WO2019198470A1

WO2019198470A1 - Sealant for organic electroluminescent display element

Info

Publication number: WO2019198470A1
Application number: PCT/JP2019/012361
Authority: WO
Inventors: 山本　拓也; 七里　徳重; 勝則西出; 千鶴金; 美香笹野
Original assignee: 積水化学工業株式会社
Priority date: 2018-04-09
Filing date: 2019-03-25
Publication date: 2019-10-17
Also published as: KR20200141978A; JPWO2019198470A1; CN112074957A

Abstract

The purpose of the present invention is to provide a sealant for an organic electroluminescent (EL) display element, which has inkjet coating properties, low outgassing properties, and outstanding adhesion to a substrate and an inorganic material film, and with which it is possible to obtain an organic EL display element with outstanding reliability. The present invention is a sealant for an organic EL display element, containing a curable resin and a polymerization initiator, wherein: the curable resin contains a compound represented by formula (1) and a compound represented by formula (2); the content of the compound represented by formula (1), by weight ratio, is 1.0–1.5 times the content of the compound represented by formula (2); the viscosity of the entirety of the sealant for the organic EL display element is 40 mPa·s or less at 25°C; and the surface tension of the entirety of the sealant for the organic EL display element is 15–35 mN/m. In formula (1): each R¹ is independently a bonding hand, a straight-chain or branched-chain C1–18 alkylene group, or a straight-chain or branched-chain C2-18 alkenylene group; R² is a straight-chain or branched-chain C1-18 alkylene group or a straight-chain or branched-chain C2-18 alkenylene group; and n is 0 or 1.

Description

Sealant for organic EL display element

The present invention relates to a sealant for an organic EL display element that can provide an organic EL display element that is excellent in inkjet coating property, low outgassing property, adhesion to a substrate or an inorganic material film, and excellent in reliability.

An 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. When electrons are injected and holes are injected from the other electrode, the electrons and holes are combined in the organic light emitting material layer to emit light. Thus, since the organic EL display element performs self-emission, it has better visibility than a liquid crystal display element that requires a backlight, can be reduced in thickness, and can be driven by a DC low voltage. Has the advantage.

The organic light-emitting material layer and electrodes constituting the organic EL display element have a problem that the characteristics are easily deteriorated by moisture, oxygen, and the like. Therefore, in order to obtain a practical organic EL display element, it is necessary to extend the life by blocking the organic light emitting material layer and the electrode from the atmosphere. 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. Here, 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.

As 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. However, when the sealant is made to have a low viscosity in order to be suitable for application by the ink jet method, outgas is generated, or the obtained organic EL display element is inferior in reliability, etc. There was a problem.

JP 2000-223264 A JP 2005-522891 Gazette JP 2001-307873 A JP 2008-149710 A

In the method of sealing with a silicon nitride film disclosed in Patent Document 1, organic light emission occurs when a silicon nitride film is formed due to unevenness on the surface of the organic EL display element, adhesion of foreign matters, generation of cracks due to internal stress, or the like. The material layer or electrode may not be completely covered. If the coating with the silicon nitride film is incomplete, moisture will enter the organic light emitting material layer through the silicon nitride film.
As a method for preventing moisture from entering into the organic light emitting material layer, Patent Document 2 discloses a method of alternately depositing an inorganic material film and a resin film. Patent Document 3 and Patent Document 4 Discloses a method of forming a resin film on an inorganic material film.
As 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. However, when the sealant is made to have a low viscosity in order to be suitable for application by the ink jet method, outgas is generated, or the obtained organic EL display element is inferior in reliability, etc. There was a problem.
The present invention provides an organic EL display element sealant that can provide an organic EL display element that is excellent in inkjet coating property, low outgassing property, adhesion to a substrate or an inorganic material film, and excellent in reliability. The purpose is to do.

