CN112898330A - Compound for packaging organic light-emitting device and preparation method and application thereof - Google Patents
Compound for packaging organic light-emitting device and preparation method and application thereof Download PDFInfo
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- CN112898330A CN112898330A CN202010748628.5A CN202010748628A CN112898330A CN 112898330 A CN112898330 A CN 112898330A CN 202010748628 A CN202010748628 A CN 202010748628A CN 112898330 A CN112898330 A CN 112898330A
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- compound
- organic light
- emitting device
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- -1 propenyl compound Chemical class 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 238000005538 encapsulation Methods 0.000 claims abstract description 37
- 239000012044 organic layer Substances 0.000 claims abstract description 26
- 239000003999 initiator Substances 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 239000010410 layer Substances 0.000 claims description 36
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000012965 benzophenone Substances 0.000 claims description 5
- 125000004386 diacrylate group Chemical group 0.000 claims description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000686 lactone group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 244000028419 Styrax benzoin Species 0.000 claims description 3
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 3
- PSDYQSWHANEKRV-UHFFFAOYSA-N [S]N Chemical compound [S]N PSDYQSWHANEKRV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229960002130 benzoin Drugs 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 235000019382 gum benzoic Nutrition 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 30
- 239000010409 thin film Substances 0.000 abstract description 9
- 238000002834 transmittance Methods 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 235000010290 biphenyl Nutrition 0.000 description 29
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 26
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 26
- 230000005540 biological transmission Effects 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 230000035699 permeability Effects 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 10
- OJMGRYVFDTYXRP-UHFFFAOYSA-N CC(=C)C(=O)OCCCCCCCCC=CC=C Chemical group CC(=C)C(=O)OCCCCCCCCC=CC=C OJMGRYVFDTYXRP-UHFFFAOYSA-N 0.000 description 10
- BSXVSQHDSNEHCJ-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-diphenylsilyl]oxy-dimethylsilicon Chemical compound C=1C=CC=CC=1[Si](O[Si](C)C)(O[Si](C)C)C1=CC=CC=C1 BSXVSQHDSNEHCJ-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 229920006280 packaging film Polymers 0.000 description 7
- 239000012785 packaging film Substances 0.000 description 7
- 229910052581 Si3N4 Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 6
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 5
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- ISNPECFCDXWIMG-UHFFFAOYSA-N diphenylphosphoryl-[2,4,6-tris(hydroxymethyl)phenyl]methanone Chemical compound OCC1=CC(CO)=CC(CO)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 ISNPECFCDXWIMG-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000009975 flexible effect Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 3
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- HZBDPZBVINJJET-UHFFFAOYSA-N bis(dimethylsilyloxy)-dimethylsilane Chemical compound C[SiH](C)O[Si](C)(C)O[SiH](C)C HZBDPZBVINJJET-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000011895 specific detection Methods 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- AVOYQFVUKGBTEG-UHFFFAOYSA-N 2-methylidene-5-phenylsulfanylpentanoic acid Chemical compound OC(=O)C(=C)CCCSC1=CC=CC=C1 AVOYQFVUKGBTEG-UHFFFAOYSA-N 0.000 description 2
- CPERBTOOFYMBSW-UHFFFAOYSA-N C1(=CC=CC=C1)C1N(C(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl Chemical compound C1(=CC=CC=C1)C1N(C(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl CPERBTOOFYMBSW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- XCLIHDJZGPCUBT-UHFFFAOYSA-N dimethylsilanediol Chemical compound C[Si](C)(O)O XCLIHDJZGPCUBT-UHFFFAOYSA-N 0.000 description 2
- OIMIXJLPIJKPDM-UHFFFAOYSA-N dodeca-9,11-dien-1-ol Chemical compound OCCCCCCCCC=CC=C OIMIXJLPIJKPDM-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- RFDIBSNFDIXDCJ-UHFFFAOYSA-N 1,3-bis[2-[(2-methylpropan-2-yl)oxy]propan-2-yl]benzene Chemical compound CC(C)(C)OC(C)(C)C1=CC=CC(C(C)(C)OC(C)(C)C)=C1 RFDIBSNFDIXDCJ-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- DQMOHZLFVGYNAN-UHFFFAOYSA-N 2-(2-phenylethenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=CC=2C=CC=CC=2)=N1 DQMOHZLFVGYNAN-UHFFFAOYSA-N 0.000 description 1
- SHRXHKBJUMSIMF-UHFFFAOYSA-N 2-(2-phenylethenyl)-4-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC(C=CC=2C=CC=CC=2)=N1 SHRXHKBJUMSIMF-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- MPNIGZBDAMWHSX-UHFFFAOYSA-N 2-(4-methylphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MPNIGZBDAMWHSX-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- NQOGBCBPDVTBFM-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)COC(C)CO NQOGBCBPDVTBFM-UHFFFAOYSA-N 0.000 description 1
- ZJRNXDIVAGHETA-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 ZJRNXDIVAGHETA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- YZFQAGVDQHROCY-UHFFFAOYSA-N 2-methylidene-4-phenoxybutanoic acid Chemical compound OC(=O)C(=C)CCOC1=CC=CC=C1 YZFQAGVDQHROCY-UHFFFAOYSA-N 0.000 description 1
- JDVQPDVVINVPNR-UHFFFAOYSA-N 2-methylidene-5-naphthalen-2-yloxypentanoic acid Chemical compound C1=CC=CC2=CC(OCCCC(=C)C(=O)O)=CC=C21 JDVQPDVVINVPNR-UHFFFAOYSA-N 0.000 description 1
- XYCOIUGDAJORBK-UHFFFAOYSA-N 2-methylidene-5-phenoxypentanoic acid Chemical compound OC(=O)C(=C)CCCOC1=CC=CC=C1 XYCOIUGDAJORBK-UHFFFAOYSA-N 0.000 description 1
- ZQTNHZHZSGBHCV-UHFFFAOYSA-N 2-methylidene-6-phenoxyhexanoic acid Chemical compound OC(=O)C(=C)CCCCOC1=CC=CC=C1 ZQTNHZHZSGBHCV-UHFFFAOYSA-N 0.000 description 1
- FRIXCIPXTGZTQF-UHFFFAOYSA-N 2-methylidene-7-phenoxyheptanoic acid Chemical compound OC(=O)C(=C)CCCCCOC1=CC=CC=C1 FRIXCIPXTGZTQF-UHFFFAOYSA-N 0.000 description 1
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- 238000000231 atomic layer deposition Methods 0.000 description 1
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- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 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
- 238000007735 ion beam assisted deposition Methods 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
- C07F7/0879—Hydrosilylation reactions
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- 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
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- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Abstract
The invention discloses a compound for packaging an organic light-emitting device, and a preparation method and application thereof, belonging to the technical field of thin film packaging of organic light-emitting devices. Meanwhile, the invention also provides a composition prepared from the compound L, the propenyl compound and one or more of the photopolymerization initiator and the free radical polymerization initiator, and when the composition is applied to the encapsulation of the organic light-emitting device, the encapsulation film can show low transmittance of oxygen and moisture, so that the service life of the organic light-emitting device is prolonged, and the enhancement is thatEtching resistance of the organic layer to plasma to obtain an encapsulation composition of an organic/inorganic hybrid encapsulation film having higher flatness, an encapsulation film, and a display device using the same.
