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WO2018074507A1 - Agent de scellement pour élément d'affichage électroluminescent organique, et procédé de fabrication de celui-ci - Google Patents

Agent de scellement pour élément d'affichage électroluminescent organique, et procédé de fabrication de celui-ci Download PDF

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Publication number
WO2018074507A1
WO2018074507A1 PCT/JP2017/037656 JP2017037656W WO2018074507A1 WO 2018074507 A1 WO2018074507 A1 WO 2018074507A1 JP 2017037656 W JP2017037656 W JP 2017037656W WO 2018074507 A1 WO2018074507 A1 WO 2018074507A1
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WO
WIPO (PCT)
Prior art keywords
organic
sealing agent
display element
display elements
meth
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.)
Ceased
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PCT/JP2017/037656
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English (en)
Japanese (ja)
Inventor
信烈 梁
山本　拓也
範久 赤松
七里　徳重
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Sekisui Chemical Co Ltd
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Sekisui Chemical 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 Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to CN201780020277.2A priority Critical patent/CN108886849B/zh
Priority to KR1020187026418A priority patent/KR102416054B1/ko
Priority to JP2017556252A priority patent/JP6427283B2/ja
Priority to KR1020227022052A priority patent/KR20220097552A/ko
Publication of WO2018074507A1 publication Critical patent/WO2018074507A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • 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
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/873—Encapsulations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts

Definitions

  • the present invention relates to an encapsulant for an organic EL display element that can be easily applied by an ink jet method, can provide an organic EL display element that is excellent in low outgassing properties and excellent in reliability. Moreover, this invention relates to the manufacturing method of this sealing agent for organic EL display elements.
  • An organic electroluminescence (organic EL) display element has a laminated structure in which an organic light emitting material layer is sandwiched between a pair of electrodes facing each other, and electrons are injected into the organic light emitting material layer from one electrode. By injecting holes from the other electrode, electrons and holes are combined in the organic light emitting material layer to emit light.
  • the organic EL display element performs self-emission, it has better visibility than a liquid crystal display element that requires a backlight, can be reduced in thickness, and can be driven by a DC low voltage. Has the advantage.
  • Patent Document 1 discloses a method of sealing an organic light emitting material layer and an electrode of an organic EL display element with a laminated film of a silicon nitride film and a resin film formed by a CVD method.
  • the resin film has a role of preventing pressure on the organic layer and the electrode due to internal stress of the silicon nitride film.
  • Patent Document 1 In the method of sealing with a silicon nitride film disclosed in Patent Document 1, organic light emission occurs when a silicon nitride film is formed due to unevenness on the surface of the organic EL display element, adhesion of foreign matters, generation of cracks due to internal stress, or the like. The material layer or electrode may not be completely covered. If the coating with the silicon nitride film is incomplete, moisture will enter the organic light emitting material layer through the silicon nitride film. As a method for preventing moisture from entering into the organic light emitting material layer, Patent Document 2 discloses a method of alternately depositing an inorganic material film and a resin film. Patent Document 3 and Patent Document 4 Discloses a method of forming a resin film on an inorganic material film.
  • a method for forming a resin film there is a method in which a sealing agent is applied on a substrate using an inkjet method and then the sealing agent is cured. If such a coating method by the ink jet method is used, a resin film can be uniformly formed at high speed.
  • the sealant is made to have a low viscosity in order to be suitable for application by the ink jet method, outgas is generated, or moisture penetration cannot be sufficiently prevented in a high temperature and high humidity environment. There is a problem that the organic EL display element to be used is inferior in reliability.
  • An object of the present invention is to provide a sealing agent for organic EL display elements that can be easily applied by an ink jet method, can provide an organic EL display element that is excellent in low outgassing properties and excellent in reliability. And Moreover, an object of this invention is to provide the manufacturing method of this sealing agent for organic EL display elements.
  • the present invention 1 contains a polymerizable compound and a polymerization initiator, has a viscosity at 25 ° C. of 5 to 50 mPa ⁇ s, a surface tension at 25 ° C. of 15 to 35 mN / m, and 25 ° C., 50 It is a sealant for organic EL display elements having a water content at 25 ° C. of 1000 ppm or less after standing in an environment of% RH for 24 hours.
  • the present invention 2 is an organic EL display element sealing agent used for coating by an ink jet method, which contains a polymerizable compound and a polymerization initiator, and is 24 hours in an environment of 25 ° C. and 50% RH.
  • the sealing agent for organic EL display elements whose water content in 25 degreeC after leaving still is 1000 ppm or less.
  • the present invention is described in detail below.
  • the sealing agent for organic EL display elements of this invention 1 and the sealing agent for organic EL display elements of this invention 2 it describes as "the sealing agent for organic EL display elements of this invention”. To do.
  • the inventors of the present invention have further studied to make the moisture content within a specific range for the sealing agent for organic EL display elements having excellent ink jet coating properties. As a result, it has been found that a sealing agent for organic EL display elements can be obtained that can be easily applied by an ink jet method, can provide an organic EL display element that is excellent in low outgassing properties and excellent in reliability.
  • the present invention has been completed.