Invention 1 is a sealant for an organic EL display element containing a curable resin and a polymerization initiator, and the curable resin comprises a compound represented by the following formula (1) and the following formula ( 2), the content of the compound represented by the following formula (1) is 1.0 times by weight relative to the content of the compound represented by the following formula (2) The viscosity of the whole sealing agent for organic EL display elements at 25 ° C. is 40 mPa · s or less, and the surface tension of the whole sealing agent for organic EL display elements at 25 ° C. is 15 mN / m. It is a sealing agent for organic EL display elements which is 35 mN / m or less.
Invention 2 is a sealing agent for organic EL display elements containing a curable resin and a polymerization initiator, and the curable resin comprises a compound represented by the following formula (1) and the following formula ( 2), the content of the compound represented by the following formula (1) is 1.0 times by weight relative to the content of the compound represented by the following formula (2) It is 1.5 times or less and is a sealing agent for organic EL display elements used for application | coating by the inkjet method.

In formula (1), each R ¹ independently represents a bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched carbon group having 2 to 18 carbon atoms. R ² is a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms. , N is 0 or 1.

The present invention is described in detail below. In addition, about the matter common to 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.

As a curable resin used for a sealing agent for organic EL display elements, the present inventors have excellent curable properties, low outgassing properties, and relatively low viscosity 3-ethyl-3-((((3-ethyloxetane). The use of -3-yl) methoxy) methyl) oxetane was investigated. However, although the obtained sealant is excellent in curability, it has a problem that it becomes inferior in adhesion to a substrate or an inorganic material film due to curing shrinkage or is unsuitable for inkjet application. As a result of intensive studies, the present inventors have determined that a diepoxy compound having a more specific structure as a curable resin is converted to the 3-ethyl-3-(((3-ethyloxetane-3-yl) methoxy) methyl) oxetane. On the other hand, it was studied to blend so as to have a specific content ratio. As a result, it is possible to obtain an organic EL display element sealant that can provide an organic EL display element that is excellent in inkjet coating property, low outgassing property, adhesion to a substrate or an inorganic material film, and excellent in reliability. As a result, the present invention has been completed.

The sealing agent for organic EL display elements of this invention contains curable resin.
The curable resin contains a compound represented by the above formula (1) and a compound represented by the above formula (2). By using the compound represented by the above formula (1) and the compound represented by the above formula (2) so as to have a content ratio described later, the sealing agent for organic EL display elements of the present invention is an inkjet. The coating property, the low outgassing property, and the adhesion to the substrate and the inorganic material film are excellent.

In the above formula (1), R ¹ is a linear or branched alkylene group having 1 to 18 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms. It is preferably a linear or branched alkylene group having 1 to 18 carbon atoms, more preferably a linear or branched alkylene group having 1 to 3 carbon atoms. More preferred is a methylene group.

In the formula (1), R ² is preferably a linear or branched alkylene group having 1 to 18 carbon atoms, and a linear or branched carbon group having 2 to 5 carbon atoms. An alkylene group is more preferable.

The formula (1), the total preferred lower limit of the number of carbon atoms of the R ¹ and R ² above are 3, a preferred upper limit is 20. When the total number of carbon atoms of R ¹ and R ² is within this range, the obtained sealing agent for organic EL display elements is excellent in low outgassing property and adhesion to a substrate or an inorganic material film. The more preferable lower limit of the total carbon number of R ¹ and R ² is 4, and the more preferable upper limit is 7.

N is preferably 1 in the above formula (1) from the viewpoint of inkjet coating properties of the obtained sealing agent for organic EL display elements.

A preferred lower limit of the boiling point of the compound represented by the formula (1) is 200 ° C. When the boiling point of the compound represented by the above formula (1) is 200 ° C. or higher, it is difficult to volatilize, and the obtained sealing agent for organic EL display elements is more excellent in ink jet coatability. A more preferable lower limit of the boiling point of the compound represented by the formula (1) is 250 ° C.
In addition, the said boiling point in this specification means the value measured on the conditions of 101 kPa using the method based on JISK2233, or the value converted into 101 kPa by the boiling point conversion chart.

Specific examples of the compound represented by the above formula (1) include ethylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl. Examples include ether, 1,2,7,8-diepoxyoctane, 1,2,5,6-diepoxyhexane, and the like. Among these, it is difficult to volatilize, and the resulting sealant for organic EL display elements is excellent in ink jet coating properties. Therefore, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6 -Hexanediol diglycidyl ether is preferred, and neopentyl glycol diglycidyl ether is most preferred.

