CN113135952B - Light-cured monomer, light-cured composition, packaging film and display device - Google Patents

Light-cured monomer, light-cured composition, packaging film and display device Download PDF

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CN113135952B
CN113135952B CN202110358383.XA CN202110358383A CN113135952B CN 113135952 B CN113135952 B CN 113135952B CN 202110358383 A CN202110358383 A CN 202110358383A CN 113135952 B CN113135952 B CN 113135952B
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substituted
unsubstituted
bis
diene
acid
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CN113135952A (en
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于哲
姜晓晨
秦翠英
朴凤昊
崔明
马晓宇
王辉
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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
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/38—Esters containing sulfur
    • 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
    • H10K50/842—Containers
    • H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants

Abstract

The invention discloses a photocuring monomer, a photocuring composition, a packaging film and a display device, belonging to the technical field of photocuring materials and film packaging, wherein the photocuring monomer has the structural general formula:
Figure DDA0003004505460000011
wherein X is CR9Or SiR10(ii) a Y is O, S, NR11Any one of (a); n is any integer from 0 to 20; r1、R2Each independently selected from any one of a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted ether group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted arylalkylene group. The photo-curing monomer provided by the embodiment of the invention can be used as an organic layer of an encapsulation film, and can effectively isolate moisture and reduce the transmittance of water vapor and gas after curing and encapsulation, so that the service life of a display device is prolonged.

Description

Photocuring monomer, photocuring composition, packaging film and display device
Technical Field
The invention relates to the technical field of photocuring materials and film packaging, in particular to a photocuring monomer, a photocuring composition, a packaging film and a display device.
Background
An OLED (Organic Light Emitting diode), also called Organic Electroluminescent Display (Organic Electroluminescent Display), is used to Display Light. The OLED is a current-type organic light emitting display device, and emits light by injection and recombination of carriers, and the intensity of light emission is proportional to the injected current. Under the action of an electric field, holes generated by an anode and electrons generated by a cathode move, are respectively injected into a hole transport layer and an electron transport layer, and migrate to a light emitting layer. When the two meet at the light emitting layer, energy excitons are generated, thereby exciting the light emitting molecules to finally generate visible light. An organic light emitting display device includes an Organic Light Emitting Device (OLED) composed of a hole injection electrode (anode), an organic light emitting layer, and an electron injection electrode (cathode). This organic light emitting device is generally provided on a glass substrate, and is covered with another substrate in order to prevent deterioration caused by inflow of moisture or oxygen from the outside. Currently, display devices including organic light emitting display devices are becoming thinner and thinner under consumer demand, and Thin Film Encapsulation (TFE) is applied to the cover of the organic light emitting devices in order to meet the demand.
Among other things, the encapsulation process may bond the glass cover plate to the display device through the use of an adhesive, for example, an adhesive with low moisture vapor transmission rate may be used between the substrate and the glass cover plate to extend the lifetime of the device. The cover glass encapsulation process is suitable for rigid devices, but it is clearly unsuitable for devices using flexible support units, such as flexible displays. Furthermore, glass cover plate packaging techniques using adhesives may not be suitable for devices where bare circuitry is present on the substrate, such as Complementary Metal Oxide Semiconductor (CMOS) microdisplays.
Disclosure of Invention
An object of an embodiment of the present invention is to provide a photo-curable monomer to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a photo-curable monomer having a general structural formula of formula 1:
Figure BDA0003004505450000021
wherein X is CR9Or SiR10；
Y is O, S, NR11Any one of (a);
n is any integer from 0 to 20;
R1、R2each independently selected from any one of a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted ether group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted arylalkylene group;
R3、R4、R5、R6each independently selected from any one of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group and hydroxyl group;
Z1and Z2Independently any of the following structures:
Figure BDA0003004505450000022
preferably, R1、R2Each independently selected from any one of a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C1-C30 ether group, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C7-C50 arylalkylene group;
R3、R4、R5、R6each independently selected from any one of hydrogen, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C1-C50 cycloalkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted 3-to 50-membered heteroaryl, substituted or unsubstituted C1-C50 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group and hydroxyl group.
Preferably, R9、R10Independently any of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, aryl and heteroaryl;
R11is any one of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, aryl and heteroaryl;
R7is hydrogen or methyl; r8Is any one of substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, and substituted or unsubstituted aralkyl; a. the1、A2Each independently selected from O, S or NR12Any one of (1), wherein R12Selected from any one of hydrogen, substituted or unsubstituted alkyl.
