TWI636090B - Sealant for organic electroluminescent display elements - Google Patents
Sealant for organic electroluminescent display elements Download PDFInfo
- Publication number
- TWI636090B TWI636090B TW104114037A TW104114037A TWI636090B TW I636090 B TWI636090 B TW I636090B TW 104114037 A TW104114037 A TW 104114037A TW 104114037 A TW104114037 A TW 104114037A TW I636090 B TWI636090 B TW I636090B
- Authority
- TW
- Taiwan
- Prior art keywords
- sealant
- compound represented
- organic electroluminescence
- weight
- display element
- Prior art date
Links
- 239000000565 sealant Substances 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000005401 electroluminescence Methods 0.000 claims abstract description 30
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 22
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 20
- -1 trifluoromethyl-substituted phenyl group Chemical group 0.000 claims description 72
- 150000004714 phosphonium salts Chemical class 0.000 claims description 7
- 239000012954 diazonium Substances 0.000 claims description 4
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 12
- 238000000576 coating method Methods 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 description 25
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 22
- 238000007789 sealing Methods 0.000 description 17
- 239000007822 coupling agent Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 238000010943 off-gassing Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical class CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- VBEKPAAWUSCJSK-UHFFFAOYSA-H triphenylsulfanium hexafluoride Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 VBEKPAAWUSCJSK-UHFFFAOYSA-H 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- HULVHBFBBOISKE-UHFFFAOYSA-N 1,2,3-triphenyl-9H-fluorene Chemical compound C1(=CC=CC=C1)C=1C(=C(C=2CC3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=CC=CC=C1 HULVHBFBBOISKE-UHFFFAOYSA-N 0.000 description 1
- QLGYTJLZFZUDFL-UHFFFAOYSA-N 1,3-bis[1-(1h-imidazol-2-yl)propyl]urea Chemical compound N=1C=CNC=1C(CC)NC(=O)NC(CC)C1=NC=CN1 QLGYTJLZFZUDFL-UHFFFAOYSA-N 0.000 description 1
- IZVCNSKRRSTZHL-UHFFFAOYSA-N 1-[4-[4-(2,3-diphenyl-9H-fluoren-1-yl)phenyl]sulfanylphenyl]-2,3-diphenyl-9H-fluorene Chemical compound C1(=CC=CC=C1)C=1C(=C(C=2CC3=CC=CC=C3C=2C=1)C1=CC=C(C=C1)SC1=CC=C(C=C1)C1=C(C(=CC=2C3=CC=CC=C3CC1=2)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 IZVCNSKRRSTZHL-UHFFFAOYSA-N 0.000 description 1
- ZPCMJYDANICQEY-UHFFFAOYSA-N 1-benzyl-2h-pyridine-2-carbonitrile Chemical compound N#CC1C=CC=CN1CC1=CC=CC=C1 ZPCMJYDANICQEY-UHFFFAOYSA-N 0.000 description 1
- CNOHWNUIQSHFEJ-UHFFFAOYSA-N 1-cyclopenta-2,4-dien-1-yl-2-propan-2-ylbenzene;iron Chemical compound [Fe].CC(C)C1=CC=CC=C1C1C=CC=C1 CNOHWNUIQSHFEJ-UHFFFAOYSA-N 0.000 description 1
- VDAIJDKQXDCJSI-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethylurea Chemical compound CC1=NC=CN1CCNC(N)=O VDAIJDKQXDCJSI-UHFFFAOYSA-N 0.000 description 1
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- DFYGYTNMHPUJBY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane-1-thiol Chemical compound SCCCC(C(OC)(OC)OC)CCCCCCCC DFYGYTNMHPUJBY-UHFFFAOYSA-N 0.000 description 1
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 1
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- FJARHPVZFRPXOF-UHFFFAOYSA-J [F-].[F-].[F-].[F-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [F-].[F-].[F-].[F-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 FJARHPVZFRPXOF-UHFFFAOYSA-J 0.000 description 1
- OFXNETALAMTDJC-UHFFFAOYSA-H [F-].[F-].[F-].[F-].[F-].[F-].C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 OFXNETALAMTDJC-UHFFFAOYSA-H 0.000 description 1
- RTNNOTFJIOSAMV-UHFFFAOYSA-H [F-].[F-].[F-].[F-].[F-].[F-].C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC RTNNOTFJIOSAMV-UHFFFAOYSA-H 0.000 description 1
- AFKGJUQOMNOUHY-UHFFFAOYSA-N [F-].[F-].[F-].[F-].[F-].[F-].COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC AFKGJUQOMNOUHY-UHFFFAOYSA-N 0.000 description 1
- YEKKSNHEOQOCJY-UHFFFAOYSA-H [F-].[F-].[F-].[F-].[F-].[F-].C[N+](C1=CC=CC=C1)(CC1=CC=CC=C1)C.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1 Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C[N+](C1=CC=CC=C1)(CC1=CC=CC=C1)C.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1.C[N+](C1=CC=CC=C1)(C)CC1=CC=CC=C1 YEKKSNHEOQOCJY-UHFFFAOYSA-H 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- HYVNJCOHGOONJK-UHFFFAOYSA-N dibenzyl-methyl-phenylazanium Chemical compound C=1C=CC=CC=1C[N+](C=1C=CC=CC=1)(C)CC1=CC=CC=C1 HYVNJCOHGOONJK-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940044652 phenolsulfonate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
-
- 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
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
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- C—CHEMISTRY; METALLURGY
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Abstract
本發明之目的在於提供一種可抑制釋氣之產生,保存穩定性及塗佈性優異之有機電激發光顯示元件用密封劑。 An object of the present invention is to provide a sealant for an organic electroluminescence display element which is capable of suppressing generation of outgas, and having excellent storage stability and coating properties.
本發明係一種有機電激發光顯示元件用密封劑,其含有陽離子聚合性化合物與陽離子聚合起始劑,並且上述陽離子聚合性化合物含有下述式(1-1)所示之化合物及/或下述式(1-2)所示之化合物,且使用E型黏度計於25℃、50rpm之條件下所測得之黏度為50~250mPa.s。 The present invention relates to a sealant for an organic electroluminescence display device, comprising a cationically polymerizable compound and a cationic polymerization initiator, and the cationically polymerizable compound contains a compound represented by the following formula (1-1) and/or The compound represented by the formula (1-2), and the viscosity measured by the E-type viscometer at 25 ° C, 50 rpm is 50 ~ 250 mPa. s.
Description
本發明係關於一種可抑制釋氣之產生,保存穩定性及塗佈性優異之有機電激發光顯示元件用密封劑。 The present invention relates to a sealant for an organic electroluminescence display element which is capable of suppressing generation of outgas, and having excellent storage stability and coating properties.
