CN110872365B - Composition for encapsulating organic light emitting diode and organic light emitting diode display - Google Patents
Composition for encapsulating organic light emitting diode and organic light emitting diode display Download PDFInfo
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- CN110872365B CN110872365B CN201910806782.0A CN201910806782A CN110872365B CN 110872365 B CN110872365 B CN 110872365B CN 201910806782 A CN201910806782 A CN 201910806782A CN 110872365 B CN110872365 B CN 110872365B
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 239000012044 organic layer Substances 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 35
- 239000003999 initiator Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 6
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- WBELHNUIWMNAFH-UHFFFAOYSA-N 12-prop-2-enoyloxydodecyl prop-2-enoate Chemical group C=CC(=O)OCCCCCCCCCCCCOC(=O)C=C WBELHNUIWMNAFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 238000005538 encapsulation Methods 0.000 abstract description 20
- 238000001020 plasma etching Methods 0.000 abstract description 10
- 230000000903 blocking effect Effects 0.000 abstract description 9
- -1 cyano, imino Chemical group 0.000 description 89
- 239000010410 layer Substances 0.000 description 44
- 229910052739 hydrogen Inorganic materials 0.000 description 37
- 239000001257 hydrogen Substances 0.000 description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
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- 239000000460 chlorine Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 229910052755 nonmetal Inorganic materials 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
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- 238000004821 distillation Methods 0.000 description 6
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
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- 230000004888 barrier function Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 150000002843 nonmetals Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- YJOWMBICANYBLV-UHFFFAOYSA-N 1-methyl-2-phenylindole-3-carbaldehyde Chemical compound O=CC=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 YJOWMBICANYBLV-UHFFFAOYSA-N 0.000 description 2
- BCQHHYHGZQLDLH-UHFFFAOYSA-N 2-(2-cyanoacetyl)oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)CC#N BCQHHYHGZQLDLH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000001204 arachidyl 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])[H] 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
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- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
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- 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 2
- 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 2
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- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- SBURHUAIGVFSSI-UHFFFAOYSA-N bis(dimethylsilyloxy)-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O[SiH](C)C)(O[SiH](C)C)C1=CC=CC=C1 SBURHUAIGVFSSI-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 229910052805 deuterium Inorganic materials 0.000 description 1
- NXGAOFONOFYCNG-UHFFFAOYSA-N diphenylphosphorylmethylbenzene Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)CC1=CC=CC=C1 NXGAOFONOFYCNG-UHFFFAOYSA-N 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
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- 125000006038 hexenyl group Chemical group 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 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 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 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 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
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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
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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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
- C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
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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
- 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
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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
- 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
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/20—Esters containing oxygen in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- 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
- H10K50/844—Encapsulations
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The present invention provides a composition for encapsulating an organic light emitting diode and an organic light emitting diode display including an organic layer formed of the composition. The composition comprises: and (2) component A: at least one of a compound of formula 1, a compound of formula 2, and a compound of formula 3; and (B) component: at least one selected from the group consisting of a non-silicone-based photocurable multifunctional monomer and a silicone-based photocurable multifunctional monomer; and (3) component C: a photocurable monofunctional monomer; and a component D: an initiator, wherein at least one selected from the group consisting of the compound of formula 1, the compound of formula 2, and the compound of formula 3 is present in an amount of 0.01 to 10 parts by weight, based on 100 parts by weight of the total of the component a, the component B, the component C, and the component D. Wherein the definitions of formula 1, formula 2 and formula 3 are the same as those defined in the detailed description. The encapsulation composition of the present invention can realize an organic layer having a good ultraviolet blocking effect and a low plasma etching rate.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims the right of korean patent application No. 10-2018-0103066, which was filed by the korean intellectual property office at 30/8 in 2018, the entire disclosure of which is incorporated herein by reference.
Technical Field
The present invention relates to a composition for encapsulating an organic light emitting diode and an organic light emitting diode display including an organic layer formed using the same.
Background
The organic light emitting diode is easily damaged when it comes into contact with external moisture or oxygen, and the reliability is lowered due to the loss of its function. Therefore, the organic light emitting diode must be encapsulated with a composition for encapsulating the organic light emitting diode.
On the other hand, when exposed to sunlight, the organic light emitting diode may be damaged by Ultraviolet (UV) light, resulting in a shortened lifetime thereof. In particular, since the organic light emitting diode used in a vehicle is exposed to sunlight for a long time, ultraviolet ray damage becomes an important problem of the organic light emitting diode. In order to block ultraviolet light, the polarizing plate and the adhesive formed on the organic light emitting diode may include an ultraviolet absorber. However, it is more effective to form an organic layer to be placed adjacent to the organic light emitting diode to prevent the organic light emitting diode from being damaged by blocking ultraviolet light from sunlight.
Generally, an encapsulation layer suitable for encapsulating an organic light emitting diode has a multi-layer structure including an inorganic layer and an organic layer. The inorganic layers and the organic layers have different properties and may be alternately stacked on top of each other to improve protection of the organic light emitting diode.
Disclosure of Invention
An object of the present invention is to provide a composition for encapsulating an organic light emitting diode, which can form an organic layer having a good ultraviolet blocking effect.
It is another object of the present invention to provide a composition for encapsulating an organic light emitting diode, which can realize an organic layer having a low plasma etching rate.
According to one aspect of the present invention, a composition for encapsulating an organic light emitting diode includes: and (2) component A: at least one of a compound of formula 1, a compound of formula 2, and a compound of formula 3; and (B) component: at least one of a non-silicone-based photocurable multifunctional monomer and a silicone-based photocurable multifunctional monomer; and (3) component C: a photocurable monofunctional monomer; and a component D: an initiator, wherein at least one of the compound of formula 1, the compound of formula 2, and the compound of formula 3 is present in an amount of 0.01 to 10 parts by weight, based on 100 parts by weight of the total of the component A, the component B, the component C), and the component D:
< formula 1>
Wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10And n is the same as defined in the following description of the present invention.
< formula 2>
Wherein R is20、R21And R22As defined in the following description of the invention.
< formula 3>
Wherein R is1、R2、R3And R4As defined in the following description of the invention.
According to another aspect of the present invention, there is provided an organic light emitting diode display including an organic layer formed using the composition for encapsulating an organic light emitting diode according to the present invention.
The present invention provides a composition for encapsulating an organic light emitting diode, which can form an organic layer having a good ultraviolet blocking effect.
The present invention provides a composition for encapsulating an organic light emitting diode, which can realize an organic layer having a low plasma etching rate.
Drawings
Fig. 1 is a cross-sectional view of an organic light emitting diode display according to one embodiment of the present invention.
Fig. 2 is a cross-sectional view of an organic light emitting diode display according to another embodiment of the present invention.
[ description of symbols ]
10: substrate
20: organic light emitting diode
30: barrier stack
31: inorganic layer
32: organic layer
40: inner space
100. 200: organic light emitting diode display
Detailed Description
Embodiments of the present invention will be described in detail with reference to the accompanying drawings to provide a thorough understanding of the invention to those skilled in the art. It is to be understood that the present invention may be embodied in various forms and is not limited to the following examples. In the drawings, portions irrelevant to the description will be omitted for clarity, and the same components will be denoted by the same reference numerals throughout the specification.
The term "(meth) acrylic-based" as used herein refers to acrylic-based and/or methacrylic-based.
Herein, unless otherwise stated, the term "substituted" means that at least one hydrogen atom of a functional group is substituted by: halogen (e.g. F, Cl, Br or I), hydroxy, nitro, cyano, imino (═ NH, ═ NR, where R is C1To C10Alkyl), amino (-NH)2-NH (R '), -N (R') (R '), wherein R', R 'and R' are each independently C1To C10Alkyl), amidino, hydrazine or hydrazone groups, carboxyl groups, C1To C20Alkyl radical, C6To C30Aryl radical, C3To C30Cycloalkyl radical, C3To C30Heteroaryl or C2To C30A heterocycloalkyl group.
Herein, the term "aryl" refers to a functional group in which all elements of a cyclic substituent have p orbitals and these p orbitals form a conjugate. Aryl groups include monocyclic, non-fused polycyclic and fused polycyclic functional groups. As used herein, the term "fused" means that a pair of carbon atoms are shared by adjoining rings. The aryl group also includes biphenyl group (biphenyl group), terphenyl group (terphenyl group), quaterphenyl group (quaterphenyl group), and the like, in which at least two aryl groups are connected to each other by a sigma bond. The aryl group can be phenyl, naphthyl, anthryl, phenanthryl, pyrenyl,
And the like.