Preferably, R9、R10Independently any of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, C6-C30 aryl, and 4-to 30-membered heteroaryl;
R11is any one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, C6-C30 aryl, and 4-to 30-membered heteroaryl;
R8is any one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C7-C30 aralkyl; r12Selected from any one of hydrogen, substituted or unsubstituted C1-C20 alkyl.
Preferably, the structural formula of the photo-curing monomer is any one of the following structural formulas:
Figure BDA0003004505450000041
another object of the embodiments of the present invention is to provide a photocurable composition, which comprises at least one acrylic compound and at least one photo-crosslinking initiator, wherein the photocurable composition further comprises the above-mentioned photocurable monomer.
Preferably, the weight percentage of the acrylic compound in the photo-curing composition is 9.5-90%, the weight percentage of the photo-curing monomer is 9.5-90%, and the weight percentage of the photo-crosslinking initiator is 0.5-10%.
Preferably, the acrylic compound is 2-phenoxyethylacrylic acid, 2-phenoxyethyl (meth) acrylic acid, 3-phenoxypropylacrylic acid, 3-phenoxypropyl (meth) acrylic acid, 4-phenoxybutylacrylic acid, 4-phenoxybutyl (meth) acrylic acid, 5-phenoxypentylacrylic acid, 5-phenoxypentyl (meth) acrylic acid, 6-phenoxyhexylacrylic acid, 6-phenoxyhexyl (meth) acrylic acid, 7-phenoxyheptylacrylic acid, 7-phenoxyheptyl (meth) acrylic acid, 8-phenoxyoctylacrylic acid, 8-phenoxyoctyl (meth) acrylic acid, 9-phenoxynonylacrylic acid, 10-phenoxydecylacrylic acid, 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) heptylmeth) acrylic acid, 8- (phenylthio) octylacrylic acid, 9- (phenylthio) nonylacrylic acid, 9- (phenylthio) nonyl (meth) acrylic 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) butylacrylic acid, 4- ([1,1' -biphenyl ] -4-yloxy) butyl (meth) acrylic acid, 5- ([1,1' -biphenyl ] -4-yloxy) pentylacrylic acid, 5- ([1,1' -biphenyl ] -4-yloxy) pentyl (meth) acrylic acid, 6- ([1,1' -biphenyl ] -4-yloxy) hexylacrylic 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) octyl (meth) acrylic acid, 9- ([1,1' -biphenyl ] -4-yloxy) nonyl (meth) acrylic acid, 10- ([1,1' -biphenyl ] -4-yloxy) decyl (meth) acrylic 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, 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) heptylpropenoic acid, 8- ([1,1 '-biphenyl ] -4-ylthio) octylacrylic acid, 9- ([1,1' -biphenyl ] -4-ylthio) nonylacrylic acid, 10- ([1,1' -biphenyl ] -4-ylthio) decylacrylic acid, 2-hydroxy-2-phenoxyethacrylic acid, 2-hydroxy-2-phenoxyethyl (meth) acrylic acid, 2-hydroxy-2- (naphthalen-2-yloxy) ethacrylic 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) 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 (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) diacrylate, 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) 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' - (4,4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) diacrylate, 3,3' - (4,4' - (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' - (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' - (4,4' - (9H-fluorene-9), 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) diacrylate, 3,3'- (4,4' - (4,4'- (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (propane-3, 1-diene) bis (2-methacrylic acid), 2,2' - (2,2'- (4,4' - (9H-fluorene-9, 9-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene), -1 diene) diacrylic acid, 2,2' - (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' - (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' - (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) diacrylate, 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-methacrylic acid), 2,2' - (3,3' - (4,4' -oxybis (4, 1-phenylene) bis (oxy)) bis (propane-3, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) diacrylic acid, 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) diacrylic 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) 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) diacrylic 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) 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) 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) diacrylate, 2,2' - (4,4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (diene) bis (ethane-2, 1-diene) bis (2-methacrylate), 2,2' - (2,2' - (4,4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene)) 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) diacrylate, 2,2'- (2,2' - (2,2'- (4,4' - (propane-2, 2-diene) bis (4, 1-phenylene)) bis (oxy) bis (ethane-2, 1-diene)), 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) diacrylate, 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)), 1-diene) bis (2-methacrylic acid), 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' - (4,4' -oxybis (4, 1-phenylene) bis (oxy)) bis (ethane-2, 1-diene)) bis (oxy) bis (ethane-2, 1-diene) bis (oxy) bis (ethane-2, 1-diene) bis (2-methacrylate), 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) diacrylate, 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) 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, sapropenyldiacrylate, polyester urethane, epoxyacrylic acid, phenylthioethyl (meth) acrylic acid, at least one of isononyl acrylate, phenoxy-2-methyl- (meth) acrylate, phenoxybenzyl acrylate, 3-pentyloxy-2-methyl-ethyl (meth) acrylate, phenoxybenzyl alcohol, 3-phenoxy-2-stearyloxy (meth) acrylate, 2-1-naphthyloxyethyl (meth) acrylate, 2-2-naphthyloxyethyl (meth) acrylate, 2-1-ethanediol acrylate, 2-2-ethanediol acrylate, trimethylolpropane acrylate, 1, 12-dodecanediol dimethacrylate, 1, 6-ethanediol diacrylate, 1, 10-decanediol diacrylate, 1, 11-undecanediol dimethacrylate, but is not limited thereto.
