화합물과 아크릴계 모노머 간의 상용성을 높여 광투과도가 우수하고, 우수한 기계적 특성을 가지는 봉지층을 형성할 수 있는 조성물의 개발이 필요하다.Therefore, it is necessary to develop a composition capable of forming an encapsulation layer having excellent light transmittance and excellent mechanical properties by increasing the compatibility between the siloxane compound and the acrylic monomer.
아울러, 화상표시장치의 고속화가 가능하도록 유전율이 낮을 뿐만 아니라 외부로부터 유입되는 수분, 산소를 효과적으로 차단하여 유기발광소자의 수명을 더욱 개선할 수 있는 방안의 개발이 요구되고 있다.In addition, it is required to develop a method capable of further improving the lifespan of an organic light emitting device by effectively blocking moisture and oxygen introduced from the outside as well as having a low permittivity so as to enable high-speed image display devices.
본 발명의 한 목적은 광투과도가 우수하고, 우수한 기계적 특성을 가지면서도 유전율이 낮을 뿐만 아니라 유기발광소자의 수명을 개선할 수 있는 광경화성 조성물을 제공하는 것이다.One object of the present invention is to provide a photocurable composition capable of improving the lifespan of an organic light emitting device as well as having excellent light transmittance, excellent mechanical properties and low dielectric constant.
본 발명의 다른 목적은 상기 광경화성 조성물의 경화물을 포함하는 봉지층을 제공하는 것이다.Another object of the present invention is to provide an encapsulation layer comprising a cured product of the photocurable composition.
본 발명의 또 다른 목적은 상기 봉지층을 포함하는 화상표시장치를 제공하는 것이다.Another object of the present invention is to provide an image display device including the encapsulation layer.
한편으로, 본 발명은 광경화성 모노머, 실록산 화합물, 실세스퀴옥산 화합물 및 광중합 개시제를 포함하고, On the other hand, the present invention includes a photocurable monomer, a siloxane compound, a silsesquioxane compound and a photopolymerization initiator,
상기 광경화성 모노머는 하기 화학식 1로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하며, The photocurable monomer includes a compound represented by Formula 1 and a compound represented by Formula 2 below,
상기 실록산 화합물은 하기 화학식 3으로 표시되는 화합물을 포함하는 광경화성 조성물을 제공한다.The siloxane compound provides a photocurable composition including a compound represented by Formula 3 below.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 식에서, In the above formula,
R1, R3 및 R7은 각각 독립적으로 수소 또는 메틸기이고, R 1 , R 3 and R 7 are each independently hydrogen or a methyl group;
R2는 C7-C30의 알킬기이며, R 2 is a C 7 -C 30 alkyl group;
R4, R5 및 R6은 각각 독립적으로 C1-C30의 알킬기이고, R 4 , R 5 and R 6 are each independently a C 1 -C 30 alkyl group;
Ra는 C1-C30의 알킬기이며, R a is a C 1 -C 30 alkyl group;
Rb는 아릴기이고, R b is an aryl group;
a 및 b는 각각 독립적으로 0 내지 250의 정수이다.a and b are each independently an integer of 0 to 250;
본 발명의 일 실시형태에서, 상기 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물의 혼합비는 중량 기준으로 30:70 내지 70:30일 수 있다.In one embodiment of the present invention, the mixing ratio of the compound represented by Formula 1 and the compound represented by Formula 2 may be 30:70 to 70:30 based on weight.
본 발명의 일 실시형태에서, 상기 광경화성 모노머는 광경화성 조성물 전체 100 중량%에 대하여 1 내지 30 중량%의 양으로 포함될 수 있다.In one embodiment of the present invention, the photocurable monomer may be included in an amount of 1 to 30% by weight based on 100% by weight of the total photocurable composition.
본 발명의 일 실시형태에 따른 광경화성 조성물은 a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물을 포함할 수 있다.The photocurable composition according to an embodiment of the present invention may include a high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500.
본 발명의 일 실시형태에 따른 광경화성 조성물은 a 및 b의 합이 1 내지 99의 정수인 저분자량의 실록산 화합물과, a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물을 포함할 수 있다.The photocurable composition according to an embodiment of the present invention may include a low molecular weight siloxane compound in which the sum of a and b is an integer of 1 to 99, and a high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500. there is.
본 발명의 일 실시형태에서, a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 30 내지 60 중량%의 양으로 포함될 수 있다.In one embodiment of the present invention, the high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500 may be included in an amount of 30 to 60% by weight based on 100% by weight of the total photocurable composition.
본 발명의 일 실시형태에서, 상기 실록산 화합물은 환형 실록산 화합물을 더 포함할 수 있다.In one embodiment of the present invention, the siloxane compound may further include a cyclic siloxane compound.
본 발명의 일 실시형태에서, 상기 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 30 내지 90 중량%의 양으로 포함될 수 있다.In one embodiment of the present invention, the siloxane compound may be included in an amount of 30 to 90% by weight based on 100% by weight of the total photocurable composition.
본 발명의 일 실시형태에서, 상기 실세스퀴옥산 화합물은 말단에 비닐기를 가지는 실세스퀴옥산 화합물을 포함할 수 있다.In one embodiment of the present invention, the silsesquioxane compound may include a silsesquioxane compound having a vinyl group at the terminal.
본 발명의 일 실시형태에서, 상기 실세스퀴옥산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 1 내지 25 중량%의 양으로 포함될 수 있다.In one embodiment of the present invention, the silsesquioxane compound may be included in an amount of 1 to 25% by weight based on 100% by weight of the total photocurable composition.
본 발명의 일 실시형태에 따른 광경화성 조성물은 용제를 1 중량% 이하의 양으로 포함할 수 있다.The photocurable composition according to an embodiment of the present invention may include a solvent in an amount of 1% by weight or less.
본 발명의 일 실시형태에 따른 광경화성 조성물은 유기발광소자 봉지용으로 사용될 수 있다.The photocurable composition according to an embodiment of the present invention may be used for encapsulation of an organic light emitting device.
다른 한편으로, 본 발명은 상기 광경화성 조성물의 경화물을 포함하는 봉지층을 제공한다.On the other hand, the present invention provides an encapsulation layer comprising a cured product of the photocurable composition.
또 다른 한편으로, 본 발명은 상기 봉지층을 포함하는 화상표시장치를 제공한다.On the other hand, the present invention provides an image display device including the encapsulation layer.
본 발명에 따른 광경화성 조성물은 광투과도가 우수하고, 우수한 기계적 특성을 가지면서도 유전율이 낮아 유기발광소자 봉지(encapsulation)용으로 유리하게 사용될 수 있다.The photocurable composition according to the present invention has excellent light transmittance, excellent mechanical properties, and low permittivity, so it can be advantageously used for encapsulation of an organic light emitting device.
또한, 본 발명의 일 실시형태에 따른 광경화성 조성물은 경화 후 우수한 기체 및 수분 배리어 특성을 가져 화소 불량을 방지할 수 있다.In addition, the photocurable composition according to an embodiment of the present invention has excellent gas and moisture barrier properties after curing, so that pixel defects can be prevented.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 일 실시형태는 광경화성 모노머(A), 실록산 화합물(B), 실세스퀴옥산 화합물(C) 및 광중합 개시제(D)를 포함하고, One embodiment of the present invention includes a photocurable monomer (A), a siloxane compound (B), a silsesquioxane compound (C) and a photopolymerization initiator (D),
상기 광경화성 모노머는 하기 화학식 1로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하며, The photocurable monomer includes a compound represented by Formula 1 and a compound represented by Formula 2 below,
상기 실록산 화합물은 하기 화학식 3으로 표시되는 화합물을 포함하는 광경화성 조성물에 관한 것이다.The siloxane compound relates to a photocurable composition including a compound represented by Formula 3 below.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 식에서, In the above formula,
R1, R3 및 R7은 각각 독립적으로 수소 또는 메틸기이고, R 1 , R 3 and R 7 are each independently hydrogen or a methyl group;
R2는 C7-C30의 알킬기이며, R 2 is a C 7 -C 30 alkyl group;
R4, R5 및 R6은 각각 독립적으로 C1-C30의 알킬기이고, R 4 , R 5 and R 6 are each independently a C 1 -C 30 alkyl group;
Ra는 C1-C30의 알킬기이며, R a is a C 1 -C 30 alkyl group;
Rb는 아릴기이고, R b is an aryl group;
a 및 b는 각각 독립적으로 0 내지 250의 정수이다.a and b are each independently an integer of 0 to 250;
본 발명의 일 실시형태에 따른 광경화성 조성물은 광경화성 모노머로서 특정 구조의 아크릴계 광경화성 모노머를 조합하여 사용하면서 특정 구조의 실록산 화합물을 사용하여 실록산 화합물의 함량이 높아도 상용성이 우수하여 헤이즈 및 투과율 특성뿐만 아니라 경도 특성도 우수하면서 동시에 실록산 화합물로 인한 발수성을 유지할 수 있어 유기발광소자 봉지(encapsulation)용으로 유리하게 사용될 수 있다.The photocurable composition according to an embodiment of the present invention uses a siloxane compound having a specific structure while using a combination of an acrylic photocurable monomer having a specific structure as a photocurable monomer, and has excellent compatibility even when the content of the siloxane compound is high, resulting in haze and transmittance. It can be advantageously used for encapsulation of an organic light emitting device because it can maintain water repellency due to a siloxane compound while having excellent hardness characteristics as well as properties.