As used herein, "alkyleneoxy" may include all functional groups in which at least one alkylene group is attached to at least one oxygen atom. For example, alkyleneoxy groups may include (alkylene-oxy)nAlkylene, (alkylene-oxy-alkylene)nAlkylene, alkylene-oxy or- (oxy-alkylene)n- (where n is an integer from 1 to 10).
According to one embodiment, a composition for encapsulating an organic light emitting diode includes: and (2) component A: at least one of a compound of formula 1, a compound of formula 2, and a compound of formula 3; and (B) component: at least one of a non-silicone-based photocurable multifunctional monomer and a silicone-based photocurable multifunctional monomer; and (3) component C: a photocurable monofunctional monomer; and a component D: an initiator, wherein at least one of the compound of formula 1, the compound of formula 2, and the compound of formula 3 is present in an amount of 0.01 to 10 parts by weight, based on 100 parts by weight of the total of the component A, the component B, the component C, and the component D. Within this content range, the encapsulation composition may reduce light transmittance at a wavelength of 420nm (nanometers), preferably at a wavelength of 410nm, more preferably at a wavelength of 405nm, thereby preventing external ultraviolet light from damaging the organic light emitting diode while improving plasma resistance (plasma resistance). Preferably, at least one of the compound of formula 1, the compound of formula 2, and the compound of formula 3 may be present in an amount of 1 to 10 parts by weight, 1 to 8 parts by weight, 3 to 8 parts by weight, such as 0.01 parts by weight, 0.1 parts by weight, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, or 10 parts by weight, based on 100 parts by weight of the total of the component a, the component B, the component C, and the component D.
Hereinafter, each component of the encapsulating composition according to the present invention will be described in detail.
(A-1) Compound of formula 1
The composition for encapsulating an organic light emitting diode according to the present invention may include the compound of formula 1.
< formula 1>
Wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9And R10Are identical or different from one another and are each independently hydrogen, substituted or unsubstituted C1To C10Alkyl, substituted or unsubstituted C6To C10Aryl, amino, halogen, cyano, nitro, a group of formula 1-1, a group of formula 1-2, a group of formula 1-3, or C having a hydroxyl group1To C10Alkyl groups:
< formula 1-1>
< formulas 1 and 2>
< formulas 1 to 3>
Wherein denotes the attachment site of an aromatic carbon of said compound of formula 1,
R11is hydrogen or substituted or unsubstituted C1To C5An alkyl group, a carboxyl group,
R12is a single bond, substituted or unsubstituted C1To C10Alkylene or substituted or unsubstituted C6To C20An arylene group, a cyclic or cyclic alkylene group,
R13、R14and R15Are the same or different from each other and are each independently substituted or unsubstituted C1To C10Alkylene or substituted or unsubstituted C6To C20Arylene radical, and
X1and X2Are identical to or different from each other and are each independently O, S or NR (R is hydrogen or substituted or unsubstituted C1To C5An alkyl group),
m is an integer of 1 to 6, and
n is an integer of 1 to 6.
Preferably, R1、R2、R3、R4、R5、R6、R7、R8、R9And R10At least one of which is a group of formula 1-1, formula 1-2 or formula 1-3.
In one embodiment, the compound of formula 1 may be represented by at least one of formulae 1-4 to formulae 1-5:
< formulas 1 to 4>
< formulas 1 to 5>
The compound of formula 1 can be prepared by typical methods known to those skilled in the art.
(A-2) Compound of formula 2
The composition for encapsulating an organic light emitting diode according to the present invention may include a compound of formula 2:
< formula 2>
Wherein
R20Is composed of
R21Is hydrogen, substituted or unsubstituted C1To C50A hydrocarbon group,
And is
R22And R23Is substituted or unsubstituted C1To C50Hydrocarbyl or substituted or unsubstituted C containing at least one N or O radical1To C50Hydrocarbyl radical
(R25、R26、R27And R28Each independently hydrogen, halogen, -CN, -NO2or-NH2，
X is-O-or-N-E1-，
E1Is hydrogen, substituted or unsubstituted C1To C50A hydrocarbon radical or containing at least one F, Cl, Br, I, O, N, S, P or Si atomSubstituted or unsubstituted C of a group1To C50A hydrocarbon group,
R24Is substituted or unsubstituted C1To C50Hydrocarbyl or C substituted or unsubstituted by a radical containing at least one O or N atom1To C50A hydrocarbon group,
q is straight-chain or branched C2To C20Alkylene, containing inserted-O-, NH or NR34C is a straight chain or branched chain of at least one of2To C20Alkylene radical, C5To C10Cycloalkylene, p-phenylene, p,
L is C1To C12Alkylene radical, C2To C12Alkylene radical, C5To C7Cycloalkylene, benzylidene or p-xylylene,
represents the attachment site of the aromatic carbon of the compound of formula 2).
In formula 2, R20Is composed of
And represents the attachment site of the aromatic carbon of the compound of formula 2. Specifically, R of formula 220(may be)
R in formula 220In, R25、R26、R27And R28Each independently hydrogen, halogen, -CN, -NO2or-NH2. In particular toIn other words, R in formula 220In, R25、R26、R27And R28Each independently hydrogen, Cl or Br. More specifically, R in formula 220In, R25And R26May be all hydrogen or may be hydrogen and Cl, hydrogen and Br, and R27And R28May each independently be hydrogen, Cl or Br.
In formula 2, R21Is hydrogen, substituted or unsubstituted C1To C50A hydrocarbon group,
R in formula 221The hydrocarbon group may include a linear or branched alkyl group, a linear or branched alkenyl group, a cycloalkyl group, an arylalkyl group, an aryl group, and the like.
Specifically, R in formula 221In (1), substituted or unsubstituted C1To C50The hydrocarbon radical may be C1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl, having one to four C's substituted on the phenyl ring1To C4Phenyl of alkyl or having one to four C's substituted on the phenyl ring1To C4C of alkyl7To C15A phenylalkyl group.
C1To C24Examples of the linear or branched alkyl group may include methyl, ethyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-pentyl, 2-ethylhexyl, tert-octyl, lauryl, tert-dodecyl, tridecyl, n-hexadecyl, n-octadecyl, and eicosyl groups.
C2To C18Examples of the straight-chain or branched alkenyl group include allyl, pentenyl, hexenyl, dodecenyl and oleyl. C2To C18The linear or branched alkenyl group may be a straight-chain or branched alkenyl group havingAlkenyl of 3 to 16, specifically 3 to 12 (e.g., 2 to 6) carbon atoms.
C5To C12Examples of the cycloalkyl group may include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclododecyl. C1To C4Alkyl substituted C5To C8Examples of the cycloalkyl group may include methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, and tert-butylcyclohexyl.
C7To C15Examples of the phenylalkyl group may include a benzyl group, a phenethyl group, an α -methylbenzyl group and an α, α -dimethylbenzyl group.
Having one to four C's substituted on the benzene ring1To C4Examples of the phenyl group of the alkyl group may include tolyl and xylyl.
R in formula 221In, R25、R26、R27And R28Each independently hydrogen, halogen, -CN, -NO2or-NH2. Specifically, R in formula 221In, R25、R26、R27And R28May each independently be hydrogen, Cl or Br. More specifically, R in formula 221In, R25And R26All are hydrogen or hydrogen and Cl or hydrogen and Br, and R27And R28May each independently be hydrogen, Cl or Br.
R in formula 221In which L is C1To C12Alkylene group, C2To C12Alkylene (alkylene group), C5To C7Cycloalkylene, benzylidene group, or p-xylylene group.
In formula 2, R22、R23And R24Is substituted or unsubstituted C1To C50Hydrocarbyl or substituted or unsubstituted C containing at least one N or O radical1To C50A hydrocarbyl group.
R in formula 222、R23And R24In (1), the hydrocarbon group may include a straight chainOr branched alkyl, linear or branched alkenyl, cycloalkyl, arylalkyl, aryl, and the like.
Specifically, R in formula 222、R23And R24In (1), substituted or unsubstituted C1To C50The hydrocarbon radical may be C1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl, having one to four C's substituted on the phenyl1To C4Phenyl of alkyl or having one to three C's substituted on the phenyl ring1To C4C of alkyl7To C15A phenylalkyl group.
Specifically, R in formula 222、R23And R24In (1), a substituted or unsubstituted C containing at least one O, N or S radical1To C50The hydrocarbyl group contains at least one O, N or S radical as a substituent functional group or at least one O, N or S radical inserted into the hydrocarbon backbone.
