CN112390820A - Composition monomer capable of being cured to form film, composition thereof and application of composition - Google Patents
Composition monomer capable of being cured to form film, composition thereof and application of composition Download PDFInfo
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- CN112390820A CN112390820A CN202011210404.5A CN202011210404A CN112390820A CN 112390820 A CN112390820 A CN 112390820A CN 202011210404 A CN202011210404 A CN 202011210404A CN 112390820 A CN112390820 A CN 112390820A
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- 239000000178 monomer Substances 0.000 title claims abstract description 52
- 239000012044 organic layer Substances 0.000 claims abstract description 41
- 239000010410 layer Substances 0.000 claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 21
- 238000005538 encapsulation Methods 0.000 claims abstract description 16
- 229920006280 packaging film Polymers 0.000 claims abstract description 12
- 239000012785 packaging film Substances 0.000 claims abstract description 12
- -1 diazonium salt compounds Chemical class 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000151 deposition Methods 0.000 claims description 7
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 5
- 238000005229 chemical vapour deposition Methods 0.000 claims description 5
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 125000004386 diacrylate group Chemical group 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000007870 radical polymerization initiator Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- NQOGBCBPDVTBFM-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)COC(C)CO NQOGBCBPDVTBFM-UHFFFAOYSA-N 0.000 claims description 2
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical group C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000008062 acetophenones Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- JZZSYBRYYXBMSD-UHFFFAOYSA-N boric acid sulfane Chemical class OB(O)O.S JZZSYBRYYXBMSD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- 125000000686 lactone group Chemical group 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical group CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical group OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 6
- 239000001301 oxygen Substances 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- 238000004806 packaging method and process Methods 0.000 abstract description 3
- 239000010409 thin film Substances 0.000 abstract description 3
- 230000009975 flexible effect Effects 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001514 detection method Methods 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Wrappers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention relates to the technical field of thin film packaging, in particular to a composition monomer capable of being cured to form a film, a composition thereof and application of the composition, wherein the structural general formula of the composition monomer is as follows:
Description
Technical Field
The invention relates to the technical field of thin film packaging, in particular to a composition monomer capable of being cured to form a film, a composition thereof and application of the composition.
Background
To meet the growing demand of the market for flexible display devices, Organic Light Emitting Diodes (OLEDs) are considered to be the most promising next generation flexible lighting devices. The first problem to be considered before the application of flexible OLEDs is the problem of flexible encapsulation, since flexible OLEDs are very susceptible to moisture and oxygen, and they are easily degraded in oxygen or moisture-containing ambient conditions. To solve this problem, many researchers have conducted a great deal of research work in order to effectively encapsulate flexible OLEDs. The most common packaging method is to use organic or inorganic binary structures to alternately deposit binary films as moisture and oxygen barrier layers. In the binary structure, inorganic materials are prone to generate pinholes and cracks during deposition, and the thin film formed in this way can directly permeate moisture and oxygen, resulting in the performance degradation of the flexible OLED device. Furthermore, the inherent brittleness of inorganic materials is not suitable for application in flexible OLEDs. Therefore, the development of high performance organic barrier materials and their flexibility, good optical transparency and mechanical robustness have great application value for efficiently encapsulating flexible OLEDs.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a curable film-forming composition monomer, a composition thereof and application of the composition.
The technical scheme of the invention is as follows:
it is a first object of the present invention to provide a curable film-forming composition monomer having a structural formula of formula 1:
in the formula:
R1、R2are identical or different from each other and are each independently hydrogen or methyl; r3、R4The same or different from each other, and each is independently selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, or a hydroxyl group.
Preferably, the monomer of the composition has the following structural formula:
the second object of the present invention is to provide a curable film-forming composition comprising 9.5 to 90% by mass of component A which is a monomer of the composition of claim 1, 9.5 to 90% by mass of component B which is one or more acrylic-based compounds curable with light reception, and 0.5 to 10% by mass of component C which is one or more photoinitiators.
As a preference of the present invention, the component B is acrylate and methacrylate; the component C is a photopolymerization initiator and/or a free radical polymerization initiator.
As a preferred aspect of the present invention, the acrylate monomers include monoacrylate monomers, diacrylate monomers and/or triacrylate monomers;
the monoacrylate monomer is selected from lauryl acrylate, isobornyl methacrylate and tripropylene glycol acrylate; the diacrylate monomer may be selected from the group consisting of dodecyl dimethacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, propoxylated hexanediol diacrylate and tricyclodecane dimethanol diacrylate; the triacrylate monomer is selected from trimethylolpropane triacrylate and ethoxylated trimethylolpropane triacrylate;
the photopolymerization initiator is selected from one or more of acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, carbazole compounds, diketone compounds, sulfonium boric acid compounds, diazonium salt compounds, imidazole compounds and non-imidazole compounds; the free radical polymerization initiator is selected from one or more of peroxide compounds and bisazo compounds.