  • the sealing agent for organic EL display elements of the present invention can be used as an ink jet method for coating by a non-heated ink jet method, or can be used for coating by a heat ink jet method.
  • the “non-heated ink jet method” is a method of ink jet coating at a coating head temperature of less than 28 ° C.
  • the “heated ink jet method” is an ink jet at a coating head temperature of 28 ° C. or higher. It is a method of applying.
  • an ink jet coating head equipped with a heating mechanism is used.
  • the viscosity and the surface tension can be lowered when discharging the sealing agent for organic EL display elements.
  • Examples of the inkjet coating head equipped with the heating mechanism include KM1024 series manufactured by Konica Minolta, SG1024 series manufactured by Fuji Film Dimatix, and the like.
  • the heating temperature of the coating head is preferably in the range of 28 ° C. to 80 ° C.
  • the heating temperature of the coating head is within this range, the increase in the viscosity of the sealant for organic EL display elements over time is suppressed, and the ejection stability is improved.
  • the sealing agent for organic EL display elements of the present invention 1 has a viscosity lower limit of 5 mPa ⁇ s and an upper limit of 50 mPa ⁇ s. When the viscosity is within this range, it can be suitably applied by an ink jet method.
  • the said viscosity in this specification means the value measured on 25 degreeC and 100 rpm conditions using an E-type viscosity meter.
  • the preferable lower limit of the viscosity of the sealing agent for organic EL display elements of the present invention when applied by the non-heating ink jet method is 5 mPa ⁇ s, and the preferable upper limit is 20 mPa.s. s.
  • the more preferable lower limit of the viscosity of the sealing agent for organic EL display elements of the present invention when applied by the non-heating ink jet method is 8 mPa ⁇ s, and the more preferable upper limit is 16 mPa ⁇ s. s, a more preferred lower limit is 10 mPa ⁇ s, and a more preferred upper limit is 13 mPa ⁇ s. s.
  • the preferable lower limit of the viscosity of the sealing agent for organic EL display elements of the present invention when used for coating by the heating ink jet method is 10 mPa ⁇ s, and the preferable upper limit is 50 mPa ⁇ s. s.
  • the viscosity is within this range, it can be suitably applied by a heating ink jet method.
  • the more preferable lower limit of the viscosity of the sealing agent for organic EL display elements of the present invention when used for coating by the heating ink jet method is 20 mPa ⁇ s, and the more preferable upper limit is 40 mPa ⁇ s. s.
  • the sealing agent for organic EL display elements of the present invention 1 has a lower limit of surface tension of 15 mN / m and an upper limit of 35 mN / m. When the surface tension is within this range, it can be suitably applied by an ink jet method.
  • the preferable lower limit of the surface tension is 20 mN / m
  • the preferable upper limit is 30 mN / m
  • the more preferable lower limit is 22 mN / m
  • the more preferable upper limit is 28 mN / m.
  • the sealing agent for organic EL display elements of the present invention 2 has a preferable lower limit of surface tension of 15 mN / m and a preferable upper limit of 35 mN / m.
  • the surface tension When the surface tension is within this range, it can be suitably applied by an ink jet method.
  • the more preferable lower limit of the surface tension is 20 mN / m
  • the more preferable upper limit is 30 mN / m
  • the still more preferable lower limit is 22 mN / m
  • the still more preferable upper limit is 28 mN / m.
  • the surface tension means a value measured by a Wilhelmy method using a dynamic wettability tester at 25 ° C.
  • the sealing agent for organic EL display elements of the present invention has a water content of 1000 ppm or less at 25 ° C. after standing for 24 hours in an environment of 25 ° C. and 50% RH.
  • the moisture content is 1000 ppm or less, the obtained organic EL display element has excellent reliability.
  • a preferable upper limit of the water content is 800 ppm, and a more preferable upper limit is 300 ppm.
  • the water content is most preferably 0 ppm.
  • the said moisture content can be measured on 25 degreeC and the conditions of 50% RH environment using a Karl Fischer apparatus.
  • the measurement of the said moisture content is performed about the sealing agent within 30 minutes, after leaving still for 24 hours.
  • the viscosity, the surface tension, and the water content are described above by selecting these types and adjusting the content ratio of the polymerizable compound, the polymerization initiator, and other components that may be contained, which will be described later. It can be a range. Moreover, the said moisture content can be easily made into 1000 ppm or less by performing a dehydration process after mixing each component of the sealing agent for organic EL display elements.
  • the manufacturing method of the sealing agent for organic EL display elements which has the dehydration process exposed to 15 minutes or more is also one of this invention.
  • the preferable lower limit of the temperature in the dehydration step is 20 ° C, and the preferable upper limit is 80 ° C.
  • the dehydration step is preferably performed for 20 minutes or longer.
  • Other methods for dehydrating the organic EL display element sealant other than the dehydration step in the method for producing an organic EL display element sealant of the present invention include, for example, a method using a dehydrating agent.
  • Specific examples of the method using the dehydrating agent include a method of flowing a sealing agent for an organic EL display element through a column filled with the dehydrating agent at a flow rate of about 2.5 liters per hour, or a sealing for an organic EL display element.