Description
Technical Field
The invention relates to the technical field of organic light-emitting device thin film packaging, in particular to a compound for packaging an organic light-emitting device and a preparation method and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) are considered to be one of the most promising display technologies because of their advantages of self-brightness, fast response, wide viewing angle, ultra-thin, high definition, and durability. In particular, OLEDs are particularly suitable for flexible displays, and are widely accepted as next generation Cathode Ray Tubes (CRTs) and Flat Panel Displays (FPDs). In the case of OLED technology, device encapsulation is the most demanding task, since OLEDs require a high degree of protection against moisture and oxygen penetration. Therefore, a high performance gas diffusion barrier is a crucial factor for improving the reliability and lifetime of OLEDs. The conventional encapsulation method is to encapsulate the OLED device with a glass cover or metal in an inert atmosphere, but the encapsulation material in the prior art is hard and cannot be used on a flexible OLED display screen.
In recent years, Thin Film Encapsulation (TFE) has been widely developed for flexible encapsulation, and the TFE method has advantages of being thinner and lighter, and has higher flexibility in the form of equipment when used. Several inorganic thin film barrier layers have been developed for OLED encapsulation, such as Si3N4，SiO2，Al2O3And TiO2. However, thin flame retardants consisting of a single layer generally exhibit high Water Vapor Transmission Rates (WVTR) due to film defects caused by the deposition process and stress when increasing the film thicknessIs caused by the cracks of (1).
Therefore, how to provide an organic light emitting device encapsulation film with low water vapor transmission rate is a problem that needs to be solved urgently by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention provides a compound for encapsulating an organic light emitting device and a photocurable composition using the same, which can reduce the transmittance of water vapor and gas after curing and encapsulating to lengthen the lifetime of a display device, and which has low shrinkage stress after curing to prevent any deviation from occurring. In addition, the composition is beneficial to various designs of organic light-emitting display equipment after being cured and packaged, and the organic light-emitting device can be thinned.
In order to achieve the purpose, the invention adopts the following technical scheme:
a compound for use in encapsulation of an organic light emitting device, the compound having a structural formula as follows:
wherein R1 to R6 are independently selected from hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted lactone groups, substituted or unsubstituted carboxyl groups, substituted or unsubstituted glycidyl ether groups, or hydroxyl groups;
Y1-Y4 are independently selected from alkyl;
z1 and Z2 are independently selected from hydrogen or methyl;
the X1 and X2 are independently selected from oxygen, amino, sulfur, group 1, group 2 or group 3; wherein the group 1, the group 2 and the group 3 are shown as follows:
preferably, R1-R6 are each independently substituted or unsubstituted C1～C10Alkyl, substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C6～C20Aryl, substituted or unsubstituted C2～C20Heteroaryl, substituted or unsubstituted C2～C10Alkenyl, substituted or unsubstituted C1～C10An alkoxy group, a substituted or unsubstituted lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, or a hydroxyl group; Y1-Y4 are independently selected from C1-C10Alkyl group of (1).
The compound provided by the invention can reduce the permeability of water vapor and gas after curing and packaging, prolong the service life of a display device, and reduce the shrinkage stress of the composition after curing, thereby realizing no deviation. In addition, the composition prepared from the compound is beneficial to the diversified designs of organic light-emitting display equipment after being cured and packaged, so that the organic light-emitting device can be thinned.
A method of preparing a compound for encapsulation of an organic light emitting device, comprising the steps of:
1) mixing the compound D1, the compound D2 and p-toluenesulfonic acid, and reacting at 25 ℃ for 24 hours to obtain a compound D3;
wherein the mass ratio of the compound D1 to the compound D2 to the p-toluenesulfonic acid is as follows: (4-8) to 5; the using concentration of the p-toluenesulfonic acid is 99 percent;
2) dissolving a compound D3 and a compound D4 in ethyl acetate, adding a catalyst, and reacting at 80 ℃ for 4 hours to obtain a compound D5;
wherein the mass ratio of the compound D3 to the compound D4 to the ethyl acetate is as follows: (20-30) to 17: 250; the ethyl acetate is used at a concentration of 99.5%;
3) adding the compound D5 and the compound D6 into a toluene solution, and stirring and reacting at 50 ℃ for 6 hours to obtain a compound L;
wherein the mass ratio of the compound D5 to the compound D6 to the toluene solution is as follows: (30-50) to 9: 120; the concentration of the toluene solution is 99.5%;
the specific synthetic route is as follows:
preferably, the catalyst in the step (2) is tetramethyl divinyl disiloxane, and the mass ratio of the compound D3, the compound D4 and the catalyst is (20-30) to 17: 0.15.
The catalyst in the invention is selected from a Karstard catalyst, namely tetramethyldivinyldisiloxane.
The preparation method provided by the invention has simple process, is convenient for purifying the product, and finally obtains the high-purity product.
The composition for packaging the organic light-emitting device is characterized by comprising the following raw materials in percentage by mass: 5-70% of component A, 25-95% of component B and 0.5-10% of component C;
the component A is a compound for packaging an organic light-emitting device;
the component B comprises one or more propenyl compounds;
the component C comprises more than one compound which can generate free radicals and generate acid under the action of light or heat;
the invention can fully generate curing during exposure in the film forming process, thereby obtaining excellent reliability and preventing the problem of low transmittance caused by unreacted initiator.