Preferably, the purity of the component A, the purity of the component B and the purity of the component C are more than 95 percent, the viscosity of the composition at 25 ℃ is in the range of 17-23cP, and the surface tension of the composition is 28-36 mN/m.
A third object of the present invention is to provide an encapsulation film comprising a plurality of stacked organic layers and inorganic layers, wherein the organic layer is made of the curable film-forming composition according to any one of claims 3 to 6, and the inorganic layer is made of a material selected from the group consisting of silicon nitride, silicon oxynitride, silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, and zinc oxide.
Preferably, the inorganic layer is deposited on the surface of the object to be encapsulated by a CVD method, and the organic layer is deposited on the inorganic layer by ink-jet printing and then is cured into a film by ultraviolet.
The fourth purpose of the invention is to provide a preparation method of the packaging film, which comprises the following steps:
step S1: treatment of organic layer materials
Wherein the component A is a composition monomer L001, the component B is 2-methyl-2-acrylic acid-1, 12-dodecyl alcohol ester and 2-acrylic acid 2- ([1,1' -biphenyl ] -2-oxyl) ethyl ester, and the component C is (2,4, 6-trimethylbenzoyl) diphenyl phosphine oxide;
weighing 95g of composition monomer L001 (component A), 609g of 2-methyl-2-acrylic acid-1, 12-dodecadioyl ester, 276g of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate (component B) and 20g of (2,4, 6-trimethylbenzoyl) diphenylphosphine oxide (component C), mixing together, stirring for 80 hours at 50 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a treated organic layer material when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50;
step S2: selecting silicon nitride as an inorganic layer material;
step S3: preparation of the inorganic layer
Coating an inorganic layer material on the surface of an object to be packaged by a CVD method;
step S4: preparation of organic layer
Spraying the treated organic layer material on the surface of the base layer-free layer by using an ink-jet printer to form an organic layer, and using 100mW/cm2The ultraviolet light of 10 seconds each time is used for irradiating the organic layer to accelerate the organic layer to be hardened;
step S5: formation of encapsulation films
And depositing and coating the surface of the object to be packaged according to the alternating form of the inorganic layer and the organic layer …, and finally depositing and coating the inorganic layer and the organic layer … on the surface of the object to be packaged to obtain the packaging film.
Preferably, the organic layer has a thickness of 3 μm and the inorganic layer has a thickness of 250 nm.
The invention has the following beneficial effects:
(1) the composition comprises a composition monomer, the composition is used as an organic layer material, an inorganic layer and an organic layer are repeatedly and alternately laminated to prepare an encapsulation film of an organic light-emitting device, and the prepared encapsulation film enables the light-emitting device to be isolated from oxygen and moisture, so that the aim of protecting the organic light-emitting device is fulfilled.
(2) The packaging film provided by the invention has low Water Vapor Transmission Rate (WVTR) and good flexible property, and simultaneously has the moisture absorption degree of 9 x 10-2g/m2The application range of the packaging film is expanded due to the fact that the thickness of the organic layer and the inorganic layer is small, the prepared packaging film is very light and thin, the light transmittance is high, and the packaging film can meet different requirementsOrganic light emitting devices require visibility and aesthetics.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
A preparation method of an encapsulation film comprises the following steps:
step S1: treatment of organic layer materials
Wherein the component A is a composition monomer L001, the component B is 2-methyl-2-acrylic acid-1, 12-dodecyl alcohol ester and 2-acrylic acid 2- ([1,1' -biphenyl ] -2-oxyl) ethyl ester, and the component C is (2,4, 6-trimethylbenzoyl) diphenyl phosphine oxide;
the structural formulas of 2-methyl-2-acrylic acid-1, 12-dodeca-diol ester, 2-acrylic acid-2- ([1,1' -biphenyl ] -2-oxyl) ethyl ester and (2,4, 6-trimethylbenzoyl) diphenyl phosphine oxide are as follows:
weighing 95g of composition monomer L001 (component A), 609g of 2-methyl-2-acrylic acid-1, 12-dodecadioyl ester, 276g of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate (component B) and 20g of (2,4, 6-trimethylbenzoyl) diphenylphosphine oxide (component C), mixing together, stirring for 80 hours at 50 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a treated organic layer material when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50;
step S2: selecting silicon nitride as an inorganic layer material;
step S3: preparation of the inorganic layer
Coating an inorganic layer material on the surface of an object to be packaged by a CVD method to form an inorganic layer;
step S4: preparation of organic layer
Spraying the treated organic layer material on the surface of the inorganic layer by using an ink-jet printer to form an organic layer, and irradiating the organic layer by using 100mW/cm2 for 10 seconds each time to accelerate the organic layer to harden the organic layer;
step S5: formation of encapsulation films
And depositing and coating the surface of the object to be packaged according to the alternating form of the inorganic layer and the organic layer …, and finally depositing and coating the inorganic layer and the organic layer … inorganic layer which are deposited and coated on the surface of the object to be packaged to obtain the packaging film.
