CN115678326A - Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom - Google Patents
Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom Download PDFInfo
- Publication number
- CN115678326A CN115678326A CN202211458816.XA CN202211458816A CN115678326A CN 115678326 A CN115678326 A CN 115678326A CN 202211458816 A CN202211458816 A CN 202211458816A CN 115678326 A CN115678326 A CN 115678326A
- Authority
- CN
- China
- Prior art keywords
- composition
- light emitting
- group
- emitting diode
- organic light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 239000012044 organic layer Substances 0.000 title claims description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 33
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 32
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 20
- 125000002091 cationic group Chemical group 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 13
- 238000009616 inductively coupled plasma Methods 0.000 claims description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 11
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 10
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000004907 flux Effects 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- LWHOMMCIJIJIGV-UHFFFAOYSA-N (1,3-dioxobenzo[de]isoquinolin-2-yl) trifluoromethanesulfonate Chemical compound C1=CC(C(N(OS(=O)(=O)C(F)(F)F)C2=O)=O)=C3C2=CC=CC3=C1 LWHOMMCIJIJIGV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 6
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 5
- WVXLLHWEQSZBLW-UHFFFAOYSA-N 2-(4-acetyl-2-methoxyphenoxy)acetic acid Chemical compound COC1=CC(C(C)=O)=CC=C1OCC(O)=O WVXLLHWEQSZBLW-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- HUGHWHMUUQNACD-UHFFFAOYSA-N prop-2-enoxymethylbenzene Chemical compound C=CCOCC1=CC=CC=C1 HUGHWHMUUQNACD-UHFFFAOYSA-N 0.000 claims description 5
- 238000005229 chemical vapour deposition Methods 0.000 claims description 4
- 238000005530 etching Methods 0.000 claims description 4
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 3
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 claims description 3
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 claims description 3
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 3
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- 229910052786 argon Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 47
- 238000001723 curing Methods 0.000 description 29
- 239000003999 initiator Substances 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- -1 (pentafluoronaphthalene) borate Chemical compound 0.000 description 17
- 230000004888 barrier function Effects 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 229910052755 nonmetal Inorganic materials 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 150000002843 nonmetals Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 4
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 3
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 238000009832 plasma treatment Methods 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
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 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
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-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
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000011417 postcuring Methods 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 2
- XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- WBELHNUIWMNAFH-UHFFFAOYSA-N 12-prop-2-enoyloxydodecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCCCOC(=O)C=C WBELHNUIWMNAFH-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QKQFIIOUCQZCFT-UHFFFAOYSA-O benzyl-(4-hydroxyphenyl)-methylsulfanium Chemical compound C=1C=C(O)C=CC=1[S+](C)CC1=CC=CC=C1 QKQFIIOUCQZCFT-UHFFFAOYSA-O 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
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-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
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012954 diazonium Substances 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
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MOWNZPNSYMGTMD-UHFFFAOYSA-N oxidoboron Chemical class O=[B] MOWNZPNSYMGTMD-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 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
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
Abstract
The present invention relates to a composition for encapsulating an organic light emitting diode and an organic light emitting diode display including the same. The composition comprises: a vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound and a photoacid generator, wherein the vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound is present in an amount of about 95 parts by weight to 99.9 parts by weight based on a solid content relative to about 100 parts by weight of the composition.
Description
The present invention is a divisional application of an invention patent application having an application number of 202110615130.6, entitled composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom, filed on 2021, 06, 02.
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 therefrom. More particularly, the present invention relates to a composition for encapsulating an organic light emitting diode, which has a high light-curing rate, a low post-curing plasma etching rate, and a low post-curing dielectric constant (permittivity, epsilon), and an organic light emitting diode display including an organic layer formed therefrom.
Background
The organic light emitting diode may suffer from reliability deterioration when in contact with external moisture or oxygen. Therefore, the organic light emitting diode needs to be encapsulated with an encapsulation layer (stack of organic and inorganic layers) including organic and inorganic layers formed from a composition for encapsulating the organic light emitting diode.
The organic layer may be formed by applying a composition for encapsulating the organic light emitting diode to a predetermined thickness, followed by curing. Recently, inkjet coating is considered as a method of applying the composition. Inkjet coating allows for the dropwise deposition of the composition onto a surface through a nozzle at a predetermined temperature and a predetermined drop rate. In order to be suitable for inkjet coating, the viscosity of the composition needs to be reduced. However, the reduction in viscosity does not necessarily ensure good ink-jet coatability.
In the organic light emitting diode display, various display elements are stacked on upper and lower sides of the organic light emitting diode, except for an encapsulation layer. The organic light emitting diode is affected by electricity, static electricity, or electromagnetic waves emitted from the display element. This results in malfunction or degradation of the organic light emitting diode. Therefore, there is a need for a composition for encapsulating an organic light emitting diode, which is capable of forming an organic layer having a low dielectric constant and thus can minimize the effect of other elements stacked on the organic light emitting diode, while having a basic function of encapsulating the organic light emitting diode.
The background art of the present invention is disclosed in korean patent laid-open publication No. 10-2016-0150255.
Disclosure of Invention
It is an object of the present invention to provide a composition for encapsulating an organic light emitting diode, which can form an organic layer having good plasma resistance after curing.
Another 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 low dielectric constant over a wide frequency range after curing.
It is still another object of the present invention to provide a composition for encapsulating an organic light emitting diode, which has a high light curing rate and thus can form an organic layer having high light transmittance after curing.
It is still another object of the present invention to provide a composition for encapsulating an organic light emitting diode, which has good inkjet coatability.
One aspect of the present invention relates to a composition for encapsulating an organic light emitting diode.
