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WO2019203123A1 - Agent d'étanchéité pour élément d'affichage électroluminescent organique et élément d'affichage électroluminescent organique de type à émission par le haut - Google Patents

Agent d'étanchéité pour élément d'affichage électroluminescent organique et élément d'affichage électroluminescent organique de type à émission par le haut Download PDF

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Publication number
WO2019203123A1
WO2019203123A1 PCT/JP2019/015824 JP2019015824W WO2019203123A1 WO 2019203123 A1 WO2019203123 A1 WO 2019203123A1 JP 2019015824 W JP2019015824 W JP 2019015824W WO 2019203123 A1 WO2019203123 A1 WO 2019203123A1
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WIPO (PCT)
Prior art keywords
organic
display element
sealing agent
sealant
display elements
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
Application number
PCT/JP2019/015824
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English (en)
Japanese (ja)
Inventor
千鶴 金
山本　拓也
七里　徳重
美香 笹野
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.)
Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to JP2019521511A priority Critical patent/JP7497155B2/ja
Priority to CN201980025061.4A priority patent/CN111937493B/zh
Priority to KR1020207018042A priority patent/KR20210004942A/ko
Publication of WO2019203123A1 publication Critical patent/WO2019203123A1/fr
Anticipated expiration legal-status Critical
Priority to JP2023102355A priority patent/JP2023123648A/ja
Ceased legal-status Critical Current

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Classifications

    • 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
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
    • 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
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • 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
    • 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
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/302—Details of OLEDs of OLED structures
    • H10K2102/3023—Direction of light emission
    • H10K2102/3026—Top emission
    • 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