近年來,使用有有機電激發光(有機EL)顯示元件或有機薄膜太陽電池元件等有機薄膜元件之有機光元件之研究不斷進展。有機薄膜元件可藉由真空蒸鍍或溶液塗佈等而簡便地製作,因此生產性亦優異。 In recent years, research on organic optical elements using organic thin film elements such as organic electroluminescence (organic EL) display elements or organic thin film solar cell elements has progressed. The organic thin film device can be easily produced by vacuum evaporation or solution coating, and is therefore excellent in productivity.
有機EL顯示元件具有於相互對向之一對電極間夾持有有機發光材料層之薄膜構造體。藉由對該有機發光材料層自其中一個電極注入電子並且自另一電極注入電洞,使電子與電洞於有機發光材料層內結合而進行自發光。與需要背光裝置之液晶顯示元件等相比,具有視認性良好、可進一步實現薄型化,且可實現直流低電壓驅動等優點。 The organic EL display element has a film structure in which an organic light-emitting material layer is sandwiched between a pair of electrodes facing each other. Self-luminescence is performed by injecting electrons into one of the electrodes of the organic light-emitting material layer and injecting holes from the other electrode to bond the electrons and the holes in the organic light-emitting material layer. Compared with a liquid crystal display element or the like that requires a backlight device, it is excellent in visibility, can be further reduced in thickness, and can realize DC low-voltage driving.
且說,此種有機EL顯示元件存在若有機發光材料層或電極被暴露於外部大氣中則其發光特性急遽地劣化,而壽命縮短之問題。因此,為了提高有機EL顯示元件之穩定性及耐久性,於有機EL顯示元件必不可少的,是將有機發光材料層或電極與大氣中之水分或氧阻隔之密封技術。 In addition, such an organic EL display element has a problem that the light-emitting characteristics of the organic light-emitting material layer or the electrode are rapidly deteriorated when exposed to the outside atmosphere, and the lifetime is shortened. Therefore, in order to improve the stability and durability of the organic EL display element, it is indispensable for the organic EL display element to be a sealing technique for blocking the organic light-emitting material layer or the electrode from moisture or oxygen in the atmosphere.
專利文獻1中揭示有於上表面發光型有機EL顯示元件等 中,於有機EL顯示元件基板之間填滿光硬化性接著劑,並照射光而進行密封之方法。然而,此種習知之光硬化性接著劑存在於照射光時產生釋氣而使元件劣化、或保存穩定性或塗佈性差之問題。 Patent Document 1 discloses an upper surface light-emitting organic EL display element or the like. Among them, a method in which a photocurable adhesive is filled between the organic EL display element substrates and irradiated with light is used for sealing. However, such a conventional photocurable adhesive has a problem that upon the irradiation of light, outgas is generated to deteriorate the element, or the storage stability or the coatability is poor.
專利文獻1:日本特開2001-357973號公報 Patent Document 1: Japanese Laid-Open Patent Publication No. 2001-357973
本發明之目的在於提供一種可抑制釋氣之產生,保存穩定性及塗佈性優異之有機電激發光顯示元件用密封劑。 An object of the present invention is to provide a sealant for an organic electroluminescence display element which is capable of suppressing generation of outgas, and having excellent storage stability and coating properties.
本發明係一種有機電激發光顯示元件用密封劑,其含有陽離子聚合性化合物與陽離子聚合起始劑,並且上述陽離子聚合性化合物含有下述式(1-1)所示之化合物及/或下述式(1-2)所示之化合物,且使用E型黏度計於25℃、50rpm之條件下所測得之黏度為50~250mPa.s。 The present invention relates to a sealant for an organic electroluminescence display device comprising a cationically polymerizable compound and a cationic polymerization initiator, and the cationically polymerizable compound contains a compound represented by the following formula (1-1) and/or The compound represented by the formula (1-2), and the viscosity measured by the E-type viscometer at 25 ° C, 50 rpm is 50 ~ 250 mPa. s.
以下,對本發明進行詳細說明。 Hereinafter, the present invention will be described in detail.
本發明人等發現藉由使用特定之陽離子聚合性化合物,可獲得可抑制釋氣之產生,保存穩定性及塗佈性優異之有機電激發光顯示元件用密封劑,從而完成本發明。 The present inventors have found that a sealing agent for an organic electroluminescence display element which is excellent in storage stability and coating property can be obtained by using a specific cationically polymerizable compound, and the present invention can be completed.
本發明之有機電激發光顯示元件用密封劑含有陽離子聚合性化合物。 The sealing agent for an organic electroluminescence display device of the present invention contains a cationically polymerizable compound.
上述陽離子聚合性化合物含有上述式(1-1)所示之化合物及/或上述式(1-2)所示之化合物。以下,亦將上述式(1-1)所示之化合物與上述式(1-2)所示之化合物併稱為「本發明之環氧化合物」。藉由含有本發明之環氧化合物,本發明之有機電激發光顯示元件用密封劑成為可抑制釋氣之產生,保存穩定性及塗佈性優異者。 The cationically polymerizable compound contains the compound represented by the above formula (1-1) and/or the compound represented by the above formula (1-2). Hereinafter, the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2) are also referred to as "the epoxy compound of the present invention". By containing the epoxy compound of the present invention, the sealing agent for an organic electroluminescence display device of the present invention can suppress generation of outgassing, and is excellent in storage stability and coating properties.
上述陽離子聚合性化合物只要含有上述式(1-1)所示之化合物及上述式(1-2)所示之化合物中之至少一者即可,但就成為在抑制釋氣之效果、保存穩定性及塗佈性之所有方面更優異者之觀點而言,較佳含有上述式(1-1)所示之化合物及上述式(1-2)所示之化合物兩者。 The cationically polymerizable compound may contain at least one of the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2), but has an effect of suppressing outgassing and is stable in storage. From the viewpoint of the superiority of all aspects of the properties and the coating properties, it is preferred to contain both the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2).
於上述陽離子聚合性化合物含有上述式(1-1)所示之化合物及上述式(1-2)所示之化合物兩者之情形時,上述式(1-1)所示之化合物與上述式(1-2)所示之化合物之含有比例以重量比計較佳為上述式(1-1)所示之化合物:上述式(1-2)所示之化合物=9:1~1:4。藉由使上述式(1-1)所示之化合物與上述式(1-2)所示之化合物之含有比例為該範圍,可成為在抑制釋氣之效果、保存穩定性及塗佈性之所有方面更優異者。 When the cationically polymerizable compound contains both the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2), the compound represented by the above formula (1-1) and the above formula The content ratio of the compound represented by the formula (1-2) is preferably a compound represented by the above formula (1-1): a compound represented by the above formula (1-2) = 9:1 to 1:4. When the content ratio of the compound represented by the above formula (1-1) to the compound represented by the above formula (1-2) is within this range, the effect of suppressing outgassing, storage stability, and coatability can be achieved. All aspects are better.