The content of the compound represented by the formula (1) is a weight ratio with respect to the content of the compound represented by the formula (2), and the lower limit is 1.0 times and the upper limit is 1.5 times. is there. When the content of the compound represented by the above formula (1) is 1.0 times or more of the content of the compound represented by the above formula (2), the sealing agent for an organic EL display element of the present invention is The adhesion to the substrate and the inorganic material film is excellent, and the obtained organic EL display element is excellent in reliability. When the content of the compound represented by the above formula (1) is 1.5 times or less of the content of the compound represented by the above formula (2), the sealing agent for organic EL display elements of the present invention is , Excellent curability and low outgassing properties. The content of the compound represented by the above formula (1) is 1.1 times the preferable lower limit and 1.4 is the preferable upper limit in terms of weight ratio with respect to the content of the compound represented by the above formula (2). Is double.

A preferable lower limit of the total content of the compound represented by the formula (1) and the compound represented by the formula (2) in 100 parts by weight of the curable resin is 30 parts by weight. When the total content of the compound represented by the above formula (1) and the compound represented by the above formula (2) is 30 parts by weight or more, the obtained sealing agent for organic EL display elements is applied by inkjet coating. It is excellent in the property, low outgassing property, and adhesion to the substrate and the inorganic material film. A more preferable lower limit of the total content of the compound represented by the above formula (1) and the compound represented by the above formula (2) is 50 parts by weight.
From the viewpoint of low outgassing property, etc., the preferred upper limit of the total content of the compound represented by the above formula (1) and the compound represented by the above formula (2) in 100 parts by weight of the curable resin is 80 parts by weight.

The curable resin may contain a polymerizable compound other than the compound represented by the formula (1) and the compound represented by the formula (2).
Examples of the other polymerizable compounds include other epoxy compounds other than the compound represented by the formula (1), other oxetane compounds other than the compound represented by the formula (2), and a (meth) acrylic compound. And vinyl ether compounds.
In the present specification, the above “(meth) acryl” means acryl or methacryl, the above “(meth) acryl compound” means a compound having a (meth) acryloyl group, and the above “(meth) “Acryloyl” means acryloyl or methacryloyl.

Examples of the other epoxy compounds 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, and 2,2′-diallyl bisphenol A type epoxy. Compound, cycloaliphatic epoxy compound, hydrogenated bisphenol type epoxy compound, propylene oxide added bisphenol A type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, sulfide type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound , Naphthalene type epoxy compound, phenol novolac type epoxy compound, orthocresol novolac type epoxy compound, dicyclopentadi Examples include en novolac type epoxy compounds, biphenyl novolac type epoxy compounds, naphthalene phenol novolac type epoxy compounds, glycidyl amine type epoxy compounds, alkyl polyol type epoxy compounds, rubber-modified epoxy compounds, glycidyl ester compounds, and epoxy compounds having a siloxane skeleton. It is done. Among them, an epoxy compound having a siloxane skeleton is preferable because the obtained sealing agent for organic EL display elements has excellent wettability with respect to the substrate and the inorganic material film.
Among the epoxy compounds having a siloxane skeleton, those commercially available include, for example, X-22-169, X-22-163, X-22-343, X-22-2046, X-22-4741, -22-173DX, X-22-9002 (both manufactured by Shin-Etsu Chemical Co., Ltd.) and the like.
These other epoxy compounds may be used alone or in combination of two or more.

Examples of the other oxetane compounds 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, phenol novolac oxetane, 1,4-bis (((3-ethyl-3-oxetanyl And oxetane compounds having a siloxane skeleton. Of these, an oxetane compound having a siloxane skeleton is preferable because the obtained sealing agent for organic EL display elements has excellent wettability with respect to a substrate or an inorganic material film.
These other oxetane compounds may be used alone or in combination of two or more.

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 And (meth) acrylic compounds having a siloxane skeleton.
Of these, a (meth) acrylic compound having a siloxane skeleton is preferable because the obtained sealing agent for organic EL display elements has excellent wettability with respect to a substrate or an inorganic material film.
Examples of commercially available (meth) acrylic compounds having the siloxane skeleton include X-22-164, X-22-174DX, X-22-174ASX, X-22-2426, X-22- 2475 (all manufactured by Shin-Etsu Chemical Co., Ltd.).
These (meth) acrylic compounds may be used alone or in combination of two or more.
In the present specification, the “(meth) acrylate” means acrylate or methacrylate.