본 발명의 일 실시형태에 따른 광경화성 조성물은 경화막의 유전율이 3.0 이하, 바람직하기로 2.8 이하일 수 있다.The photocurable composition according to an embodiment of the present invention may have a dielectric constant of 3.0 or less, preferably 2.8 or less.
상기 유전율(permittivity)은 전하 사이에 전기장이 작용할 때, 그 전하 사이의 매질이 전기장에 미치는 영향을 나타내는 물리적 단위로서, 매질이 저장할 수 있는 전하량으로 볼 수도 있다.The permittivity is a physical unit representing the effect of the medium between the charges on the electric field when an electric field acts between the charges, and can be regarded as the amount of charge that the medium can store.
본 발명의 일 실시형태에 따른 광경화성 조성물의 경화막의 유전율은 경화 후 8 ㎛ 두께의 경화막이 형성된 샘플에 대하여 후술하는 실험예에 기재된 방법에 따라 주파수 100kHz에서 측정한 값이다.The dielectric constant of the cured film of the photocurable composition according to an embodiment of the present invention is a value measured at a frequency of 100 kHz according to the method described in Experimental Examples for a sample having a cured film having a thickness of 8 μm after curing.
상기 경화막의 유전율은 상술한 바와 같이 3.0 이하, 예를 들어 1 초과 3.0 이하, 바람직하기로 1 초과 2.8 이하일 수 있다. 상기 경화막의 유전율이 3.0 초과이면 신호 속도가 늦어질 수 있다.As described above, the cured film may have a permittivity of 3.0 or less, for example greater than 1 and less than 3.0, preferably greater than 1 and less than 2.8. When the dielectric constant of the cured film exceeds 3.0, the signal speed may be slowed down.
본 발명의 일 실시형태에 따른 광경화성 조성물은 3.0 이하 수준의 저유전율을 가져 신호 속도를 늦추지 않아 화상표시장치의 고속화가 가능하다.The photocurable composition according to an embodiment of the present invention has a low permittivity of 3.0 or less, so that the speed of the image display device can be increased without slowing down the signal speed.
광경화성 모노머(A)Photocurable monomer (A)
본 발명의 일 실시형태에서, 상기 광경화성 모노머(A)는 광 및 후술하는 광중합 개시제의 작용으로 중합할 수 있는 화합물로서, 하기 화학식 1로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 필수 성분으로 포함한다.In one embodiment of the present invention, the photocurable monomer (A) is a compound that can be polymerized by the action of light and a photopolymerization initiator described below, and the compound represented by the following formula (1) and the compound represented by the following formula (2) are essential components. to include
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 식에서, In the above formula,
R1, R3 및 R7은 각각 독립적으로 수소 또는 메틸기이고, R 1 , R 3 and R 7 are each independently hydrogen or a methyl group;
R2는 C7-C30의 알킬기이며, R 2 is a C 7 -C 30 alkyl group;
R4, R5 및 R6은 각각 독립적으로 C1-C30의 알킬기이다.R 4 , R 5 and R 6 are each independently a C 1 -C 30 alkyl group.
본 명세서에서 사용되는 C7-C30의 알킬기는 탄소수 7 내지 30개로 구성된 직쇄형 또는 분지형의 탄화수소를 의미하며, 예를 들어 2-에틸헥실, 헵틸, 2-에틸헵틸, 옥틸, 노닐, 데실, 운데실, 도데실, 트리데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실, 스테아릴, 노나데실, 에이코사닐, 베헤닐 등이 포함되나 이에 한정되는 것은 아니다.As used herein, the C 7 -C 30 alkyl group refers to a straight-chain or branched hydrocarbon having 7 to 30 carbon atoms, and examples thereof include 2-ethylhexyl, heptyl, 2-ethylheptyl, octyl, nonyl, and decyl. , undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, nonadecyl, eicosanyl, behenyl, and the like.
본 명세서에서 사용되는 C1-C30의 알킬기는 탄소수 1 내지 30개로 구성된 직쇄형 또는 분지형의 탄화수소를 의미하며, 예를 들어 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 헥실, 2-에틸헥실, 헵틸, 2-에틸헵틸, 옥틸, 노닐, 데실, 운데실, 도데실, 트리데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실, 스테아릴, 노나데실, 에이코사닐, 베헤닐 등이 포함되나 이에 한정되는 것은 아니다.As used herein, the C 1 -C 30 alkyl group refers to a straight-chain or branched hydrocarbon having 1 to 30 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i -butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, 2-ethylheptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, nonadecyl, eicosanil, behenyl, and the like, but are not limited thereto.
상기 C7-C30의 알킬기 및 C1-C30의 알킬기는 한 개 또는 그 이상의 수소가 C1-C6의 알킬기, C2-C6의 알케닐기, C2-C6의 알키닐기, C3-C10의 사이클로알킬기, C3-C10의 헤테로사이클로알킬기, C3-C10의 헤테로사이클로알킬옥시기, C1-C6의 할로알킬기, C1-C6의 알콕시기, C1-C6의 티오알콕시기, 아릴기, 아실기, 히드록시, 티오(thio), 할로겐, 아미노, 알콕시카르보닐, 카르복시, 카바모일, 시아노, 니트로 등으로 치환될 수 있다.In the C 7 -C 30 alkyl group and C 1 -C 30 alkyl group, one or more hydrogen is a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, C 3 -C 10 cycloalkyl group, C 3 -C 10 heterocycloalkyl group, C 3 -C 10 heterocycloalkyloxy group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C It may be substituted with a 1 -C 6 thioalkoxy group, aryl group, acyl group, hydroxy, thio, halogen, amino, alkoxycarbonyl, carboxy, carbamoyl, cyano, nitro, or the like.
상기 화학식 1로 표시되는 화합물은 탄소수가 7 이상인 장쇄 알킬기를 가져 유전율을 낮출 수 있다.The compound represented by Chemical Formula 1 has a long-chain alkyl group having 7 or more carbon atoms and can lower dielectric constant.
대부분의 분자는 두 원자간 결합에서 전자쌍이 한 쪽으로 치우치는 극성을 가진 공유결합을 형성한다. 극성 결합은 분자 내에 쌍극자 모멘트(dipole moment)를 유발하는데, 전기장이 가해지면 이 쌍극자 모멘트가 전기장 방향에 따라 배열하며 쌍극자 분극(dipolar polarization)이 발생한다. 유전율은 유전체에 전압이 인가되었을 때 분자 내에 유기되는 (+) 전하와 (-) 전하의 편재, 즉 쌍극자 분극의 대소를 나타낸다. 분자 내에 극성을 가진 기가 도입되면 분극이 커져 유전율이 커지게 된다. 예를 들어, 분자 내의 C=O 결합은 분극률을 크게 하여 유전율을 상승시킨다. 유전손실도 유전율처럼 극성이 커지면 증가하는 경향이 있다. 화학식 1로 표시되는 화합물은 탄소수가 7 이상인 장쇄 알킬기를 가져 분자 내에서 극성이 상쇄되어 결과적으로 유전율을 낮추는 효과를 가진다.Most molecules form covalent bonds with polarity in which the pair of electrons are skewed to one side in the bond between two atoms. Polar bonding induces a dipole moment in a molecule. When an electric field is applied, the dipole moment is arranged in the direction of the electric field, and dipolar polarization occurs. Permittivity indicates the localization of (+) and (-) charges, that is, the magnitude of dipole polarization, which is induced in a molecule when a voltage is applied to a dielectric. When a polar group is introduced into a molecule, the polarization increases and the permittivity increases. For example, a C=O bond in a molecule increases the polarizability and increases the permittivity. Dielectric loss, like permittivity, tends to increase as polarity increases. The compound represented by Chemical Formula 1 has a long-chain alkyl group having 7 or more carbon atoms, so that polarity is offset in the molecule, resulting in an effect of lowering the dielectric constant.
