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WO2019203180A1 - Agent d'étanchéité servant à un élément d'affichage el organique - Google Patents

Agent d'étanchéité servant à un élément d'affichage el organique Download PDF

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Publication number
WO2019203180A1
WO2019203180A1 PCT/JP2019/016108 JP2019016108W WO2019203180A1 WO 2019203180 A1 WO2019203180 A1 WO 2019203180A1 JP 2019016108 W JP2019016108 W JP 2019016108W WO 2019203180 A1 WO2019203180 A1 WO 2019203180A1
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WIPO (PCT)
Prior art keywords
organic
display elements
display
sealing agent
display element
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/JP2019/016108
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English (en)
Japanese (ja)
Inventor
康雄 渡邊
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
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 KR1020207007851A priority Critical patent/KR102765324B1/ko
Priority to JP2019521494A priority patent/JP7479842B2/ja
Priority to CN201980007068.3A priority patent/CN111527794B/zh
Publication of WO2019203180A1 publication Critical patent/WO2019203180A1/fr
Anticipated expiration legal-status Critical
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
    • 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
    • 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
    • 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
    • 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations

Definitions

  • the present invention relates to a sealant for an organic EL display device that can provide an organic EL display device that is excellent in coating properties, fast curing properties, low outgassing properties, storage stability, and display performance.
  • An organic electroluminescence 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 includes an organic filling layer made of an in-plane sealing agent that covers and seals a laminate having an organic light emitting material layer, and a peripheral sealing agent containing a moisture absorbent, and the organic filling layer A method of sealing an organic EL display element by a configuration having a moisture-absorbing seal layer covering the side surfaces of the organic EL display device is disclosed.
  • the present invention provides an organic EL display element sealant that can provide an organic EL display element that is excellent in coating properties, fast curability, low outgassing properties, storage stability, and display performance. With the goal.
  • the present invention contains a curable resin and a thermal cationic polymerization initiator, the curable resin contains an alicyclic epoxy compound and an oxetane compound, and a temperature increase rate of 40 ° C./min in differential scanning calorimetry.
  • the temperature from holding at 100 ° C. until the rise of the exothermic peak is 3 minutes or less, and stored for 4 days in an environment of 40 ° C. and 22.5% RH. It is the sealing agent for organic EL display elements whose viscosity increase rate after having been 20% or less.
  • the present invention is described in detail below.
  • the present inventor considers that the cause of display defects such as dark spots in the organic EL display element is that the sealing agent used generates outgas, and the organic EL display is made of a material having excellent low outgassing properties.
  • An investigation was made on sealing an organic EL display element using an element sealing agent.
  • display defects such as dark spots may occur in the obtained organic EL display element.
  • the present inventor has a laminate having an organic light emitting material layer by reducing the viscosity of the organic EL display element sealant used as an in-plane sealant upon heating such as curing. It was thought that the penetration of the organic EL display element caused the display defect.
  • the present inventor has proposed a low curable resin and thermal polymerization initiator used for the sealant in order to improve the fast curability of the sealant for organic EL display elements and prevent penetration into the laminate.
  • the obtained sealant has a problem that it tends to thicken and is inferior in storage stability. Therefore, the present inventor used a combination of an alicyclic epoxy compound and an oxetane compound as a curable resin, and further, the time until the rise of the exothermic peak when the differential scanning calorimetry of the sealant was measured, It was examined to adjust the thickening rate after storage for 4 days in an environment of 22.5% RH to a specific value or less.
  • an organic EL display element sealing agent that is excellent in all of coating properties, fast curability, low outgassing properties, and storage stability, and by using the organic EL display element sealing agent.
  • the present inventors have found that an organic EL display element having excellent display performance can be obtained, and have completed the present invention.
  • the sealing agent for organic EL display elements of the present invention is heated at a rate of 40 ° C./min in differential scanning calorimetry, held at 100 ° C. when held at 100 ° C., and until the rise of the exothermic peak.
  • the time (hereinafter also referred to as “curing start time”) is 3 minutes or less.
  • the hardening start time is 3 minutes or less, the sealing agent for organic EL display elements of this invention is excellent in quick curability, and the obtained organic EL display element becomes excellent in display performance.
  • the curing start time is preferably 2.5 minutes or less, and more preferably 2 minutes or less.
  • the differential scanning calorimetry was performed using a differential scanning calorimeter and a holding temperature of 100 ° C.
  • differential scanning calorimeter in an environment of 25 ° C. and 50% RH for 10 mg of sealant placed in an aluminum pan. It can be measured under the measurement condition of ° C.
  • Examples of the differential scanning calorimeter include Thermo plus DSC 8230 (manufactured by Rigaku).
  • the sealing agent for organic EL display elements of the present invention has a viscosity increase rate of 20% or less after storage for 4 days in an environment of 40 ° C. and 22.5% RH.
  • the viscosity increase rate is preferably 15% or less, more preferably 10% or less, and most preferably 0%.
  • thickening rate means that the viscosity immediately after production (before storage) is A, and the viscosity after storage for 4 days in an environment of 40 ° C. and 22.5% RH is B. It is a value calculated by the following formula.
  • Thickening rate (%) ((BA) ⁇ A) ⁇ 100
  • the “viscosity” means a value measured using an E-type viscometer under the conditions of 25 ° C. and 20 rpm.
  • the E-type viscometer include VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.), and a CP1 cone plate can be used.
  • the above-mentioned curing start time and the above thickening rate are the ranges described above by selecting these types and adjusting the content ratios of other components such as a curable resin, a thermal cationic polymerization initiator, and a stabilizer described later. It can be.
  • the sealing agent for organic EL display elements of this invention contains curable resin.
  • the curable resin contains an alicyclic epoxy compound and an oxetane compound.
  • the resulting organic EL display element encapsulant is inferior in fast curability or the like.
  • Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl (meth) acrylate, 1,2: 8,9-diepoxy limonene, 4-vinylcyclohexene monooxide, vinylcyclohexene dioxide, and methylated vinyl.
  • Cyclohexene dioxide (3,4-epoxycyclohexyl) methyl-3,4-epoxycyclohexylcarboxylate, bis (3,4-epoxycyclohexylmethyl) ether, 3,4,3 ′, 4′-diepoxycyclohexyl, Examples thereof include bis (3,4-epoxycyclohexyl) adipate, bis (2,3-epoxycyclopentyl) ether, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, and dicyclopentadiene dioxide.
