CN113801260A - Compound for film packaging, photocuring composition and film packaging layer - Google Patents

Compound for film packaging, photocuring composition and film packaging layer Download PDF

Info

Publication number
CN113801260A
CN113801260A CN202110892471.8A CN202110892471A CN113801260A CN 113801260 A CN113801260 A CN 113801260A CN 202110892471 A CN202110892471 A CN 202110892471A CN 113801260 A CN113801260 A CN 113801260A
Authority
CN
China
Prior art keywords
bis
diene
compound
acid
film encapsulation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN202110892471.8A
Other languages
Chinese (zh)
Inventor
姜晓晨
于哲
尹恩心
马晓宇
王辉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jilin Optical and Electronic Materials Co Ltd
Original Assignee
Jilin Optical and Electronic Materials Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jilin Optical and Electronic Materials Co Ltd filed Critical Jilin Optical and Electronic Materials Co Ltd
Priority to CN202110892471.8A priority Critical patent/CN113801260A/en
Publication of CN113801260A publication Critical patent/CN113801260A/en
Withdrawn legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04Acids; Metal salts or ammonium salts thereof
    • C08F220/06Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers 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
    • C08F230/04Copolymers 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
    • C08F230/08Copolymers 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
    • C08F230/085Copolymers 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
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/80Constructional details
    • H10K50/84Passivation; Containers; Encapsulations
    • H10K50/844Encapsulations
    • H10K50/8445Encapsulations multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a compound for film packaging, a photocuring composition and a film packaging layer, and belongs to the technical field of film packaging structures, wherein the compound structure is shown as a chemical formula 1, and the photocuring composition comprises 0.1-5% of a component A, 85-99.4% of a component B and 0.5-10% of a component C. The film-encapsulating layer includes an organic layer and an inorganic layer, and the organic layer includes a photocurable composition for film encapsulation. The silicon-containing monomer prepared by the invention contains an aromatic ring and a Si atom of a rigid group in a molecular structure, and has better heat resistance and transparency, and lower water vapor transmission rate and oxygen transmission rate compared with an ink composition without a benzene ring and a silicon atom. When the film is used for packaging the OLED device, water and oxygen can be effectively blocked, the reliability is improved, and the service life of the OLED device is further prolonged.