본 발명의 일 실시형태에서, R2는 C7-C30의 알킬기, 바람직하기로 C10-C25의 알킬기이다. R2의 탄소수가 상기 범위인 경우, 저유전율 구현면에서 바람직하다.In one embodiment of the present invention, R 2 is a C 7 -C 30 alkyl group, preferably a C 10 -C 25 alkyl group. When the carbon number of R 2 is within the above range, it is preferable in terms of implementing a low permittivity.
상기 화학식 1로 표시되는 화합물의 구체예로는 도데실 (메타)아크릴레이트, 스테아릴 (메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 이소스테아릴(메타)아크릴레이트, 베헤닐(메타)아크릴레이트 등을 들 수 있다.Specific examples of the compound represented by Formula 1 include dodecyl (meth) acrylate, stearyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isostearyl (meth) acrylate, behenyl ( meta) acrylate; and the like.
상기 화학식 2로 표시되는 화합물은 경화도를 향상시키고 후술하는 실록산 화합물과의 상용성을 향상시키는 역할을 한다.The compound represented by Formula 2 serves to improve the degree of curing and compatibility with a siloxane compound described later.
상기 화학식 2로 표시되는 화합물의 구체예로는 다이옥산 글리콜 디아크릴레이트, 다이옥산 글리콜 디메타크릴레이트 등을 들 수 있다.Specific examples of the compound represented by Formula 2 include dioxane glycol diacrylate and dioxane glycol dimethacrylate.
본 발명의 일 실시형태에서, 상기 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물의 혼합비는 중량 기준으로 30:70 내지 70:30, 바람직하게는 40:60 내지 60:40일 수 있다. 상기 혼합비에서, 상기 화학식 1로 표시되는 화합물의 함량이 적으면 유전율이 높아질 수 있고, 상기 화학식 1로 표시되는 화합물의 함량이 많으면 경화도가 부족해지거나 상용성이 불량해질 수 있다.In one embodiment of the present invention, the mixing ratio of the compound represented by Formula 1 and the compound represented by Formula 2 may be 30:70 to 70:30, preferably 40:60 to 60:40, based on weight. In the mixing ratio, when the content of the compound represented by Formula 1 is small, the dielectric constant may be increased, and when the content of the compound represented by Formula 1 is large, curing degree may be insufficient or compatibility may be poor.
본 발명의 일 실시형태에서, 상기 광경화성 모노머는 광경화성 조성물 전체 100 중량%에 대하여 1 내지 30 중량%, 바람직하게는 10 내지 25 중량%의 양으로 포함될 수 있다. 상기 광경화성 모노머의 함량이 1 중량% 미만이면 경화도가 부족할 수 있고, 30 중량% 초과이면 화소 불량이 발생할 수 있다.In one embodiment of the present invention, the photocurable monomer may be included in an amount of 1 to 30% by weight, preferably 10 to 25% by weight based on 100% by weight of the total photocurable composition. If the content of the photocurable monomer is less than 1% by weight, the degree of curing may be insufficient, and if the content of the photocurable monomer is greater than 30% by weight, pixel defects may occur.
실록산 화합물(B)Siloxane compound (B)
본 발명의 일 실시형태에서, 상기 실록산 화합물(B)은 발수성을 나타내고 유전율을 낮추는 역할을 한다. 아울러, 상기 실록산 화합물(B)은 내열성도 매우 우수하여 수분, 산소와 같은 외부 환경에 취약한 OLED소재를 보호해주는 봉지재의 성분으로서 유리하게 사용될 수 있다.In one embodiment of the present invention, the siloxane compound (B) exhibits water repellency and serves to lower dielectric constant. In addition, the siloxane compound (B) has excellent heat resistance and can be advantageously used as a component of an encapsulant that protects an OLED material that is vulnerable to external environments such as moisture and oxygen.
상기 실록산 화합물(B)은 하기 화학식 3으로 표시되는 화합물을 포함한다.The siloxane compound (B) includes a compound represented by Formula 3 below.
[화학식 3][Formula 3]
상기 식에서, In the above formula,
Ra는 C1-C30의 알킬기이며, R a is a C 1 -C 30 alkyl group;
Rb는 아릴기이고, R b is an aryl group;
a 및 b는 각각 독립적으로 0 내지 250의 정수이다.a and b are each independently an integer of 0 to 250;
본 명세서에서 사용되는 아릴기는 아로메틱기와 헤테로아로메틱기 및 그들의 부분적으로 환원된 유도체를 모두 포함한다. 상기 아로메틱기는 5원 내지 15원의 단순 또는 융합 고리형이며, 헤테로아로메틱기는 산소, 황 또는 질소를 하나 이상 포함하는 아로메틱기를 의미한다. 대표적인 아릴기의 예로는 페닐, 나프틸, 피리디닐(pyridinyl), 푸라닐(furanyl), 티오페닐(thiophenyl), 인돌릴(indolyl), 퀴놀리닐(quinolinyl), 이미다졸리닐(imidazolinyl), 옥사졸릴(oxazolyl), 티아졸릴(thiazolyl), 테트라히드로나프틸 등이 있으나 이에 한정되는 것은 아니다.Aryl groups as used herein include both aromatic groups, heteroaromatic groups, and partially reduced derivatives thereof. The aromatic group is a 5- to 15-membered simple or fused ring, and the heteroaromatic group refers to an aromatic group containing at least one oxygen, sulfur, or nitrogen. Representative examples of aryl groups include phenyl, naphthyl, pyridinyl, furanyl, thiophenyl, indolyl, quinolinyl, imidazolinyl, oxazolyl, thiazolyl, tetrahydronaphthyl, etc., but are not limited thereto.
상기 화학식 3으로 표시되는 화합물은 측쇄에 알킬기를 갖는 반복단위와 측쇄에 아릴기를 갖는 반복단위를 동시에 포함하는 경우, 발수성 및 광경화성 모노머와의 상용성면에서 바람직하다.When the compound represented by Chemical Formula 3 includes both a repeating unit having an alkyl group on a side chain and a repeating unit having an aryl group on a side chain, it is preferable in terms of water repellency and compatibility with photocurable monomers.
본 발명의 일 실시형태에서, Ra는 바람직하기로 C1-C12의 알킬기, 더욱 바람직하기로 C1-C6의 알킬기, 가장 바람직하기로 메틸기일 수 있다. Ra가 C1-C12의 알킬기인 경우, 저점도 구현면에서 바람직하고, 이에 따라 제팅성이 개선될 수 있다.In one embodiment of the present invention, R a is preferably a C 1 -C 12 alkyl group, more preferably a C 1 -C 6 alkyl group, most preferably a methyl group. When R a is a C 1 -C 12 alkyl group, it is preferable in terms of low viscosity, and thus the jetting property can be improved.
본 발명의 일 실시형태에서, Rb는 바람직하기로 페닐기일 수 있다. Rb가 페닐기인 경우, 광경화성 모노머와의 상용성면에서 바람직하고, 이에 따라 헤이즈 및 투과율 특성뿐만 아니라 경도 특성도 우수하다.In one embodiment of the present invention, R b may preferably be a phenyl group. When R b is a phenyl group, it is preferable in terms of compatibility with the photocurable monomer, and thus has excellent hardness characteristics as well as haze and transmittance characteristics.
본 발명의 일 실시형태에 따른 광경화성 조성물은 a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물을 포함할 수 있다.The photocurable composition according to an embodiment of the present invention may include a high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500.
상기 고분자량의 실록산 화합물은 예를 들어 a 및 b의 합이 100 내지 450, 125 내지 450, 150 내지 400, 200 내지 400, 200 내지 350, 또는 200 내지 300일 수 있다.The high molecular weight siloxane compound may be, for example, 100 to 450, 125 to 450, 150 to 400, 200 to 400, 200 to 350, or 200 to 300 in the sum of a and b.
상기 고분자량의 실록산 화합물은 내열성 및 수분침투 방지특성이 매우 우수하다. 따라서, 본 발명의 일 실시형태에 따른 광경화성 조성물은 수분 및/또는 산소와 같은 외부 환경에 취약한 OLED 소재를 보호해주는 봉지층에 유리하게 사용될 수 있다.The high molecular weight siloxane compound has excellent heat resistance and water penetration prevention properties. Therefore, the photocurable composition according to an embodiment of the present invention can be advantageously used as an encapsulation layer that protects an OLED material vulnerable to external environments such as moisture and/or oxygen.
다른 한편으로, 본 발명의 일 실시형태에 따른 광경화성 조성물은 a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물 이외에, a 및 b의 합이 1 내지 99의 정수인 저분자량의 실록산 화합물을 추가로 포함할 수 있다. 상기 저분자량의 실록산 화합물은 조성물의 점도를 낮춰 제팅성을 개선할 수 있다.On the other hand, the photocurable composition according to an embodiment of the present invention is a low molecular weight siloxane compound in which the sum of a and b is an integer of 1 to 99 in addition to the high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500. may additionally be included. The low molecular weight siloxane compound may improve jetting properties by lowering the viscosity of the composition.