Preferably, the photo-crosslinking initiator is any one of an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, and a triazine-based compound.
Preferably, the acetophenone compound is at least one of 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.
It is another object of an embodiment of the present invention to provide an encapsulation film including an inorganic layer and an organic layer partially or entirely containing the above-mentioned photocurable composition. The packaging film can be used for packaging the flexible OLED display device.
Preferably, the encapsulation film includes an inorganic layer, an organic layer, and an inorganic layer stacked in this order.
Preferably, the inorganic layer partially or entirely contains an inorganic material such as silicon nitride.
Preferably, the thickness of the encapsulation film is 0.3 to 20 μm.
Another object of an embodiment of the present invention is to provide a display device, which is packaged with the packaging film according to claim 9.
Specifically, the display device may be an organic light emitting device such as an organic light emitting diode.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the photo-curing monomer provided by the embodiment of the invention can be used as an organic layer of an encapsulation film, can effectively isolate moisture and reduce the transmittance of water vapor and gas after curing and encapsulation, prolongs the service life of a display device, and realizes the purpose of no deviation because the shrinkage stress of a photo-curing composition containing the photo-curing monomer is low after curing. In addition, the light-curing composition can enable various designs of display devices after curing and packaging, and most importantly, can enable thinning.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to 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.
Example 1
The embodiment provides a preparation method of an encapsulation film, which comprises the following steps:
s1, weighing 20g of light-cured monomer L001 (component A), 75g of 3- (naphthalene-2-yloxy) propyl (methyl) acrylic acid (component B) and 5g of 2,2' -dibutoxyacetophenone (component C), mixing together, stirring for 80h at 50 ℃ in vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a light-cured composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein, the structural formula of the photo-curing monomer L001 is as follows:
Figure BDA0003004505450000111
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the photo-curing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and using the intensity of 100mW/cm2The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
And S4, coating the inorganic layer material on the organic layer by a CVD method to form another inorganic layer, thus obtaining the packaging film.
Example 2
The embodiment provides a preparation method of an encapsulation film, which comprises the following steps:
s1, weighing 20g of light-cured monomer L002 (component A), 75g of 9- (naphthalene-2-oxyl) nonyl acrylic acid and 5g of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butandin-1-one (component C), mixing together, stirring for 80h at 50 ℃ in vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a light-cured composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein the structural formula of the photocuring monomer L002 is as follows:
Figure BDA0003004505450000121
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the photo-curing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and using the intensity of 100mW/cm2The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the packaging film.
Example 3
The embodiment provides a preparation method of an encapsulation film, which comprises the following steps:
s1, weighing 20g of photocuring monomer L003 (component A), 75g of 2- (2-phenoxyethoxy) ethyl (methyl) acrylic acid (component B) and 5g of 4-chloroacetophenone (component C), mixing, stirring for 80h at 50 ℃ in vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a photocuring composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein the structural formula of the photocuring monomer L003 is as follows:
Figure BDA0003004505450000122
and S2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the photo-curing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and using the intensity of 100mW/cm2The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the packaging film.
