CN114685551A - Compound for packaging film, composition and packaging film - Google Patents

Compound for packaging film, composition and packaging film Download PDF

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Publication number
CN114685551A
CN114685551A CN202210233683.XA CN202210233683A CN114685551A CN 114685551 A CN114685551 A CN 114685551A CN 202210233683 A CN202210233683 A CN 202210233683A CN 114685551 A CN114685551 A CN 114685551A
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bis
diene
acid
compound
meth
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CN202210233683.XA
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CN114685551B (en
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姜晓晨
于哲
尹恩心
马晓宇
王辉
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
    • C09D143/04—Homopolymers or copolymers of monomers containing silicon
    • 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
    • H10K50/8445—Encapsulations multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers

Abstract

The invention discloses a compound for a packaging film, a composition and the packaging film. The composition comprises a compound for an encapsulation film, at least one acrylic-based compound or mixture capable of being cured by light and heat, and at least one compound or mixture capable of generating a radical or acid by light or heat. The invention relates to an organic light-emitting device packaging film with repeated coating of an inorganic layer and an organic layer, wherein an antioxidant base agent with more than two photocuring action groups is used on a packaging film composition used on the organic layer to improve the storage stability, and the low out-gas characteristic of the packaging film enables a flexible organic light-emitting device to have higher stability after the packaging film is manufactured.

Description

Compound for packaging film, composition and packaging film
Technical Field
The invention relates to the technical field of film packaging structures, in particular to a compound for a packaging film, a composition and the packaging film.
Background
An Organic Light Emitting Diode (OLED) display includes a hole injection electrode (anode), an organic light emitting layer, and an electron injection electrode (cathode). The organic light emitting device is generally attached on a substrate made of glass and covered with another substrate to prevent deterioration due to the influence of moisture or oxygen introduced from the outside. Currently, organic light emitting display devices are becoming thinner and thinner according to consumer demands, and in order to solve this problem, a Thin Film Encapsulation (TFE) structure is used.
The thin film encapsulation structure is a structure in which at least one layer of inorganic films and at least one layer of organic films are alternately stacked on top of an organic light emitting device to be formed in a display range of a substrate, so as to cover the display range and protect the organic light emitting device. The organic light emitting display device having the thin film encapsulation layer optimizes flexibility of the device together with the substrate having flexibility. In addition, the organic light emitting display device enables various designs (e.g., a folding structure) of the device, and most importantly, a thin type.
In the preparation process of the packaging film, the residual micromolecule substances in the organic layer film-forming process are easy to generate impure gas, and the data shows that the out-gas value is increased. Most of the currently used inorganic films are deposited by a method of generating plasma through sputtering (sputtering) or vapor deposition (CVD), and when more impurity gases remain in the organic films, the remaining impurity gases are released, which causes the flatness of the upper inorganic film to be reduced, which causes the WVTR to be increased, thereby adversely affecting the devices to be protected.
Disclosure of Invention
The invention provides a compound for an encapsulation film, a composition and an encapsulation film. The invention relates to an organic light-emitting device packaging film with repeated coating of an inorganic layer and an organic layer, wherein an antioxidant base agent with more than two photocuring action groups is used on a packaging film composition used on the organic layer to improve the storage stability, and the low out-gas characteristic of the packaging film enables a flexible organic light-emitting device to have higher stability after the packaging film is manufactured.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound for a packaging film, which has a structure shown in chemical formula 1:
Figure BDA0003541359100000021
wherein R is1、R4And R5Each independently selected from substituted or unsubstituted alkylene groups having a carbon number of from 1 to 20;
R2、R3is the same or different hydrogen or methyl;
in the present invention, the compound for an encapsulation film is specifically formula 101, formula 102, or formula 103.
Figure BDA0003541359100000031
A composition for film encapsulation comprising: component A, component B and component C;
wherein the component A is the compound for the packaging film;
component B comprises at least one acrylic-based compound capable of being cured by light and heat;
component C comprises at least one compound that generates radicals or acids by light or heat.