상기 저분자량의 실록산 화합물은 예를 들어 a 및 b의 합이 1 내지 90, 1 내지 70, 1 내지 50, 1 내지 30, 1 내지 20, 1 내지 15 또는 1 내지 10일 수 있다.In the low molecular weight siloxane compound, the sum of a and b may be 1 to 90, 1 to 70, 1 to 50, 1 to 30, 1 to 20, 1 to 15, or 1 to 10, for example.
본 발명의 일 실시형태에서, a 및 b의 합이 100 내지 500의 정수인 고분자량의 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 30 내지 60 중량%, 바람직하게는 40 내지 50 중량%의 양으로 포함될 수 있다. 상기 고분자량의 실록산 화합물의 함량이 상기 범위보다 적으면 화소 불량이 발생할 수 있고, 상기 범위를 초과하면 고점도로 인해 제팅성이 불량할 수 있다.In one embodiment of the present invention, the high molecular weight siloxane compound in which the sum of a and b is an integer of 100 to 500 is 30 to 60% by weight, preferably 40 to 50% by weight, based on 100% by weight of the total photocurable composition. can be included as If the content of the high molecular weight siloxane compound is less than the above range, pixel defects may occur, and if it exceeds the above range, jetting property may be poor due to high viscosity.
본 발명의 일 실시형태에서, a 및 b의 합이 1 내지 99의 정수인 저분자량의 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 1 내지 30 중량%의 양으로 포함될 수 있다. 상기 저분자량의 실록산 화합물의 함량이 1 중량% 미만이면 점도 조절이 어려울 수 있고, 30 중량% 초과이면 상술한 광경화성 모노머(A)와의 상용성이 불량해질 수 있다.In one embodiment of the present invention, the low molecular weight siloxane compound in which the sum of a and b is an integer of 1 to 99 may be included in an amount of 1 to 30% by weight based on 100% by weight of the entire photocurable composition. If the content of the low molecular weight siloxane compound is less than 1% by weight, it may be difficult to control the viscosity, and if it exceeds 30% by weight, compatibility with the above-described photocurable monomer (A) may be poor.
본 발명의 일 실시형태에서, 상기 실록산 화합물은 환형 실록산 화합물을 더 포함할 수 있다.In one embodiment of the present invention, the siloxane compound may further include a cyclic siloxane compound.
상기 환형 실록산 화합물은 하기 화학식 4로 표시되는 화합물을 포함할 수 있다.The cyclic siloxane compound may include a compound represented by Formula 4 below.
[화학식 4][Formula 4]
상기 식에서, In the above formula,
Rc 및 Rd는 각각 독립적으로 수소 원자, C1-C6의 알킬기 또는 C2-C6의 알케닐기이고, R c and R d are each independently a hydrogen atom, a C 1 -C 6 alkyl group or a C 2 -C 6 alkenyl group,
m은 2 내지 20의 정수이다.m is an integer from 2 to 20;
본 명세서에서 사용되는 C1-C6의 알킬기는 탄소수 1 내지 6개로 구성된 직쇄형 또는 분지형의 1가 탄화수소를 의미하며, 예를 들어 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, n-헥실 등이 포함되나 이에 한정되는 것은 아니다.As used herein, the C 1 -C 6 alkyl group refers to a straight-chain or branched monovalent hydrocarbon having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, i-propyl, and n-butyl. , i-butyl, t-butyl, n-pentyl, n-hexyl, and the like, but are not limited thereto.
본 명세서에서 사용되는 C2-C6의 알케닐기는 하나 이상의 탄소-탄소 이중결합을 갖는 탄소수 2 내지 6개로 구성된 직쇄형 또는 분지형 불포화 탄화수소를 의미하며, 예를 들어 에틸렌일, 프로펜일, 부텐일, 펜텐일 등이 포함되나 이에 한정되는 것은 아니다.As used herein, the C 2 -C 6 alkenyl group refers to a straight-chain or branched unsaturated hydrocarbon having 2 to 6 carbon atoms and having at least one carbon-carbon double bond, for example, ethyleneyl, propenyl, Thenyl, pentenyl, and the like are included, but are not limited thereto.
본 발명의 일 실시형태에서, m은 상기한 바와 같이 2 내지 20의 정수, 바람직하게는 3 내지 10의 정수이다.In one embodiment of the present invention, m is an integer from 2 to 20, preferably from 3 to 10 as described above.
예를 들어, 상기 환형 실록산 화합물로는 2,4,6-트리메틸-2,4,6-트리비닐시클로트리실록산, 2,4,6,8-테트라메틸시클로테트라실록산, 옥타메틸시클로테트라실록산, 2,4,6,8-테트라메틸-2,4,6,8-테트라비닐시클로테트라실록산, 데카메틸시클로펜타실록산, 도데카메틸시클로헥사실록산 등을 사용할 수 있으며, 이들은 단독으로 또는 2종 이상 조합하여 사용할 수 있다.For example, the cyclic siloxane compound includes 2,4,6-trimethyl-2,4,6-trivinylcyclotrisiloxane, 2,4,6,8-tetramethylcyclotetrasiloxane, octamethylcyclotetrasiloxane, 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc. may be used, and these may be used alone or in combination of two or more. Can be used in combination.
상기 환형 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 30 중량% 이하, 예를 들어 1 내지 25 중량%, 바람직하게는 2 내지 20 중량%의 양으로 포함될 수 있다. 상기 환형 실록산 화합물의 함량이 상기 범위이면 저점도 구현이 용이하며, 30 중량%를 초과하면 상술한 광경화성 모노머(A)와의 상용성이 불량해질 수 있다.The cyclic siloxane compound may be included in an amount of 30 wt% or less, for example, 1 to 25 wt%, preferably 2 to 20 wt%, based on 100 wt% of the total photocurable composition. When the content of the cyclic siloxane compound is in the above range, it is easy to implement a low viscosity, and when it exceeds 30% by weight, compatibility with the above-described photocurable monomer (A) may deteriorate.
본 발명의 일 실시형태에서, 상기 실록산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 30 내지 90 중량%, 바람직하게는 30 내지 70 중량%의 양으로 포함될 수 있다. 상기 실록산 화합물의 함량이 30 중량% 미만이면 화소 불량이 발생하거나 막경도가 부족할 수 있고, 90 중량% 초과이면 제팅성이 불량할 수 있다.In one embodiment of the present invention, the siloxane compound may be included in an amount of 30 to 90% by weight, preferably 30 to 70% by weight based on 100% by weight of the total photocurable composition. If the content of the siloxane compound is less than 30% by weight, pixel defects may occur or film hardness may be insufficient, and if the content of the siloxane compound is greater than 90% by weight, jetting property may be poor.
실세스퀴옥산 화합물(C)Silsesquioxane compound (C)
본 발명의 일 실시형태에서, 상기 실세스퀴옥산 화합물(C)은 벌키(bulky) 구조를 가져 공극을 형성하여 저유전성을 나타내고, 광투명성 및 경도를 향상시키는 역할을 한다. 즉, 상기 실세스퀴옥산 화합물(C)은 기계적, 전기적, 화학적 및 열적 특성이 우수하여 소자에 유용하게 적용될 수 있다.In one embodiment of the present invention, the silsesquioxane compound (C) has a bulky structure to form pores to exhibit low dielectric properties and improve light transparency and hardness. That is, the silsesquioxane compound (C) has excellent mechanical, electrical, chemical and thermal properties and can be usefully applied to devices.
상기 실세스퀴옥산 화합물은 말단에 비닐기를 가지는 실세스퀴옥산 화합물을 포함할 수 있다. 상기 말단에 비닐기를 가지는 실세스퀴옥산 화합물은 랜덤형, 케이지형 또는 사다리형일 수 있다. The silsesquioxane compound may include a silsesquioxane compound having a vinyl group at the terminal. The silsesquioxane compound having a vinyl group at the terminal may be random, cage or ladder type.
상기 말단에 비닐기를 가지는 실세스퀴옥산 화합물은 하기 화학식 5로 표시되는 화합물을 포함할 수 있다.The silsesquioxane compound having a vinyl group at the terminal may include a compound represented by Formula 5 below.