1. The composition for encapsulating an organic light emitting diode includes: a cationic polymerizable compound containing a vinyl, allyl, or vinyl ether group; and a photoacid generator, wherein the cationic polymerizable compound containing a vinyl group, an allyl group, or a vinyl ether group is present in an amount of about 95 parts by weight to 99.9 parts by weight, based on a solid content, relative to about 100 parts by weight of the composition.
2. In embodiment 1, the vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound may comprise at least one selected from the group consisting of: a compound having an alicyclic group or an aromatic group and having at least one vinyl group, allyl group or vinyl ether group in its molecular structure, and a compound having no alicyclic group or aromatic group and having at least one vinyl group, allyl group or vinyl ether group in its molecular structure.
3. In embodiments 1 and 2, the vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound may include at least one selected from the group consisting of: divinylbenzene, 1,4-cyclohexanedimethanol divinyl ether, allyl benzyl ether, and 5-vinylbicyclo [2.2.1] hept-2-ene, diethylene glycol divinyl ether, 1-tetradecene, triethylene glycol divinyl ether, octadecyl vinyl ether, trimethylolpropane diallyl ether, and 1,4-butanediol divinyl ether.
4. In embodiments 1 to 3, the photoacid generator may include at least one selected from among: n-hydroxynaphthalimide trifluoromethanesulfonate (N-hydroxynaphthalimide triflate) and thiop-phenylene bis (4,4 '-dimethyldiphenylsulfonium) bis-tetrakis (pentafluorophenyl) borate (thio-p-phenylenebis (4,4' -dimethyldiphenylsulfonium) bis-tetrakis (pentafluoronaphthalene) borate).
5. In examples 1-4, the composition may further comprise: (meth) acrylic photocurable monomers; and a photo radical initiator.
6. In examples 1-5, the composition may have a post-cure dielectric constant of about 2.9 or less than 2.9.
7. In embodiments 1-6, the composition may have a post-cure plasma etch rate of about 10% or less than 10%, as calculated according to equation 1:
post-cure plasma etch rate (%) = { (T1-T2)/T1 }. Times.100' - - (1)
Wherein T1 indicates an initial thickness (unit: micrometer) of an organic layer obtained by depositing a composition on a silicon (Si) wafer followed by curing by light irradiation at a flux of 100 mW/cm for 10 seconds, and T2 indicates an initial thickness (unit: micrometer) of an organic layer obtained by depositing a composition on a silicon (Si) wafer, and curing by light irradiation at a flux of 100 mW/cm for 10 seconds, and in an Inductively Coupled Plasma (ICP) power: 2,500 watts, RE power: 300 Watts, DC bias: 200V, ar flow: 70 standard cubic centimeters per minute, etching time: 1 minute and pressure: the thickness (unit: μm) of the organic layer after the ICP plasma treatment by inductively coupled plasma chemical vapor deposition (ICP CVD) under the condition of 10 mtorr.
Another aspect of the present invention relates to an organic light emitting diode display comprising an organic layer formed from 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 good plasma resistance after curing.
The present invention provides a composition for encapsulating an organic light emitting diode, which can form an organic layer having a low dielectric constant over a wide frequency range after curing.
The present invention provides a composition for encapsulating an organic light emitting diode, which has a high light curing rate and thus can form an organic layer having high light transmittance after curing.
The invention provides a composition for encapsulating an organic light emitting diode, which has good ink-jet coatability.
Drawings
Fig. 1 is a cross-sectional view of an organic light emitting diode display according to an 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 the reference numerals
10: a substrate;
20: an organic light emitting diode;
30: barrier stacking;
31: an inorganic layer;
32: an organic layer/organic barrier layer;
40: an inner space;
100. 200: an organic light emitting display.
Detailed Description
Embodiments of the present invention will be described in detail with reference to the accompanying drawings so as to be easily implemented by 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 embodiments. In the drawings, portions irrelevant to the description will be omitted for clarity. Throughout this specification, like components will be denoted by like reference numerals. It should be noted that the drawings are not drawn to precise scale and that lengths or sizes of components may be exaggerated for descriptive convenience and clarity only.
As used herein, the term "(meth) propenyl" may refer to "propenyl" and/or "methylpropenyl".
As used herein, unless otherwise specified, the term "substituted" means that at least one hydrogen atom of a functional group according to the present invention is substituted by: halogen (e.g., F, cl, br or I), hydroxy, nitro, cyano, imino (= NH, = NR, R is C) 1 To C 10 Alkyl), amino (-NH) 2 -NH (R '), -N (R ") (R'"), wherein R ', R "and R'" are each independently C 1 To C 10 Alkyl), amidino, hydrazine or hydrazone groups, carboxyl groups, C 1 To C 20 Alkyl radical, C 6 To C 30 Aryl radical, C 3 To C 30 Cycloalkyl radical, C 3 To C 30 Heteroaryl or C 2 To C 30 A heterocycloalkyl group.
As used herein to represent a particular numerical range, the expression "X to Y" means "greater than or equal to X and less than or equal to Y (X ≦ and ≦ Y)".
The present invention provides a composition for encapsulating an organic light emitting diode (hereinafter, referred to as "composition") which has a high light curing rate and good ink-jettable coatability, and can form an organic layer having good plasma resistance and a low dielectric constant over a wide frequency range after curing.