Preferably, the acryl-based compound includes one or more of an acrylate-based monomer and an acrylic-based monomer;
the acrylic monomer may include 2-phenoxyethylacrylic acid, 2-phenoxyethyl (meth) acrylic acid, 3-phenoxypropylacrylic acid, 3-phenoxypropyl (meth) acrylic acid, 4-phenoxybutylacrylic acid, 4-phenoxybutyl (meth) acrylic acid, 5-phenoxypentylacrylic acid, 5-phenoxypentyl (meth) acrylic acid, 6-phenoxyhexylacrylic acid, 6-phenoxyhexyl (meth) acrylic acid, 7-phenoxyheptylacrylic acid, 7-phenoxyheptyl (meth) acrylic acid, 8-phenoxyoctylacrylic acid, 8-phenoxyoctyl (meth) acrylic acid, 9-phenoxynonylacrylic acid, 10-phenoxydecylacrylic acid, p-phenoxybutylacrylic acid, p-, 10-phenoxydecyl (meth) acrylic acid, 2- (phenylthio) ethacrylic acid, 2- (phenylthio) ethyl (meth) acrylic acid, 3- (phenylthio) propylacrylic acid, 3- (phenylthio) propyl (meth) acrylic acid, 4- (phenylthio) butylacrylic acid, 4- (phenylthio) butyl (meth) acrylic acid, 5- (phenylthio) pentylacrylic acid, 5- (phenylthio) pentyl (meth) acrylic acid, 6- (phenylthio) hexylacrylic acid, 6- (phenylthio) hexyl (meth) acrylic acid, 7- (phenylthio) heptylacrylic acid, 7- (phenylthio) heptylp (meth) acrylic acid, 8- (phenylthio) octylacrylic acid, 8- (phenylthio) octyl (meth) acrylic acid, 9- (phenylthio) nonylacrylic acid, 2- (phenylthio) ethyl (meth) acrylic acid, 3- (phenylthio) propylacrylic acid, 3- (phenylthio) propyl (meth) acrylic, 9- (phenylthio) nonyl (meth) acrylic acid, 10- (phenylthio) decyl (meth) acrylic acid, 2- (naphthalen-2-yloxy) ethacrylic acid, 2- (naphthalen-2-yloxy) ethyl (meth) acrylic acid, 3- (naphthalen-2-yloxy) propylacrylic acid, 3- (naphthalen-2-yloxy) propyl (meth) acrylic acid, 4- (naphthalen-2-yloxy) butylacrylic acid, 4- (naphthalen-2-yloxy) butyl (meth) acrylic acid, 5- (naphthalen-2-yloxy) pentylacrylic acid, 5- (naphthalen-2-yloxy) pentyl (meth) acrylic acid, 6- (naphthalen-2-yloxy) hexylacrylic acid, acrylic acid, 6- (naphthalene-2-yloxy) hexyl (meth) acrylic acid, 7- (naphthalene-2-yloxy) heptyl (meth) acrylic acid, and 8- (naphthalene-2-yloxy) octyl acrylic acid.
The acrylate-based monomer comprises one or more of a monoacrylate monomer, a diacrylate monomer and a triacrylate monomer;
the monoacrylate monomer comprises lauryl acrylate, isobornyl methacrylate and tripropylene glycol acrylate;
the diacrylate monomer comprises one or more of dodecyl dimethacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, propoxylated hexanediol diacrylate and tricyclodecane dimethanol diacrylate;
any suitable acrylate-based monomer may be used for the triacrylate monomers, including trimethylolpropane triacrylate and ethoxylated trimethylolpropane triacrylate.
The monoacrylate, diacrylate and triacrylate monomers of the present invention can increase the degree of crosslinking in the cured polymer film.
Preferably, the compound which receives or generates a radical and generates an acid is one or more of a photopolymerization initiator and a radical polymerization initiator.
The photopolymerization initiator may be used to cause the curing of the acrylate monomer to form the organic barrier layer, and may include one or more of an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazonium compound, an imidazole compound, and a non-imidazole compound;
the acetophenone compound comprises one or more of 2, 2-diethoxy-acetophenone, 2' -dibutoxyacetophenone, 2-hydroxy-2-methyl propiophenone, 4-tert-butyl trichloroacetophenone, 4-tert-butyl dichloroacetophenone, 4-chloroacetophenone, 2-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1-one and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one;
the benzophenone compound comprises one or more of benzophenone, benzoyl benzoic acid methyl, 4-phenyl benzophenone, hydroxybenzophenone, acrylic acid benzophenone, 4 ' -di (dimethylamino) benzophenone, 4 ' -di (diethylamino) benzophenone, 4 ' -dimethylamino benzophenone, 4 ' -dichloro benzophenone and 3, 3 ' -dimethylamino-2-methoxy benzophenone;
examples of the thioxanthone-based compound are: thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chlorothioxanthone, and the like. Examples of the above-mentioned benzil ketone compound include: one or more of benzil ketone, benzil ketone methyl ether, benzil ketone ethyl ether, benzil ketone isopropyl ether, benzil ketone isobutyl ether and benzyl dimethyl ketal;
the triazine compounds comprise cyanuric chloride, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4 ' -dimethoxystyryl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4 ' -methoxynaphthalene) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methylphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-diphenyl-4, 6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, trichloromethyl-2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, trichloromethyl-6-styryl-s-triazine, trichloromethyl-2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (naphthalene-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy naphthalene-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2-4-trichloromethyl (piperazinylcarbonyl) -6-triazine, 2-4-trichloromethyl (4' -methoxy styryl) -6-triazine;
the free radical polymerization initiator comprises one or more of peroxide compounds and bisazo compounds.