Description

Compound for film packaging, photocuring composition and film packaging layer
Technical Field
The invention relates to the technical field of thin film packaging structures, in particular to a compound for thin film packaging, a photocuring composition and a thin film packaging layer.
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.
Therefore, how to provide a thin film encapsulation compound is a problem that needs to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention provides a compound for film encapsulation, a photocurable composition and a film encapsulation layer.
In order to achieve the purpose, the invention adopts the following technical scheme:
a compound for thin film encapsulation, which has a structure represented by chemical formula 1:
Figure BDA0003196669590000021
wherein, R is1、R2、R6Independently selected from the same or different hydrogen, C1-C20Substituted or unsubstituted alkyl of, C6-C30Substituted or unsubstituted aryl of (a);
the R is3、R4、R5Independently selected from the same or different C1-C20Substituted or unsubstituted alkylene of (A), C6-C30Substituted or unsubstituted arylene of (a);
the R is7Is hydrogen or methyl;
said X1、X2Is one of O, S or NH, wherein X2The hydrogen in the NH represented by (C) may be replaced by1To C12Alkyl or C6-C20Aryl substitution.
Preferably, said R is1Is C4An alkyl group;
the R is2Is C4An alkyl group;
the R is3Is C2-C3An alkyl group;
the R is4Is C2An alkyl group;
the R is5Is C2An alkyl group;
the R is6Is C1-C3An alkyl group;
the R is7Is H or C1An alkyl group;
said X1Is O or NH;
said X2Is O.
Has the advantages that: the compound of chemical formula 1 of the present invention can be used for preparing a compound having oneOne or more other light and heat curable acryl based compounds or mixtures and a composition having one or more light or heat generating free radicals and acid based compounds or mixtures, which composition, when formed into a film, has a water vapor Transmission Rate (WaterVapor Transmission Rate) of 9X 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 film layer prepared in this way can be directly coated on the organic light emitting device or prepared in a film form and attached on the organic light emitting device.
The invention provides a photocuring composition for film encapsulation, which comprises 0.1-5% of a component A, 85-99.4% of a component B and 0.5-10% of a component C;
wherein the content of the first and second substances,
the component A comprises an antioxidant containing an acrylate structure shown in a chemical formula 1;
the component B comprises acrylic monomers;
the component C comprises a photoinitiator.
Preferably, the acrylic monomer is an organic photocurable acrylic monomer, and specifically includes: 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) 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) 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) diacrylic acid, 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' - (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' - (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, sapropenediacrylic acid, polyester urethane, epoxyacrylic acid, phenylthioethyl (meth) acrylic acid, isononyl acrylate, phenoxy-2-methyl- (meth) acrylate 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-ethylene glycol acrylate or 2-2-ethylene glycol acrylate, trimethylolpropane acrylate, 1, 12-dodecanediol dimethacrylate, 1, 6-ethanedioic acid ester, 1, 10-decanediol diacrylate, 1, 11-undecanediol dimethacrylate, or mixtures thereof.
Preferably, the photoinitiator includes a photopolymerization initiator and/or a radical polymerization initiator.
Preferably, the photopolymerization initiator includes one or more of an initiator used in the photosensitive resin composition, a carbazolyl compound, a diketone compound, a boric acid sulfonic acid compound, a diazo compound, and an imidazolyl compound or a bisimidazolyl compound. The initiator used in the photosensitive resin composition comprises one or a mixture of a plurality of acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds and triazine compounds.
Preferably, the acetophenone compound includes 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.
The benzophenone-series compound includes 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.
The thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, and 2, 4-diisocyanate. And propylthioxanthone and 2-chlorothioxanthone.
Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.
The above 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.