Examples of the vinyl ether compound include benzyl vinyl ether, cyclohexane dimethanol monovinyl ether, dicyclopentadiene vinyl ether, 1,4-butanediol divinyl ether, cyclohexane dimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, dipropylene glycol. Examples thereof include divinyl ether and tripropylene glycol divinyl ether.
These vinyl ether compounds may be used alone or in combination of two or more.

The sealing agent for organic EL display elements of the present invention contains a polymerization initiator.
As the polymerization initiator, a photocationic polymerization initiator or a thermal cationic polymerization initiator is preferably used. Moreover, according to the kind of said other polymeric compound, 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.

Examples of the anion portion of the ionic photoacid-generating photocationic polymerization initiator 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). Examples of the anion moiety 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.

Examples of the aromatic sulfonium salt 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 tetrafluoroborate, diphenyl-4- (phenylthio) Phenylsulfonium tetrakis (pentafluorophenyl) borate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, bis (4- (di ( 4- (2-hydroxyethoxy)) phenylsulfonio) phenyl) sulfide bishexafluorophosphate, bis (4- (di (4- (2-hydroxyethoxy)) phenylsulfonio) phenyl) sulfide bishexafluoroantimonate, Bis (4- (di (4- (2-hydroxyethoxy)) phenylsulfonio) phenyl) sulfide bistetrafluoroborate, bis (4- (di ( - (2-hydroxyethoxy)) phenylsulfonio) phenyl) sulfide tetrakis (pentafluorophenyl) borate, tris (4- (4-acetylphenyl) thiophenyl) sulfonium tetrakis (pentafluorophenyl) borate, and the like.

Examples of the aromatic iodonium salt 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-methylethyl) Such as phenyl iodonium hexafluoroantimonate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrafluoroborate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrakis (pentafluorophenyl) borate Can be mentioned.

Examples of the aromatic diazonium salt include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis (pentafluorophenyl) borate.

Examples of the aromatic ammonium salt 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. ) -Fe (II) hexafluorophosphate, (2,4-cyclopentadiene-1-yl) ((1-methylethyl) benzene) -Fe (II) hexafluoroantimonate, (2,4-cyclopentadiene-1 -Yl) ((1-methylethyl) benzene) -Fe (II) tetrafluoroborate, (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe (II) tetrakis (penta Fluorophenyl) borate and the like.

Examples of the nonionic photoacid-generating photocationic polymerization initiator 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.

As the thermal cationic polymerization initiator, 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. Of these, sulfonium salts and ammonium salts are preferable.

Examples of the sulfonium salt include triphenylsulfonium tetrafluoroborate and triphenylsulfonium hexafluoroantimonate.

Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.

Examples of the ammonium salt include dimethylphenyl (4-methoxybenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methoxybenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methoxybenzyl) ammonium tetrakis (pentafluorophenyl). Borate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methylbenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorotetrakis (pentafluorophenyl) borate, methylphenyl Dibenzylammonium hexafluorophosphate, methylphenyldibenzylammonium Safluoroantimonate, methylphenyldibenzylammonium tetrakis (pentafluorophenyl) borate, phenyltribenzylammonium tetrakis (pentafluorophenyl) borate, dimethylphenyl (3,4-dimethylbenzyl) ammonium tetrakis (pentafluorophenyl) borate, N , N-dimethyl-N-benzylanilinium hexafluoroantimonate, N, N-diethyl-N-benzylanilinium tetrafluoroborate, N, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N, N-diethyl -N-benzylpyridinium trifluoromethanesulfonic acid and the like.

Examples of commercially available thermal cationic polymerization initiators include thermal cationic polymerization initiators manufactured by Sanshin Chemical Industry, thermal cationic polymerization initiators manufactured by King Industries, and the like.
Examples of the thermal cationic polymerization initiator manufactured by Sanshin Chemical Industry Co., Ltd. include Sun-Aid SI-60, Sun-Aid SI-80, Sun-Aid SI-B3, Sun-Aid SI-B3A, and Sun-Aid SI-B4.
Examples of the thermal cationic polymerization initiator manufactured by King Industries include CXC1612 and CXC1821.