In one embodiment, the composition according to the present invention can form an organic layer having a plasma etch rate of about 10% or less than 10%, specifically about 0% to 8%, as calculated according to equation 1. Within this range, damage to the organic layer when the inorganic layer is formed on the organic layer can be prevented, thereby extending the lifespan of the organic light emitting diode:
post-cure plasma etch rate (%) = { (T1-T2)/T1 }. Times.100' - - (1)
Where T1 indicates the initial thickness (unit: micrometer) of an organic layer obtained by depositing a composition over a silicon (Si) wafer followed by curing by light irradiation at a flux of 100 milliwatts per square centimeter for 10 seconds, and T2 indicates the initial thickness of the organic layer obtained at an Inductively Coupled Plasma (ICP) power: 2,500 watts, RE power: 300 Watts, DC bias: 200V, ar flow: 70 standard cubic centimeters per minute, etching time: 1 minute and pressure: thickness (unit: micrometer) of the organic layer after the ICP plasma treatment by ICP CVD under a condition of 10 mtorr.
Here, FE-SEM (Hitachi High Technologies Corporation) may be used to measure the thickness (or height) of the organic layer, but is not limited thereto.
In one embodiment, the composition according to the present invention can have a post cure dielectric constant of about 2.9 or less than 2.9 (e.g., 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, or 2.9), specifically about 1.5 to about 2.9 or about 2.0 to about 2.7). Within this range, the organic light emitting diode encapsulated using the composition may exhibit good performance without being affected by external static electricity or electricity. In particular, the composition according to the present invention forms organic layers alternately stacked with the inorganic layers described below. To form organic layers with low dielectric constant and good plasma resistance in such an alternating stack structure, the composition according to the present invention is designed to have a post-cure dielectric constant of about 2.9 or less than 2.9.
In one embodiment, the photocuring rate of a composition according to the present invention can be evaluated by measuring the post-cure hardness (e.g., pencil hardness) of the composition. For details of the hardness measurement, reference is made to the experimental examples described below. The composition according to the invention may have a post-cure hardness of H or greater than H. Within this range, the composition may have a high light curing rate, and thus may improve the lifespan and reliability of the organic light emitting diode when used for an organic layer of the organic light emitting diode. Preferably, the composition according to the invention has a post-cure hardness of H to 3H. Within this range, the composition may improve the lifespan and reliability of the organic light emitting diode due to its high light curing rate, while reducing the dielectric constant of the organic layer.
The compositions according to the invention have a post-cure dielectric constant over a wide frequency range within the ranges specified herein. For example, compositions according to the present invention may have a post-cure dielectric constant of about 2.9 or less than 2.9 at frequencies of about 200 kilohertz to about 1 gigahertz (e.g., about 200 kilohertz to about 500 kilohertz).
In one embodiment, the composition according to the present invention may have good inkjet coatability. Here, the inkjet coating means applying the composition using an inkjet printer under the conditions of a drop rate of about 2.5 to about 3.5 microns/second and a head temperature of about 20 to 50 ℃.
A composition according to one embodiment of the present invention comprises a vinyl, allyl, or vinyl ether group-containing cationically polymerizable compound and a photoacid generator, wherein the vinyl, allyl, or vinyl ether group-containing cationically polymerizable compound is present in an amount of about 95 parts by weight to 99.9 parts by weight (e.g., 95.0 parts by weight, 95.1 parts by weight, 95.2 parts by weight, 95.3 parts by weight, 95.4 parts by weight, 95.5 parts by weight, 95.6 parts by weight, 95.7 parts by weight, 95.8 parts by weight, 95.9 parts by weight, 96.0 parts by weight, 96.1 parts by weight, 96.2 parts by weight, 96.3 parts by weight, 96.4 parts by weight, 96.5 parts by weight, 96.6 parts by weight, 96.7 parts by weight, 96.8 parts by weight, 96.9 parts by weight, 97.0 parts by weight, 97.1 parts by weight, 97.2 parts by weight, 97.3 parts by weight, 97.4 parts by weight, 97.5 parts by weight, 97.6 parts by weight, 97.7 parts by weight, 97.8 parts by weight, 97.9 parts by weight, 98.0 parts by weight, 98.1 parts by weight, 98.2 parts by weight, 98.3 parts by weight, 98.4 parts by weight, 98.5 parts by weight, 98.6 parts by weight, 98.8.9 parts by weight, 99.9 parts by weight, 99.0 parts by weight, 99.1 parts by weight, 99.3 parts by weight, or 99.4 parts by weight) is present. Within this range, the composition may have a high light curing rate and good inkjet coatability, and may form an organic layer having good plasma resistance and a low dielectric constant at a wide frequency range after curing. Preferably, the vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound may be present in an amount of about 97 parts by weight to 99.9 parts by weight, based on the solid content, relative to about 100 parts by weight of the composition.
Now, each component of the composition according to the present invention will be described in detail.
Cationically polymerizable compounds containing vinyl, allyl or vinyl ether groups
When present within the ranges specified herein, the vinyl, allyl, or vinyl ether group-containing cationically polymerizable compound increases the photocuring rate of the composition and decreases the dielectric constant of the organic layer obtained by curing the composition.
The vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound may comprise at least one selected from the group consisting of: a compound having an alicyclic group or an aromatic group and having at least one (preferably 1 to 2) vinyl group, allyl group or vinyl ether group in its molecular structure, and a compound having no alicyclic group or aromatic group and having at least one (preferably 1 to 2) vinyl group, allyl group or vinyl ether group in its molecular structure. These compounds may be used alone or in the form of a mixture thereof in a composition.
In the compound having an alicyclic group or aromatic group and having at least one (preferably 1 to 2) vinyl group, allyl group or vinyl ether group in its molecular structure, the alicyclic group means C composed of only carbon atoms not containing oxygen 5 To C 10 A cyclic functional group. The compound having an alicyclic group or an aromatic group and having at least one (preferably 1 to 2) vinyl group may include at least one selected from the group consisting of: divinylbenzene (including 1,2-divinylbenzene, 1,3-divinylbenzene, 1,4-divinylbenzene and combinations thereof), 1,4-cyclohexanedimethanol divinyl ether, allyl benzyl ether, and 5-vinyl bicyclo [2.2.1]Hept-2-ene.