作為上述式(1-1)所示之化合物中之市售者,可列舉 Celloxide 8000(大賽璐公司製造),作為上述式(1-2)所示之化合物中之市售者,可列舉Celloxide 2021P(大賽璐公司製造)。 As a commercial item among the compounds represented by the above formula (1-1), Celloxide 8000 (manufactured by Daicel Corporation), which is commercially available as a compound represented by the above formula (1-2), includes Celloxide 2021P (manufactured by Daicel Corporation).
本發明之有機電激發光顯示元件用密封劑亦可於不妨礙本 發明之目的之範圍內含有雙酚A型環氧樹脂或雙酚F型環氧樹脂等其他陽離子聚合性化合物作為上述陽離子聚合性化合物,但就塗佈性或抑制釋氣之觀點而言,較佳不含有其他陽離子聚合性化合物。 The sealing agent for organic electroluminescent display elements of the present invention can also prevent this In the range of the object of the invention, other cationically polymerizable compound such as a bisphenol A type epoxy resin or a bisphenol F type epoxy resin is contained as the above cationically polymerizable compound, but in terms of coatability or suppression of outgassing, It does not contain other cationically polymerizable compounds.
於含有上述其他陽離子聚合性化合物之情形時,陽離子聚合 性化合物整體100重量份中之本發明的環氧化合物之含量的較佳下限為60重量份。若本發明之環氧化合物之含量未達60重量份,則存在塗佈性變差或變得無法充分發揮出抑制釋氣之效果的情況。本發明之環氧化合物的含量之更佳下限為70重量份。 Cationic polymerization in the case of containing the above other cationically polymerizable compound A preferred lower limit of the content of the epoxy compound of the present invention in 100 parts by weight of the whole of the compound is 60 parts by weight. When the content of the epoxy compound of the present invention is less than 60 parts by weight, the coating property may be deteriorated or the effect of suppressing outgassing may not be sufficiently exhibited. A more preferred lower limit of the content of the epoxy compound of the present invention is 70 parts by weight.
本發明之有機電激發光顯示元件用密封劑含有陽離子聚合 起始劑。 The sealing agent for organic electroluminescent display elements of the present invention contains cationic polymerization Starting agent.
作為上述陽離子聚合起始劑,可列舉藉由加熱而產生質子酸或路易士酸之熱陽離子聚合起始劑,或藉由照射光而產生質子酸或路易士酸之光陽離子聚合起始劑,可為離子性酸產生型,亦可為非離子性酸產生型。 Examples of the cationic polymerization initiator include a thermal cationic polymerization initiator which generates a proton acid or a Lewis acid by heating, or a photocationic polymerization initiator which generates a proton acid or a Lewis acid by irradiation with light. It can be either an ionic acid or a nonionic acid.
其中,較佳含有熱陽離子聚合起始劑。 Among them, a thermal cationic polymerization initiator is preferably contained.
作為上述熱陽離子聚合起始劑,較佳為以BF4 -、PF6 -、SbF6 -、或(BX4)-(其中,X表示經至少2個以上之氟或三氟甲基取代之苯基)作為相對陰離子之鋶鹽、鏻鹽、四級銨鹽、重氮鹽或錪鹽,更佳為鋶鹽。 The above thermal cationic polymerization initiator is preferably BF 4 - , PF 6 - , SbF 6 - or (BX 4 ) - (wherein X represents at least 2 or more fluorine or trifluoromethyl substituted Phenyl) is a phosphonium salt, a phosphonium salt, a quaternary ammonium salt, a diazonium salt or a phosphonium salt as a relatively anion, more preferably a phosphonium salt.
作為上述鋶鹽,可列舉:三苯基鋶四氟化硼、三苯基鋶六氟化銻、三苯基鋶六氟化砷、三(4-甲氧基苯基)鋶六氟化砷、二苯基(4-苯硫 基苯基)鋶六氟化砷等。 Examples of the above sulfonium salt include triphenylsulfonium tetrafluoride, triphenylsulfonium hexafluoride, triphenylsulfonium hexafluoride, and tris(4-methoxyphenyl)phosphonium hexafluoride. Diphenyl (4-benzene sulfur) Phenyl phenyl) arsenic hexafluoride.
作為上述鏻鹽,可列舉:乙基三苯基鏻六氟化銻、四丁基鏻六氟化銻等。 Examples of the onium salt include ethyltriphenylphosphonium hexafluoride, tetrabutylphosphonium hexafluoride, and the like.
作為上述四級銨鹽,例如可列舉:二甲基苯基(4-甲氧基苄基)銨六氟磷酸鹽、二甲基苯基(4-甲氧基苄基)銨六氟銻酸鹽、二甲基苯基(4-甲氧基苄基)銨四(五氟苯基)硼酸鹽、二甲基苯基(4-甲基苄基)銨六氟磷酸鹽、二甲基苯基(4-甲基苄基)銨六氟銻酸鹽、二甲基苯基(4-甲基苄基)銨六氟四(五氟苯基)硼酸鹽、甲基苯基二苄基銨、甲基苯基二苄基銨六氟銻酸鹽、甲基苯基二苄基銨四(五氟苯基)硼酸鹽、苯基三苄基銨四(五氟苯基)硼酸鹽、二甲基苯基(3,4-二甲基苄基)銨四(五氟苯基)硼酸鹽、N,N-二甲基-N-苄基苯銨六氟化銻、N,N-二乙基-N-苄基苯銨四氟化硼、N,N-二甲基-N-苄基吡啶鎓六氟化銻(N,N-dimethyl-benzyl-N-pyridinium antimony hexafluoride)、N,N-二乙基-N-苄基吡啶鎓三氟甲磺酸鹽(N,N-diethyl-N-benzyl-pyridinium trifluoromethane sulfonate)等。 Examples of the above quaternary ammonium salt include dimethylphenyl (4-methoxybenzyl) ammonium hexafluorophosphate and dimethylphenyl (4-methoxybenzyl) ammonium hexafluoroantimonic acid. Salt, dimethylphenyl (4-methoxybenzyl) ammonium tetrakis(pentafluorophenyl)borate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorophosphate, dimethylbenzene (4-methylbenzyl)ammonium hexafluoroantimonate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorotetrakis(pentafluorophenyl)borate, methylphenyl dibenzylammonium , methylphenyldibenzylammonium hexafluoroantimonate, methylphenyldibenzylammonium tetrakis(pentafluorophenyl)borate, phenyltribenzylammonium tetrakis(pentafluorophenyl)borate, two Methylphenyl (3,4-dimethylbenzyl) ammonium tetrakis(pentafluorophenyl)borate, N,N-dimethyl-N-benzylphenylammonium hexafluoride, N,N-di N,N-dimethyl-benzyl-N-pyridinium antimony hexafluoride, N, N, N-methyl-benzyl-N-pyridinium antimony hexafluoride N-N-diethyl-N-benzyl-pyridinium trifluoromethane sulfonate or the like.