Examples of the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, benzyl, thioxanthone compounds, and the like.

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.
Examples of 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.
Examples of the photo radical polymerization initiator manufactured by Tokyo Chemical Industry Co., Ltd. include benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.

As said thermal radical polymerization initiator, what consists of an azo compound, an organic peroxide, etc. is mentioned, for example.
Examples of the azo compound include 2,2′-azobis (2,4-dimethylvaleronitrile), azobisisobutyronitrile, and the like.
Examples of the organic peroxide include benzoyl peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.

Examples of commercially available thermal radical polymerization initiators include VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001, V-501 (all of which are Fuji Film Wako Pure Chemical Industries, Ltd.). Manufactured) and the like.

The content of the polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the curable resin. When 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. When 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, 9,10-diethoxyanthracene, and 9,10-bis (octanoyloxy) anthracene.
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. When the content of the sensitizer is 0.01 parts by weight or more, the sensitizing effect is more exhibited. When the content of the sensitizer is 3 parts by weight or less, light can be transmitted to a deep part without excessive absorption. The minimum with more preferable content of the said sensitizer is 0.1 weight part, and a more preferable upper limit is 1 weight part.

The sealing agent for organic EL display elements of the present invention may contain a silane coupling agent. The said silane coupling agent has a role which further improves the adhesiveness of the sealing agent for organic EL display elements of this invention, and a board | substrate or an inorganic material film.

Examples of 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 curable resin. When the content of the silane coupling agent is within this range, the effect of improving the adhesiveness is suppressed while suppressing the excess silane coupling agent from bleeding out. The minimum with more preferable content of the said silane coupling agent is 0.5 weight part, and a more preferable upper limit is 5 weight part.

The sealing agent for organic EL display elements of the present invention may further contain a surface adjusting agent as long as the object of the present invention is not impaired. By containing the surface conditioning agent, the flatness of the coating film can be imparted to the sealing agent for organic EL display elements of the present invention.
Examples of the surface conditioner include surfactants and leveling agents.

Examples of the surface conditioner include those based on silicone and fluorine.
Examples of commercially available surface conditioners include BYK-340, BYK-345 (both manufactured by Big Chemie Japan), Surflon S-611 (manufactured by AGC Seimi Chemical Co., Ltd.), and the like.

The content of the surface conditioning agent is preferably 0.01 parts by weight and preferably 5 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the surface conditioning agent is within this range, the surface tension of the entire sealing agent for organic EL display elements of the present invention can be adjusted more easily. The minimum with more preferable content of the said surface conditioning agent is 0.1 weight part, and a more preferable upper limit is 3 weight part.

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.

Moreover, the sealing agent for organic EL display elements of this invention contains well-known various additives, such as a reinforcing agent, a softening agent, a plasticizer, a viscosity modifier, a ultraviolet absorber, antioxidant, as needed. May be.

As a method for producing 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 polymerization initiator and an additive such as a silane coupling agent added if necessary.

The sealing agent for organic EL display elements of the present invention 1 has an upper limit of viscosity at 25 ° C. of 40 mPa · s. By the said viscosity being 40 mPa * s or less, the sealing agent for organic EL display elements of this invention 1 is excellent in inkjet applicability | paintability. The upper limit with the preferable viscosity of the sealing agent for organic EL display elements of this invention 1 is 20 mPa * s.
Moreover, the minimum with a preferable viscosity of the sealing agent for organic EL display elements of this invention 1 is 5 mPa * s.
In addition, the said viscosity in this specification means the value measured on 25 degreeC and 100 rpm conditions using an E-type viscosity meter.

As for the sealing agent for organic EL display elements of this invention 2, the preferable upper limit of the viscosity in 25 degreeC is 40 mPa * s. By the said viscosity being 40 mPa * s or less, the sealing agent for organic EL display elements of this invention 2 becomes more excellent by inkjet applicability | paintability. 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.
Moreover, 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 lower limit of surface tension at 25 ° C. of 15 mN / m and an upper limit of 35 mN / m. When the surface tension is within this range, 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 sealant for organic EL display elements of the present invention 1 is 20 mN / m, the preferable upper limit is 30 mN / m, the more preferable lower limit is 22 mN / m, and the more preferable upper limit is 28 mN / m.
The surface tension can be measured with a dynamic wettability tester at 25 ° C.