Specifically, R in formula 222、R23And R24In O, N or the S radical may include-OH, -OCO-R31、-OR34、-NCO、-NH2、-O-、-NH-、-NR34-、-C(O)-O-R34、-C(O)-NHR34、-C(O)-NR34R'34、-SR33、-NHR33、-N(R33)2、-(CH2)m-CO-X1-(Z)p-Y-R35And the like.
Here, R in formula 222、R23And R24In, R31Is hydrogen, straight-chain or branched C1To C18Alkyl radical, C5To C12Cycloalkyl, straight or branched C3To C8Alkenyl, phenyl, naphthyl or C7To C15A phenylalkyl group.
Here, R in formula 222、R23And R24In, R33Is straight-chain or branched C1To C20Alkyl, straight or branched C2To C20Hydroxyalkyl, straight or branched C3To C18Alkenyl radical, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl, naphthyl, via one or two C1To C4Alkyl-substituted alkylphenyl radicals or substituted by one or two C1To C4Alkyl-substituted naphthyl.
R in formula 222、R23And R24In, R34And R'34Is hydrogen or straight or branched C1To C24An alkyl group.
More specifically, R of formula 222、R23And R24Can be via-OH, -OCO-R31、-OR34、-NCO、-NH2And C substituted with at least one functional group of combinations thereof1To C24Linear or branched alkyl.
More specifically, R of formula 222、R23And R24May be a compound having inserted therein-O-, -NH-, -NR-34-C of at least one of and combinations thereof1To C24Linear or branched alkyl.
In one embodiment, the alkyl group having at least one-O-inserted therein may be derived from ethylene oxide units, propylene oxide units, or mixtures thereof.
In one embodiment, there is at least one-NH-or-NR therein34The alkyl group of (A) can be derived from a repeat unit of ethylenediamine.
More specifically, R of formula 222、R23And R24May be a compound having inserted therein-O-, -NH-, -NR-34-C of at least one of and combinations thereof2To C18Straight or branched alkenyl.
More specifically, R of formula 222、R23And R24Can be through-OH, -OR34、-NH2And C substituted with at least one functional group of combinations thereof1To C24Linear or branched alkyl.
More specifically, R of formula 222、R23And R24Can be-OR34、-C(O)-O-R34、-C(O)-NHR34or-C (O) -NR34R'34。
More specifically, R of formula 222、R23And R24Can be-SR33、-NHR33or-N (R)33)2。
More specifically, R of formula 222、R23And R24Can be- (CH)2)m-CO-X1-(Z)p-Y-R35。
R in formula 222、R23And R24In, X1Can be-O-or-N (R)36)-。
R in formula 222、R23And R24In which Y can be-O-, -N (R)37) -or a direct bond.
R in formula 222、R23And R24In which Z is C2To C12An alkylene group; c having one to three N or O atoms or combinations thereof inserted therein4To C12An alkylene group; c3To C12Alkylene, butenylene, butynylene, cyclohexylene or phenylene; each hydroxy-substituted C3To C12Alkylene, butenylene, butynylene, cyclohexylene or phenylene;
(wherein denotes the attachment site).
Specifically, when R in formula 222、R23And R24When Y in the above-mentioned group is a direct bond, Z may be a direct bond.
R in formula 222、R23And R24In (b), m may be 0, 1 or 2.
R in formula 222、R23And R24In the formula, p is 1; or when X is1And Y is each independently-N (R)36) -and-N (R)37) When isAnd p is 0.
R in formula 222、R23And R24In, R35Is hydrogen, C1To C12Alkyl, aryl, heteroaryl, and heteroaryl,
-CO-C(R38)＝C(H)R39Or when Y is-N (R)37) Is-time with R37Together form-CO-CH ═ CH-CO-.
Here, R in formula 222、R23And R24In, R38Is hydrogen or methyl, and R39Is hydrogen, methyl or-CO-X1-R40。
Here, R in formula 222、R23And R24In, R40Is hydrogen, C1To C12Alkyl, aryl, heteroaryl, and heteroaryl,
Here, R in formula 222、R23And R24In, R36And R37Each independently is hydrogen, C1To C12Alkyl, C having one to three oxygen atoms therein1To C12Alkyl, C having one to three oxygen atoms therein3To C12Alkyl, cyclohexyl, C7To C15Phenylalkyl, and when Z is ethylene, R36And R37Together form an ethylene group.
In formula 2, X is-O-or-N- (E)1)-；E1Is hydrogen, substituted or unsubstituted C1To C50A hydrocarbon group, or a substituted or unsubstituted C containing at least one F, Cl, Br, I, O, N, S, P or Si radical1To C50A hydrocarbon group,
In E of formula 21The hydrocarbon group may include linear or branched alkyl, linear or branched alkenyl, alkynyl, cycloalkyl, arylalkyl, aryl, and the like.
Specifically, in E of formula 21In (1), substituted or unsubstituted C1To C50The hydrocarbon radical may be C1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl, C2To C6Alkynyl, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl, naphthyl, having one to four C's substituted on the phenyl ring1To C4Phenyl of alkyl or having one to four C's substituted on the phenyl ring1To C4C of alkyl7To C15A phenylalkyl group.
Specifically, in E of formula 21In (1), a substituted or unsubstituted C containing at least one F, Cl, Br, I, O, N, S, P or Si radical1To C50The hydrocarbyl group contains at least one F, Cl, Br, I, O, N, S, P or Si radical as a substituent functional group; or comprises at least one F, Cl, Br, I, O, N, S, P or Si radical inserted into the hydrocarbon backbone.
Specifically, in E of formula 21Wherein the F, Cl, Br, I, O, N, S, P OR Si radical may comprise-F, -OH, -OR42、-NH2、-NHR42、-N(R42)2、-NHCOR43、-NR42COR43、-OCOR44、-COR45、-SO2R46、-PO(R47)n(R48)2-n、-Si(R49)n(R50)3-n、-Si(R42)3、-N+(R42)3A-、-S+(R42)2A--oxirane, -CN, -CF3、-NO2、-NHR42、-N(R42)2、-SO2R46、-PO(R47)n(R48)2-n、-OR42、-COR45、-R45And the like.
In E of formula 21In, n means 0, 1 or 2; and A is-Meaning that it can be bonded to-N+or-S+General anion of (1).
In E of formula 21In, R42Is straight-chain or branched C1To C18Alkyl, straight or branched C2To C18Alkenyl radical, C5To C10Cycloalkyl, phenyl, naphthyl, C7To C15Phenylalkyl or coupling two R42To form a pyrrolidine, piperidine or morpholine structure together with the N or Si atom.
In E of formula 21In, R43Is hydrogen, -OR42、-NHR42、-N(R42)2or-R42。
In E of formula 21In, R44is-OR42、-NHR42、-N(R42)2or-R42。
In E of formula 21In, R45Is hydrogen, -OH, -OR42、-NHR42、-N(R42)2O-glycidyl or-R42。
In E of formula 21In, R46is-OH, -OR42、-NHR42or-N (R)42)2。
In E of formula 21In, R47is-NH2、-NHR42or-N (R)42)2。
In E of formula 21In, R48is-OH OR-OR42。
In E of formula 21In, R49is-Cl OR-OR42。
In E of formula 21In, R50Is straight-chain or branched C1To C18An alkyl group.
More specifically, E of formula 21Can be hydrogen or C1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl, C2To C6Alkynyl, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl or naphthyl.
More specifically, E of formula 21Can be a compound including-F, -OH, -OR42、-NH2、-NHR42、-N(R42)2、-NHCOR43、-NR42COR43、-OCOR44、-COR45、-SO2R46、-PO(R47)n(R48)2-n、-Si(R49)n(R50)3-n、-Si(R42)3、-N+(R42)3A-、-S+(R42)2A-C with at least one functional group of ethylene oxide and combination thereof as a substituent1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl or C2To C6Alkynyl. Here, n is 0, 1 or 2; and A is-Is coupleable to-N+or-S+The anion of (4).
More specifically, E of formula 21May be a compound containing-O-, -S-, -NH-, -NR-inserted therein42-C of at least one of and combinations thereof1To C24Straight or branched alkyl, C2To C18Straight-chain or branched alkenyl, C2To C6Alkynyl, C5To C12Cycloalkyl radical, C7To C15Phenylalkyl, phenyl or naphthyl.
More specifically, E of formula 21Can be a compound containing-F, -Cl, -Br, -I, -CN, -CF3、-NO2、-NHR42、-N(R42)2、-SO2R46、-PO(R47)n(R48)2-n、-OH、-OR42、-COR45、-R45And C as a substituent of at least one of the group consisting of7To C15Phenylalkyl, phenyl or naphthyl.
In E of formula 21In, R21、R22、R23、R24、R25、R26、R27And R28As defined above.