作為上述熱陽離子聚合起始劑中之市售者,例如可列舉:San -Aid SI-60、San-Aid SI-80、San-Aid SI-B3、San-Aid SI-B3A、San-Aid SI-B4(均為三新化學工業公司製造)、CXC1612、CXC1738、CXC1821(均為King Industries公司製造)等。 As a commercial one of the above-mentioned thermal cationic polymerization initiators, for example, San -Aid SI-60, San-Aid SI-80, San-Aid SI-B3, San-Aid SI-B3A, San-Aid SI-B4 (all manufactured by Sanxin Chemical Industry Co., Ltd.), CXC1612, CXC1738, CXC1821 ( All are manufactured by King Industries).
作為上述光陽離子聚合起始劑中之離子性光酸產生型者,例 如可列舉:陰離子部分含有BF4 -、PF6 -、SbF6 -、或(BX4)-(其中,X表示經至少2個以上之氟或三氟甲基取代之苯基)之芳香族鋶鹽、芳香族錪鹽、芳香族重氮鹽、芳香族銨鹽或(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵 鹽等。 As the ionic photoacid generation type in the photocationic polymerization initiator, for example, the anion moiety contains BF 4 - , PF 6 - , SbF 6 - , or (BX 4 ) - (wherein X represents at least An aromatic sulfonium salt, an aromatic sulfonium salt, an aromatic diazonium salt, an aromatic ammonium salt or a (2,4-cyclopentadien-1-yl group) of two or more fluorine or trifluoromethyl-substituted phenyl groups ((1-methylethyl)benzene)-iron salt and the like.
作為上述芳香族鋶鹽,例如可列舉:雙(4-(二苯基鋶基)苯 基)硫醚雙六氟磷酸鹽、雙(4-(二苯基鋶基)苯基)硫醚雙六氟銻酸鹽、雙(4-(二苯基鋶基)苯基)硫醚雙四氟硼酸鹽、雙(4-(二苯基鋶基)苯基)硫醚四(五氟苯基)硼酸鹽、二苯基-4-(苯硫基)苯基鋶六氟磷酸鹽、二苯基-4-(苯硫基)苯基鋶六氟銻酸鹽、二苯基-4-(苯硫基)苯基鋶四氟硼酸鹽、二苯基-4-(苯硫基)苯基鋶四(五氟苯基)硼酸鹽、三苯基鋶六氟磷酸鹽、三苯基鋶六氟銻酸鹽、三苯基鋶四氟硼酸鹽、三苯基鋶四(五氟苯基)硼酸鹽、雙(4-(二(4-(2-羥基乙氧基))苯基鋶基)苯基)硫醚雙六氟磷酸鹽、雙(4-(二(4-(2-羥基乙氧基))苯基鋶基)苯基)硫醚雙六氟銻酸鹽、雙(4-(二(4-(2-羥基乙氧基))苯基鋶基)苯基)硫醚雙四氟硼酸鹽、雙(4-(二(4-(2-羥基乙氧基))苯基鋶基)苯基)硫醚四(五氟苯基)硼酸鹽等。 Examples of the above aromatic onium salt include bis(4-(diphenylfluorenyl)benzene. Thiophene bishexafluorophosphate, bis(4-(diphenylfluorenyl)phenyl) sulfide dihexafluoroantimonate, bis(4-(diphenylfluorenyl)phenyl) sulfide Tetrafluoroborate, bis(4-(diphenylfluorenyl)phenyl) sulfide tetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylphosphonium hexafluorophosphate, Diphenyl-4-(phenylthio)phenylphosphonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylphosphonium tetrafluoroborate, diphenyl-4-(phenylthio) Phenylphosphonium tetrakis(pentafluorophenyl)borate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium tetrakis(pentafluorobenzene) Borate, bis(4-(bis(4-(2-hydroxyethoxy))phenyl) phenyl) thioether bis hexafluorophosphate, bis (4-(di(4-(2) -hydroxyethoxy))phenylindenyl)phenyl)thiophene bishexafluoroantimonate, bis(4-(bis(4-(2-hydroxyethoxy))phenyl)phenyl)phenyl) Thioether bistetrafluoroborate, bis(4-(di(4-(2-hydroxyethoxy))phenyl) phenyl) thio) tetrakis(pentafluorophenyl)borate, and the like.
作為上述芳香族錪鹽,例如可列舉:二苯基錪六氟磷酸鹽、 二苯基錪六氟銻酸鹽、二苯基錪四氟硼酸鹽、二苯基錪四(五氟苯基)硼酸鹽、雙(十二烷基苯基)錪六氟磷酸鹽、雙(十二烷基苯基)錪六氟銻酸鹽、雙(十二烷基苯基)錪四氟硼酸鹽、雙(十二烷基苯基)錪四(五氟苯基)硼酸鹽、4-甲基苯基-4-(1-甲基乙基)苯基錪六氟磷酸鹽、4-甲基苯基-4-(1-甲基乙基)苯基錪六氟銻酸鹽、4-甲基苯基-4-(1-甲基乙基)苯基錪四氟硼酸鹽、4-甲基苯基-4-(1-甲基乙基)苯基錪四(五氟苯基)硼酸鹽等。 Examples of the aromatic onium salt include diphenylphosphonium hexafluorophosphate. Diphenylphosphonium hexafluoroantimonate, diphenylphosphonium tetrafluoroborate, diphenylphosphonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)phosphonium hexafluorophosphate, double Dodecylphenyl)phosphonium hexafluoroantimonate, bis(dodecylphenyl)phosphonium tetrafluoroborate, bis(dodecylphenyl)phosphonium tetrakis(pentafluorophenyl)borate, 4 -methylphenyl-4-(1-methylethyl)phenylphosphonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenylphosphonium hexafluoroantimonate, 4-methylphenyl-4-(1-methylethyl)phenylhydrazine tetrafluoroborate, 4-methylphenyl-4-(1-methylethyl)phenylphosphonium tetrakis(pentafluorobenzene) Base) borate and the like.