The weight percentage of each component is as follows:
the component A comprises the following components in percentage by weight: 0.01 to 5 percent;
the component B comprises the following components in percentage by weight: 85 to 99.49 percent;
the component C comprises the following components in percentage by weight: 0.5 to 10 percent.
The composition has a viscosity of 10-50 cPs at 23-27 deg.C, and is sealed in a light-tight brown bottle, and the viscosity does not change significantly when stored at 40 deg.C for 30 days.
The above composition can be made into film, and has water vapor transmission Rate (WaterVaporTransmission Rate) of 9 × 10- 2g/m2And a thin film layer in which the same or independent organic layer and inorganic layer are alternately laminated one or more times may be provided.
The inorganic layer used may be one or more of silicon nitride, silicon oxynitride, silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, and zinc oxide, and the inorganic layers of the stack may be different from one another. The thin film layer thus manufactured may be directly coated on the organic light emitting device or manufactured in a thin film form to be attached thereto.
The encapsulation part is formed directly above the organic light emitting device and the driving circuit on the substrate, and seals the organic light emitting device and the driving circuit from external damage. The structure of such encapsulation part is usually of the thin-film type, also called thin-film encapsulation layer.
Specific examples of the organic photocurable acrylic monomer (component B) usable together with the compound of chemical formula 1 are: 2-phenoxyethylacrylic acid, 2-phenoxyethyl (meth) acrylic acid, 3-phenoxypropylacrylic acid, 3-phenoxypropyl (meth) acrylic acid, 4-phenoxybutylacrylic acid, 4-phenoxybutyl (meth) acrylic acid, 5-phenoxypentylacrylic acid, 5-phenoxypentyl (meth) acrylic acid, 6-phenoxyhexylacrylic acid, 6-phenoxyhexyl (meth) acrylic acid, 7-phenoxyheptylacrylic acid, 7-phenoxyheptyl (meth) acrylic acid, 8-phenoxyoctylacrylic acid, 8-phenoxyoctyl (meth) acrylic acid, 9-phenoxynonylacrylic acid, 9-phenoxynonyl (meth) acrylic acid, 10-phenoxydecylacrylic acid, 10-phenoxydecyl (meth) acrylic acid, 2- (phenylthio) ethacrylic acid, 2- (phenylthio) ethyl (meth) acrylic acid, 3- (phenylthio) propylacrylic acid, 3- (phenylthio) propyl (meth) acrylic acid, 4- (phenylthio) butylacrylic acid, 4- (phenylthio) butyl (meth) acrylic acid, 5- (phenylthio) pentylacrylic acid, 5- (phenylthio) pentyl (meth) acrylic acid, 6- (phenylthio) hexylacrylic acid, 6- (phenylthio) hexyl (meth) acrylic acid, 7- (phenylthio) heptylacrylic acid, 7- (phenylthio) heptylpropyl (meth) acrylic acid, 8- (phenylthio) octylacrylic acid, 8- (phenylthio) octyl (meth) acrylic acid, 9- (phenylthio) nonylacrylic acid, 10- (phenylthio) decylacrylic acid, 10- (phenylthio) decyl (meth) acrylic acid, 2- (naphthalen-2-yloxy) ethacrylic acid, 2- (naphthalen-2-yloxy) ethyl (meth) acrylic acid, 3- (naphthalen-2-yloxy) propylacrylic acid, 3- (naphthalen-2-yloxy) propyl (meth) acrylic acid, 4- (naphthalen-2-yloxy) butylacrylic acid, 4- (naphthalen-2-yloxy) butyl (meth) acrylic acid, 5- (naphthalen-2-yloxy) pentylacrylic acid, 5- (naphthalen-2-yloxy) pentyl (meth) acrylic acid, 6- (naphthalen-2-yloxy) hexylacrylic acid, 6- (naphthalen-2-yloxy) hexyl (meth) acrylic acid, 7- (naphthalen-2-yloxy) heptylacrylic acid, 8- (naphthalen-2-yloxy) octylacrylic acid, 9- (naphthalen-2-yloxy) nonylacrylic acid, 9- (naphthalen-2-yloxy) nonyl (meth) acrylic acid, 10- (naphthalen-2-yloxy) decylacrylic acid, 10- (naphthalen-2-yloxy) decyl (meth) acrylic acid, 