  • Examples include a method of adding a dehydrating agent to the stopper and stirring the mixture, leaving it for about 12 hours, and removing the dehydrating agent by filtration or the like.
  • Examples of the dehydrating agent include molecular sieves, aluminum oxide, calcium chloride, calcium oxide, magnesium oxide, magnesium perchlorate, anhydrous magnesium sulfate, phosphorous oxide (V), anhydrous potassium carbonate, silica gel, sodium hydroxide, and anhydrous sulfuric acid. Examples thereof include sodium and zinc chloride. Of these, molecular sieves are preferable because of their excellent drying ability.
  • the sealing agent for organic EL display elements of the present invention contains a polymerizable compound.
  • the polymerizable compound preferably contains 20 to 90 parts by weight of a compound having an oxygen atom content of 30% or less in the molecule in 100 parts by weight of the entire polymerizable compound.
  • the present inventors have introduced an oxygen atom in a molecule such as a compound having a polyoxyalkylene skeleton in the main chain as a polymerizable compound. The use of a compound with a high content of was studied.
  • the resulting organic EL display element tends to be inferior in reliability, such as generating a dark spot when exposed to a high temperature and high humidity environment.
  • the present inventors have obtained an ink jet coatability by using a compound having an oxygen atom content of 30% or less as a polymerizable compound so as to have a specific content. It has been found that the reliability of the organic EL display element can be easily achieved.
  • the compound having an oxygen atom content in the molecule of 30% or less preferably has an oxygen atom content in the molecule of 25% or less, and more preferably 20% or less.
  • the more preferable lower limit of the content of the compound having an oxygen atom content of 30% or less in 100 parts by weight of the total polymerizable compound is 30 parts by weight, and the more preferable upper limit is 70 parts by weight.
  • a radical polymerizable compound or a cationic polymerizable compound can be used as the polymerizable compound.
  • a (meth) acrylic compound is preferable.
  • the (meth) acrylic compound may be a monofunctional (meth) acrylic compound or a polyfunctional (meth) acrylic compound.
  • the above “(meth) acryl” means acryl or methacryl
  • the above “(meth) acryl compound” means a compound having a (meth) acryloyl group
  • the above “(meth) “Acryloyl” means acryloyl or methacryloyl.
  • the monofunctional (meth) acrylic compound preferably has a cationic polymerizable group from the viewpoint of low outgassing property.
  • the cationic polymerizable group include a vinyl ether group, an epoxy group, an oxetanyl group, an allyl ether group, a vinyl group, and a hydroxyl group.
  • the monofunctional (meth) acrylic compound examples include 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and (meth) acrylic.
  • (meth) acrylate 3,4-epoxycyclohexylmethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and 2- (2-vinyloxyethoxy) ethyl (meth) acrylate are preferable.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • the preferred lower limit of the content of the monofunctional (meth) acrylic compound in 100 parts by weight of the polymerizable compound is 20 parts by weight, and the preferred upper limit is 80. Parts by weight.
  • the content of the monofunctional (meth) acrylic compound is within this range, the obtained sealing agent for organic EL display elements is excellent due to low outgassing properties and the like.
  • the minimum with more preferable content of the said monofunctional (meth) acryl compound is 30 weight part, and a more preferable upper limit is 60 weight part.
  • the polyfunctional (meth) acrylic compound preferably has a polyoxyalkylene skeleton in the main chain from the viewpoint of inkjet coating properties and the like.
  • a compound having a high content of oxygen atoms in the molecule when used, the obtained organic EL display element tends to be inferior in reliability, and thus a polyoxyalkylene skeleton in the main chain is likely to be obtained.
  • a functional (meth) acryl compound it is preferable to adjust the content. That is, the content of the polyfunctional (meth) acrylic compound having a polyoxyalkylene skeleton in the main chain so that the content of the compound having an oxygen atom content in the molecule of 30% or less falls within the above-described range. Is preferably adjusted.
  • the polyoxyalkylene skeleton is preferably a series of 2 to 6 oxyalkylene units. Examples of oxyalkylene units constituting the polyoxyalkylene skeleton include oxyethylene units and oxypropylene units.
  • the polyfunctional (meth) acrylic compound preferably has a structure with less carbon chain branching, and more preferably is a straight chain, from the viewpoint of inkjet coating properties and the like.
  • polyfunctional (meth) acrylic compound examples include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and dipropylene glycol di (meth) acrylate. , Tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, and the like. Of these, tetraethylene glycol di (meth) acrylate is preferable.
  • the preferred lower limit of the content of the polyfunctional (meth) acrylic compound in 100 parts by weight of the polymerizable compound is 20 parts by weight, and the preferred upper limit is 80. Parts by weight.
  • the content of the polyfunctional (meth) acrylic compound is within this range, the obtained sealing agent for organic EL display elements is excellent in ink jet coating properties and the like.
  • the minimum with more preferable content of the said polyfunctional (meth) acryl compound is 30 weight part, and a more preferable upper limit is 60 weight part.
  • the content ratio of the monofunctional (meth) acrylic compound and the polyfunctional (meth) acrylic compound is expressed as a weight ratio.