In the formula 2, Q is a straight chain or branched C2To C20Alkylene, containing inserted therein-O-, -NH-or-N (R)34) -a linear or branched C of at least one of2To C20Alkylene radical, C5To C10Cycloalkylene, p-phenylene, p,
(wherein denotes the attachment site).
The compound of formula 2 may be prepared by typical methods known in the art or may be a commercially available product.
Specifically, the compound of formula 2 may be represented by at least one of formula 2-1 to formula 2-12:
< formula 2-1>
< formula 2-2>
< formulas 2 to 3>
< formulas 2 to 4>
< formulas 2 to 5>
< formulas 2 to 6>
< formulas 2 to 7>
< formulas 2 to 8>
< formulas 2 to 9>
< formulas 2 to 10>
< formulas 2 to 11>
< formulas 2 to 12>
The compound of formula 2 may be prepared by typical methods known in the art or may be a commercially available product.
(A-3) Compound of formula 3
The composition for encapsulating an organic light emitting diode according to the present invention may include a compound of formula 3:
< formula 3>
Wherein R is1Is substituted or unsubstituted C1To C10Alkyl, substituted or unsubstituted C6To C20Aryl or substituted or unsubstituted C7To C20An arylalkyl group;
R2is substituted or unsubstituted C6To C20An aryl group;
R3is substituted or unsubstituted C1To C10Alkylene or substituted or unsubstituted C1To C10An alkyleneoxy group; and is
R4Is hydrogen or substituted or unsubstituted C1To C5An alkyl group.
Specifically, in formula 3, R1C which may be substituted or unsubstituted1To C10Alkyl, preferably substituted or unsubstituted C1To C5An alkyl group. Specifically, in formula 3, R2C which may be substituted or unsubstituted6To C18Aryl, preferably substituted or unsubstituted C6To C12And (4) an aryl group. Specifically, in formula 3, R3C which may be substituted or unsubstituted1To C5An alkylene group.
Specifically, the compound of formula 3 may be represented by at least one of formula 3-1 to formula 3-4:
< formula 3-1>
< formula 3-2>
< formula 3-3>
< formulas 3 to 4>
The compound of formula 3 can be prepared by typical methods known in the art.
(B) At least one of a non-silicone-based photocurable multifunctional monomer and a silicone-based photocurable multifunctional monomer
The non-silicone based photocurable multifunctional monomer does not contain silicon (Si) atoms, and may include C having substitution or non-substitution between (meth) acrylate groups1To C20Alkylene, preferably unsubstituted C1To C15Alkylene di (meth) acrylates. Here, the carbon atom of the alkylene group means the number of carbon atoms only present in the alkylene group, excluding the carbon atoms in the di (meth) acrylate group. For example, di (meth) acrylates may be represented by formula 4:
< formula 4>
Wherein R is7And R8Each independently hydrogen or methyl; and R is9Is substituted or unsubstituted C1To C20An alkylene group.
For example, in formula 4, R9May be unsubstituted C8To C12An alkylene group. More specifically, the di (meth) acrylate may comprise a diAt least one of octylene glycol (meth) acrylate, nonanediol di (meth) acrylate, decanediol di (meth) acrylate, undecanediol di (meth) acrylate, and dodecanediol di (meth) acrylate.
In other embodiments, the non-silicone based photocurable multifunctional monomer may include at least one of tri (meth) acrylate, tetra (meth) acrylate, penta (meth) acrylate, and hexa (meth) acrylate as a silicon (Si) -free monomer in addition to di (meth) acrylate. The tri (meth) acrylate may include C3To C20Tri (meth) acrylates of triols, tetraols, pentaols or hexaols, such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, and the like. The tetra (meth) acrylate may include tetra (meth) acrylates of C4 to C20 tetrols, pentaols or hexaols, such as pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, and the like. The penta (meth) acrylate may include penta (meth) acrylates of C4 to C20 pentaols or hexaols, such as dipentaerythritol penta (meth) acrylate, and the like. The hexa (meth) acrylate may include hexa (meth) acrylates of C4 to C20 hexaols, such as dipentaerythritol hexa (meth) acrylate, and the like.
The non-silicone based photocurable multifunctional monomer may be present in an amount of 10 to 70 parts by weight, preferably 20 to 60 parts by weight, more preferably 30 to 60 parts by weight, for example 10, 20, 30, 40, 50, 60 or 70 parts by weight, based on 100 parts by weight of component a, component B, component C and component D. Within this range, the multifunctional monomer may increase the crosslinking density of the encapsulation composition to improve the strength of a layer formed using the encapsulation composition.
The silicone-based photocurable multifunctional monomer may include a Si-containing silicone-based di (meth) acrylate. The encapsulating composition includes a mixture of a non-silicone based di (meth) acrylate and a silicone based di (meth) acrylate as a di (meth) acrylate to reduce its viscosity and cure shrinkage.
The silicone-based di (meth) acrylate may be represented by formula 5:
< formula 5>
Wherein R is51And R52C, equal to or different from each other and each independently of the others, being a single bond, substituted or unsubstituted1To C20Alkylene, substituted or unsubstituted C1To C30Alkylene ether, -N (R)53)-R54- (. is the attachment site of the element, R53Is substituted or unsubstituted C1To C30Alkyl, and R54Is substituted or unsubstituted C1To C20Alkylene), substituted or unsubstituted C6To C30Arylene, substituted or unsubstituted C7To C30Arylalkylene or-O-R54- (. is the attachment site of the element, and R54Is substituted or unsubstituted C1To C20Alkylene groups);
Z1、Z2、Z3、Z4、Z5and Z6Are identical or different from one another and are each independently hydrogen, substituted or unsubstituted C1To C30Alkyl, substituted or unsubstituted C1To C30Alkyl ether radical, -N (R)55)(R56) (. is the attachment site of the element, and R55And R56Are identical or different from one another and are each independently hydrogen or substituted or unsubstituted C1To C30Alkyl), substituted or unsubstituted C1To C30Alkyl sulfide radical, substituted or unsubstituted C6To C30Aryl or substituted or unsubstituted C7To C30An arylalkyl group, which is a cyclic alkyl group,
Z1、Z2、Z3、Z4、Z5and Z6At least one of which is substituted or unsubstituted C6To C30An aryl group;
Y1and Y2Are the same as or different from each other, and are represented by formula 6:
< formula 6>
(wherein is the attachment site of the element, and Z1Is hydrogen or substituted or unsubstituted C1To C30Alkyl groups); and is
n is an integer from 0 to 30 or on average in the range from 0 to 30.
Here, the term "single bond" means that Si and Y are bonded to each other1Without any direct bond between intermediate elements (Y)1-Si) or between Si and Y2Without any direct bond between intermediate elements (Si-Y)2)。
R51And R52Can be C1To C5Alkylene or a single bond. In particular, Z1、Z2、Z3、Z4、Z5And Z6Can be C1To C5Alkyl radical C6To C10Aryl, wherein Z1、Z2、Z3、Z4、Z5And Z6At least one of which may be C6To C10And (4) an aryl group. More specifically, Z1、Z2、Z3、Z4、Z5And Z6Can be C1To C5Alkyl or C6To C10Aryl, wherein Z1、Z2、Z3、Z4、Z5And Z6One, two, three or six of them can be C6To C10And (4) an aryl group. More specifically, Z1、Z2、Z3、Z4、Z5And Z6Can be methyl, ethyl, propyl, butyl, pentyl, phenyl or naphthyl, wherein Z1、Z2、Z3、Z4、Z5And Z6One, two, three or six of these groups may be phenyl or naphthyl. n may be an integer from 1 to 5.
Specifically, the silicone-based di (meth) acrylate may be represented by any one of formula 5-1 to formula 5-6:
< formula 5-1>
< formula 5-2>
< formula 5-3>
< formulas 5 to 4>
< formulas 5 to 5>
< formulas 5 to 6>
The silicone-based di (meth) acrylate can have a weight average molecular weight of 100g/mol to 2,000g/mol, specifically 200g/mol to 1,000g/mol, e.g., 100g/mol, 200g/mol, 300g/mol, 400g/mol, 500g/mol, 600g/mol, 700g/mol, 800g/mol, 900g/mol, 1,000g/mol, 1100g/mol, 1200g/mol, 1300g/mol, 1400g/mol, 1500g/mol, 1600g/mol, 1700g/mol, 1800g/mol, 1900g/mol, or 2,000 g/mol. Within this range, the encapsulation composition exhibits good deposition characteristics, and an organic layer having a low plasma etching rate can be realized.