2- (naphthalen-2-ylthio) ethacrylic acid, 2- (naphthalen-2-ylthio) ethyl (meth) acrylic acid, 3- (naphthalen-2-ylthio) propylacrylic acid, 3- (naphthalen-2-ylthio) propyl (meth) acrylic acid, 4- (naphthalen-2-ylthio) butylacrylic acid, 4- (naphthalen-2-ylthio) butyl (meth) acrylic acid, 5- (naphthalen-2-ylthio) pentylacrylic acid, 5- (naphthalen-2-ylthio) pentyl (meth) acrylic acid, 6- (naphthalen-2-ylthio) hexylacrylic acid, 6- (naphthalen-2-ylthio) hexyl (meth) acrylic acid, 7- (naphthalen-2-ylthio) heptyl, acrylic acid, 7- (naphthalen-2-ylthio) heptyl (meth) acrylic acid, 8- (naphthalen-2-ylthio) octylacrylic acid, 8- (naphthalen-2-ylthio) octyl (meth) acrylic acid, 9- (naphthalen-2-ylthio) nonylacrylic acid, 9- (naphthalen-2-ylthio) nonyl (meth) acrylic acid, 10- (naphthalen-2-ylthio) decylacrylic acid, 10- (naphthalen-2-ylthio) decyl (meth) acrylic acid, 2- ([1, 1 '-biphenyl ] -4-yloxy) ethacrylic acid, 2- ([1, 1' -biphenyl ] -4-yloxy) ethyl (meth) acrylic acid, 3- ([1, 1 '-biphenyl ] -4-yloxy) propylacrylic acid, 3- ([1, 1' -biphenyl ] -4-yloxy) propyl (meth) acrylic acid, 4- ([1, 1 '-biphenyl ] -4-yloxy) butyl acrylic acid, 4- ([1, 1' -biphenyl ] -4-yloxy) butyl (meth) acrylic acid, 5- ([1, 1 '-biphenyl ] -4-yloxy) pentyl (meth) acrylic acid, 6- ([1, 1' -biphenyl ] -4-yloxy) hexyl (meth) acrylic acid
Acrylic acid, 6- ([1, 1' -biphenyl ] -4-yloxy) hexyl (meth) acrylic acid, 7- ([1, 1' -biphenyl ] -4-yloxy) heptylacrylic acid, 7- ([1, 1' -biphenyl ] -4-yloxy) heptyl (meth) acrylic acid, 8- ([1, 1' -biphenyl ] -4-yloxy) octylacrylic acid, 8- ([1, 1' -biphenyl ] -4-yloxy) octyl (meth) acrylic acid, 9- ([1, 1' -biphenyl ] -4-yloxy) nonylacrylic acid, 9- ([1, 1' -biphenyl ] -4-yloxy) nonyl (meth) acrylic acid, 10- ([1, 1 '-biphenyl ] -4-yloxy) decylacrylic acid, 2- ([1, 1' -biphenyl ] -4-ylthio) ethacrylic acid, 2- ([1, 1 '-biphenyl ] -4-ylthio) ethyl (meth) acrylic acid, 3- ([1, 1' -biphenyl ] -4-ylthio) propylacrylic acid, 3- ([1, 1 '-biphenyl ] -4-ylthio) propyl (meth) acrylic acid, 4- ([1, 1' -biphenyl ] -4-ylthio) butylacrylic acid, 4- ([1, 1 '-biphenyl ] -4-ylthio) butyl (meth) acrylic acid, 5- ([1, 1' -biphenyl ] -4-ylthio) pentylacrylic acid, 5- ([1, 1 '-biphenyl ] -4-ylthio) pentyl (meth) acrylic acid, 6- ([1, 1' -biphenyl ] -4-ylthio) hexylacrylic acid, 6- ([1, 1 '-biphenyl ] -4-ylthio) hexyl (meth) acrylic acid, 7- ([1, 1' -biphenyl ] -4-ylthio) heptylacrylic acid, 7- ([1, 1 '-biphenyl ] -4-ylthio) heptylmeth) acrylic acid, 8- ([1, 1' -biphenyl ] -4-ylthio) octylacrylic acid, 8- ([1, 1' -biphenyl ] -4-ylthio) octyl (meth) acrylic acid, 9- ([1, 1' -biphenyl ] -4-ylthio) nonyl (meth) acrylic acid, 10- ([1, 1' -biphenyl ] -4-ylthio) decyl (meth) acrylic acid, 2-hydroxy-2-phenoxyethyl (meth) acrylic acid, 2-hydroxy-2- (naphthalen-2-yloxy) ethyl acrylic acid, 2-hydroxy-2- (naphthalen-2-yloxy) ethyl (meth) acrylic acid, 2- ([1, 1 '-biphenyl ] -4-yloxy) ethacrylic acid, 2- ([1, 1' -biphenyl ] -4-yloxy) ethyl (meth) acrylic acid, 2- (2-phenoxyethoxy) ethacrylic acid, 2- (2-phenoxyethoxy) ethyl (meth) acrylic acid, 2- (phenoxymethoxy) ethacrylic acid, 2- (phenoxymethoxy) ethyl (meth) acrylic acid, 2- (([1, 1 '-biphenyl ] -4-yloxy) methoxy) ethacrylic acid, 2- (([1, 1' -biphenyl ] -4-yloxy) methoxy) ethyl (meth) acrylic acid, 2- ((naphthalen-2-yloxy) methoxy) ethacrylic acid, 2- ((naphthalen-2-yloxy) methoxy) ethyl (meth) acrylic acid, 2- ((phenylthio) methoxy) ethacrylic acid, 2- ((phenylthio) methoxy) ethyl (meth) acrylic acid, 2- ((naphthalen-2-ylthio) methoxy) ethacrylic acid, 2- ((naphthalen-2-ylthio) methoxy) ethyl (meth) acrylic acid, 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 3, 3'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) diacrylate, 