Definitions

  • the present invention relates to an encapsulant for an organic EL display element that can provide an organic EL display element that is excellent in inkjet coating properties and that is excellent in display performance even if it is a top emission type. Moreover, this invention relates to the top emission type organic EL display element which uses this sealing agent for organic EL display elements.
  • organic electroluminescence (hereinafter, also referred to as “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 the organic light emitting material layer is formed from one electrode on the organic light emitting material layer.
  • organic EL organic electroluminescence
  • 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.
  • the organic light-emitting material layer and electrodes constituting the organic EL display element have a problem that the characteristics are easily deteriorated by moisture, oxygen, and the like. Therefore, in order to obtain a practical organic EL display element, it is necessary to extend the life by blocking the organic light emitting material layer and the electrode from the atmosphere.
  • a sealant for example, Patent Document 1.
  • an inorganic film called a passivation film is usually provided on a laminate having an organic light emitting material layer in order to sufficiently suppress the transmission of moisture, oxygen, and the like. A method of sealing the top with a sealant is used.
  • a top emission type organic substance that extracts light from the upper surface side of the organic light emitting layer is used.
  • EL display elements have attracted attention. This method has an advantage that it has a high aperture ratio and is driven at a low voltage, which is advantageous for extending the life.
  • a transparent moisture-proof group such as glass is provided on the upper surface side of the light emitting element via a transparent sealing layer. It seals by laminating
  • stacking a material for example, patent document 2).
  • the sealing layer As a method of forming the sealing layer, 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, the sealing layer can be formed at high speed and uniformly.
  • a sealing agent suitable for application by the ink jet method is used in the top emission type organic EL display element, there is a problem that display defects such as dark spots may occur in the obtained organic EL display element. In particular, even a sealant that did not cause display failure in the bottom emission type may cause display failure when used in a top emission type organic EL display element.
  • Invention 1 contains a polymerizable compound and a polymerization initiator, has a cure shrinkage of less than 11%, and is measured by a thermal desorption GC-MS method at 80 ° C. for 30 minutes. It is the sealing agent for organic EL display elements whose outgas generation amount of hardened
  • the present invention 2 is an organic EL display element sealing agent used for coating by an ink jet method, contains a polymerizable compound and a polymerization initiator, has a curing shrinkage of less than 11%, and This is a sealing agent for organic EL display elements in which the amount of outgas generation of a cured product measured by a thermal desorption GC-MS method at 80 ° C.
  • 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 cathode is thinned from the viewpoint of translucency, and the thinned cathode is influenced by the sealing agent used for the sealing layer formed on the cathode. It becomes easy to receive.
  • the sealing agent did not cause display defects in the bottom emission type due to the influence of the sealing agent on the cathode, the display I thought it was the cause of the failure. Accordingly, the present inventors set the curing shrinkage rate and the outgas generation amount of the cured product measured under stricter conditions than those of the sealing agent for organic EL display elements excellent in inkjet coating property to less than a specific value, respectively. I examined that. As a result, it has been found that an organic EL display element sealing agent that can provide an organic EL display element that is excellent in ink jet coating property and that is excellent in display performance even in the top emission type can be obtained. It came to complete.
  • 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 viscosity with time of the sealant for organic EL display elements is further suppressed, and the ejection stability is improved.
  • the sealing agent for organic EL display elements of the present invention 1 has a preferable lower limit of viscosity at 25 ° C. of 5 mPa ⁇ s, and a preferable upper limit of 50 mPa ⁇ s.
  • the viscosity at 25 ° C. is within this range, it can be suitably applied by an ink jet method.
  • the “viscosity” means a value measured using an E-type viscometer under the conditions of 25 ° C. and 100 rpm. Examples of the E type viscometer include VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.), and a CP1 type cone plate can be used.
  • coating by the said non-heating-type inkjet method is 5 mPa * s, and a more preferable upper limit is 20 mPa.s. s.
  • the more preferable lower limit of the viscosity at 25 ° C. of the encapsulant 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 particularly preferred lower limit is 10 mPa ⁇ s, and a particularly preferred upper limit is 13 mPa ⁇ s. s.
  • the lower limit of the viscosity at 25 ° C. 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 more 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 at 25 ° C. of the encapsulant 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 preferable minimum of the surface tension in 25 degreeC is 15 mN / m, and a preferable upper limit is 35 mN / m.
  • a preferable lower limit of the surface tension at 25 ° C. is 20 mN / m
  • a more preferable upper limit is 30 mN / m
  • a still more preferable lower limit is 22 mN / m
  • a still more preferable upper limit is 28 mN / m.
  • the sealing agent for organic EL display elements of this invention 2 has a preferable lower limit of the surface tension at 25 ° C. of 15 mN / m, and a preferable upper limit of 35 mN / m.
  • the surface tension at 25 ° C. is within this range, it can be suitably applied by an ink jet method.
  • a more preferable lower limit of the surface tension at 25 ° C. is 20 mN / m
  • a more preferable upper limit is 30 mN / m
  • a still more preferable lower limit is 22 mN / m