[화학식 5][Formula 5]
[(RSiO3/2)n][(RSiO 3/2 ) n ]
상기 식에서, In the above formula,
R은 각각 독립적으로 수소, 비닐기로 치환되거나 치환되지 않은 탄소수 1 내지 20의 지방족 탄화수소기, 또는 비닐기로 치환되거나 치환되지 않은 방향족 탄화수소기이며, 적어도 하나는 비닐기로 치환된 탄소수 1 내지 20의 지방족 탄화수소기, 또는 비닐기로 치환된 방향족 탄화수소기이고, R are each independently hydrogen, an aliphatic hydrocarbon group having 1 to 20 carbon atoms substituted or unsubstituted with a vinyl group, or an aromatic hydrocarbon group optionally substituted with a vinyl group, and at least one aliphatic hydrocarbon group having 1 to 20 carbon atoms substituted with a vinyl group. group, or an aromatic hydrocarbon group substituted with a vinyl group,
n은 1 내지 500의 정수이다.n is an integer from 1 to 500;
상기 말단에 비닐기를 가지는 실세스퀴옥산 화합물의 시판품으로는 예를 들어, VPR0600N (한국바이오젠 사), OL1170 (Hybrid Plastics 사) 등을 들 수 있다.Commercially available products of the silsesquioxane compound having a vinyl group at the terminal include, for example, VPR0600N (Korea Biogen) and OL1170 (Hybrid Plastics).
본 발명의 일 실시형태에서, 상기 실세스퀴옥산 화합물은 광경화성 조성물 전체 100 중량%에 대하여 1 내지 25 중량%, 바람직하게는 10 내지 25 중량%의 양으로 포함될 수 있다. 상기 실세스퀴옥산 화합물의 함량이 1 중량% 미만이면 경도가 저하되거나 유전율이 상승할 수 있고, 25 중량% 초과이면 상술한 광경화성 모노머(A)와의 상용성이 불량해질 수 있다.In one embodiment of the present invention, the silsesquioxane compound may be included in an amount of 1 to 25% by weight, preferably 10 to 25% by weight based on 100% by weight of the total photocurable composition. If the content of the silsesquioxane compound is less than 1% by weight, hardness may decrease or dielectric constant may increase, and if it exceeds 25% by weight, compatibility with the above-described photocurable monomer (A) may deteriorate.
광중합 개시제(D)Photopolymerization initiator (D)
본 발명의 일 실시형태에서, 상기 광중합 개시제(D)는 상기 광경화성 모노머를 중합시킬 수 있는 것이라면 그 종류를 특별히 제한하지 않고 사용할 수 있다. 특히, 상기 광중합 개시제(D)는 중합특성, 개시효율, 흡수파장, 입수성, 가격 등의 관점에서 아세토페논계 화합물, 벤조페논계 화합물, 트리아진계 화합물, 비이미다졸계 화합물, 옥심계 화합물, 티오크산톤계 화합물 및 아실포스핀옥사이드계 화합물로 이루어지는 군으로부터 선택되는 1종 이상의 화합물을 사용하는 것이 바람직하며, 특히 아실포스핀옥사이드계 화합물이 광경화도가 우수하고 아웃가스(outgas) 발생이 적어 바람직하다.In one embodiment of the present invention, as long as the photopolymerization initiator (D) can polymerize the photocurable monomer, its kind may be used without particular limitation. In particular, the photopolymerization initiator (D) is an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a biimidazole-based compound, an oxime-based compound, It is preferable to use at least one compound selected from the group consisting of thioxanthone-based compounds and acylphosphine oxide-based compounds, and in particular, acylphosphine oxide-based compounds have excellent photocurability and low outgas generation. desirable.
상기 아세토페논계 화합물의 구체적인 예로는 디에톡시아세토페논, 2-히드록시-2-메틸-1-페닐프로판-1-온, 벤질디메틸케탈, 2-히드록시-1-[4-(2-히드록시에톡시)페닐]-2-메틸프로판-1-온, 1-히드록시시클로헥실페닐케톤, 2-메틸-1-(4-메틸티오페닐)-2-모르폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)부탄-1-온, 2-히드록시-2-메틸-1-[4-(1-메틸비닐)페닐]프로판-1-온, 2-(4-메틸벤질)-2-(디메틸아미노)-1-(4-모르폴리노페닐)부탄-1-온 등을 들 수 있다. Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyl) Roxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1 -one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, etc. are mentioned.
상기 벤조페논계 화합물로서는, 예를 들면 벤조페논, o-벤조일벤조산 메틸, 4-페닐벤조페논, 4-벤조일-4'-메틸디페닐술피드, 3,3',4,4'-테트라(tert-부틸퍼옥시카르보닐)벤조페논, 2,4,6-트리메틸벤조페논 등이 있다. Examples of the benzophenone compound include benzophenone, o-methyl benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra ( tert-butyl peroxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.
상기 트리아진계 화합물의 구체적인 예로는 2,4-비스(트리클로로메틸)-6-(4-메톡시페닐)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시나프틸)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-피페로닐-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시스티릴)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(5-메틸퓨란-2-일)에테닐]-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(퓨란-2-일)에테닐]-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(4-디에틸아미노-2-메틸페닐)에테닐]-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(3,4-디메톡시페닐)에테닐]-1,3,5-트리아진 등을 들 수 있다. Specific examples of the triazine-based compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6 -(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2- yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl )-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine; and the like.
상기 비이미다졸계 화합물의 구체적인 예로는 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라(알콕시페닐)비이미다졸, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라(트리알콕시페닐)비이미다졸, 2,2-비스(2,6-디클로로페닐)-4,4',5,5'-테트라페닐-1,2'-비이미다졸 또는 4,4',5,5' 위치의 페닐기가 카르보알콕시기에 의해 치환되어 있는 비이미다졸 화합물 등을 들 수 있다. 이들 중에서 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2-비스(2,6-디클로로페닐)-4,4',5,5'-테트라페닐-1,2'-비이미다졸이 바람직하게 사용된다. Specific examples of the biimidazole-based compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3- Dichlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimi Dazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl)-4 , 4',5,5'-tetraphenyl-1,2'-biimidazole or a biimidazole compound in which the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group; and the like there is. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4' ,5,5'-tetraphenylbiimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole is preferred. used
상기 옥심계 화합물의 구체적인 예로는 o-에톡시카르보닐-α-옥시이미노-1-페닐프로판-1-온 등을 들 수 있으며, 시판품으로 바스프사의 Irgacure OXE 01, OXE 02가 대표적이다.Specific examples of the oxime-based compound include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, and Irgacure OXE 01 and OXE 02 commercially available from BASF are representative.
상기 티오크산톤계 화합물로서는, 예를 들면 2-이소프로필티오크산톤, 2,4-디에틸티오크산톤, 2,4-디클로로티오크산톤, 1-클로로-4-프로폭시티오크산톤 등이 있다.Examples of the thioxanthone-based compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like. there is
상기 아실포스핀옥사이드계 화합물로서는, 예를 들면 2,4,6-트리메틸벤조일디페닐포스핀옥사이드, 비스(2,4,6-트리메틸벤조일)-페닐포스핀옥사이드, 비스(2,6-디메톡시벤조일)-2,4,4-트리메틸-펜틸포스핀옥사이드 등을 들 수 있다. 시판품으로는, 바스프사의 이가큐어 TPO 등을 들 수 있다.Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and bis(2,6-dimethine). Toxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide etc. are mentioned. As a commercial item, BASF's Igacure TPO etc. are mentioned.
상기 광중합 개시제(D)는 광경화성 조성물 전체 100 중량%에 대하여 1 내지 10 중량%, 바람직하게는 1 내지 5 중량%의 양으로 포함될 수 있다. 상기 광중합 개시제가 상기 범위 내로 포함되는 경우 상기 광경화성 조성물이 고감도화되어 노광 시간이 단축되므로 생산성이 향상할 수 있기 때문에 바람직하다. 또한, 본 발명에 따른 광경화성 조성물을 사용하여 형성한 경화막의 강도와 상기 경화막의 표면에서의 평활성이 양호해지는 이점이 있다.The photopolymerization initiator (D) may be included in an amount of 1 to 10% by weight, preferably 1 to 5% by weight, based on 100% by weight of the total photocurable composition. When the photopolymerization initiator is included within the above range, the photocurable composition is highly sensitive and the exposure time is shortened, which is preferable because productivity can be improved. In addition, there is an advantage that the strength of the cured film formed using the photocurable composition according to the present invention and the smoothness on the surface of the cured film become good.
첨가제(E)Additive (E)
본 발명의 일 실시형태에 따른 광경화성 조성물은 상기한 성분들 이외에, 도막 평탄성 또는 밀착성을 증진시키기 위해서 계면활성제, 밀착촉진제와 같은 첨가제를 추가로 포함할 수 있다.In addition to the above components, the photocurable composition according to an embodiment of the present invention may further include additives such as a surfactant and an adhesion promoter in order to improve flatness or adhesion of a coating film.
