WO2019188805A1 - Agent d'étanchéité d'élément d'affichage électroluminescent organique - Google Patents

Agent d'étanchéité d'élément d'affichage électroluminescent organique Download PDF

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Publication number
WO2019188805A1
WO2019188805A1 PCT/JP2019/012141 JP2019012141W WO2019188805A1 WO 2019188805 A1 WO2019188805 A1 WO 2019188805A1 JP 2019012141 W JP2019012141 W JP 2019012141W WO 2019188805 A1 WO2019188805 A1 WO 2019188805A1
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Prior art keywords
organic
sealing agent
substrate
examples
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PCT/JP2019/012141
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English (en)
Japanese (ja)
Inventor
山本　拓也
七里　徳重
千鶴 金
美香 笹野
良平 増井
由季 西海
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積水化学工業株式会社
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Application filed by 積水化学工業株式会社 filed Critical 積水化学工業株式会社
Priority to KR1020207018789A priority Critical patent/KR20200136878A/ko
Priority to CN201980021211.4A priority patent/CN111972046A/zh
Priority to JP2019521508A priority patent/JP7474052B2/ja
Publication of WO2019188805A1 publication Critical patent/WO2019188805A1/fr
Priority to JP2023196812A priority patent/JP2024019191A/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2003/1034—Materials or components characterised by specific properties
    • 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

Definitions

  • the present invention relates to a sealing agent for organic EL display elements that is excellent in applicability to a substrate or an inorganic material film even when it is thinned.
  • 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.
  • Patent Document 1 discloses a method of sealing an organic light emitting material layer and an electrode of an organic EL display element with a laminated film of a silicon nitride film and a resin film formed by a CVD method.
  • the resin film has a role of preventing pressure on the organic layer and the electrode due to internal stress of the silicon nitride film.
  • Patent Document 2 discloses a method of alternately depositing an inorganic material film and a resin film.
  • Patent Document 3 and Patent Document 4 Discloses a method of forming a resin film on an inorganic material film.
  • a method for forming a resin film there is a method in which a sealing agent is applied on a substrate using an inkjet method and then the sealing agent is cured. If such a coating method by the ink jet method is used, a resin film can be uniformly formed at high speed.
  • a resin film can be uniformly formed at high speed.
  • the organic EL display element sealant since there is a need for flexibility in using an organic EL display element by making it curved or folded, it is also necessary for the organic EL display element sealant to correspond to the flexibility.
  • the sealing agent for organic EL display elements it is conceivable to make the sealing agent into a thin film, but the conventional sealing agent is applied when the film is made into a thin film by an inkjet method or the like.
  • An object of this invention is to provide the sealing agent for organic EL display elements which is excellent in the applicability
  • Invention 1 contains a curable resin and a polymerization initiator, has a surface tension at 25 ° C. of 25 mN / m or more and 38 mN / m or less, and a surface free energy of 70 mN / m or more and 80 mN / m or less.
  • the sealant for organic EL display elements has a contact angle at 25 ° C. of 2 substrates and a SiN substrate having a surface free energy of 50 mN / m or more and 60 mN / m or less of 13 degrees or less.
  • the present invention 2 is a sealant for an organic EL display element used for coating by an ink jet method, which contains a curable resin and a polymerization initiator, and has a surface tension at 25 ° C. of 25 mN / m to 38 mN /
  • the contact angle at 25 ° C. with a SiO 2 substrate having a surface free energy of 70 mN / m or more and 80 mN / m or less and a SiN substrate having a surface free energy of 50 mN / m or more and 60 mN / m or less is 13
  • It is the sealing agent for organic EL display elements which is below a degree.
  • the present invention is described in detail below.
  • the sealing agent for organic EL display elements of this invention 1 and the sealing agent for organic EL display elements of this invention 2 it describes as "the sealing agent for organic EL display elements of this invention". To do.
  • the inventors of the present invention have found that the cause of inferior applicability when an organic EL display element sealant is made thin is on an inorganic material film such as SiO 2 that is used for flexibility. It was thought that the sealant around the foreign matter was repelled starting from foreign matter such as SiN present in the substrate, or the sealant could not follow the unevenness of the substrate or the inorganic material film. Therefore, as a result of intensive studies, the present inventors have determined that the contact angles with the SiO 2 substrate and the SiN substrate whose surface free energies are in a specific range are not more than a specific value, thereby reducing the thickness. The present inventors have found that a sealing agent for organic EL display elements excellent in applicability to a substrate or an inorganic material film can be obtained, and the present invention has been completed.