Example 4
The embodiment provides a preparation method of an encapsulation film, which comprises the following steps:
s1, weighing 20g of photo-curing monomer L004 (component A), 75g of 4- ([1,1' -biphenyl ] -4-yl thio) butyl acrylic acid (component B) and 5g of tert-butyl dichloroacetophenone (component C), mixing, stirring for 80h at 50 ℃ in vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a photo-curing composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein the structural formula of the photocuring monomer L004 is as follows:
Figure BDA0003004505450000131
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the photo-curing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and using the intensity of 100mW/cm2The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the packaging film.
Example 5
This example provides a method for preparing an encapsulation film, which is only different from example 1 in that step S1 is: 30g of a photocurable monomer L001 (component A), 60g of 3- (naphthalen-2-yloxy) propyl (meth) acrylic acid (component B) and 10g of 2,2' -dibutoxyacetophenone (component C) were weighed, mixed together, stirred at 50 ℃ under vacuum for 80 hours, then filtered with a syringe filter, and detected using a particle counter, and when it was detected that the number of particles having a particle size of more than 0.5 μm was not more than 50, a photocurable composition was obtained for use.
Example 6
This example provides a method for preparing an encapsulation film, which is only different from example 2 in that step S1 is: 30g of a photocurable monomer L002 (component A), 60g of 9- (naphthalen-2-yloxy) nonyl acrylic acid and 10g of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (component C) were weighed, mixed together, stirred at 50 ℃ under vacuum for 80h, then filtered with a syringe filter, checked with a particle counter, and when no more than 50 particles with a particle size of more than 0.5 μm were detected, a photocurable composition was obtained for use.
Example 7
This example provides a method for preparing an encapsulation film, which is different from example 3 only in that step S1 is: 30g of photocurable monomer L003 (component A), 60g of 2- (2-phenoxyethoxy) ethyl (meth) acrylic acid (component B) and 10g of 4-chloroacetophenone (component C) were weighed out, mixed together, stirred at 50 ℃ under vacuum for 80 hours, then filtered with a syringe filter, and detected using a particle counter, and when no more than 50 particles with a particle size of more than 0.5 μm were detected, a photocurable composition was obtained for use.
Example 8
This example provides a method for preparing an encapsulation film, which is different from example 4 only in that step S1 is: 30g of photocurable monomer L004 (component A), 60g of 4- ([1,1' -biphenyl ] -4-ylthio) butyl acrylic acid (component B) and 10g of tert-butyl dichloroacetophenone (component C) are weighed, mixed together, stirred for 80h under vacuum at 50 ℃, filtered by a syringe filter, detected by a particle counter, and when no more than 50 particles with a particle size of more than 0.5 mu m are detected, a photocurable composition is obtained for later use.
Example 9
This example provides a method for manufacturing an encapsulation film, which is different from example 1 only in that step S1 is: 9.5g of a photocurable monomer L001, 40g of 8- ([1,1 '-biphenyl ] -4-ylthio) octylacrylic acid, 30g of 8- ([1,1' -biphenyl ] -4-ylthio) octylacrylic acid, 20g of 2-2-naphthyloxyethyl (meth) acrylic acid and 0.5g of a commercially available benzophenone compound type photocrosslinking initiator were weighed out and mixed together, stirred under vacuum at 50 ℃ for 80 hours, then filtered with a syringe filter, checked with a particle counter, and when the number of particles having a particle diameter of more than 0.5 μm was detected to be not more than 50, a photocurable composition was obtained for use.
Example 10
This example provides a method for preparing an encapsulation film, which is only different from example 1 in that step S1 is: 90g of a photocurable monomer L001, 5.5g of 1, 10-decanedioldiacrylate, 4g of 1, 11-undecanedioldimethacrylate and 0.5g of a commercially available thioxanthone compound type photocrosslinking initiator were weighed out, mixed together, stirred at 50 ℃ under vacuum for 80 hours, filtered with a syringe filter, and examined with a particle counter, to obtain a photocurable composition for later use when it was detected that the number of particles having a particle size of more than 0.5 μm was not more than 50.
Example 11
This example provides a method for preparing an encapsulation film, which is only different from example 1 in that step S1 is: weighing 45g of a photo-curing monomer L001, 45g of 1, 10-decanediol diacrylate and 10g of a commercially available benzoin compound type photo-crosslinking initiator, mixing together, stirring at 50 ℃ under vacuum for 80h, then filtering with a syringe filter, detecting with a particle counter, and obtaining the photo-curing composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50.