본 발명에 따른 광경화성 조성물이 계면활성제를 포함하는 경우 도막 평탄성이 향상될 수 있는 이점이 있다. 예컨대 상기 계면활성제는 BM-1000, BM-1100(BM Chemie사), 프로라이드 FC-135/FC-170C/FC-430(스미토모 쓰리엠㈜), SH-28PA/-190/-8400/SZ-6032(도레 시리콘㈜), Efka FL 3600 (BASF사) 등의 불소계 계면 활성제를 사용할 수 있으나, 이에 한정되지는 않는다.When the photocurable composition according to the present invention includes a surfactant, there is an advantage in that coating film flatness can be improved. For example, the surfactant is BM-1000, BM-1100 (BM Chemie), Proride FC-135/FC-170C/FC-430 (Sumitomo 3M Co.), SH-28PA/-190/-8400/SZ-6032 (Tore Silicon Co., Ltd.), fluorine-based surfactants such as Efka FL 3600 (BASF) may be used, but are not limited thereto.
상기 밀착촉진제는 기판과의 밀착성을 높이기 위하여 첨가될 수 있는 것으로서 카르복실기, (메타)아크릴로일기, 이소시아네이트기, 에폭시기 및 이들의 조합으로 이루어진 군에서 선택되는 반응성 치환기를 갖는 실란 커플링제를 포함할 수 있으나 이에 한정되는 것은 아니다. 예컨대, 상기 실란 커플링제는 트리메톡시실릴 벤조산, γ-메타크릴옥시프로필 트리메톡시 실란, 비닐트리아세톡시실란, 비닐 트리메톡시실란, γ-이소시아네이트 프로필 트리에톡시실란, γ-글리시독시 프로필 트리메톡시실란, β-(3,4-에폭시시클로헥실)에틸트리메톡시실란 등을 들 수 있으며, 이들은 단독 또는 2종 이상 조합하여 사용할 수 있다.The adhesion promoter may be added to increase adhesion with a substrate, and may include a silane coupling agent having a reactive substituent selected from the group consisting of a carboxyl group, a (meth)acryloyl group, an isocyanate group, an epoxy group, and combinations thereof. However, it is not limited thereto. For example, the silane coupling agent is trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxy silane, vinyltriacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycidoxy propyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more.
이 외에도 본 발명에 따른 광경화성 조성물은 본 발명의 효과를 저해하지 않는 범위에서 산화 방지제, 자외선 흡수제, 응집 방지제와 같은 첨가제를 더 포함할 수도 있으며, 상기 첨가제는 역시 본 발명의 효과를 저해하지 않는 범위에서 당업자가 적절히 추가하여 사용이 가능하다.In addition, the photocurable composition according to the present invention may further include additives such as antioxidants, ultraviolet absorbers, and anti-aggregation agents within a range that does not impair the effects of the present invention, and the additives also do not impair the effects of the present invention. A person skilled in the art can appropriately add and use within the range.
상기 첨가제는 상기 광경화성 조성물 전체 100 중량%에 대하여 0.05 내지 10 중량%, 구체적으로 0.1 내지 10 중량%, 더욱 구체적으로 0.1 내지 5 중량%로 사용할 수 있으나 이에 한정되는 것은 아니다.The additive may be used in an amount of 0.05 to 10 wt%, specifically 0.1 to 10 wt%, and more specifically 0.1 to 5 wt%, based on 100 wt% of the photocurable composition, but is not limited thereto.
본 발명의 일 실시형태에 따른 광경화성 조성물은 용제를 실질적으로 포함하지 않으며, 포함하더라도 광경화성 조성물 전체 100 중량%에 대하여 10 중량% 이하의 양으로 포함한다. 본 발명의 일 실시형태에 따른 광경화성 조성물은 용제를 포함하지 않는 무용제형이거나 5 중량% 이하, 예컨대 1 중량% 이하로 포함하는 저용제형임에도 저점도 구현이 가능하다.The photocurable composition according to one embodiment of the present invention does not substantially include a solvent, and even if it includes a solvent, it is included in an amount of 10% by weight or less based on 100% by weight of the entire photocurable composition. The photocurable composition according to an embodiment of the present invention may be a non-solvent type that does not contain a solvent or a low-viscosity type containing less than 5% by weight, for example, less than 1% by weight.
또한, 본 발명의 일 실시형태에 따른 광경화성 조성물은 경화 후 우수한 기체 및 수분 배리어 특성을 가질 수 있다.In addition, the photocurable composition according to an embodiment of the present invention may have excellent gas and moisture barrier properties after curing.
아울러, 본 발명에 따른 광경화성 조성물은 향상된 경화도와 안정성을 가질 수 있다.In addition, the photocurable composition according to the present invention may have improved curing degree and stability.
본 발명의 일 실시형태는 상술한 광경화성 조성물의 경화물을 포함하는 봉지층에 관한 것이다.One embodiment of the present invention relates to an encapsulation layer comprising a cured product of the photocurable composition described above.
상기 봉지층은 장치용 부재를 밀봉함으로써 수분, 산소 등의 외부 환경에 의해 장치용 부재의 표면이 산화되거나 분해되는 것을 막는 역할을 한다.The sealing layer serves to prevent the surface of the device member from being oxidized or decomposed by an external environment such as moisture or oxygen by sealing the device member.
본 발명에 따른 광경화성 조성물의 패턴 형성 방법은, 상술한 광경화성 조성물을 잉크젯 방식으로 소정 영역에 도포하는 단계 및 상기 도포된 광경화성 조성물을 경화시키는 단계를 포함하여 이루어진다.The method of forming a pattern of a photocurable composition according to the present invention includes applying the above-described photocurable composition to a predetermined area by an inkjet method and curing the applied photocurable composition.
먼저, 본 발명의 광경화성 조성물을 잉크젯 분사기에 주입하여 장치용 부재의 소정 영역에 프린팅한다.First, the photocurable composition of the present invention is injected into an inkjet sprayer to print a predetermined area of a device member.
잉크젯 분사기의 일례인 피에조 잉크젯 헤드에서 분사되어 장치용 부재 위에서 적절한 상(phase)을 형성하기 위하여, 점도, 유동성 등의 특성이 잉크젯 헤드와 균형 있게 맞춰져야 한다. 본 발명에서 사용된 피에조 잉크젯 헤드는 제한되지 않으나, 약 10 내지 100pL, 바람직하게는 약 20 내지 40pL의 액적 크기를 가지는 잉크를 분사한다.In order to be ejected from a piezo inkjet head, which is an example of an inkjet injector, and form an appropriate phase on a member for a device, properties such as viscosity and fluidity must be balanced with the inkjet head. The piezo inkjet head used in the present invention is not limited, but ejects ink having a droplet size of about 10 to 100 pL, preferably about 20 to 40 pL.
본 발명의 일 실시형태는 상술한 봉지층을 포함하는 화상표시장치에 관한 것이다.One embodiment of the present invention relates to an image display device including the above-described encapsulation layer.
상기 화상표시장치는 장치용 부재, 및 상기 장치용 부재 상에 형성되고, 무기 봉지층과 유기 봉지층을 포함하는 장벽 스택을 포함할 수 있으며, 상기 유기 봉지층은 상술한 광경화성 조성물의 경화물을 포함한다.The image display device may include a device member and a barrier stack formed on the device member and including an inorganic encapsulation layer and an organic encapsulation layer, wherein the organic encapsulation layer is a cured product of the above-described photocurable composition. includes
상기 장치용 부재는 수분, 산소 등의 외부 환경에 노출시 분해 또는 산화되거나 성능이 저하될 수 있는 것으로서, 예를 들면 유기발광소자, 액정패널 등을 들 수 있다.The device member may be decomposed, oxidized, or degraded when exposed to an external environment such as moisture or oxygen, and may include, for example, an organic light emitting device or a liquid crystal panel.
상기 장치용 부재는 기판 상에 형성될 수 있다.The device member may be formed on a substrate.
상기 기판은 제한되지 않으며, 일례로 유리 기판, 실리콘 기판, 폴리카보네이트 기판, 폴리에스테르 기판, 방향족 폴리아미드 기판, 폴리아미드이미드 기판, 폴리이미드 기판, Al 기판, GaAs 기판 등의 표면이 평탄한 기판을 들 수 있다. 이들 기판은 실란 커플링제 등의 약품에 의한 약품 처리, 플라스마 처리, 이온 플레이팅 처리, 스퍼터링 처리, 기상반응 처리, 진공증착 처리 등의 전처리를 실시할 수 있다. 기판으로서 실리콘 기판 등을 사용하는 경우, 실리콘 기판 등의 표면에는 전하 결합소자(CCD), 박막 트랜지스터(TFT) 등이 형성될 수 있다. 또한, 격벽 매트릭스가 형성되어 있을 수도 있다.The substrate is not limited, and examples thereof include a substrate having a flat surface such as a glass substrate, a silicon substrate, a polycarbonate substrate, a polyester substrate, an aromatic polyamide substrate, a polyamideimide substrate, a polyimide substrate, an Al substrate, and a GaAs substrate. can These substrates can be subjected to pretreatment such as chemical treatment with a chemical such as a silane coupling agent, plasma treatment, ion plating treatment, sputtering treatment, vapor phase reaction treatment, and vacuum deposition treatment. When a silicon substrate or the like is used as the substrate, a charge coupled device (CCD), a thin film transistor (TFT), or the like may be formed on a surface of the silicon substrate or the like. Also, a barrier rib matrix may be formed.