3, 3'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 3, 3' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (diene) bis (propane-3, 1-diene) diacrylic acid, 3, 3' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (diene) bis (propane-3, 1-diene) bis (2-methacrylic acid), 2, 2' - (4), 4'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 3, 3'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) diacrylate, 3, 3'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (4, 4' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 3, 3' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) diacrylic acid, 3, 3' - (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, -1-diene) diacrylic acid, 2, 2'- (4, 4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, -1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' - (9H-fluorene-9), 9-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, -1-diene) diacrylic acid, 2, 2'- (4, 4') - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, -1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' -oxybis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene) diacrylic acid, 2, 2'- (4, 4' -oxybis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' -oxybis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (4, 4' -oxybis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' -thiobis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (4, 4' -thiobis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2'- (4, 4' -thiobis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (4, 4' -thiobis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) bis (2-methacrylate), 2, 2'- (3, 3' - (4, 4 '-oxybis (4, 1-phenylene) bis (oxy)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2' - (3, 3'- (4, 4' -oxybis (4, 1-phenylene) bis (oxy)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (3, 3' - (4, 4' -thiobis (4, 1-phenylene) bis (oxy)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2' - (3, 3' - (4, 4' -thiobis (4, 1-phenylene) bis (oxy)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (3, 3' - (4, 4' -oxybis (4, 1-phenylene) bis (diene)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (3, 3' - (4, 4 '-oxybis (4, 1-phenylene) bis (diene)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (3, 3'- (4, 4' -thiobis (4, 1-phenylene) bis (diene)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (2, 2' - (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (2, 2'- (4, 4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene)), 2, 2' - (2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid, 2, 2' - (2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene)) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (2, 2'- (2, 2' - (4, 4'- (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid, 2, 2' - (2, 2'- (2, 2' - (4, 4 '-oxybis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylate, 2, 2' - (2, 2'- (2, 2' - (2, 2' - (4, 4' -oxybis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylate), 2, 2' - (2, 2' - (4, 4' -thiobis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (2, 2' - (2, 2' - (4, 4' -thiobis (4), 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), 2, 2' - (2, 2' - (2, 2' - (4, 4' -thiobis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 2, 2' - (2, 2' - (4, 4' -thiobis (4, 1-phenylene) bis (diene)) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylic acid), polyester urethane diacrylate, acrylic diacrylate, polyester urethane, epoxy acrylic acid, phenylthioethyl (meth) acrylic acid, isononyl acrylate, phenoxy-2-methyl- (meth) acrylic acid ethyl ester, phenoxybenzyl acrylate, 3-pentyloxy-2-methyl-ethyl (meth) acrylic acid, phenoxybenzyl alcohol, 3-phenoxy-2-stearyloxy (meth) acrylate, 2-1-naphthyloxyethyl (meth) acrylic acid, 2-2-naphthyloxyethyl (meth) acrylic acid, 2-1-ethanediol acrylate or 2-2-ethanediol acrylate, trimethylolpropane acrylate, 1, 12-dodecanediol dimethacrylate, 1, 6-ethanediol diacrylate, 1, 10-decanediol diacrylate, 1, 11-undecanediol dimethacrylate, etc., and these may be used alone or in combination of two or more.