Example 2
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L001 was replaced with 200 g; and (B) component: the mass of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester is replaced by 545g, and the mass of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate is replaced by 235 g; the rest is the same as in example 1.
Example 3
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L001 is replaced by 300 g; and (B) component: the mass of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester is replaced by 475g, and the mass of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate is replaced by 205 g; the rest is the same as in example 1.
Example 4
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L001 is replaced by 400 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 405g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 175g, which was otherwise the same as in example 1.
Example 5
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L001 is replaced by 500 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 335g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 145g, which were otherwise the same as in example 1.
Example 6
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L001 is replaced by 0 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 665g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 315g, and the rest was the same as in example 1.
Example 7
A method for producing an encapsulating film, wherein in step S1, component a: the composition monomer L001 was replaced with the composition monomer L002, and the other steps were the same as in example 1. The structural formula of the composition monomer L002 is as follows:
example 8
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L002 is replaced by 200 g; and (B) component: the mass of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester is replaced by 545g, and the mass of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate is replaced by 235 g; the rest is the same as in example 7.
Example 9
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L002 is replaced by 300 g; and (B) component: the mass of 2-methyl-2-acrylic acid-1, 12-dodecadiol ester is replaced by 475g, and the mass of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate is replaced by 205 g; the rest is the same as in example 7.
Example 10
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L002 is replaced by 400 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 405g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 175g, which was otherwise the same as in example 7.
Example 11
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L002 is replaced by 500 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 335g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 145g, which were otherwise the same as in example 7.
Example 12
A method for producing an encapsulating film, wherein in step S1, component a: the mass of the composition monomer L002 is replaced by 0 g; and (B) component: the mass of 2-methyl-2-propenoic acid-1, 12-dodecanediol ester was replaced with 665g, and the mass of 2- ([1,1' -biphenyl ] -2-yloxy) ethyl 2-propenoate was replaced with 315g, and the rest was the same as in example 7.
Test example 1
The packaging films of examples 1 to 6 were tested for water vapor transmission rate with a test instrument: the manufacturer is a high-precision water vapor transmission rate tester with model number of AQUARAN2, manufactured by MOCON corporation (American Membrane health corporation); detection conditions are as follows: the temperature is 85 ℃, and the relative humidity is 85%; detection duration: 24 hours;
the encapsulation films of examples 1-6 were tested for light transmittance, and the test equipment: a light transmittance tester; detection conditions are as follows: the temperature is 40 ℃, and the relative humidity is 85 percent;
TABLE 1
| Group of | Water vapor transmission rate (g/m)2·d) | Light transmittance (%) |
| Example 1 | 4.1*10-4 | 85 |
| Example 2 | 4.4*10-4 | 86 |
| Example 3 | 4.5*10-4 | 87 |
| Example 4 | 4.5*10-4 | 86 |
| Example 5 | 4.7*10-4 | 87 |
| Example 6 | 8.0*10-3 | 86 |
Test example 2
The packaging films of examples 7 to 12 were tested for water vapor transmission rate with a test instrument: the manufacturer is a high-precision water vapor transmission rate tester with model number of AQUARAN2, manufactured by MOCON corporation (American Membrane health corporation); detection conditions are as follows: the temperature is 85 ℃, and the relative humidity is 85%; detection duration: 24 hours;
the encapsulation films of examples 7-12 were tested for light transmittance with a test instrument: a light transmittance tester; detection conditions are as follows: the temperature is 40 ℃, and the relative humidity is 85 percent;
TABLE 2
The encapsulation films prepared in examples 1 to 6 and examples 7 to 12 of the present invention were respectively tested for water vapor transmission rate by test example 1 and test example 2, wherein test example 1 is different from test example 2 in that the added component a is L001 in test example 1 and L002 in test example 2, and the comparison of the examples in table 1 shows that the water vapor transmission rate of the encapsulation film after the addition of the composition monomer L001 is significantly lower than that of the encapsulation film without the addition of the composition monomer L001; the above problems can be also explained by comparing the embodiments in table 2, and the organic light emitting device is encapsulated by the above encapsulation film, so that moisture can be effectively isolated, and the service life of the organic light emitting device can be prolonged.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. A curable film-forming composition monomer characterized by: the structural formula of the monomer of the composition is shown as a chemical general formula 1:
in the formula:
R1、R2are identical or different from each other and are each independently hydrogen or methyl; r3、R4Are the same or different from each other, and are each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted lactone groups, substituted or unsubstituted carboxyl groups, and substituted or unsubstituted glycidyl groupsA glyceryl ether group, or a hydroxyl group.