  • the encapsulant for organic EL display elements of the present invention is at 25 ° C. with a SiO 2 substrate having a surface free energy of 70 mN / m to 80 mN / m and a SiN substrate having a surface free energy of 50 mN / m to 60 mN / m.
  • the contact angles are all 13 degrees or less. When both of the contact angles are 13 degrees or less, the organic EL display element sealing agent of the present invention is excellent in the effect of preventing repelling starting from a foreign substance and the wettability with respect to a substrate or an inorganic material film. It will be a thing.
  • the contact angles are preferably 10 degrees or less, more preferably 8 degrees or less, and still more preferably 6 degrees or less.
  • the contact angles are preferably 5 degrees or more, and more preferably 8 degrees or more.
  • the “surface free energy” is measured by an evaluation method based on the Owens-Wendy method from the contact angle between water and methylene iodide at 25 ° C., and specifically, measured using a contact angle meter. Means the value. Examples of the contact angle meter include MSA (manufactured by KRUS). Further, in the present specification, the “contact angle” is a high value of 0.5 mm from the above-described SiO 2 substrate and SiN substrate having the surface free energy at 25 ° C.
  • an inkjet discharge device and a droplet amount of 10 pL.
  • it means a value measured as an angle of each droplet of the sealing agent about 10 seconds after landing when the sealing agent is discharged onto each substrate.
  • the inkjet discharge device include NanoPrinter 500 (manufactured by Microjet Co., Ltd.), and the sealing agent is discharged under the condition of a frequency of 20 kHz.
  • the above “angle of the sealing agent droplet with respect to each substrate” means a value obtained by measuring an image captured by the substrate observation camera of the contact angle meter using image processing software.
  • the contact angle meter include CAM200 (manufactured by KSV INSTRUMENTS), and examples of the image processing software include CAM2008 (manufactured by KSV INSTRUMENTS).
  • Examples of the method of setting the contact angles to 13 degrees or less include a method of setting the solubility parameter of the entire curable resin in a range described later, a method of combining a resin having good wettability with each substrate, and the like.
  • Examples of the method for setting the above contact angles to 5 degrees or more include, for example, a method of adding a resin having a high surface tension, a method of combining a resin having good wettability with a resin that is not good for each substrate, and the like. It is done.
  • the preferable upper limit of the viscosity in 25 degreeC is 30 mPa * s.
  • the sealing agent for organic EL display elements of this invention 1 is excellent in inkjet applicability
  • the upper limit with a more preferable viscosity of the sealing agent for organic EL display elements of this invention 1 is 20 mPa * s.
  • the minimum with a preferable viscosity of the sealing agent for organic EL display elements of this invention 1 is 5 mPa * s.
  • the “viscosity” means a value measured using an E-type viscometer under the conditions of 25 ° C. and 100 rpm.
  • the preferable upper limit of the viscosity in 25 degreeC is 30 mPa * s.
  • the viscosity is 30 mPa ⁇ s or less
  • the organic EL display element sealant of the second aspect of the present invention is more excellent in ink jet coatability.
  • the upper limit with a more preferable viscosity of the sealing agent for organic EL display elements of this invention 2 is 20 mPa * s.
  • the minimum with a preferable viscosity of the sealing agent for organic EL display elements of this invention 2 is 5 mPa * s.
  • the sealing agent for organic EL display elements of the present invention 1 has a surface tension of the whole sealing agent for organic EL display elements at 25 ° C. of 25 mN / m or more and 38 mN / m or less.
  • the organic EL display element sealant of the first aspect of the invention has excellent ink jet coating properties.
  • the preferable lower limit of the surface tension of the whole encapsulant for organic EL display elements of the present invention is 26 mN / m
  • the preferable upper limit is 37 mN / m
  • the more preferable lower limit is 27 mN / m
  • the more preferable upper limit is 35 mN / m.
  • the “surface tension” means a value measured by a dynamic wettability tester at 25 ° C.