  • the alicyclic epoxy compound is 3,4-epoxycyclohexylmethyl (meth) acrylate is preferably contained.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • oxetane compound examples include 4,4′-bis ((3-ethyl-3-oxetanyl) methoxymethyl) biphenyl and 3-ethyl-3-(((3-ethyloxetane-3-yl) methoxy) methyl.
  • the oxetane compound comprises at least 4,4′-bis ((3-ethyl-3-oxetanyl) methoxymethyl) biphenyl and 3-ethyl-3-(((3-ethyloxetane-3-yl) methoxy) methyl) oxetane. It is preferable to include any of them.
  • the minimum with the preferable content rate of the said alicyclic epoxy compound in the sum total of the said alicyclic epoxy compound and the said oxetane compound is 20 weight%, and a preferable upper limit is 80 weight%.
  • a preferable upper limit is 80 weight%.
  • the minimum with more preferable content rate of the said alicyclic epoxy compound is 30 weight%, and a more preferable upper limit is 70 weight%.
  • the said curable resin may contain other curable resin for the purpose of viscosity adjustment etc. in the range which does not inhibit the objective of this invention.
  • other curable resin other epoxy compounds other than the said alicyclic epoxy compound, a vinyl ether compound, etc. are mentioned, for example.
  • the other epoxy compounds include dicyclopentadiene dimethanol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, and the like. .
  • 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 this invention contains a thermal cationic polymerization initiator.
  • the anion portion (counter anion) is BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is at least two fluorines or trifluoro And a sulfonium salt, a phosphonium salt, an ammonium salt, etc., which represent a phenyl group substituted with a methyl group.
  • the quaternary in which the counter anion is a borate system.
  • Ammonium salts (hereinafter also referred to as “borate quaternary ammonium salts”) are preferred.
  • the counter anion of the borate quaternary ammonium salt is preferably BF 4 - or (BX 4 ) - .
  • 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).
  • dimethylphenyl (4-methoxybenzyl) ammonium tetrakis is more easily adjusted for the curing start time and the thickening rate of the obtained sealing agent for organic EL display elements and excellent in low outgassing properties.
  • (Pentafluorophenyl) borate is preferred.
  • 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.
  • the content of the thermal 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 curable resin.
  • the minimum with more preferable content of the said thermal 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 this invention may contain a thermosetting agent in the range which does not inhibit the objective of this invention.
  • 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 (hydrazinocarboethyl) -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 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 curable resin. When the content of the thermosetting agent is within this range, the obtained sealant for an organic EL display element sealant is more excellent in thermosetting 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 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 preferable lower limit of the content of the stabilizer is 0.001 part by weight and the preferable upper limit is 2 parts by weight with respect to 100 parts by weight of the curable resin.
  • 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 fast 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 curable resin.
  • 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 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.
  • You may contain a compound or an ion exchange resin.
  • Examples of the compound that reacts with the generated acid include substances that neutralize the acid, such as carbonates or bicarbonates of alkali metals, carbonates or bicarbonates of alkaline earth metals, and the like.
  • substances that neutralize the acid such as carbonates or bicarbonates of alkali metals, carbonates or bicarbonates of alkaline earth metals, and the like.
  • 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.
  • the sealing agent for organic EL display elements of this invention does not contain a solvent from a viewpoint of suppressing generation
  • the sealing agent for organic EL display elements of the present invention for example, using a mixer such as a homodisper, homomixer, universal mixer, planetary mixer, kneader, three rolls, And a method of mixing a thermal cationic polymerization initiator and an additive such as a stabilizer or a silane coupling agent added as necessary.
  • a mixer such as a homodisper, homomixer, universal mixer, planetary mixer, kneader, three rolls, and a method of mixing a thermal 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 a preferred lower limit of 10 mPa ⁇ s and a preferred upper limit of 500 mPa ⁇ s measured using an E-type viscometer at 25 ° C. and 20 rpm.
  • the viscosity is within this range, the obtained sealing agent for organic EL display elements is excellent in applicability and is particularly suitable as an in-plane sealing agent for organic EL display elements.
  • a more preferable lower limit of the viscosity is 30 mPa ⁇ s, and a more preferable upper limit is 250 mPa ⁇ s.
  • 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 EL display elements which can obtain the organic EL display element which is excellent in applicability
  • Examples 1 to 8, Comparative Examples 1 to 9 According to the blending ratios described in Tables 1 and 2, the materials were uniformly stirred and mixed at a stirring speed of 3000 rpm using a stirring mixer (“AR-250” manufactured by Shinky Corporation). Sealants for organic EL display elements of Comparative Examples 1 to 9 were prepared. 10 mg of the obtained sealing agent for organic EL display element was put in an aluminum pan, and the temperature was increased by using a differential scanning calorimeter (manufactured by Rigaku, “Thermo plus DSC 8230”) in an environment of 25 ° C. and 50% RH. Differential scanning calorimetry was performed under the measurement conditions of a temperature rate of 40 ° C./min and a holding temperature of 100 ° C.
  • a differential scanning calorimeter manufactured by Rigaku, “Thermo plus DSC 8230”
  • Tables 1 and 2 show the time from the holding at 100 ° C. to the rise of the exothermic peak (curing start time). Moreover, about the obtained sealing agent for organic EL display elements, the viscosity immediately after manufacture (before storage) and the viscosity after storage for 4 days in an environment of 40 ° C. and 22.5% RH are measured. The thickening rate was calculated from the formula. The results are shown in Tables 1 and 2. In addition, what was gelatinized was described as "gel” instead of the value of the viscosity. The viscosity was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”) on a CP1 type cone plate at 25 ° C. and 20 rpm.
  • E-type viscometer manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”
  • 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 put into an unglazed crucible in other different ways.
  • 200 mg of tris (8-quinolinolato) aluminum (Alq 3 ) was put in an unglazed crucible, and the inside of the vacuum chamber was depressurized 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 aluminum is added to another tungsten boat. 1.0 g of wire 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.
  • E-W207 (manufactured by Sekisui Chemical Co., Ltd.) is applied to the outer periphery of the substrate on which the laminate is placed so that the line width is 6 mm. After applying each sealing agent for organic EL display elements obtained in the example so as to cover the entire laminate, another glass substrate (length 45 mm, width 45 mm, thickness 0.7 mm) was overlaid. Then, 3000 mJ / cm ⁇ 2 > ultraviolet-ray was irradiated, and also in-plane sealing agent and periphery sealing agent were hardened by heating at 100 degreeC for 30 minutes, and produced the organic EL display element.
  • the sealing agent for organic EL display elements which can obtain the organic EL display element which is excellent in applicability