Photoinitiator(s)
The initiator may be a photopolymerization initiator, a radical polymerization initiator, or a combination thereof.
As the photopolymerization initiator, for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds and triazine compounds, which are used as initiators for photosensitive resin compositions, are generally used.
Examples of compounds of the above acetophenone are: 2, 2' -diethoxyacetophenone, 2, 2' -dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, p-butyltrichloroacetophenone, t-butyldichloroacetophenone, 4-chloroacetophenone, 2, 2' -dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butandin-1-one, and the like.
Examples of compounds of the above-mentioned benzophenones are: benzophenone, benzoyl benzoate, methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4, 4' -bis (dimethylamino) benzophenone, 4, 4 and ' -bis (diethylamino) benzophenone, 4, 4' -dimethylamino benzophenone, 4, 4' -dichlorobenzophenone, 3, 3' -dimethyl-2-methoxybenzophenone and the like.
Examples of the above-mentioned thioxanthone-based compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-diisocyanate. And propylthioxanthone and 2-chlorothioxanthone.
Examples of the above benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.
Examples of the above-mentioned triazine compounds include 2, 4, 6-trichloro-s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (3', 4' -dimethoxystyryl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4' -methoxynaphthyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-biphenyl-4, 6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphthalene-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy naphthalene-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2-4-trichloromethyl (piperidine) -6-triazine, 2-4-trichloromethyl (4' -methoxy styrene) -6-triazine and the like.
As the photopolymerization initiator, a carbazolyl compound, a diketone compound, a boric acid sulfonic acid compound, a diazo compound, an imidazolyl compound or a biimidazole compound can be used.
The radical polymerization initiator may be a peroxide-based compound, an azobis-based compound, or the like.
Examples of the above peroxide-based compound include ketone peroxides such as methyl ethyl ketone peroxide, diacyl peroxide, hydroperoxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide and acetylacetone peroxide.
Diacyl peroxides include, for example, isobutyryl peroxide, 2, 4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide and bis 3, 5, 5-trimethylhexanoyl peroxide;
hydroperoxides include, for example, 2, 4, 4, -trimethylpentyl-2-hydroperoxide, diisopropylbenzene hydroperoxide, cumene peroxide and tert-butyl hydroperoxide; dicumyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, 1, 3-bis (t-butoxyisopropyl) benzene, n-butyl-peroxyvalerate dialkyl peroxides, hydroperoxides such as 2, 4, 4-trimethylpentylperoxyphenoxy acetate, diisopropylbenzene hydroperoxide, t-butylperoxybenzoate and di-t-butylperoxytrimethyl adipate; di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, bis-4-tert-butylcyclohexyl peroxydicarbonate, diisopropyl peroxydicarbonate, acetylcyclohexylsulfonyl peroxide, tert-butyl peroxyarylcarbonate, for example-butyl peroxyarylcarbonate.