  • an epoxy compound an oxetane compound, a vinyl ether compound etc. are mentioned, for example.
  • the epoxy compound examples include bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol O type epoxy resin, 2,2′-diallyl bisphenol A type epoxy resin, Alicyclic epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene Epoxy resin, phenol novolac epoxy resin, orthocresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl Examples thereof include a volac type epoxy resin, a naphthalene phenol novolac type epoxy resin, a glycidyl amine type epoxy resin, an alkyl polyol type epoxy resin, a rubber-modified epoxy resin, a glycidyl ester compound, and 1,6-hexan
  • alicyclic epoxy resins are preferred.
  • examples of commercially available alicyclic epoxy resins include Celoxide 2000, Celoxide 2021P, Celoxide 2081, Celoxide 3000, Celoxide 8000 (all manufactured by Daicel), and Sunsizer EPS (manufactured by Shin Nippon Rika Kogyo Co., Ltd.). ) And the like.
  • oxetane compound examples include allyloxyoxetane, phenoxymethyloxetane, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3-((2-ethylhexyloxy ) Methyl) oxetane, 3-ethyl-3-((3- (triethoxysilyl) propoxy) methyl) oxetane, 3-ethyl-3-((((3-ethyloxetane-3-yl) methoxy) methyl) oxetane, Examples include oxetanylsilsesquioxane, phenol novolac oxetane, 1,4-bis (((3-ethyl-3-oxetanyl) methoxy) methyl) benzene.
  • vinyl ether compound examples include benzyl vinyl ether, cyclohexane dimethanol monovinyl ether, dicyclopentadiene vinyl ether, 1,4-butanediol divinyl ether, cyclohexane dimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, dipropylene glycol. Examples thereof include divinyl ether and tripropylene glycol divinyl ether.
  • the sealing agent for organic EL display elements of the present invention contains a polymerization initiator.
  • a radical photopolymerization initiator, a thermal radical polymerization initiator, a cationic photopolymerization initiator, or a thermal cationic polymerization initiator is suitably used depending on the type of polymerizable compound used.
  • photo radical polymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, benzyl, thioxanthone compounds, and the like.
  • Examples of commercially available photo radical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, and Lucin TPO (both benzoin methyl ether, benzoin methyl ether) Examples include ethyl ether and benzoin isopropyl ether (both manufactured by Tokyo Chemical Industry Co., Ltd.).
  • thermal radical polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
  • the azo compound include 2,2′-azobis (2,4-dimethylvaleronitrile), azobisisobutyronitrile, and the like.
  • the organic peroxide include benzoyl peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
  • thermal radical polymerization initiators examples include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001, and V-501 (all manufactured by Wako Pure Chemical Industries, Ltd.). ) And the like.
  • the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be an ionic photoacid generating type or a nonionic photoacid generating type. May be.
  • Examples of the anion portion of the ionic photoacid-generating photocationic polymerization initiator include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , and (BX 4 ) ⁇ (wherein X is at least two or more. And a phenyl group substituted with a fluorine or trifluoromethyl group).
  • Examples of the ionic photoacid-generating photocationic polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts having the above anion moiety, and (2,4-cyclohexane). And pentadien-1-yl) ((1-methylethyl) benzene) -Fe salt.
  • aromatic sulfonium salt examples include bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluorophosphate, bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluoroantimonate, and bis (4- ( Diphenylsulfonio) phenyl) sulfide bistetrafluoroborate, bis (4- (diphenylsulfonio) phenyl) sulfide tetrakis (pentafluorophenyl) borate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, diphenyl-4- ( Phenylthio) phenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfonium tetraflu
  • aromatic iodonium salt examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (Dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexa Fluorophosphate, 4-methylphenyl-4- (1-methylethy
  • aromatic diazonium salt examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis (pentafluorophenyl) borate.
  • aromatic ammonium salt examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl -2-Cyanopyridinium tetrakis (pentafluorophenyl) borate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluorophosphate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluoroantimonate, 1- (naphthylmethyl)
  • Examples include -2-cyanopyridinium tetrafluoroborate and 1- (naphthylmethyl) -2-cyanopyridinium tetrakis (pentafluorophenyl) borate.
  • Examples of the (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe salt include (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene.
  • nonionic photoacid-generating photocationic polymerization initiator examples include nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenol sulfonic acid ester, diazonaphthoquinone, N-hydroxyimide sulfonate, and the like.
  • photocationic polymerization initiators examples include, for example, DTS-200 (manufactured by Midori Chemical Co., Ltd.), UVI6990, UVI6974 (all manufactured by Union Carbide), SP-150, SP-170 (all ADEKA), FC-508, FC-512 (all from 3M), IRGACURE261, IRGACURE290 (all from BASF), PI2074 (from Rhodia), and the like.
  • the anion moiety is BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is substituted with at least two fluorine or trifluoromethyl groups
  • a sulfonium salt, a phosphonium salt, an ammonium salt, and the like are preferable.
  • sulfonium salt examples include triphenylsulfonium tetrafluoroborate and triphenylsulfonium hexafluoroantimonate.
  • Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.