The compound which does not contain an alicyclic group or an aromatic group and has at least one (preferably 1 to 2) vinyl group, allyl group or vinyl ether group in its molecular structure may comprise at least one selected from the group consisting of: diethylene glycol divinyl ether, 1-tetradecene, triethylene glycol divinyl ether, octadecyl vinyl ether, trimethylolpropane diallyl ether, and 1,4-butanediol divinyl ether.
In one embodiment, the vinyl, allyl, or vinyl ether group-containing cationically polymerizable compound can comprise at least one selected from the group consisting of: divinyl benzene (containing 1,2-divinyl benzene, 1,3-divinyl benzene, 1,4-divinyl benzene and combinations thereof), 1-tetradecene, diethylene glycol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, allyl benzyl ether, and combinations thereof.
Photoacid generators
The photoacid generator is used to photocure a cationic polymerizable compound containing a vinyl, allyl, or vinyl ether group to form an organic layer.
The photoacid generator is a compound that induces curing of a cationically polymerizable compound by generating a cationic species upon receiving light, and may include a cationic moiety that absorbs light and an anionic moiety that serves as a source of acid.
The photoacid generator may comprise at least one selected from the group consisting of: sulfonate compounds, sulfonium compounds, diazonium salt compounds, iodonium salt compounds, sulfonium salt compounds, phosphonium salt compounds, selenium salt compounds, oxonium salt compounds, ammonium salt compounds, and bromine salt compounds. For example, the photoacid generator can comprise at least one selected from among: n-hydroxynaphthalimide trifluoromethanesulfonate, thio-p-phenylenebis (4,4' -dimethyldiphenylsulfonium) bis-tetrakis (pentafluorophenyl) borate, (4-hydroxyphenyl) methylbenzylsulfonium tetrakis (pentafluorophenyl) borate, 4- (4-biphenylthio) phenyl-4-biphenylphenylsulfinium tetrakis (pentafluorophenyl) borate, 4- (phenylthio) phenyldiphenylsulfonium phenyltris (pentafluorophenyl) borate, [4- (4-biphenylthio) phenyl-4-biphenylphenylsulfinium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenylsulfonium ] hexafluoroantimonate, diphenyl [4- (phenylthio) phenyl ] sulfonium tris (pentafluoroethyl) trifluorophosphate, diphenyl [4- (phenylthio) phenyl ] sulfonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate, 4- (4-biphenylthio) phenyl-4-biphenylthio) phenylsulfinium tris (pentafluoroethyl) trifluorophosphate, bis [4- (diphenylsulfonium) phenyl ] thiophenyl ] tris (pentafluorophenyl) borate and [4- (2-diphenylthio) anthracenylsulfonium (2-anthrylthio) anthracenylsulfonium borate, but not limited thereto.
Preferably, the photoacid generator comprises at least one selected from the group consisting of: n-hydroxynaphthalimide trifluoromethanesulfonate, and thio-p-phenylenebis (4,4' -dimethyldiphenylsulfonium) bis-tetrakis (pentafluorophenyl) borate.
The photoacid generator may be present in an amount of 0.1 to 5 parts by weight, preferably 0.1 to 3 parts by weight, based on the solid content, relative to 100 parts by weight of the composition. Within this range, the cationic polymerizable compound having a vinyl group, an allyl group, or a vinyl ether group can have a high curing rate while preventing a decrease in light transmittance of the organic layer due to the residue of the photoacid generator.
The composition may further comprise a (meth) acrylic photocurable monomer.
(meth) acrylic acid photocurable monomer
The (meth) acrylic photocurable monomer may form an organic layer by curing. When the (meth) acrylic photocurable monomer is present in the composition in an appropriate amount such that the amount of the vinyl, allyl, or vinyl ether group-containing cationically polymerizable compound falls within the ranges specified herein, the composition according to the present invention can have a low post-cure dielectric constant and good inkjet coatability.
The (meth) acrylic photocurable monomer may be present in an amount of 50 parts by weight or less than 50 parts by weight, specifically about 10 parts by weight to 28 parts by weight, based on the solid content, relative to about 100 parts by weight of the composition. Within this range, the composition can have an increased photocuring rate, thereby allowing an organic layer formed from the composition to have an increased hardness and a dielectric constant within the ranges specified herein, while having good inkjet coatability.
The (meth) acrylic photocurable monomer may include a photocurable monomer having at least one (meth) acrylate group.
In one embodiment, the (meth) acrylic photocurable monomer may comprise at least one selected from the group consisting of: containing C 1 To C 15 Alkyl mono (meth) acrylates and C-containing 6 To C 15 Alkylene di (meth) acrylates.
Containing C 1 To C 15 The mono (meth) acrylate of an alkyl group may comprise at least one selected from the group consisting of: hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, and dodecyl (meth) acrylate (lauryl (meth) acrylate).
Containing C 6 To C 15 The di (meth) acrylate of the alkylene group may comprise C having a substitution or an unsubstituted, preferably an unsubstituted, between the (meth) acrylate groups 6 To C 15 Alkylene di (meth) acrylates. For example, di (meth) acrylates may be represented by formula 1:
(wherein R is 10 And R 11 Each independently is hydrogen or methyl and R 12 Is substituted or unsubstituted C 6 To C 15 Alkylene).
For example, in formula 1, R 12 May be unsubstituted C 6 To C 12 An alkylene group. The di (meth) acrylate may comprise at least one selected from the group consisting of: 1,6-hexanediol di (meth) acrylate, 1,8-octanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 1,11-undecanediol di (meth) acrylate, and 1,12-dodecanediol di (meth) acrylate.