The silicone-based di (meth) acrylate can be prepared by a typical method, or can be obtained from a commercially available product. For example, the silicone-based di (meth) acrylate may be prepared by reacting a siloxane compound having at least one silicone bond and containing an aryl group with a compound for extending the carbon number (e.g., allyl alcohol), and then with (meth) acryloyl chloride, but is not limited thereto. Alternatively, the silicone-based di (meth) acrylate may be prepared by reacting a siloxane compound having at least one silicone bond and containing an aryl group with (meth) acryloyl chloride, but is not limited thereto.
The silicone-based photocurable polyfunctional monomer may be present in an amount of 10 to 50 parts by weight, preferably 10 to 40 parts by weight, more preferably 10 to 30 parts by weight, for example 10, 20, 30, 40 or 50 parts by weight, based on 100 parts by weight of component a, component B, component C and component D. Within this range, the encapsulating composition may increase the crosslink density to increase the strength of the layer.
At least one of the non-silicone based photocurable polyfunctional monomer and the silicone based photocurable polyfunctional monomer may be present in an amount of 10 parts by weight to 80 parts by weight, preferably 20 parts by weight to 80 parts by weight, more preferably 50 parts by weight to 80 parts by weight, such as 10 parts by weight, 20 parts by weight, 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, or 80 parts by weight, based on 100 parts by weight of the component a, the component B, the component C, and the component D. Within this content range, the encapsulating composition may increase the crosslinking density to increase the strength of the layer.
(C) Photocurable monofunctional monomers
The photocurable monofunctional monomer is used to increase the photocurability of the encapsulation composition. In addition, the photocurable monofunctional monomer can increase the light transmittance of the organic layer and can reduce the viscosity of the encapsulation composition.
Preferably, the photocurable monofunctional monomer may include a non-silicone based photocurable monofunctional monomer containing no silicon atom.
The non-silicone based photocurable monofunctional monomer may include at least one of (C1) an aromatic mono (meth) acrylate containing an aromatic group and (C2) a non-aromatic mono (meth) acrylate containing no aromatic group. Preferably, the non-silicone based photocurable monofunctional monomer may be (C1) an aromatic mono (meth) acrylate containing an aromatic group. The aromatic mono (meth) acrylates ensure better uv blocking effect and plasma resistance of the encapsulating composition compared to the non-aromatic mono (meth) acrylates.
(C1) The aromatic mono (meth) acrylate may include a substituted or unsubstituted aromatic group-containing mono (meth) acrylate. Here, the term "aromatic group" means a monocyclic aromatic group or a polycyclic aromatic group including a condensed form and the like, or means a form in which monocyclic rings are connected to each other by a sigma bond. As used herein, an aromatic radical is a non-indolyl radical that is free of indolyl groups. For example, the aromatic group may include substituted or unsubstituted C6To C50Aryl, substituted or unsubstituted C7To C50Arylalkyl, substituted or unsubstituted C3To C50Heteroaryl and substituted or unsubstituted C3To C50At least one of heteroarylalkyl. More specifically, the aromatic group may include at least one of: phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthryl, phenanthryl,
A phenyl group, a triphenylene group, a tetracenyl group, a pyrenyl group, a benzopyrenyl group, a pentacenyl group, a coronenyl group, an octenyl group, a borenyl group, a benzyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, an acridinyl group, a quinazolinyl group, a cinnolinyl groupCinnamyl group), phthalazinyl group, thiazolyl group, benzothiazolyl group, isoxazolyl group, benzisoxazolyl group, oxazolyl group, benzoxazolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, purinyl group, thienyl group, benzothienyl group, furyl group, benzofuryl group and isobenzofuryl group.
For example, the aromatic mono (meth) acrylate may be represented by formula 7:
< formula 7>
Wherein R is5Is hydrogen or methyl; s is an integer of 0 to 10; and R is6Is substituted or unsubstituted C6To C50Aryl or substituted or unsubstituted C6To C50An aryloxy group.
For example, R6Can be phenylphenoxyethyl, phenoxyethyl, benzyl, phenyl, phenylphenoxy, phenoxy, phenethyl, phenylpropyl, phenylbutyl, methylphenylethyl, propylphenethyl, methoxyphenylethyl, cyclohexylphenethyl, chlorophenylethyl, bromophenylethyl, methylphenyl, methylethylphenyl, methoxyphenyl, propylphenyl, cyclohexylphenyl, chlorophenyl, bromophenyl, phenylphenyl (phenylphenoxy group), biphenyl, terphenyl, quaterphenyl, anthracenyl, naphthyl, triphenylene, methylphenoxy, ethylphenoxy, methylethylphenoxy (methyphenylphenoxy group), methoxyphenoxy, propylphenoxy, cyclohexylphenoxy, chlorophenoxy, bromophenoxy, biphenyloxy, terphenoxy (terphenyloxy group), quaterphenyloxy (quatenyloxy group), anthracenoxy, naphthyloxy, or triphenylphenyloxy (triphenylphenoxy group).
Specifically, the aromatic mono (meth) acrylate may include at least one of: 2-phenylphenoxyethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenyl (meth) acrylate, phenoxy (meth) acrylate, 2-ethylphenoxy (meth) acrylate, benzyl (meth) acrylate, 2-phenylethyl (meth) acrylate, 3-phenylpropyl (meth) acrylate, 4-phenylbutyl (meth) acrylate, 2- (2-methylphenyl) ethyl (meth) acrylate, 2- (3-methylphenyl) ethyl (meth) acrylate, 2- (4-propylphenyl) ethyl (meth) acrylate, 2- (4- (1-methylethyl) phenyl) ethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2- (3-methylphenyl) acrylate, phenoxyethyl (meth) acrylate, phenoxyethyl (2- (3-phenyl) acrylate, 2- (3-phenylethyl) acrylate, 2- (4-phenylethyl) acrylate, 2- (3-ethyl (meth) acrylate, 2- (4-phenyl) acrylate, 2- (4-phenylethyl) acrylate, 2- (4-phenyl) acrylate, 2-ethyl (2- (4-methyl) acrylate, 2- (4-phenylethyl) acrylate, 2-phenyl) acrylate, 2-phenylethyl) acrylate, 2-ethyl (2-ethyl (meth) acrylate, 2-ethyl (2-methyl) acrylate, 2-ethyl (2-methyl) acrylate, 2-phenyl) acrylate, 2-ethyl (2-methyl) acrylate, 2-ethyl (2-ethyl (, 2- (4-methoxyphenyl) ethyl (meth) acrylate, 2- (4-cyclohexylphenyl) ethyl (meth) acrylate, 2- (2-chlorophenyl) ethyl (meth) acrylate, 2- (3-chlorophenyl) ethyl (meth) acrylate, 2- (4-bromophenyl) ethyl (meth) acrylate, 2- (3-phenylphenyl) ethyl (meth) acrylate, 4- (biphenyl-2-yloxy) butyl (meth) acrylate, 3- (biphenyl-2-yloxy) butyl (meth) acrylate, 2- (biphenyl-2-yloxy) butyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2- (biphenyl-2-yloxy) acrylate, and (biphenyl-2-yloxy) acrylate, and/or (p) acrylate, and/or (2-2, 1- (biphenyl-2-yloxy) butyl (meth) acrylate, 4- (biphenyl-2-yloxy) propyl (meth) acrylate, 3- (biphenyl-2-yloxy) propyl (meth) acrylate, 2- (biphenyl-2-yloxy) propyl (meth) acrylate, 1- (biphenyl-2-yloxy) propyl (meth) acrylate, 4- (biphenyl-2-yloxy) ethyl (meth) acrylate, 3- (biphenyl-2-yloxy) ethyl (meth) acrylate, 2- (biphenyl-2-yloxy) ethyl (meth) acrylate, 1- (biphenyl-2-yloxy) ethyl (meth) acrylate, and mixtures thereof, 2- (4-benzylphenyl) ethyl (meth) acrylate, 1- (4-benzylphenyl) ethyl (meth) acrylate, and structural isomers thereof, but is not limited thereto. That is, it is to be understood that the (meth) acrylates described herein are provided as examples only, and the present invention is not limited thereto. Furthermore, the (meth) acrylates according to the invention include all acrylates corresponding to their structural isomers. For example, although 2-phenylethyl (meth) acrylate is mentioned above by way of example only, (meth) acrylate according to the invention includes all 3-phenylethyl (meth) acrylate and 4-phenyl (meth) acrylate.
Specifically, in formula 7, s may be an integer of 1 to 5, and R6Can be substituted or unsubstituted phenylphenoxy, substituted or unsubstituted phenylthio, substituted or unsubstitutedOr a substituted or unsubstituted terphenylphenoxy (terphenylphenoxy group), wherein the substituents may be deuterium, C1 to C10 alkyl, C1 to C10 alkoxy, C6To C18Aryl radical, C3To C18Heteroaryl or thiol groups.