  • a 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. Examples of the dynamic wettability tester include a WET-6100 type (manufactured by Reska).
  • the sealing agent for organic EL display elements of the present invention has a curing shrinkage rate of less than 11%.
  • the curing shrinkage rate is less than 11%, the organic EL display element sealing agent of the present invention can obtain an organic EL display element having excellent display performance even if it is a top emission type.
  • a preferable upper limit of the curing shrinkage is 10%, and a more preferable upper limit is 9%. Further, there is no particular lower limit for the curing shrinkage, but the substantial lower limit is 1%.
  • the "cure shrinkage" as used herein a specific gravity at 25 ° C. of sealant before curing G A, when the specific gravity at 25 ° C. of a cured product of the sealant was G B, the following formula This is a calculated value.
  • Cure shrinkage (%) ((G B -G A) / G B) ⁇ 100
  • cured material used for the said specific gravity measurement is a photocurable sealing agent
  • it can be obtained by, for example, irradiating the sealing agent with 2000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 395 nm with an LED lamp.
  • it is a thermosetting sealing agent, it can obtain by heating at 80 degreeC for 1 hour, for example.
  • the encapsulant for organic EL display elements of the present invention has an outgas generation amount of a cured product of less than 3000 ppm as measured by a thermal desorption GC-MS method at 80 ° C. for 30 minutes. Since the outgas generation amount of the cured product measured by the above thermal desorption GC-MS method is less than 3000 ppm, the organic EL display element sealant of the present invention is an organic compound having excellent display performance even if it is a top emission type. An EL display element can be obtained.
  • a preferable upper limit of the outgas generation amount of the cured product measured by the thermal desorption GC-MS method is 2500 ppm, and a more preferable upper limit is 2000 ppm.
  • the outgas generation amount of the cured product measured by the thermal desorption GC-MS method is most preferably 0 ppm.
  • the measurement of the outgas generation amount of the cured product by the above thermal desorption GC-MS method was conducted by heating 1 mg of the cured product using a thermal desorption apparatus and a GC-MS apparatus at 80 ° C. for 30 minutes. This can be done by measuring the amount of gas component generated.
  • the cured product used for the measurement of the outgas generation amount by the thermal desorption GC-MS is a photocurable sealant, for example, UV light having a wavelength of 395 nm is applied to the sealant with an LED lamp at 2000 mJ / cm 2. If it is a thermosetting sealant, it can be obtained by, for example, heating at 80 ° C. for 1 hour.
  • the viscosity at 25 ° C., the surface tension at 25 ° C., the curing shrinkage rate, and the outgas generation amount of the cured product measured by the thermal desorption GC-MS method are described below, a polymerizable compound, a polymerization initiator, And about other components, such as a sensitizer, it can be set as the range mentioned above by selection of these kinds, and adjustment of a content rate.
  • the curing shrinkage rate and the outgas generation amount of the cured product measured by the thermal desorption GC-MS method should be within the above-described ranges by selecting the type of polymerizable compound and adjusting the content ratio described below. Becomes easy.
  • the sealing agent for organic EL display elements of the present invention contains a polymerizable compound.
  • a polymerizable compound a cationic polymerizable compound or a radical polymerizable compound can be used.
  • the said polymeric compound contains a cationically polymerizable compound from a viewpoint of making a cure shrinkage rate lower.
  • the cationic polymerizable compound examples include oxetane compounds, epoxy compounds, vinyl ether compounds, and the like.
  • the polymerizable compound preferably includes at least one of an oxetane compound and an epoxy compound, more preferably includes an oxetane compound, and further preferably includes a polyfunctional oxetane compound.
  • oxetane compound examples include 3-ethyl-3-(((3-ethyloxetane-3-yl) methoxy) methyl) oxetane, 3-ethyl-3-((2-ethylhexyloxy) methyl) oxetane, 3 -Ethyl-3-((3- (triethoxysilyl) propoxy) methyl) oxetane, phenol novolac oxetane, 1,4-bis (((3-ethyl-3-oxetanyl) methoxy) methyl) benzene and the like.
  • 3-ethyl-3-(((3-ethyloxetane-3-yl) methoxy) methyl) oxetane is preferable.
  • These oxetane compounds may be used alone or in combination of two or more.
  • Examples of the epoxy compound include 1,7-octadiene diepoxide, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, and dipropylene glycol.
  • Examples thereof include diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether, phenyl glycidyl ether, and phenylene diglycidyl ether.
  • These epoxy compounds may be used independently and 2 or more types may be used in combination.
  • 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. These vinyl ether compounds may be used alone or in combination of two or more.
  • a (meth) acrylic compound is preferable.
  • (meth) acryl means acryl or methacryl
  • (meth) acryl compound means a compound having a (meth) acryloyl group
  • (meth) acryloyl means a compound having a (meth) acryloyl group
  • (meth) acryloyl means a compound having a (meth) acryloyl group
  • (meth) acryloyl "Means acryloyl or methacryloyl.
  • Examples of the (meth) acrylic compound include isobornyl (meth) acrylate, glycidyl (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, and dicyclopentenyl.
  • isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and dicyclopentanyl (meth) acrylate are preferable.
  • These (meth) acrylic compounds may be used alone or in combination of two or more.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • the sealing agent for organic EL display elements of the present invention contains a polymerization initiator.
  • a polymerization initiator a cationic photopolymerization initiator or a radical photopolymerization initiator is suitably used depending on the type of polymerizable compound used.
  • 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.
  • anion portion of the ionic photoacid-generating photocationic polymerization initiator examples include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , (BX 4 ) ⁇ (where X is at least two or more fluorine atoms) Or a phenyl group substituted with a trifluoromethyl group).