Examples of the above-mentioned azobis-based compound include 1, 1 '-azobiscyclohexane-1-carbonitrile, 2, 2' -azobis (2, 4-dimethylvaleronitrile), 2, 2 '-azobis (methyl isobutyrate), 2, 2' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), α, α '-azobis (isobutyronitrile) and 4, 4' -azobis (4-cyanovaleric acid).
The initiator may be used with a photosensitizer that causes a chemical reaction by absorbing light and then exciting the light to transfer its energy.
Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like.
The mass of the initiator (component B) is 0.5 to 10% of the mass of the composition, based on the total amount of the film-encapsulating composition. When the initiator is within the above range, curing may sufficiently occur during exposure in the film forming process to obtain excellent reliability, and the problem of transmittance reduction due to unreacted initiator may be prevented, but the present invention is not limited thereto.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 is a graph showing the storage stability of a photocurable composition.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Production example 1
Production of Compound 1 of chemical formula 2
166g of ethyl 2- ((3- (dimethyl (2- (propionyloxy) ethyl) silyl) -5- (hydroxymethyl) phenyl) dimethylsilyl) methacrylate (chemical formula 6) and 700ml of toluene were charged in a 2L reaction flask, 161g of 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid (chemical formula 7) and 1.2g of sulfuric acid were further added, a water separator was erected, temperature was raised to reflux and stirring was continued for 6 hours, and neutralization was performed with an alkaline solution, whereby 106.3g of Compound 1 represented by chemical formula 2 was prepared.
Figure BDA0003541359100000131
The compound 1 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 90%.
Mass spectrum: calculated value 709.08; the test value was 708.33.
Elemental analysis:
the calculated values are: 67.76 percent of C; 8.53 percent of H; 15.79 percent of O; 7.92 percent of Si.
The test values are: 68.83 percent of C; 8.96 percent of H; 15.22 percent of O; 6.99 percent of Si.
Production example 2
Production of Compound 2 of chemical formula 3
149g of ((5- (hydroxymethyl) -1, 3-phenylene) bis (dimethylsilyl)) bis (methylene) diacrylate (chemical formula 8) and 700ml of toluene were charged in a 2L reaction flask, 169g of 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) -2-methylpropanoic acid (chemical formula 9) and 1.2g of sulfuric acid were added, a water separator was set up, temperature was raised to reflux and stirring was continued for 6 hours, and neutralization was performed with a basic solution, whereby 97.3g of Compound 2 having chemical formula 3 was prepared.
Figure BDA0003541359100000141
HPLC purity: greater than 90%.
Mass spectrum: calculated value 667.00; the test value was 665.98.
Elemental analysis:
the calculated values are: 66.63 percent of C; 8.16 percent of H; 16.79 percent of O; 8.42 percent of Si.
The test values are: 67.68 percent of C; 8.56 percent of H; 15.89 percent of O; 7.84 percent of Si.
Production example 3
Production of Compound 3 of chemical formula 4
In a 2L reaction flask were charged 181g of ((5- (hydroxymethyl) -1, 3-phenylene) bis (dimethylsilyl) bis (propane-1, 2-diacyl) bis (2-methacrylate) (chemical formula 10) and 700ml of toluene, 161g of 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionic acid (chemical formula 7) and 1.2g of sulfuric acid were further added, a water separator was erected, and the mixture was heated to reflux and continuously stirred for 6 hours, and neutralized with a basic solution, to thereby prepare 101.1g of Compound 3 having chemical formula 4.
Figure BDA0003541359100000151
HPLC purity: greater than 90%.
Mass spectrum: calculated value 652.79; the test value was 651.68.
Elemental analysis:
the calculated values are: 68.44 percent of C; 8.75 percent of H; 15.19 percent of O; 7.62 percent of Si.