상기 무기 봉지층은 유기 봉지층과 함께 수분, 산소 등의 외부 환경으로부터 장치용 부재를 보호하는 역할을 한다. 상기 무기 봉지층은 유기 봉지층과 성분이 서로 다르고, 무기 성분을 주성분으로 포함한다. 예를 들어, 상기 무기 봉지층은 실리콘(Si), 알루미늄(Al), 셀레늄(Se), 아연(Zn), 안티몬(Sb), 인듐(In), 게르마늄(Ge), 주석(Sn), 비스무트(Bi), 전이금속, 란탄족 금속 등의 금속 또는 비금속; 이들 금속 또는 비금속간의 화합물; 이들 금속 또는 비금속의 합금; 이들 금속 또는 비금속의 산화물; 이들 금속 또는 비금속의 질화물; 이들 금속 또는 비금속의 산질화물 등을 포함할 수 있다.The inorganic encapsulation layer together with the organic encapsulation layer serves to protect the device member from an external environment such as moisture and oxygen. The inorganic encapsulation layer has different components from the organic encapsulation layer, and includes an inorganic component as a main component. For example, the inorganic encapsulation layer may include silicon (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), and bismuth. (Bi), metals or non-metals such as transition metals and lanthanide metals; compounds between these metals or non-metals; alloys of these metals or nonmetals; oxides of these metals or nonmetals; nitrides of these metals or nonmetals; Oxynitrides of these metals or nonmetals may be included.
상기 화상표시장치는 유기발광장치(OLED), 액정표시장치(LCD), 전계발광표시장치(EL), 플라스마표시장치(PDP), 전계방출표시장치(FED) 등일 수 있으나 이에 한정되지 않는다. 특히, 상기 화상표시장치는 유기발광장치(OLED)일 수 있다.The image display device may be an organic light emitting device (OLED), a liquid crystal display (LCD), an electroluminescence display (EL), a plasma display (PDP), a field emission display (FED), but is not limited thereto. In particular, the image display device may be an organic light emitting device (OLED).
이하, 실시예, 비교예 및 실험예에 의해 본 발명을 보다 구체적으로 설명하고자 한다. 이들 실시예, 비교예 및 실험예는 오직 본 발명을 설명하기 위한 것으로, 본 발명의 범위가 이들에 국한되지 않는다는 것은 당업자에게 있어서 자명하다.Hereinafter, the present invention will be described in more detail by Examples, Comparative Examples and Experimental Examples. These Examples, Comparative Examples and Experimental Examples are only for explaining the present invention, and it is obvious to those skilled in the art that the scope of the present invention is not limited thereto.
실시예 및 비교예: 광경화성 조성물의 제조Examples and Comparative Examples: Preparation of photocurable composition
하기 표 1 및 표 2의 조성으로 각각의 성분들을 혼합하여 광경화성 조성물을 제조하였다(중량%).A photocurable composition was prepared by mixing the respective components according to the compositions shown in Tables 1 and 2 below (% by weight).
A-1: 부틸 아크릴레이트(TCI사)A-1: Butyl acrylate (TCI)
A-2: 베헤닐 아크릴레이트(A-BH, 신나카무라사)A-2: Behenyl acrylate (A-BH, Shin Nakamura Co.)
A-3: 스테아릴 아크릴레이트(TCI사)A-3: stearyl acrylate (TCI)
A-4: 다이옥산 글리콜 디아크릴레이트(A-DOG, 신나카무라사)A-4: Dioxane glycol diacrylate (A-DOG, Shin Nakamura Co., Ltd.)
A-5: 폴리에틸렌 글리콜 디아크릴레이트(A-200, 신나카무라사)A-5: Polyethylene glycol diacrylate (A-200, Shin Nakamura Co.)
A-6: 트리메틸올프로판 트리아크릴레이트(A-TMPT, 신나카무라사)A-6: Trimethylolpropane triacrylate (A-TMPT, Shin Nakamura Co., Ltd.)
A-7: 에톡실레이티드 펜타에리트리톨 테트라아크릴레이트(EO 4mol)(ATM-4E, 신나카무라사)A-7: ethoxylated pentaerythritol tetraacrylate (EO 4 mol) (ATM-4E, Shin Nakamura Co., Ltd.)
B-1: 1,3-디비닐테트라메틸디실록산(D1780, TCI사)B-1: 1,3-divinyltetramethyldisiloxane (D1780, manufactured by TCI)
B-2: 2,4,6,8-테트라메틸-2,4,6,8-테트라비닐사이클로테트라실록산(T2523, TCI사)B-2: 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane (T2523, manufactured by TCI)
B-3: PDV-0325(Gelest 사)B-3: PDV-0325 (Gelest)
B-4: 비닐 말단화 폴리(디메틸실록산)(433012, Aldrich사)B-4: vinyl-terminated poly(dimethylsiloxane) (433012, manufactured by Aldrich)
B-5: 히드록시 말단화 폴리(디메틸실록산)(481939, Aldrich사)B-5: hydroxy-terminated poly(dimethylsiloxane) (481939, Aldrich)
C-1: 실세스퀴옥산(VPR0600N, 한국바이오젠사)C-1: Silsesquioxane (VPR0600N, Korea Biogen)
D-1: 2,4,6-트리메틸벤조일디페닐포스핀옥사이드(TPO, BASF사)D-1: 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO, manufactured by BASF)
E-1: Efka FL 3600(BASF사)E-1: Efka FL 3600 (by BASF)
실험예: Experimental example:
상기 실시예 및 비교예에서 제조된 광경화성 조성물을 사용하여 하기 물성을 아래와 같은 방법으로 평가하고, 그 결과를 하기 표 3 및 표 4에 나타내었다.The following physical properties were evaluated using the photocurable compositions prepared in Examples and Comparative Examples in the following manner, and the results are shown in Tables 3 and 4 below.
<광경화막 형성방법><Method of forming photocuring film>
실시예 및 비교예에서 제조된 각각의 광경화성 조성물을 잉크젯 방식으로 유리 기판 위에 도포한 다음, UV 경화장치(Lichtzen사, Model No. LZ-UVC-F402-CMD)를 사용하여 150mW/㎠의 조도(UV-A 영역 320~400nm 기준)로 120초간 자외선을 조사하여 광경화막을 제조하였다.Each of the photocurable compositions prepared in Examples and Comparative Examples was applied on a glass substrate by an inkjet method, and then, using a UV curing device (Lichtzen, Model No. LZ-UVC-F402-CMD), an illuminance of 150 mW/cm 2 A photocured film was prepared by irradiating ultraviolet rays for 120 seconds (based on the UV-A region of 320 to 400 nm).
<OLED 단위 시편 제작 방법><How to manufacture OLED unit specimen>
ITO 패턴이 있는 기판 상에 유기발광소자(정공수송층 NPD/두께 600 Å, 발광층 Alq3/두께 700 Å, 전자주입층 LiF/두께 10 Å, 음극 Al + Liq/두께 1,000 Å)를 증착 적층 후, 제작된 소자에 실시예 및 비교예에 따른 봉지재를 상온 라미네이션한 후 녹색을 발광하는 OLED 단위 시편을 제작하였다.After depositing an organic light emitting device (Hole transport layer NPD / thickness 600 Å, light emitting layer Alq 3 / thickness 700 Å, electron injection layer LiF / thickness 10 Å, cathode Al + Liq / thickness 1,000 Å) on the substrate with the ITO pattern, After room temperature lamination of the encapsulant according to Examples and Comparative Examples on the manufactured device, an OLED unit specimen emitting green light was produced.
(1) 헤이즈(1) Haze
상기 제조된 광경화막에 대해 HM-150(Murakami사)로 헤이즈를 측정하고, 하기 평가 기준에 따라 평가하였다.The haze of the prepared photocurable film was measured with HM-150 (Murakami Co.), and evaluated according to the following evaluation criteria.
