CN115433146A - Compound for sealing film, composition and sealing film formed by using composition - Google Patents
Compound for sealing film, composition and sealing film formed by using composition Download PDFInfo
- Publication number
- CN115433146A CN115433146A CN202211130531.3A CN202211130531A CN115433146A CN 115433146 A CN115433146 A CN 115433146A CN 202211130531 A CN202211130531 A CN 202211130531A CN 115433146 A CN115433146 A CN 115433146A
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- 239000000203 mixture Substances 0.000 title claims abstract description 103
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000007789 sealing Methods 0.000 title description 6
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 239000004593 Epoxy Substances 0.000 claims abstract description 40
- 239000012044 organic layer Substances 0.000 claims abstract description 40
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 30
- 239000011737 fluorine Substances 0.000 claims abstract description 30
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 20
- 239000012785 packaging film Substances 0.000 claims abstract description 20
- 229920006280 packaging film Polymers 0.000 claims abstract description 20
- 239000003085 diluting agent Substances 0.000 claims abstract description 19
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 8
- 238000005538 encapsulation Methods 0.000 claims description 43
- 239000010410 layer Substances 0.000 claims description 21
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- 125000001033 ether group Chemical group 0.000 claims description 7
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- -1 alkyl glycidyl ether Chemical compound 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 claims description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 claims description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 2
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 claims description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims description 2
- KBCVENKEACAKMN-UHFFFAOYSA-N 2-[[2,3-bis(oxiran-2-ylmethoxy)-1-propoxypropoxy]methyl]oxirane Chemical compound C(C1CO1)OC(C(OCC1CO1)COCC1CO1)OCCC KBCVENKEACAKMN-UHFFFAOYSA-N 0.000 claims description 2
- DWFIEBGQPZWYND-UHFFFAOYSA-N 3-ethyl-3-(phenylmethoxymethyl)oxetane Chemical compound C=1C=CC=CC=1COCC1(CC)COC1 DWFIEBGQPZWYND-UHFFFAOYSA-N 0.000 claims description 2
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 25
- 238000004806 packaging method and process Methods 0.000 abstract description 16
- 238000005452 bending Methods 0.000 abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000035699 permeability Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 37
- 125000001153 fluoro group Chemical group F* 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 13
- 239000010409 thin film Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 239000005022 packaging material Substances 0.000 description 5
- 229910052581 Si3N4 Inorganic materials 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000231 atomic layer deposition Methods 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- 238000007735 ion beam assisted deposition Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 238000012858 packaging process Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- VRHHGFQAXXIRJW-UHFFFAOYSA-N 10h-thiochromeno[3,2-b]pyridine Chemical compound C1=CN=C2CC3=CC=CC=C3SC2=C1 VRHHGFQAXXIRJW-UHFFFAOYSA-N 0.000 description 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
- ZSDAMBJDFDRLSS-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diol Chemical compound OC1=C(F)C(F)=C(O)C(F)=C1F ZSDAMBJDFDRLSS-UHFFFAOYSA-N 0.000 description 1
- SOIAGOLKGAHWEU-UHFFFAOYSA-N 2-(1-adamantyloxymethyl)oxirane Chemical compound C1C(C2)CC(C3)CC2CC13OCC1CO1 SOIAGOLKGAHWEU-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- ODSXJQYJADZFJX-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)phenol Chemical compound OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ODSXJQYJADZFJX-UHFFFAOYSA-N 0.000 description 1
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005410 aryl sulfonium group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- HANKSFAYJLDDKP-UHFFFAOYSA-N dihydrodicyclopentadiene Chemical compound C12CC=CC2C2CCC1C2 HANKSFAYJLDDKP-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- BNRNAKTVFSZAFA-UHFFFAOYSA-N hydrindane Chemical compound C1CCCC2CCCC21 BNRNAKTVFSZAFA-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical group CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- IWDANOJGJIFBEL-UHFFFAOYSA-N spiro[3.4]octane Chemical compound C1CCC21CCCC2 IWDANOJGJIFBEL-UHFFFAOYSA-N 0.000 description 1
- PHICBFWUYUCFKS-UHFFFAOYSA-N spiro[4.4]nonane Chemical compound C1CCCC21CCCC2 PHICBFWUYUCFKS-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
- C07D303/27—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having all hydroxyl radicals etherified with oxirane containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
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Abstract
The invention belongs to the technical field of organic film packaging, and relates to a compound and a composition for a packaging film and the packaging film formed by the composition. The composition for the packaging film comprises the following components in parts by weight: 30 to 60 portions of fluorine-containing monomer, 10 to 30 portions of alicyclic epoxy monomer, 10 to 30 portions of diluent monomer, 0.01 to 10 portions of photoinitiator and 0.01 to 5 portions of photosensitizer. In the composition, the addition of the fluorine-containing monomer enables the cured packaging composition to have a lower dielectric coefficient, which is beneficial to increasing the hydrophobic property of the organic layer, effectively reducing the water vapor permeability of the organic layer and increasing the thermal stability of the organic layer. Meanwhile, the fluorine-containing monomer and the alicyclic epoxy monomer have good compatibility, and the fluorine-containing monomer and the alicyclic epoxy monomer have synergistic effect, so that the dielectric coefficient of the organic layer can be effectively reduced, and the tensile strength of the organic layer is improved to 25-30 MPa and has good bending performance.