作為上述芳香族重氮鹽,例如可列舉:苯基重氮六氟磷酸 鹽、苯基重氮六氟銻酸鹽、苯基重氮四氟硼酸鹽、苯基重氮四(五氟苯基)硼酸鹽等。 Examples of the above aromatic diazonium salt include phenyldiazonium hexafluorophosphate. Salt, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, phenyldiazonium tetrakis(pentafluorophenyl)borate, and the like.
作為上述芳香族銨鹽,例如可列舉:1-苄基-2-氰基吡啶 鎓六氟磷酸鹽(1-benzyl-2-cyano-pyridinium hexafluorophosphate)、1-苄基-2-氰基吡啶鎓六氟銻酸鹽(1-benzyl-2-cyano-pyridinium hexafluoroantimonate)、1-苄基-2-氰基吡啶鎓四氟硼酸鹽(1-benzyl-2-cyano-pyridinium tetrafluoroborate)、1-苄基-2-氰基吡啶鎓四(五氟苯基)硼酸鹽(1-benzyl-2-cyano-pyridinium tetrakis(pentafluorophenyl)borate)、1-(萘基甲基)-2-氰基吡啶鎓六氟磷酸鹽(1-(naphthylmethyl)-2-cyano-pyridinium hexafluorophosphate)、1-(萘基甲基)-2-氰基吡啶鎓六氟銻酸鹽(1-(naphthylmethyl)-2-cyano-pyridinium hexafluoroantimonate)、1-(萘基甲基)-2-氰基吡啶鎓四氟硼酸鹽(1-(naphthylmethyl)2-cyano-pyridinium tetrafluoroborate)、1-(萘基甲基)-2-氰基吡啶鎓四(五氟苯基)硼酸鹽(1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate)等。 Examples of the above aromatic ammonium salt include 1-benzyl-2-cyanopyridine. 1-benzyl-2-cyano-pyridinium hexafluorophosphate, 1-benzyl-2-cyano-pyridinium hexafluoroantimonate, 1-benzyl 1-benzyl-2-cyano-pyridinium tetrafluoroborate, 1-benzyl-2-cyanopyridinium tetrakis(pentafluorophenyl)borate (1-benzyl-) 2-cyano-pyridinium tetrakis(pentafluorophenyl)borate), 1-(naphthylmethyl)-2-cyano-pyridinium hexafluorophosphate, 1-(naphthalene) 1-(naphthylmethyl)-2-cyano-pyridinium hexafluoroantimonate, 1-(naphthylmethyl)-2-cyanopyridinium tetrafluoroborate (1-(naphthylmethyl)2-cyano-pyridinium tetrafluoroborate), 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate (1-(naphthylmethyl)-2-cyanopyridinium tetrakis ( Pentafluorophenyl)borate).
作為上述(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵 鹽,例如可列舉:(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵(II)六氟磷酸鹽、(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵(II)六氟銻酸鹽、(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵(II)四氟硼酸鹽、(2,4-環戊二烯-1-基)((1-甲基乙基)苯)-鐵(II)四(五氟苯基)硼酸鹽等。 As the above (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-iron The salt may, for example, be (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-iron (II) hexafluorophosphate or (2,4-cyclopentadiene). -1-yl)((1-methylethyl)benzene)-iron(II) hexafluoroantimonate, (2,4-cyclopentadien-1-yl)((1-methylethyl) Benzene)-iron(II)tetrafluoroborate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-iron(II)tetrakis(pentafluorophenyl)borate Salt and so on.
作為上述光陽離子聚合起始劑中之非離子性光酸產生型 者,例如可列舉:硝基苄基酯、磺酸衍生物、磷酸酯、苯酚磺酸酯、重氮萘醌、N-羥基醯亞胺磺酸酯等。 As a nonionic photoacid generating type in the above photocationic polymerization initiator Examples thereof include a nitrobenzyl ester, a sulfonic acid derivative, a phosphate ester, a phenolsulfonate, a diazonaphthoquinone, and an N-hydroxy sulfenium sulfonate.
作為上述光陽離子聚合起始劑中之市售者,例如可列舉: DTS-200(Midori化學公司製造)、UVI6990、UVI6974(均為Union Carbide公司製造)、SP-150、SP-170(均為艾迪科公司製造)、FC-508、FC-512(均為3M公司製造)、IRGACURE290(BASF公司製造)、PI2074(Rhodia公司製造)等。 As a commercially available one of the above photocationic polymerization initiators, for example, DTS-200 (manufactured by Midori Chemical Co., Ltd.), UVI6990, UVI6974 (all manufactured by Union Carbide), SP-150, SP-170 (all manufactured by Aidike), FC-508, FC-512 (both 3M) Manufactured by the company, IRGACURE 290 (manufactured by BASF Corporation), PI2074 (manufactured by Rhodia Co., Ltd.), etc.
關於上述熱陽離子聚合起始劑與上述光陽離子聚合起始劑 兩者所記載者,可用作上述熱陽離子聚合起始劑,亦可用作上述光陽離子聚合起始劑。 Regarding the above thermal cationic polymerization initiator and the above photocationic polymerization initiator Both of them can be used as the above-mentioned thermal cationic polymerization initiator, and can also be used as the above photocationic polymerization initiator.
關於上述陽離子聚合起始劑之含量,相對於上述陽離子聚合 性化合物100重量份,較佳下限為0.01重量份,較佳上限為10重量份。若上述陽離子聚合起始劑之含量未達0.01重量份,則存在無法對所獲得之有機電激發光顯示元件用密封劑賦予充分之硬化性之情況。若上述陽離子聚合起始劑之含量超過10重量份,則存在所獲得之有機電激發光顯示元件用密封劑之保存穩定性變得不充分,或所獲得之有機電激發光顯示元件用密封劑之硬化物的耐濕性變差之情況。上述陽離子聚合起始劑之含量之更佳下限為0.05重量份,更佳上限為5重量份。 Regarding the content of the above cationic polymerization initiator, relative to the above cationic polymerization The lower limit of the compound is 100 parts by weight, preferably 0.01 part by weight, and the upper limit is preferably 10 parts by weight. When the content of the cationic polymerization initiator is less than 0.01 parts by weight, sufficient curability may not be imparted to the obtained sealing agent for an organic electroluminescence display device. When the content of the cationic polymerization initiator is more than 10 parts by weight, the storage stability of the obtained sealant for an organic electroluminescence display device may be insufficient, or the obtained sealant for an organic electroluminescent display element may be obtained. The moisture resistance of the cured product is deteriorated. A more preferred lower limit of the content of the above cationic polymerization initiator is 0.05 parts by weight, and a more preferred upper limit is 5 parts by weight.