The composition may further comprise a photo radical initiator.
Photo-radical initiator
The photo radical initiator may include any typical photo radical initiator that can initiate photo curing of the (meth) acrylic photo-curable monomer. For example, the photo radical initiator may comprise a triazine initiator, an acetophenone initiator, a benzophenone initiator, a thioxanthone initiator, a benzoin initiator, a phosphorous initiator, an oxime initiator, or mixtures thereof.
Examples of phosphorus initiators may include diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, benzyl (diphenyl) phosphine oxide, or mixtures thereof. The phosphorescent radical initiator is advantageously used to initiate photocuring of the composition upon irradiation with long wavelength UV. The aforementioned photo radical initiators may be used alone or in combination thereof.
The photo radical initiator may be present in an amount of 0.5 to 7 parts by weight, specifically 1 to 5 parts by weight or 2 to 4 parts by weight, based on the solid content, relative to 100 parts by weight of the composition. Within this range, the composition may be sufficiently cured upon exposure to light while preventing the organic layer from being lowered in light transmittance due to the residue of the photo radical initiator.
The composition according to the invention can be prepared by mixing the aforementioned components. Further, the composition according to the present invention may be formed in a solvent-free type without any solvent.
The composition according to the present invention is a photocurable composition and can be cured into an encapsulation layer (organic layer) by UV irradiation at a flux of 10 to 500 mw/cm for 1 to 50 seconds.
The composition according to the invention may further comprise typical additives known to the person skilled in the art. Examples of the additive may include a heat stabilizer, an antioxidant, and a UV absorber, but are not limited thereto.
The composition according to the invention can be used for encapsulating organic light-emitting diodes. In particular, the composition may form an organic layer in an encapsulation structure, wherein the organic layer and the inorganic layer are formed sequentially over each other.
For example, compositions according to the present invention can be used to encapsulate components of an apparatus (particularly, components of a display) that would otherwise suffer degradation or failure due to permeation of ambient gases or liquids (e.g., atmospheric oxygen and/or moisture and/or water vapor) and due to permeation of chemicals used to manufacture electronic products. Examples of components of an apparatus can include, but are not limited to, lamps, metal sensing pads, microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits, charge coupled devices, and light emitting polymers.
The organic light emitting diode display according to the present invention may include an organic layer formed of the composition for encapsulating an organic light emitting diode according to an embodiment of the present invention. In particular, an organic light emitting diode display may include an organic light emitting diode and a barrier stack formed on the organic light emitting diode and including an inorganic layer and an organic layer, wherein the organic layer may be formed of the composition for encapsulating the organic light emitting diode according to an embodiment of the present invention. Accordingly, the organic light emitting display may have high reliability.
Now, an organic light emitting diode display according to an embodiment of the present invention will be described with reference to fig. 1. Fig. 1 is a cross-sectional view of an organic light emitting diode display according to an embodiment of the present invention.
Referring to fig. 1, an organic light emitting display 100 according to this embodiment may include 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 abuts the organic light emitting diode 20, 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 substrate 10 is not particularly limited as long as the organic light emitting diode can be formed thereon. For example, the substrate 10 may include a transparent glass substrate, a plastic sheet substrate, a silicon substrate, a metal substrate, and the like.
The organic light emitting diode 20 may comprise any organic light emitting diode commonly used in organic light emitting diode displays. Although not shown in fig. 1, the organic light emitting diode 20 may include a first electrode, a second electrode, and an organic light emitting layer formed between the first and second electrodes. Here, 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 rib stack 30 includes an organic layer and an inorganic layer, wherein the organic layer and the inorganic layer are formed of different materials, thereby performing the respective functions of encapsulating the organic light emitting diode.
The inorganic layer may be formed of a different material than the organic layer to complement the encapsulation provided by the organic layer. For example, the inorganic layer may comprise 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; boron oxides of metals or non-metals; metal or non-metal silicides; and mixtures thereof. The metal or nonmetal may include, but is not limited to, silicon (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), bismuth (Bi), transition metals, and lanthanide metals. Specifically, the inorganic layer may be silicon oxide (SiO) x ) Silicon nitride (SiN) x ) Silicon oxynitride (SiO) x N y ) Zinc selenide (ZnSe), zinc oxide (ZnO), antimony trioxide (Sb) 2 O 3 ) Comprising aluminum oxide (Al) 2 O 3 ) Aluminum oxide (AlO) x ) Indium oxide (In) 2 O 3 ) Or tin oxide (SnO) 2 )。
The inorganic layer 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, or a combination thereof.
The organic layers are alternately deposited with the inorganic layers, thereby ensuring the smooth properties of the inorganic barrier layers while preventing the defects of one inorganic layer from diffusing to the other inorganic layers.
The organic layer may be formed by a combination of coating, deposition, and curing of the composition for encapsulating the organic light emitting diode according to an embodiment of the present invention. For example, the organic layer may be formed by: the composition is applied to a thickness of about 1 micron to about 50 microns and subsequently cured by light irradiation at a flux of about 10 milliwatts per square centimeter to about 500 milliwatts per square centimeter for about 1 second to 50 seconds.
The barrier stack may include any number of organic and inorganic layers. The total number of organic and inorganic layers may vary depending on the desired level of permeation resistance to oxygen and/or moisture and/or chemicals. For example, the organic and inorganic layers are formed in 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 with a total of 7 layers: inorganic layer/organic layer/inorganic barrier layer.
In the barrier stack, organic barrier layers and inorganic barrier layers may be alternately deposited. This is based on considering the benefits of the organic layer due to the aforementioned attributes of the composition. Thus, the organic and inorganic layers may complement or reinforce each other with respect to the components of the encapsulation device.