  • the surface tension of the whole sealing agent for organic EL display elements at 25 ° C. is 25 mN / m or more and 38 mN / m or less.
  • the organic EL display element sealant of the second aspect of the present invention is superior in ink jet coating properties.
  • the preferable lower limit of the surface tension of the whole encapsulant for organic EL display elements of the present invention is 26 mN / m
  • the preferable upper limit is 37 mN / m
  • the more preferable lower limit is 27 mN / m
  • the more preferable upper limit is 35 mN / m.
  • the sealing agent for organic EL display elements of this invention contains curable resin.
  • the sealing agent for organic EL display elements of the present invention has a solubility parameter (hereinafter also referred to as “SP value”) of the entire curable resin of 16.5 (J / cm 3 ) 1/2 or more and 19.5 (J / Cm 3 ) 1/2 or less is preferable.
  • SP value solubility parameter
  • the encapsulant for organic EL display elements of the present invention has an effect of preventing repellence starting from foreign matters, and wettability with respect to a substrate or an inorganic material film. It will be better.
  • the more preferable lower limit of the SP value of the entire curable resin is 17.0 (J / cm 3 ) 1/2
  • the more preferable upper limit is 19.2 (J / cm 3 ) 1/2
  • the more preferable lower limit is 17 0.7 (J / cm 3 ) 1/2
  • a more preferable upper limit is 19.0 (J / cm 3 ) 1/2
  • the “solubility parameter” is a value calculated by Fedors' estimation method.
  • the “solubility parameter of the entire curable resin” means the average value of the solubility parameter based on the weight fraction of each curable resin component used in the sealant for organic EL display elements.
  • the sealing agent for organic EL display elements of this invention contains 2 or more types of curable resin as said curable resin, and the difference of SP value between each curable resin is 5 (J / cm ⁇ 3 >) ⁇ 1/2 >. It is preferable that content with respect to all the curable resin of the curable resin used as the following is 95 weight% or more. That is, when calculating the sum of the contents of two or more curable resins so that there is no combination of curable resins in which the difference in SP value between the curable resins exceeds 5 (J / cm 3 ) 1/2 In addition, there is a combination of 95% by weight or more based on the total curable resin.
  • the sealing agent for organic EL display elements obtained by the content of the curable resin having a difference in SP value between each curable resin being 5 (J / cm 3 ) 1/2 or less is 95% by weight or more. However, it is excellent in the effect of preventing repelling starting from a foreign substance and the wettability with respect to the substrate and the inorganic material film.
  • the content of the curable resin in which the difference in SP value between the curable resins is 5 (J / cm 3 ) 1/2 or less is more preferably 98% by weight or more, and 99% by weight or more. Is more preferably 99.9% by weight or more, and particularly preferably 99.99% by weight or more.
  • the sealing agent for organic EL display elements of this invention contains 2 or more types of said curable resin as said curable resin, and the maximum difference of SP value between each curable resin is 5 (J / cm ⁇ 3 >) ⁇ 1 >. / 2 or less is preferable. That is, it is preferable that there is no combination of curable resins in which the difference in SP value exceeds 5 (J / cm 3 ) 1/2 .
  • the maximum difference in SP value between the curable resins is 5 (J / cm 3 ) 1 ⁇ 2 or less, the obtained sealing agent for organic EL display elements prevents repelling starting from foreign matters. The effect and the wettability with respect to the substrate and the inorganic material film are excellent.
  • the maximum difference in SP value between the curable resins is more preferably 4 (J / cm 3 ) 1/2 or less.
  • the SP value of the entire curable resin and the SP value of each curable resin component in the sealing agent for organic EL display elements of the present invention can be determined by purifying the sealing agent for organic EL display elements by chromatography or GC-
  • the structure and composition can be specified by performing composition analysis such as MS and LC-MS, and the SP value can be calculated.
  • the curable resin preferably contains a compound having a siloxane skeleton.
  • a compound having a siloxane skeleton By containing the compound having the siloxane skeleton, it becomes easy to adjust the surface tension of the obtained sealing agent for organic EL display elements, and the resulting coating film is more excellent in flatness.
  • Examples of the compound having a siloxane skeleton include an epoxy compound having a siloxane skeleton, an oxetane compound having a siloxane skeleton, and a (meth) acryl compound having a siloxane skeleton.