  • anion moiety examples include PF m (C n F 2n + 1 ) 6-m ⁇ (wherein, m is an integer of 0 or more and 5 or less, and n is an integer of 1 or more and 6 or less). Can be mentioned.
  • 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.
  • Examples of commercially available photocationic polymerization initiators include, for example, a photocationic polymerization initiator manufactured by Midori Chemical Co., a photocationic polymerization initiator manufactured by Union Carbide, a photocationic polymerization initiator manufactured by ADEKA, Examples thereof include a photocationic polymerization initiator manufactured by 3M, a photocationic polymerization initiator manufactured by BASF, a photocationic polymerization initiator manufactured by Rhodia, and a photocationic polymerization initiator manufactured by San Apro. Examples of the photocationic polymerization initiator manufactured by Midori Chemical Co., Ltd. include DTS-200.
  • Examples of the cationic photopolymerization initiator manufactured by Union Carbide include UVI6990, UVI6974, and the like.
  • Examples of the photocation polymerization initiator manufactured by ADEKA include SP-150 and SP-170.
  • Examples of the cationic photopolymerization initiator manufactured by 3M include FC-508, FC-512, and the like.
  • Examples of the cationic photopolymerization initiator manufactured by BASF include IRGACURE261, IRGACURE290, and the like.
  • Examples of the photocationic polymerization initiator manufactured by Rhodia include PI 2074.
  • Examples of the cationic photopolymerization initiator manufactured by Sun Apro include CPI-100P, CPI-200K, CPI-210S, and the like.
  • 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.
  • the radical photopolymerization initiator by BASF As what is marketed among the said radical photopolymerization initiators, the radical photopolymerization initiator by BASF, the radical photopolymerization initiator by Tokyo Chemical Industry, etc. are mentioned, for example.
  • the radical photopolymerization initiator manufactured by BASF include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, and Lucyrin TPO.
  • the photo radical polymerization initiator manufactured by Tokyo Chemical Industry Co., Ltd. include benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • 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 examples include thermal cationic polymerization initiators manufactured by Sanshin Chemical Industry, thermal cationic polymerization initiators manufactured by King Industries, and the like.
  • thermal cationic polymerization initiator manufactured by Sanshin Chemical Industry Co., Ltd. examples include Sun-Aid SI-60, Sun-Aid SI-80, Sun-Aid SI-B3, Sun-Aid SI-B3A, and Sun-Aid SI-B4.
  • thermal cationic polymerization initiator manufactured by King Industries examples include CXC1612 and CXC1821.
  • 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, V-501 (all of which are Fuji Film Wako Pure Chemical Industries, Ltd.). Manufactured) 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, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, methyl o-benzoylbenzoate, 4,4 Examples include '-bis (dimethylamino) benzophenone and 4-benzoyl-4'-methyldiphenyl sulfide.
  • thioxanthone compound include 2,4-diethylthioxanthone.
  • 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 this invention may contain a thermosetting agent in the range which does not inhibit the objective of this invention.
  • the thermosetting agent include hydrazide compounds, imidazole derivatives, acid anhydrides, dicyandiamides, guanidine derivatives, modified aliphatic polyamines, addition products of various amines and epoxy resins, and the like.
  • the hydrazide compound include 1,3-bis (hydrazinocarbonoethyl) -5-isopropylhydantoin, sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
  • imidazole derivatives examples include 1-cyanoethyl-2-phenylimidazole, N- (2- (2-methyl-1-imidazolyl) ethyl) urea, 2,4-diamino-6- (2′-methylimidazolyl- (1 ′))-ethyl-s-triazine, N, N′-bis (2-methyl-1-imidazolylethyl) urea, N, N ′-(2-methyl-1-imidazolylethyl) -adipamide, 2- Examples include phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole.
  • acid anhydride examples include tetrahydrophthalic anhydride, ethylene glycol bis (anhydrotrimellitate), and the like. These thermosetting agents may be used independently and 2 or more types may be used in combination.
  • thermosetting agent As what is marketed among the said thermosetting agents, the thermosetting agent by an Otsuka Chemical company, the thermosetting agent by Ajinomoto Fine Techno Co., etc. are mentioned, for example.
  • thermosetting agent manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • thermosetting agent manufactured by Ajinomoto Fine Techno Co. include Amicure VDH, Amicure VDH-J, Amicure UDH, and the like.
  • the content of the thermosetting agent is preferably 0.5 parts by weight and preferably 30 parts by weight with respect to 100 parts by weight of the polymerizable compound. When the content of the thermosetting agent is within this range, the obtained sealing agent for organic EL display elements is more excellent in thermosetting properties while maintaining excellent storage stability.
  • the minimum with more preferable content of the said thermosetting agent is 1 weight part, and a more preferable upper limit is 15 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 alone or in combination of two or more.
  • 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 said surface modifier, the flatness of the coating film of the sealing agent for organic EL display elements of this invention can be improved further.
  • 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 surface modifiers manufactured by Big Chemie Japan, and surface modifiers manufactured by AGC Seimi Chemical.
  • Examples of the surface modifier made by Big Chemie Japan include BYK-340, BYK-345, and the like.
  • Examples of the surface modifier made by AGC Seimi Chemical include Surflon S-611.
  • 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 sensitizer and a surface modifier.
  • 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 sensitizer and a surface modifier.
  • the encapsulant for organic EL display elements of the present invention is also referred to as a curing rate after 30 minutes after irradiation with ultraviolet rays having a wavelength of 395 nm at 2000 mJ / cm 2 (hereinafter referred to as “curing rate after 30 minutes after light irradiation”). ) Is preferably 80%.