  • ammonium salt examples include dimethylphenyl (4-methoxybenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methoxybenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methoxybenzyl) ammonium tetrakis (pentafluorophenyl).
  • thermal cationic polymerization initiators include, for example, Sun-Aid SI-60, Sun-Aid SI-80, Sun-Aid SI-B3, Sun-Aid SI-B3A, Sun-Aid SI-B4 (all of which are Sanshin Chemical Industry Co., Ltd.). CXC1612, CXC1821 (all manufactured by King Industries) and the like.
  • the content of the polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the polymerizable compound.
  • the content of the polymerization initiator is 0.01 parts by weight or more, the obtained sealing agent for organic EL display elements is more excellent in curability.
  • the content of the polymerization initiator is 10 parts by weight or less, the curing reaction of the obtained sealing agent for organic EL display elements does not become too fast, and the workability is improved, and the cured product is more uniform. It can be.
  • the minimum with more preferable content of the said polymerization initiator is 0.05 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a sensitizer.
  • the sensitizer has a role of further improving the polymerization initiation efficiency of the polymerization initiator and further promoting the curing reaction of the sealing agent for organic EL display elements of the present invention.
  • sensitizer examples include thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, o- Examples include methyl benzoylbenzoate, 4,4′-bis (dimethylamino) benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
  • thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, o- Examples include methyl benzoylbenzoate, 4,4′-bis (dimethylamino) benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
  • the content of the sensitizer is preferably 0.01 parts by weight and preferably 3 parts by weight with respect to 100 parts by weight of the polymerizable compound.
  • the content of the sensitizer is 0.01 parts by weight or more, the sensitizing effect is more exhibited.
  • the content of the sensitizer is 3 parts by weight or less, light can be transmitted to a deep part without excessive absorption.
  • the minimum with more preferable content of the said sensitizer is 0.1 weight part, and a more preferable upper limit is 1 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a silane coupling agent.
  • the said silane coupling agent has a role which improves the adhesiveness of the sealing agent for organic EL display elements of this invention, a board
  • silane coupling agent examples include 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, and the like. These silane coupling agents may be used independently and 2 or more types may be used together.
  • the content of the silane coupling agent is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the polymerizable compound. When the content of the silane coupling agent is within this range, the effect of improving the adhesiveness is suppressed while suppressing the excess silane coupling agent from bleeding out.
  • the minimum with more preferable content of the said silane coupling agent is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for organic EL display elements of the present invention may further contain a surface modifier as long as the object of the present invention is not impaired.
  • a surface modifier By containing the surface modifier, the flatness of the coating film can be imparted to the organic EL display element sealant of the present invention.
  • the surface modifier include surfactants and leveling agents.
  • Examples of the surface modifier include silicone-based and fluorine-based ones.
  • Examples of commercially available surface modifiers include BYK-340, BYK-345 (both manufactured by Big Chemie Japan) and Surflon S-611 (manufactured by AGC Seimi Chemical).
  • the encapsulant for organic EL display elements of the present invention may contain a solvent for the purpose of adjusting the viscosity, but problems such as deterioration of the organic light emitting material layer and generation of outgas due to the remaining solvent. Therefore, it is preferable that the solvent is not contained or the solvent content is 0.05% by weight or less.
  • the sealing agent for organic EL display elements of this invention contains well-known various additives, such as a reinforcing agent, a softening agent, a plasticizer, a viscosity modifier, a ultraviolet absorber, antioxidant, as needed. May be.
  • Examples of the method for producing the sealing agent for organic EL display elements of the present invention include a polymerizable compound using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll. And a method of mixing a polymerization initiator and an additive such as a silane coupling agent added if necessary.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll.
  • a method of mixing a polymerization initiator and an additive such as a silane coupling agent added if necessary.
  • the preferable lower limit of the total light transmittance of light at a wavelength of 380 to 800 nm of the cured product of the encapsulant for organic EL display elements of the present invention is 80%.
  • the total light transmittance is 80% or more, the obtained organic EL display element has superior optical characteristics.
  • a more preferable lower limit of the total light transmittance is 85%.
  • cured material used for the measurement of the said total light transmittance is a photocurable sealing agent, it will obtain by, for example, irradiating 3000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 365 nm with a LED lamp to a sealing agent. If it is a thermosetting sealant, it can be obtained by heating at 80 ° C. for 1 hour, for example.
  • the transmittance at 400 nm after irradiating the cured product with ultraviolet rays for 100 hours is preferably 85% or more at an optical path length of 20 ⁇ m.
  • the transmittance after irradiating the ultraviolet rays for 100 hours is 85% or more, the transparency is high, the loss of light emission is small, and the color reproducibility is excellent.
  • a more preferable lower limit of the transmittance after irradiation with the ultraviolet rays for 100 hours is 90%, and a more preferable lower limit is 95%.
  • the light source for irradiating the ultraviolet rays a conventionally known light source such as a xenon lamp or a carbon arc lamp can be used.
  • permeability after irradiating the said ultraviolet-ray for 100 hours is a photocurable sealing agent, for example, ultraviolet rays with a wavelength of 365 nm will be 3000 mJ / cm with a LED lamp to sealing agent. If it is a thermosetting sealant, it can be obtained, for example, by heating at 80 ° C. for 1 hour.