  • the compound represented by following formula (1) is preferable.
  • the above “(meth) acryl” means acryl or methacryl
  • the above “(meth) acryl compound” means a compound having a (meth) acryloyl group
  • the above “(meth) “Acryloyl” means acryloyl or methacryloyl.
  • R 1 represents an alkyl group having 1 to 10 carbon atoms
  • X 1 and X 2 are each independently an alkyl group having 1 to 10 carbon atoms, or the following formula (2- 1), (2-2), (2-3) or a group represented by (2-4)
  • X 3 represents the following formulas (2-1), (2-2), (2 -3) or a group represented by (2-4).
  • m is an integer from 0 to 100
  • n is an integer from 0 to 100.
  • at least one of X 1 and X 2 is represented by the following formula (2-1), (2-2), (2-3), or (2-4) Represents a group.
  • R 2 represents a bond or an alkylene group having 1 to 6 carbon atoms
  • R 3 represents hydrogen or 1 carbon atom.
  • R 4 represents a bond or a methylene group
  • R 5 represents hydrogen or a methyl group.
  • the compound having a siloxane skeleton is used for organic EL display elements from the viewpoints of storage stability of the obtained sealing agent for organic EL display elements, adhesion to substrates and inorganic material films, and ejection stability when inkjet coating is performed. It is preferable that the polymer having a number average molecular weight of 100,000 or more is removed in advance before blending with the sealant. Specifically, the content ratio of the high molecular weight compound having a number average molecular weight of 100,000 or more is preferably 0.5% or less in the compound having the siloxane skeleton.
  • the number average molecular weight and the content ratio of the high molecular weight substance are values obtained by measuring in polystyrene using gel permeation chromatography (GPC) using tetrahydrofuran as a solvent. .
  • the content rate of the said high molecular weight body can also be measured by GPC.
  • Examples of the column used for measuring the number average molecular weight in terms of polystyrene by GPC and the content ratio of the high molecular weight substance include Shodex LF-804 (manufactured by Showa Denko KK). Further, the content ratio of the high molecular weight substance is calculated from the area ratio of the GPC.
  • Examples of the method for purifying the compound having a siloxane skeleton include a method for purification by distillation, a method for purification using a column, and the like.
  • the compounds having a siloxane skeleton may be used alone or in combination of two or more.
  • the content of the compound having a siloxane skeleton in the curable resin is preferably less than 40% by weight.
  • the content of the compound having a siloxane skeleton is less than 40% by weight, the obtained sealing agent for organic EL display elements has better wettability.
  • the upper limit with more preferable content of the compound which has the said siloxane skeleton is 35 weight%.
  • the minimum with preferable content of the compound which has the said siloxane skeleton in the said curable resin is 0.1 weight%.
  • the content of the compound having a siloxane skeleton is 0.1% by weight or more, it becomes easier to adjust the surface tension of the obtained sealing agent for organic EL display elements.
  • Examples of the curable resin other than the compound having a siloxane skeleton include, for example, an epoxy compound having no siloxane skeleton (hereinafter, also simply referred to as “epoxy compound”), and an oxetane compound having no siloxane skeleton (hereinafter, simply “ An oxetane compound), a vinyl ether compound having no siloxane skeleton (hereinafter also simply referred to as “vinyl ether compound”), a (meth) acryl compound having no siloxane skeleton (hereinafter simply referred to as “(meth) acryl compound”). And the like).
  • epoxy compounds examples include bisphenol A type epoxy compounds, bisphenol E type epoxy compounds, bisphenol F type epoxy compounds, bisphenol S type epoxy compounds, bisphenol O type epoxy compounds, 2,2′-diallyl bisphenol A type epoxy compounds, Alicyclic epoxy compounds, hydrogenated bisphenol type epoxy compounds, propylene oxide added bisphenol A type epoxy compounds, resorcinol type epoxy compounds, biphenyl type epoxy compounds, sulfide type epoxy compounds, diphenyl ether type epoxy compounds, dicyclopentadiene type epoxy compounds, naphthalene Type epoxy compound, phenol novolac type epoxy compound, orthocresol novolac type epoxy compound, dicyclopentadiene novo Examples thereof include a rack type epoxy compound, a biphenyl novolac type epoxy compound, a naphthalenephenol novolak type epoxy compound, a glycidylamine type epoxy compound, an alkyl polyol type epoxy compound, a rubber-modified epoxy compound, and a glycidyl ester compound.