Description
Technical Field
The invention belongs to the technical field of organic film packaging, and relates to a compound and a composition for a packaging film and the packaging film formed by the composition.
Background
Organic Light-Emitting Diodes (OLEDs) are electroluminescent semiconductor devices. One of the biggest problems of the OLED at the present stage is that moisture and oxygen exist in the OLED device after long-time use, and it is the most direct and effective method to improve the OLED packaging process in order to prolong the service life of the OLED. The packaging process usually adopts a thin film packaging structure with alternately laminated inorganic layers/organic layers/inorganic layers, wherein the organic layers are usually prepared by using ultraviolet light curable monomers. However, with the rapid development of electronic products, the processing and propagation of digital information are gradually moving toward higher frequencies and higher speeds, and the dielectric properties of electronic packaging materials are required to be better, and packaging materials having a low dielectric constant (k < 3) are urgently required in order to reduce the delay of resistance and capacitance. The lower dielectric coefficient can reduce the parasitic resistance and dielectric loss of the packaging layer, and is expected to improve the electrical characteristics of the packaging material, particularly the electrical insulation property under high frequency. Therefore, the development of polymer encapsulation materials with low dielectric constant and dielectric loss has become one of the focuses of great interest in the industry.
In addition, in order to achieve flexibility of the OLED, since the encapsulating material needs to be flattened or thinned, an inkjet printing coating method is often used to coat the encapsulating composition using an inkjet device. For ink jet printing, the viscosity must not be too high, otherwise the microscopic nozzles on the print head may clog. Compared with the common packaging material of an acrylate system, the epoxy system has the advantages of better chemical stability, better mechanical property, lower curing shrinkage rate and the like. However, the viscosity of the packaging material of the epoxy system is high, the material is brittle after curing, the water absorption and the dielectric coefficient are not ideal, and the dielectric coefficient k value of the common epoxy system is 3-4.
Disclosure of Invention
The present invention is directed to overcoming the above-mentioned disadvantages of the prior art and providing a compound for an encapsulation film, a composition and an encapsulation film formed using the composition, and the cured encapsulation composition has a low dielectric constant and excellent hardness and tensile strength.
In order to achieve the purpose, the invention provides the following technical scheme:
in one aspect, the present invention provides a compound for an encapsulation film, wherein the compound for an encapsulation film has a structural formula of formula i:
in the formula I, n 1 Is an integer of 0 to 10, n 2 Is 1 or 2;
R 1 is F, a plurality of F substituted or unsubstituted C6 to C30 phenyl groups, a plurality of F substituted or unsubstituted C1 to C10 alkyl groups, and R 1 The number of the (B) is 1 to 5;
R 2 is any one of a single bond, O, a substituted or unsubstituted C1 to C10 alkylene group, and a substituted or unsubstituted C1 to C10 alkylene ether group;
in the context of the present invention, the alkylene ether group may comprise all functional groups in which at least one alkylene group is bonded to at least one oxygen atom, and may comprise, for example, (alkylene-oxy) n Alkylene, (alkylene-oxy-alkylene) n-alkylene, alkylene-oxy or- (oxy-alkylene) n - (wherein n is an integer of 1 to 10);
x is an epoxy group M, and the epoxy group M comprises any one of monocyclic epoxy, polycyclic epoxy and styrene-acrylic epoxy.
Further, X is any one of structures shown in formula 1-1, formula 1-2, formula 1-3, formula 1-4 and formula 1-5:
wherein, is the attachment site; r 3 Is any one of H, C1 to C6 alkyl, C1 to C6 fluoroalkyl, alkenyl and phenyl; r 4 Is any one of a single bond and an alkylene ether group having 1 to 6 carbon atoms.
Further, the content of F atoms in the compound for the packaging film is 10-35%; wherein the F atom content (%) = total molecular weight of F atoms in the monomer/relative molecular weight of the monomer × 100%.
In the present invention, the atomic content of the compound F for an encapsulation film is defined to be 10% to 35% so that the cured encapsulation composition has a low dielectric constant and excellent hardness and tensile strength. This is because: when the content of the F atom is higher than 35%, the electrostatic repulsion among molecules of the compound for the packaging film far exceeds the attraction, so that the molecular chain spacing is increased, the Tg temperature is reduced, the cured packaging composition is softer, the hardness and the tensile strength are poor, and the packaging effect is influenced; when the F atom content is less than 10%, the dielectric constant of the cured encapsulation film is high.