  • the sealant for an organic EL display device of the present invention has a moisture permeability of 100 g / 100 ⁇ m when the cured product is exposed to an environment of 85 ° C. and 85% RH for 24 hours in accordance with JIS Z 0208.
  • m is preferably 2 or less.
  • the moisture permeability is 100 g / m 2 or less, the effect of preventing moisture from reaching the organic light emitting material layer and the generation of dark spots is improved, and the resulting organic EL display element is more reliable. It will be a thing.
  • cured material used for the said moisture permeability measurement is a photocurable sealing agent, for example, it can obtain by irradiating 3000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 365 nm with a LED lamp to sealing agent. If it is a thermosetting sealing agent, it can obtain by heating at 80 degreeC for 1 hour, for example.
  • the sealing agent for organic EL display elements of the present invention may have a moisture content of less than 0.5% when the cured product is exposed to an environment of 85 ° C. and 85% RH for 24 hours. preferable.
  • the moisture content of the cured product is less than 0.5%, the effect of preventing the deterioration of the organic light emitting material layer due to moisture in the cured product is excellent, and the obtained organic EL display element is excellent in reliability. It becomes.
  • a more preferable upper limit of the moisture content of the cured product is 0.3%.
  • Examples of the method for measuring the moisture content include a method of obtaining by a Karl Fischer method in accordance with JIS K 7251, and a method of obtaining a weight increment after water absorption in accordance with JIS K 7209-2.
  • cured material used for the measurement of the said moisture content is a photocurable sealing agent, it can obtain by irradiating 3000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 365 nm with a LED lamp to a sealing agent, for example. If it is a thermosetting sealing agent, it can obtain by heating at 80 degreeC for 1 hour, for example.
  • the sealing agent for organic EL display elements of the present invention 1 is suitably used for coating by an ink jet method
  • the sealing agent for organic EL display elements of the present invention 2 is used for coating by an ink jet method.
  • a method for producing an organic EL display element using the sealing agent for organic EL display elements of the present invention for example, a step of applying the sealing agent for organic EL display elements of the present invention to a substrate by an inkjet method, And a method of curing the applied sealing agent for organic EL display elements by light irradiation and / or heating.
  • the organic EL display element sealant of the present invention may be applied to the entire surface of the substrate, or on a part of the substrate. It may be applied.
  • the shape of the sealing portion of the sealing agent for organic EL display elements of the present invention formed by coating is not particularly limited as long as it is a shape that can protect the laminate having the organic light emitting material layer from the outside air. A shape that completely covers the body may be formed, a closed pattern may be formed in the peripheral portion of the laminate, or a pattern having a shape in which a partial opening is provided in the peripheral portion of the laminate. It may be formed.
  • the organic EL display element sealant of the present invention irradiates light having a wavelength of 300 nm to 400 nm and an accumulated light amount of 300 to 3000 mJ / cm 2. Can be suitably cured.
  • Examples of the light source for irradiating the organic EL display element sealant of the present invention with light include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, an excimer laser, a chemical lamp, a black light lamp, and a microwave.
  • Examples include an excited mercury lamp, a metal halide lamp, a sodium lamp, a halogen lamp, a xenon lamp, an LED lamp, a fluorescent lamp, sunlight, and an electron beam irradiation device.
  • These light sources may be used independently and 2 or more types may be used together. These light sources are appropriately selected according to the absorption wavelength of the photo radical polymerization initiator or the photo cationic polymerization initiator.
  • Examples of the light irradiation means to the organic EL display element sealant of the present invention include simultaneous irradiation of various light sources, sequential irradiation with a time difference, combined irradiation of simultaneous irradiation and sequential irradiation, and the like. Any irradiation means may be used.
  • the cured product obtained by the step of curing the organic EL display element sealing agent by light irradiation and / or heating may be further coated with an inorganic material film.
  • the inorganic material forming the inorganic material layer can be a conventionally known, for example, silicon nitride (SiN x), silicon oxide (SiO x), and the like.
  • the inorganic material film may be a single layer or may be a laminate of a plurality of types of layers. Moreover, you may coat
  • the method for producing the organic EL display element comprises a step of bonding a base material (hereinafter also referred to as “one base material”) coated with the organic EL display element sealing agent of the present invention and the other base material.
  • the substrate on which the sealing agent for organic EL display elements of the present invention is applied (hereinafter also referred to as “one substrate”) may be a substrate on which a laminate having an organic light emitting material layer is formed. A base material on which the laminate is not formed may be used.
  • the present invention is applied to the one substrate so that the laminate can be protected from the outside air when the other substrate is bonded. What is necessary is just to apply
  • the sealing agent portion having a closed pattern may be formed in a shape that fits in the shape.
  • the step of curing the organic EL display element sealant by light irradiation and / or heating may be performed before the step of bonding the one base material and the other base material, You may perform after the process of bonding a base material and said other base material.
  • the organic EL display of the present invention preferably has a pot life of 1 minute or longer after irradiation with light and / or heating until the curing reaction proceeds and adhesion becomes impossible. When the pot life is 1 minute or longer, higher adhesion strength can be obtained without excessive curing before the one base material and the other base material are bonded together.