(C2) The nonaromatic mono (meth) acrylates may be substituted or unsubstituted C1To C20Alkyl mono (meth) acrylates. In particular, the non-aromatic mono (meth) acrylate may be unsubstituted straight chain C1To C20Alkyl mono (meth) acrylates, more particularly containing linear unsubstituted C10To C20Alkyl mono (meth) acrylates. For example, the non-aromatic mono (meth) acrylate may include decyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate, and eicosyl (meth) acrylate, but is not limited thereto.
The photocurable monofunctional monomer, preferably a non-silicone based photocurable monofunctional monomer, may be present in an amount of 10 to 60 parts by weight, specifically 15 to 50 parts by weight, more specifically 15 to 40 parts by weight, for example 10, 20, 30, 40, 50 or 60 parts by weight, based on 100 parts by weight of component a, component B, component C and component D. Within this content range, the encapsulation composition may have low viscosity and increased adhesiveness.
(D) Initiator
The initiator may include any typical photopolymerization initiator capable of performing a photocuring reaction. For example, the photopolymerization initiator may include triazine, acetophenone, benzophenone, thioxanthone, benzoin (benzoin), phosphorus, oxime initiators, or mixtures thereof.
The phosphorus initiator may include diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide, benzyl (diphenyl) phosphine oxide, and mixtures thereof. For example, in the compositions according to the invention, the phosphorus initiators may exhibit better initiation properties at long wavelength uv light. These initiators may be used alone or as a mixture thereof.
The initiator may be present in an amount of 1 to 40 parts by weight, specifically 1 to 10 parts by weight, more specifically 1 to 9 parts by weight, 1 to 8 parts by weight, such as 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 20 parts by weight, 30 parts by weight, or 40 parts by weight, based on 100 parts by weight of component a, component B, component C, and component D. Within this range, the initiator performs sufficient photopolymerization upon exposure to light, and deterioration in light transmittance due to unreacted initiator remaining after photopolymerization can be prevented.
The encapsulating composition according to the invention can be prepared by mixing the components a to D. For example, the encapsulating composition may be formed as a solvent-free composition that is solvent-free. For example, when the encapsulating composition is a solventless composition, the weight percents are based on the total weight of component a through component D.
The organic layer formed by photocuring the encapsulating composition may have a light transmittance of 20% or less than 20%, specifically 15% or less than 15%, more specifically 10% or less than 10% at a wavelength of 420nm, preferably at a wavelength of 410nm, more preferably at a wavelength of 405 nm. Within this range, the organic layer may prevent the life span of the organic light emitting diode panel from being shortened due to exposure to sunlight.
The encapsulating composition according to the present invention is a photocurable composition and can be prepared by using ultraviolet light at 10mW/cm2To 500mW/cm2Irradiated for 1 to 50 seconds to cure.
The potting composition according to the present invention can have a viscosity of about 7cP to 50cP at 25 ℃ ± 2 ℃. Within this range, the encapsulating composition can be easily deposited.
The encapsulating composition may have a plasma etch rate of 10% or less than 10%, e.g., 10% or less than 10%, 9% or less than 9%, 8% or less than 8%, 7% or less than 7%, 6% or less than 6%, 5% or less than 5%, 4% or less than 4%, or 3% or less than 3%, as represented by equation 2. Within this range, the encapsulation composition may prevent the organic layer from being removed by plasma etching when the inorganic layer is formed on the organic layer, thereby improving the reliability of the organic light emitting diode.
The encapsulation composition can be used to encapsulate an organic light emitting diode. Specifically, the encapsulation composition may form an organic layer in an encapsulation structure in which an inorganic layer and an organic layer are sequentially stacked on top of each other. In particular, the encapsulation composition may be used in flexible organic light emitting diode displays.
The encapsulating composition may be used for encapsulating components for devices, in particular components for displays, which may suffer from reduced quality or deterioration due to permeation of gases or liquids in the surrounding environment (e.g. oxygen and/or moisture and/or water vapor in the atmosphere) and due to permeation of chemicals used in the preparation of electronic products. Examples of components of the apparatus may include, but are not limited to, lighting devices, metal sensor pads, microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits, charge-coupled devices, light-emitting polymers, light-emitting diodes, and the like.
The organic light emitting diode display according to the present invention may include an organic layer formed using the composition for encapsulating an organic light emitting diode according to an embodiment of the present invention. Specifically, the organic light emitting diode display may include: an organic light emitting diode; and a blocking member stack formed on the organic light emitting diode and including an inorganic layer and an organic layer, which may be formed of the encapsulation composition according to an embodiment of the present invention. Accordingly, the organic light emitting diode display may exhibit high reliability.
Next, an organic light emitting diode display according to an embodiment will be explained with reference to fig. 1. Fig. 1 is a cross-sectional view of an organic light emitting diode display according to one embodiment of the present invention.
Referring to fig. 1, the organic light emitting diode display 100 according to this embodiment includes: a substrate 10; an organic light emitting diode 20 formed on the substrate 10; and a barrier stack 30 formed on the organic light emitting diode 20 and including an inorganic layer 31 and an organic layer 32, wherein the inorganic layer 31 is adjacent to the organic light emitting diode 20, and the organic layer 32 may be formed using the composition for encapsulating the organic light emitting diode according to an embodiment of the present invention.
The substrate 10 may be any substrate as long as the organic light emitting diode can be formed on the substrate. For example, the substrate 10 may be formed of materials such as transparent glass, a plastic plate, and a silicon or metal substrate.
The organic light emitting diode 20 is generally used in an organic light emitting diode display, and although not shown in fig. 1, may include a first electrode, a second electrode, and an organic light emitting layer formed between the first electrode and the second electrode. In addition, the organic light emitting layer may have a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer are sequentially stacked, but is not limited thereto.
The barrier stack 30 includes an inorganic layer 31 and an organic layer 32 composed of different compositions, thereby achieving a function of encapsulating the organic light emitting diode.
The inorganic layer 31 contains a different component from the organic layer 32, thereby complementing the effect of the organic layer. For example, the inorganic layer 31 may include a metal; a non-metal; a compound or alloy of at least two metals; a compound or alloy of at least two non-metals; oxides of metals or non-metals; metal or non-metal fluorides; metal or non-metal nitrides; carbides of metals or non-metals; metallic or non-metallic nitrogen oxides; a metal or non-metal boride; metal or non-metal oxyboride; metal or non-metal silicides; or mixtures thereof. The metal or nonmetal may include silicon (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), bismuth (Bi), transition metals, and lanthanide metals, but is not limited thereto. In particular, the inorganic layer may include silicon oxide (SiO)x) Silicon nitride (SiN)x) Silicon oxynitride (SiO)xNy) Zinc selenide (ZnSe), zinc oxide (ZnO), antimony trioxide (Sb)2O3) Comprising aluminum oxide (Al)2O3) Aluminum oxide (AlO)x) Indium oxide (In)2O3) Or tin oxide (SnO)2)。
The inorganic layer 31 may be deposited by a plasma process or a vacuum process, such as sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition, and combinations thereof.
The organic and inorganic layers may be alternately deposited to ensure the planarization property of the inorganic layers while preventing defects of one inorganic layer from diffusing into the other inorganic layer.
The organic layer 32 may be formed by a combination of coating, depositing, and curing an encapsulation composition according to an embodiment of the present invention. For example, the organic layer 32 may be formed by coating the encapsulation composition to a thickness of 1 μm to 50 μm, and then by applying 10mW/cm2To 500mW/cm2Irradiating for 1 to 50 seconds to cure the composition.
The blocker stack 30 may include any number of organic and inorganic layers. The combination of organic and inorganic layers may vary with the level of permeation resistance to oxygen and/or moisture and/or water vapor and/or chemicals. For example, the organic layer and the inorganic layer may be formed to a total of 10 layers or less than 10 layers, such as 2 to 7 layers. Specifically, the organic layer and the inorganic layer were formed in the following order to be 7 layers in total: inorganic layer/organic layer/inorganic layer.
In the barrier stack 30, organic layers and inorganic layers may be alternately deposited. This is because the above composition has an influence on the organic layer due to its properties. Thus, the organic and inorganic layers may supplement or enhance the encapsulation of the components of the device.
Next, an organic light emitting diode display according to another embodiment will be explained with reference to fig. 2. Fig. 2 is a cross-sectional view of an organic light emitting diode display according to another embodiment of the present invention.