本發明之有機電激發光顯示元件用密封劑較佳含有穩定 劑。藉由含有上述穩定劑,本發明之有機電激發光顯示元件用密封劑成為保存穩定性更優異者。 The sealing agent for organic electroluminescent display elements of the present invention preferably contains a stable Agent. The sealant for an organic electroluminescence display device of the present invention is more excellent in storage stability by containing the above stabilizer.
作為上述穩定劑,例如可列舉苄胺等胺系化合物或胺基苯酚 型環氧樹脂等。 Examples of the stabilizer include an amine compound such as benzylamine or an aminophenol. Type epoxy resin, etc.
關於上述穩定劑之含量,相對於上述陽離子聚合性化合物 100重量份,較佳下限為0.001重量份,較佳上限為2重量份。若上述穩定 劑之含量未達0.001重量份,則存在無法充分發揮出使所獲得之有機電激發光顯示元件用密封劑的保存穩定性提高之效果的情況。若上述穩定劑之含量超過2重量份,則存在妨礙利用陽離子所進行之硬化之情況。上述穩定劑之含量的更佳下限為0.05重量份,更佳上限為1重量份。 Regarding the content of the above stabilizer, relative to the above cationically polymerizable compound A preferred lower limit is 100 parts by weight, preferably 0.001 part by weight, and a preferred upper limit is 2 parts by weight. If the above is stable When the content of the agent is less than 0.001 part by weight, the effect of improving the storage stability of the obtained sealant for an organic electroluminescence display device may not be sufficiently exhibited. When the content of the above stabilizer is more than 2 parts by weight, there is a case where the curing by the cation is hindered. A more preferred lower limit of the content of the above stabilizer is 0.05 parts by weight, and a still more preferred upper limit is 1 part by weight.
本發明之有機電激發光顯示元件用密封劑亦可含有矽烷偶 合劑。上述矽烷偶合劑具有使本發明之有機電激發光顯示元件用密封劑與基板等之接著性提高的作用。 The sealing agent for an organic electroluminescence display element of the present invention may also contain a decane couple mixture. The decane coupling agent has an effect of improving the adhesion between the sealing agent for an organic electroluminescence display device of the present invention and a substrate.
作為上述矽烷偶合劑,例如可列舉:3-胺基丙基三甲氧基 矽烷、3-巰基丙基三甲氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-異氰酸酯基丙基三甲氧基矽烷等。該等矽烷偶合劑可單獨使用,亦可併用兩種以上。 As the above decane coupling agent, for example, 3-aminopropyltrimethoxy group can be mentioned. Decane, 3-mercaptopropyltrimethoxydecane, 3-glycidoxypropyltrimethoxydecane, 3-isocyanatepropyltrimethoxydecane, and the like. These decane coupling agents may be used singly or in combination of two or more.
關於上述矽烷偶合劑之含量,相對於上述陽離子聚合性化合 物100重量份,較佳下限為0.1重量份,較佳上限為10重量份。若上述矽烷偶合劑之含量未達0.1重量份,則存在無法充分發揮出使所獲得之有機電激發光顯示元件用密封劑的接著性提高之效果。若上述矽烷偶合劑之含量超過10重量份,則存在剩餘之矽烷偶合劑滲出之情況。上述矽烷偶合劑之含量之更佳下限為0.5重量份,更佳上限為5重量份。 Regarding the content of the above decane coupling agent, the above-mentioned cationic polymerization compound The content is preferably 100 parts by weight, preferably 0.1 part by weight, and preferably 10 parts by weight. When the content of the above-mentioned decane coupling agent is less than 0.1 part by weight, the effect of improving the adhesion of the obtained sealing agent for an organic electroluminescence display element can not be sufficiently exhibited. When the content of the above decane coupling agent exceeds 10 parts by weight, the remaining decane coupling agent may bleed out. A more preferred lower limit of the content of the above decane coupling agent is 0.5 part by weight, and a more preferred upper limit is 5 parts by weight.
本發明之有機電激發光顯示元件用密封劑亦可於不妨礙本 發明之目的之範圍內含有熱硬化劑。 The sealing agent for organic electroluminescent display elements of the present invention can also prevent this A heat hardener is included in the scope of the object of the invention.
作為上述熱硬化劑,例如可列舉:醯肼化合物、咪唑衍生物、酸酐、雙氰胺、胍衍生物、改質脂肪族多胺、各種胺與環氧樹脂之加成產物等。 Examples of the above-mentioned thermosetting agent include an anthracene compound, an imidazole derivative, an acid anhydride, dicyandiamide, an anthracene derivative, a modified aliphatic polyamine, and an addition product of various amines and an epoxy resin.
作為上述醯肼化合物,例如可列舉:1,3-雙[肼基碳乙基-5-異丙基 乙內醯脲]等。 As the above hydrazine compound, for example, 1,3-bis[mercaptocarboethyl-5-isopropyl group can be mentioned. B-urea urea] and so on.
作為上述咪唑衍生物,例如可列舉:1-氰乙基-2-苯基咪唑、N-[2-(2-甲基-1-咪唑基)乙基]脲、2,4-二胺基-6-[2'-甲基咪唑基-(1')]-乙基-對稱三、N,N'-雙(2-甲基-1-咪唑基乙基)脲、N,N'-(2-甲基-1-咪唑基乙基)-己二醯胺、2-苯基-4-甲基-5-羥基甲基咪唑、2-苯基-4,5-二羥基甲基咪唑等。 Examples of the above imidazole derivative include 1-cyanoethyl-2-phenylimidazole, N-[2-(2-methyl-1-imidazolyl)ethyl]urea, and 2,4-diamino group. -6-[2'-methylimidazolyl-(1')]-ethyl-symmetric three , N,N'-bis(2-methyl-1-imidazolylethyl)urea, N,N'-(2-methyl-1-imidazolylethyl)-hexanediamine, 2-phenyl 4-methyl-5-hydroxymethylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and the like.
作為上述酸酐,例如可列舉:四氫鄰苯二甲酸酐、乙二醇雙(偏苯三酸酐酯)(ethylene glycol bisanhydrotrimellitate)等。 Examples of the acid anhydride include tetrahydrophthalic anhydride and ethylene glycol bisanhydrotrimellitate.
該等熱硬化劑可單獨使用,亦可併用兩種以上。 These thermosetting agents may be used singly or in combination of two or more.