The peroxide compounds comprise ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, acetylacetone peroxide and the like; diacyl peroxides such as isobutyryl peroxide, 2, 4-dichlorobenzoyl peroxide, O-methylbenzoyl peroxide, and di-3, 5, 5-trimethylhexanoyl peroxide, peroxides such as 2, 4, 4-trimethylpentyl-2-hydroperoxide, diisopropylbenzene hydroperoxide, cumene peroxide, and t-butyl peroxide, and dialkylperoxides such as dicumyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, 1, 3-di (t-butyloxyisopropyl) benzene, and n-butyl t-butylperoxyvalerate; 2, 4, 4-trimethylpentoxyphenoxyacetate, isopropyl phenyl alpha-peroxyneodecanoate and tert-butyl peroxybenzoate. One or more of alkyl perester such as di-tert-butylperoxytrimethyl adipate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, bis-4-tert-butylcyclohexyl peroxydicarbonate, diisopropyl peroxydicarbonate, acetylcyclohexylsulfonyl peroxide, tert-butylperoxyaryl carbonate, and the like;
examples of the bisazo-based compound include 1, 1 ' -azobiscyclohexane-1-carbonitrile, 2 ' -azobis (2, 4-dimethylvaleronitrile), 2-azobis (methyl isobutyrate), 2 ' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), α ' -azobis (isobutyronitrile), 4 ' -azobis (4-cyanovaleric acid), and the like.
The initiator can be used together with a photosensitizer which absorbs light to expand and then transfers energy to generate chemical reaction, and the photosensitizer comprises one or more of tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-mercaptopropionate and dipentaerythritol tetra-3-mercaptopropionate.
A preparation method of the composition for packaging the organic light-emitting device is characterized by comprising the following steps: and weighing the component A, the component B and the component C according to the proportion, mixing, uniformly mixing under a vacuum condition, and filtering to obtain the composition for packaging the organic light-emitting device.
An encapsulation film includes inorganic layers, and an organic layer coated between the inorganic layers; wherein the organic layer is the composition for encapsulating the organic light-emitting device.
The organic layer may be used on a monomer group having one or more photo-curable or thermosetting monomers, in addition to the compound L. Such a monomer or a monomer group is formed by a process of mixing a solid or a liquid, a thermal and photo-radical initiator, a thermal and photo-acid generator, applying the mixture by ink jet, electron spray, electron emission, or the like, and then molding the mixture by ultraviolet irradiation or thermal curing.
The inorganic Layer forms metal oxides and nitrides by sputtering cvd (chemical Vapor deposition), ald (atomic Layer deposition), ibad (ion Beam Assisted deposition), and the like.
The inorganic layer includes calcium oxide, aluminum oxide, titanium oxide, indium oxide, tin oxide, silicon nitride, silicon oxynitride, aluminum nitride, or zirconium oxide.
Preferably, the inorganic layer of the encapsulation film is disposed on one or both surfaces of the organic layer.
An organic light-emitting device comprising the above encapsulation film.
A method of packaging comprising the steps of: the composition for encapsulating an organic light emitting device is directly coated on the organic light emitting device or an encapsulation film is directly attached on the organic light emitting device.
According to the technical scheme, compared with the prior art, the compound for packaging the organic light-emitting device, the preparation method and the application are provided. And the thin film in which the inorganic layer and the organic layer are repeatedly alternately stacked exhibits a low Water Vapor Transmission Rate (WVTR) and a flexible property.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 is a schematic diagram of a packaging film according to an embodiment of the invention;
which comprises the following steps: an inorganic layer 11 and an organic layer 12.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the accompanying drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The embodiment of the invention discloses a compound for packaging an organic light-emitting device, which has the following structural formula:
wherein R1 to R6 are independently selected from hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted lactone groups, substituted or unsubstituted carboxyl groups, substituted or unsubstituted glycidyl ether groups, or hydroxyl groups;
Y1-Y4 are independently selected from alkyl;
z1 and Z2 are independently selected from hydrogen or methyl;
x1 and X2 are independently selected from oxygen, amino, sulfur, group 1, group 2, or group 3; wherein the group 1, the group 2 and the group 3 are shown as follows:
for further optimizing the technical scheme, R1-R6 are independently selected from substituted or unsubstituted C1～C10Alkyl, substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C6～C20Aryl, substituted or unsubstituted C2～C20Heteroaryl, substituted or unsubstituted C2～C10Alkenyl, substituted or unsubstituted C1～C10An alkoxy group; Y1-Y4 are independently selected from C1-C10Alkyl group of (1).
The embodiment of the invention also discloses a preparation method of the compound for packaging the organic light-emitting device, which comprises the following steps:
1) mixing the compound D1, the compound D2 and p-toluenesulfonic acid, and reacting at 25 ℃ for 24 hours to obtain a compound D3;
wherein the mass ratio of the compound D1 to the compound D2 to the p-toluenesulfonic acid is as follows: (4-8) to 5; the using concentration of the p-toluenesulfonic acid is 99 percent;
2) dissolving a compound D3 and a compound D4 in ethyl acetate, adding a catalyst, and reacting at 80 ℃ for 4 hours to obtain a compound D5;
wherein the mass ratio of the compound D3 to the compound D4 to the ethyl acetate is as follows: (20-30) to 17: 250; the ethyl acetate is used at a concentration of 99.5%;
3) adding the compound D5 and the compound D6 into a toluene solution, and stirring and reacting at 50 ℃ for 6 hours to obtain a compound L;
wherein the mass ratio of the compound D5 to the compound D6 to the toluene solution is as follows: (30-50) to 9: 120; the concentration of the toluene solution is 99.5%;
the specific synthetic route is as follows:
in order to further optimize the technical scheme, the catalyst in the step (2) is tetramethyl divinyl disiloxane, and the mass ratio of the compound D3, the compound D4 and the catalyst is (20-30) to 17: 0.15.
The embodiment of the invention also discloses a composition for packaging the organic light-emitting device, which comprises the following raw materials in percentage by mass: 5-70% of component A, 25-95% of component B and 0.5-10% of component C;
the component A is a compound L;
the component B comprises one or more propenyl compounds;
the component C comprises one or more of a photopolymerization initiator and a free radical polymerization initiator.
In order to further optimize the technical scheme, the allyl compound comprises one or more of acrylate-based monomers and acrylic-based monomers;
further, the acrylate-based monomer comprises one or more of a monoacrylate monomer, a diacrylate monomer and a triacrylate monomer;
further, the photopolymerization initiator comprises one or more of an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a carbazole compound, a diketone compound, a sulfonium boric acid compound, a diazonium salt compound, an imidazole compound and a non-imidazole compound;
further, the free radical polymerization initiator comprises one or more of peroxide compounds and bisazo compounds.