Example 12
This example provides a method for preparing an encapsulation film, which is only different from example 1 in that step S1 is: 40g of a photocurable monomer L001, 55g of 1, 10-decanediol diacrylate and 5g of a commercially available triazine compound type photocrosslinking initiator were weighed out, mixed together, stirred at 50 ℃ under vacuum for 80 hours, then filtered with a syringe filter, checked with a particle counter, and when it was detected that the number of particles having a particle size of more than 0.5 μm was not more than 50, a photocurable composition was obtained for use.
Comparative example 1
This comparative example provides a method for producing an encapsulation film, which is different from example 1 only in that step S1 is: 98g of 3- (naphthalen-2-yloxy) propyl (meth) acrylic acid (component B) and 2g of 2,2' -dibutoxyacetophenone (component C) were weighed out, mixed together, stirred under vacuum at 50 ℃ for 80 hours, then filtered with a syringe filter, examined using a particle counter, and when it was detected that the number of particles having a particle size of more than 0.5 μm was not more than 50, a photocurable composition was obtained for use.
Performance evaluation:
first, the water vapor transmission rates of the sealing films obtained in examples 1 to 8 and comparative example 1 were measured, and the measurement results are shown in table 1. Wherein, the detecting 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: for 24 hours.
Second, the light transmittance of the sealing films prepared in examples 1 to 8 and comparative example 1 was measured, and the measurement results are shown in table 1. Wherein, the detecting instrument: a light transmittance tester; detection conditions are as follows: the temperature was 40 ℃ and the relative humidity was 85%.
TABLE 1
Figure BDA0003004505450000161
Figure BDA0003004505450000171
As can be seen from table 1, examples 1 to 8 are different from comparative example 1 in that the photocurable monomers provided in examples 1 to 8 are added, and a comparison shows that the water vapor transmission rate of the encapsulation film after the addition of the photocurable monomers provided in examples of the present invention is significantly lower than that of the encapsulation film without the addition of the photocurable monomers provided in examples of the present invention; therefore, the display device packaged by the packaging film can effectively isolate moisture, so that the service life of the display device can be prolonged.
In another embodiment of the present invention, there is also provided a display device which encapsulates the above encapsulation film. Specifically, the display device may be an organic light emitting device such as an organic light emitting diode, and may include a substrate (which may be indium tin oxide or the like), an organic light emitting diode formed on the substrate, and the encapsulation film provided in the above embodiment encapsulated on the organic light emitting diode.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (7)

1. A photo-curing monomer, wherein the general structural formula of the photo-curing monomer is formula 1:
Figure FDA0003630348090000011
wherein X is CR9；
Y is O, S, NR11Any one of (a);
n is any integer from 0 to 20;
R1、R2each independently selected from a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 ether group, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C7-C50 arylalkylene group;
R3、R4、R5、R6each independently selected from hydrogen, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C1-C50 cycloalkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted 3-to 50-membered heteroaryl, substituted or unsubstituted C1-C50 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstitutedAny one of a substituted lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, and a hydroxyl group;
Z1and Z2Independently any of the following structures:
Figure FDA0003630348090000012
R9is any one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, C6-C30 aryl, and 4-to 30-membered heteroaryl;
R11is any one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, C6-C30 aryl, and 4-to 30-membered heteroaryl;
R7is hydrogen or methyl; a. the1、A2Each independently selected from O, S or NR12Any one of (a); r8Is any one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C7-C30 aralkyl; r12Selected from any one of hydrogen, substituted or unsubstituted C1-C20 alkyl.
2. A photocurable monomer in accordance with claim 1, wherein said photocurable monomer has the formula:
Figure FDA0003630348090000021
3. a photocurable composition comprising at least one acrylic compound and at least one photocrosslinking initiator, characterized in that it further comprises a photocurable monomer according to any one of claims 1-2.
4. The photo-curable composition according to claim 3, wherein the photo-curable composition comprises 9.5 to 90 wt% of the acrylic compound, 9.5 to 90 wt% of the photo-curable monomer, and 0.5 to 10 wt% of the photo-crosslinking initiator.
5. The photocurable composition according to claim 3, wherein the photocrosslinking initiator is any one of an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, and a triazine-based compound.
6. An encapsulation film comprising an inorganic layer and an organic layer, wherein the organic layer partially or entirely contains the photocurable composition according to any one of claims 3 to 5.
7. A display device, wherein the encapsulation film according to claim 6 is encapsulated over the display device.
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