2. The monomer curable film-forming composition of claim 1, wherein: the structural formula of the monomer of the composition is as follows:
3. a curable film-forming composition characterized by: the composition consists of 9.5 to 90 mass percent of component A, 9.5 to 90 mass percent of component B and 0.5 to 10 mass percent of component C, wherein the component A is a composition monomer in claim 1, the component B is one or more acrylic acid-based compounds capable of being solidified by receiving light, and the component C is one or more photoinitiators.
4. A curable film-forming composition according to claim 3, wherein: the component B is acrylate and methacrylate; the component C is a photopolymerization initiator and/or a free radical polymerization initiator.
5. The curable film-forming composition of claim 4, wherein: the acrylate monomer comprises a monoacrylate monomer, a diacrylate monomer and/or a triacrylate monomer;
the monoacrylate monomer is selected from lauryl acrylate, isobornyl methacrylate and tripropylene glycol acrylate; the diacrylate monomer may be selected from the group consisting of dodecyl dimethacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, propoxylated hexanediol diacrylate and tricyclodecane dimethanol diacrylate; the triacrylate monomer is selected from trimethylolpropane triacrylate and ethoxylated trimethylolpropane triacrylate;
the photopolymerization initiator is selected from one or more of acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, carbazole compounds, diketone compounds, sulfonium boric acid compounds, diazonium salt compounds, imidazole compounds and non-imidazole compounds; the free radical polymerization initiator is selected from one or more of peroxide compounds and bisazo compounds.
6. A curable film-forming composition according to any one of claims 3 to 5, wherein: the purity sum of the component A, the component B and the component C is more than 95 percent, the viscosity range of the composition at 25 ℃ is 17-23cP, and the surface tension is 28-36 mN/m.
7. An encapsulation film comprising an organic layer and an inorganic layer stacked plural times, characterized in that: the organic layer material is the curable film-forming composition of any one of claims 3 to 6, and the inorganic layer material is selected from silicon nitride, silicon oxynitride, silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, and zinc oxide.
8. The packaging film of claim 7, wherein: the inorganic layer is deposited on the surface of the object to be packaged by a CVD method, and the organic layer is deposited on the inorganic layer by an ink-jet printing mode and then is cured into a film by ultraviolet.
9. The method for producing an encapsulating film according to claim 7 or 8, comprising the steps of:
step S1: treatment of organic layer materials
Wherein the component A is a composition monomer L001, the component B is 2-methyl-2-acrylic acid-1, 12-dodecyl alcohol ester and 2-acrylic acid 2- ([1,1' -biphenyl ] -2-oxyl) ethyl ester, and the component C is (2,4, 6-trimethylbenzoyl) diphenyl phosphine oxide;
weighing 95g of composition monomer L001 (component A), 609g of 2-methyl-2-acrylic acid-1, 12-dodecadioyl ester, 276g of 2- ([1,1' -biphenyl ] -2-oxyl) ethyl 2-acrylate (component B) and 20g of (2,4, 6-trimethylbenzoyl) diphenylphosphine oxide (component C), mixing together, stirring for 80 hours at 50 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a treated organic layer material when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50;
step S2: selecting silicon nitride as an inorganic layer material;
step S3: preparation of the inorganic layer
Coating an inorganic layer material on the surface of an object to be packaged by a CVD method to form an inorganic layer;
step S4: preparation of organic layer
Spraying the treated organic layer material onto the surface of the inorganic layer with an ink-jet printer to form an organic layer, and spraying with 100mW/cm2The ultraviolet light of 10 seconds each time is used for irradiating the organic layer to accelerate the organic layer to be hardened;
step S5: formation of encapsulation films
And depositing and coating the surface of the object to be packaged according to the alternating form of the inorganic layer and the organic layer …, and finally depositing and coating the inorganic layer and the organic layer … on the surface of the object to be packaged to obtain the packaging film.
10. The method for producing an encapsulating film according to claim 9, wherein: the thickness of the organic layer is 3 μm, and the thickness of the inorganic layer is 250 nm.
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| CN113402542A (en) * | 2021-05-25 | 2021-09-17 | 吉林奥来德光电材料股份有限公司 | Compound for packaging film, ink composition containing compound and film packaging structure |
| CN113402539A (en) * | 2021-06-18 | 2021-09-17 | 吉林奥来德光电材料股份有限公司 | Compound for packaging film, composition containing compound and preparation method of packaging film |
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