The embodiment of the invention also discloses a preparation method of the composition for packaging the organic light-emitting device, which comprises the following steps: and weighing the component A, the component B and the component C according to the proportion, mixing, uniformly mixing under a vacuum condition, and filtering to obtain the composition for packaging the organic light-emitting device.
The embodiment of the invention also discloses an organic light-emitting device packaging film, which is formed by laminating the same or independent organic layer and the inorganic layer for more than 1 time of coating, wherein the organic layer is the composition for packaging the organic light-emitting device.
The embodiment of the invention also discloses an organic light-emitting device which comprises the packaging film.
The embodiment of the invention also discloses an organic light-emitting device packaging method, which comprises the following steps: the composition for encapsulating the organic light-emitting device is directly coated on the organic light-emitting device, or the encapsulating film is directly attached on the organic light-emitting device.
Example 1
A compound L001 for packaging an organic light-emitting device comprises the following specific synthetic steps:
900g of 1, 1, 3, 3-tetramethyldisiloxane (L001-1), 1200g of diphenylsilanediol (L001-2) and 180g of p-toluenesulfonic acid were charged into a 20L reactor, stirred for 40 hours, then dissolved in 30L of toluene, and the liquid was washed 5 times with deionized water. Toluene was removed by rotary evaporation to give 1476g of compound 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L001-3) in 80% yield. 1476g of 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L001-3) and 990g of allylamine (L001-4) were dissolved in 15L of ethyl acetate and then charged into a reaction flask, 9g of a kataded catalyst solution of tetramethyldivinyldisiloxane was added to the reaction system, and then heated to 80 ℃ and stirred under reflux for 4 hours. After the temperature is reduced to normal temperature, the Pt catalyst is filtered and removed, the solvent and residual allylamine are removed by rotary evaporation through a reduced pressure distillation device, 2400g of a chemical formula L001-5, 2220g of isocyanate ethyl acrylate (L001-6) and 9L of toluene are obtained, and the compound L001 can be obtained after the reaction is completed after stirring for 4 hours at 50 ℃. MW: 727.05.
example 2
A composition for packaging an organic light-emitting device is prepared by the following steps:
50g of a monomer of the compound L001 was weighed, mixed with 930g of the component B and 20g of the component C, stirred at 50 ℃ for 80 hours under vacuum, and then filtered with a syringe filter to obtain a composition for encapsulating an organic light-emitting device.
Wherein, the component B comprises 558g of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester and 372g of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxyl) ethyl acrylate, and the component C is photoinitiator 2, 4, 6-trihydroxymethyl benzoyl diphenyl phosphine oxide.
In this example, the organic light emitting device-encapsulating composition was further coated with a spray at 100mW/cm2The coating is hardened by ultraviolet light after being irradiated for about 10 seconds under the condition of (1), and a coating with the thickness of 3 mu m of the coating thickness is formed; the coating was used as the organic layer 12 and silicon nitride as the inorganic layer 11, as inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11 (2)50nm) was formed on a PEN line (PEN line is a conductor having both a PE (protective conductor) line and a N (null) line), to obtain an organic light emitting device encapsulated with an encapsulation film, i.e., a thin film layer constituted in the form of an inorganic layer 11(250 nm)/an organic layer 12(3 μm)/an inorganic layer 11(250 nm).
Example 3
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the weighed mass of the monomer of compound L001 was replaced with 150g, the mass of 1, 12-dodecadienol 2-methyl-acrylate was replaced with 498g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 332 g.
Example 4
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 250g, the mass of 1, 12-dodecadienyl 2-methyl-acrylate was replaced with 438g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 292 g.
Example 5
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 350g, the mass of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester was replaced with 378g, and the mass of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 252 g.
Example 6
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 450g, the mass of 1, 12-dodecadienyl 2-methyl-acrylate was replaced with 318g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 212 g.
Example 7
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 550g, the mass of 1, 12-dodecadienyl 2-methyl-acrylate was replaced with 258g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 172 g.
Example 8
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 700g, the mass of 1, 12-dodecadienyl 2-methyl-acrylate was replaced with 168g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 112 g.
Comparative example 1
A composition for encapsulating an organic light-emitting device, which is different from embodiment 2 in that:
the mass of the monomer of the compound L001 weighed was replaced with 588g of 0g of 1, 12-dodecadienol 2-methyl-acrylate, and 392g of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate
Technical effects
In this example, the packaging films prepared in examples 2 to 8 and comparative example 1 were each subjected to water permeability measurement using a water permeability measuring apparatus (high precision water vapor transmission rate tester model AQUARAN2 of MOCON corporation, usa, membrankong corporation, usa). The measurement is carried out at 37.8 ℃ and 100% relative humidity for 24 hours, the water vapor transmission rate is measured, and the specific detection results are shown in Table 1.
TABLE 1 table of water vapor transmission rate test results
| Group of | Water vapor transmission rate (g/m)2.d) |
| Example 2 | 5.3×10-4 |
| Example 3 | 4.9×10-4 |
| Example 4 | 3.1×10-4 |
| Example 5 | 3.2×10-4 |
| Example 6 | 3.7×10-4 |
| Example 7 | 4.2×10-4 |
| Example 8 | 4.8×10-4 |
| Comparative example 1 | 8.0×10-3 |
As can be seen from table 1, the encapsulation film prepared using the compound L001 prepared in the example of the present invention can effectively block moisture, thereby improving the lifetime of the device.