<평가 기준><Evaluation Criteria>
○: 0.2 미만○: less than 0.2
△: 0.2 이상 1 미만△: 0.2 or more and less than 1
×: 1 이상×: 1 or more
(2) 투과율(2) Transmittance
상기 제조된 광경화막에 대해 UV-2550(Shimadzu사)로 가시광선 영역(430nm)의 투과율을 측정하였다.The transmittance of the visible light region (430 nm) was measured with UV-2550 (Shimadzu Co.) for the prepared photocuring film.
(3) 연필 경도(3) pencil hardness
상기 제조된 광경화막의 연필 경도를 연필 경도 측정기를 이용하여 측정하였다. 구체적으로, 연필(미쓰비시사)을 광경화막에 접촉시킨 후, 1kg 하중 및 50mm/초의 속도로 표면을 긁어 표면 경도를 측정하였다.The pencil hardness of the prepared photocuring film was measured using a pencil hardness tester. Specifically, after bringing a pencil (Mitsubishi Co.) into contact with the photocured film, surface hardness was measured by scratching the surface at a load of 1 kg and a speed of 50 mm/sec.
(4) 유전율(4) Permittivity
보론(boron)으로 도핑(doping)된 P-타입의 실리콘 웨이퍼 상에 실시예 및 비교예에서 제조된 각각의 광경화성 조성물을 경화 후 두께가 8 ㎛가 되도록 코팅한 후, UV LED 395nm 하에서 노광 후 지름이 1mm로 설계된 하드마스크(hard mask)를 이용하여 1mm의 지름을 가지는 원형의 알루미늄 박막을 2000Å 두께로 증착하여 MIM(Metal-Insulator-Metal) 구조의 유전율 측정용 박막을 완성하였다. 이러한 박막을 프로브 스테이션(Micromanipulatior 6200 probe station)이 장착된 PRECISION LCR METER(HP4284A)를 이용하여 약 100kHz의 주파수에서 각각 정전용량(capacitance)을 측정하였다. 박막의 두께를 일립소미터로 측정한 후, 하기 수학식 1에 대입하여 유전율을 계산하였다.Each photocurable composition prepared in Examples and Comparative Examples was coated on a P-type silicon wafer doped with boron to have a thickness of 8 μm after curing, and then exposed under UV LED 395 nm. Using a hard mask designed to have a diameter of 1 mm, a circular aluminum thin film having a diameter of 1 mm was deposited to a thickness of 2000 Å to complete a thin film for measuring dielectric constant of a Metal-Insulator-Metal (MIM) structure. Capacitance of these thin films was measured at a frequency of about 100 kHz using a PRECISION LCR METER (HP4284A) equipped with a Micromanipulatior 6200 probe station. After measuring the thickness of the thin film with an ellipsometer, the permittivity was calculated by substituting it into Equation 1 below.
[수학식 1][Equation 1]
k = (C × A) / (εo × d)k = (C × A) / (ε o × d)
상기 식에서, k는 유전율(dielectric ratio), C는 정전용량(capacitance), εo는 진공의 유전상수(dielectric constant), d는 박막의 두께, A는 전극의 접촉 단면적을 나타낸다.In the above formula, k is the dielectric constant (dielectric ratio), C is the capacitance (capacitance), ε o is the dielectric constant of the vacuum (dielectric constant), d is the thickness of the thin film, A represents the contact cross-sectional area of the electrode.
(5) 화소 불량(5) Poor pixel
상기 제작된 OLED 단위 시편을 85℃, 상대 습도 85%의 환경에서 시간대별 발광부에서의 화소 불량 발생을 ×100의 디지털 현미경으로 100시간 단위로 관찰하여 화소 불량 발생 유무를 확인하고, 하기 평가 기준에 따라 평가하였다.The produced OLED unit specimen was observed every 100 hours with a digital microscope of × 100 for pixel defects in the light emitting part for each time period in an environment of 85 ° C and 85% relative humidity to confirm whether or not pixel defects occurred, and the following evaluation criteria evaluated according to
<평가 기준><Evaluation Criteria>
◎: 화소 불량 발생 소요시간이 1,000 시간 이상◎: The time required for pixel defects to occur is 1,000 hours or more
○: 화소 불량 소요시간이 1000시간 미만 ~ 800시간 이상○: The time required for pixel defects is less than 1000 hours to more than 800 hours
△: 화소 불량 소요시간이 800시간 미만 ~ 600시간 이상△: The time required for pixel defects is less than 800 hours to more than 600 hours
×: 화소 불량 소요시간이 600시간 미만×: The time required for pixel defects is less than 600 hours
상기 표 3 및 표 4에 나타낸 바와 같이, 본 발명에 따라 광경화성 모노머로서 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물을 포함하며, 실록산 화합물로서 화학식 3으로 표시되는 화합물을 포함하고, 실세스퀴옥산 화합물을 포함하는 실시예 1 내지 5의 광경화성 조성물은 광투과도가 우수하고, 우수한 기계적 특성을 가지면서도 유전율이 낮을 뿐만 아니라 화소 불량을 방지할 수 있는 것을 확인하였다.As shown in Tables 3 and 4, according to the present invention, a compound represented by Formula 1 and a compound represented by Formula 2 are included as photocurable monomers, and a compound represented by Formula 3 is included as a siloxane compound, It was confirmed that the photocurable compositions of Examples 1 to 5 including the sesquioxane compound had excellent light transmittance, excellent mechanical properties, low permittivity, and prevented pixel defects.
반면, 광경화성 모노머로서 화학식 1로 표시되는 화합물 및/또는 화학식 2로 표시되는 화합물을 포함하지 않거나, 실록산 화합물로서 화학식 3으로 표시되는 화합물을 포함하지 않거나, 실세스퀴옥산 화합물을 포함하지 않는 비교예 1 내지 4 및 7 내지 9의 광경화성 조성물은 광투과도, 기계적 특성, 유전율 특성 및 화소 불량 방지 특성을 동시에 확보할 수 없는 것으로 나타났다. 한편, 실록산 화합물로서 고분자량의 실록산 화합물을 특정 함량 범위로 포함하지 않는 비교예 5 및 6의 광경화성 조성물은 화소 불량이 발생하는 것으로 나타났다.On the other hand, a comparison that does not include the compound represented by Formula 1 and/or Formula 2 as a photocurable monomer, does not include the compound represented by Formula 3 as a siloxane compound, or does not include a silsesquioxane compound. It was found that the photocurable compositions of Examples 1 to 4 and 7 to 9 could not simultaneously secure light transmittance, mechanical properties, dielectric constant properties, and pixel defect prevention properties. On the other hand, it was found that the photocurable compositions of Comparative Examples 5 and 6, which did not contain a high molecular weight siloxane compound in a specific content range as a siloxane compound, caused pixel defects.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 본 발명이 속한 기술분야에서 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아님은 명백하다. 본 발명이 속한 기술분야에서 통상의 지식을 가진 자라면 상기 내용을 바탕으로 본 발명의 범주 내에서 다양한 응용 및 변형을 행하는 것이 가능할 것이다.Having described specific parts of the present invention in detail above, it is clear that these specific techniques are only preferred embodiments for those skilled in the art to which the present invention belongs, and the scope of the present invention is not limited thereto. do. Those skilled in the art to which the present invention pertains will be able to make various applications and modifications within the scope of the present invention based on the above information.
따라서, 본 발명의 실질적인 범위는 첨부된 특허청구범위와 그의 등가물에 의하여 정의된다고 할 것이다.Accordingly, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.
Claims (14)
상기 광경화성 모노머는 하기 화학식 1로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하며,
상기 실록산 화합물은 하기 화학식 3으로 표시되는 화합물을 포함하는 광경화성 조성물:
[화학식 1]
[화학식 2]
[화학식 3]
상기 식에서,
R1, R3 및 R7은 각각 독립적으로 수소 또는 메틸기이고,
R2는 C7-C30의 알킬기이며,
R4, R5 및 R6은 각각 독립적으로 C1-C30의 알킬기이고,
Ra는 C1-C30의 알킬기이며,
Rb는 아릴기이고,
a 및 b는 각각 독립적으로 0 내지 250의 정수이다.Including a photocurable monomer, a siloxane compound, a silsesquioxane compound and a photopolymerization initiator,
The photocurable monomer includes a compound represented by Formula 1 and a compound represented by Formula 2 below,
The siloxane compound is a photocurable composition comprising a compound represented by Formula 3:
[Formula 1]
[Formula 2]
[Formula 3]
In the above formula,
R 1 , R 3 and R 7 are each independently hydrogen or a methyl group;
R 2 is a C 7 -C 30 alkyl group;
R 4 , R 5 and R 6 are each independently a C 1 -C 30 alkyl group;
R a is a C 1 -C 30 alkyl group;
R b is an aryl group;
a and b are each independently an integer of 0 to 250;
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