  • a method of bonding the one base material and the other base material is not particularly limited, but it is preferable to bond them in a reduced-pressure atmosphere.
  • the preferable lower limit of the degree of vacuum in the reduced-pressure atmosphere is 0.01 kPa, and the preferable upper limit is 10 kPa.
  • the degree of vacuum in the reduced-pressure atmosphere is within this range, the one base material and the other base material are not spent for a long time to achieve a vacuum state due to the airtightness of the vacuum device and the ability of the vacuum pump. Bubbles in the sealing agent for organic EL display elements of the present invention when the material is bonded can be more efficiently removed.
  • an encapsulant for an organic EL display element that can be easily applied by an ink jet method, can obtain an organic EL display element that is excellent in low outgassing properties and excellent in reliability. Can do.
  • the manufacturing method of this sealing agent for organic EL display elements can be provided.
  • Examples 1 to 7, Comparative Examples 1 to 4 In accordance with the blending ratio described in Table 1, each material was uniformly stirred and mixed at a stirring speed of 3000 rpm using a homodisper type stirring mixer (“Primix Corporation,“ Homodisper L type ”). To 7 and Comparative Examples 1 to 4 were prepared. Each sealing agent for organic EL display elements obtained in Examples 1 to 5 and Comparative Examples 1 and 2 was subjected to a dehydration process in which the mixture was stirred and mixed and then exposed to an environment of 50 ° C. and 0.1 MPa for 30 minutes.
  • each sealing agent for organic EL display elements obtained in Examples and Comparative Examples was performed using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”) at 25 ° C. and 100 rpm.
  • Table 1 shows the measured viscosity and the surface tension measured at 25 ° C. with a dynamic wettability tester (Reska, “WET-6100”).
  • 10 g of each organic EL display element sealant obtained in Examples and Comparative Examples was placed in a high vessel container and allowed to stand in a constant temperature and humidity chamber at 25 ° C. and 50% RH for 24 hours, and then the Karl Fischer device.
  • this substrate is fixed to the substrate folder of the vacuum evaporation apparatus, and 200 mg of N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine ( ⁇ -NPD) is added to the unglazed crucible.
  • 200 mg of tris (8-quinolinolato) aluminum (Alq 3 ) was put in the crucible, and the pressure in the vacuum chamber was reduced to 1 ⁇ 10 ⁇ 4 Pa. Thereafter, the crucible containing ⁇ -NPD was heated, and ⁇ -NPD was deposited on the substrate at a deposition rate of 15 s / s to form a 600 ⁇ ⁇ hole transport layer.
  • the crucible containing Alq 3 was heated to form an organic light emitting material layer having a thickness of 600 ⁇ at a deposition rate of 15 ⁇ / s. Thereafter, the substrate on which the hole transport layer and the organic light emitting material layer are formed is transferred to another vacuum vapor deposition apparatus, and 200 mg of lithium fluoride is added to a tungsten resistance heating boat in the vacuum vapor deposition apparatus, and an aluminum wire is added to another tungsten boat. 1.0 g was added.
  • the inside of the vapor deposition unit of the vacuum vapor deposition apparatus is depressurized to 2 ⁇ 10 ⁇ 4 Pa to form a lithium fluoride film with a thickness of 5 mm at a deposition rate of 0.2 kg / s, and then aluminum with a film thickness of 1000 mm at a rate of 20 kg / s. did.
  • the inside of the vapor deposition unit was returned to normal pressure with nitrogen, and the substrate on which the laminate having the organic light emitting material layer of 10 mm ⁇ 10 mm was arranged was taken out.
  • a mask having an opening of 13 mm ⁇ 13 mm is installed so as to cover the entire laminated body of the substrate on which the obtained laminated body is arranged, and inorganic by plasma CVD method.
  • a material film A was formed.
  • SiH 4 gas and nitrogen gas are used as source gases, the flow rates of each are SiH 4 gas 10 sccm, nitrogen gas 200 sccm, RF power 10 W (frequency 2.45 GHz), chamber temperature 100 ° C., chamber The test was performed under the condition that the internal pressure was 0.9 Torr.
  • the formed inorganic material film A had a thickness of about 1 ⁇ m.
  • each material was uniformly stirred and mixed at a stirring speed of 3000 rpm using a homodisper type stirring mixer (manufactured by Primics Co., Ltd., “Homodisper L type”).
  • the sealing agent for organic EL display elements was produced by performing the spin-drying
  • the surface tension was measured with a dynamic wettability tester (Reska, “WET-6100”). Moreover, after putting 10 g of obtained sealing agents for organic EL display elements in a high vessel container and leaving it still in a thermostat at 25 ° C. and 50% RH for 24 hours, using a Karl Fischer device, The moisture content of the sealing agent for organic EL display elements was measured under the condition of 50% RH. BHB-160 (manufactured by Kinki Container Co., Ltd.) was used as the high vessel container, and MKC-710S (manufactured by Kyoto Electronics Industry Co., Ltd.) was used as the Karl Fischer apparatus.
  • BHB-160 manufactured by Kinki Container Co., Ltd.