Further, the compound for the encapsulation film includes at least one of structures shown in formula 1, formula 2, formula 3, formula 4, formula 5, and formula 6:
on the other hand, the invention provides a composition for packaging films, which comprises the following components in parts by weight: 30 to 60 parts of fluorine-containing monomer, 10 to 30 parts of alicyclic epoxy monomer, 10 to 30 parts of diluent monomer, 0.01 to 10 parts of photoinitiator and 0.01 to 5 parts of photosensitizer; the fluorine-containing monomer is the compound for the packaging film.
Further, the addition amount of the photoinitiator is 0.1-10% of the total mass of the packaging composition; the addition amount of the photosensitizer is 0.1-5% of the total mass of the packaging composition.
Further, the alicyclic epoxy monomer has a structural formula shown in formula II:
wherein n is an integer of 1 to 3;
q is a single bond, an alkyl chain with the carbon chain length of 1-6, or an alkoxy chain with the carbon chain length of 1-6;
y has a bicyclic or tricyclic structure; EP is an epoxy group N which is monocyclic epoxy or phenylpropylene epoxy.
Further, each Y is independently any one of bicyclo [4.1.0] heptane, hexahydroindan, tetrahydrodicyclopentadiene, adamantane, 5,6-dihydrodicyclopentadiene, spiro [4.4] nonane, (1s, 4 s) -bicyclo [2.2.1] heptane, spiro [3.4] octane, and decahydronaphthalene.
Further, the epoxy group N includes: monocyclic epoxy, and benzocycloepoxy, etc., representing the structures:
in the invention, by introducing the F atom with a specific content, on one hand, C-F has smaller dipole and lower polarizability than C-H, and on the other hand, the F atom can increase the free volume as a substituent on a benzene ring, so that the introduction of the F atom with a specific content into an organic layer for encapsulating the OLED can greatly reduce the dielectric coefficient of the organic layer. In addition, the introduction of F atoms into the epoxy monomer is helpful to increase the hydrophobic property of the organic layer, so that the water vapor transmission rate of the organic layer is effectively reduced, and the thermal stability of the organic layer is also increased.
Meanwhile, the inventor finds that the fluorine-containing monomer and the alicyclic epoxy monomer have good compatibility, and the fluorine-containing monomer and the alicyclic epoxy monomer can effectively reduce the dielectric coefficient of the organic layer under the synergistic action of the fluorine-containing monomer and the alicyclic epoxy monomer, so that the dielectric coefficient of the organic layer prepared by the fluorine-containing monomer can be reduced to 2.7-2.8, and simultaneously the tensile strength of the organic layer is improved, so that the tensile strength of the organic layer is 25-30 MPa, and the organic layer has good bending performance (can be bent for twenty-thousand times without cracking). This is because: on one hand, the fluorine-containing monomer and the alicyclic epoxy monomer are of large-volume structures with poor regularity, so that the regularity of molecular chains in the system is reduced, the close packing of chain segments in the fluorine-containing monomer and the alicyclic epoxy monomer is prevented to a certain extent by the F atoms with specific content, the chain stacking density is relatively reduced, the free volume is increased, and the dielectric coefficient of an organic layer is reduced. On the other hand, the introduction of the fluorine atoms can promote the formation of hydrogen bonds in molecules, so that the interaction between molecules is strengthened, the aggregation state of the molecules and the acting force with a base material are improved, and the tensile strength of the organic layer and the adhesive force with the base material are effectively improved.
Further, the diluent monomer is one or more of a monoepoxy-functional or polyepoxy-functional aliphatic glycidyl ether diluent monomer and an oxetane diluent monomer.
Further, the aliphatic glycidyl ether diluent monomer is one or more of 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polypropylene glycol diglycidyl ether, ethylene glycol diglycidyl ether, glycerol triglycidyl ether, butyl glycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, propoxyglycerol triglycidyl ether, 2-ethylhexyl glycidyl ether and C12-C14 alkyl glycidyl ether.
Further, the oxetanes are one or more of 3-ethyl-3- ((oxirane-2-methoxy) methyl) oxetane, 3-hydroxymethyl-3-ethyloxetane, 3- (benzyloxymethyl) -3-ethyloxetane, 3-ethyl-3-methoxyoxetane methacrylate, 4,4-bis [ (3-ethyl-3-oxetane) methoxymethyl ] biphenyl, 1,4-bis [ (3-ethyl-3-oxetane) methoxymethyl ] benzene, 3,3' - (oxybis) bis- (3-ethyl) -oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxygen.
Preferably, the diluent monomer is a mixture of an aliphatic glycidyl ether diluent monomer and an oxetane diluent monomer. More preferably, the weight ratio of the aliphatic glycidyl ether diluent monomer to the oxetane diluent monomer is (1 to 5): (3-9).
Further, the photoinitiator is one or more of diazonium salt, ferrocenium salt and aryl sulfonium salt.