Referring to fig. 2, the organic light emitting diode display 200 according to this embodiment includes: a substrate 10; an organic light emitting diode 20 formed on the substrate 10; and a barrier stack 30 formed on the organic light emitting diode 20 and including an inorganic layer 31 and an organic layer 32, wherein the inorganic layer 31 encapsulates an inner space 40 in which the organic light emitting diode 20 is received, and the organic layer 32 may be formed of a composition for encapsulating an organic light emitting diode according to an embodiment of the present invention. The organic light emitting diode display 200 according to this embodiment is substantially the same as the organic light emitting diode display 100 according to the above-described embodiment, except that the inorganic layer 31 does not adjoin the organic light emitting diode 20.
Next, the present invention will be explained in more detail with reference to examples. It should be noted, however, that these examples are provided for illustration only and should not be construed as limiting the invention in any way.
Preparation example 1: preparation of Compounds of formulae 1-4
In a1,000 ml flask equipped with a cooling tube and a stirrer, 300ml of acetone, 39g of triethylamine and 50g of 2,2'- [9, 10-anthracenediylbis (oxy) ] bisethanol (2,2' - [9, 10-anthracenylbix (oxy)) bisethane (esto Ltd.) were placed in this order, and then 30.2g of methacryloyl chloride was slowly added thereto while stirring the components at 0 ℃. Subsequently, the mixture was stirred for 1 hour after the temperature of the flask was increased to 40 ℃. The remaining solvent was removed by distillation, thereby obtaining a compound of formulae 1 to 4 having a High Performance Liquid Chromatography (HPLC) purity of 96%.
Preparation example 2: preparation of the Compound of formula 3-1
In a1,000 ml flask equipped with a cooling tube and a stirrer, 200g of cyanoacetic acid, 320g of 2-hydroxyethyl methacrylate, 600ml of toluene and 3g of concentrated sulfuric acid (Daejung Chemicals, Inc., Daejung, Inc.)&Materials co., Ltd.)) then nitrogen purged for 30 minutes and the flask heated to 160 ℃ to remove water therefrom. The solvent was removed by distillation, whereby 2-propenoic acid-2-methyl-2- [ (cyanocarbonyl) oxy ] having an HPLC purity of 96% was obtained]Ethyl ester (2-cyanoacetoxyethyl methacrylate, weight average molecular weight: 197.19 g/mol). (hydrogen Nuclear Magnetic Resonance (NMR))1H nuclear magnetic resonance，1H NMR)：δ6.12,s,1H；δ5.62,s,1H；δ4.45,m,2H；δ4.38,m,2H；δ3.01,s,2H；δ1.94,s,3H)
In 500 provided with a cooling pipe and a stirrerIn a ml flask, 15.2g of KOH, 38g of methyl iodide, 50g of 2-phenyl-1H-indole-3-carbaldehyde and 150g of Dimethylformamide (DMF) were placed and stirred at room temperature for 12 hours. The solvent was removed by distillation, whereby 1-methyl-2-phenyl-1H-indole-3-carbaldehyde having an HPLC purity of 96% (weight-average molecular weight: 235.28g/mol) was obtained. (1H NMR：δ9.76,s,1H；δ8.46,m,1H；δ7.59,m,3H；δ7.52,m,2H；δ7.42,m,3H；δ3.79,s,3H)
In a 500ml flask equipped with a cooling tube and a stirrer, 21g of 1-methyl-2-phenyl-1H-indole-3-carbaldehyde and 21.2g of 2-acrylic acid-2-methyl-2- [ (cyanocarbonyl) oxy group were placed]Ethyl ester (2-cyanoacetoxyethyl methacrylate), 2.3g piperidine and 230g pyridine were stirred at room temperature for 12 hours. The solvent was removed by distillation, followed by recrystallization from ethanol, whereby a compound represented by formula 3-1 and having an HPLC purity of 98% (molecular weight: 414.45g/mol) was obtained. (1H NMR：δ8.46,m,1H；δ8.17,s,1H；δ7.59,m,3H；δ7.42,m,5H；δ6.15,s,1H；δ5.62,s,1H；δ4.51,m,2H；δ4.42,m,2H；δ3.75,s,3H；δ1.96,s,3H)
Preparation example 3: preparation of the Compound of formula 5-2
In a1,000 ml flask equipped with a cooling tube and a stirrer, 300ml of ethyl acetate, 21g of 3, 3-diphenyl-1, 1,5, 5-tetramethyltrisiloxane and 43g of allyl alcohol (Darong chemical Co., Ltd.) were placed in this order, followed by nitrogen purging for 30 minutes. Next, 72ppm of Pt-loaded carbon black powder (Aldrich GmbH) was added to the flask, which was then heated to 80 ℃ and the components stirred for 4 hours. The remaining solvent was removed by distillation, whereby a compound was obtained. 71.5g of the obtained compound and 39g of triethylamine were sequentially added to 300ml of dichloromethane, and then 30.2g of methacryloyl chloride was slowly added thereto while the mixture was stirred at 0 ℃. The remaining solvent was removed by distillation, thereby obtaining a compound represented by formula 5-2 and having an HPLC purity of 96%. (1H NMR：δ7.52,m,6H；δ7.42,m,4H；δ6.25,d,2H；δ6.02,dd,2H；δ5.82,t,1H；δ5.59,d,2H；δ3.86,m,4H；δ1.52,m,4H；δ0.58,m,4H；δ0.04,m,12H)
Details of components used in examples and comparative examples are as follows.
(A1) Preparation example 1 Compound (Compounds of formulae 1-4)
(A2) The compound of formula 2 (Tinuvin)970, 6-butyl-2- [2-hydroxy-3- (1-methyl-1-phenylethyl) -5- (1,1,3,3-tetramethylbutyl) phenyl ] pyrrole [3,4-f ] benzotriazole-5,7(2H,6H) -dione (6-butyl-2- [2-hydroxy-3- (1-methyl-1-phenylethyl) -5-
(1,1,3,3-tetramethylbutyl) phenyl ] pyrolo [3,4-f ] benzotriazole-5,7(2H,6H) -dion), BASF)
(A3) Preparation 2 Compound (Compound of formula 3-1)
(A4) Tinnefen 477(2,4, 6-tris [4- (1-octyloxycarbonyl) ethoxy-2-hydroxyphenyl ] -1,3, 5-triazine, basf corporation)
(B1)1, 12-Dodecanediol diacrylate (Sartomer Co., Ltd.; Ltd.)
(B2)1, 9-nonanediol diacrylate (Sartomer Co., Ltd.)
(B3) Preparation 3 Compound (Compound of formula 5-2)
(C1) Aromatic mono (meth) acrylate (M1142, Miwon Co., Ltd.)
(C2) Lauryl acrylate (Shadoma Co., Ltd.)
(D) Initiator: darocco (Darocur) TPO (Pasteur) (phosphorus initiator)
Example 1
3 parts by weight of (A1) the compound of production example 1, 47 parts by weight of (B1)1, 12-dodecanediol diacrylate, 28 parts by weight of (B3) the compound of production example 3, 19 parts by weight of (C1) aromatic mono (meth) acrylate and 3 parts by weight of (D) an initiator were put in a 125ml brown polypropylene bottle and mixed at room temperature for 3 hours by an agitator, thereby obtaining an encapsulating composition.
Examples 2 to 6 and comparative examples 1 to 4
An encapsulating composition (unit: parts by weight) was prepared in the same manner as in example 1, except that the contents of the components of example 1 were changed as listed in table 1.
Each of the encapsulating compositions prepared in examples and comparative examples was evaluated with respect to the following properties listed in table 1. The results are shown in table 1.
(1) Viscosity (unit: cP): the viscosity of each of the potting compositions prepared in examples and comparative examples was measured at 25 ℃ using a Spindle (Spindle No.40) of viscometer No.40 (LV DV-II Pro, Brookfield co., Ltd.).
(2) Photocuring rate (unit:%): at 1,635cm-1(C ═ C) and 1,720cm-1With respect to the intensity of the absorption peak in the vicinity of (C ═ O), each encapsulating composition was measured using a Fourier transform infrared (FT-IR) spectrometer (NICOLET)4700, Thermo co., Ltd.). Each encapsulating composition was applied to a glass substrate by a sprayer and then passed at 100mW/cm2Ultraviolet irradiation was carried out for 10 seconds to carry out curing, thereby preparing a sample having a size of 20cm × 20cm × 3 μm (width × length × thickness). Then, at 1,635cm-1(C ═ C) and 1,720cm-1The intensity of the absorption peak of the cured film was measured near (C ═ O) using an FT-IR spectrometer (niketer 4700, thermo electric limited). The photocuring rate was calculated by equation 1:
photocuring rate (%) ═ 1- (a/B) | × 100 (equation 1)
Wherein A is at 1,635cm as measured for the cured film-1Intensity of nearby absorption peak is at 1,720cm-1The ratio of the intensities of the nearby absorption peaks, and B is at 1,635cm measured for the encapsulating composition-1Intensity of nearby absorption peak is at 1,720cm-1The ratio of the intensities of nearby absorption peaks.