Next, an organic light emitting diode display according to another embodiment of the present invention will be described 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, an 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 is encapsulated in an inner space 40 in which the organic light emitting diode 20 is received, and the organic barrier 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 display 200 according to this embodiment is substantially the same as the organic light emitting display according to the above embodiment except that the inorganic layer is not adjacent to the organic light emitting diode.
Next, the present invention will be described in more detail with reference to some examples. It should be understood that these examples are provided for illustration only, and should not be construed as limiting the invention in any way.
The details of the components used in the examples and comparative examples are as follows:
a: cationically polymerizable compounds containing vinyl, allyl or vinyl ether groups
A1: 3238 Zxft 3238-Divinylbenzene and 1,4-Divinylbenzene mixture (TCI)
A2: 1-tetradecene (Aldrich Chemical Co., inc.)
A3: diethylene glycol divinyl ether (Aldrich chemical Co.)
A4:1,4 cyclohexanedimethanol divinyl Ether (Aldrich chemical Co.)
A5: allyl benzyl ether
B: (meth) acrylic acid photocurable monomer
B1:1,12-Dodecanediol diacrylate (Sartomer Co., inc.)
C: photoacid generators
C1: TR-PAG-21608 (thio-p-phenylene-bis (4,4' -dimethyldiphenylsulfonium) bis-tetrakis (pentafluorophenyl) borate, pioneer New Electronic Materials Co., ltd.)
C2: MIPHOTO NIT (n-hydroxynaphthalimide trifluoromethanesulfonate, miwon Corporation, inc.)
D: photo-radical initiator
D1: brilliant solid TPO (phosphorus initiator, BASF Corporation)
Example 1
99.9 parts by weight of (A1) and 0.1 part by weight of (C1) were put into a 125 ml brown polypropylene bottle, followed by mixing in a shaker at room temperature for 3 hours, to thereby prepare a composition.
Examples 2 to 10 and comparative examples 1 to 5
Compositions were prepared in the same manner as in example 1, except that the types and/or contents of (a), (B), (C), and (D) were changed as listed in table 1 (unit: parts by weight). In table 1, "-" means that the corresponding component was not used.
The details of the compositions prepared in the examples and comparative examples are shown in table 1.
TABLE 1
Each of the compositions prepared in the examples and comparative examples was evaluated with respect to the following attributes. The results are shown in table 2.
(1) Hardness of organic layer: each of the compositions prepared in examples and comparative examples was coated on a glass substrate, followed by curing by UV irradiation at a wavelength of 395 nm at a flux of 100 milliwatts/square centimeter for 10 seconds, thereby preparing an organic layer sample. The pencil hardness was measured on the prepared organic layer sample. In the measurement of pencil hardness, an electric pencil hardness tester (Lab-Q D a) and pencils of 6B to 9H (Mitsubishi co., ltd.) were used. Specifically, the pencil hardness was measured under load conditions on the specimen: 500 grams, scratch angle: 45 °, and scratch rate: 48 mm/min. When the sample had one or more scratches after 5 tests using a certain pencil, the pencil hardness was measured again using another pencil having a one-step lower pencil hardness than the previous pencil. The pencil hardness value that allowed no scratch observed on all five times of the sample was taken as the pencil hardness of the sample.
(2) Plasma etching rate of organic layer (unit:%): each of the compositions prepared in examples and comparative examples was deposited on a Si wafer, followed by curing by UV irradiation at a wavelength of 395 nm at a flux of 100 mw/cm for 10 seconds, thereby forming an organic layer. Next, the initial thickness (T1, unit: μm) of the formed organic layer was measured. Then, at ICP power: 2,500 watts, RE power: 300 Watts, DC bias: 200V, ar flow: 70 standard cubic centimeters per minute, etching time: 1 minute and pressure: the organic layer was subjected to ICP plasma treatment using an ICP-CVD apparatus (BMR technique) under a condition of 10 mtorr, and then the thickness (T2, unit: μm) of the organic layer was measured. The plasma etch rate of the organic layer was calculated according to equation 1:
post-cure etch rate (%) = { (T1-T2)/T1 } × 100.
(3) Dielectric constant: each of the compositions prepared in examples and comparative examples was coated to a predetermined thickness on a chromium (Cr) plate, followed by curing for 10 seconds by UV irradiation at a wavelength of 395 nm at a flux of 100 milliwatts/square centimeter, thereby forming a coating film 8 μm thick. An aluminum electrode (electrode for measuring dielectric constant) was deposited on the paint film, and then the dielectric constant of the paint film was measured using an impedance meter (RDMS-200) at 200 kilohertz and 25 ℃.
TABLE 2
* In table 2, "-" means that the corresponding composition failed to cure, and thus measurement of hardness, plasma etching rate, and dielectric constant was not possible.
As shown in table 2, the composition for encapsulating an organic light emitting diode according to the present invention has high post-cure hardness and thus high light-curing rate, and can form an organic layer having high light transmittance, good plasma resistance, and a low dielectric constant after curing.
In contrast, the compositions of comparative examples 1 to 3 (which do not contain a vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound and a photoacid generator) and the compositions of comparative examples 4 to 5 (which contain a vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound and a photoacid generator, but contain a vinyl, allyl, or vinyl ether group-containing cationic polymerizable compound in an amount outside the range set forth herein (about 95 parts by weight to about 99.9 parts by weight relative to about 100 parts of the composition) fail to achieve all of the benefits of the present invention.
It is to be understood that various modifications, alterations, adaptations, and equivalent embodiments may occur to one skilled in the art without departing from the spirit and scope of the present invention.