Preferably, the radical polymerization initiator includes a peroxide-based compound and/or an azobis-based compound.
The peroxy-based compound includes ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide and acetylacetone peroxide. Diacyl peroxides such as isobutyryl peroxide, 2, 4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide and bis 3, 5, 5-trimethylhexanoyl peroxide; hydroperoxides such as 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.
The azobis-based compound includes 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).
Preferably, the component C further includes a photosensitizer which causes a chemical reaction by absorbing light and then exciting light to transmit its energy.
The photosensitizer comprises tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, dipentaerythritol tetra-3-mercaptopropionate and the like.
Has the advantages that: the mass of the initiator is 0.5 to 10% of the mass of the composition based on the total amount of the photosensitive resin 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.
A thin film encapsulation layer comprising an organic layer and an inorganic layer, the inorganic layer being thicker in thickness relation to the organic layer than the inorganic layer, the organic layer comprising the photocurable composition for thin film encapsulation as claimed in any one of claims 3 to 7.
The inorganic layer includes one of calcium oxide, aluminum oxide, titanium oxide, indium oxide, tin oxide, silicon nitride, silicon oxynitride, aluminum nitride, and zirconium oxide.
Preferably, the thickness of the thin film packaging layer is 0.3-20 μm.
Preferably, the preparation method of the thin film encapsulation layer comprises the following steps:
the photocurable composition was coated and used at 100mW/cm2UV curing was performed by irradiation for 10 seconds to form a cured coating film. A high-pressure mercury lamp was used as an exposure light source, and a thin film having a thickness of 250nm was formed on the formed organic film by the same method as the above-mentioned inorganic film coating method.
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.
(1) Organic layer
The organic layer may be used on a monomer group having one or more photo-curable or thermal-curable groups, in addition to the compound of formula 1. The monomer or monomers, the photo radical generator, and the thermal and photo acid generator are mixed, coated by ink jet, electron spray, electron irradiation, etc., and then molded by ultraviolet irradiation or thermal curing.
(2) Inorganic layer
The inorganic layer may be formed by sputtering, Chemical Vapor Deposition (CVD), Atomic Layer Deposition (ALD), Ion Beam Assisted Deposition (IBAD) of an oxide or nitride of a metal.
(3) Inorganic layer coating and coating film formation
The above inorganic substances were deposited as moisture-proof layers on pretreated 6cm × 6cm PEN (TEONEX, Tenjin Dupont Film) substrates by plasma chemical vapor deposition. Plasma was generated using a 13.56mhz rf match box in the inductively coupled plasma method, Trisilylamine (TSA) at a flow rate of 20 seem and ammonia at a flow rate of 60 seem were supplied into the reactor as a precursor and a reaction gas for deposition, and argon at a flow rate of 200 seem 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.
According to the technical scheme, compared with the prior art, the silicon-containing monomer prepared by the invention contains an aromatic ring containing a rigid group and a Si atom in a molecular structure, has better heat resistance and transparency, lower water vapor transmission rate and lower oxygen transmission rate compared with an ink composition without a benzene ring and a silicon atom, and reduces excessive shrinkage volume generated by curing of the organic ink composition.
Drawings
FIG. 1 is a graph showing the storage stability of the photocurable compositions obtained in examples 1-4 of the present invention and comparative examples 1-3.
Detailed Description
The following will clearly and completely describe the technical solutions 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 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.
Example 1
Preparation of Compound 1 of chemical formula 4
121.8g of ethyl 2- ((3', 5' -di-t-butyl-4 '-hydroxy-5- ((2-isocyanato) dimethylsilyl) - [1, 1' -biphenyl ] -3-yl) dimethylsilyl) methacrylate (chemical formula 2) and 47.7g of 2- (triethoxysilyl) ethan-1-amine (chemical formula 3) were added to 300mL of toluene to dissolve, and 0.6g of dibutyltin dilaurate was added, followed by stirring for 4 hours while heating at 60 ℃. The temperature was cooled to room temperature, and the solvent was removed using a vacuum still to obtain 107g of compound 1 of chemical formula 4.