  • an alkyl polyol type epoxy compound is preferable, and neopentyl glycol diglycidyl ether is most preferable because it is difficult to volatilize and the obtained sealing agent for organic EL display elements is excellent in ink jet coating properties.
  • the said epoxy compound may be used independently and 2 or more types may be used in combination.
  • oxetane compound examples include 3- (allyloxy) oxetane, phenoxymethyl oxetane, 3-ethyl-3-hydroxymethyl oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3-((2 -Ethylhexyloxy) methyl) oxetane, 3-ethyl-3-((3- (triethoxysilyl) propoxy) methyl) oxetane, 3-ethyl-3 ((((3-ethyloxetane-3-yl) methoxy) methyl) And 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 because of excellent curability and low outgassing properties.
  • the said oxetane compound 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.
  • the said vinyl ether compound may be used independently and 2 or more types may be used in combination.
  • Examples of the (meth) acrylic compound include glycidyl (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, dicyclopentenyl (meth) acrylate, and di Cyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, benzyl (meth) acrylate, trimethylolpropane tri (meth) arylate, 1,12-dodecanediol di (meth) acrylate, lauryl (meth) acrylate Etc.
  • the said (meth) acryl compound may be used independently and 2 or more types may be used in combination.
  • 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 photocationic polymerization initiator or a thermal cationic polymerization initiator is preferably used.
  • a radical photopolymerization initiator and a thermal radical polymerization initiator are also used suitably.
  • 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.
  • 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.
  • 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.
  • thermal radical polymerization initiator what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
  • the azo compound include 2,2′-azobis (2,4-dimethylvaleronitrile), azobisisobutyronitrile, and the like.
  • the organic peroxide include benzoyl peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
  • thermal radical polymerization initiators examples include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001, and V-501 (all of which are FUJIFILM 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 curable resin.
  • 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, 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.
  • Examples of the sensitizer include anthracene compounds, thioxanthone compounds, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, methyl o-benzoylbenzoate, Examples include 4,4′-bis (dimethylamino) benzophenone and 4-benzoyl-4′-methyldiphenyl sulfide.
  • Examples of the anthracene compound include 9,10-dibutoxyanthracene.
  • Examples of the 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 curable resin.
  • the content of the sensitizer is 0.01 parts by weight or more, the sensitizing effect is more exhibited.
  • the content of the sensitizer is 3 parts by weight or less, light can be transmitted to a deep part without excessive absorption.
  • the minimum with more preferable content of the said sensitizer is 0.1 weight part, and a more preferable upper limit is 1 weight part.
  • the sealing agent for organic EL display elements of the present invention includes a silane coupling agent, a surface modifier, a reinforcing agent, a softening agent, a plasticizer, a viscosity modifier, an ultraviolet absorber, an antioxidant and the like as necessary.
  • An additive may be contained.
  • the maximum difference in SP value between each component contained in the curable resin and the additive is preferably 5 (J / cm 3 ) 1/2 or less.
  • the said silane coupling agent has a role which further improves the adhesiveness of the sealing agent for organic EL display elements of this invention, and a board
  • the silane coupling agent include 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, and the like. These silane coupling agents may be used independently and 2 or more types may be used together.
  • the content of the silane coupling agent is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the polymerizable compound. When the content of the silane coupling agent is within this range, the effect of improving the adhesiveness is suppressed while suppressing the excess silane coupling agent from bleeding out.
  • the minimum with more preferable content of the said silane coupling agent is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • the said surface modifier has a role which further improves the flatness of the coating film of the sealing agent for organic EL display elements of this invention.
  • examples of 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, the content of the solvent is preferably 0.05% by weight or less, and most preferably no solvent is contained.
  • the sealing agent for organic EL display elements of the present invention for example, using a mixer, additives such as a curable resin, a polymerization initiator, and a silane coupling agent to be added as necessary.
  • the mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll.
  • 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, for example, a spectrometer. Examples of the spectrometer include AUTOMATIC HAZE METER MODEL TC-III DPK (manufactured by Tokyo Denshoku Co., Ltd.).