Example 9
A compound L002 for packaging an organic light-emitting device comprises the following specific steps:
900g of 1, 1, 3, 3-tetramethyldisiloxane (L002-1), 1200g of diphenylsilanediol (L002-2) and 180g of p-toluenesulfonic acid were charged into a 15L three-necked bottle, stirred for 40 hours, then dissolved in 30L of toluene, and the liquid was washed 5 times with deionized water. Toluene was removed by rotary evaporation to give 1500g of compound 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L002-3) in 81% yield. 1500g of 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L002-3) and 1320g of allyl mercaptan (L002-4) were dissolved in 15L of ethyl acetate and then added to a reaction flask, 9g of a kataded catalyst solution of tetramethyldivinyldisiloxane was added to the reaction system, and then the mixture was heated to 80 ℃ and stirred under reflux for 4 hours. After the temperature is reduced to normal temperature, the Pt catalyst is filtered and removed, the solvent and the residual allyl mercaptan are removed by rotary evaporation through a reduced pressure distillation device, 2340g of a chemical formula L002-5 is obtained, and the obtained product is stirred with 2220g of isocyanate ethyl acrylate (L002-6) and 9L of toluene at 50 ℃ for 4 hours to react, so that a compound L002 is obtained. MW: 763.16.
the specific synthetic route is as follows:
example 10
A composition for packaging an organic light-emitting device is prepared by the following steps:
50g of the compound L002 monomer prepared by the method of example 9 was weighed, mixed with 930g of component B and 20g of component C, stirred at 50 ℃ for 80 hours under vacuum, and then filtered with a syringe filter to obtain a composition for encapsulating an organic light-emitting device.
Wherein, the component B comprises 558g of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester and 372g of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxyl) ethyl acrylate, and the component C is photoinitiator 2, 4, 6-trihydroxymethyl benzoyl diphenyl phosphine oxide.
In this example, the composition for encapsulating an organic light emitting device was further coated with a spray, irradiated for about 10 seconds under a condition of 100mW/cm2, and then hardened with ultraviolet light to form a coating having a coating thickness of 3 μm; an organic light emitting device in which a sealing film, that is, a thin film layer formed in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250nm), was encapsulated was obtained by forming a coating layer as organic layer 12 and silicon nitride as inorganic layer 11 on a PEN wire (PEN wire is a conductor having both a PE (protective earth) wire and a N (null) wire) in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250 nm).
Example 11
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the weighed mass of the monomer of compound L002 was replaced with 150g, the mass of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester was replaced with 498g, and the mass of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 332 g.
Example 12
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the mass of the monomer of the compound L002 weighed was replaced with 250g, and the mass of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester was replaced with 438g, and the mass of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 292 g.
Example 13
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the mass of the monomer of the compound L002 weighed was replaced with 378g of 350g of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester and 252g of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate.
Example 14
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the mass of the monomer of the compound L002 weighed was replaced with 450g, the mass of 1, 12-dodecadienol 2-methyl-acrylate, 318g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate, 212 g.
Example 15
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the mass of the monomer of the compound L002 weighed was replaced with 550g, the mass of 1, 12-dodecadienol 2-methyl-acrylate was replaced with 258g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 172 g.
Example 16
A composition for encapsulating an organic light-emitting device, which is different from embodiment 10 in that:
the weighed mass of the monomer of compound L002 was replaced with 700g, the mass of 1, 12-dodecadienol 2-methyl-2-propenoate was replaced with 168g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 112 g.
The technical effects are as follows:
in this example, the packaging films prepared in examples 10 to 16 were each subjected to water permeability measurement using a water permeability measuring instrument (high precision water vapor transmission rate tester model AQUARAN2 of MOCON corporation, usa). The measurement is carried out at 37.8 ℃ and 100% relative humidity for 24 hours, the water vapor transmission rate is measured, and the specific detection results are shown in Table 2.
TABLE 2 table of water vapor transmission rate test results
| Group of | Water vapor transmission rate (g/m)2·d) |
| Example 10 | 7.8×10-4 |
| Example 11 | 7.5×10-4 |
| Example 12 | 6.4×10-4 |
| Example 13 | 3.1×10-4 |
| Example 14 | 3.4×10-4 |
| Example 15 | 4.5×10-4 |
| Example 16 | 4.7×10-4 |
As can be seen from tables 1 and 2, the encapsulation films prepared using the compound L002 prepared in the examples of the present invention are effective in blocking moisture, exhibit low permeability of oxygen and moisture, and thus the encapsulation films extend the life span of devices, especially organic light emitting devices, as compared to comparative example 1, and the composition for encapsulation of organic light emitting devices and the organic/inorganic hybrid encapsulation films, which achieve higher flatness by enhancing the etching resistance of organic layers to plasma, and the display devices using the encapsulation films.
Example 17
A compound for packaging an organic light-emitting device comprises the following specific synthetic steps:
900g of 1, 1, 3, 3-tetramethyldisiloxane (L003-1), 1200g of diphenylsilanediol (L003-2) and 180g of p-toluenesulfonic acid were charged into a 15L three-necked flask, stirred for 40 hours, then dissolved in 30L of toluene and washed 5 times with deionized water in a separating funnel. Toluene was removed by rotary evaporation to give 1500g of compound 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L003-3) in 81% yield. 1500g of 1, 1, 5, 5-tetramethyl-3, 3-diphenyltrisiloxane (L003-3) and 1020g of allyl alcohol (L003-4) were dissolved in 15L of ethyl acetate and then charged into a reaction flask, 9g of a kataded catalyst solution of tetramethyldivinyldisiloxane was added to the reaction system, and then the mixture was heated to 80 ℃ and stirred under reflux for 4 hours. After the temperature is reduced to normal temperature, the Pt catalyst is filtered and removed, the solvent and residual allyl alcohol are removed by rotary evaporation through a reduced pressure distillation device, 2250g of chemical formula L003-5 is obtained, and the compound L002 can be obtained after the reaction of 2220g of isocyanate ethyl acrylate (L003-6) and 9L of toluene for 4 hours under stirring at 50 ℃. MW: 731.03.
the specific synthetic route is as follows:
example 18
A composition for packaging an organic light-emitting device is specifically prepared by the following steps:
50g of the compound L003 monomer prepared in example 17 was weighed, mixed with 930g of component B and 20g of component C, stirred at 50 ℃ for 80 hours under vacuum, and then filtered with a syringe filter to obtain a composition for encapsulating an organic light-emitting device.
Wherein, the component B comprises 558g of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester and 372g of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxyl) ethyl acrylate, and the component C is photoinitiator 2, 4, 6-trihydroxymethyl benzoyl diphenyl phosphine oxide.