Further, the photosensitizer is one or more of benzophenone, thioxanthone, xanthone, anthracene, pyrene, thiazine and azathioxanthene.
The preparation method of the encapsulation composition of the present invention is similar to the preparation method of the conventional encapsulation composition, that is, the fluorine-containing monomer, the alicyclic epoxy monomer, the diluent monomer and the photoinitiator are added into a brown glass container, and then the mixture is shaken and mixed for 2 hours at room temperature to obtain the encapsulation composition.
In another aspect, the present invention further provides an encapsulation film, which includes an inorganic layer and an organic layer alternately disposed in sequence, and the outermost layer is an inorganic layer; the organic layer is prepared from the encapsulating composition; the packaging film is coated with the inorganic layer through lamination to isolate the organic layer in the organic light-emitting device from external oxygen and moisture, thereby achieving the purpose of protecting the film of the organic light-emitting device and having the properties of low hygroscopicity and flexibility.
In the invention, each inorganic layer in the packaging film is independently selected from silicon nitride, silicon oxynitride, silicon oxide, aluminum oxide, zirconium oxide, titanium oxide or zinc oxide, preferably silicon nitride; may be formed by sputtering, chemical Vapor Deposition (CVD), atomic Layer Deposition (ALD), ion Beam Assisted Deposition (IBAD) of oxides or nitrides of metals well known to those skilled in the art.
Further, the thickness of the inorganic layer is 50 to 500nm, preferably 100 to 400nm; the thickness of the organic layer is 1 to 20 μm, preferably 8 μm.
Compared with the prior art, the technical scheme provided by the invention has the following beneficial effects:
1. f atoms are introduced into the epoxy monomer, so that the hydrophobic property of the organic layer is increased, the water vapor transmittance of the organic layer is effectively reduced, and the thermal stability of the organic layer is also increased; meanwhile, the dielectric coefficient of the organic layer can be greatly reduced by introducing F atoms with a specific F atom content.
2. Because the fluorine-containing monomer and the alicyclic epoxy monomer have good compatibility, the fluorine-containing monomer and the alicyclic epoxy monomer have synergistic effect, the dielectric coefficient of the organic layer is effectively reduced, the dielectric coefficient of the organic layer prepared by the fluorine-containing monomer and the alicyclic epoxy monomer can be reduced to 2.7-2.8, and meanwhile, the organic layer also has excellent tensile strength, and the tensile strength is 25 MPa-30 MPa.
3. The packaging composition prepared from the compound for packaging films has excellent ink-jet printing performance, the viscosity is 15-30 mPa.S at 25 ℃, the surface tension is 20-38 mN/m, the flatness of the cured packaging composition can be ensured, the subsequent deposition of inorganic materials is facilitated, and the packaging composition has an excellent barrier effect on water vapor.
4. The packaging composition prepared from the compound for packaging films is an epoxy system, and an organic layer formed after curing has excellent mechanical property, higher adhesion with a base material, tensile strength of 25-30 MPa and good bending property (can be bent for twenty-thousand times without cracking).
Detailed Description
The exemplary embodiments will be described herein in detail, and the embodiments described in the following exemplary embodiments do not represent all embodiments consistent with the present invention. Rather, they are merely examples of compositions, methods consistent with certain aspects of the invention, as detailed in the appended claims.
In order to make those skilled in the art better understand the technical solution of the present invention, the following detailed description of the present invention is made with reference to the embodiments.
In one aspect, the present invention provides a compound for an encapsulation film, wherein the compound for an encapsulation film has a structural formula of formula i:
in the formula I, n 1 Is 0 &An integer of 10, n 2 Is 1 or 2;
R 1 is F, a plurality of F substituted or unsubstituted C6 to C30 phenyl groups, a plurality of F substituted or unsubstituted C1 to C10 alkyl groups, R 1 The number of the (B) is 1 to 5;
R 2 is any one of a single bond, O, a substituted or unsubstituted C1 to C10 alkylene group, and a substituted or unsubstituted C1 to C10 alkylene ether group;
x is an epoxy group M, and the epoxy group M is any one of monocyclic epoxy, polycyclic epoxy and styrene-acrylic epoxy.
Further, X is any one of structures shown in formulas 1-1, 1-2, 1-3, 1-4 and 1-5:
wherein, is the attachment site; r 3 Is any one of H, C1 to C6 alkyl, C1 to C6 fluoroalkyl, alkenyl and phenyl; r 4 Is any one of a single bond and an alkylene ether group having 1 to 6 carbon atoms.
Further, the content of F atoms in the compound for the sealing film is 10 to 35%.
Further, the compound for the encapsulation film includes at least one of the structures shown in the following formula 1, formula 2, formula 3, formula 4, formula 5, formula 6:
on the other hand, the invention provides a composition for packaging films, which comprises the following components in parts by weight: 30 to 60 parts of fluorine-containing monomer, 10 to 30 parts of alicyclic epoxy monomer, 10 to 30 parts of diluent monomer, 0.01 to 10 parts of photoinitiator and 0.01 to 5 parts of photosensitizer; the fluorine-containing monomer is the compound for the packaging film.