Figure BDA0003196669590000121
The compound 1 was subjected to detection analysis, and the specific results were as follows:
HPLC purity: greater than 90%.
Mass spectrum: calculated value 787.27; the test value was 786.39.
Elemental analysis:
the calculated values are: 62.55 percent of C; 8.96 percent of H; 3.56 percent of N; 14.23 percent of O; 10.70 percent of Si.
The test values are: 63.78 percent of C; 9.36 percent of H; 3.24 percent of N; 13.53 percent of O; 10.09 percent of Si.
Example 2
Preparation of Compound 2 of chemical formula 6
121.8g of ethyl 2- ((3', 5' -di-t-butyl-4 '-hydroxy-5- ((2-isocyanato) dimethylsilyl) - [1, 1' -biphenyl ] -3-yl) dimethylsilyl) methacrylate (chemical formula 2) and 47.9g of 2- (triethoxysilyl) ethylene glycol (chemical formula 5) were added to 300mL of toluene to dissolve, and 0.6g of dibutyltin dilaurate was added, followed by stirring for 4 hours while heating at 60 ℃. The temperature was cooled to room temperature, and the solvent was removed using a vacuum still to obtain 110g of compound 2 of chemical formula 6.
Figure BDA0003196669590000122
Figure BDA0003196669590000131
HPLC purity: greater than 90%.
Mass spectrum: calculated value 788.26; the test value was 787.19.
Elemental analysis:
the calculated values are: 62.47 percent of C; 8.82 percent of H; 1.78 percent of N; 16.24 percent of O; 10.69 percent of Si.
The test values are: 63.04 percent of C; 9.12 percent of H; 1.58 percent of N; 15.94 percent of O; 10.32 percent of Si.
Example 3
Preparation of Compound 3 of chemical formula 8
121.8g of isopropyl 2- ((3', 5' -di-t-butyl-4 '-hydroxy-5- ((2-isocyanato) dimethylsilyl) - [1, 1' -biphenyl ] -3-yl) dimethylsilyl) acrylate (chemical formula 7) and 47.7g of 2- (triethoxysilyl) ethan-1-amine (chemical formula 3) were added to 300mL of toluene to dissolve, and 0.6g of dibutyltin dilaurate was added, followed by stirring for 4 hours while heating at 60 ℃. The temperature was cooled to room temperature, and the solvent was removed using a vacuum still to obtain 101g of compound 3 of chemical formula 8.
Figure BDA0003196669590000132
HPLC purity: greater than 90%.
Mass spectrum: calculated value 787.27; the test value was 786.91.
Elemental analysis:
the calculated values are: 62.55 percent of C; 8.96 percent of H; 3.56 percent of N; 14.23 percent of O; 10.70 percent of Si.
The test values are: 63.35 percent of C; 10.01 percent of H; 3.26 percent of N; 13.43 percent of O; 9.95 percent of Si.
Example 4
Preparation of Compound 4 of chemical formula 10
121.8g of ethyl 2- ((3', 5' -di-t-butyl-4 '-hydroxy-5- ((2-isocyanato) dimethylsilyl) - [1, 1' -biphenyl ] -3-yl) dimethylsilyl) methacrylate (chemical formula 2) and 38.3g of 2- (trimethoxy silicon) ethylene glycol (chemical formula 9) were added to 300mL of toluene to dissolve, and 0.6g of dibutyltin dilaurate was added, followed by stirring for 4 hours while heating at 60 ℃. The temperature was cooled to room temperature, and the solvent was removed using a vacuum distiller to obtain 95g of compound 4 of chemical formula 10.
Figure BDA0003196669590000141
HPLC purity: greater than 90%.
Mass spectrum: calculated value 746.18; the test value was 745.36.
Elemental analysis:
the calculated values are: 61.17 percent of C; 8.51 percent of H; 1.88 percent of N; 17.15 percent of O; 11.29 percent of Si.
The test values are: 61.96 percent of C; 9.03 percent of H; 1.48 percent of N; 16.71 percent of O; 10.82 percent of Si.
Example 5
Preparation of Compound 5 of chemical formula 12
121.8g of ethyl 2- ((3', 5' -di-t-butyl-4 '-hydroxy-5- ((2-isocyanato) dimethylsilyl) - [1, 1' -biphenyl ] -3-yl) dimethylsilyl) methacrylate (chemical formula 2) and 29.7g of 2-aminoethyl methacrylate (chemical formula 9) were added to 300mL of toluene to dissolve, and 0.6g of dibutyltin dilaurate was added, followed by stirring for 4 hours while heating at 60 ℃. The temperature was cooled to room temperature, and the solvent was removed using a vacuum still to obtain 105g of compound 5 of chemical formula 12.
Figure BDA0003196669590000142
Examples 6 to 9 and comparative examples 1 to 3
The compounds 1 to 5 and 2, 6-di-tert-butyl-4-methylphenol in Table 1 were used as component A, 1, 12-dodecadienyl 2-propenoate and phenoxybenzyl acrylate as component B and DarocurTPO (photoinitiator) as component C.
The compounds were stirred in a reaction vessel for 30 minutes and then filtered through a 0.45um Teflon filter in the composition shown in Table 1.
TABLE 1
Figure BDA0003196669590000151
Example 10