In this example, the composition for encapsulating an organic light emitting device was further coated with a spray, irradiated for about 10 seconds under a condition of 100mW/cm2, and then hardened with ultraviolet light to form a coating having a coating thickness of 3 μm; an organic light emitting device in which a sealing film, that is, a thin film layer formed in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250nm), was encapsulated was obtained by forming a coating layer as organic layer 12 and silicon nitride as inorganic layer 11 on a PEN wire (PEN wire is a conductor having both a PE (protective earth) wire and a N (null) wire) in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250 nm).
Example 19
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the weighed mass of the monomer of compound L003 was replaced with 150g, and the mass of 1, 12-dodecadienol 2-methyl-2-propenoate was replaced with 498g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 332 g.
Example 20
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the weighed mass of the monomer of compound L003 was replaced with 250g, and the mass of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester was replaced with 438g, and the mass of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 292 g.
Example 21
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the weighed mass of the monomer of compound L003 was replaced with 350g, the mass of 2-methyl-2-propenoic acid-1, 12-dodecadienol ester was replaced with 378g, and the mass of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 252 g.
Example 22
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the weighed mass of the monomer of compound L003 was replaced with 450g, the mass of 1, 12-dodecadienol 2-methyl-2-propenoate was replaced with 318g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethacrylate was replaced with 212 g.
Example 23
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the mass of the monomer of the compound L003 weighed was replaced with 550g, the mass of 1, 12-dodecadienol 2-methyl-2-propenoate was replaced with 258g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethacrylate was replaced with 172 g.
Example 24
A composition for encapsulating an organic light-emitting device, which is different from embodiment 18 in that:
the weighed mass of the monomer of compound L003 was replaced with 700g, the mass of 1, 12-dodecadienol 2-methyl-2-propenoate was replaced with 168g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethacrylate was replaced with 112 g.
Technical effects
In this example, the packaging films prepared in examples 18 to 24 were each subjected to water permeability measurement using a water permeability measuring instrument (high precision water vapor transmission rate tester model AQUARAN2 of MOCON corporation, usa). The measurement was carried out at 37.8 ℃ and 100% relative humidity for 24 hours, and the water vapor transmission rate was measured, and the specific measurement results are shown in Table 3.
TABLE 3 table of water vapor transmission rate test results
| Group of | Water vapor transmission rate (g/m)2·d) |
| Example 18 | 8.5×10-4 |
| Example 19 | 8.2×10-4 |
| Example 20 | 7.5×10-4 |
| Example 21 | 4.6×10-4 |
| Example 22 | 3.1×10-4 |
| Example 23 | 4.5×10-4 |
| Example 24 | 4.9×10-4 |
As can be seen from tables 1 and 3, the encapsulation films prepared using the compound L003 prepared in the example of the present invention are effective in blocking water vapor, exhibit low permeability of oxygen and moisture, and thus are capable of encapsulating films to extend the life of devices, especially organic light emitting devices, and achieve higher flatness of the organic light emitting device encapsulating composition and organic/inorganic hybrid encapsulation films by enhancing the etching resistance of organic layers to plasma, as compared to comparative example 1, and display devices using the encapsulation films.
Example 25
A compound L004 for packaging an organic light-emitting device comprises the following specific synthetic steps:
900g of 1, 1, 3, 3-tetramethyldisiloxane (L004-1), 511g of dimethylsilanediol (L004-2) and 180g of p-toluenesulfonic acid were charged into a 20L reactor, stirred for 40 hours, then dissolved in 30L of toluene, and the separated liquid was washed 5 times with deionized water. Toluene was removed by rotary evaporation to give 1440g of compound 1, 1, 5, 5-tetramethyl-3, 3-dimethyltrisiloxane (L004-3) in 78% yield. 1440g of 1, 1, 5, 5-tetramethyl-3, 3-dimethyltrisiloxane (L004-3) and 980g of allylamine (L004-4) were dissolved in 15L of ethyl acetate and then charged into a reaction flask, 9g of a katadard catalyst solution of tetramethyldivinyldisiloxane was added to the reaction system, and then the mixture was heated to 80 ℃ and stirred under reflux for 4 hours. After the temperature is reduced to normal temperature, the Pt catalyst is filtered and removed, the solvent and residual allylamine are removed by rotary evaporation through a reduced pressure distillation device, 2340g of a chemical formula L004-5, 2180g of isocyanate ethyl acrylate (L004-6) and 9L of toluene are obtained, and the compound L004 is obtained after stirring for 4 hours at 50 ℃. MW: 602.91.
the specific synthetic route is as follows:
example 26
A composition for packaging an organic light-emitting device is prepared by the following steps:
50g of the above monomer of compound L004 was weighed, mixed with 930g of component B and 20g of component C, stirred at 50 ℃ for 80 hours under vacuum, and then filtered with a syringe filter to obtain a composition for encapsulating an organic light-emitting device.
Wherein, the component B comprises 558g of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester and 372g of acrylic acid 2- ([1, 1' -biphenyl ] -2-2-oxyl) ethyl acrylate, and the component C is photoinitiator 2, 4, 6-trihydroxymethyl benzoyl diphenyl phosphine oxide.
In this embodiment, the organic light emitter is further providedThe component packaging composition is coated by spray according to 100mW/cm2The coating is hardened by ultraviolet light after being irradiated for about 10 seconds under the condition of (1), and a coating with the thickness of 3 mu m of the coating thickness is formed; an organic light emitting device in which a sealing film, that is, a thin film layer formed in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250nm), was encapsulated was obtained by forming a coating layer as organic layer 12 and silicon nitride as inorganic layer 11 on a PEN wire (PEN wire is a conductor having both a PE (protective earth) wire and a N (null) wire) in the form of inorganic layer 11(250 nm)/organic layer 12(3 μm)/inorganic layer 11(250 nm).
Example 27
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 150g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 498g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-oxy) ethyl acrylate was replaced with 332 g.
Example 28
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 250g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 438g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 292 g.
Example 29
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 350g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 378g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 252 g.
Example 30
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 450g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 318g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 212 g.
Example 31
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 550g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 258g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 172 g.
Example 32
A composition for encapsulating an organic light-emitting device, which is different from example 26 in that:
the mass of the monomer of compound L004 was replaced with 700g, the mass of 1, 12-dodecadienyl 2-methyl-2-propenoate was replaced with 168g, and the mass of 2- ([1, 1' -biphenyl ] -2-2-yloxy) ethyl acrylate was replaced with 112 g.