  • the curing rate after 30 minutes from the light irradiation is 80% or more, the encapsulant for organic EL display elements of the present invention can reduce the sol component and display defects are further reduced.
  • a more preferable lower limit of the curing rate 30 minutes after the light irradiation is 90%.
  • the curing rate 30 minutes after the light irradiation is most preferably 100%.
  • y is a peak area value derived from this polymerizable functional group in the hardened
  • z is a peak area value derived from the polymerizable functional group in the cured product of the sealant after being irradiated with light and heated at 80 ° C. for 1 hour.
  • the peak derived from the polymerizable functional group is, for example, the peak derived from the epoxy group (911 cm ⁇ 1 ) when the polymerizable compound is an epoxy compound, and the oxetanyl when the polymerizable compound is an oxetane compound. It is a peak derived from a group (978 cm ⁇ 1 ).
  • cured material of the sealing agent for organic EL display elements of this 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%.
  • the total light transmittance can be measured using a spectrometer such as AUTOMATIC HAZE METER MODEL TC-III DPK (manufactured by Tokyo Denshoku).
  • cured material used for the measurement of the said total light transmittance is a photocurable sealing agent, for example, it will obtain by irradiating 2000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 395 nm with a LED lamp to 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 395 nm will be 2000 mJ / cm with a LED lamp to a 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, it can obtain by irradiating 2000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 395 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 moisture content of the cured product is preferably less than 0.5% when the cured product is exposed to an environment of 85 ° C. and 85% RH for 24 hours.
  • 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 said moisture content measurement is a photocurable sealing agent, it can obtain by irradiating 2000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 395 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 sealant element of the present invention When curing the organic EL display element sealing agent of the present invention by light irradiation, the organic EL display sealant element of the present invention, 300 nm or more 400nm or less wavelength and 300 mJ / cm 2 or more 3000 mJ / cm 2 or less of It can be suitably cured by irradiating with an accumulated amount of light.
  • Examples of the light source used for the light irradiation 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, a microwave excitation mercury lamp, a metal halide lamp, a sodium lamp, a halogen lamp, and a xenon.
  • a lamp, an LED lamp, a fluorescent lamp, sunlight, an electron beam irradiation apparatus, etc. are mentioned.
  • 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.
  • the sealing agent for organic EL display elements of this invention can be used suitably for sealing of a top emission type organic EL display element.
  • the top emission type organic EL display element using the sealing agent for organic EL display elements of the present invention is also one aspect of the present invention.
  • an organic EL display element having excellent display performance can be obtained even when the sealing agent for organic EL display elements of the present invention is used for sealing a bottom emission type organic EL display element.
  • the sealing agent for organic EL display elements which can obtain the organic EL display element which is excellent in inkjet applicability
  • the top emission type organic EL display element formed using this sealing agent for organic EL display elements can be provided.
  • Examples 1 to 4 Comparative Examples 1 to 3
  • 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 ”).
  • a homodisper type stirring mixer (“Primix Corporation,“ Homodisper L type ”).
  • To 4 and Comparative Examples 1 to 3 were prepared.
  • the cured product was obtained by irradiating the obtained encapsulant for organic EL display elements with 2000 mJ / cm 2 of UV light having a wavelength of 395 nm using an LED lamp.
  • Thermal desorption device Turbo Matrix 650 (manufactured by PerkinElmer) Thermal desorption conditions: 80 ° C., 30 minutes Split: Inlet 15 mL / min, outlet 15 mL / min, injection amount 5.2% GC-MS device: JMS Q1000 (manufactured by JEOL Ltd.) Separation column: EQUITY-1 (Nonpolar) 0.32mm ⁇ 60m ⁇ 0.25 ⁇ m GC temperature rising rate: 40 ° C. for 4 minutes ⁇ 10 ° C./minute ⁇ 300° C.
  • each of the encapsulants for organic EL display elements obtained in Examples and Comparative Examples is a 10 picoliter liquid using an inkjet discharge device (“NanoPrinter500” manufactured by Microjet). With a drop amount, 1000 drops were applied at a speed of 5 m / sec on a non-alkali glass (ASA 100, manufactured by Asahi Glass Co., Ltd.) washed with alkali at a pitch of 500 ⁇ m. The diameter of the droplet on the alkali-free glass 10 minutes after the coating was measured.
  • ASA 100 non-alkali glass
  • a glass substrate (length 25 mm, width 25 mm, thickness 0.7 mm) having an ITO electrode formed in a thickness of 1000 mm A substrate was used.
  • the substrate was ultrasonically washed with acetone, an aqueous alkali solution, ion-exchanged water, and isopropyl alcohol for 15 minutes, respectively, then washed with boiled isopropyl alcohol for 10 minutes, and a UV-ozone cleaner (manufactured by Nippon Laser Electronics Co., Ltd.). The last treatment was performed with “NL-UV253”).
  • this substrate is fixed to a substrate holder of a vacuum deposition 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.
  • the dark spot diameter enlargement ratio is less than 1.1 times, “ ⁇ ”, when it is 1.1 times or more and less than 1.2 times,“ ⁇ ”, when it is 1.2 times or more and less than 1.5 times
  • the light emission state of the organic EL display element was evaluated with “ ⁇ ” as the case where it was present, 1.5 times or more, or “x” as the case where the non-light emitting portion was significantly enlarged.
  • the sealing agent for organic EL display elements which can obtain the organic EL display element which is excellent in inkjet applicability
  • the top emission type organic EL display element formed using this sealing agent for organic EL display elements can be provided.

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Abstract

L'objet de la présente invention est de fournir un agent d'étanchéité pour un élément d'affichage électroluminescent organique, qui a une excellente propriété de revêtement par jet d'encre, et au moyen duquel un élément d'affichage électroluminescent organique ayant d'excellentes performances d'affichage peut être obtenu, y compris s'il s'agit d'un type à émission par le haut. En outre, l'objet de la présente invention est de fournir un élément d'affichage électroluminescent organique de type à émission par le haut formé à l'aide de l'agent d'étanchéité pour l'élément d'affichage électroluminescent organique. La présente invention concerne un agent d'étanchéité pour un élément d'affichage électroluminescent organique, l'agent d'étanchéité contenant un composé polymérisable et un initiateur de polymérisation et ayant un retrait de durcissement inférieur à 11 %, et un produit durci associé, mesuré dans une condition de dépôt thermique de 80 °C pendant 30 minutes par un procédé GC-MS de dépôt thermique ayant une quantité de dégazage inférieure à 3 000 ppm.
PCT/JP2019/015824 2018-04-20 2019-04-11 Agent d'étanchéité pour élément d'affichage électroluminescent organique et élément d'affichage électroluminescent organique de type à émission par le haut Ceased WO2019203123A1 (fr)

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CN201980025061.4A CN111937493B (zh) 2018-04-20 2019-04-11 有机el显示元件用密封剂和顶部发射型有机el显示元件
KR1020207018042A KR20210004942A (ko) 2018-04-20 2019-04-11 유기 el 표시 소자용 봉지제 및 톱 이미션형 유기 el 표시 소자
JP2023102355A JP2023123648A (ja) 2018-04-20 2023-06-22 有機ｅｌ表示素子用封止剤及びトップエミッション型有機ｅｌ表示素子

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JP2021190428A (ja) * 2020-06-03 2021-12-13 三星エスディアイ株式会社Samsung SDI Co., Ltd. 有機発光素子封止用組成物およびこれにより製造された有機層を含む有機発光表示装置
JP7762514B2 (ja) 2020-06-03 2025-10-30 三星エスディアイ株式会社 有機発光素子封止用組成物およびこれにより製造された有機層を含む有機発光表示装置

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