The photocurable composition required for preparing an organic film was prepared in the proportions shown in the examples and comparative examples in Table 1 above, and the photocurable composition was 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.
The above inorganic substances were deposited as moisture-proof layers on pretreated 6cm × 6cm PEN (TEONEX, Tenjin Dupont Film) substrates by plasma chemical vapor deposition. Plasma was generated using a 13.56mhz rf match box in the inductively coupled plasma method, Trisilylamine (TSA) at a flow rate of 20 seem and ammonia at a flow rate of 60 seem were supplied into the reactor as a precursor and a reaction gas for deposition, and argon at a flow rate of 200 seem 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.
(1) Outgas measurement
Each of the compositions of examples 1-4 and comparative examples 1-3 was coated with a 5 μm thick coating on 10cm by 10cm glass using MA-6 (R)
Figure BDA0003196669590000161
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 samples having dimensions of 1cm by 3 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, the collected samples were analyzed for Outgas and listed in Table 2.
TABLE 2
Figure BDA0003196669590000162
As shown in Table 2, it can be seen from the data of out-gas that the data of out-gas is highest when the non-photocuring group (acrylate group) antioxidant is used, and the data of out-gas is lower when the photocuring group-containing antioxidant is used and the data of out-gas is similar when the antioxidant is not used in the mixture of out-gas and non-photocuring group-containing antioxidants. Therefore, whether the antioxidant contains the photocuring group has certain influence on the out-gas data of the organic layer of the packaging material.
(3) Transmittance test
Each composition of examples 1 to 4 and comparative examples 1 to 3 was mixedCoating a thickness of 5 μm on 10cm by 10cm glass using MA-6 (R)
Figure BDA0003196669590000163
Co.) was irradiated with an exposure of 200mJ/cm2 in a nitrogen atmosphere to obtain a cured organic layer. After preparation, the glass substrates were cut into samples having dimensions of 1cm x 3 cm. The visible light transmittance of the prepared film was measured at a wavelength of 550nm using Lambda 950. The collected samples were analyzed for light transmittance and are listed in table 3.
TABLE 3
Figure BDA0003196669590000171
As shown in Table 3, comparative example 1 using an antioxidant with 2 photocuring groups and comparative example 2 using an antioxidant without photocuring groups had relatively low transmittance, while examples 1 to 4 using an antioxidant with 1 photocuring group had higher transmittance and did not differ much from comparative example 3 without using an antioxidant.
(2) WVTR test
As shown in Table 4, an inorganic film (250 nm)/an organic film (3 μm)/an inorganic film (250nm) were formed on a substrate, and the moisture permeability of the encapsulating film was measured using a moisture permeability meter (AQUARAN2, MOCON). Measurements were made at 37.8 ℃ and 100% relative humidity for 24 hours.
TABLE 4
Figure BDA0003196669590000172
As shown in Table 4, in comparative example 5, in which the matte-cure-based antioxidant was used, the WVTR value was the largest, and the WVTR values of comparative example 4, comparative example 6 and examples 5-8 were lower and similar.
As can be seen from the comparison between table 1 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 screen life is longer.
TABLE 5
Figure BDA0003196669590000181
As shown in table 5 and fig. 1, in comparative example 3, which did not contain an antioxidant, when storage was performed at 25 ℃ under the same conditions and the storage stability was compared by measuring the change in viscosity, the viscosity rapidly increased after 5 days, and it was confirmed that the composition without the antioxidant was easily deteriorated and was difficult to store for a long period. The viscosity of the antioxidant-containing compositions of examples 6 to 9 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 conditions.
In summary, when the compounds 1 and 2 having two photo-curable groups were used as antioxidants, there was no adverse effect on the Outgas of the organic layer and the WVTR data of the encapsulating film, whereas when a general antioxidant was added, the Outgas of the organic layer and the WVTR of the encapsulating film both became large, and the storage stability was very good when the antioxidant was added as compared with that when no antioxidant was 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 (10)