Further, the addition amount of the photoinitiator is 0.1-10% of the total mass of the packaging composition; the addition amount of the photosensitizer is 0.1-5% of the total mass of the packaging composition.
The following examples are illustrated by formula 1, formula 2 and formula 6, and the specific preparation processes are as follows:
preparation example 1
The preparation example provides a compound for a packaging film, the structural formula of the compound is shown as formula 1, and the specific synthetic route and the preparation process are as follows:
230.1g of 3,5-bis (trifluoromethyl) phenol, 96.9g of ethylene carbonate and 6.9g of potassium carbonate are added into a reaction bottle, 200mL of DMF is added, the reaction is carried out at 110 ℃, TLC monitors the reaction until the reaction of the raw materials is finished, the system is added into 1000mL of water after the reaction is cooled to room temperature, the precipitate is filtered, washed with water for three times, and dried in vacuum to obtain an intermediate 1-A, wherein the yield is 96%.
80g of sodium hydroxide and 500mL of water are placed in a 2500mL round-bottom flask, 274.2g of intermediate 1-A and 16.1g of tetrabutylammonium bromide are added with stirring, 138.8g of epichlorohydrin is slowly dropped by using an isopiestic dropping funnel under the ice bath condition, and the dropping is finished within 2 hours. The reaction was carried out overnight at room temperature, TLC was carried out until the reaction was completed, 500mL of water was added, extraction was carried out with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the product was obtained by column chromatography with a yield of 92%.
Preparation example 2
The preparation example provides a compound for a packaging film, the structural formula of the compound is shown as formula 2, and the specific synthetic route and the preparation process are as follows:
184.1g of pentafluorophenol, 96.9g of ethylene carbonate and 6.9g of potassium carbonate are added into a reaction bottle, 200mL of DMF is added, the reaction is carried out at 110 ℃, TLC is used for monitoring the reaction until the reaction of the raw materials is finished, the system is added into 1000mL of water after being cooled to room temperature, the precipitate is filtered, washed with water for three times, and dried in vacuum to obtain the intermediate 2-A with the yield of 93%.
80g of sodium hydroxide and 500mL of water are placed in a 2500mL round-bottom flask, 228.1g of intermediate 2-A and 16.1g of tetrabutylammonium bromide are added with stirring, 138.8g of epichlorohydrin is slowly dropped by using an isopiestic dropping funnel under the ice bath condition, and the dropping is finished within 2 hours. The reaction was carried out overnight at room temperature, TLC was carried out until the reaction was completed, 500mL of water was added, extraction was carried out with ethyl acetate (200 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the product was obtained by column chromatography with a yield of 87%.
Preparation example 3
The preparation example provides a compound for a packaging film, the structural formula of the compound is shown as formula 6, and the specific synthetic route and the preparation process are as follows:
182.1g of 2,3,5,6-tetrafluorohydroquinone, 193.8g of ethylene carbonate and 13.8g of potassium carbonate are added into a reaction bottle, 300mL of DMF is added, the reaction is carried out at 110 ℃, TLC monitors the reaction until the reaction of the raw materials is finished, the system is added into 1200mL of water after the reaction is cooled to room temperature, the precipitate is filtered, washed with water for three times, and dried in vacuum to obtain an intermediate 6-A, wherein the yield is 87%.
160g of sodium hydroxide and 800mL of water are placed in a 2500mL round-bottom flask, 270.2g of intermediate 6-A and 32.2g of tetrabutylammonium bromide are added with stirring, 277.6g of epichlorohydrin is slowly added dropwise through a constant-pressure dropping funnel under ice bath conditions, and the dropwise addition is completed within 3 hours. The reaction was carried out overnight at room temperature, TLC was carried out until the reaction was complete, 800mL of water was added, extraction was carried out with ethyl acetate (300 mL. Times.3), the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the product was isolated by column chromatography in 78% yield.
In another aspect, the invention also provides a composition for an encapsulation film, and an encapsulation film prepared by using the composition. To demonstrate the important role of the fluorine-containing monomer (compound for encapsulating film) and the alicyclic epoxy monomer in the composition, the inventors verified by the following test examples and test comparative examples, as follows:
the following details of the components used in the test comparative examples and test examples are as follows:
(A) Compound for encapsulation film: a1: a compound of formula 1 (F atom content = 34.5%); a2: a compound of formula 2 (F atom content = 33.5%); a3: a compound of formula 6 (F atom content = 19.9%); a4: hexafluoroisopropyl methacrylate (F atom content = 48.3%) (sigma-aldrich).