The test values are: 69.53 percent of C; 9.56 percent of H; 14.21 percent of O; 6.70 percent of Si.
Production example 4
Production of Compound 4 of chemical formula 5
50g of 4- (aminomethyl) -2, 6-di-tert-butylphenol (chemical formula 11) and 17g of acrylic acid (chemical formula 12) were dissolved in 200g of toluene, and after 2g of sulfuric acid was added, it was heated to 110 ℃ and stirred for 6 hours. The temperature was cooled to room temperature, 2 washes were performed with 500g of 10 wt% NaOH aqueous solution, then 2 washes were performed with 500g of distilled water, and the organic layer was distilled under reduced pressure to obtain 54g of Compound 4 of chemical formula 5.
Figure BDA0003541359100000152
Examples 1 to 3 and comparative examples 1 to 3
Silicon nitride was deposited as a moisture barrier using plasma chemical vapor deposition on a pretreated 6cm x 6cm PEN (TEONEX, Tenjin dupont film) substrate. Plasma was generated using a 13.56MHz RF match box in the inductively coupled plasma method, Trisilylamine (TSA) at a flow rate of 20sccm and ammonia at a flow rate of 60sccm were supplied into the reactor as a precursor and a reaction gas for deposition, and argon at a flow rate of 200sccm was supplied as a carrier gas. After the gas in the reactor was sufficiently saturated, ammonia plasma was discharged at a pressure of 5Pa for deposition for 12 minutes to form a silicon nitride film having a thickness of 250 nm. The formation of a silicon nitride film having a thickness of 250nm was confirmed by SEM (scanning electron microscope).
The photocurable compositions required to form the organic films were matched in the proportions shown in the examples and comparative examples in Table 1 below, and the photocurable compositions were coated with 100mW/cm2UV curing was carried out by irradiation for 10 seconds, thereby forming a cured coating film having a thickness of 3 μm. A high-pressure mercury lamp was used as an exposure light source, and a silicon nitride thin film having a thickness of 250nm was formed on the formed organic film by the same method as the above-described inorganic film coating method.
The compounds were stirred in the autoclave for 30 minutes and then filtered through a 0.45um Teflon filter having the composition shown in Table 1.
TABLE 1
Figure BDA0003541359100000161
(1) Outgas measurement
Each of the compositions of examples 1-3 and comparative examples 1-3 was coated with a 5 μm thick coating on 10cm by 10cm glass using MA-6 (R)
Figure BDA0003541359100000173
Co.)) at 200mJ/cm in a nitrogen atmosphere2The organic layer after curing is obtained by irradiation with the exposure of (1). After preparation, the glass substrates were cut into 6 samples with dimensions of 1cm x3 cm. Outgas was collected at 120 ℃ for 30 minutes using JAI's JTD-505 III apparatus. After the samples were measured by QP2020GC/MS of Shimadzu, a calibration curve was plotted, and the collected samples Outgas were analyzed and shown in Table 2.
TABLE 2
Figure BDA0003541359100000171
As shown in Table 2, it can be seen from the data of out-gas that the data of out-gas is the highest with the antioxidant having no photocuring group (acrylate group), and the data of out-gas is the lowest with the antioxidant having 2 photocuring groups, which is similar to the data of out-gas of the mixture without the antioxidant. Therefore, whether the antioxidant contains the photocuring group has certain influence on the out-gas data of the organic layer of the packaging material.
(2) WVTR test
As shown in table 3, an inorganic film (250 nm)/an organic film (3 μm)/an inorganic film (250nm) was formed on a substrate, and the moisture permeability of the encapsulating film was measured using a moisture permeability meter (AQUARAN2, MOCON corporation). Measurements were made at 37.8 ℃ and 100% relative humidity for 24 hours.
TABLE 3
Figure BDA0003541359100000172
Figure BDA0003541359100000181
As shown in Table 3, in comparative example 5, when the antioxidant does not have a photocurable group, the WVTR value is the largest, the WVTR value of comparative example 4 is relatively large, and the WVTR values of comparative example 6 and examples 3, 4 and 5 are low and close to each other.