As for the sealing agent for organic EL display elements of this invention 2, the preferable minimum of the surface tension in 25 degreeC is 15 mN / m, and a preferable upper limit is 35 mN / m. When the surface tension is within this range, the organic EL display element sealant of the second aspect of the present invention is superior in ink jet coating properties. The more preferable lower limit of the surface tension of the sealing agent for organic EL display elements of the present invention 2 is 20 mN / m, the more preferable upper limit is 30 mN / m, the still more preferable lower limit is 22 mN / m, and the still more preferable upper limit is 28 mN / m.

The preferable minimum of the total light transmittance of the light in the wavelength of 380 nm or more and 800 nm or less of the hardened | cured material of the sealing agent for organic EL display elements of this invention is 80%. When the total light transmittance is 80% or more, the obtained organic EL display element has superior optical characteristics. A more preferable lower limit of the total light transmittance is 85%.
The total light transmittance can be measured using a spectrometer such as AUTOMATIC HAZE METER MODEL TC-III DPK (manufactured by Tokyo Denshoku). Moreover, the hardened | 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.

In the sealing agent for organic EL display elements of the present invention, 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 μm. When 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%.
As 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 μm 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. When the moisture permeability is 100 g / m ² or less, the effect of preventing 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.

In the encapsulant for organic EL display elements of the present invention, 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. When the moisture content of the cured product is less than 0.5%, the effect of preventing the deterioration of the organic light emitting material layer due to moisture in the cured product is excellent, and the obtained organic EL display element is excellent in reliability. It becomes. A more preferable upper limit of the moisture content of the cured product is 0.3%.
Examples of the method for measuring the moisture content include a method of obtaining by a Karl Fischer method in accordance with JIS K 7251, and a method of obtaining a weight increment after water absorption in accordance with JIS K 7209-2.

As a method for producing an organic EL display element using the sealing agent for organic EL display elements of the present invention, for example, a step of applying the sealing agent for organic EL display elements of the present invention to a substrate by an inkjet method, And a method of curing the applied sealing agent for organic EL display elements by light irradiation and / or heating.

In the step of applying the organic EL display element sealant of the present invention to the substrate, 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.

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.

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.
As the inorganic material forming the inorganic material layer can be a conventionally known, for example, silicon nitride (SiN _x), silicon oxide (SiO _x), and the like. The inorganic material film may be a single layer or may be a laminate of a plurality of types of layers. Moreover, you may coat | cover the said laminated body by repeating alternately the said inorganic material film | membrane and the resin film which consists of the sealing agent for organic EL display elements of this invention.

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. You may have.
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.
When the one substrate is a substrate on which the laminate is not formed, 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 | coat the sealing agent for organic EL display elements. That is, apply the entire surface to the location of the laminate when the other substrate is bonded, or the location of the laminate is complete when the other substrate is bonded. 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.
When the step of curing the organic EL display element sealant by light irradiation and / or heating is performed before the step of bonding the one base material and the other base material, the organic EL display of the present invention. The device sealant 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.

In the step of bonding the one base material and the other base material, 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. When the degree of vacuum in the reduced-pressure atmosphere is within this range, the one substrate and the other substrate can be used without spending a long time to achieve a vacuum state due to the airtightness of the vacuum apparatus 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.

ADVANTAGE OF THE INVENTION According to this invention, the sealing agent for organic EL display elements which can obtain the organic EL display element which is excellent in inkjet applicability | paintability, low outgas property, and the adhesiveness with respect to a board | substrate or an inorganic material film, and excellent in reliability. Can be provided.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples.

(Examples 1 to 7, Comparative Examples 1 to 6)
According to the blending ratios described in Tables 1 and 2, each material was stirred and mixed uniformly at a stirring speed of 3000 rpm using a homodisper type stirring mixer (Primix Co., Ltd., “Homodisper L type”). Sealants for organic EL display elements of Examples 1 to 7 and Comparative Examples 1 to 6 were prepared.
About each sealing agent for organic EL display elements obtained in Examples and Comparative Examples, measurement was performed using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”) at 25 ° C. and 100 rpm. Tables 1 and 2 show the measured viscosity and the surface tension measured at 25 ° C. using a dynamic wettability tester (Reska, “WET-6100 type”).