Technical effects
In this example, the packaging films prepared in examples 26 to 32 were each subjected to water permeability measurement using a water permeability measuring apparatus (high precision water vapor transmission rate tester model AQUARAN2 of MOCON corporation, usa). The measurement is carried out at 37.8 ℃ and 100% relative humidity for 24 hours, the water vapor transmission rate is measured, and the specific detection results are shown in Table 1.
Table 4 table of water vapor transmission rate test results
| Group of | Water vapor transmission rate (g/m)2·d) |
| Example 26 | 5.8×10-4 |
| Example 27 | 5.2×10-4 |
| Example 28 | 4.6×10-4 |
| Example 29 | 4.2×10-4 |
| Example 30 | 4.5×10-4 |
| Example 31 | 4.4×10-4 |
| Example 32 | 4.9×10-4 |
As can be seen from tables 1 and 4, the encapsulation films prepared using the compound L004 prepared in examples of the present invention are effective in blocking water vapor, exhibit low permeability of oxygen and moisture, and thus can encapsulate films to extend the life of devices, especially organic light emitting devices, and achieve higher flatness of the organic light emitting device encapsulating composition and organic/inorganic hybrid encapsulation films by enhancing the etching resistance of organic layers to plasma, as compared to comparative example 1, and display devices using the encapsulation films.
In summary, embodiments of the present invention provide a photocurable or thermosetting composition for encapsulating an organic light emitting device, which can reduce the water vapor transmission rate after curing and encapsulating, and thus can lengthen the lifetime of a display device, and the encapsulation film of the present invention has a low shrinkage stress after curing, so that no offset can be generated. In addition, the organic light emitting device of the present invention enables various designs of organic light emitting display devices after curing and encapsulation, and most importantly, enables thinning.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A compound for use in encapsulation of an organic light emitting device, wherein the compound has a structural formula as follows:
wherein R1 to R6 are independently selected from hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted lactone groups, substituted or unsubstituted carboxyl groups, substituted or unsubstituted glycidyl ether groups, or hydroxyl groups;
Y1-Y4 are independently selected from alkyl;
z1 and Z2 are independently selected from hydrogen or methyl;
the X1 and X2 are independently selected from oxygen, amino, sulfur, group 1, group 2 or group 3; wherein the group 1, the group 2 and the group 3 are shown as follows:
2. the compound of claim 1, wherein R1-R6 are independently selected from substituted or unsubstituted C1～C10Alkyl, substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C6～C20Aryl, substituted or unsubstituted C2～C20Heteroaryl, substituted or unsubstituted C2～C10Alkenyl, substituted or unsubstituted C1～C10An alkoxy group;
Y1-Y4 are independently selected from C1-C10Alkyl group of (1).
3. The method of preparing a compound for organic light emitting device encapsulation according to claim 1 or 2, comprising the steps of:
1) mixing the compound D1, the compound D2 and p-toluenesulfonic acid, and reacting at 25 ℃ for 24 hours to obtain a compound D3;
wherein the mass ratio of the compound D1 to the compound D2 to the p-toluenesulfonic acid is as follows: (4-8) to 5; the using concentration of the p-toluenesulfonic acid is 99 percent;
2) dissolving a compound D3 and a compound D4 in ethyl acetate, adding a catalyst, and reacting at 80 ℃ for 4 hours to obtain a compound D5;
wherein the mass ratio of the compound D3 to the compound D4 to the ethyl acetate is as follows: (20-30) to 17: 250; the ethyl acetate is used at a concentration of 99.5%;
3) adding the compound D5 and the compound D6 into a toluene solution, and stirring and reacting at 50 ℃ for 6 hours to obtain a compound L;
wherein the mass ratio of the compound D5 to the compound D6 to the toluene solution is as follows: (30-50) to 9: 120; the concentration of the toluene solution is 99.5%;
the specific synthetic route is as follows:
4. the method of claim 3, wherein the catalyst in the step (2) is tetramethyldivinyldisiloxane, and the mass ratio of the compound D3, the compound D4 and the catalyst is (20-30) to 17: 0.15.
5. The composition for packaging the organic light-emitting device is characterized by comprising the following raw materials in percentage by mass: 5-70% of component A, 25-95% of component B and 0.5-10% of component C;
the component A is a compound as described in claim 1 or 2 or a compound prepared by the preparation method as described in claim 4;
the component B at least comprises one or more propenyl compounds;
the component C comprises one or a mixture of a plurality of photopolymerization initiators and free radical polymerization initiators.
6. The composition for encapsulating an organic light-emitting device according to claim 5, wherein the acryl-based compound comprises one or a mixture of acrylate-based monomers and acrylic-based monomers;
the acrylate-based monomer comprises one or a mixture of a plurality of acrylate monomers, diacrylate monomers and triacrylate monomers;
the photopolymerization initiator comprises one or a mixture of more of an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a carbazole compound, a diketone compound, a sulfonium boric acid compound, a diazonium salt compound, an imidazole compound and a non-imidazole compound;
the free radical polymerization initiator comprises one or a mixture of several of peroxide compounds and bisazo compounds.
7. The method for preparing the composition for encapsulating an organic light-emitting device according to claim 5 or 6, comprising the steps of:
and weighing the component A, the component B and the component C, mixing, uniformly mixing under a vacuum condition, and filtering to obtain the composition for packaging the organic light-emitting device.
8. An organic light emitting device encapsulation film, comprising inorganic layers, and an organic layer coated between the inorganic layers; wherein the organic layer is the composition for encapsulating an organic light-emitting device described in claim 5 or 6 or the composition for encapsulating an organic light-emitting device obtained by the production method described in claim 7.
9. An organic light-emitting device comprising the encapsulation film according to claim 8.
10. A method for encapsulating an organic light emitting device, comprising the steps of: the composition for encapsulating an organic light-emitting device according to claim 5 or 6 or the composition for encapsulating an organic light-emitting device obtained by the production method according to claim 7 is directly applied to an organic light-emitting device, or the encapsulating film according to claim 8 is directly attached to an organic light-emitting device.
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