As can be seen from the comparison between table 2 and table 3, the organic layer out-gas data and the encapsulation film WVTR data have a certain corresponding relationship, i.e., when the out-gas value is high, the corresponding WVTR value is also high, and the screen life will be short; when the out-gas value is low, the corresponding WVTR value is also low, and the service life of the screen is longer.
(3) Storage stability test
The compositions of examples 1, 2 and comparative examples 1 to 3 as photocurable compositions were sealed in light-tight brown bottles and stored at 25 ℃, and the viscosity was measured periodically and is shown in table 4 and fig. 1.
TABLE 4
Figure BDA0003541359100000182
Figure BDA0003541359100000191
As shown in table 4 and fig. 1, when storage stability was compared by measuring the change in viscosity while storing at 25 ℃ under the same conditions, comparative example 3, which did not contain an antioxidant, showed a rapid increase in viscosity after 5 days, and it was confirmed that the composition without the antioxidant was likely to be deteriorated and was difficult to store for a long period. The viscosity of the antioxidant-containing compositions of examples 1 and 2 and comparative examples 1 and 2 was almost unchanged after 30 days of storage, and it was confirmed that the antioxidant-containing compositions could be stored for a long period of time under appropriate environments.
In summary, when the compounds 1 and 2 having two photo-curable groups are used as antioxidants, the Outgas of the organic layer and the WVTR data of the encapsulating film are not adversely affected, while when a general antioxidant is added, the Outgas of the organic layer and the WVTR of the encapsulating film are both increased, and the storage stability is very good when the antioxidant is added compared with that when the antioxidant is not added. Therefore, the addition of the antioxidant can well improve the stability of the product without affecting other properties.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (6)

1. A compound for an encapsulation film, characterized by having a structure represented by chemical formula 1:
Figure FDA0003541359090000011
wherein R is1、R4And R5Each independently selected from substituted or unsubstituted alkylene groups having a carbon number of from 1 to 20;
R2and R3Each independently selected from hydrogen or methyl.
2. The compound for encapsulation film according to claim 1, wherein the chemical formula 1 is selected from the following structures:
Figure FDA0003541359090000012
Figure FDA0003541359090000021
3. a composition for an encapsulating film, comprising: component A, component B and component C
Wherein the component A is the compound for an encapsulating film according to claim 1 or 2;
the component B comprises at least one acrylic-based compound capable of being cured by light and heat;
the component C comprises at least one compound which generates radicals or acids by light or heat.
4. The composition for an encapsulation film according to claim 3, comprising, in weight percent: 0.01 to 5 percent of component A; component B85-99.49% and component C0.5-10%.
5. A composition for an encapsulation film according to claim 3, wherein the compound or mixture generating a radical or acid by light or heat is a photopolymerization initiator, a radical polymerization initiator or a combination thereof.
6. An encapsulating film comprising an inorganic layer and an organic layer alternately arranged in this order, wherein the organic layer comprises the composition for film encapsulation according to any one of claims 3 to 5.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110357916A (en) * 2019-07-23 2019-10-22 吉林奥来德光电材料股份有限公司 Packaging film compound and combinations thereof and film and organic luminescent device and packaging method
CN112898330A (en) * 2020-07-28 2021-06-04 吉林奥来德光电材料股份有限公司 Compound for packaging organic light-emitting device and preparation method and application thereof
CN113801260A (en) * 2021-08-04 2021-12-17 吉林奥来德光电材料股份有限公司 Compound for film packaging, photocuring composition and film packaging layer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110357916A (en) * 2019-07-23 2019-10-22 吉林奥来德光电材料股份有限公司 Packaging film compound and combinations thereof and film and organic luminescent device and packaging method
CN112898330A (en) * 2020-07-28 2021-06-04 吉林奥来德光电材料股份有限公司 Compound for packaging organic light-emitting device and preparation method and application thereof
CN113801260A (en) * 2021-08-04 2021-12-17 吉林奥来德光电材料股份有限公司 Compound for film packaging, photocuring composition and film packaging layer

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