(3) Plasma etching rate (unit:%): each encapsulation composition was deposited to a predetermined thickness on a Si wafer and photocured to form an organic layer, and then the initial deposition height (T1, unit: μm) of the organic layer was measured. The organic layer was subjected to Inductively Coupled Plasma (ICP) processing under the following conditions: inductively coupled plasma power: 2,500W, RE power: 300W, direct current bias (DC bias): 200V, Ar flow rate: 50sccm, etch time: 1 minute and pressure: 10 mTorr, and then the height of the organic layer (T2, unit: μm) was measured. The height (thickness) of the organic layer was measured using a field emission scanning electron microscope (FE-SEM) (Hitachi High Technologies Corporation). The plasma etch rate of the organic layer was calculated by equation 2:
the plasma etching rate (%) of the organic layer was (T1-T2)/T1 × 100 (equation 2).
(4) Light transmittance (unit:%): in N2Each encapsulating composition was cured by ultraviolet irradiation under the conditions to form a film 10 μm thick, and then measured with respect to light transmittance at a wavelength of 405nm using a blue-landa (Lambda)950 (Perkin Elmer co., Ltd.)).
TABLE 1
As shown in table 1, the encapsulation composition according to the present invention can realize an organic layer having a good ultraviolet blocking effect and a low plasma etching rate.
In contrast, the compositions of comparative examples 1 and 4, in which the content of component a is not within the range of the present invention, had high plasma etching rates and insignificant ultraviolet blocking effects. In addition, the compositions of comparative examples 2 and 3, which include other compounds instead of component a, have high plasma etching rates and insignificant ultraviolet blocking effects.
It is to be understood that various modifications, alterations, adaptations, and equivalent embodiments may be made by those skilled in the art without departing from the spirit and scope of the present invention.
Claims (3)
1. A composition for encapsulating an organic light emitting diode comprising:
and (2) component A: a compound of formula 1;
and (B) component: at least one of a non-silicone-based photocurable multifunctional monomer and a silicone-based photocurable multifunctional monomer;
and (3) component C: a photocurable monofunctional monomer; and
and (3) component D: an initiator, wherein the initiator is selected from the group consisting of,
wherein the compound of formula 1 is present in an amount of 0.01 to 10 parts by weight, based on 100 parts by weight of the total of the component A, the component B, the component C, and the component D:
< formula 1>
Wherein R is1、R2、R3、R4、R6、R7、R8And R9Is a hydrogen atom, and is,
R5and R10Each is a group of formula 1-2:
< formulas 1 and 2>
Wherein denotes the attachment site of an aromatic carbon of said compound of formula 1,
R11is substituted or unsubstituted C1To C5An alkyl group, a carboxyl group,
R13is substituted or unsubstituted C1To C10An alkylene group or a substituted alkylene group,
X1is O
n is 1;
the non-silicone light-curable multifunctional monomer is 1, 12-dodecanediol diacrylate;
the silicone-based photocurable multifunctional monomer is a compound represented by formula 5-2:
< formula 5-2>
The photocurable monofunctional monomer is a non-silicone-based photocurable monofunctional monomer that is an aromatic mono (meth) acrylate having an aromatic group, and
based on 100 parts by weight of the total of the component A, the component B, the component C and the component D, the composition comprises: 10 to 80 parts by weight of the component B, 10 to 60 parts by weight of the component C, and 1 to 40 parts by weight of the component D.
2. The composition for encapsulating an organic light emitting diode according to claim 1, wherein the compound of formula 1 is a compound of formulae 1-4:
< formulas 1 to 4>
3. An organic light emitting diode display comprising an organic layer formed using the composition for encapsulating an organic light emitting diode according to claim 1 or claim 2.
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| WO2023167480A1 (en) | 2022-03-03 | 2023-09-07 | 주식회사 엘지에너지솔루션 | Air lifting device and drying device for manufacturing electrode comprising same |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014042328A1 (en) * | 2012-09-13 | 2014-03-20 | 제일모직 주식회사 | Photocurable composition, barrier layer comprising same, and encapsulated apparatus comprising same |
| KR20140076426A (en) * | 2012-12-12 | 2014-06-20 | 제일모직주식회사 | Photocurable composition, barrier layer comprising the same and encapsulated apparatus comprising the same |
| CN105164209A (en) * | 2013-04-30 | 2015-12-16 | 三星Sdi株式会社 | Photo-curing composition and encapsulated device comprising same |
| CN106232685A (en) * | 2014-04-23 | 2016-12-14 | 三星Sdi株式会社 | Organic luminescent assembly encapsulates constituent and uses its organic luminescent assembly display device prepared |
| CN107216656A (en) * | 2016-03-22 | 2017-09-29 | 信越化学工业株式会社 | Ultra-violet solidified silicon-ketone composition and its solidfied material and the optical element encapsulating material containing said composition |
| JP2018030989A (en) * | 2015-12-08 | 2018-03-01 | セメダイン株式会社 | Photocurable composition, cured composition-containing product, sticking method, and method for producing product |
| CN108137755A (en) * | 2015-10-19 | 2018-06-08 | 三星Sdi株式会社 | Composition and the organic illuminating element display device that is produced from it for encapsulating organic light emitting element |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602006020839D1 (en) * | 2005-02-02 | 2011-05-05 | Basf Se | LONG-SWEATED BENZOTRIAZOL UV ABSORBERS AND THEIR USE |
| DE102005012056A1 (en) * | 2005-03-16 | 2006-09-28 | Basf Coatings Ag | Multicoat paint systems, process for their preparation and their use in the automotive industry |
| JP5007942B2 (en) * | 2007-08-06 | 2012-08-22 | 川崎化成工業株式会社 | Polymerizable composition and polymer thereof |
| TWI569490B (en) | 2011-11-28 | 2017-02-01 | 半導體能源研究所股份有限公司 | Sealed body, light-emitting module, and method of manufacturing sealed body |
| JP5435520B1 (en) | 2013-03-29 | 2014-03-05 | 古河電気工業株式会社 | Resin composition for sealing element for organic electronic device, resin sheet for sealing element for organic electronic device, organic electroluminescence element, and image display device |
| EP2981579B1 (en) | 2013-04-02 | 2018-10-17 | Basf Se | Coated carbon fiber reinforced plastic parts |
| TWI648892B (en) | 2013-12-26 | 2019-01-21 | 日商琳得科股份有限公司 | Sheet-like sealing material, sealing sheet, electronic device sealing body, and organic EL element |
| EP3565861B1 (en) * | 2016-11-30 | 2023-06-21 | Basf Se | Photocurable hardcoat compositions, methods, and articles derived therefrom |
| KR20180076689A (en) | 2016-12-28 | 2018-07-06 | 엘지디스플레이 주식회사 | Display device |
| KR102126045B1 (en) * | 2017-07-21 | 2020-06-23 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same |
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Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014042328A1 (en) * | 2012-09-13 | 2014-03-20 | 제일모직 주식회사 | Photocurable composition, barrier layer comprising same, and encapsulated apparatus comprising same |
| KR20140076426A (en) * | 2012-12-12 | 2014-06-20 | 제일모직주식회사 | Photocurable composition, barrier layer comprising the same and encapsulated apparatus comprising the same |
| CN105164209A (en) * | 2013-04-30 | 2015-12-16 | 三星Sdi株式会社 | Photo-curing composition and encapsulated device comprising same |
| CN106232685A (en) * | 2014-04-23 | 2016-12-14 | 三星Sdi株式会社 | Organic luminescent assembly encapsulates constituent and uses its organic luminescent assembly display device prepared |
| CN108137755A (en) * | 2015-10-19 | 2018-06-08 | 三星Sdi株式会社 | Composition and the organic illuminating element display device that is produced from it for encapsulating organic light emitting element |
| JP2018030989A (en) * | 2015-12-08 | 2018-03-01 | セメダイン株式会社 | Photocurable composition, cured composition-containing product, sticking method, and method for producing product |
| CN107216656A (en) * | 2016-03-22 | 2017-09-29 | 信越化学工业株式会社 | Ultra-violet solidified silicon-ketone composition and its solidfied material and the optical element encapsulating material containing said composition |
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| TW202009270A (en) | 2020-03-01 |
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