1. A compound for thin film encapsulation, characterized in that its structure is shown in chemical formula 1:
Figure FDA0003196669580000011
wherein, R is1、R2、R6Independently selected from the same or different hydrogen, C1-C20Substituted or unsubstituted alkyl of, C6-C30Substituted or unsubstituted aryl of (a);
the R is3、R4、R5Independently selected from the same or different C1-C20Substituted or unsubstituted alkylene of (A), C6-C30Substituted or unsubstituted arylene of (a);
the R is7Is hydrogen or methyl;
said X1、X2Is one of O, S or NH, wherein X2The hydrogen in the NH represented by (C) may be replaced by1To C12Alkyl or C6-C20Aryl substitution.
2. The compound as claimed in claim 1, wherein R is a group represented by the formula1Is C4An alkyl group;
the R is2Is C4An alkyl group;
the R is3Is C2-C3An alkyl group;
the R is4Is C2An alkyl group;
the R is5Is C2An alkyl group;
the R is6Is C1-C3An alkyl group;
the R is7Is H or C1An alkyl group;
said X1Is O or NH;
said X2Is O.
3. The photocuring composition for film encapsulation is characterized by comprising 0.1-5% of a component A, 85-99.4% of a component B and 0.5-10% of a component C;
wherein the content of the first and second substances,
the component A comprises an antioxidant containing an acrylate structure shown in a chemical formula 1;
the component B comprises acrylic monomers;
the component C comprises a photoinitiator.
4. The photocurable composition for film encapsulation according to claim 3, wherein the photoinitiator comprises a photopolymerization initiator and/or a radical polymerization initiator.
5. The photocurable composition for thin film encapsulation according to claim 3, wherein the photopolymerization initiator comprises one or more of an initiator used in a photosensitive resin composition, a carbazolyl compound, a diketone compound, a boric acid sulfonic acid compound, a diazo compound, and an imidazolyl compound or a bisimidazolyl compound.
6. The photocurable composition for film encapsulation according to claim 3, wherein the radical polymerization initiator comprises a peroxide-based compound and/or an azobis-based compound.
7. The photocurable composition for film encapsulation according to claim 3, wherein said component C further comprises a photosensitizer; the photosensitizer comprises one or more of tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate and dipentaerythritol tetra-3-mercaptopropionate.
8. A film encapsulating layer comprising an organic layer and an inorganic layer, wherein the organic layer comprises the photocurable composition for film encapsulation according to any one of claims 3 to 7.
9. The thin film encapsulation layer of claim 8, wherein the inorganic layer comprises one of calcium oxide, aluminum oxide, titanium oxide, indium oxide, tin oxide, silicon nitride, silicon oxynitride, aluminum nitride, and zirconium oxide.
10. The thin film encapsulation layer according to claim 8, wherein the thickness of the thin film encapsulation layer is 0.3 μm to 20 μm.
CN202110892471.8A 2021-08-04 2021-08-04 Compound for film packaging, photocuring composition and film packaging layer Withdrawn CN113801260A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110892471.8A CN113801260A (en) 2021-08-04 2021-08-04 Compound for film packaging, photocuring composition and film packaging layer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110892471.8A CN113801260A (en) 2021-08-04 2021-08-04 Compound for film packaging, photocuring composition and film packaging layer