<Evaluation>
The following evaluation was performed about each sealing agent for organic EL display elements obtained by the Example and the comparative example. The results are shown in Tables 1 and 2.

(1) Inkjet applicability (1-1) Inkjet ejection properties Each of the organic EL display element sealants obtained in Examples and Comparative Examples was used with an inkjet ejection device (“NanoPrinter500” manufactured by Microjet Co., Ltd.). Then, 1000 drops were applied at a speed of 5 m / second at a pitch of 500 μm on alkali-washed non-alkali glass (“AN100” manufactured by Asahi Glass Co., Ltd.) with a drop volume of 30 picoliters.
When the number of droplets that could not be applied was 0, “０”, when the number of droplets that could not be applied was 1 or more and less than 5, “○”, droplets that could not be applied The ink jetting property was evaluated as “Δ” when the number of droplets was 5 or more and less than 20, and “X” when the number of droplets that could not be applied was 20 or more.

(1-2) Wetting and spreading property Each of the sealing agents for organic EL display elements obtained in the examples and comparative examples is a liquid of 30 picoliters using an inkjet discharge device (“NanoPrinter500” manufactured by Microjet). With a drop amount, 1000 drops were applied on alkali-washed non-alkali glass ("AN100" manufactured by Asahi Glass Co., Ltd.) The coating conditions were set to a pitch of 800 μm and a frequency of 20 kHz from a height of 0.5 mm from the substrate. The diameter of the droplet on the alkali-free glass 10 minutes after the application was measured, and “◎” when the diameter of the droplet was 180 μm or more, and “when” the diameter of the droplet was 150 μm or more and less than 180 μm. The case where the diameter of the droplet was 120 μm or more and less than 150 μm was evaluated as “Δ”, and the case where the diameter of the droplet was less than 120 μm was evaluated as “X”.

(2) Low outgassing property Outgas generated during heating of the cured product of the sealing agent for organic EL display elements obtained in the examples and comparative examples was measured by a gas chromatograph by the headspace method shown below.
First, 100 mg of each organic EL display element sealant was applied to a thickness of 300 μm with an applicator, and then the UV light with a wavelength of 365 nm was irradiated with 3000 mJ / cm ² with an LED lamp to cure the sealant. Next, the obtained sealant cured product was put in a headspace vial, the vial was sealed, heated at 100 ° C. for 30 minutes, and the generated gas was measured by the headspace method.
When the generated gas is less than 400 ppm, “「 ”, when it is 400 ppm or more and less than 600 ppm,“ ◯ ”, when it is 600 ppm or more and less than 800 ppm,“ △ ”, when it is 800 ppm or more,“ × ” ”Was evaluated for low outgassing.

(3) Adhesiveness to inorganic material film Each glass EL device sealing agent obtained in Examples and Comparative Examples is formed on a glass on which a silicon nitride film having a thickness of 300 nm is formed in advance using a spin coater. To a thickness of 10 μm. Next, ultraviolet light having a wavelength of 365 nm was irradiated with an LED lamp at 3000 mJ / cm ² and further heated at 100 ° C. for 30 minutes to cure the organic EL display element sealant to obtain a resin film.
A cross-cut test with a cut interval of 1 mm was performed on the formed resin film in accordance with JIS K 5600-5-6. When the cross-cut test was performed, the peeling was 5% or less, “◎”, when the peeling was more than 5% and 35% or less, “◯”, and the peeling was more than 35% and 65% or less. In the case of “Δ”, the case where peeling exceeded 65% was evaluated as “x”, and the adhesion to the inorganic material film was evaluated.