本發明之有機電激發光顯示元件用密封劑亦可於不妨礙本發明之目的之範圍內含有表面改質劑。藉由含有上述表面改質劑,可提高本發明之有機電激發光顯示元件用密封劑之塗膜的平坦性。 The sealant for an organic electroluminescence display element of the present invention may contain a surface modifier in a range that does not impair the object of the present invention. By including the surface modifying agent, the flatness of the coating film of the sealing agent for an organic electroluminescence display device of the present invention can be improved.
作為上述表面改質劑,例如可列舉界面活性劑或調平劑等。 Examples of the surface modifier include a surfactant, a leveling agent, and the like.
作為上述界面活性劑或上述調平劑,例如可列舉聚矽氧系、丙烯酸系、氟系等之界面活性劑或調平劑。 The surfactant or the leveling agent may, for example, be a surfactant such as a polyfluorene-based, acrylic or fluorine-based surfactant or a leveling agent.
作為上述界面活性劑或上述調平劑中之市售者,例如可列舉:BYK-302、BYK-331(均為BYK-Chemie Japan公司製造)、UVX-272(楠本化成公司製造)、Surflon S-611(AGC Seimi Chemical公司製造)等。 For example, BYK-302, BYK-331 (all manufactured by BYK-Chemie Japan Co., Ltd.), UVX-272 (manufactured by Nanmoto Chemical Co., Ltd.), and Surflon S can be cited as the above-mentioned surfactant or the above-mentioned leveling agent. -611 (manufactured by AGC Seimi Chemical Co., Ltd.) and the like.
本發明之有機電激發光顯示元件用密封劑亦可於不妨礙本發明之目的之範圍內,為了提高元件電極之耐久性而含有化合物或離子交換樹脂,該化合物或離子交換樹脂會與於有機電激發光顯示元件用密封劑中所產生之酸進行反應。 The sealing agent for an organic electroluminescence display element of the present invention may contain a compound or an ion exchange resin in order to improve the durability of the element electrode, without impairing the object of the present invention, and the compound or ion exchange resin may be present. The electromechanical excitation light display element is reacted with an acid generated in the sealant.
作為與上述所產生之酸進行反應之化合物,可列舉與酸中和 之物質,例如鹼金屬之碳酸鹽或碳酸氫鹽,或者鹼土金屬之碳酸鹽或碳酸氫鹽等。具體而言,例如可使用:碳酸鈣、碳酸氫鈣、碳酸鈉、碳酸氫鈉等。 As a compound which reacts with the acid produced above, it can mention that it neutralizes with an acid. A substance such as an alkali metal carbonate or hydrogencarbonate, or an alkaline earth metal carbonate or hydrogencarbonate. Specifically, for example, calcium carbonate, calcium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate or the like can be used.
作為上述離子交換樹脂,可使用陽離子交換型、陰離子交換 型、兩性離子交換型中之任一類型,尤其適宜為可吸附氯化物離子之陽離子交換型或兩性離子交換型。 As the above ion exchange resin, cation exchange type and anion exchange can be used. Any of the types and zwitterionic exchange types is particularly preferably a cation exchange type or a zwitterionic exchange type which can adsorb chloride ions.
又,本發明之有機電激發光顯示元件用密封劑亦可於不妨礙 本發明之目的之範圍內,視需要含有硬化延遲劑、補強劑、軟化劑、塑化劑、黏度調整劑、紫外線吸收劑、抗氧化劑等公知之各種添加劑。 Moreover, the sealant for an organic electroluminescence display element of the present invention can also be prevented Within the scope of the object of the present invention, various known additives such as a hardening retarder, a reinforcing agent, a softening agent, a plasticizer, a viscosity adjusting agent, an ultraviolet absorber, and an antioxidant are contained as needed.
作為製造本發明之有機電激發光顯示元件用密封劑之方 法,例如可列舉如下方法等:使用勻相分散機、均質攪拌機、萬能攪拌機、行星式攪拌機、捏合機、三輥研磨機等混合機,將陽離子聚合性化合物、陽離子聚合起始劑及視需要添加之矽烷偶合劑等添加劑進行混合。 As a sealing agent for producing the organic electroluminescent display element of the present invention For example, a method such as a homogeneous phase disperser, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mill may be used, and a cationically polymerizable compound, a cationic polymerization initiator, and optionally Additives such as a decane coupling agent are added and mixed.
本發明之有機電激發光顯示元件用密封劑之使用E型黏度 計並於25℃、50rpm之條件下所測得之整體的黏度之下限為50mPa.s,上限為250mPa.s。若上述黏度未達50mPa.s,則所獲得之有機電激發光顯示元件用密封劑於塗佈性方面變差,或發生組成不均而硬化物於透明性方面變差。若上述黏度超過250mPa.s,則所獲得之有機電激發光顯示元件用密封劑於塗佈性方面變差。上述黏度較佳為70mPa.s以上,未達100mPa.s。 E-type viscosity of the sealant for organic electroluminescent display elements of the present invention The lower limit of the overall viscosity measured at 25 ° C, 50 rpm is 50 mPa. s, the upper limit is 250mPa. s. If the above viscosity is less than 50mPa. s, the sealant for an organic electroluminescence display element obtained is deteriorated in coatability, or composition unevenness occurs, and the cured product is deteriorated in transparency. If the above viscosity exceeds 250mPa. s, the obtained sealant for an organic electroluminescence display element deteriorates in coatability. The above viscosity is preferably 70 mPa. Above s, less than 100mPa. s.
根據本發明,可提供一種可抑制釋氣之產生,保存穩定性及 塗佈性優異之有機電激發光顯示元件用密封劑。 According to the present invention, it is possible to provide a method for suppressing the generation of outgas, storage stability and A sealant for an organic electroluminescence display element excellent in coatability.
以下,揭示實施例而更詳細地對本發明進行說明,但本發明並不僅限定於該等實施例。 Hereinafter, the present invention will be described in more detail by explaining the examples, but the present invention is not limited to the examples.
將作為陽離子聚合性化合物之上述式(1-1)所示之化合物(大賽璐公司製造,「Celloxide 8000」)50重量份及上述式(1-2)所示之化合物(大賽璐公司製造,「Celloxide 2021P」)50重量份,以及作為熱陽離子聚合起始劑之銻系起始劑(King Industries公司製造,「CXC1612」)0.5重量份,使用攪拌混合機(Thinky公司製造,「AR-250」),以攪拌速度3000rpm均勻地進行攪拌混合,而製作有機電激發光顯示元件用密封劑。 50 parts by weight of a compound represented by the above formula (1-1) ("Celloxide 8000" manufactured by Daicel Co., Ltd.) and a compound represented by the above formula (1-2) (manufactured by Daicel Corporation), which is a cationically polymerizable compound, 50 parts by weight of "Celloxide 2021P" and 0.5 parts by weight of an oxime-based initiator ("CXC1612" manufactured by King Industries Co., Ltd.) as a thermal cationic polymerization initiator, using a stirring mixer (manufactured by Thinky, "AR-250" The mixture was uniformly stirred and mixed at a stirring speed of 3000 rpm to prepare a sealant for an organic electroluminescence display element.