  • MKC-710S manufactured by Kyoto Electronics Industry Co., Ltd.
  • the moisture content was measured for the sealant immediately after taking out from the thermo-hygrostat (within 30 minutes) after standing for 24 hours.
  • the obtained sealant for organic EL display element was alkali-washed with an ink-jet discharge device (“NanoPrinter500” manufactured by Microjet Co., Ltd.) with a droplet volume of 30 picoliters (manufactured by Asahi Glass Co., Ltd.). , “AN100”).
  • the ink jet discharge performance was evaluated by assuming that “ ⁇ ” indicates that the liquid droplets were normally discharged from the ink jet nozzle and landed on the substrate, and “X” indicates that the liquid droplets were not normally discharged.
  • IJH-30 manufactured by IJT was used as an inkjet coating head, and inkjet coating was performed without heating (head temperature 25 ° C.).
  • Example 2 The same sealing agent for organic EL display elements as that prepared in Experimental Example 1 was prepared. Inkjet ejection properties were evaluated in the same manner as in Experimental Example 1 except that IJH-30 (manufactured by IJT) was used as an inkjet coating head and inkjet coating was performed while heating (head temperature 60 ° C.).
  • an encapsulant for an organic EL display element that can be easily applied by an ink jet method, can obtain an organic EL display element that is excellent in low outgassing properties and excellent in reliability. Can do.
  • the manufacturing method of this sealing agent for organic EL display elements can be provided.

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Abstract

L'invention a pour objet de fournir un agent de scellement pour élément d'affichage électroluminescent organique qui peut être facilement appliqué par jet d'encre, qui est excellent en termes de faible dégazement, et qui permet d'obtenir un élément d'affichage électroluminescent organique d'une excellente fiabilité. En outre, l'invention a pour objet de fournir un procédé de fabrication de cet agent de scellement pour élément d'affichage électroluminescent organique. Plus précisément, l'invention concerne un agent de scellement pour élément d'affichage électroluminescent organique qui comprend un composé polymérisable et un initiateur de polymérisation, dont la viscosité à 25°C est comprise entre ５ et ５０ｍＰａ・ｓ, dont la tension superficielle à 25°C est comprise entre １５ et ３５ｍＮ／ｍ, et dont la teneur en eau à 25°C après repos de 24 heures dans un environnement à 25°C et d'humidité relative à 50%, est inférieure ou égale à 1000ppm.
PCT/JP2017/037656 2016-10-19 2017-10-18 Agent de scellement pour élément d'affichage électroluminescent organique, et procédé de fabrication de celui-ci Ceased WO2018074507A1 (fr)

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CN201780020277.2A CN108886849B (zh) 2016-10-19 2017-10-18 有机el显示元件用密封剂以及有机el显示元件用密封剂的制造方法
KR1020187026418A KR102416054B1 (ko) 2016-10-19 2017-10-18 유기 el 표시 소자용 봉지제 및 유기 el 표시 소자용 봉지제의 제조 방법
JP2017556252A JP6427283B2 (ja) 2016-10-19 2017-10-18 有機ｅｌ表示素子用封止剤及び有機ｅｌ表示素子用封止剤の製造方法
KR1020227022052A KR20220097552A (ko) 2016-10-19 2017-10-18 유기 el 표시 소자용 봉지제 및 유기 el 표시 소자용 봉지제의 제조 방법

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JP2019212398A (ja) * 2018-05-31 2019-12-12 パナソニックＩｐマネジメント株式会社 有機ｅｌ素子封止用紫外線硬化性樹脂組成物、有機ｅｌ発光装置の製造方法及び有機ｅｌ発光装置
JP2019212399A (ja) * 2018-05-31 2019-12-12 パナソニックＩｐマネジメント株式会社 有機ｅｌ素子封止用紫外線硬化性樹脂組成物、有機ｅｌ発光装置の製造方法及び有機ｅｌ発光装置
JP2020021714A (ja) * 2018-08-03 2020-02-06 パナソニックＩｐマネジメント株式会社 有機ｅｌ素子封止用紫外線硬化性樹脂組成物、有機ｅｌ発光装置の製造方法及び有機ｅｌ発光装置
WO2025126843A1 (fr) * 2023-12-15 2025-06-19 コニカミノルタ株式会社 Composition pour sceller un dispositif électronique pour jet d'encre, film d'étanchéité de dispositif électronique et procédé de formation de film d'étanchéité de dispositif électronique

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WO2022191232A1 (fr) * 2021-03-10 2022-09-15 三井化学株式会社 Composition de résine durcissant aux ultraviolets pour agent d'étanchéité el organique
JP7705551B2 (ja) 2022-03-25 2025-07-09 デンカ株式会社 有機エレクトロルミネッセンス素子用封止剤、封止材及び有機エレクトロルミネッセンス表示装置、及び、有機エレクトロルミネッセンス素子用封止剤の製造方法
WO2023182281A1 (fr) 2022-03-25 2023-09-28 デンカ株式会社 Agent d'encapsulation pour élément électroluminescent organique, matériau d'encapsulation et dispositif d'affichage électroluminescent organique

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