  • cured material used for the measurement of the said light transmittance and the water vapor transmission rate and moisture content mentioned later can be obtained by irradiating 3000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 365 nm using light sources, such as an LED lamp, for example. it can.
  • 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.
  • 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 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%.
  • 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.
  • 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 photocationic polymerization initiator or the photoradical 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 or SiO X N Y), 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 which is excellent in the applicability
  • membrane can be provided.
  • SiO 2 was chemically deposited with an ICP-CVD apparatus (manufactured by Celbach) at a film thickness of 1000 nm to prepare a SiO 2 base plate.
  • the surface free energy after vapor deposition was measured by an evaluation method according to the Owens-Wendy method from the contact angle between water and methylene iodide using a contact angle meter, and found to be 73.0 mN / m.
  • MSA made by KRUSS
  • the Si atom was 31.3% and the O atom was 63.2%.
  • SiN was chemically deposited with an ICP-CVD apparatus (manufactured by Cellvac) at a film thickness of 1000 nm to prepare a SiN base plate.
  • the surface free energy after the deposition was measured by an evaluation method according to the Owens-Wendy method from the contact angle between water and methylene iodide using a contact angle meter, and found to be 58.0 mN / m.
  • MSA made by KRUSS
  • N atoms were 48.0% with respect to 44.8% Si atoms.
  • Examples 1 to 9, Comparative Examples 1 to 4 According to the blending ratios described in Tables 1 and 2, each material was uniformly stirred and mixed at a stirring speed of 300 rpm using a homodisper type stirring mixer, whereby each of Examples 1 to 9 and Comparative Examples 1 to 4 was A sealant for an organic EL display element was produced.
  • a homodisper type stirring mixer a homodisper L type (manufactured by Primics) was used.
  • the compound having a siloxane skeleton in the table those purified in advance by distillation before mixing with other components were used.
  • the oxetane compound having a siloxane skeleton in the table one obtained by the following method was used.
  • the SiO 2 substrate and the SiN substrate having the surface free energy of 58.0 mN / m obtained in the above-mentioned “(Preparation of SiN substrate)” were respectively discharged.
  • an inkjet discharge device NanoPrinter 500 (manufactured by Microjet Co., Ltd.) was used, and the sealant was discharged at 25 ° C., a droplet volume of 10 pL, a pitch of 800 ⁇ m, a drop from a height of 0.5 mm from the substrate, and a frequency of 20 kHz. It went on condition of.
  • Tables 1 and 2 show contact angles with respect to the respective substrates measured by using image processing software for images taken with a substrate observation camera of a contact angle meter for a sealant droplet about 10 seconds after landing.
  • CAM200 manufactured by KSV INSTRUMENTS
  • CAM2008 was used as the image processing software.
  • Table 1 shows contact angles with respect to the respective substrates measured by using image processing software for images taken with a substrate observation camera of a contact angle meter for a sealant droplet about 10 seconds after landing.
  • CAM200 manufactured by KSV INSTRUMENTS
  • CAM2008 was used as the image processing software.
  • the surface tension measured by Wilhelmy method at 25 degreeC using the surface tension meter was shown to Table 1,2.
  • a surface tension meter DY-300 (manufactured by Kyowa Interface Science Co., Ltd.) was used.
  • Tables 1 and 2 show the viscosities of the encapsulants for organic EL display elements obtained in Examples and Comparative Examples, measured using an E-type viscometer under the conditions of 25 ° C. and 100 rpm.
  • VISCOMETER TV-22 manufactured by Toki Sangyo Co., Ltd.
  • Silicon nitride particles and silica particles were dispersed by a spreader on the SiO 2 substrate having a surface free energy of 73.0 mN / m obtained in the above-mentioned “(Preparation of SiO 2 substrate)”.
  • SN-E10 manufactured by Ube Industries
  • Seahoster manufactured by Nippon Shokubai Co., Ltd.