(B) Alicyclic epoxy monomer: 2- [ (1-adamantyloxy) methyl ] oxirane (beijing carbofuran technologies, inc.);
(C) Diluting monomers: (C1) Polyethylene glycol diglycidyl ether (Jiangsu Sanmu group, inc.), (C2) 3-ethyl-3- [ [ (2-ethylhexyl) oxy ] methyl ] oxetane (alatin);
(D) Photoinitiator (2): triarylsulfonium hexafluorophosphate (sigma-aldrich);
(E) A photosensitizer: 2-isopropyl thioxanthone (Changzhou powerful new electronic materials Co., ltd.).
Example 1
The embodiment provides a composition (I) for an encapsulation film, which comprises the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2 parts of component D and 0.5 part of component E; wherein, the component A is A1 which is a fluorine-containing monomer of a formula 1, and the F atom content is =34.5%; component C is a mixture of 6 parts of C1 and 12 parts of C2, component D is added in an amount of 2.3% by mass and component E is added in an amount of 0.6% by mass of the total composition.
In another aspect, the present embodiment further provides an encapsulation film, which includes an inorganic layer and an organic layer alternately disposed in sequence, and the outermost layer is an inorganic layer; the organic layer is prepared from the packaging composition (I); the packaging film is coated with the inorganic layer through lamination to isolate the organic layer in the organic light-emitting device from external oxygen and moisture, thereby achieving the purpose of protecting the film of the organic light-emitting device and having the properties of low hygroscopicity and flexibility.
Specifically, each inorganic layer in the encapsulation film is independently selected from silicon nitride, silicon oxynitride, silicon oxide, aluminum oxide, zirconium oxide, titanium oxide or zinc oxide, and preferably is silicon nitride; may be formed by sputtering, chemical Vapor Deposition (CVD), atomic Layer Deposition (ALD), ion Beam Assisted Deposition (IBAD) of oxides or nitrides of metals well known to those skilled in the art.
Further, the thickness of the inorganic layer is 50 to 500nm, preferably 100 to 400nm; the thickness of the organic layer is 1 to 20 μm, preferably 8 μm.
Example 2
The embodiment provides a composition (II) for an encapsulation film, which comprises the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2 parts of component D and 0.5 part of component E; wherein, the component A is A2, namely the fluorine-containing monomer of the formula 2, and the F atom content is =33.5%; component C is a mixture of 6 parts of C1 and 12 parts of C2, component D is added in an amount of 2.3% by mass and component E is added in an amount of 0.6% by mass of the total composition.
The detailed process for preparing an organic thin film using the composition (II) is the same as that of example 1, and thus, the detailed description thereof is omitted.
Example 3
The embodiment provides a composition (III) for an encapsulation film, which comprises the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2 parts of component D and 0.5 part of component E; wherein, the component A is A3 which is a fluorine-containing monomer of formula 6, and the F atom content is =19.9%; component C is a mixture of 6 parts of C1 and 12 parts of C2, component D is added in an amount of 2.3% by mass and component E is added in an amount of 0.6% by mass of the total composition.
The specific process for preparing an organic thin film using the composition (III) is the same as that of example 1, and thus, detailed description thereof will be omitted.
Example 4
The embodiment provides a composition (IV) for an encapsulation film, which comprises the following components in parts by weight: 60 parts of component A, 30 parts of component B, 30 parts of component C, 2.9 parts of component D and 0.7 part of component E; wherein, the component A is A1 which is a fluorine-containing monomer of a formula 1, and the F atom content is =34.5%; component C is a mixture of 10 parts of C1 and 20 parts of C2, component D is added in an amount of 2.3% by mass and component E is added in an amount of 0.6% by mass of the total composition.
The specific process for preparing an organic thin film using the composition (IV) is the same as that of example 1, and will not be described herein.
Example 5
The embodiment provides a composition (V) for an encapsulation film, which comprises the following components in parts by weight: 30 parts of component A, 10 parts of component B, 10 parts of component C, 1.2 parts of component D and 0.3 part of component E; wherein, the component A is A1 which is a fluorine-containing monomer of a formula 1, and the F atom content is =34.5%; component C is a mixture of 3 parts of C1 and 7 parts of C2, component D is added in an amount of 2.3% and component E is added in an amount of 0.6% of the total mass of the composition.
The specific process for preparing an organic thin film using the composition (V) is the same as that of example 1, and is not described herein again.
Example 6
The embodiment provides a composition (VI) for an encapsulation film, which comprises the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2 parts of component D and 0.5 part of component E; wherein, the component A is a mixture formed by 15 parts of A1, 15 parts of A2 and 15 parts of A3, namely a mixture of compounds with structures shown in formula 1, formula 2 and formula 6; component C is a mixture of 6 parts of C1 and 12 parts of C2, component D is added in an amount of 2.3% by mass and component E is added in an amount of 0.6% by mass of the total composition.
The specific process for preparing an organic thin film using the composition (VI) is the same as that of example 1, and thus, will not be described herein.