(4) Reliability of organic EL display element (4-1) Fabrication of a substrate on which a laminate having an organic light emitting material layer is disposed An ITO electrode is placed on a glass substrate (length 25 mm, width 25 mm, thickness 0.7 mm). A substrate having a thickness of 1000 mm was used as a substrate. The substrate was ultrasonically washed with acetone, an aqueous alkali solution, ion-exchanged water, and isopropyl alcohol for 15 minutes, respectively, then washed with boiled isopropyl alcohol for 10 minutes, and a UV-ozone cleaner (manufactured by Nippon Laser Electronics Co., Ltd.). The last treatment was performed with “NL-UV253”).
Next, 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 (α-NPD) is added to the unglazed crucible. 200 mg of tris (8-quinolinolato) aluminum (Alq ₃ ) was put in the crucible, and the pressure in the vacuum chamber was reduced to 1 × 10 ⁻⁴ Pa. Thereafter, the crucible containing α-NPD was heated, and α-NPD was deposited on the substrate at a deposition rate of 15 ｓ / s to form a 600 正孔 hole transport layer. Next, the crucible containing Alq ₃ was heated to form an organic light emitting material layer having a thickness of 600 で at a deposition rate of 15 Å / s. Thereafter, the substrate on which the hole transport layer and the organic light emitting material layer are formed is transferred to another vacuum vapor deposition apparatus, and 200 mg of lithium fluoride is added to a tungsten resistance heating boat in the vacuum vapor deposition apparatus, and an aluminum wire is added to another tungsten boat. 1.0 g was added. After that, 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.

(4-2) Coating with Inorganic Material Film A 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.
In the plasma CVD method, 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 μm.

(4-3) Formation of Resin Protective Film Each of the organic EL display element sealants obtained in Examples and Comparative Examples was applied to the obtained substrate using an inkjet discharge device (“NanoPrinter300” manufactured by Microjet Co., Ltd.). Was used to apply a pattern to the substrate.
Thereafter, an ultraviolet ray having a wavelength of 365 nm was irradiated with 3000 mJ / cm ² using an LED lamp to cure the organic EL display element sealant to form a resin protective film.

(4-4) After forming the coating resin protective film with the inorganic material film B, a mask having an opening of 12 mm × 12 mm is installed so as to cover the entire resin protective film, and the inorganic material is formed by plasma CVD. Film B was formed to obtain an organic EL display element.
The plasma CVD method was performed under the same conditions as in “(4-2) Coating with inorganic material film A”.
The formed inorganic material film B had a thickness of about 1 μm.

(4-5) Observation of light emission state of organic EL display device The obtained organic EL display device was exposed for 100 hours in an environment of a temperature of 85 ° C. and a humidity of 85%, and then a voltage of 3 V was applied to display the organic EL display. The light emission state of the device (the presence or absence of dark spots and pixel periphery quenching) was visually observed. "◎" when there is no dark spot or peripheral quenching, and "◎" when there is no dark spot or peripheral quenching, but "○" when there is a slight decrease in brightness, when dark spot or peripheral quenching is observed Was evaluated as “Δ”, and the case where the non-light emitting portion was remarkably enlarged was evaluated as “x”, and the reliability of the organic EL display element was evaluated.

Claims

An organic EL display element sealing agent containing a curable resin and a polymerization initiator,
The curable resin contains a compound represented by the following formula (1) and a compound represented by the following formula (2),
The content of the compound represented by the following formula (1) is 1.0 to 1.5 times by weight with respect to the content of the compound represented by the following formula (2),
The viscosity of the whole sealing agent for organic EL display elements at 25 ° C. is 40 mPa · s or less, and the surface tension of the whole sealing agent for organic EL display elements at 25 ° C. is 15 mN / m or more and 35 mN / m or less. A sealing agent for organic EL display elements, which is characterized.

In formula (1), each R 1 independently represents a bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched carbon group having 2 to 18 carbon atoms. R 2 is a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms. , N is 0 or 1.
An organic EL display element sealing agent containing a curable resin and a polymerization initiator,
The curable resin contains a compound represented by the following formula (1) and a compound represented by the following formula (2),
The content of the compound represented by the following formula (1) is 1.0 to 1.5 times by weight with respect to the content of the compound represented by the following formula (2),
A sealing agent for organic EL display elements, which is used for coating by an ink jet method.

In formula (1), each R 1 independently represents a bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched carbon group having 2 to 18 carbon atoms. R 2 is a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms. , N is 0 or 1.
The total content of the compound represented by the formula (1) and the compound represented by the formula (2) in 100 parts by weight of the curable resin is 30 parts by weight or more. Sealant for organic EL display elements.