  • Each of the sealing agents for organic EL display elements obtained in Examples and Comparative Examples was applied to the obtained SiO 2 substrate with an 8 cm ⁇ 8 cm size at a pitch of 48 ⁇ m at a droplet volume of 10 pL using an inkjet discharge device. It apply
  • an inkjet discharge device NanoPrinter 500 (manufactured by Microjet) was used. Three minutes after application, irradiating with a 395 nm UV LED with an illuminance of 1000 mW / cm 2 so that the integrated light quantity becomes 1000 mJ / cm 2 , and assuming the dispersed silicon nitride particles and silica particles as foreign matters, per 10 extracted foreign matters The number of pinholes was confirmed.
  • UV-ozone cleaner As the UV-ozone cleaner, NL-UV253 (manufactured by Nippon Laser Electronics Co., Ltd.) was used. Next, the substrate after the last treatment is fixed to the substrate holder of the vacuum evaporation apparatus, and 200 mg of N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine ( ⁇ -NPD) is put in an unglazed crucible. In another unglazed crucible, 200 mg of tris (8-quinolinolato) aluminum (Alq 3 ) was put, and the pressure in the vacuum chamber was reduced to 1 ⁇ 10 ⁇ 4 Pa.
  • Alq 3 8-quinolinolato
  • 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.
  • 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 having a tungsten resistance heating boat, and lithium fluoride is added to one of the tungsten resistance heating boats in the vacuum vapor deposition apparatus. 200 mg was charged, and 1.0 g of aluminum wire was put in another tungsten resistance heating boat.
  • the inside of the vapor deposition unit of the vacuum vapor deposition apparatus is depressurized to 2 ⁇ 10 ⁇ 4 Pa to form a lithium fluoride film with a thickness of 5 mm at a deposition rate of 0.2 kg / s, and then aluminum with a film thickness of 1000 mm at a rate of 20 kg / s. did.
  • the inside of the vapor deposition unit was returned to normal pressure with nitrogen, and the substrate on which the laminate having the organic light emitting material layer of 10 mm ⁇ 10 mm was arranged was taken out.
  • a mask having an opening of 13 mm ⁇ 13 mm is installed so as to cover the entire laminated body of the substrate on which the obtained laminated body is arranged, and inorganic by plasma CVD method.
  • a material film A was formed.
  • SiH 4 gas and nitrogen gas are used as source gases, the flow rates of each are SiH 4 gas 10 sccm, nitrogen gas 200 sccm, RF power 10 W (frequency 2.45 GHz), chamber temperature 100 ° C., chamber The test was performed under the condition that the internal pressure was 0.9 Torr.
  • the formed inorganic material film A had a thickness of about 1 ⁇ m.
  • the height of a convex part was measured on condition of a feed rate of 0.2 mm / s using a 2CR filter and a stylus of R2 ⁇ m with a surface roughness measuring instrument.
  • a surface roughness measuring instrument SE300 (manufactured by Kosaka Laboratory) was used. The height of the convex portion was confirmed by setting the concave portion on the surface to zero.
  • the sealing agent for organic EL display elements which is excellent in the applicability
  • membrane can be provided.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Epoxy Resins (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne la fourniture d'un agent d'étanchéité d'élément d'affichage électroluminescent organique qui présente une excellente applicabilité à des substrats et à des films de matière inorganique même lors de la formation de films minces. La présente invention est l'agent d'étanchéité d'élément d'affichage électroluminescent organique qui consiste en une résine durcissable et un initiateur de polymérisation, présente une tension de surface à 25 °C de 25 à 38 mN/m et présente un angle de contact à 25 °C de 13 degrés ou moins par rapport à un substrat SiO2 présentant une énergie libre de surface de 70 à 80 mN/m et un substrat de SiN présentant une énergie libre de surface de 50 à 60 mN/m.
PCT/JP2019/012141 2018-03-30 2019-03-22 Agent d'étanchéité d'élément d'affichage électroluminescent organique WO2019188805A1 (fr)

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KR1020207018789A KR20200136878A (ko) 2018-03-30 2019-03-22 유기 el 표시 소자용 봉지제
CN201980021211.4A CN111972046A (zh) 2018-03-30 2019-03-22 有机el显示元件用密封剂
JP2019521508A JP7474052B2 (ja) 2018-03-30 2019-03-22 有機ｅｌ表示素子用封止剤
JP2023196812A JP2024019191A (ja) 2018-03-30 2023-11-20 有機ｅｌ表示素子用封止剤

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