Claims (9)
1. A composition for encapsulating an organic light emitting diode, comprising a cationic polymerizable compound having a vinyl group, an allyl group or a vinyl ether group and a photoacid generator,
wherein the cationic polymerizable compound containing a vinyl group, an allyl group, or a vinyl ether group is present in an amount of 95 parts by weight to 99.9 parts by weight based on a solid content relative to 100 parts by weight of the composition.
2. A composition for encapsulating an organic light emitting diode according to claim 1, wherein the vinyl, allyl or vinyl ether group containing cationically polymerizable compound comprises at least one selected from the group consisting of: a compound having an alicyclic group or an aromatic group and having at least one vinyl group, allyl group or vinyl ether group in its molecular structure, and a compound having no alicyclic group or aromatic group and having at least one vinyl group, allyl group or vinyl ether group in its molecular structure.
3. A composition for encapsulating an organic light emitting diode according to claim 2, wherein said vinyl, allyl or vinyl ether group containing cationically polymerizable compound comprises at least one selected from the group consisting of: divinylbenzene, 1,4-cyclohexanedimethanol divinyl ether, allyl benzyl ether, and 5-vinylbicyclo [2.2.1] hept-2-ene, diethylene glycol divinyl ether, 1-tetradecene, triethylene glycol divinyl ether, octadecyl vinyl ether, trimethylolpropane diallyl ether, and 1,4-butanediol divinyl ether.
4. The composition for encapsulating an organic light emitting diode according to claim 1, wherein the photoacid generator comprises at least one selected from the group consisting of: n-hydroxynaphthalimide trifluoromethanesulfonate and thio-p-phenylene bis (4,4' -dimethyldiphenylsulfonium) bis-tetrakis (pentafluorophenyl) borate.
5. The composition for encapsulating an organic light emitting diode according to claim 1, wherein the photoacid generator is present in an amount of 0.1 to 5 parts by weight relative to 100 parts by weight of the composition in terms of solid content.
6. The composition for encapsulating an organic light emitting diode according to claim 1, further comprising a (meth) acrylic photocurable monomer, wherein the (meth) acrylic photocurable monomer is present in an amount of 50 parts by weight or less than 50 parts by weight relative to about 100 parts by weight of the composition in terms of solid content.
7. The composition for encapsulating an organic light emitting diode according to claim 1, wherein the composition has a post-cure dielectric constant of 2.9 or less than 2.9.
8. The composition for encapsulating an organic light emitting diode of claim 1, wherein the composition has a post cure plasma etch rate of 10% or less than 10% as calculated according to equation 1:
post-cure plasma etch rate (%) = { (T1-T2)/T1 }. Times.100' - - (1)
Wherein T1 indicates an initial thickness in micrometers of an organic layer obtained by depositing the composition on a silicon wafer followed by curing by light irradiation at a flux of 100 milliwatts per square centimeter for 10 seconds, and T2 indicates a thickness in micrometers of the organic layer after an inductively coupled plasma process by inductively coupled plasma chemical vapor deposition under conditions of an inductively coupled plasma power of 2,500 watts, an RE power of 300 watts, a direct current bias of 200 volts, an argon flow rate of 70 standard cubic centimeters per minute, an etching time of 1 minute, and a pressure of 10 millitorr.
9. An organic light emitting diode display comprising an organic layer formed from the composition for encapsulating organic light emitting diodes as claimed in any one of claims 1 to 8.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020200066884A KR102541648B1 (en) | 2020-06-03 | 2020-06-03 | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same |
| KR10-2020-0066884 | 2020-06-03 | ||
| CN202110615130.6A CN113755046B (en) | 2020-06-03 | 2021-06-02 | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110615130.6A Division CN113755046B (en) | 2020-06-03 | 2021-06-02 | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115678326A true CN115678326A (en) | 2023-02-03 |
Family
ID=78787391
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211458816.XA Pending CN115678326A (en) | 2020-06-03 | 2021-06-02 | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom |
| CN202110615130.6A Active CN113755046B (en) | 2020-06-03 | 2021-06-02 | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110615130.6A Active CN113755046B (en) | 2020-06-03 | 2021-06-02 | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2021190428A (en) |
| KR (1) | KR102541648B1 (en) |
| CN (2) | CN115678326A (en) |
| TW (1) | TWI794827B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0408227A1 (en) * | 1989-06-30 | 1991-01-16 | The Mead Corporation | Photohardenable or photosoftenable compositions |
| WO1991011467A1 (en) * | 1990-01-26 | 1991-08-08 | Isp Investments Inc. | Alkenyl ethers and radiation curable compositions |
| US5070117A (en) * | 1990-06-25 | 1991-12-03 | Loctite Corporation | Aromatic vinyl ether compounds and compositions, and method of making the same |
| US5106885A (en) * | 1989-11-03 | 1992-04-21 | Isp Investments Inc. | Radiation curable compositions containing multifunctional vinyl ether monomers and protective coatings formed therefrom |
| US20080045618A1 (en) * | 2006-06-27 | 2008-02-21 | Nagvekar Devdatt S | Low viscosity UV curable ink formulations |
| CN102299118A (en) * | 2011-05-20 | 2011-12-28 | 电子科技大学 | Method for packaging photoelectronic device |
| JP2012017368A (en) * | 2010-07-06 | 2012-01-26 | Sekisui Chem Co Ltd | Sealing agent for optical device |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100404578C (en) * | 2003-08-12 | 2008-07-23 | 三井化学株式会社 | Photo-curable resin composition and sealing agent for flat panel display using the same |