Example 7
The embodiment provides a composition (VII) for an encapsulation film, which comprises the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2.0 parts of component D and 0.5 part of component E; wherein component a is A1, i.e., a fluorine-containing monomer of formula 1, the F atom content =34.5%, component C is composed of only 18 parts of C1, component D is added in an amount of 2.3% by mass of the total composition, and component E is added in an amount of 0.6% by mass of the total composition.
The specific process for preparing an organic thin film using the composition (VII) is the same as that of example 1, and thus, detailed description thereof is omitted.
Comparative example 1
The comparative example provides composition (eight) for an encapsulation film, comprising the following components in parts by weight: 20 parts of component B, 18 parts of component C, 1 part of component D and 0.2 part of component E; wherein, the component A is not contained, the component C is a mixture formed by 6 parts of C1 and 12 parts of C2, the addition amount of the component D is 2.6 percent of the total mass of the composition, and the addition amount of the component E is 0.5 percent of the total mass of the composition.
The specific process for preparing an organic thin film using the composition (VIII) is the same as that of example 1, and is not described herein again.
Comparative example 2
The comparative example provides composition (nine) for an encapsulation film, comprising the following components in parts by weight: 45 parts of component A, 18 parts of component C, 1.6 parts of component D and 0.4 part of component E; wherein component B is not contained, component a is A2, i.e., a fluorine-containing monomer of formula 2, the F atom content =33.5%, component C is a mixture of 6 parts of C1 and 12 parts of C2, component D is added in an amount of 2.5% by mass of the total composition, and component E is added in an amount of 0.6% by mass of the total composition.
The specific process for preparing an organic thin film using the composition (nine) is the same as that of example 1, and is not described herein again.
Comparative example 3
The comparative example provides a composition (ten) for an encapsulating film, comprising the following components in parts by weight: 45 parts of component A, 20 parts of component B, 1.6 parts of component D and 0.4 part of component E; wherein component C is not contained, component a is A1, i.e., the fluorine-containing monomer of formula 1, the F atom content =34.5%, the addition amount of component D is 2.4% of the total mass of the composition, and the addition amount of component E is 0.6% of the total mass of the composition.
The specific process for preparing an organic thin film using the composition (ten) is the same as that of example 1, and is not described herein again.
Comparative example 4
The comparative example provides a composition (eleven) for an encapsulating film, comprising the following components in parts by weight: 45 parts of component A, 20 parts of component B, 18 parts of component C, 2.0 parts of component D and 0.5 part of component E; wherein the component A is A4, namely hexafluoroisopropyl methacrylate, the F atom content is =48.3%, the addition amount of the component D is 2.3% of the total mass of the composition, and the addition amount of the component E is 0.6% of the total mass of the composition.
The specific process for preparing an organic thin film using the composition (eleven) was the same as the preparation process of example 1, and will not be described herein.
The compositions obtained in examples 1 to 7 and comparative examples 1 to 4 were UV-cured and tested as follows:
(1) Water vapor transmission rate: water vapor transmission rate test System (PERMATRAN-W3/33, manufactured by MOCON, USA). The ultraviolet light curable glue composition is prepared at 30mW/cm 2 It was subjected to UV curing by UV irradiation for 120s to produce a cured sample having a layer 8 μm thick. The water vapor transmission rate was determined using a water vapor transmission rate tester (PERMATRAN-W3/33, manufactured by MOCON) at 85 ℃ and 85% relative humidity for 24h at a layer thickness of 8 μm.
(2) Dielectric coefficient: the material is made into a wafer with the diameter of 20mm and the thickness of 8 mu m, and the dielectric coefficient of the wafer is tested by utilizing an Agilent 4294A type precision impedance analyzer, wherein the testing frequency is 10GHz.
(3) Tensile strength: according to GB/T1040-92 general test method for Plastic mechanical Properties (tensile); and (3) testing conditions are as follows: the tensile speed is 1mm/min, at least 5 samples are used in each group, and the test results are averaged.
(4) Light transmittance: the encapsulating composition was inkjet printed on an ITO glass substrate and at 30mW/cm 2 It was subjected to UV curing by UV irradiation for 120s to produce a specimen having dimensions of 3 cm. Times.7.5 cm. Times.8 μm (width. Times. Length. Times. Thickness), and then measured by an ultraviolet spectrophotometer (Fluoromax-4, HORIBA Jobin Yvon France)The light transmittance of the cured film in the visible light range of 400 nm-700 nm.
(5) Printing performance: the ink jet printer was continuously printed for 100 hours and observed with ink droplets to see if clogging occurred. No hole blockage occurred, indicated by the symbol delta, and hole blockage occurred, indicated by the symbol tangle-solidup.
According to the compositions and proportions (unit: parts by weight) in the above examples 1 to 7 and comparative examples 1 to 4, the raw material compounds were put into a reaction kettle for 30min, stirred uniformly and filtered to obtain the encapsulating compositions corresponding to examples 1 to 7 and comparative examples 1 to 4, respectively.