將表1、2中記載之各材料,依照表1中記載之調配比,與實施例1同樣地進行攪拌混合,而製作實施例2~10、比較例1~9之有機電激發光顯示元件用密封劑。 Each of the materials described in Tables 1 and 2 was stirred and mixed in the same manner as in Example 1 in accordance with the blending ratios shown in Table 1, and the organic electroluminescent display elements of Examples 2 to 10 and Comparative Examples 1 to 9 were produced. Use a sealant.
針對實施例及比較例中所獲得之各有機電激發光顯示元件用密封劑進行以下之評價。將結果示於表1、2。 The following evaluations were performed for each of the sealants for an organic electroluminescence display element obtained in the examples and the comparative examples. The results are shown in Tables 1 and 2.
針對實施例及比較例中所獲得之各有機電激發光顯示元件用密封劑,使用E型黏度計(東機產業公司製造,「VISCOMETER TV-22」),測量25℃、50rpm之條件下之黏度。 For each of the sealants for organic electroluminescent display elements obtained in the examples and the comparative examples, an E-type viscometer ("VISCOMETER TV-22" manufactured by Toki Sangyo Co., Ltd.) was used, and the conditions were measured at 25 ° C and 50 rpm. Viscosity.
使用移液管將0.1mL之實施例及比較例中所獲得的各有機電激發光顯示元件用密封劑塗佈至玻璃基板上,1分鐘後測量擴展所得之直徑。以將直徑為15mm以上之情形設為「◎」,將12mm以上,未達15mm之情形設為「○」,將10mm以上,未達12mm之情形設為「△」,將未達10mm之情形設為「×」,對塗佈性進行評價。 0.1 mL of each of the organic electroluminescent display elements obtained in the examples and the comparative examples was applied onto a glass substrate using a pipette, and the diameter obtained by the expansion was measured after 1 minute. When the diameter is 15 mm or more, it is set to "◎", and if it is 12 mm or more, if it is less than 15 mm, it is set to "○", and if it is 10 mm or more, if it is less than 12 mm, it is set to "△", and it is less than 10 mm. The coating property was evaluated by setting it to "x".
針對實施例及比較例中所獲得之各有機電激發光顯示元件用密封劑,測量剛製造後之初始黏度及於25℃下保管1週時之黏度,將(於25℃下保管1週後之黏度)/(初始黏度)設為黏度變化率,將黏度變化率未達150%者設為「◎」,將150%以上,未達200%者設為「○」,將200%以上,未達400%者設為「△」,將超過400%者設為「×」,對保存穩定性進行評價。 For each of the sealants for organic electroluminescence display elements obtained in the examples and the comparative examples, the initial viscosity immediately after the production and the viscosity at 25 ° C for one week were measured, and the samples were stored at 25 ° C for one week. The viscosity)/(initial viscosity) is set as the viscosity change rate, and the viscosity change rate is less than 150%, and is set to "◎", and 150% or more, and less than 200% is set to "○", which is 200% or more. When the number is less than 400%, it is set to "△", and when it is more than 400%, it is set to "X", and the storage stability is evaluated.
再者,有機電激發光顯示元件用密封劑之黏度係使用E型黏度計(東機產業公司製造,「VISCOMETER TV-22」),於25℃、50rpm之條件下進行測量。 In addition, the viscosity of the sealant for the organic electroluminescence display element was measured at 25 ° C and 50 rpm using an E-type viscometer ("VISCOMETER TV-22" manufactured by Toki Sangyo Co., Ltd.).
計量300mg之實施例及比較例中所獲得之各有機電激發光顯示元件用密封劑,並封入小玻璃瓶中之後,針對實施例1~7及比較例1~9中所獲得 之各有機電激發光顯示元件用密封劑,藉由在100℃下進行加熱30分鐘而使之硬化,針對實施例8~10中所獲得之各有機電激發光顯示元件用密封劑,使用紫外線照射裝置(Oak公司製造,「JL-4300-3S」)以1500mJ/cm2照射紫外線,其後於80℃下加熱30分鐘而使之硬化。進而,將該小玻璃瓶於85℃之恆溫烘箱中加熱100小時,並使用氣相層析質譜分析儀(日本電子公司製造,「JMS-Q1050」)對小玻璃瓶中之氣化成分進行測量。 Each of the organic electric powers obtained in Examples 1 to 7 and Comparative Examples 1 to 9 was measured after 300 mg of each of the sealants for organic electroluminescent display elements obtained in the examples and the comparative examples was sealed in a vial. The sealing agent for the light-emitting display element was cured by heating at 100 ° C for 30 minutes. For each of the sealants for organic electroluminescent display elements obtained in Examples 8 to 10, an ultraviolet irradiation device (Oak) was used. The company's "JL-4300-3S" was irradiated with ultraviolet rays at 1500 mJ/cm 2 and then cured by heating at 80 ° C for 30 minutes. Further, the vial was heated in a constant temperature oven at 85 ° C for 100 hours, and the gasification component in the vial was measured using a gas chromatography mass spectrometer ("JMS-Q1050", manufactured by JEOL Ltd.). .
將氣化成分量未達30ppm之情形設為「◎」,將30ppm以上,未達50ppm之情形設為「○」,將50ppm以上,未達100ppm之情形設為「△」,將100ppm以上之情形設為「×」,對防釋氣性進行評價。 When the amount of the gasification component is less than 30 ppm, it is set to "?", and when it is 30 ppm or more, if it is less than 50 ppm, it is set to "○", 50 ppm or more, and when it is less than 100 ppm, it is set to "△", and it is 100 ppm or more. When it is set to "X", the anti-gas release property is evaluated.
根據本發明,可提供一種可抑制釋氣之產生,保存穩定性及塗佈性優異之有機電激發光顯示元件用密封劑。 According to the present invention, it is possible to provide a sealant for an organic electroluminescence display element which is capable of suppressing generation of outgas, and having excellent storage stability and coating properties.
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CN108886849B (en) * | 2016-10-19 | 2022-10-21 | 积水化学工业株式会社 | Sealing agent for organic EL display element and method for producing sealing agent for organic EL display element |
WO2018131553A1 (en) * | 2017-01-12 | 2018-07-19 | 積水化学工業株式会社 | Sealant for organic electroluminescent display element |
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