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyethers (AREA)

Abstract

La présente invention vise à fournir un agent d'étanchéité servant à des éléments d'affichage EL organiques qui présente d'excellentes propriétés de revêtement, une aptitude au durcissement rapide, de faibles propriétés de dégazage et une excellente stabilité de stockage, et qui permet d'obtenir des éléments d'affichage EL organiques dotés d'excellentes propriétés d'affichage. La présente invention concerne un agent d'étanchéité servant à un élément d'affichage EL organique qui comprend une résine durcissable et un initiateur de polymérisation cationique thermique, la résine durcissable comprenant un composé époxy alicyclique et un composé oxétane, le temps jusqu'à élévation d'un pic exothermique après maintien à 100 °C quand la température de la résine durcissable est élevée à une vitesse d'augmentation de température de 40 °C/minute et maintenue à 100 °C, mesurée par analyse enthalpique différentielle, étant inférieur ou égal à 3 minutes, et le taux d'augmentation de viscosité après stockage pendant 4 jours dans un environnement de 40 °C et de 22,5 % RH étant inférieur ou égale à 20 %.
PCT/JP2019/016108 2018-04-20 2019-04-15 Agent d'étanchéité servant à un élément d'affichage el organique Ceased WO2019203180A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020207007851A KR102765324B1 (ko) 2018-04-20 2019-04-15 유기 el 표시 소자용 봉지제
JP2019521494A JP7479842B2 (ja) 2018-04-20 2019-04-15 有機ｅｌ表示素子用封止剤
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