The results of the performance tests of the compositions of examples 1-7 and comparative examples 1-4 are shown in the following table:
as can be seen from the data of the above table, the compositions for encapsulation films provided in examples 1 to 7 have excellent ink jet printing performance and can provide an organic layer having a lower low dielectric coefficient and excellent tensile strength after curing. In addition, it is clear from the combination of examples 1 to 7 and comparative examples 1 to 2 that, if the encapsulating composition lacks any one of the compound for encapsulating film (component a) and the alicyclic epoxy monomer (component B), the dielectric coefficient of the encapsulating composition after curing is > 3, and the mechanical properties (tensile strength) are not good; it can be seen from the combination of examples 1 to 7 and comparative example 3 that, if the diluent monomer C is not contained, the cured encapsulation composition has poor ink jet printing performance and poor light transmittance of the organic layer. When the content of F atoms in the fluorine-containing monomer is more than 35%, the cured sealing composition has a low tensile strength and a low water vapor barrier property, as compared with comparative example 4 in examples 1 to 7.
The foregoing are merely exemplary embodiments of the present invention, which enable those skilled in the art to understand or practice 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.
It is to be understood that the present invention is not limited to what has been described above, and that various modifications and changes may be made without departing from the scope thereof. The scope of the invention is limited only by the appended claims.
Claims (10)
1. A compound for an encapsulation film, wherein the compound for an encapsulation film has a structural formula of formula i:
in the formula I, n 1 Is an integer of 0 to 10, n 2 Is 1 or 2;
R 1 is F, a plurality of F substituted or unsubstituted C6 to C30 phenyl groups, a plurality of F substituted or unsubstituted C1 to C10 alkyl groups, R 1 The number of the (B) is 1 to 5;
R 2 is any one of a single bond, O, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C1 to C10 alkylene ether group;
x is an epoxy group M, and the epoxy group M is any one of monocyclic epoxy, polycyclic epoxy and styrene-acrylic epoxy.
2. The compound for encapsulation film according to claim 1, wherein X is any one of structures represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, and formula 1-5:
wherein is a ligation site; r 3 Is any one of H, C1 to C6 alkyl, C1 to C6 fluoroalkyl, alkenyl and phenyl; r is 4 Is any one of a single bond and an alkylene ether group having 1 to 6 carbon atoms.
3. The compound for an encapsulation film according to claim 1, comprising at least one of the structures represented by the following formula 1, formula 2, formula 3, formula 4, formula 5, and formula 6:
4. the composition for the packaging film is characterized by comprising the following components in parts by weight: 30 to 60 parts of fluorine-containing monomer, 10 to 30 parts of alicyclic epoxy monomer, 10 to 30 parts of diluent monomer, 0.01 to 10 parts of photoinitiator and 0.01 to 5 parts of photosensitizer; the fluorine-containing monomer is the compound for an encapsulating film according to any one of claims 1 to 3.
5. The composition for encapsulation film according to claim 4, wherein the alicyclic epoxy monomer has a structural formula of formula II:
in the formula II, n is an integer of 1-3;
q is any one of a single bond, an alkyl chain with a carbon chain length of 1-6 and an alkyl ether with a carbon chain length of 1-6;
y has a bicyclic or tricyclic structure;
EP is an epoxy group N which is monocyclic epoxy or phenylpropyl epoxy.
6. The composition for an encapsulating film according to claim 5, wherein the epoxy group N is any one of the following structural formulae:
7. the composition for encapsulation film according to claim 4, wherein the diluent monomer is one or more of a monoepoxy-functional or polyepoxy-functional aliphatic glycidyl ether diluent monomer and an oxetane diluent monomer.
8. The composition for encapsulation film according to claim 7, wherein the aliphatic glycidyl ether diluent monomer is one or more of 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polypropylene glycol diglycidyl ether, ethylene glycol diglycidyl ether, glycerol triglycidyl ether, butyl glycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, propoxyglycerol triglycidyl ether, 2-ethylhexyl glycidyl ether, and C12-C14 alkyl glycidyl ether.
9. The composition for an encapsulation film according to claim 7, wherein the oxetane is one or more of 3-ethyl-3- ((oxirane-2-methoxy) methyl) oxetane, 3-hydroxymethyl-3-ethyloxetane, 3- (benzyloxymethyl) -3-ethyloxetane, 3-ethyl-3-methoxyoxetane methacrylate, 4,4-bis [ (3-ethyl-3-oxetane) methoxymethyl ] biphenyl, 1,4-bis [ (3-ethyl-3-oxetane) methoxymethyl ] benzene, 3,3' - (oxybutylene) bis- (3-ethyl) -oxetane, and 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxygen.
10. An encapsulation film comprising an inorganic layer and an organic layer alternately arranged in this order, with the inorganic layer as the outermost layer, characterized in that the organic layer is made of the encapsulation composition according to any one of claims 4 to 9; the thickness of the inorganic layer is 50-500 nm, and the thickness of the organic layer is 1-20 μm.
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