Publications (1)

Publication Number Publication Date
CN113801260A true CN113801260A (en) 2021-12-17

Family

ID=78893281

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110892471.8A Withdrawn CN113801260A (en) 2021-08-04 2021-08-04 Compound for film packaging, photocuring composition and film packaging layer

Country Status (1)

Country Link
CN (1) CN113801260A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114685551A (en) * 2022-03-10 2022-07-01 吉林奥来德光电材料股份有限公司 Compound for packaging film, composition and packaging film
CN114957314A (en) * 2022-05-24 2022-08-30 吉林奥来德光电材料股份有限公司 Compound for film packaging, composition, packaging film and film packaging structure

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060041087A1 (en) * 2004-07-23 2006-02-23 Cholli Ashok L Anti-oxidant macromonomers and polymers and methods of making and using the same
CN101338197A (en) * 2008-06-20 2009-01-07 辽宁天合精细化工股份有限公司 3-(3,5-ditertiary butyl-4-hydroxyphenyl)acrylic esters anti-oxidant and method for preparing same
CN101805245A (en) * 2010-04-22 2010-08-18 中国科学院新疆理化技术研究所 Synthesis method of polysubstituted hindered phenol antioxygen
CN102267876A (en) * 2011-06-20 2011-12-07 常州大学 Preparation method of styrenated hindered phenol or styrenated phenol antioxidant product
CN105130859A (en) * 2014-06-05 2015-12-09 中国石油化工股份有限公司 Screen phenol compound, manufacturing method and application thereof as antioxidant
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
CN111689853A (en) * 2020-06-28 2020-09-22 万华化学集团股份有限公司 Layered bisphenol acrylate antioxidant and preparation method thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060041087A1 (en) * 2004-07-23 2006-02-23 Cholli Ashok L Anti-oxidant macromonomers and polymers and methods of making and using the same
CN101338197A (en) * 2008-06-20 2009-01-07 辽宁天合精细化工股份有限公司 3-(3,5-ditertiary butyl-4-hydroxyphenyl)acrylic esters anti-oxidant and method for preparing same
CN101805245A (en) * 2010-04-22 2010-08-18 中国科学院新疆理化技术研究所 Synthesis method of polysubstituted hindered phenol antioxygen
CN102267876A (en) * 2011-06-20 2011-12-07 常州大学 Preparation method of styrenated hindered phenol or styrenated phenol antioxidant product
CN105130859A (en) * 2014-06-05 2015-12-09 中国石油化工股份有限公司 Screen phenol compound, manufacturing method and application thereof as antioxidant
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
CN111689853A (en) * 2020-06-28 2020-09-22 万华化学集团股份有限公司 Layered bisphenol acrylate antioxidant and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114685551A (en) * 2022-03-10 2022-07-01 吉林奥来德光电材料股份有限公司 Compound for packaging film, composition and packaging film
CN114685551B (en) * 2022-03-10 2023-12-26 吉林奥来德光电材料股份有限公司 Compound for packaging film, composition and packaging film
CN114957314A (en) * 2022-05-24 2022-08-30 吉林奥来德光电材料股份有限公司 Compound for film packaging, composition, packaging film and film packaging structure

Similar Documents

Publication Publication Date Title
CN110357916B (en) Compound for packaging film, composition and film thereof, organic light-emitting device and packaging method
CN111875521B (en) Compound for packaging film, preparation method thereof, curable composition and packaging film
KR101611001B1 (en) Composition for encapsulation, barrier layer comprising the same and encapsulated apparatus comprising the same
KR101871549B1 (en) Sealant composition for display, organic protective layer comprising the same, and display apparatus comprising the same
KR101534334B1 (en) Photocurable composition and apparatus comprising a protective layer formed using the same
CN113801260A (en) Compound for film packaging, photocuring composition and film packaging layer
KR101802574B1 (en) Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same
KR101600653B1 (en) Composition for encapsulation, barrier layer comprising the same and encapsulated apparatus comprising the same
KR102008177B1 (en) Composition for encapsulating organic light emitting device and organic light emitting display using prepared the same
CN111153922A (en) Compound, composition for packaging photoelectric device, preparation method, packaging film, electronic device and packaging method
JP2020026515A (en) Curable composition and compound
CN112898330A (en) Compound for packaging organic light-emitting device and preparation method and application thereof
KR20180102038A (en) Photo-curable composition, organic protective layer comprising the same, and apparatus comprising the same
CN111018745B (en) Compound for packaging film, organic film packaging material and packaging film
CN112538031B (en) Antioxidant for thin film packaging, composition and application thereof
TWI501030B (en) Photocurable composition, protective layer including the same, and encapsulated apparatus including the same
KR101726917B1 (en) Composition for encapsulating organic light emitting diode and organic light emitting diode display apparatus prepared using the same
EP4382578A1 (en) Ink composition for oled packaging and application thereof
CN114685551B (en) Compound for packaging film, composition and packaging film
CN113603614B (en) Compound, compound composed of compound, application and display panel
CN113402542A (en) Compound for packaging film, ink composition containing compound and film packaging structure
CN113135952B (en) Light-cured monomer, light-cured composition, packaging film and display device
CN114853799B (en) Compound for film encapsulation, composition and encapsulation film
KR102554549B1 (en) Low Refractive Composition for OLED Overcoat
CN114957314A (en) Compound for film packaging, composition, packaging film and film packaging structure

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20211217