| JP2008013721A (en) * | 2006-07-10 | 2008-01-24 | Kyocera Chemical Corp | Curable resin composition, adhesive for display element, and method for adhesion |
| DE102009013710A1 (en) * | 2009-03-20 | 2010-09-23 | Merck Patent Gmbh | Polymers from blends with vinyl ether monomers |
| KR20120109558A (en) * | 2009-12-17 | 2012-10-08 | 디에스엠 아이피 어셋츠 비.브이. | Liquid radiation curable resins for additive fabrication comprising a triaryl sulfonium borate cationic photoinitiator |
| CN102214803B (en) * | 2011-05-20 | 2013-07-17 | 电子科技大学 | Packaging method of photoelectronic device |
| JP6103653B2 (en) * | 2012-05-15 | 2017-03-29 | 株式会社Adeka | Photocurable resin composition |
| CN105246940B (en) * | 2013-05-28 | 2018-09-04 | 株式会社大赛璐 | Optical semiconductor sealing solidification compound |
| JP2015124286A (en) * | 2013-12-26 | 2015-07-06 | 株式会社ダイセル | Curable composition |
| JP5972433B1 (en) * | 2015-07-21 | 2016-08-17 | 古河電気工業株式会社 | Curable hygroscopic resin composition for electronic device sealing, resin cured product, and electronic device |
| JPWO2017099055A1 (en) * | 2015-12-08 | 2018-09-27 | 株式会社ダイセル | Sealing composition |
| JP6378450B2 (en) * | 2016-09-16 | 2018-08-22 | 積水化学工業株式会社 | Sealant for organic electroluminescence display element |
| KR102017269B1 (en) * | 2016-12-09 | 2019-09-03 | 주식회사 엘지화학 | Encapsulating composition |
| JP6228289B1 (en) * | 2016-12-28 | 2017-11-08 | 株式会社ダイセル | Composition for sealing an organic electroluminescence device |
-
2020
- 2020-06-03 KR KR1020200066884A patent/KR102541648B1/en active IP Right Grant
-
2021
- 2021-05-28 JP JP2021089926A patent/JP2021190428A/en active Pending
- 2021-05-31 TW TW110119661A patent/TWI794827B/en active
- 2021-06-02 CN CN202211458816.XA patent/CN115678326A/en active Pending
- 2021-06-02 CN CN202110615130.6A patent/CN113755046B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0408227A1 (en) * | 1989-06-30 | 1991-01-16 | The Mead Corporation | Photohardenable or photosoftenable compositions |
| US5106885A (en) * | 1989-11-03 | 1992-04-21 | Isp Investments Inc. | Radiation curable compositions containing multifunctional vinyl ether monomers and protective coatings formed therefrom |
| WO1991011467A1 (en) * | 1990-01-26 | 1991-08-08 | Isp Investments Inc. | Alkenyl ethers and radiation curable compositions |
| US5070117A (en) * | 1990-06-25 | 1991-12-03 | Loctite Corporation | Aromatic vinyl ether compounds and compositions, and method of making the same |
| US20080045618A1 (en) * | 2006-06-27 | 2008-02-21 | Nagvekar Devdatt S | Low viscosity UV curable ink formulations |
| JP2012017368A (en) * | 2010-07-06 | 2012-01-26 | Sekisui Chem Co Ltd | Sealing agent for optical device |
| CN102299118A (en) * | 2011-05-20 | 2011-12-28 | 电子科技大学 | Method for packaging photoelectronic device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102541648B1 (en) | 2023-06-08 |
| CN113755046B (en) | 2022-12-13 |
| TW202146467A (en) | 2021-12-16 |
| KR20210150021A (en) | 2021-12-10 |
| JP2021190428A (en) | 2021-12-13 |
| TWI794827B (en) | 2023-03-01 |
| CN113755046A (en) | 2021-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20150252125A1 (en) | Curable resin compositions and barrier stacks including the same | |
| EP3023444B1 (en) | Composition for fabricating organic film, organic light-emitting display apparatus manufactured using the same, and method of manufacturing the organic light-emitting display apparatus | |
| CN104540676B (en) | Coating for barrier film and preparation and use its method | |
| CN110894361B (en) | Photocuring packaging composition, packaging structure and semiconductor device | |
| CN104768758A (en) | Barrier film, method of making the barrier film, and articles including the barrier film | |
| US11289666B2 (en) | Electrically conductive siloxane particle films, and devices with the same | |
| JP2020019953A (en) | Pressure sensitive adhesive sheet for display, and display including the same | |
| KR20160150257A (en) | Organic light emmiting diode display apparatus | |
| KR20190065896A (en) | Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same | |
| CN113755046B (en) | Composition for encapsulating organic light emitting diode and organic light emitting diode display including organic layer formed therefrom | |
| KR20180102038A (en) | Photo-curable composition, organic protective layer comprising the same, and apparatus comprising the same | |
| US20220002569A1 (en) | Encapsulating composition | |
| TWI759752B (en) | Composition for encapsulating organic light emitting diode device and display device | |
| CN107922657A (en) | Composite product and its manufacture method including multilayer barrier components | |
| JP2018104699A (en) | Polymerizable composition for encapsulation, organic optical device with polymer of the polymerizable composition for encapsulation mounted | |
| US11945894B2 (en) | Dielectric film-forming composition | |
| KR20220134393A (en) | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same | |
| CN117940470A (en) | Composition for encapsulating organic light emitting element and organic light emitting element display device including organic layer produced therefrom | |
| KR20230040856A (en) | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same | |
| KR20210147747A (en) | Photocurable Ink Composition, Encapsulation Layer and Display Device | |
| US20230006135A1 (en) | Composition for encapsulating organic light emitting diode and organic light emitting diode display comprising organic layer formed using the same | |
| KR102654811B1 (en) | Hardcoating composition, hard coating layer and cover window using the same | |
| KR20230022644A (en) | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same | |
| KR20230042993A (en) | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same | |
| KR20220118228A (en) | Photocurable Ink Composition, Encapsulation Layer and Display Device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |