WO2018052007A1 - 有機エレクトロルミネッセンス表示素子用封止剤 - Google Patents
有機エレクトロルミネッセンス表示素子用封止剤 Download PDFInfo
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- WO2018052007A1 WO2018052007A1 PCT/JP2017/032994 JP2017032994W WO2018052007A1 WO 2018052007 A1 WO2018052007 A1 WO 2018052007A1 JP 2017032994 W JP2017032994 W JP 2017032994W WO 2018052007 A1 WO2018052007 A1 WO 2018052007A1
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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
- 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
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- 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
- C08G59/68—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 catalysts used
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- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
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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
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- 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
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- 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
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- 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 a sealant for an organic electroluminescence display element having excellent adhesion to a substrate, low outgassing property, anti-discoloration property, and coating property.
- An organic electroluminescence EL display element (organic EL display element) has a thin film structure in which an organic light emitting material layer is sandwiched between a pair of electrodes facing each other. When electrons are injected from one electrode into the organic light emitting material layer and holes are injected from the other electrode, electrons and holes are combined in the organic light emitting material layer to perform self-light emission. Compared with a liquid crystal display element or the like that requires a backlight, the visibility is better, the thickness can be reduced, and direct current low voltage driving is possible.
- an organic EL display element has a problem that when the organic light emitting material layer and the electrode are exposed to the outside air, the light emission characteristics thereof are rapidly deteriorated and the life is shortened. Therefore, for the purpose of improving the stability and durability of the organic EL display element, in the organic EL display element, a sealing technique for shielding the organic light emitting material layer and the electrode from moisture and oxygen in the atmosphere is indispensable. Yes.
- Patent Document 1 discloses a method of filling a photocurable adhesive between organic EL display element substrates in a top emission organic EL display element or the like, and irradiating light to seal.
- a photocurable adhesive has a problem in that an outgas is generated at the time of light irradiation to deteriorate the element, or the coating property is inferior.
- An object of this invention is to provide the sealing agent for organic electroluminescent display elements which is excellent in the adhesiveness with respect to a board
- the present invention relates to an organic electroluminescence display element sealing agent comprising a cationically polymerizable compound and a cationic polymerization initiator, wherein a cycloalkene oxide type alicyclic epoxy compound is added to 100 parts by weight of the cationically polymerizable compound.
- An encapsulant for organic electroluminescence display elements which is contained in an amount of 50 parts by weight or more and 80 parts by weight or less and has a viscosity of 400 mPa ⁇ s or less measured at 25 ° C. and 20 rpm using an E-type viscometer. The present invention is described in detail below.
- the present inventor has studied to prevent outgassing by using a cycloalkene oxide type alicyclic epoxy compound as a cationically polymerizable compound in a sealing agent for organic EL display elements.
- a cycloalkene oxide type alicyclic epoxy compound as a cationically polymerizable compound in a sealing agent for organic EL display elements.
- the resulting sealant may be inferior in adhesion to the substrate or coating properties, or may turn yellow. Therefore, as a result of further intensive studies, the present inventor has determined that the content of the cycloalkene oxide type alicyclic epoxy compound and the viscosity of the entire sealant are in a specific range, so that adhesion to the substrate, low outgassing, and prevention of discoloration are achieved.
- the present invention has been completed by finding that an organic EL display element sealing agent having excellent properties and applicability can be obtained.
- the sealing agent for organic EL display elements of this invention contains a cationically polymerizable compound.
- the cationically polymerizable compound contains a cycloalkene oxide type alicyclic epoxy compound.
- the sealing agent for organic EL display elements of this invention will be excellent in low outgassing property.
- Examples of the cycloalkene oxide type alicyclic epoxy compound include 3 ', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (3,4-epoxycyclohexylmethyl) ether, and the like. Especially, it is preferable that the said cycloalkene oxide type alicyclic epoxy compound has an ether bond or ester bond other than what is contained in an epoxy group, and has a cycloalkene oxide group in both ends.
- cycloalkene oxide type alicyclic epoxy compounds those commercially available include Celoxide 2021P (manufactured by Daicel).
- the lower limit of the content of the cycloalkene oxide type alicyclic epoxy compound in 100 parts by weight of the whole cationic polymerizable compound is 50 parts by weight, and the upper limit is 80 parts by weight.
- the content of the cycloalkene oxide type alicyclic epoxy compound is within this range, the obtained sealing agent for organic EL display elements is excellent in adhesion and coating properties to the substrate and is suitable as an in-plane sealing agent. It will be something.
- the minimum with preferable content of the said cycloalkene oxide type alicyclic epoxy compound is 60 weight part, a preferable upper limit is 78 weight part, a more preferable minimum is 70 weight part, and a more preferable upper limit is 75 weight part.
- the cationic polymerizable compound contains other cationic polymerizable compounds in addition to the cycloalkene oxide type alicyclic epoxy compound.
- the other cationic polymerizable compounds include bis ((3-ethyloxetane-3-yl) methyl) ether, 1,2: 7,8-diepoxyoctane, and 1,2: 5,6-diepoxy. At least one selected from the group consisting of cyclooctane is preferably used. Of these, bis ((3-ethyloxetane-3-yl) methyl) ether is preferable.
- the cationic polymerizable compound In 100 parts by weight of the cationic polymerizable compound, the bis ((3-ethyloxetane-3-yl) methyl) ether, the 1,2: 7,8-diepoxyoctane, and the 1,2: 5,
- the preferable lower limit of the content of at least one selected from the group consisting of 6-diepoxycyclooctane is 10 parts by weight, and the preferable upper limit is 50 parts by weight.
- the obtained sealing agent for organic EL display elements is more excellent in adhesion and coating properties to the substrate.
- the more preferred lower limit of the content of at least one kind is 20 parts by weight, the more preferred upper limit is 30 parts by weight, the still more preferred lower limit is 23 parts by weight, and the still more preferred upper limit is 27 parts by weight.
- the cycloalkene oxide type alicyclic epoxy compound, the bis ((3-ethyloxetane-3-yl) methyl) ether, and the 1,2,7,8-di in 100 parts by weight of the cationic polymerizable compound is 80 parts by weight.
- the cycloalkene oxide type alicyclic epoxy compound, the bis ((3-ethyloxetane-3-yl) methyl) ether, the 1,2,7,8-diepoxyoctane, and the 1,2: 5 A more preferred lower limit of the total content of at least one selected from the group consisting of, 6-diepoxycyclooctane is 90 parts by weight, and a more preferred lower limit is 99 parts by weight.
- the sealing agent for organic EL display elements of the present invention contains a cationic polymerization initiator.
- the cationic polymerization initiator include a thermal cationic polymerization initiator that generates a protonic acid or a Lewis acid by heating, and a photocationic polymerization initiator that generates a protonic acid or a Lewis acid by light irradiation. It may be a nonionic acid generation type.
- thermal cationic polymerization initiator examples include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is phenyl substituted with at least two fluorine or trifluoromethyl groups.
- a sulfonium salt, a phosphonium salt, a quaternary ammonium salt, a diazonium salt, or an iodonium salt, and a sulfonium salt is more preferable.
- sulfonium salts include triphenylsulfonium boron tetrafluoride, triphenylsulfonium hexafluoride antimony, triphenylsulfonium hexafluoride arsenic, tri (4-methoxyphenyl) sulfonium hexafluoride arsenic, and diphenyl (4-phenylthiophenyl). ) Sulfonium arsenic hexafluoride and the like.
- the phosphonium salt include ethyltriphenylphosphonium antimony hexafluoride and tetrabutylphosphonium antimony hexafluoride.
- Examples of the quaternary ammonium salt include dimethylphenyl (4-methoxybenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methoxybenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methoxybenzyl) ammonium tetrakis (penta).
- Fluorophenyl) borate dimethylphenyl (4-methylbenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methylbenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorotetrakis (pentafluorophenyl) borate , Methylphenyldibenzylammonium, methylphenyldibenzylammonium hexafluoroantimony Hexafluorophosphate, methylphenyldibenzylammonium tetrakis (pentafluorophenyl) borate, phenyltribenzylammonium tetrakis (pentafluorophenyl) borate, dimethylphenyl (3,4-dimethylbenzyl) ammonium tetrakis (pentafluorophenyl) borate, N, N-
- 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.). CXC-1612, CXC-1738, CXC-1821 (all manufactured by King Industries), and the like.
- ionic photoacid generating types include, for example, that the anion moiety is BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is at least An aromatic sulfonium salt, an aromatic iodonium salt, an aromatic diazonium salt, an aromatic ammonium salt, or (2,4, which represents a phenyl group substituted with two or more fluorine or trifluoromethyl groups) -Cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe salt and the like.
- 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 generators include, for example, nitrobenzyl esters, sulfonic acid derivatives, phosphoric acid esters, phenol sulfonic acid esters, diazonaphthoquinone, N-hydroxyimide sulfonates, and the like. Can be mentioned.
- 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), IRGACURE290 (from BASF), PI 2074 (from Rhodia), and the like.
- a quaternary ammonium salt whose counter anion is borate (hereinafter also referred to as “borate quaternary ammonium salt”) is preferably used.
- the counter anion of the borate quaternary ammonium salt is BF 4 ⁇ or (BX 4 ) ⁇ (where X represents a phenyl group substituted with at least two fluorine or trifluoromethyl groups). It is preferable.
- the content of the cationic polymerization initiator is preferably 0.05 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
- the content of the cationic polymerization initiator is within this range, the obtained sealing agent for organic EL display elements is excellent in curability, storage stability, and moisture resistance of the cured product.
- the minimum with more preferable content of the said cationic polymerization initiator is 0.1 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 thermosetting agent.
- 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.
- hydrazide compound examples 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 together.
- thermosetting agents examples include SDH (manufactured by Nippon Finechem Co., Ltd.), ADH (manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH (all manufactured by Ajinomoto Fine Techno Co., Ltd.). ) 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 cationic polymerizable compound.
- the content of the thermosetting agent is 0.5 parts by weight or more, the obtained sealing agent for organic EL display elements is more excellent in thermosetting.
- the content of the thermosetting agent is 30 parts by weight or less, the obtained sealing agent for organic EL display elements is excellent in storage stability, and the cured product is excellent in moisture resistance.
- 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 this invention contains a stabilizer. By containing the said stabilizer, the sealing agent for organic EL display elements of this invention becomes a thing excellent in storage stability more.
- the stabilizer examples include amine compounds such as benzylamine and aminophenol type epoxy resins.
- the content of the stabilizer is preferably 0.001 part by weight and preferably 2 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
- the content of the stabilizer is within this range, the obtained sealing agent for organic EL display elements is more excellent in storage stability while maintaining excellent curability.
- the minimum with more preferable content of the said stabilizer is 0.005 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 cationic polymerizable compound.
- 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 content of the silane coupling agent is preferably 0.5 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound, and more preferably 0.1%. Parts by weight, and a more preferred upper limit is 0.01 parts by weight.
- the sealing agent for organic EL display elements of the present invention may 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.
- the surface modifier include surfactants and leveling agents.
- Examples of the surface modifier include silicone-based, acrylic-based, and fluorine-based ones.
- Examples of commercially available surface modifiers include BYK-300, BYK-302, BYK-331 (all manufactured by Big Chemie Japan), UVX-272 (manufactured by Enomoto Kasei), Surflon. S-611 (manufactured by AGC Seimi Chemical Co., Ltd.) and the like.
- the encapsulant for organic EL display elements of the present invention reacts with the acid generated in the encapsulant for organic EL display elements in order to improve the durability of the element electrode within a range not impairing the object of the present invention.
- a compound or an ion exchange resin may be contained.
- Examples of the compound that reacts with the generated acid include substances that neutralize the acid, for example, alkali metal carbonates or bicarbonates, or alkaline earth metal carbonates or bicarbonates.
- alkali metal carbonates or bicarbonates or alkaline earth metal carbonates or bicarbonates.
- calcium carbonate, calcium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate and the like are used.
- any of a cation exchange type, an anion exchange type, and a both ion exchange type can be used, and in particular, a cation exchange type or a both ion exchange type capable of adsorbing chloride ions. Is preferred.
- the sealing agent for organic EL display elements of this invention is a range which does not inhibit the objective of this invention, and is a hardening retarder, a reinforcing agent, a softener, a plasticizer, a viscosity modifier, and an ultraviolet absorber as needed. Further, various known additives such as antioxidants may be contained.
- Examples of the method for producing the sealing agent for organic EL display elements of the present invention include a cationically polymerizable compound using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll. And a method of mixing a cationic polymerization initiator and an additive such as a stabilizer or a silane coupling agent added as necessary.
- a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll.
- a method of mixing a cationic polymerization initiator and an additive such as a stabilizer or a silane coupling agent added as necessary.
- the sealing agent for organic EL display elements of the present invention has an upper limit of viscosity of 400 mPa ⁇ s measured using an E-type viscometer under the conditions of 25 ° C. and 20 rpm.
- the viscosity is 400 mPa ⁇ s or less, the obtained sealing agent for organic EL display elements is excellent in coatability and is suitable as an in-plane sealing agent for organic EL display elements.
- a preferable upper limit of the viscosity is 250 mPa ⁇ s, and a more preferable upper limit is 100 mPa ⁇ s.
- the minimum with the said preferable viscosity is 5 mPa * s.
- the E-type viscometer for example, VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) can be used, and it can be measured with a CP1 cone plate.
- the sealing agent for organic EL display elements of the present invention is particularly preferably used as an in-plane sealing agent that covers and seals a laminate having an organic light emitting material layer.
- the sealing agent for organic electroluminescent display elements which is excellent in the adhesiveness with respect to a board
- Examples 1 to 7, Comparative Examples 1 and 2 Each material listed in Table 1 was stirred and mixed at a stirring speed of 3000 rpm using a stirring mixer (“AR-250”, manufactured by Shinky Corporation) according to the blending ratio described in Table 1. 7.
- the sealing agent for organic EL display elements of Comparative Examples 1 and 2 was produced.
- Viscosity About each sealing agent for organic EL display elements obtained in Examples and Comparative Examples, using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”), 25 ° C., 20 rpm The viscosity was measured under the following conditions.
- the sealant obtained in Example 7 was irradiated with 3000 mJ / cm 2 of ultraviolet light instead of being heated in a 100 ° oven for 30 minutes, and then cured in an 80 ° C. oven for 30 minutes to obtain an adhesive test piece. It was.
- the peel adhesion strength of the obtained adhesion test piece was measured using an indentation tester. As a result, when the peel adhesive strength was 5.0 kgf / cm 2 or more, “ ⁇ ”, when 2.5 kgf / cm 2 or more and less than 5.0 kgf / cm 2 , “ ⁇ ”, 2.5 kgf / cm The case where it was less than cm 2 was evaluated as “x”, and the adhesion to the substrate was evaluated.
- the sealing agent for organic electroluminescent display elements which is excellent in the adhesiveness with respect to a board
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Abstract
Description
以下に本発明を詳述する。
上記カチオン重合性化合物は、シクロアルケンオキシド型脂環式エポキシ化合物を含有する。上記シクロアルケンオキシド型脂環式エポキシ化合物を含有することにより、本発明の有機EL表示素子用封止剤は、低アウトガス性に優れるものとなる。
上記その他のカチオン重合性化合物としては、ビス((3-エチルオキセタン-3-イル)メチル)エーテル、1,2:7,8-ジエポキシオクタン、及び、1,2:5,6-ジエポキシシクロオクタンからなる群より選択される少なくとも1種が好適に用いられる。なかでも、ビス((3-エチルオキセタン-3-イル)メチル)エーテルが好ましい。
上記カチオン重合開始剤としては、加熱によりプロトン酸又はルイス酸を発生する熱カチオン重合開始剤や、光照射によりプロトン酸又はルイス酸を発生する光カチオン重合開始剤が挙げられ、イオン性酸発生型であってもよいし、非イオン性酸発生型であってもよい。
上記ホスホニウム塩としては、エチルトリフェニルホスホニウム六フッ化アンチモン、テトラブチルホスホニウム六フッ化アンチモン等が挙げられる。
上記第4級アンモニウム塩としては、例えば、ジメチルフェニル(4-メトキシベンジル)アンモニウムヘキサフルオロホスフェート、ジメチルフェニル(4-メトキシベンジル)アンモニウムヘキサフルオロアンチモネート、ジメチルフェニル(4-メトキシベンジル)アンモニウムテトラキス(ペンタフルオロフェニル)ボレート、ジメチルフェニル(4-メチルベンジル)アンモニウムヘキサフルオロホスフェート、ジメチルフェニル(4-メチルベンジル)アンモニウムヘキサフルオロアンチモネート、ジメチルフェニル(4-メチルベンジル)アンモニウムヘキサフルオロテトラキス(ペンタフルオロフェニル)ボレート、メチルフェニルジベンジルアンモニウム、メチルフェニルジベンジルアンモニウムヘキサフルオロアンチモネートヘキサフルオロホスフェート、メチルフェニルジベンジルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート、フェニルトリベンジルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート、ジメチルフェニル(3,4-ジメチルベンジル)アンモニウムテトラキス(ペンタフルオロフェニル)ボレート、N,N-ジメチル-N-ベンジルアニリニウム六フッ化アンチモン、N,N-ジエチル-N-ベンジルアニリニウム四フッ化ホウ素、N,N-ジメチル-N-ベンジルピリジニウム六フッ化アンチモン、N,N-ジエチル-N-ベンジルピリジニウムトリフルオロメタンスルホン酸等が挙げられる。
上記イミダゾール誘導体としては、例えば、1-シアノエチル-2-フェニルイミダゾール、N-(2-(2-メチル-1-イミダゾリル)エチル)尿素、2,4-ジアミノ-6-(2’-メチルイミダゾリル-(1’))-エチル-s-トリアジン、N,N’-ビス(2-メチル-1-イミダゾリルエチル)尿素、N,N’-(2-メチル-1-イミダゾリルエチル)-アジポアミド、2-フェニル-4-メチル-5-ヒドロキシメチルイミダゾール、2-フェニル-4,5-ジヒドロキシメチルイミダゾール等が挙げられる。
上記酸無水物としては、例えば、テトラヒドロ無水フタル酸、エチレングリコールビス(アンヒドロトリメリテート)等が挙げられる。
これらの熱硬化剤は、単独で用いられてもよいし、2種以上が併用されてもよい。
また、低アウトガス性の観点からは、上記シランカップリング剤の含有量は、上記カチオン重合性化合物100重量部に対して、好ましい上限が0.5重量部であり、より好ましい上限が0.1重量部であり、更に好ましい上限が0.01重量部である。
上記表面改質剤としては、例えば、界面活性剤やレベリング剤等が挙げられる。
上記表面改質剤のうち市販されているものとしては、例えば、BYK-300、BYK-302、BYK-331(いずれも、ビックケミー・ジャパン社製)、UVX-272(楠本化成社製)、サーフロンS-611(AGCセイミケミカル社製)等が挙げられる。
また、上記粘度の好ましい下限は5mPa・sである。
なお、上記E型粘度計としては、例えば、VISCOMETER TV-22(東機産業社製)を用いることができ、CP1のコーンプレートにて測定することができる。
表1に記載された各材料を、表1に記載された配合比に従い、撹拌混合機(シンキー社製、「AR-250」)を用い、撹拌速度3000rpmで撹拌混合して、実施例1~7、比較例1、2の有機EL表示素子用封止剤を作製した。
実施例及び比較例で得られた各有機EL表示素子用封止剤について以下の評価を行った。結果を表1に示した。
実施例及び比較例で得られた各有機EL表示素子用封止剤について、E型粘度計(東機産業社製、「VISCOMETER TV-22」)を用いて、25℃、20rpmの条件における粘度を測定した。
ピペットを用いて実施例及び比較例で得られた各有機EL表示素子用封止剤0.1mLをガラス基板上に塗布し、1分後に広がった直径を測定した。直径が15mm以上であった場合を「○」、10mm以上15mm未満であった場合を「△」、10mm未満であった場合を「×」として、塗布性を評価した。
100μm厚みのPETフィルムで作製した型に実施例及び比較例で得られた各有機EL表示素子用封止剤を入れ、100℃オーブンで30分加熱することにより封止剤を硬化させた後、PETフィルムを剥がすことにより試験片を得た。
得られた試験片について、分光光度計(日立ハイテクサイエンス社製、「U-3900」)を用いて、350~800nmの波長における透過率を測定し、イエローインデックス(YI)値を導出した。YI値が2.5未満であった場合を「○」、2.5以上5.0未満であった場合を「△」、5.0以上であった場合を「×」として、変色防止性を評価した。
実施例及び比較例で得られた各有機EL表示素子用封止剤100重量部に対して、平均粒子径10μmのポリマービーズ(積水化学工業社製、「ミクロパールSP」)0.3重量部を遊星式撹拌装置によって分散させて均一な液とした。得られた液を2枚のガラス基板のうちの一方の中央部にとり、もう一方のガラス基板を重ね合わせて封止剤を押し広げ、100度オーブンで30分加熱して硬化させて接着試験片を得た。実施例7で得られた封止剤については、100度オーブンで30分加熱する代わりに3000mJ/cm2の紫外線を照射した後、80℃オーブンで30分加熱して硬化させ接着試験片を得た。得られた接着試験片について押し込み試験機を用いて剥離接着強度を測定した。その結果、剥離接着強度が5.0kgf/cm2以上であった場合を「○」、2.5kgf/cm2以上5.0kgf/cm2未満であった場合を「△」、2.5kgf/cm2未満であった場合を「×」として、基板に対する密着性を評価した。
実施例及び比較例で得られた各有機EL表示素子用封止剤を、バイアル瓶中に300mg計量して封入した後、100℃で30分間加熱を行うことで硬化させた。更に、このバイアル瓶を85℃の恒温オーブンで100時間加熱し、バイアル瓶中の気化成分を、ガスクロマトグラフ質量分析計(日本電子社製、「JMS-Q1050」)を用いて測定した。
気化成分量が50ppm未満であった場合を「○」、50ppm以上100ppm未満であった場合を「△」、100ppm以上であった場合を「×」として低アウトガス性を評価した。
Claims (7)
- カチオン重合性化合物とカチオン重合開始剤とを含有する有機エレクトロルミネッセンス表示素子用封止剤であって、
前記カチオン重合性化合物100重量部中にシクロアルケンオキシド型脂環式エポキシ化合物を50重量部以上80重量部以下含有し、
E型粘度計を用いて25℃、20rpmの条件で測定した粘度が400mPa・s以下である
ことを特徴とする有機エレクトロルミネッセンス表示素子用封止剤。 - シクロアルケンオキシド型脂環式エポキシ化合物は、エポキシ基に含まれる以外のエーテル結合、又は、エステル結合を有し、かつ、シクロアルケンオキシド基を両末端に有することを特徴とする請求項1記載の有機エレクトロルミネッセンス表示素子用封止剤。
- カチオン重合性化合物は、ビス((3-エチルオキセタン-3-イル)メチル)エーテル、1,2:7,8-ジエポキシオクタン、及び、1,2:5,6-ジエポキシシクロオクタンからなる群より選択される少なくとも1種を含有することを特徴とする請求項1又は2記載の有機エレクトロルミネッセンス表示素子用封止剤。
- カチオン重合性化合物100重量部中における、ビス((3-エチルオキセタン-3-イル)メチル)エーテル、1,2:7,8-ジエポキシオクタン、及び、1,2:5,6-ジエポキシシクロオクタンからなる群より選択される少なくとも1種の含有量が、10重量部以上50重量部以下であることを特徴とする請求項3記載の有機エレクトロルミネッセンス表示素子用封止剤。
- カチオン重合性化合物100重量部中おける、シクロアルケンオキシド型脂環式エポキシ化合物と、ビス((3-エチルオキセタン-3-イル)メチル)エーテル、1,2:7,8-ジエポキシオクタン、及び、1,2:5,6-ジエポキシシクロオクタンからなる群より選択される少なくとも1種との合計の含有量が、80重量部以上であることを特徴とする請求項3又は4記載の有機エレクトロルミネッセンス表示素子用封止剤。
- カチオン重合性化合物は、ビス((3-エチルオキセタン-3-イル)メチル)エーテルを含有することを特徴とする請求項3、4又は5記載の有機エレクトロルミネッセンス表示素子用封止剤。
- カチオン重合開始剤として、対アニオンがボレート系である第4級アンモニウム塩を含有することを特徴とする請求項1、2、3、4、5又は6記載の有機エレクトロルミネッセンス表示素子用封止剤。
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